Polymerizable alkylidene-1,3-dioxolane-2-one and use thereof
United States Patent 9062136
Polymerizable alkylidene-1,3-dioxolan-2-one monomers, a process for preparation of polymerizable alkylidene-1,3-dioxolan-2-one monomers, and the use thereof for preparation of polymers. The invention also relates to the homopolymers and copolymers obtained by homopolymerization or copolymerization of alkylidene-1,3-dioxolan-2-one monomers and to the use thereof as a component in 2K binder compositions.
Inventors:
Porta Garcia, Marta (Mannheim, DE)
Weis, Martine (Mannheim, DE)
Lanver, Andreas (Mannheim, DE)
Blanchot, Mathieu (Ludwigshafen, DE)
Flores-figueroa, Aaron (Mannheim, DE)
Klopsch, Rainer (Worms, DE)
Haaf, Christina (Hemsbach, DE)
Kutzki, Olaf (Mannheim, DE)
Application Number:
Publication Date:
06/23/2015
Filing Date:
03/29/2013
Export Citation:
BASF SE (Ludwigshafen, DE)
Primary Class:
International Classes:
C08L63/02; C08F24/00; C08F220/40; C08F222/10; C09D163/02; C09J163/02; C08F220/18
Field of Search:
526/269, 549/229
View Patent Images:
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US Patent References:
Klopsch et al.Klopsch et al.Yu et al.Miller et al.Klopsch et al.Kasahara et al.430/270.1Ohrbom et al.5240835Pettrone et al.3082216Dimroth et al.
Foreign References:
CA1303051CPREPARATION OF 4,4-DISUBSTITUTED 5-METHYLENE-1,3- DIOXOLAN-2-ONESDE1064938BVerfahren zur Oxypropylierung von mehrwertigen AlkoholenDE1098953BVerfahren zur Herstellung von 5-Methylen-4, 4-dialkyl-1, 3-dioxolan-2-onenDE1176358BVerfahren zur Herstellung von gegebenenfalls verschaeumten PolyurethanenDEDEVERFAHREN ZUR HERSTELLUNG VON POLYAETHERPOLYOLENDEVERFAHREN ZUR HERSTELLUNG VON 4,4-DISUBSTITUIERTEN 5-METHYLEN-1,3-DIOXOLAN-2-ONENDEA1Verfahren zur Herstellung von urethangruppenhaltigen (Meth)acryls?ureesternEP0622378Alpha, omega-polymethacrylatediols, process for their preparation and their use for preparing polymers, in particular polyurethanes and polyestersEP0837062Preparation of cyclocarbonatesJPFebruary, 2006JPAMETHOD FOR PRODUCING ?-ALKYLIDENE-1,3-DIOXOLAN-2-ONEJPAMETHOD FOR PRODUCING CYCLIC CARBONIC ESTER COMPOUNDWOA1COPOLYMERS CONTAINING 1,3-DIOXOLAN-2-ONE-4-YL GROUPS AND COATINGS MADE THEREFROMWOA1AQUEOUS CROSS-LINKABLE COATING COMPOSITIONWOA1METHOD FOR SELECTIVE GRAFT POLYMERIZATIONWOA1INTRUSION DETECTORWOA1USE OF CYCLIC CARBONATES IN EPOXY RESIN COMPOSITIONSWOA1PROCESS FOR THE PREPARATION OF 2-OXO-[1,3] DIOXOLANE-4-CARBOXYLIC ACID ESTERSWOA1CURING OF EPOXY RESIN COMPOSITIONS COMPRISING CYCLIC CARBONATES USING MIXTURES OF AMINO HARDENERSWOA1CURING OF EPOXY RESIN COMPOSITIONS COMPRISING CYCLIC CARBONATES USING MIXTURES OF AMINO HARDENERS AND CATALYSTSWOA1EPOXY RESIN COMPOSITIONS, CONTAINING A 2-OXO-[1,3]DIOXOLANE DERIVATIVEJPA
Other References:
Yoshihito Kayaki, et al., “Stereoselective Formation of α-Alkylidene Cyclic Carbonates via Carboxylative Cyclization of Propargyl Alcohols in Supercritical Carbon Dioxide”, Journal of Organic Chemistry, 2007, pp. 647-649.
Yoshihito Kayaki, et al., “N-Heterocyclic Carbenes as Efficient Organocatalysts for CO2 Fixation Reactions”, Angewandte Chemistry, 2009, pp. .
Wataru Yamada, et al., “Silver-Catalyzed Incorporation of Carbon Dioxide into Propargylic Alcohols”, European Journal of Organic Chemistry, 2007, pp. .
Huan-Feng Jiang, et al., “Reusable Polymer-Supported Amine-Copper Catalyst for the Formation of α-Alkylidene Cyclic Carbonates in Supercritical Carbon Dioxide”, European Journal of Organic Chemistry, 2008, pp. .
Andrea Buzas, et al. , “Gold(I)-Catalyzed Formation of 4-Alkylidene-1, 3-dioxolan-2-ones from Propargylic tert-Butyl Carbonates”, Organic Letters, vol. 8, No. 3, 2006, pp. 515-518.
Bungo Ochiai, et al., “Synthesis and Crosslinking of Oligo(carbonate-ketone) Obtained by Radical Polymerization of 4-methylene-5,5-dimethyl-1,3-dioxolan-2-one”, Journal of Network Polymer, vol. 26, No. 3, 2005, pp. 132-137.
Iwhan Cho, et al., “Radical polymerization of 4-methylene-1,3-dioxolan-2-one and its hydrolyzed water-soluble polymer”, Makromol. Chem., Rapid Communication, 1989, pp. 453-456.
International Search Report issued Jun. 5, 2013 in PCT/EP (with English translation of categories of cited documents).
Primary Examiner:
Choi, Ling
Assistant Examiner:
Wang, Chun-cheng
Attorney, Agent or Firm:
Oblon, McClelland, Maier & Neustadt, L.L.P.
The invention claimed is:
A compound of formula I
wherein R1 and R2 are each independently hydrogen, C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C5-C6-cycloalkyl, phenyl or phenyl-C1-C4- R3 is hydrogen, C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C5-C6-cycloalkyl, phenyl or phenyl-C1-C4- R4 is hydrogen, C1-C4-alkyl, CH2COOR8, phenyl or phenyl-C1-C4- R5 and R6 are each independently hydrogen or C1-C4-alkyl, or one of R5 and R6 may also be COOR8 or CH2COOR8; A is a chemical bond or C1-C4- X is O or NR7; Z is a chemical bond, PO2, SO2 or C═O; Y is a chemical bond, CH2 or CHCH3; R7, if present, is C1-C6- and R8, if present, is hydrogen or C1-C6-alkyl.
The compound according to claim 1, wherein R1 and R2 are each independently hydrogen or C1-C6-alkyl.
The compound according to claim 1, wherein R3 is hydrogen.
The compound according to claim 1, wherein A is ethanediyl.
The compound according to claim 1, wherein X is O.
The compound according to claim 1, wherein Z is C═O.
The compound according to claim 1, wherein Y is a chemical bond.
A process for preparing the compound according to claim 1, comprising reacting a compound of formula II:
with a compound of formula III:
wherein L is a nucleophilically displa and L′ is hydrogen or a C1-C4-alkylcarbonyl group.
The process according to claim 8, wherein L is OH or C1-C8-alkoxy, Z is CO═, X is O, and the reacting is performed under conditions of an esterification or transesterification.
A polymer having a polymer backbone which is formed from carbon atoms and to which functional groups of the formula I′ are attached
wherein # is a bond to the polymer backbone and R1 and R2 are each independently hydrogen, C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C5-C6-cycloalkyl, phenyl or phenyl-C1-C4- R3 is hydrogen, C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C5-C6-cycloalkyl, phenyl or phenyl-C1-C4- A is a chemical bond or C1-C4- X is O or NR7; Z is a chemical bond, PO, SO2 or C═O; Y is a chemical bond, CH2 or CHCH3; and R7, if present, is C1-C6-alkyl.
