Hydrophilic macromers and hydrogels comprising the same

• US 9,804,296 B2
• Filed: 09/22/2014
• Issued: 10/31/2017
• 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: Phukan, Monjit, Saxena, Anubhav, Bhat, Shreedhar
• Primary Examiner(s): Yoon, Tae H
• Application Number:
  US14/492,433
• Publication Number:
  US 20150011669A1
• Time in Patent Office: 1,135 Days
• Field of Search: 523107, 528 25, 528 32
• CPC Class Codes: C07F 7/081 comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
• 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 220/281 and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (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 222/102 of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
• CPC Class Codes: C08F 222/28 Diallyl maleate
• CPC Class Codes: C08F 222/385 Monomers containing two or more (meth)acrylamide groups, e.g. N,N'-methylenebisacrylamide
• CPC Class Codes: C08F 226/10 N-Vinyl-pyrrolidone
• CPC Class Codes: C08F 290/062 Polyethers
• CPC Class Codes: C08F 290/068 Polysiloxanes
• CPC Class Codes: C08L 101/14 the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: C09D 151/08 grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: C09J 151/08 grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: G02B 2207/109 Sols, gels, sol-gel materials

Abstract

A hydrophilic silicone macromer composition suitable for use in producing hydrogel polymer films from which biomedical devices such as contact lenses can be made. The hydrophilic silicone macromer comprises a polyether backbone comprising a silicone-containing pendant group. In one aspect, a hydrophilic silicone macromer is of the Formula 1:

The hydrophilic silicone macromer can be used to form a polymer and a hydrogel film suitable for forming contact lenses.

Claims

1. A composition comprising at least one hydrophilic silicone macromer of the Formula:

2. The composition of claim 1, wherein the hydrophilic silicone macromer has a structure according to the formula R¹(CH₂CH₂O)_a(CH(CH₃)CH₂O)_b(CH[CH₂)_1/2R²]CH₂O)_dR⁵.

3. The composition of claim 2, where R² is a group defined as M_fD_gT_hQ_iR⁶_j with M=R⁷R⁸R⁹Si(O)_1/2;

D=R¹⁰Si(O)_2/2(CH₂)_1/2;

f=2;

g=1;

h=0;

i=0;

j=1; and

R⁶=—

(CH₂)_1/2R¹³(CH₂)_1/2.

4. The composition of claim 2, where R² is a group defined as M_fD_gT_hQ_iR⁶_j with M=R⁷R⁸R⁹Si(O)_1/2;

T=Si(O)_3/2(CH₂)_1/2;

f=3;

g=0;

h=1;

i=0;

j=1; and

R⁶=—

(CH₂)_1/2R¹³(CH₂)_1/2—

.

5. The composition of claim 2, where R² is a group defined as R⁷R⁸R⁹SiO(Si(R¹⁰)(R¹¹)(O)_lSi(R⁷)(R⁸)(CH₂)_1/2;

and where 0≦

1≦

200.

6. The composition of claim 1, wherein the hydrophilic macromer has a structure according to the formula:

7. The composition of claim 1, wherein the hydrophilic macromer is of the formula:

8. The composition of claim 1, wherein the hydrophilic macromer is of the formula:

9. The composition of claim 1, wherein Y is chosen from a polymerizable group having the general structure:

10. The composition of claim 9, where the linking group B is chosen from the following functional moieties:

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

12. The composition of claim 11, wherein the hydrogel forming composition further comprises a monomer chosen from a vinylic monomer, an acrylide monomer, an acrylic monomer, or a combination of two or more thereof;

a free radical initiator; and

optionally a cross-linker.

13. The composition of claim 12, 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, a vinyl containing silicone, or a combination of two or more thereof.

14. The composition of claim 12, wherein 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, or a combination of two or more thereof.

15. The composition of claim 12, wherein the initiator can be 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 benzoin methyl ether, diethoxyacetophenone, a benzoylphosphine oxide, 2-hydroxy-2-methyl propiophenone (HMPP), 1-hydroxycyclohexyl phenyl ketone, an acylphosphine oxide, or a combination of two or more thereof.

16. The composition of claim 12, wherein the cross-linker can be selected 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, or a combination of two or more thereof.

17. A contact lens comprising the composition of claim 11.

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

C. for extraction.

19. A polymer formed from the composition according to claim 1.

20. The polymer of claim 19, wherein the polymer is a homopolymer, copolymer, free-radical polymerized emulsion, or a latex composition.

21. A composition comprising the polymer of 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 formulation.