Silicone hydrogel polymers

• US 5,962,548 A
• Filed: 03/02/1998
• Issued: 10/05/1999
• Est. Priority Date: 03/02/1998
• Status: Expired due to Term

• Current Assignee: Johnson & Johnson Vision Products, Inc.
• Original Assignee: Johnson & Johnson Vision Products, Inc.
• Inventors: Vanderlaan, Douglas G., Hargiss, Marcie
• Primary Examiner(s): Michl, Paul R.
• Application Number:
  US09/033,348
• Time in Patent Office: 582 Days
• Field of Search: 523/107, 526/279
• US Class Current: 523/107
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: C08L 83/08 containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

A silicone hydrogel polymer prepared by curing a reaction mixture comprising a hydroxyalkylamine-functional silicone-containing monomer.

Claims

1. A silicone hydrogel polymer prepared by curing a reaction mixture comprising a hydroxyalkylamine-functional silicone-containing monomer, comprising the following structure:

##STR8## wherein;

n is 0 to 500 and m is 0 to 500 and (n+m)=10 to 500;

R², R⁴, R⁵, R⁶ and R⁷ are independently a monovalent alkyl, or aryl group, which may be further substituted with alcohol, ester, amine, ketone, carboxylic acid or ether groups, and

R¹, R³ and R⁸ are independently a monovalent alkyl, or aryl group, which may be further substituted with an alcohol, ester, amine, ketone, carboxylic acid or ether group;

or have the following structure;

##STR9## with the proviso that at least one of R¹, R³, and R⁸ are according to Structure II, wherein

R⁹ is a divalent alkyl group;

R¹⁰ and R¹¹ are independently H, a monovalent alkyl or aryl group which may be further substituted with an alcohol, ester, amine, ketone, carboxylic acid or ether group, or have the following structure;

##STR10## where R¹⁴ is H, or a monovalent polymerizable group comprising acryloyl, methacryloyl, styryl, vinyl, allyl or N-vinyl lactam;

R¹⁶ is H, a monovalent alkyl or aryl group which can be further substituted with alcohol, ester, amine, ketone, carboxylic acid or ether groups, or a polymerizable group comprising acrylate, methacrylite, styryl, vinyl, allyl or N-vinyl lactam;

R¹², R¹³ and R¹⁵ are independently H, a monovalent alkyl or aryl, which can be further substituted with alcohol, ester, amine, ketone, carboxylic acid or ether groups, or R¹² and R¹⁵, or R¹⁵ and R¹³ can be bonded together to form a ring structure, with the proviso that at least one of the Structure II groups on the monomer comprise polymerizable groups.

2. The silicone hydrogel polymer of claim 1 wherein (n+m) is 20 to 250;

R², R⁴, R⁵, R⁶ and R⁷ are independently unsubstituted monovalent alkyl or aryl groups;

R⁹ is --(CH₂)_s -- where s is 1 to 10;

R¹⁴ is H or methacryloyl;

R¹⁶ is either alkyl substituted with an alcohol or methacrylate; and

R¹², R¹³ and R¹⁵ are H.

3. The silicone hydrogel polymer of claim 1 wherein R², R⁴, R⁵, R⁶, and R⁷ are independently selected from methyl, benzyl, phenyl and ethyl;

R¹ and R⁸ are both groups according to Structure II, and R³ is selected from methyl, ethyl, phenyl and benzyl.

4. The silicone hydrogel of claim 1 wherein said hydroxyalkylamine-functional silicone-containing monomer of this invention generally has between 2 to 20 nitrogen groups per molecule on average, and 2 to 5 polymerizable groups per molecule on average.

5. The silicone hydrogel of claim 1 wherein said hydroxyalkylamine-functional silicone-containing monomer has the following structure:

##STR11## wherein R², R⁴, R⁵, R⁶, and R⁷ are independently selected from methyl, benzyl, phenyl and ethyl;

R¹⁷ is defined as an alkyl group or aryl group which may be substituted with an alcohol, ester, amine, ketone, carboxylic acid or ether group, R⁹ and R¹⁸ are independently --(CH₂)_s -- where s is from 1 to 10; and

R¹⁹, R²⁰, R¹⁰ and R¹¹ are independently H, a monovalent alkyl or aryl group which may be further substituted with an alcohol, ester, amine, ketone, carboxylic acid or ether group, or has the following structure;

##STR12## where R¹⁴ is H, or a monovalent polymerizable group comprising acryloyl, methacryloyl, styryl, vinyl, allyl or N-vinyl lactam;

R¹⁶ is either H, a monovalent alkyl or aryl group which can be further substituted with alcohol, ester, amine, ketone, carboxylic acid or ether groups, or a polymerizable group comprising acrylate, methacrylate, styryl, vinyl, allyl or N-vinyl lactam;

R¹², R¹³ and R¹⁵ are independently H, a monovalent alkyl or aryl, which can be further substituted with alcohol, ester, amine, ketone, carboxylic acid or ether groups, with the proviso that at least one of the Structure II groups on the monomer comprise polymerizable groups.