A polymer formed from polymerized ethylenically unsaturated compounds M, wherein the compounds M comprise at least 1% by weight, based on a total amount of the ethylenically unsaturated compounds forming the polymer, of the compound according to claim 1.
The polymer according to claim 10, in a form of a homopolymer of a compound of formula I.
The polymer according to claim 10, comprising from 1 to 99% by weight of a compound of formula I and of from 1 to 99% by weight of a monoethylenically unsaturated comonomer b, a conjugatedly diethylenically unsaturated comonomer b, or both, in copolymerized form.
The polymer according to claim 13, wherein the comonomer b is at least one selected from the group consisting of monoethylenically unsaturated C3-C8-monocarboxylic acid, monoethylenically unsaturated C4-C8-dicarboxylic acid, amides an amide of monoethylenically unsaturated C3-C8-mono- or C4-C8-dicarboxylic acids, an anhydride of monoethylenically unsaturated C4-C8-dicarboxylic acids, a hydroxy-C2-C4-alkyl ester of monoethylenically unsaturated C3-C8-mono- or C4-C8-dicarboxylic acids, a monoethylenically unsaturated sulfonic acid or a salt thereof, a monoethylenically unsaturated nitrile having 3 to 5 carbon atoms, a N-vinylheterocycle, a monoethylenically unsaturated compound having a poly-C2-C4-alkylene oxide group, a vinylaromatic hydrocarbon, esters an ester of monoethylenically unsaturated C3-C8-monocarboxylic acids with C1-C20-alkanols, C5-C6-cycloalkanols, phenyl-C1-C4-alkanols or phenoxy-C1-C4-alkanols, a diester of monoethylenically unsaturated C4-C8-dicarboxylic acids with C1-C20-alkanols, C5-C8-cycloalkanols, phenyl-C1-C4-alkanols or phenoxy-C1-C4-alkanols, a C1-C20-alkylamide of monoethylenically unsaturated C3-C8-monocarboxylic acids, a di-C1-C10-alkylamide of monoethylenically unsaturated C3-C8-monocarboxylic acids, a vinyl ester of aliphatic carboxylic acids having 1 to 20 carbon atoms, a conjugatedly diethylenically unsaturated C4-C10-olefin, a C2-C20-olefin, a halogen-substituted C2-C20-olefin, a monoethylenically unsaturated monomer having one or two epoxide groups, a monoethylenically unsaturated monomer having a carbonate group, an ester of monoethylenically unsaturated C3-C8-monocarboxylic acids with C8-C24-alkenols or C8-C24-alkanedienols and an ester of monoethylenically unsaturated dicarboxylic acids with C8-C24-alkenols or C8-C24-alkane-dienols.
The polymer according to claim 13, further comprising, in copolymerized form, a comonomer c having 2, 3 or 4 nonconjugated, ethylenically unsaturated double bonds.
The polymer according to claim 10, wherein the polymer is a component in 2K binder compositions.
The polymer according to claim 16, wherein the binder composition comprises one a compound having at least two functional groups F selected from the group consisting of an aliphatic hydroxyl group, a primary amino group, a secondary amino group, a phosphine group, a phosphonate group and a mercaptan group.
The polymer according to claim 17, wherein a molar ratio of functional groups of the formula I′ to the functional groups F is from 1:10 to 10:1.
The compound according to claim 1, wherein R1 and R2 are each independently hydrogen or methyl.
Description:
The present invention relates to polymerizable alkylidene-1,3-dioxolan-2-one monomers, to the preparation thereof and to the use thereof for preparation of polymers. The invention also relates to the homo- and copolymers obtainable by homo- or copolymerization of alkylidene-1,3-dioxolan-2-one monomers and to the use thereof as a component in 2K binder compositions.Polyurethanes (PUs) find use in countless fields, for example the production of foams, paints, coatings and adhesives. A common feature of all polyurethanes is that they are prepared by polyaddition of polyamines or polyols onto polyvalent isocyanates. Skilful selection of the polyamine or polyol component allows control of the profile of properties of the polyurethane obtained.A disadvantage is found to be the high reactivity of the polyvalent isocyanates, which leads to a high moisture sensitivity, which is exploited for the production of foams, but is undesirable for other applications, for example coatings. Although polyvalent isocyanates are storable over a prolonged period under anhydrous conditions, the reaction with water sets in the course of curing, and so it is necessary to work under very dry conditions. Over and above the moisture sensitivity, the aromatic isocyanates (MDI, TDI) in particular have a tendency to discoloration. Another problem is the health concerns associated with some diisocyanates. For instance, it is known that diisocyanates can trigger allergies on skin contact or inhalation. For this reason, oligomers of diisocyanates have been developed, which are easier to handle due to their lower volatility. Nevertheless, there is fundamentally a requirement for alternatives to the polyisocyanates known from the prior art.Alkylidene-1,3-dioxolan-2-ones, which are also referred to hereinafter as exo-vinylene carbonates, have been the subject of various descriptions in the literature, for example in DE 1098953, DE 3433403, EP 837062, JP , JP , J. Org. Chem. 7-649, Angew. Chem. , , Eur. J. Org. Chem. -2607, Eur. J. Org. Chem. -2312, Org. Lett. 5-518. Alkylidene-1,3-dioxolan-2-ones are proposed therein as synthesis units for the production of active ingredients and effect substances.WO
describes the use of alkylidene-1,3-dioxolan-2-ones together with aminic hardeners as additives in epoxy resin compositions.WO 96/26224 describes the copolymerization of 4-vinyl-1,3-dioxolan-2-ones with ethylenically unsaturated comonomers. The polymers obtained have 1,3-dioxolan-2-one groups and are used together with amino-functional crosslinkers for production of coatings.US
discloses 4-(meth)acryloxyalkyl-1,3-dioxolan-2-ones which are polymerized with ethylenically unsaturated comonomers to give copolymers having 1,3-dioxolan-2-one groups bonded via alkyloxycarbonyl units. The polymers are reacted with aminic compounds to obtain graft polymers having urethane and hydroxyl groups. The graft polymers are used in coating materials.However, the reactivity of the polymers which have 1,3-dioxolan-2-one groups and are known from the prior art is unsatisfactory, especially in the reaction with amines. In addition, the reaction of 1,3-dioxolan-2-ones with, for example, amines or alcohols forms hydroxyl groups, which can be found to be disadvantageous in various applications.It has now been found that, surprisingly, the compounds of the formula I which are described in detail hereinafter and have an alkylidene-1,3-dioxolan-2-one group and a further ethylenically unsaturated double bond can be free-radically polymerized while conserving the alkylidene-1,3-dioxolan-2-one group. This is surprising since there are various descriptions in the literature of polymerization of the methylene group in methylene-1,3-dioxolan-2-ones under free- see, for example, Journal of Network Polymer, Japan 2-137, Makromol. Chem., Rapid Commun. 3-456.Accordingly, a first aspect of the invention relates to the compounds of the general formula I defined below
