Hydrophilic silicone monomers, process for preparation thereof and thin films containing the same

• US 9,459,378 B2
• Filed: 09/22/2014
• Issued: 10/04/2016
• Est. Priority Date: 03/22/2012
• 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: Saxena, Anubhav, Bhat, Shreedhar, Umapathy, Senthilkumar, Lewis, Kenrick M.
• Primary Examiner(s): NAZARIO GONZALEZ, PORFIRIO
• Application Number:
  US14/492,489
• Publication Number:
  US 20150011661A1
• Time in Patent Office: 743 Days
• Field of Search: 514/785, 514/788, 510/466, 522/64, 524/547, 523/107, 252/182.14, 252/183.11
• US Class Current: 1/1
• CPC Class Codes: A61K 2800/10 General cosmetic use
• CPC Class Codes: A61K 8/8158 Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
• CPC Class Codes: A61K 8/898 containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: A61Q 5/02 Preparations for cleaning the hair
• CPC Class Codes: C08F 220/20 of polyhydric alcohols or phenols , e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
• CPC Class Codes: C08F 220/54 Amides , e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
• CPC Class Codes: C08F 222/102 of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
• CPC Class Codes: C08F 226/10 N-Vinyl-pyrrolidone
• 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: C08G 77/388 containing nitrogen
• CPC Class Codes: C08G 77/46 containing polyether sequences
• CPC Class Codes: C08L 101/14 the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
• CPC Class Codes: C08L 33/24 Homopolymers or copolymers of amides or imides
• CPC Class Codes: C08L 83/12 containing polyether sequences
• CPC Class Codes: C09D 143/04 Homopolymers or copolymers of monomers containing silicon
• CPC Class Codes: D06M 15/643 containing silicon in the main chain
• CPC Class Codes: D06M 15/6436 containing amino groups
• CPC Class Codes: D06M 2200/50 Modified hand or grip properties; Softening compositions
• CPC Class Codes: D21H 17/59 : obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon
• CPC Class Codes: G02B 1/043 : Contact lenses

Abstract

The present invention relates to a fast curing compositions comprising a (meth)acrylamide functionalized hydrophilic silicone monomers having a polyether moiety containing a branched linking group. In one embodiment, such compositions are useful for preparing water-absorbing silicone-hydrogel films for contact lens applications. In one embodiment, the (meth)acrylamide monomers disclosed here have a branched linking group on the polyether moiety which makes it possible to produce hydrophilic polyether modified silicone copolymers without the need to separate various by-products including, but not limited to, unreacted, isomerized polyether and associated high molecular weight by-products.

Claims

1. A hydrogel composition comprising at least one silicone acrylamide monomer, the silicone acrylamide monomer having a formula as set forth in Formulas (I) or (II) below:

2. The hydrogel composition of claim 1, wherein the silicone acrylamide monomer comprises (a) a reaction of (i) silicone-containing compound having Formula (V):

R₃Si—

O—

[SiH(R)]_a—

[OSiR₂]_b—

OSiR₃ 

 

(V)

wherein a is 1 to 50;

b is 0 to 100;

each R is independently selected from the group consisting of a monovalent aliphatic, cycloaliphatic, or aromatic hydrocarbon group of 1 to about 10 carbons, and halogenated hydrocarbon groups of 1 to about 10 carbons;

with (ii) a polyether having at least one end terminated with hydroxyl, a halogen, or an epoxy, and the other end terminated with a branched alkene having Formula (VI);

CH₂═

CHR^b—

CH₂)_n—

(OC₂H₄(OC₃H₆)_q—

(OC₄H₈)_r—

Y 

 

(VI)

wherein n is 1 to about 20, p and q are 0 to about 100;

r is 0 to about 50;

Rb is an alkyl group having from 1 to about 4 carbon atoms, Y is —

OH, a halogen, an epoxy or an amine, the reaction of (i) and (ii) being conducted in the presence of a catalyst to produce a polyether siloxane, and (b) reacting the polyether siloxane with an acryl compound having Formula (VII);

3. The hydrogel composition of claim 2, wherein L is a moiety having Formula:

4. The hydrogel composition of claim 1, comprising the silicone acrylamide monomer is of the formula:

5. The hydrogel composition of claim 1, comprising the silicone acrylamide monomer of the formula:

6. The hydrogel composition of claim 1, comprising the silicone acrylamide monomer of the formula:

7. The hydrogel composition of claim 1, comprising the silicone acrylamide monomer of the formula:

8. The hydrogel of claim 1, wherein the co-monomer is chosen from a silicone-containing monomer, an organic based monomer, or a combination of two or more thereof.

9. The hydrogel of claim 1, wherein the hydrogel further comprises a co-monomer chosen from a vinylic monomer, an allylic monomer, an acrylide monomer, an acrylic monomer, or a combination of two or more thereof.

10. The hydrogel of claim 8, 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, a vinyl containing silicones, or a combination of two or more thereof.

11. The hydrogel of claim 8, wherein the vinyl, allyl, or acrylide, or acrylic monomer is chosen from 3-[Tris(trimethylsiloxy)silyl]propyl methacrylate;

methyl-di(trimethylsiloxy)-silyl propyl glycerol methacrylate;

3-(trimethylsilyl)propyl vinyl carbonate;

3-(vinyloxycarbonylthio)propyl-[tris(trimethylsiloxy)silane];

3-[tris(tri-methylsiloxy)silyl]propyl vinyl carbamate;

3-[tris(trimethylsiloxy)silyl]propyl allyl carbamate;

3-[tris(trimethylsiloxy)silyl]propyl vinyl carbonate, or a combination of two or more thereof.

12. The hydrogel of claim 8, wherein the acrylic organic 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-dimethyl acrylamide, N-isopropylacrylamide, acrylamide, methacrylamide, acrylic acid, methacrylic acid, an acrylated hydrophilic or hydrophobic organo-silicone, or a combination of two or more thereof.

13. The hydrogel of claim 1, further 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.

14. The hydrogel composition of claim 1, wherein the composition further 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), benzoyl peroxide, benzoin methyl ether, diethoxyacetophenone, a benzoylphosphine oxide, 2-hydroxy-2-methyl propiophenone (HMPP), 1-hydroxycyclohexyl phenyl ketone, a Darocur-type initiator, an Irgacure-type initiator or a combination of two or more thereof.

15. The hydrogel composition of claim 1, wherein, the hydrogel composition cures to a self-standing film in time of about 10 seconds or less using 365 nm light with an intensity of 105 mW/cm².

16. A contact lens comprising the hydrogel film of claim 1.

17. The contact lens according to claim 16 comprising a limited extraction protocol that further comprises a green or aqueous solvents chosen from water, an organic or inorganic salt solutions, a buffer, an emulsion, a commercial lens cleaning solution, or an ophthalmically compatible solvent in the temperature range of 15-125°

C. for extraction.

18. The composition according of claim 1, 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.

19. The hydrogel composition of claim 4, wherein p is from 2 to 15.

20. The hydrogel composition of claim 5, wherein p is from 2 to 15.

21. The hydrogel composition of claim 6, wherein p is from 2 to 15.

22. The hydrogel composition of claim 7, wherein p is from 2 to 15.