Silicone hydrogels comprising high levels of polyamides

Patent metadata

Field	Value
Publication number	US-10370476-B2
Application number	US-201715609079-A
Country	US
Kind code	B2
Filing date	May 31, 2017
Priority date	Jul 6, 2016
Publication date	Aug 6, 2019
Grant date	Aug 6, 2019

Abstract

Described are silicone hydrogels with high levels of polyamides exhibiting an excellent balance of physical, mechanical, and biological properties. The silicone hydrogels are formed from a reactive monomer mixture comprising: a hydroxylalkyl (meth)acrylate monomer; hydroxyl-containing silicone components; and a polyamide, wherein the polyamide is present in an amount greater than 15 weight percent, based on the total weight of reactive components in the reactive monomer mixture.

First claim

What is claimed is:

1. A silicone hydrogel formed from a reactive monomer mixture comprising:
a) at least one hydroxyalkyl (meth)acrylate monomer;
b) at least one first mono-functional hydroxyl-substituted poly(disubstituted siloxane) having 4 to 8 siloxane repeating units;
c) at least one second hydroxyl-substituted poly(disubstituted siloxane) that is a mono-functional hydroxyl-substituted poly(disubstituted siloxane) having 10 to 200 siloxane repeating units;
d) at least 15 wt % at least one polyamide, based on the total weight of reactive components in the reactive monomer mixture; and
e) optional further constituents.

2. The silicone hydrogel of claim 1 , wherein the polyamide is present in the reactive mixture in an amount between 15.1 weight percent and about 40 weight percent, based on the total weight of all reactive components in the reactive monomer mixture.

3. The silicone hydrogel of claim 1 , wherein the polyamide is selected from the group consisting of cyclic polyamides, acyclic polyamides, and mixtures thereof.

4. The silicone hydrogel of claim 3 , wherein the polyamide comprises repeating units selected from Formula I, Formula II and Formula IV

wherein
R 1 is independently a hydrogen atom or methyl;
X is a direct bond, —(CO)—, or —(CO)—NH—R e —, wherein R e is a C 1 to C 3 alkyl group;
R a is selected from H, straight or branched, substituted or unsubstituted C 1 to C 4 alkyl groups;
R b is selected from H, straight or branched, substituted or unsubstituted C 1 to C 4 alkyl groups, amino groups having up to two carbon atoms, amide groups having up to four carbon atoms, and alkoxy groups having up to two carbon groups;
R c is selected from H, straight or branched, substituted or unsubstituted C 1 to C 4 alkyl groups;
R d is selected from H, straight or branched, substituted or unsubstituted C 1 to C 4 alkyl groups;
wherein the number of carbon atoms in R a and R b taken together is 8 or less, and wherein the number of carbon atoms in R c and R d taken together is 8 or less.

5. The silicone hydrogel of claim 4 , wherein the number of carbon atoms in R a and R b taken together is 6 or less.

6. The silicone hydrogel of claim 3 , wherein the cyclic polyamide is prepared from at least one of α-lactam, β-lactam, γ-lactam, δ-lactam, and ε-lactam.

7. The silicone hydrogel of claim 3 , wherein the cyclic polyamide comprises repeating units of Formula IV

wherein
R 1 is independently a hydrogen atom or methyl; f is a number from 1 to 10, and
X is a direct bond, —(CO)—, or —(CO)—NH—R e —, wherein R e is a C 1 to C 3 alkyl group.

8. The silicone hydrogel of claim 7 , wherein f is 8 or less.

9. The silicone hydrogel of claim 8 , wherein f is 6 or less.

10. The silicone hydrogel of claim 7 , wherein f is 2 to 6.

11. The silicone hydrogel of claim 10 , wherein f is 3.

12. The silicone hydrogel of claim 10 , wherein f is 2.

13. The silicone hydrogel of claim 3 , wherein the polyamide is a copolymer.

14. The silicone hydrogel of claim 1 , wherein the polyamide is selected from polyvinylpyrrolidone (PVP), polyvinylmethyacetamide (PVMA), polydimethylacrylamide (PDMA), polyvinylacetamide (PNVA), poly(hydroxyethyl(meth)acrylamide), polyacrylamide, and copolymers and mixtures thereof.

15. The silicone hydrogel of claim 14 , wherein the polyamide is PVP.

16. The silicone hydrogel of claim 14 , wherein the polyamide is PVMA.

17. The silicone hydrogel of claim 13 , wherein the copolymer comprises at least 80 mole percent of the repeating units selected from NVP, VMA, DMA, NVA, and mixtures thereof.

