Hydrophilic silicone composition

Patent metadata

Field	Value
Publication number	US-9296764-B2
Application number	US-201314102025-A
Country	US
Kind code	B2
Filing date	Dec 10, 2013
Priority date	Dec 10, 2013
Publication date	Mar 29, 2016
Grant date	Mar 29, 2016

Abstract

A composition comprising a carbocyclic group and a hydrophilic moiety attached thereto an alpha, beta-unsaturated organosilicon compound. Such compounds are useful in developing water absorbing silicone-hydrogel films. Silicone-hydrogel films provide increased oxygen to pass through a lens or other treated materials.

First claim

What is claimed is:

1. A composition comprising an alpha, beta-unsaturated organosilicon compound having the structure of Formula (1):

wherein:
X 1 is independently selected from linear or branched alkyl group containing 1-16 carbon atoms, trimethoxy silyl, trimethylsilyloxy, —O[Si(CH 3 ) 2 O—] n wherein n is an integer chosen from 1 to 9, (CH 3 ) 3 Si(CH 2 ) o CH 2 — wherein o is an integer from 0-3, (CH 3 ) 3 SiCH 2 CH 2 Si(CH 3 ) 2 O—, or (CH 3 ) 3 Si(CH 2 CH 2 Si(CH 3 ) 2 O) q wherein q is an integer chosen from 0-200; and, if X 1 is a monovalent radical, p is 0;
X 2 is independently selected from linear or branched alkyl group containing 1-16 carbon atoms, trimethoxy silyl, trimethylsilyloxy, —O[Si(CH 3 ) 2 O—] n wherein n is an integer chosen from 1 to 9, (CH 3 ) 3 Si(CH 2 ) o CH 2 — wherein o is an integer from 0-3, (CH 3 ) 3 SiCH 2 CH 2 Si(CH 3 ) 2 O—, or (CH 3 ) 3 Si(CH 2 CH 2 Si(CH 3 ) 2 O) q — wherein q is an integer chosen from 0-200, or —[OSi(CH 3 ) 2 ] m G 1 , wherein G 1 is (CH 3 ) 3 SiO—, or a reactive or non reactive silicone group with the general Formula (2a) or (2b):

where l is an integer chosen from 0-200; and p in Formula 1 is 0 when X 2 is of the Formula (2a), Formula (2b), or a monovalent radical;
X 6 , X 7 , and X 8 are independently chosen from a linear or branched alkyl group containing 1-16 carbon atoms, alkoxy, trimethylsilyloxy, or —O[Si(CH 3 ) 2 O—] n , wherein n is an integer chosen from 1 to 9, and wherein X 6 and X 7 , X 7 and X 8 , or X 6 and X 8 may form a ring;

X 3 and X 5 are independently chosen from methyl, butyl, trimethylsiloxy, (CH 3 ) 3 SiCH 2 CH 2 —, (CH 3 ) 3 SiCH 2 CH 2 Si(CH 3 ) 2 O— or —OSi(CH 3 ) 2 —, with the provisos that (i) when X 1 or X 6 is —O[Si(CH 3 ) 2 O—] n , then at least one of X 3 or X 5 is —OSi(CH 3 ) 2 — and X 1 forms a chemical bond with the X 3 and/or X 5 forms a chemical bond with X 6 to correspondingly form a divalent —X 1 -X 3 — or X 5 —X 6 — group, which is bonded to the silicon atom to form a cyclic polysiloxane ring, and (ii) when X 3 and/or X 5 is —O[Si(CH 3 ) 2 O—] n then X 1 and/or X 6 is —OSi(CH 3 ) 2 — and the corresponding X 1 forms a chemical bond with the X 3 and/or X 5 forms a chemical bond with X 6 to form a divalent —X 1 -X 3 — or X 5 -X 6 — group, which is bonded to the silicon atom to form a cyclic polysiloxane ring; or
X 1 , X 2 , and X 3 optionally are each —O[Si(R 16 )O 3/2 —] n and interconnected to form a polysilsequioxane ring as described in formula (2c)

wherein R 16 is independently chosen from a linear or branched alkyl or aralkyl group;
X 4 is an optional connecting group selected independently from dimethylsiloxy, —O[Si(CH 3 ) 2 O—], or —CH 2 CH 2 (CH 3 ) 2 SiO—,
p is an integer chosen from 0-5;
R 1 is chosen from a chemical bond or an alkylene group containing from 1 to 16 carbon atoms and optionally containing a heteroatom of oxygen, sulfur and/or nitrogen;
G is a bridging unit between the siloxane moiety and reactive moiety independently selected from a linear or branched alkyl group or a carbocyclic group, the G unit optionally containing one or more heteroatoms;
A is a heteroatom;
I is a hydrophilic moiety with 0-100 carbon atoms which may contain heteroatoms;
Z is a polymerizable group of Formula (3):