in which R1 and R2 are each independently hydrogen, C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C5-C6-cycloalkyl, phenyl or phenyl-C1-C4-R3 is hydrogen, C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C5-C6-cycloalkyl, phenyl or phenyl-C1-C4-alkyl, where R3 isR4 is hydrogen, C1-C4-alkyl, CH2COOR8, phenyl or phenyl-C1-C4-R5 and R6 are each independently hydrogen or C1-C4-alkyl, or one of the R5 and R6 radicals may also be COORS or CH2COOR8;A is a chemical bond or C1-C4-alkanediyl, where A is especially C1-C4-X is O or NR7;Z is a chemical bond, PO2, SO2 or C═O, where Z is especially C═O;Y is a chemical bond, CH2 or CHCH3, where Y is especiR7, if present, is C1-C6-R8, if present, is hydrogen or C1-C6-alkyl. The homo- or copolymers obtained in the homo- or copolymerization of the compounds of the formula I generally have several functional groups of the formula I′ bonded to the polymer backbone formed from carbon atoms. In formula I′, # represents the bond to the polymer backbone and R1, R2, R3, A, X, Z and Y are each as defined here and hereinafter. Such polymers have a high reactivity compared to compounds having functional groups F from the group of the aliphatic hydroxyl groups, primary and secondary amino groups, phosphine groups, phosphonate groups and mercaptan groups, without having the disadvantages associated with isocyanates. They are therefore particularly suitable as a replacement for polyfunctional isocyanates in numerous applications, especially for 2K binders. They therefore likewise form part of the subject matter of the present invention.Here and hereinafter, the prefix “Cn-Cm—” used to define substituents and chemical compounds states the number of possible carbon atoms of the substituent or compound.Unless stated otherwise, the following general definitions apply in the context of the present invention for the terms used in connection with the substituents:“Alkyl” is a linear or branched alkyl radical having, for example, 1 to 4 (C1-C4-alkyl), 1 to 6 (C1-C6-alkyl) or 1 to 20 carbon atoms (C1-C20-alkyl). Examples of C1-C4-alkyl are methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert-butyl (2-methylpropan-2-yl). Examples of C1-C6-alkyl are, as well as the definitions given for C1-C4-alkyl, additionally n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl. Examples of C1-C20-alkyl are, as well as the definitions given for C1-C6-alkyl, additionally heptyl, octyl, 2-ethylhexyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl and the constitutional isomers thereof.“C1-C4-Alkoxy-C1-C4-alkyl” is an alkyl group which has 1 to 4 carbon atoms and is bonded via an oxygen atom, for example methoxy, ethoxy, n-propoxy, 1-methylethoxy(isopropoxy), n-butoxy, 1-methylpropoxy(sec-butoxy), 2-methylpropoxy(isobutoxy) or 1,1-dimethylethoxy(tert-butoxy), which is bonded in the form of an ether bond via the oxygen to a C1-C4-alkyl group as defined above. Examples are methoxymethyl, 2-methoxyethyl, ethoxymethyl, 3-methoxypropyl, 3-ethoxypropyl.“C6-C6-Cycloalkyl” is a cyclic alkyl radical having 5 to 6 carbon atoms. Examples are cyclopentyl and cyclohexyl.“Phenyl-C1-C4-alkyl” is a phenyl group bonded to a C1-C4-alkyl group as defined above. Examples are benzyl, phenylethyl, phenylpropyl, phenylbutyl.“C1-C4-Alkanediyl” is an alkanediyl having 1 to 4 carbon atoms. Examples are methanediyl, 1,1-ethanediyl, 1,2-ethanediyl, 1-methyl-1,1-ethanediyl, 1-methyl-1,2-ethanediyl, 1,3-propanediyl, 1,4-butanediyl, 1,1-dimethyl-1,2-ethanediyl and 1,2-dimethyl-1,2-ethanediyl.“C1-C8-Alkoxy” is an alkyl group which has 1 to 8 carbon atoms and is bonded via an oxygen atom. Examples are methoxy, ethoxy, n-propoxy, 1-methylethoxy(isopropoxy), n-butoxy, 1-methylpropoxy(sec-butoxy), 2-methylpropoxy(isobutoxy), 1,1-dimethylethoxy(tert-butoxy), n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, 2-ethylpropoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1-ethylbutoxy, 2-ethylbutoxy, 3-ethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,3-dimethylbutoxy, 1-ethyl-2-methylpropoxy and 1-isopropylpropoxy.“C1-C4-Alkylcarbonyl” is a C1-C4-alkyl radical as defined above, bonded via a carbonyl group, for example acetyl, propionyl, butyryl, pivaloyl etc.With regard to preferred embodiments of the invention, the R1, R2, R3, R4, R5, R6, R7, R8, A, X, Z and Y radicals or groups in the compounds of the formula I and the groups of the formula I′ preferably each independently have one or more or all of the following definitions: R1 is hydrogen or C1-C6-alkyl, particularly hydrogen or C1-C4-alkyl and especiR2 is hydrogen or C1-C6-alkyl, particularly C1-C4-alkyl and especiR3 A is C1-C4-alkanediyl, especially methanediyl, 1,2-ethanediyl or 1,3-X is O;Z is C═O;YR4 is hydrogen or C1-C4-alkyl, especiallR5 R6 R7, if present, is C1-C4-R8, if present, is C1-C4-alkyl. The preparation of the compounds of the formula I is generally possible by the process explained in detail hereinafter, which likewise forms part of the subject matter of the present invention. In this process, a compound of the general formula II is reacted with a compound of the general formula III: In formula II, L′ is hydrogen or a hydroxyl or amino protecting group, for example a C1-C4-alkylcarbonyl group. The variables A, X, R1, R2 and R3 are each as defined above, more particularly as defined with preference.In formula III, L is a nucleophilically displaceable leaving group, for example halogen, OH or C1-C8-alkoxy. The variables Y, Z, R4, R5 and R6 are each as defined above, especially as defined with preference.The reaction of the compounds of the formulae II and III can be performed in analogy to known processes for nucleophilic substitution. If L′ is a hydroxyl or amino protecting group, this protecting group is generally removed before the reaction of compound II with compound III, or reaction conditions under which the protecting group is detached are selected, such that the actual reactant is the compound of the formula II in which L′ is hydrogen.In a preferred embodiment of the invention, in formula III, the variable Z is C═O and the variable L is OH or C1-C8-alkoxy. In this case, the reaction of compound III with compound II, optionally after removal of the hydroxyl or amino protecting group, proceeds in the manner of an amidation or esterification or transesterification reaction.More particularly, the esterification or transesterification is suitable for the preparation of compounds of the formula I in which Z is C═O and X is O, A is C1-C4-alkanediyl, R4 is hydrogen or C1-C4-alkyl, especially hydrogen or methyl, and R5 and R6 are each hydrogen. In this case, preferred reactants of the formula III are selected from the C1-C8-alkyl esters of acrylic acid and of methacrylic acid, hereinafter C1-C8-alkyl(meth)acrylates, e.g. methyl, ethyl, n-butyl and 2-ethylhexyl(meth)acrylate, and most preferably C1-C4-alkyl(meth)acrylates, e.g. methyl, ethyl and n-butyl(meth)acrylate.In a particularly preferred embodiment of the invention, in formula III, the variable L is OH or C1-C8-alkoxy, the variable Z is C═O, and, in formula II, the variable X is O, and the reaction of compound II with compound III is conducted under the conditions of an esterification or transesterification. In a specific configuration of this embodiment, L′ in formula II is hydrogen or a C1-C4-alkylcarbonyl group, especially an acetyl group.In a preferred embodiment of the process according to the invention, the compounds of the formula I are prepared by esterification or transesterification under enzyme catalysis.The enzyme-catalyzed esterification or transesterification can be conducted in analogy to the methods described in Biotechnol. Lett. 5-830, Biotechnol. Lett. 1-246, U.S. Pat. No. 5,240,835, WO
or DE , which are fully incorporated here by reference.Enzymes (E) usable for the enzyme-catalyzed esterification or transesterification are, for example, selected from hydrolases, esterases (E.C. 3.1.-.-), lipases (E.C. 3.1.1.3), glycosylases (E.C. 3.2.-.-) and proteases (E.C. 3.4.-.-), in free form or in chemically or physically immobilized form on a carrier, preferably lipases, esterases or proteases. Particular preference is given to Novozym(R) 435 from Novozymes (lipase from Candida antarctica B) or lipase from Aspergillus sp., Aspergillus niger sp., Mucor sp., Penicilium cyclopium sp., Geotricum candidum sp., Rhizopus javanicus, Bukholderia sp., Candida sp., Pseudomonas sp. or porcine pancreas, very particular preference being given to lipase from Candida antarctica B or from Burkholderia sp.The enzyme content in the reaction medium is generally in the range from about 0.1 to 10% by weight, based on the sum of the reactants of the formulae II and III used.The compounds of the formula I can also be prepared by conventional esterification or transesterification under the reaction conditions of an acid-catalyzed esterification or of an acid- or base-catalyzed transesterification which are customary therefor.Suitable acidic catalysts for an acid-catalyzed esterification are in particular protic acids, for example sulfuric acid, sodium hydrogensulfate, hydrochloric acid, phosphoric acid, monosodium dihydrogenphosphate, disodium hydrogenphosphate, pyrophosphoric acid, phosphorous acid, hypophosphorous acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid and mixtures thereof. Also suitable are Lewis acids, for example titanium and tin compounds. Additionally suitable are acidic ion exchange resins, for