18. The silicone hydrogel of claim 13 , wherein the copolymer further comprises at least one repeating unit selected from the group consisting of N-vinyl amides, acrylamides, hydroxyalkyl (meth)acrylates, alkyl(meth)acrylates, N-vinylpyrrolidone, N,N-dimethylacrylamide, 2-hydroxyethyl methacrylate, vinyl acetate, acrylonitrile, hydroxypropyl methacrylate, 2-hydroxyethyl acrylate, methyl methacrylate, butyl methacrylate, methacryloxypropoyl tristrimethylsiloxysilane, siloxane substituted acrylates or methacrylates, and mixtures thereof.

19. The silicone hydrogel of claim 1 further comprising at least one additional hydrophilic monomer.

20. The silicone hydrogel of claim 1 wherein said hydroxyalkyl (meth)acrylate monomer is selected from the group consisting of 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2,3-dihydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 3-hydroxybutyl (meth)acrylate, 1-hydroxypropyl-2-(meth)acrylate, 2-hydroxy-2-methyl-propyl (meth)acrylate, 3-hydroxy-2,2-dimethyl-propyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, glycerol (meth)acrylate, polyethylene glycol monomethacrylate, and mixtures thereof.

21. The silicone hydrogel of claim 1 wherein said hydroxyalkyl (meth)acrylate monomer is selected from the group consisting of 2-hydroxyethyl methacrylate, glycerol methacrylate, 2-hydroxypropyl methacrylate, hydroxybutyl methacrylate, 3-hydroxy-2,2-dimethyl-propyl methacrylate, and mixtures thereof or 2-hydroxyethyl methacrylate, 3-hydroxy-2,2-dimethyl-propyl methacrylate, hydroxybutyl methacrylate or glycerol methacrylate and mixtures thereof.

22. The silicone hydrogel of claim 19 , wherein the additional hydrophilic monomer is selected from the group consisting of ethylene glycol vinyl ether (EGVE), di(ethylene glycol) vinyl ether (DEGVE), N-vinyl pyrrolidone (NVP), 1-methyl-3-methylene-2-pyrrolidone, 1-methyl-5-methylene-2-pyrrolidone, 5-methyl-3-methylene-2-pyrrolidone; 1-ethyl-5-methylene-2-pyrrolidone, N-methyl-3-methylene-2-pyrrolidone, 5-ethyl-3-methylene-2-pyrrolidone, 1-n-propyl-3-methylene-2-pyrrolidone, 1-n-propyl-5-methylene-2-pyrrolidone, 1-isopropyl-3-methylene-2-pyrrolidone, 1-isopropyl-5-methylene-2-pyrrolidone, N-vinyl-N-methyl acetamide (VMA), N-vinyl-N-ethyl acetamide, N-vinyl-N-ethyl formamide, N-vinyl formamide, N-vinyl acetamide, N-vinyl isopropylamide, allyl alcohol, N-vinyl caprolactam, N-2-hydroxyethyl vinyl carbamate, N-carboxy-ß-alanine N-vinyl ester; N-carboxyvinyl-β-alanine (VINAL), N-carboxyvinyl-α-alanine and mixtures thereof.

23. The silicone hydrogel of claim 19 , wherein the additional hydrophilic monomer is selected from N,N-dimethylacrylamide, N-vinylpyrrolidone, N-vinyl-N-methyl acetamide, N-vinyl acetamide, and 1-methyl-5-methylene-2-pyrrolidone.

24. The silicone hydrogel of claim 19 , wherein the additional hydrophilic monomer comprises N-vinylpyrrolidone, N,N-dimethylacrylamide, and mixtures thereof.

25. The silicone hydrogel of claim 1 , wherein the first mono-functional hydroxyl-substituted poly(disubstituted siloxane) and the second hydroxyl-substituted poly(disubstituted siloxane) are present in the reactive monomer mixture in concentrations that provide a weight ratio, of the first mono-functional hydroxyl-substituted poly(disubstituted siloxane) to the second hydroxyl-substituted poly(disubstituted siloxane) of between 0.1 to 1.3.

26. The silicone hydrogel of claim 1 , wherein the first mono-functional hydroxyl-substituted poly(disubstituted siloxane) has the

Assignees

• Johnson & Johnson Vision Care

Inventors

• Alli Azaam
• Guzman Alexander

Classifications

• C08L39/06

  Homopolymers or copolymers of N-vinyl-pyrrolidones · CPC title

• C08L83/10

  Block- or graft-copolymers containing polysiloxane sequences (obtained by polymerising a compound having a carbon-to-carbon double bond on to a polysiloxane C08L51/08, C08L53/00) · CPC title

• C08L2203/02

  for biomedical use · CPC title

• C08J2383/04

  Polysiloxanes · CPC title

• C08L51/085

  on to polysiloxanes · CPC title