wherein R 6 , R 7 , and R 8 are independently selected from hydrogen or monovalent hydrocarbon radical with 1-5 carbon atoms; and
F is an optional linker group chosen from aliphatic, cycloaliphatic, or aromatic hydrocarbon radical of 1 to about 16 carbons and optionally contains heteroatoms, with the proviso that if F is not utilized, then A is directly linked to the carbonyl group in Formula (3).

2. The composition of claim 1 , wherein G is a branched alkyl moiety with the general formula (4a)

wherein a is 0-16 and b is 1.

3. The composition of claim 1 , wherein G comprises a saturated carbocyclic unit comprising 5 to 10 carbon atoms, having the general formula:

wherein c=0-5.

4. The composition of claim 3 , wherein G is chosen from a positional isomer of the formula:

or a combination of two or more thereof.

5. The composition of claim 3 , wherein G is chosen from:

or a combination of two or more thereof.

6. The composition of claim 1 , wherein R 1 is a divalent radical having a structure of Formula (5):

wherein R 3 , R 4 , and R 5 are independently selected from hydrogen, a linear, branched and/or cyclic hydrocarbon radical with 1 to 10 carbon atoms, and one or more of optionally contains heteroatoms; a R 2 is a hydrocarbon radical with 1 to 5 carbon atoms; and q is an integer chosen from 0 to 10.

7. The composition of claim 1 , wherein I is a hydrophilic moiety having a structure of Formula (6):
—K-L-M  (6)

wherein:
K is a divalent heteroatom or an oxygen;
L is chosen from a divalent hydrocarbon radical chosen from a substituted or unsubstituted, linear or branched, aliphatic or aromatic hydrocarbon comprising 50 or fewer carbon atoms, which optionally contain heteroatoms and has a functionality chosen from an alcohol, an ether, an ester, an amide, an amine, a urea, a urethane, a cyano, a carbonate, a carbamate, a thiol, a thioether, thiol ester, or a combination of two or more thereof; and
M is an ionic group chosen from —COOR, —NR 2 , —PO(OR) 2 , —OPO(OR) 2 , —OSO 3 H, —OH, where R is hydrogen or an alkyl group of from 1 to 3 carbon atoms, with the proviso that when L is a functionality that does not contain any carbon atoms then M cannot comprise any —NR 2 , —OPO(OR) 2 , —OSO 3 H, or —OH groups.

8. The composition of claim 1 , wherein F on the polymerizable group Z has a structure of the Formula (7):

wherein:
r is an integer selected from 0 to about 15;
S is a divalent heteroatom independently selected from O, CH 2 , NR 11 , and sulfur;
J is independently selected from a functional group chosen from —C(O)—, —NR 12 C(O)—, —OC(O)—, —OS(O)—, and —P(O)OR 13 —;
R 9 and R 10 are independently chosen from a hydrocarbon radical with 1 to 5 carbon atoms; and
R 11 , R 12 , and R 13 are independently selected from hydrogen or a monovalent hydrocarbon radical with 1-5 carbon atoms.

9. The composition of claim 1 , wherein the alpha, beta-unsaturated compound has a structure of the formula:

wherein:
x and y are each integers chosen from 0-100;
X is independently chosen from linear or branched alkyl group containing 1-16 carbon atoms, alkoxy, trimethoxysilyl, trimethylsilyloxy, (CH3)3Si[OSi(CH3)2] q O— wherein q is an integer chosen from 0-100;
R

Assignees

• Momentive Performance Mat Inc

Inventors

• Bhat Shreedhar
• Naik Sandeep
• Saxena Anubhav
• Lewis Kenrick M

Classifications

• C08L83/04

  Polysiloxanes · CPC title

• C08K5/0025

  Crosslinking or vulcanising agents; including accelerators · CPC title

• C08G77/20 Primary

  containing silicon bound to unsaturated aliphatic groups · CPC title

• C07F7/0838 Primary

  Compounds with one or more Si-O-Si sequences (compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21) · CPC title

• C08L43/04

  Homopolymers or copolymers of monomers containing silicon · CPC title