example sulfonated or carboxylated ion exchange resins, each in the acid form thereof.Suitable basic catalysts for a transesterification are metal hydroxides and/or alkoxides, especially of metals of groups 1, 2 and 13 of the Periodic Table, for example alkali metal hydroxides such as NaOH or KOH, and alkali metal and alkaline earth metal alkoxides, especially the corresponding methoxides or ethoxides such as sodium methoxide or potassium methoxide or sodium ethoxide or potassium ethoxide. Also suitable are ion-exchanging resins.The acidic or basic catalysts are generally used in a concentration of 0.0001% by weight to 20% by weight, preferably 0.001% by weight to 10% by weight, based on the overall reaction mixture.The esterification or transesterification reaction of II with III can be configured, for example, as a batch process. In this case, the compounds of the formulae II and III will generally be added to a reaction vessel and reacted with one another with addition of the catalyst or of the enzyme. Alternatively, the esterification or transesterification reaction can be configured as a semibatchwise process. For this purpose, for example, one of the reactants, for example compound II or compound III, and the catalyst or the enzyme can be initially charged, and the other reactants can be supplied in the course of the reaction. In addition, the compound of the formula I can be prepared by continuous reaction of compound II with compound III. For this purpose, for example, compounds II and III will be supplied continuously to a reaction zone comprising the catalyst, and the compound of the formula I will be withdrawn continuously from the reaction zone, optionally together with the coproducts formed in the reaction, for example alcohol or ester. Optionally, the catalyst or the enzyme will likewise be supplied to the reaction zone. Both in the semibatchwise reaction and in the continuous reaction, the reactants, i.e. the compounds of the formulae II and III, can be conducted, preferably in the liquid phase, through a reaction zone comprising the catalyst or the enzyme as a stationary phase.The reaction time depends upon factors including the temperature, the amount used and the activity of the acid, base or enzyme catalyst, and on the required conversion, and on the structure of the compound II. The reaction time is preferably adjusted such that the conversion of compound II is at least 70%, preferably at least 80%, more preferably at least 90%, even more preferably at least 95% and especially at least 97%. In general, 1 to 48 hours, preferably 1 to 12 hours and more preferably 1 to 6 hours are sufficient for this purpose.The enzyme-catalyzed or conventionally catalyzed esterification or transesterification is effected generally at temperatures of 0 to 100° C., preferably 20 to 80° C. and more preferably 20 to 70° C.The molar ratio of compound II to compound III can be varied within a wide range. Preference is given to using compound III in excess based on the stoichiometry of the reaction. In general, the molar ratio of compound II to compound III is in the range from 1:100 to 1:1, preferably 1:50 to 1:1, more preferably 1:20 to 1:1. The compound of the formula III is preferably present in excess, such that it can be distilled off, for example as an azeotrope, under reduced pressure, together with the coproduct released, generally an alcohol or the ester coproduct formed in a transesterification (when X-L′ in formula II is alkylcarbonyloxy and Y-L in formula III is alkoxycarbonyl). Additionally or alternatively, the water released or the alcohol or ester can be bound, for example, by means of a molecular sieve. In this way, the reaction equilibrium is shifted in favor of the compound of the formula I.The enzyme-catalyzed and the conventionally catalyzed esterification or transesterification can be performed in organic solvents or mixtures thereof, or without addition of solvents. The mixtures are generally substantially anhydrous (i.e. water content below 10% by volume, preferably below 5% by volume, more preferably below 1% by volume).The proportion of organic solvents in the reaction mixture may, for example, be 0.1 to 50% by weight and is, if a solvent is used, preferably in the range from 0.5 to 30% by weight or in the range from 1 to 10% by weight. Preference is given to adding no or less than 1% by weight of organic solvent to the enzyme-catalyzed or conventionally catalyzed esterification or transesterification.The preparation of compound I can be performed in the presence of at least one polymerization inhibitor. The polymerization inhibitors used may, for example, be 4-methoxyphenol (MeHQ), hydroquinone, 2,5-di-tert-butylhydroquinone, 2,6-di-tert-butyl-p-cresol, nitroso compounds such as isoacryloyl nitrate, nitrosodiphenylamine, N-nitrosocyclohexylhydroxylamine, methylene blue, phenothiazine or diphenylamine. Preference is given to using 4-methoxyphenol (MeHQ) as the polymerization inhibitor.The polymerization inhibitors are used generally, based on the amount of the compounds of the formula III, from 1 to 10 000 ppm, preferably from 10 to 5000 ppm, more preferably from 30 to 2500 ppm and especially from 50 to 1500 ppm.The compounds of the formula III are known and are generally commercially available.The compounds of the formula II can be prepared in analogy to known processes for preparing alkylidene-1,3-dioxolan-2-ones, as described, for example, in the prior art cited at the outset. Preferred compounds of the formula II in which R3 is hydrogen can be prepared, for example, by reacting the compound of the formula IV with CO2, preferably using a catalyst (see scheme 1): In scheme 1, R1, R2, A and X are each as defined above. L″ is an alcohol or amino protecting group and particularly C1-C4-alkylcarbonyl, especially acetyl. X is particularly oxygen. A is particularly C1-C4-alkanediyl.Useful catalysts are in principle transition metal catalysts which comprise, as the active metal, for example, silver, copper, gold, palladium or platinum, for example silver salts such as silver acetate, silver carbonate, copper(II) salts such as copper acetate or copper(I) halides such as CuI, CuBr, CuCl, and also palladium(0) catalysts, the aforementioned transition metal compounds optionally being usable in combination with an organic amine, for example a tri-C1-C6-alkylamine such as triethylamine, or an amidine base such as 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), or with an organic phosphine, e.g. trialkylphosphines or triarylphosphines such as tributylphosphine and triphenylphosphine, or in combination with a mixture of one of the aforementioned phosphines with an ammonium salt, for example tri-C1-C6-alkylammonium halides or tetra-C1-C6-alkylammonium halides. Further useful catalysts include organic phosphines as such, for example trialkylphosphines or triarylphosphines such as tributylphosphine or triphenylphosphine, and sterically hindered carbenes, for example 1,3-substituted 2,3-dihydroimidazol-2-ylidene compounds such as 1,3-diisopropyl-2,3-dihydro-4,5-imidazol-2-ylidene, or the CO2 adducts thereof, and combinations thereof with the aforementioned phosphines. The reaction can be conducted at ambient pressure or preferably under elevated pressure, for example at 50 to 500 bar, or in supercritical CO2. With regard to the reaction conditions, reference is made to the aforementioned literature.Instead of CO2, it is also possible to use a carboxylic anhydride, for example bis(tert-butyl)dicarbonic anhydride (Boc2O). In this case, the reaction is typically effected in two stages, in which case, in the first stage, the compound IV is reacted with an ester of biscarbonic anhydride, for example with Boc2O, in the presence of a base, for example sodium hydride, and the ester obtained is cyclized in the presence of a transition metal catalyst, for example a gold catalyst. Such a procedure is described, for example, in Org. Lett. 5-518, which is hereby incorporated by reference.The invention also provides polymers comprising at least one compound of the formula I in polymerized form. Such polymers are typically obtainable by homo- or copolymerizing ethylenically unsaturated monomers M, the ethylenically unsaturated monomers M comprising at least one monomer of the general formula I (monomer a) and optionally one or more ethylenically unsaturated comonomers. Such polymers have a polymer backbone formed from carbon atoms, to which generally at least two groups of the general formula I′, for example 2 to 1000 groups of the formula I′, are bonded. Accordingly, such a polymer has at least two repeat units of the formula I″: The proportion of compounds of the general formula I is preferably at least 10% by weight, particularly at least 15% by weight and especially at least 20% by weight, based on the total amount of monomers M to be polymerized, and may be up to 100% by weight. Accordingly, the proportion of repeat units of the general formula I″ is preferably at least 10% by weight, particularly at least 15% by weight and especially at least 20% by weight, based on the total amount of repeat units present in the polymer, and may be up to 100% by weight.A first embodiment of the invention relates to homopolymers of a compound of the formula I, i.e. the polymers are, apart from their end groups, formed exclusively from a particular repeat unit of the general formula I″.A second embodiment of the invention relates to copolymers of at least two different compounds of the formula I, i.e. the polymers are, apart from their end groups, formed exclusively from two or more different repeat units of the general formula I″.A third embodiment of the invention relates to copolymers formed from at least one compound of the formula I with at least one, e.g. 1, 2 or 3, different ethylenically unsaturated comonomer, i.e. compounds which do not have any group of the formula I′. Such inventive copolymers have, as well as repeat units of the formula I″, also repeat units derived from the polymerized comonomer.Suitable comonomers are particularly monoethylenically unsaturated comonomers, but also conjugatedly diethylenically unsaturated compounds. These are also referred to hereinafter as comonomers b. The comonomers b include, for example: b1 monoethylenically unsaturated C3-C8-mono- and C4-C8-dicarboxylic acids, for example acrylic acid, methacrylic acid, vinylacetic acid, crotonic acid, fumaric acid, maleic acb2 amides of monoethylenically unsaturated C3-C5-mono- and C4-C5-dicarboxylic acids, such as acrylamide, methacrylamide, fumab3 anhydrides of monoethylenically unsaturated C4-C8-dicarboxylic acids, suchb4 hydroxy-C2-C4-alkyl esters of monoethylenically unsaturated C3-C8-mono- andC4-C8-dicarboxylic acids, such as 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 3-hydroxypropyl acrylate, 2-hydroxybutyl acrylate, 4-hydroxybutyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl methacrylate, 2-hydroxybutyl methacrylate, 4-hydrob5 monoethylenically unsaturated sulfonic acids and salts thereof, for example vinylsulfonic acid, allylsulfonic acid, methallylsulfonic acid, styrenesulfonic acid, 2-acrylamido-2-methylpropanesulfonic acid, 2-methacrylamido-2-methylpropanesulfonic acid, 2-acrylamidoethanesulfonic acid, 2-meth-acrylamidoethanesulfonic acid, 2-acryloyloxyethanesulfonic acid, 2-meth-acryloyloxyethanesulfonic acid, 3-acryloyloxypropanesulfonic acid and 2-methacryloyloxyb6 monoethylenically unsaturated nitriles having 3 to 5 carbon atoms, such as acrylonitrile ab7 N-vinylheterocycles such as N-vinylpyrrolidone, N-vinylcaprolactam, N-b8 monoethylenically unsaturated compounds having at least one poly-C2-C4-alkylene oxide group, for example vinyl and allyl ethers of poly-C2-C4-alkylene glycols or C1-C10-alkyl poly-C2-C4-alkylene glycols, esters of monoethylenically unsaturated mono- and dicarboxylic acids having 3 to 8 carbon atoms with poly-C2-C4-alkylene glycols or C1-C10-alkyl poly-C2-C4-b9 vinylaromatic hydrocarbons such as styrene, α-methylstyrene and the b10 esters of monoethylenically unsaturated C3-C8-monocarboxylic acids with C1-C20-alkanols, C5-C8-cycloalkanols, phenyl-C1-C4-alkanols or phenoxy-C1-C4-alkanols, for example esters of acrylic acid with C1-C20-alkanols, such as methyl acrylate, ethyl acrylate, n-butyl acrylate, 2-butyl acrylate, isobutyl acrylate, tert-butyl acrylate, 2-ethylhexyl acrylate, decyl acrylate, lauryl acrylate and stearyl acrylate, esters of acrylic acid with C5-C10-cycloalkanols such as cyclohexyl acrylate, esters of acrylic acid with phenyl-C1-C4-alkanols, such as benzyl acrylate, 2-phenylethyl acrylate and 1-phenylethyl acrylate, esters of acrylic acid with phenoxy-C1-C4-alkanols, such as 2-phenoxyethyl acrylate, esters of methacrylic acid with C1-C20-alkanols, preferably C1-C10-alkanols, such as methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, 2-butyl methacrylate, isobutyl methacrylate, tert-butyl methacrylate, 2-ethylhexyl methacrylate, decyl methacrylate, lauryl methacrylate and stearyl methacrylate, esters of methacrylic acid with C5-C10-cycloalkanols, such as cyclohexyl methacrylate, esters of methacrylic acid with phenyl-C1-C4-alkanols, such as benzyl methacrylate, 2-phenylethyl methacrylate and 1-phenylethyl methacrylate, and esters of methacrylic acid with phenoxy-C1-C4-alkanols, such as 2-phenob11 diesters of monoethylenically unsaturated C4-C8-dicarboxylic acids with C1-C20-alkanols, C5-C8-cycloalkanols, phenyl-C1-C4-alkanols or phenoxy-C1-C4-b12 C1-C20-alkylamides and di-C1-C20-alkylamides of monoethylenically unsaturated C3-C8-monocarboxylic acids, especially the C1-C20-alkylamides and di-C1-C20-alkylamides of acrylic acid and of methacrylic acid, for example ethylacrylamide, dimethylacrylamide, diethylacrylamide, n-propylacrylamide, n-butylacrylamide, laurylacrylamide, stearylacrylamide, ethylmethacrylamide, dimethylmethacrylamide, diethylmethacrylamide, n-propylmethacrylamide, n-butylmethacrylamide, laurylmethacrylamide, sb13 vinyl esters of aliphatic carboxylic acids having 1 to 20 carbon atoms, for example vinyl acetate, vinyl propionate, vinyl butyrate, vinyl hexanoate, vinyl lauratb14 conjugatedly diethylenically unsaturated C4-C10-olefins, such as bub15 C2-C20-olefins, such as ethylene, propene, 1-butene, 2-butene, isobutene, 1-hexene, 1-octene, diisobutene and 1-b16 halogen-substituted C2-C20-olefins, such as vinyl chloride, vinylidene chloride, vinyl bromide, fluoroethene, 1,1-difluoroethene ab17 monoethylenically unsaturated monomers having one or two epoxide groups, such as mono- and diesters of monoethylenically unsaturated mono- or dicarboxylic acids, especially mono- and diesters of C3-C10-epoxyalkanols, e.g. mono- or diglycidyl esters of monoethylenically unsaturated C3-C8-mono- or C4-C8-dicarboxylic acids such as glycidyl acrylate and glycidyl methacrylate, or monoethylenically unsaturated ethers of C3-C10-epoxyalkanols, especially allyl- or methallyl ethers, e.g. allyl glycidyl ether and methb18 monoethylenically unsaturated monomers having at least one carbonate group, especially a cyclic carbonate group, e.g. a 1,3-dioxolan-2-one group or 4-methyl-1,3-dioxolan-2-one group, for example propylene carbonate acrylate ([1,3-dioxolan-2-on-4-yl]methyl acrylate) or propylene carbonate methacrylate ([1,3-dioxolan-2-on-4-yl]methyl methacrylate);b19 esters of monoethylenically unsaturated C3-C8-monocarboxylic acids or monoethylenically unsaturated C4-C8-dicarboxylic acids with C8-C24-alkenols or C8-C24-alkanedienols, especially the esters of acrylic acid or of methacrylic acid, for example oleyl acrylate, oleyl methacrylate, linolyl acrylate or linolyl methacrylate. Preferred comonomers b are the monomers of groups b1, b2, b4, b5, b6, b8, b9, b10, b12 and b13, especially the monomers of groups b9, such as preferably vinylaromatic hydrocarbons, specifically styrene, and b10, preferably esters of acrylic acid or methacrylic acid with C1-C20-alcohols, and combinations of monomers b1, b2, b4, b5, b6, b8, b9, b10, b12 and b13, especially b9 and/or b10, with one or more monomers of group b17, b18 or b19.If the monomers of the formula I are copolymerized, the comonomers are preferably one or more comonomers selected from the monomers of groups b9 and b10, such as preferably vinylaromatic hydrocarbons, specifically styrene, and esters of acrylic acid or methacrylic acid with C1-C20-alcohols, such as n-butyl acrylate, 2-ethylhexyl acrylate, methyl acrylate and methyl methacrylate.If the inventive polymer comprises at least one comonomer b, preferably a comonomer of groups b9 and b10, in copolymerized form, the monomers M to