Silicone-based hydrophilic copolymer and hydrogel compositions comprising the same

• US 9,851,472 B2
• Filed: 03/27/2015
• Issued: 12/26/2017
• Est. Priority Date: 03/27/2015
• Status: Active Grant

• Current Assignee: Momentive Performance Materials Incorporated
• Original Assignee: Momentive Performance Materials Incorporated
• Inventors: Naik, Sandeep, Bhat, Shreedhar, Shah, Chetan, Saxena, Anubhav, Mathad, Raveendra
• Primary Examiner(s): ZIMMER, MARC S
• Application Number:
  US14/670,557
• Publication Number:
  US 20160282517A1
• Time in Patent Office: 1,005 Days
• Field of Search: 526279
• CPC Class Codes: A61K 8/90 Block copolymers A61K8/89 takes precedence
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• 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 220/325 containing glycidyl radical, e.g. glycidyl (meth)acrylate
• CPC Class Codes: C08F 220/54 Amides , e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
• CPC Class Codes: C08F 220/56 Acrylamide; Methacrylamide
• CPC Class Codes: C08F 230/08 containing silicon
• CPC Class Codes: C08F 261/02 on to polymers of unsaturated alcohols
• CPC Class Codes: C08F 275/00 Macromolecular compounds obtained by polymerising monomers on to polymers of monomers containing phosphorus, selenium, tellurium or a metal as defined in group C08F30/00
• CPC Class Codes: C08L 101/14 the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
• CPC Class Codes: C08L 33/10 Homopolymers or copolymers of methacrylic acid esters
• CPC Class Codes: C08L 33/26 Homopolymers or copolymers of acrylamide or methacrylamide
• 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 hydrophilic siloxane copolymer of siloxane and hydrophilic organic monomer/s The copolymers can be functionalized to make them capable of undergoing further polymerization by thermal or actinic radiations. The hydrophilicity of these polymers can be varied by varying the siloxane versus organic monomer ratio thereby going from water dispersible to soluble states. The siloxane content can be tuned accordingly in order to provide moderate to high oxygen permeability. These copolymers can be used as a single component curable composition which results in hydrogels to minimize the presence of leachable components thus by reducing the processing cost. The polymers may also find applications in personal care formulations as copolymers, film-formers, hydrogels, coating, emulsions/latex etc.

Claims

1. A hydrophilic siloxane copolymer of the formula (1):

[W_lA_mB_nC]_p 

 

(1)

wherein A and B are different, l is 1, m and n of formula (1) are independently 1-200, and 2<

l+p<

200;

W is a moiety having the general formula (2);

D-E----- 

 

(2)

wherein E is a divalent moiety chosen from a substituted, un-substituted, aliphatic, aromatic, cyclic, or acyclic hydrocarbon radical having 1-20 carbon atoms, optionally containing sulfur or oxygen;

D is a monovalent hydrocarbon radical with 1-10 carbon atoms with a functional group independently selected from a hydroxy, an ether, an ester, an amine, an amide, a carboxylic acid, or a combination of two or more thereof;

A is an organosilicone group-containing unit having the general formula (15);

2. The copolymer of claim 1 wherein H in formula (16) has a formula (17a):

3. The copolymer of claim 1 wherein H in formula (16) has a formula (8a):

4. The copolymer of claim 1, wherein the ratio of m:

n;

p is from about 5-60;

20-80;

5-60, with the proviso that the total of the ratio adds up to 100.

5. A composition comprising a hydrophilic siloxane copolymer of the formula (1):

[W_lA_mB_nC]_p 

 

(1)

wherein A and B are different, l is 1, m and n in formula (1) are independently 1-200, and 2<

l+p<

200;

W is a moiety having the general formula (2);

D-E------ 

 

(2)

wherein E is a divalent moiety chosen from substituted, un-substituted, aliphatic, aromatic, cyclic, or acyclic hydrocarbon radical having 1-20 carbon atoms, optionally containing sulfur or oxygen;

D is a monovalent hydrocarbon radical with 1-10 carbon atoms with a functional group independently selected from a hydroxy, an ether, an ester, an amine, an amide, a carboxylic acid, or a combination of two or more thereof;

A is an organosilicone group-containing unit having the general formula (15);

6. The composition of claim 5 wherein H in formula (16) has a formula (17a):

7. The composition of claim 5 wherein H in formula (16) has a formula (8a):

8. The composition of claim 5, wherein the ratio of m:

n;

p is from about 5-60;

20-80;

5-60, with the proviso that the total of the ratio adds up to 100.

9. The composition of claim 5, wherein the composition further comprises a cure initiator;

optionally a monomer chosen from a vinylic monomer, an acrylamide monomer, an acrylic monomer, or a combination of two or more thereof; and

optionally a cross-linker.

10. The composition of claim 9, wherein the vinylic monomer is chosen from N-vinyl-pyrrolidone (NVP), N-vinyl-caprolactam, N-vinyl-acetamide, N-vinyl-formamide and N-vinyl-isopropylamide, vinyl benzene, vinyl naphthalene, vinyl pyridine, vinyl alcohol, vinyl containing silicones, or a combination of two or more thereof;

the acrylic monomers are 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 (DMA), N-isopropylacrylamide, acrylamide, methacrylamide, acrylic acid, methacrylic acid, any acrylated hydrophilic or hydrophobic organo-silicones present in the art, or combinations of two or more thereof.

11. The composition of claim 9, wherein the initiator is 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 and Darocur and Irgacure types.

12. The composition of claim 9, wherein the cross-linker is chosen from ethylene glycol dimethacrylate and trimethyloylpropane trimethacrylate, diethyleneglycol dimethacrylate, bisphenol A dimethacrylate, diglycidyl bisphenol A dimethacrylate and dimethacrylate-terminated polyethylene glycol and reactive linear polyether modified silicones.

13. The composition of claim 5, wherein the composition is a hydrogel.

14. A contact lens comprising the hydrogel of claim 13.

15. An article comprising a coating formed from the composition of claim 5, wherein the coating is disposed on at least a portion of a surface of the article.

16. A process for forming a contact lens comprising forming a film from the composition of claim 5 into a contact lens;

and removing any leachable monomers from contact lens.

17. The process of claim 16, wherein removing the leachable monomers comprises treating the contact lens with an aqueous systems.

18. The process of claim 16 wherein the process comprises treating the contact lens with water, an organic salt solution, an inorganic salt solutions, a buffer, an emulsion, an ophthalmically compatible solvent in the temperature range of 20-125°

C. for extraction, or a combination of two or more thereof.