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