be polymerized comprise generally 1 to 99% by weight, particularly 5 to 95% by weight and especially 10 to 90% by weight of at least one compound of the formula I, and 1 to 99% by weight, particularly 5 to 95% by weight and especially 10 to 90% by weight of at least one, preferably monoethylenically unsaturated, comonomer b, where the figures in % by weight are based on the total amount of monomers M. Accordingly, the repeat units of the formula I″ account for 1 to 99% by weight, particularly 5 to 95% by weight and especially 10 to 90% by weight, and the repeat units derived from the comonomers b for 1 to 99% by weight, particularly 5 to 95% by weight and especially 10 to 90% by weight, based on the total weight of all repeat units.If the monomers of the formula I are copolymerized with a comonomer of group b9, such as a vinylaromatic hydrocarbon, for example styrene, and a comonomer of group b10, such as an ester of acrylic acid or methacrylic acid with a C1-C20-alcohol, for example methyl acrylate, methyl methacrylate, n-butyl acrylate or 2-ethylhexyl acrylate, the monomers of group b9 to be polymerized are used generally in an amount of 10 to 80% by weight, especially 20 to 60% by weight, and the monomers of group b10 to be polymerized in an amount of 10 to 80% by weight, especially 20 to 60% by weight, the figures in % by weight being based on the total amount of monomers M. In that case, the monomers of the formula I account for preferably 10 to 80% by weight, especially 20 to 60% by weight, based on the total amount of monomers M. More particularly, in that case, the comonomers of groups b9 and b10 are used in a ratio of comonomers of group b9 to comonomers of group b10 of 10:1 to 1:10, especially 5:1 to 1:5.If the monomers of the formula I are copolymerized with a comonomer of group b10, such as an ester of acrylic acid or methacrylic acid with a C1-C20-alcohol, for example methyl acrylate, methyl methacrylate, n-butyl acrylate or 2-ethylhexyl acrylate, the monomers of group b10 to be polymerized are generally used in an amount of 10 to 95% by weight, preferably 20 to 90% by weight, and the monomers of the formula I in an amount of 5 to 90% by weight, preferably 10 to 80% by weight, based on the total amount of monomers M.In a preferred embodiment, the comonomers b comprise at least 60% by weight, preferably at least 80% by weight, especially at least 90% by weight, based on the total amount of the comonomers b, of at least one hydrophobic monomer having a water solubility of not more than 80 g/l at 25° C. Examples of hydrophobic monomers b are the comonomers of groups b9 to b16, and among these preferably the comonomers of groups b9, b10, b12, b13 and b14.In a further embodiment, the comonomers b comprise 60 to 99.99% by weight, preferably 80 to 99.95% by weight, especially 90 to 99.9% by weight, based on the total amount of the comonomers b, of at least one hydrophobic monomer having a water solubility of not more than 80 g/l at 25° C., and 0.01 to 40% by weight, especially 0.05 to 20% by weight or 0.1 to 10% by weight, based on the total amount of comonomers b, of at least one hydrophilic monomer having a water solubility of more than 80 g/l at 25° C. Examples of hydrophobic monomers b are the comonomers of groups b9 to b17 and b19, and among these preferably the comonomers of groups b9, b10, b12, b13 and b14. Examples of hydrophilic monomers b are the comonomers of groups b1 to b8 and b18, and among these preferably the comonomers of groups b1, b2, b4, b5, b6 and b8.It may also be appropriate that the monomers M, as well as the monomers of the formula I and optionally the comonomer(s) b, comprise one or more polyethylenically unsaturated monomers having, for example, 2, 3 or 4 nonconjugated ethylenically unsaturated double bonds, which are also referred to hereinafter as monomers c. Examples of monomers c are diesters and triesters of ethylenically unsaturated carboxylic acids, especially the bis- and trisacrylates of diols or polyols having 3 or more OH groups, for example the bisacrylates and the bismethacrylates of ethylene glycol, diethylene glycol, triethylene glycol, neopentyl glycol or polyethylene glycol. Such monomers c are, if desired, generally used in an amount of 0.01 to 10% by weight, based on the total amount of monomers M to be polymerized.The inventive polymers generally have a number-average molecular weight in the range from 1000 to 106 g/mol, especially in the range from 1200 to 105 g/mol. The weight-average molecular weight of the inventive polymers is frequently in the range from 1200 to 5×106 g/mol, especially in the range from 2000 to 2×106 g/mol.The polymerization of the monomers M can be conducted by customary methods of free-radical polymerization. These include solution and precipitation polymerization, suspension polymerization and emulsion polymerization, including a miniemulsion polymerization.In a preferred embodiment of the invention, the polymerization process is effected in a nonaqueous solvent or diluent as the polymerization medium. In other words, the polymerization is conducted in a solvent or diluent in the manner of a solution or precipitation polymerization, said solvent or diluent comprising only small amounts of water, if any. Based on the total volume of the polymerization mixture, the amount of water is frequently not more than 2% by weight, particularly not more than 1% by weight and especially not more than 0.5% by weight. Typically, the amount of water, based on the monomer, is not more than 10% by weight, frequently not more than 5% by weight, particularly not more than 2% by weight and especially not more than 1% by weight.Suitable solvents or diluents are especially those in which the monomers M to be polymerized are soluble. It is also possible to polymerize in organic solvents in which the monomers to be polymerized are insoluble. The polymerization is then effected as an oil-in-oil emulsion or suspension polymerization, in which case, depending on the ratios of monomers and organic solvent, the monomers form the coherent phase or preferably the disperse phase.Suitable solvents comprise especially aprotic solvents. These include aliphatic and cycloaliphatic hydrocarbons and halohydrocarbons, such as n-hexane, n-heptane, cyclohexane, dichloromethane, 1,2-dichloroethane, aromatic hydrocarbons and aromatic halohydrocarbons such as benzene, toluene, xylenes, chlorobenzene, dichlorobenzenes, anhydrides of aliphatic, nonpolymerizable carboxylic acids such as acetic anhydride, C1-C6-alkyl esters and C5-C6-cycloalkyl esters of aliphatic monocarboxylic acids having 1 to 4 carbon atoms, such as methyl acetate, ethyl acetate, propyl acetate, n-butyl acetate, methyl butyrate, ethyl butyrate, propyl butyrate, methyl propionate, ethyl propionate, propyl propionate, ethyl formate, butyl formate, cyclohexyl acetate and the like, C1-C4-alkoxy-C2-C4-alkyl alkanoates such as 1-methoxy-2-propyl acetate or 2-methoxyethyl acetate, N,N-di-C1-C4-alkylamides of aliphatic C1-C4-carboxylic acids, such as N,N-dimethylformamide, N,N-dimethylacetamide, N—C1-C4-alkyllactams such as N-methylpyrrolidone, N-ethylpyrrolidone, di-C1-C4-alkyl sulfoxides such as dimethyl sulfoxide, alicyclic and cyclic ketones having 3 to 8 carbon atoms, such as methyl ethyl ketone, acetone and cyclohexanone, di-C1-C4-alkyl ethers and aliphatic, cycloaliphatic and aromatic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, tetrahydrofuran, monoglyme and anisole, and also cyclic and acyclic saturated carbonates having preferably 3 to 8 carbon atoms, such as ethylene carbonate (1,3-dioxolan-2-one) and propylene carbonate, C1-C4-dialkyl carbonates such as dimethyl carbonate, diethyl carbonate, dipropyl carbonate, dibutyl carbonate and mixtures of the aforementioned aprotic solvents. Suitable solvents for the polymerization are also protic solvents and mixtures thereof with one or more aprotic solvents. These include particularly aliphatic alcohols such as C2-C4-alkylene glycol mono-C1-C4-alkyl ethers such as 1-methoxy-2-propanol, C1-C4-alkyl C2-C4-alkylene glycol mono-C1-C4-alkyl ethers such as 1-methoxy-2-methyl-2-propanol, C1-C10-alkanols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, 2-butanol, isobutanol, tert-butanol, amyl alcohol, isoamyl alcohol and mixtures of the