Silicon-containing (meth) acrylate compounds

Patent metadata

Field	Value
Publication number	US-9695331-B2
Application number	US-201313859100-A
Country	US
Kind code	B2
Filing date	Apr 9, 2013
Priority date	Apr 10, 2012
Publication date	Jul 4, 2017
Grant date	Jul 4, 2017

Abstract

The present invention includes silicon-containing (meth)acrylate compounds of formula (I):

where A is a C 1 -C 12 organic moiety such as an alkyl or aryl moiety, B is a silane functional group, C is a (meth)acrylate functional group and D is an allyl functional group, with w=0 or 1, z=0, 1 or 2, x=1, 2 or 3, y=1, 2 or 3 and w+x+y+z=4. The compounds are suitable for use in curable compositions, such as peroxide-curable compositions or radiation-curable compositions and may be applied to a substrate as a coating or sealant, for example. Compositions containing the silicon-containing (meth)acrylate compounds may have reduced volatility and odor problems along with improved adhesion to substrates, increased crosslink density and/or improved hardness.

First claim

The invention claimed is:

1. A compound or a mixture of compounds of formula (I):

wherein
A is a C 1 -C 12 organic moiety,
B is a silane functional group with formula —CH 2 O(R 2 ) m (CH 2 ) 3 SiX 3 where X=a halogen, a C 1 -C 6 alkyl, a C 1 -C 6 alkoxy or an aromatic radical,
C is a (meth)acrylate functional group with formula CH 2 O(R 2 ) m (C═O)C(R 1 )═CH 2 where R 1 is H or CH 3 ,
D is an allyl functional group with formula —CH 2 O(R 2 ) m CH 2 C(H)═CH 2 , and w=0 or 1, x=2 or 3, y=1 or 2, and z=0, 1 or 2, and w−x+y+z=4,

where R 2 for each functional group is the same or different and is an oxyalkylene or polyoxyalkylene unit comprised of n repeating units of oxyalkylene, a caprolactone or polycaprolactone unit comprised of n repeating units of formula —[C(═O) (CH 2 ) 5 O]— or a lactide or polylactide unit, comprised of n repeating units of formula —[C(═O)CH(CH 3 )O]—, n is an integer with a value from 1 to 12 and m is 0 or 1.

2. A compound according to claim 1 , wherein z=0 or 1, w=1, A is a C 1 or C 2 alkyl group, R 1 is CH 3 or H, m=0 and X is methoxy or ethoxy.

3. A compound according to claim 1 , wherein z=0 or 1, w=1, A is a C 1 or C 2 alkyl group, R 1 is CH 3 or H, m=1, n=1 to 5, where R 2 is an oxyalkylene or polyoxyalkylene unit and X is methoxy or ethoxy.

4. A compound according to claim 1 , wherein z=0 or 1, w=0, R 1 is CH 3 or H, m=0 and X is methoxy or ethoxy.

5. A compound according to claim 1 , wherein z=0 or 1, w=0, R 1 is CH 3 or H, m=1, n=1 to 5, R 2 is an oxyalkylene or polyoxyalkylene unit and X is methoxy or ethoxy.

6. A compound according to claim 1 , wherein R 2 is an oxyalkylene or polyoxyalkylene unit of formula —[CH 2 CH 2 O] n — or —[CH 2 CH(CH 3 )O] n — where n is an integer with a value from 1 to 12.

7. A compound according to claim 1 , wherein the compound is derived from the reaction of (meth)acrylate esters of mono- or di-allyl ethers of trimethylol propane with trimethoxy silane or triethoxy silane.

8. A compound according to claim 1 , wherein the compound is derived from the reaction of (meth)acrylate esters of mono- or di-allyl ethers of ethoxylated or propoxylated trimethylol propane with trimethoxy silane or triethoxy silane.

9. A compound according to claim 1 , wherein the compound is derived from the reaction of (meth)acrylate esters of mono-, di- or tri-allyl ethers of pentaerythritol with trimethoxy silane or triethoxy silane.

10. A compound according to claim 1 , wherein the compound is obtained by the reaction of (meth)acrylate esters of mono-, di- or tri-allyl ethers of ethoxylated or propoxylated pentaerythritol with trimethoxy silane or triethoxy silane.

11. A curable composition, wherein the curable composition comprises at least one compound as defined according to claim 1 .

12. A curable composition according to claim 11 , wherein said curable composition is or comprises, a peroxide-curable or a radiation-curable composition which is a free radical-curable, a cationic-curable or a dual-curable free radical and cationic hybrid curable composition.

13. A curable composition according to claim 12 , wherein said curable composition is a peroxide-curable coating, adhesive, elastomer, rubber, concrete, composite or sealant composition.

14. A curable composition according to claim 12 , wherein said curable composition is a radiation curable coating, adhesive or sealant composition.

15. A substrate coated with a curable composition as defined according to claim 11 .

16. A substrate according to claim 15 , wherein said substrate is selected from the group consisting of glass, metal, steel, wood, plastic, composite, cardboard, plaster and concrete.

17. A method of making a compound according to claim 1 , comprising reacting a silane compound of formula (II)
H—Si(X) 3   (II)

on at least one allyl functionality of the precursor compound of formula (II):

where:
A is a C 1 -C 12 organic moiety,
C is a (meth)acrylate functional group with formula —CH 2 O(R 2 ) m (C═O)C(R 1 )═CH 2 where R 1 is H or CH 3 ,
D is an allyl functional group with formula —CH 2 O(R 2 ) m CH 2 C(H)═CH 2 , and w=0 or 1, y=1, 2 or 3 and z=1, 2 or 3 and w+y+z=4, where R 2 for each functional group is the same or different and is an oxyalkylene or polyoxyalkylene unit comprised of n repeating units of oxyalkylene such as oxyethylene [CH 2 CH 2 O] or oxypropylene [CH 2 CH(CH 3 )O], a caprolactone or polycaprolactone unit, comprised of n repeating units of formula —[C(═O) (CH 2 ) 5 O]— or a lactide or polylactide unit, comprised of n repeating units of formula —[C(═O)CH(CH 3 )O]—, n being an integer with a value from 1 to 12 and m is 0 or 1

in the presence of a transition metal catalyst.

Assignees

• Arkema France

Inventors

• Horgan James P
• Klang Jeffrey A
• He Yuhong
• Goodrich James

Classifications

• C09D143/04

  Homopolymers or copolymers of monomers containing silicon · CPC title

• C07F7/1836

  Chemistry & Metallurgy · mapped topic

• C09D133/14 Primary

  of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen · CPC title

• C08L2312/08

  by silane · CPC title

• Y10T428/31663

  As siloxane, silicone or silane · CPC title