Hydrophilic silicone composition

• US 9,296,764 B2
• Filed: 12/10/2013
• Issued: 03/29/2016
• Est. Priority Date: 12/10/2013
• Status: Active Grant

• Current Assignee: Momentive Performance Materials Incorporated (Momentive Performance Materials Holdings LLC)
• Original Assignee: Momentive Performance Materials Incorporated (Momentive Performance Materials Holdings LLC)
• Inventors: Bhat, Shreedhar, Saxena, Anubhav, Lewis, Kenrick M., Naik, Sandeep
• Primary Examiner(s): PENG, KUO LIANG
• Application Number:
  US14/102,025
• Publication Number:
  US 20150158889A1
• Time in Patent Office: 840 Days
• US Class Current: 1/1
• CPC Class Codes: C07F 7/0838 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 Class Codes: C08F 230/08 containing silicon
• CPC Class Codes: C08G 77/20 containing silicon bound to unsaturated aliphatic groups C08G77/045 takes precedence
• CPC Class Codes: C08L 43/04 Homopolymers or copolymers of monomers containing silicon
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

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.

Claims

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

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

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

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

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

6. The composition of claim 1, wherein R¹ is a divalent radical having a structure of Formula (5):

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, —

NR₂, —

PO(OR)₂, —

OPO(OR)₂, —

OSO₃H, —

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 —

NR₂, —

OPO(OR)₂, —

OSO₃H, or —

OH groups.

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

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

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

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

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

13. The composition of claim 1, wherein the composition is a copolymer comprising the organosilicon compound.

14. The composition of claim 13, wherein the copolymer is reactive or non-reactive.

15. The composition of claim 14, wherein the copolymer is a prepolymer.

16. The composition of claim 15, wherein the prepolymer is monofunctional or multifunctional.

17. The composition of claim 16, wherein the prepolymer is a (meth)acrylated reaction product of (1) the organosilicon compound, (2) a chain transfer agent, (3) one or more organic monomers, and (4) a radical initiator.

18. The composition of claim 17, wherein the chain transfer agent is chosen from 2-mercapto ethanol, 2-aminoethyl mercaptans, alkane thiols, thioglycolic acid and esters, bromotricloromethane, 3-mercaptopropionic acid and esters, isooctyl 3-mercaptopropionate, Pentaerythritol tetrakis(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptopropionate), trimethylolpropane tris(3-mercaptopropionate), 4,4′

-thiobisbenzenethiol, iodonitriles, etc.

19. The composition of claim 1, wherein the composition is a hydrogel.

20. The composition of claim 19, further comprising a free-radical polymerizable organic monomer, an initiator, and optionally a crosslinker.

21. The composition of claim 20, wherein the free-radical polymerizable organic monomer is chosen from a vinylic monomer, an acrylide monomer, an acrylic monomer, or a combination of two or more thereof.

22. The composition of claim 21, wherein the vinylic monomer is chosen from N-vinyl-pyrrolidone, N-vinyl-caprolactam, N-vinyl-acetamide, N-vinyl-formamide, N-vinyl-isopropylamide, vinyl benzene, vinyl naphthalene, vinyl pyridine, vinyl alcohol, vinyl containing silicone, or a combination of two or more thereof.

23. The composition of claim 21, wherein the acrylic monomer is chosen from 2-hydroxy-ethyl-methacrylate (HEMA), 2-hydroxy-ethyl-acrylate (HEA), hydroxyl propyl methacrylate, trimethylammonium 2-hydroxy propyl methacrylate hydrochloride, dimethylaminoethyl methacrylate, glycerol methacrylate, N,N-dimethylacrylamide, N-isopropylacrylamide, acrylamide, methacrylamide, acrylic acid, methacrylic acid, acrylated hydrophilic or hydrophobic organo-silicone, or a combination of two or more thereof.

24. The composition of claim 19, wherein a hydrophilic silicone macromer is present in an amount of from about 5 weight percent to about 50 weight percent of the hydrogel composition.

25. The composition of claim 24, wherein the ratio of a hydrophilic silicone macromer to a free-radical polymerizable organic monomer is from about 1:

100 to about 100;

1.

26. The composition of claim 24, wherein the ratio of a hydrophilic silicone macromer to a free-radical polymerizable organic monomer is from about 1:

50 to about 50;

1.

27. The l composition of claim 24, wherein the ratio of a hydrophilic silicone macromer to a free-radical polymerizable organic monomer is from about 1:

10 to about 10;

1.

28. The composition of claim 24, wherein the ratio of a hydrophilic silicone macromer to a free-radical polymerizable organic monomer is about 1:

1.

29. The composition of claim 19, optionally comprising a cross-linker chosen from ethylene glycol dimethacrylate, trimethyloylpropane trimethacrylate, diethyleneglycol dimethacrylate, bisphenol A dimethacrylate, diglycidyl bisphenol A dimethacrylate, dimethacrylate-terminated polyethylene glycol, a reactive linear or pendant polyether modified silicone, or a combination of two or more thereof.

30. The composition of claim 19, wherein the composition comprises a thermal or a photo initiator chosen from 2,2′

-azobis(2,4-dimethylpentanenitrile), 2,2′

-azobis(2-methylpropanenitrile), 2,2′

-azobis(2-methylbutanenitrile), peroxides such as benzoyl peroxide, benzoin methyl ether, diethoxyacetophenone, a benzoylphosphine oxide, 2-hydroxy-2-methyl propiophenone (HMPP), 1-hydroxycyclohexyl phenyl ketone, a Darocur type, an Irgacure type, or a combination of two or more thereof.

31. A contact lens comprising a hydrogel film formed from the composition of claim 19.

32. The composition according to claim 19, wherein the composition is a film forming additive in a textile, paper, leather, personal care, health care, home care, coating, painting or seed treatment formulations.