aforementioned protic solvents.Preferred solvents are C1-C6-alkyl esters of aliphatic C1-C4-monocarboxylic acids such as n-butyl acetate, C2-C4-alkylene glycol mono-C1-C4-alkyl ethers such as 1-methoxy-2-propanol, C1-C4-alkyl C2-C4-alkylene glycol mono-C1-C4-alkyl ethers such as 1-methoxy-2-methyl-2-propanol, C1-C4-dialkyl carbonates such as dimethyl carbonate, diethyl carbonate, dipropyl carbonate, dibutyl carbonate, cyclic carbonates such as ethylene carbonate and propylene carbonate, ethers such as glymes and anisole.In the case of precipitation polymerization, the solvent or diluent is an organic solvent or diluent in which the copolymer is insoluble. In the case of solution polymerization, the solvent is an organic solvent in which the copolymer is soluble.In general, the organic solvent will be such that the amount of monomers M to be polymerized, based on the total amount of monomers M plus solvent, is in the range from 10 to 65% by weight, especially in the range from 20 to 60% by weight. In the case of a solution polymerization, accordingly, polymer solutions with solids contents in the range from 10 to 90% by weight and especially 20 to 80% by weight are obtained.The monomers M can be polymerized by customary methods of free-radical homo- or copolymerization. In general, for this purpose, the monomers M will be polymerized under reaction conditions under which free radicals form.The free radicals are generally formed by using what is called a polymerization initiator, i.e. a compound which forms free radicals on decomposition, which can be triggered chemically, thermally or photochemically.The suitable polymerization initiators include organic azo compounds, organic peroxides and hydroperoxides, inorganic peroxides and what are called redox initiators. The organic peroxide compounds include, for example, tert-butyl peroxy-2-ethylhexanoate, tert-butyl peroxypivalate, acetyl peroxide, benzoyl peroxide, lauroyl peroxide, tert-butyl peroxyisobutyrate, caproyl peroxide. The hydroperoxides include, as well as hydrogen peroxide, also organic hydroperoxides such as cumene hydroperoxide, tert-butyl hydroperoxide, tert-amyl hydroperoxide and the like. The azo compounds include, for example, 2,2′-azobisisobutyronitrile, 2,2′-azobis(2-methylbutyronitrile), 2,2′-azobis[2-methyl-N-(2-hydroxyethyl)propionamide], 1,1′-azobis(1-cyclohexanecarbonitrile), 2,2′-azobis(2,4-dimethylvaleronitrile), 2,2′-azobis(N,N′-dimethyleneisobutyramidine) 2,2′-azobis(N,N′-dimethylene-isobutyramidine), 2,2′-azobis(2-methylpropionamidine), N-(3-hydroxy-1,1-bis(hydroxymethyl)propyl)-2-[1-(3-hydroxy-1,1-bis-(hydroxymethyl)propylcarbamoyl)-1-methylethylazo]-2-methylpropionamide and N-(1-ethyl-3-hydroxypropyl)-2-[1-(1-ethyl-3-hydroxypropylcarbamoyl)-1-methylethylazo]-2-methylpropionamide. The inorganic peroxides include peroxodisulfuric acid and salts thereof, such as ammonium peroxodisulfate, sodium peroxodisulfate and potassium peroxodisulfate. Redox initiator systems are understood to mean initiator systems which comprise an oxidizing agent, for example a salt of peroxodisulfuric acid, hydrogen peroxide, or an organic peroxide such as tert-butyl hydroperoxide, and a reducing agent. As reducing agents, they preferably comprise a sulfur compound, which is especially selected from sodium hydrogensulfite, sodium hydroxymethanesulfinate and the hydrogensulfite adduct onto acetone. Further suitable reducing agents are phosphorus compounds such as phosphorous acid, hypophosphites and phosphinates, and hydrazine or hydrazine hydrate and ascorbic acid. In addition, redox initiator systems may comprise an addition of small amounts of redox metal salts, such as iron salts, vanadium salts, copper salts, chromium salts or manganese salts, for example the ascorbic acid/iron(II) sulfate/sodium peroxodisulfate redox initiator system. Particularly preferred initiators for the polymerization process according to the invention are azo compounds, especially azobisisobutyronitrile (AIBN).For free-radical polymerization of the monomers M, these polymerization initiators are used generally in an amount of 0.01 to 5% by weight, especially in an amount of 0.1 to 3% by weight, based on the monomers to be polymerized.For polymerization, the customary polymerization techniques can be employed. Particular mention should be made here of a (semi)batchwise process in which the majority, i.e. at least 60% by weight, especially at least 80% by weight and frequently the total amount of the monomers M to be polymerized is initially charged in the polymerization vessel, and the monomer feed process, in which the majority of the monomers M to be polymerized, frequently at least 60% by weight, particularly at least 80% by weight and especially at least 90% by weight, is added to the polymerization vessel in the course of the polymerization reaction. For reasons of practicability, in the case of relatively large batches, the polymerization is frequently performed as a monomer feed process.The polymerization initiator can be initially charged in the polymerization vessel or added in the course of the polymerization reaction. The procedure will frequently be to add at least a portion of the initiator, preferably at least 50% by weight and especially at least 80% by weight of the polymerization initiator, over the course of the polymerization reaction.More particularly, it has been found to be useful to initially charge a small portion of the monomers M, for example 0.1 to 20% by weight, based on the total amount of monomers M to be polymerized, optionally together with a portion or the entirety of polymerization initiator and a portion or the entirety of the solvent or diluent, in the polymerization vessel, to start the polymerization, for example by heating the polymerization mixture, and then to add the remainder of the monomers M and, if required, the remainder of polymerization initiator and solvent over the course of the polymerization.The polymerization temperatures typically employed for the polymerization are, depending on the initiator system selected, generally in the range from 20 to 180° C., particularly in the range from 40 to 130° C. and especially in the range from 50 to 120° C.The polymerization pressure is of minor importance and may be in the region of standard pressure or slightly reduced pressure, for example &800 mbar, or elevated pressure, for example up to 10 bar, though higher or lower pressures can likewise be employed.The polymerization time will generally not exceed 10 hours and is frequently in the range from 1 to 8 hours.The polymerization process according to the invention can be performed in the reactors customary for a free-radical polymerization, for example stirred tanks, especially those with close-clearance stirrers, including stirred tank cascades, and tubular reactors, which may optionally have dynamic and/or static mixing elements. The reactors generally have one or more devices for supply of the reactants and devices for withdrawal of the products, and optionally means for supplying and for removing the heat of reaction, and optionally means for controlling and/or monitoring the reaction parameters of pressure, temperature, conversion etc. The reactors can be operated batchwise or continuously.After the polymerization has ended, the polymerization mixture can be worked up in a customary manner. In the case of a precipitation polymerization, the polymer can, for example, be filtered off. Volatile components, for example solvents, can also be removed by distillative measures. In the case of a solution polymerization, it is also possible to bring about a precipitation of the polymer obtained, for example by adding an organic solvent in which the polymer is insoluble. Optionally, the polymerization may also be followed by a solvent exchange, for example in order to convert the polymer from a solution to a dispersion. Optionally, the polymer obtained will be subjected to devolatization, in order to remove further volatile constituents.The inventive polymers are suitable as a component in 2K binder compositions. 