Organosilicon compounds having (meth)acrylate groups and a process for preparation thereof

Patent metadata

Field	Value
Publication number	US-10329313-B2
Application number	US-201615742457-A
Country	US
Kind code	B2
Filing date	Aug 9, 2016
Priority date	Sep 4, 2015
Publication date	Jun 25, 2019
Grant date	Jun 25, 2019

Abstract

(Meth)acrylate-functionalized silicon compounds are easily prepared by the reaction of a (meth)acryloyl-functionalized chlorosilane with an organosilicon compound having silicon-bonded hydroxy groups. The carbon atom adjacent to the resulting O—Si linkage is bonded to at least one further carbon, rendering the product stable to hydrolysis despite the C—O—Si linkage.

First claim

What is claimed is:

1. A composition comprising a (meth)acrylate-functional organosilicon compound M in which an oxygen atom connects a (meth)acrylate group to a silicon of the organosilicon compound, wherein the carbon atom bonded to the oxygen atom bears at least one further moiety bonded via carbon, with the proviso that in the presence of just one further moiety, said moiety contains more than one carbon atom, comprising at least one unit of formula I and at least one unit of formula II
R 2 b X c SiO [4−(b+c)]/2   (I),

R 1 a SiO (4−a)/2   (II),

where
R 1 and R 2 are each independently hydrogen or C 1 -C 20 hydrocarbon or C 1 -C 15 hydrocarbonoxy moieties in which one or more nonadjacent methylene units are optionally replaced by —O—, —CO—, —COO—, —OCO— or —OCOO or NR x groups, and which are unsubstituted, or substituted with a substituent —CN, NR x 2 , COOH, COOR x , -halogen, -acryloyl, -methacryloyl, -epoxy, —OH, or —CONR x 2 ,
R x is hydrogen or a C 1 -C 10 hydrocarbon moiety unsubstituted or substituted with a substituent —CN or halogen,
X is an oxygen-bonded moiety of formula (III)
O—C(R 3 R 4 )—R 5 —O—(C═O)—CR 6 ═CH 2 )  (III)

R 3 and R 4 are each independently hydrogen or C 1 -C 20 hydrocarbon moieties in which one or more nonadjacent methylene units are optionally replaced by O—(C═O)—CR 6 ═CH 2 , —O—, —CO—, —COO—, —OCO— or —OCOO— or NR x groups, with the proviso that when R 3 is hydrogen, R 4 contains at least two carbon atoms,
R 5 is a divalent C 1 -C 20 hydrocarbon moiety in which one or more nonadjacent methylene units are optionally replaced by —O—, —CO—, —COO—, —OCO— or —OCOO— or NR x groups,
R 6 is hydrogen or unbranched, branched or cyclic saturated or unsaturated alkyl of 1 to 12 carbon atoms or aryl or aralkyl, wherein nonadjacent methylene units may be replaced by nitrogen atoms or oxygen atoms,
a is 0, 1, 2 or 3,
b is 0, 1 or 2,
c is 1, 2 or 3, and
b+c is 1, 2 or 3.

2. The (meth)acrylate-functional organosilicon compound M of claim 1 , wherein R 1 and R 2 are each straight-chain, branched or cyclic C 1 -C 6 alkyl or alkoxy moieties, or phenyl or vinyl moieties.

3. The (meth)acrylate-functional organosilicon compound M of claim 2 , wherein R 3 and R 4 are each independently selected from methyl, ethyl and (meth)acryloyloxymethyl.

4. The (meth)acrylate-functional organosilicon compound M of claim 3 , wherein R 5 is a divalent C-bonded C 1 -C 6 hydrocarbon moiety wherein nonadjacent methylene groups are optionally replaced by oxygen.

5. The (meth)acrylate-functional organosilicon compound M of claim 2 , wherein R 5 is a divalent C-bonded C 1 -C 6 hydrocarbon moiety wherein nonadjacent methylene groups are optionally replaced by oxygen.

6. The (meth)acrylate-functional organosilicon compound M of claim 1 , wherein R 3 and R 4 are each independently selected from methyl, ethyl and (meth)acryloyloxymethyl.

7. The (meth)acrylate-functional organosilicon compound M of claim 6 , wherein R 5 is a divalent C-bonded C 1 -C 6 hydrocarbon moiety wherein nonadjacent methylene groups are optionally replaced by oxygen.

8. The (meth)acrylate-functional organosilicon compound M of claim 1 , wherein R 5 is a divalent C-bonded C 1 -C 6 hydrocarbon moiety wherein nonadjacent methylene groups are optionally replaced by oxygen.

9. A process for preparing a (meth)acrylate-functionalized organosilicon compounds M of claim 1 , constructed of at least one unit of formula I and no or at least one unit of general formula II
R 2 b X c SiO [4−(b+c)]/2   (I),

R 1 a SiO (4−a)/2   (II),

comprising:
reacting a (meth)acryloyl-functionalized chlorosilane of formula IV
R 2 b X c SiCl [4−(b+c)]   (IV)

with a hydroxyl-functionalized organosilicon compounds.

10. A process for preparing a (meth)acrylate-functionalized chlorosilanes of formula IV of claim 9 ,
R 2 b X c SiCl [4−(b+c)]   (IV),

comprising:
reacting a (meth)acryloyl-functionalized alcohol of formula V
HO—C(R 3 R 4 )—R 5 —O—(C═O)—CR 6 ═CH 2   (V)

with a chlorosilane of formula VI
R 2 b SiCl [4−b]   (VI).

11. A (meth)acryloyl-functionalized chlorosilane of formula IV
R 2 b X c SiCl [4−(b+c)]   (IV).

Assignees

• Wacker Chemie Ag

Inventors

• Fritz-Langhals Elke

Classifications

• C08G77/20

  containing silicon bound to unsaturated aliphatic groups · CPC title

• C08G77/00

  Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule · CPC title

• C07F7/123

  by reactions involving the formation of Si-halogen linkages · CPC title

• C07F7/12 Primary

  Organo silicon halides · CPC title

• C07F7/1804 Primary

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title