Polymerizable alkylidene-1,3-dioxolane-2-one and use thereof

Patent metadata

Field	Value
Publication number	US-9062136-B2
Application number	US-201313853552-A
Country	US
Kind code	B2
Filing date	Mar 29, 2013
Priority date	Mar 29, 2012
Publication date	Jun 23, 2015
Grant date	Jun 23, 2015

Abstract

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.

First claim

The invention claimed is:

1. A compound of formula I

wherein
R 1 and R 2 are each independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 5 -C 6 -cycloalkyl, phenyl or phenyl-C 1 -C 4 -alkyl;
R 3 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 5 -C 6 -cycloalkyl, phenyl or phenyl-C 1 -C 4 -alkyl;
R 4 is hydrogen, C 1 -C 4 -alkyl, CH 2 COOR 8 , phenyl or phenyl-C 1 -C 4 -alkyl;
R 5 and R 6 are each independently hydrogen or C 1 -C 4 -alkyl, or one of R 5 and R 6 may also be COOR 8 or CH 2 COOR 8 ;
A is a chemical bond or C 1 -C 4 -alkanediyl;
X is O or NR 7 ;
Z is a chemical bond, PO 2 , SO 2 or C═O;
Y is a chemical bond, CH 2 or CHCH 3 ;
R 7 , if present, is C 1 -C 6 -alkyl; and
R 8 , if present, is hydrogen or C 1 -C 6 -alkyl.

2. The compound according to claim 1 , wherein R 1 and R 2 are each independently hydrogen or C 1 -C 6 -alkyl.

3. The compound according to claim 1 , wherein R 3 is hydrogen.

4. The compound according to claim 1 , wherein A is ethanediyl.

5. The compound according to claim 1 , wherein X is O.

6. The compound according to claim 1 , wherein Z is C═O.

7. The compound according to claim 1 , wherein Y is a chemical bond.

8. 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 displaceable leaving group; and
L′ is hydrogen or a C 1 -C 4 -alkylcarbonyl group.

9. The process according to claim 8 ,
wherein
L is OH or C 1 -C 8 -alkoxy,
Z is CO═, X is O, and
the reacting is performed under conditions of an esterification or transesterification.

10. 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
R 1 and R 2 are each independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 5 -C 6 -cycloalkyl, phenyl or phenyl-C 1 -C 4 -alkyl;
R 3 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 5 -C 6 -cycloalkyl, phenyl or phenyl-C 1 -C 4 -alkyl;
A is a chemical bond or C 1 -C 4 -alkanediyl;
X is O or NR 7 ;

Z is a chemical bond, PO, SO 2 or C═O;
Y is a chemical bond, CH 2 or CHCH 3 ; and
R 7 , if present, is C 1 -C 6 -alkyl.

11. 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 .

12. The polymer according to claim 10 , in a form of a homopolymer of a compound of formula I.

13. 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.

14. The polymer according to claim 13 , wherein the comonomer b is at least one selected from the group consisting of
monoethylenically unsaturated C 3 -C 8 -monocarboxylic acid, monoethylenically unsaturated C 4 -C 8 -dicarboxylic acid,
amides an amide of monoethylenically unsaturated C 3 -C 8 -mono- or C 4 -C 8 -dicarboxylic acids,
an anhydride of monoethylenically unsaturated C 4 -C 8 -dicarboxylic acids,
a hydroxy-C 2 -C 4 -alkyl ester of monoethylenically unsaturated C 3 -C 8 -mono- or C 4 -C 8 -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-C 2 -C 4 -alkylene oxide group,
a vinylaromatic hydrocarbon,
esters an ester of monoethylenically unsaturated C 3 -C 8 -monocarboxylic acids with C 1 -C 20 -alkanols, C 5 -C 6 -cycloalkanols, phenyl-C 1 -C 4 -alkanols or phenoxy-C 1 -C 4 -alkanols,
a diester of monoethylenically unsaturated C 4 -C 8 -dicarboxylic acids with C 1 -C 20 -alkanols, C 5 -C 8 -cycloalkanols, phenyl-C 1 -C 4 -alkanols or phenoxy-C 1 -C 4 -alkanols,
a C 1 -C 20 -alkylamide of monoethylenically unsaturated C 3 -C 8 -monocarboxylic acids, a di-C 1 -C 10 -alkylamide of monoethylenically unsaturated C 3 -C 8 -monocarboxylic acids,
a vinyl ester of aliphatic carboxylic acids having 1 to 20 carbon atoms,
a conjugatedly diethylenically unsaturated C 4 -C 10 -olefin,
a C 2 -C 20 -olefin,
a halogen-substituted C 2 -C 20 -olefin,
a monoethylenically unsaturated monomer having one or two epoxide groups,
a monoethylenically unsaturated monomer having a carbonate group,
an ester of monoethylenically unsaturated C 3 -C 8 -monocarboxylic acids with C 8 -C 24 -alkenols or C 8 -C 24 -alkanedienols and an ester of monoethylenically unsaturated dicarboxylic acids with C 8 -C 24 -alkenols or C 8 -C 24 -alkane-dienols.

15. The polymer according to claim 13 , further comprising, in copolymerized form, a comonomer c having 2, 3 or 4 nonconjugated, ethylenically unsaturated double bonds.

16. The polymer according to claim 10 , wherein the polymer is a component in 2K binder compositions.

17. 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.

18. 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.

19. The compound according to claim 1 , wherein R 1 and R 2 are each independently hydrogen or methyl.

Assignees

• Basf Se

Inventors

• Porta Garcia Marta
• Weis Martine
• Lanver Andreas
• Blanchot Mathieu
• Flores-Figueroa Aaron
• Klopsch Rainer
• Haaf Christina
• Kutzki Olaf

Classifications

• C08F220/40

  Esters of unsaturated alcohols {, e.g. allyl (meth)acrylate} · CPC title

• C08F24/00 Primary

  Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a heterocyclic ring containing oxygen (cyclic esters of polyfunctional acids C08F18/00; cyclic anhydrides of unsaturated acids C08F20/00, C08F22/00) · CPC title

• C08F222/10

  Esters · CPC title

• C08F220/18

  with acrylic or methacrylic acids · CPC title

• C08F220/1808 Primary

  C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate · CPC title