2K binder compositions are understood to mean a binder comprising at least two polyfunctional binder constituents which react with one another to form bonds and in doing so form a polymeric network. Due to the alkylidene-1,3-dioxolan-2-one groups present therein, the inventive polymers can react with numerous nucleophilic groups to form bonds. Examples of such nucleophilic groups are particularly aliphatic hydroxyl groups, aliphatic primary and secondary amino groups, phosphine groups, especially aliphatic phosphine groups, phosphonate groups, especially aliphatic phosphonate groups, and analogous phosphorus compounds, and also mercaptan groups, especially aliphatic mercaptan groups.Accordingly, 2K binder compositions comprise, as well as at least one inventive polymer, generally additionally at least one compound having at least two functional groups F, for example 2, 3, 4, 5, 6, 7, 8, 9 or 10 functional groups F, which are selected from aliphatic hydroxyl groups, aliphatic primary or secondary amino groups, aliphatic phosphine, phosphonate and similar groups, and aliphatic mercaptan groups. These compounds are also referred to hereinafter as hardeners.In general, the amount of hardener is selected such that the molar ratio of functional alkylidene-1,3-dioxolan-2-one groups of the formula I′ to the functional groups F in the hardener is in the range from 1:10 to 10:1, particularly in the range from 5:1 to 1:5 and especially in the range from 1:2 to 2:1.Preferred functional groups F are aliphatic hydroxyl groups and aliphatic primary and secondary amino groups.The hardener may be a low molecular weight substance, which means that the molecular weight thereof is below 500 g/mol, or an oligomeric or polymeric substance having a number-average molecular weight above 500 g/mol.The 2K binder compositions may also comprise one or more suitable catalysts for curing, which are guided in a known manner by the nature of the reactive functional groups F. The catalysts are, if desired, used in proportions of 0.01% by weight to about 10% by weight, based on the total weight of the inventive polymers having functional groups of the formula I′ and of the hardener. In one configuration, no catalysts are required, particularly in the case of hardeners which have amino groups as functional groups, which means that the content of catalysts in the composition is then less than 0.01% by weight. Catalysts are preferably used when the hardener has reactive groups F other than amino groups, especially when the hardener has hydroxyl groups.Catalysts used with preference are basic catalysts, more preferably organic amines and organic phosphines. Among the organic amines, preference is given to amidine bases, for example 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), and to mono-C1-C6-alkyl-, di-C1-C6-alkyl- and tri-C1-C6-alkylamines, especially triethylamine and tert-butylamine. Among the organic phosphines, preference is given to trialkylphosphines and triarylphosphines, for example tri-n-butylphosphine and triphenylphosphine. The catalysts can of course also be used as mixtures, optionally in combination with tri-C1-C6-alkylammonium halides and copper salts, for example triphenylphosphine in combination with a tri-C1-C6-alkylammonium halide and a copper salt, e.g. copper(I) chloride, copper(I) bromide, copper(II) chloride or copper(II) sulfate.The hardeners preferred in accordance with the invention include aminic hardeners, i.e. hardeners which have at least two primary or secondary amino groups, and alcoholic hardeners, i.e. compounds which have at least two hydroxyl groups.The aminic hardeners, also amine hardeners hereinafter, include, for example, aliphatic and cycloaliphatic polyamines, aromatic and araliphatic polyamines and polymeric amines, for example amino resins and polyamidoamines. Amine hardeners crosslink polymers having 1,3-dioxolan-2-one groups, also called carbonate polymers hereinafter, by reaction of the primary or secondary amino functions of the polyamines with the 1,3-dioxolan-2-one groups of the carbonate polymers to form urethane functions. Preferred polyamine hardeners have an average of at least two primary or secondary amino groups per molecule, for example two, three or four primary or secondary amino groups per molecule. They may also additionally comprise one or more tertiary amino groups. Suitable polyamines are, for example,
aliphatic polyamines such as ethylenediamine, 1,2- and 1,3-propanediamine, neopentanediamine, hexamethylenediamine, octamethylenediamine, 1,10-diaminodecane, 1,12-diaminododecane, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, 2,2-dimethylpropylenediamine, trimethylhexamethylenediamine, 1-(3-aminopropyl)-3-aminopropane, 1,3-bis(3-aminopropyl)propane, 4-ethyl-4-methylamino-1-octylamine,cycloaliphatic diamines, such as 1,2-diaminocyclohexane, 1,2-, 1,3-, 1,4-bis(aminomethyl)cyclohexane, 1-methyl-2,4-diaminocyclohexane, N-cyclohexylpropylene-1,3-diamine, 4-(2-aminopropan-2-yl)-1-methylcyclohexane-1-amine, isophoronediamine, 4,4′-diaminodicyclohexylmethane (Dicykan), 3,3′-dimethyl-4,4′-diaminodicyclohexylmethane, 3,3′,5,5′-tetramethyl-4,4′-diaminodicyclohexylmethane, 4,8-diaminotricyclo[5.2.1.0]decane, norbornanediamine, menthanediamine, menthenediamine,aromatic diamines, such as tolylenediamine, xylylenediamine, especially meta-xylylenediamine (MXDA), bis(4-aminophenyl)methane (MDA or methylenedianiline), bis(4-aminophenyl)sulfone (also known as DADS, DDS or dapsone),cyclic polyamines, such as piperazine, N-aminoethylpiperazine,polyetheramines, especially difunctional and trifunctional primary polyetheramines based on polypropylene glycol, polyethylene glycol, polybutylene oxide, poly(1,4-butanediol), polytetrahydrofuran (polyTHF) or polypentylene oxide, for example 4,7,10-trioxamidecane-1,3-diamine, 4,7,10-trioxamidecane-1,13-diamine, 1,8-diamino-3,6-dioxaoctane (XTJ-504 from Huntsman), 1,10-diamino-4,7-dioxadecane (XTJ-590 from Huntsman), 1,12-diamino-4,9-dioxadodecane (from BASF SE), 1,3-diamino-4,7,10-trioxamidecane (from BASF SE), primary polyetheramines based on polypropylene glycol having an average molar mass of 230, for example polyetheramine D 230 (from BASF SE) or Jeffamine(R) D 230 (from Huntsman), difunctional, primary polyetheramines based on polypropylene glycol having an average molar mass of 400, e.g. polyetheramine D 400 (from BASF SE) or Jeffamine(R) XTJ 582 (from Huntsman), difunctional, primary polyetheramines based on polypropylene glycol having an average molar mass of 2000, for example polyetheramine D 2000 (from BASF SE), Jeffamine(R) D2000 or Jeffamine(R) XTJ 578 (each from Huntsman), difunctional, primary polyetheramines based on propylene oxide having an average molar mass of 4000, for example polyetheramine D 4000 (from BASF SE), trifunctional, primary polyetheramines prepared by reacting propylene oxide with trimethylolpropane followed by an amination of the terminal OH groups, having an average molar mass of 403, for example polyetheramine T 403 (from BASF SE) or Jeffamine(R) T 403 (from Huntsman), trifunctional, primary polyetheramine prepared by reacting propylene oxide with glycerol, followed by an amination of the terminal OH groups, having an average molar mass of 5000, for example polyetheramine T 5000 (from BASF SE) or Jeffamine(R) T 5000 (from Huntsman), aliphatic polyetheramines formed from a propylene oxide-grafted polyethylene glycol and having an average molar mass of 600, for example Jeffamine(R) ED-600 or Jeffamine(R) XTJ 501 (each from Huntsman), aliphatic polyetheramines formed from a propylene oxide-grafted polyethylene glycol and having an average molar mass of 900, for example Jeffamine(R) ED-900 (from Huntsman), aliphatic polyetheramines formed from a propylene oxide-grafted polyethylene glycol and having an average molar mass of 2000, for example Jeffamine(R) ED-2003 (from Huntsman), difunctional, primary polyetheramine prepared by amination of a propylene oxide-grafted diethylene glycol, having an average molar mass of 220, for example Jeffamine(R) HK-511 (from Huntsman), aliphatic polyetheramines based on a copolymer of poly(tetramethylene ether glycol) and polypropylene glycol having an average molar mass of 1000, for example Jeffamine(R) XTJ-542 (from Huntsman), aliphatic polyetheramines based on a copolymer of poly(tetramethylene ether glycol) and polypropylene glycol having an average molar mass of 1900, for example Jeffamine(R) XTJ-548 (from Huntsman), aliphatic polyetheramines based on a copolymer of poly(te}