6. The silicone hydrogel of claim 1 wherein said hydroxyalkylamine-functional silicone-containing monomer is selected from the group consisting of:

##STR13##

7. The silicone hydrogel of claim 1 wherein said hydroxyalkylamine-functional silicone-containing monomer is:

8. The silicone hydrogel of claim 1 wherein said reaction mixture further comprises a hydrophilic monomer.

9. The silicone hydrogel of claim 8 wherein said hydrophilic monomer is selected from the group consisting of N,N-dimethyl acrylamide, 2-hydroxyethyl methacrylate, glycerol methacrylate, 2-hydroxyethyl methacrylamide, N-vinylpyrrolidone, polyethyleneglycol monomethacrylate, methacrylic acid ard acrylic acid.

10. The silicone hydrogel of claim 1 wherein said reaction mixture further comprises an additional silicone-containing monomer.

11. The silicone hydrogel of claim 8 wherein said reaction mixture further comprises an additional silicone-containing monomer.

12. The silicone hydrogel of claim 11 wherein said additional silicone-containing monomer is a polysiloxyanylalkyl (meth)acrylic monomer.

13. The silicone hydrogel of claim 11 wherein said additional silicone-containing monomer has the structure:

wherein R⁵¹ is H or CH₃, q is 1 to 3 and for each q, R⁵², R⁵³ and R⁵⁴ are independently methyl, benzyl, phenyl or a monovalent siloxane chain comprising from 1 to 100 repeating Si--O units, p is 1 to 10, r=(3-q), X is O or NR⁵⁵, where R⁵⁵ is H or a monovalent alkyl group with 1 to 4 carbons, a is 0 or 1, and L is a divalent linking group.

14. The silicone hydrogel of claim 11 wherein said additional silicone-containing monomer is selected from the group consisting of methacryloxypropyl tris(trimethylsiloxy)silane, pentamethyldisiloxanyl methylmethacrylate, phenyltetramethyl-disiloxanylethyl acrylate, 3-methacryloxypropylbis(trimethylsiloxy)methylsilane, methacryloxypropylpentamethyldisiloxane and methyldi(trimethylsiloxy)methaceyloxymethyl silane N,N-dimethyl acrylamide.

15. The silicone hydrogel of claim 11 wherein said reaction mixture comprises hydroxyalkylamine-functional silicone-containing monomer as 10 to 60 weight percent of the reactive components, additional silicone-containing monomer as 20 to 50 weight percent of the reactive components, and hydrophilic monomer as 10 to 50 weight percent of the reactive components.

16. A soft contact lens comprising a silicone hydrogel polymer prepared by curing a reaction mixture comprising a linear or branched, block or random, hydroxyalkylamine-functional silicone-containing monomer, comprising the following structure:

##STR14## wherein;

n is 0 to 500 and m is 0 to 500 and (n+m)=10 to 500;

R², R⁴, R⁵, R⁶ and R⁷ are independently a monovalent alkyl, or aryl group, which may be further substituted with alcohol, ester, amine, ketone, carboxylic acid or ether groups, and

R¹, R³ and R⁸ are independently a monovalent alkyl, or aryl group, which may be further substituted with an alcohol, ester, amine, ketone, carboxylic acid or ether group, or have the following structure;

##STR15## with the proviso that at least one of R¹, R³, and R⁸ are according to Structure II, wherein

R⁹ is a divalent alkyl group such as --(CH₂)_s -- where s is from 1 to 10;

R¹⁰ and R¹¹ are independently H, a monovalent alkyl or aryl group which may be further substituted with an alcohol, ester, amine, ketone, carboxylic acid or ether group, or has the following structure;

##STR16## where R¹⁴, is H, or a monovalent polymerizable group comprising acryloyl, methacryloyl, styryl, vinyl, allyl or N-vinyl lactam;

R¹⁶ is either H, a monovalent alkyl or aryl group which can be further substituted with alcohol, ester, amine, ketone, carboxylic acid or ether groups, or a polymerizable group comprising acrylate, methacrylate, styryl, vinyl, allyl or N-vinyl lactam;

R¹², R¹³ and R¹⁵ are independently H, a monovalent alkyl or aryl, which can be further substituted with alcohol, ester, amine, ketone, carboxylic acid or ether groups, or R¹² and R¹⁵, or R¹⁵ and R¹³ can be bonded together to form a ring structure, with the proviso that at least some of the Structure II groups on the monomer comprise polymerizable groups.

17. The soft contact lens of claim 16 further comprising an additional silicone-containing monomer and a hydrophilic monomer.

18. The soft contact lens of claim 16 wherein said hydroxyalkylamine-functional silicone-containing monomer is:

##STR17## said additional silicone-containing monomer is 3-methacryloxypropylbis (trimethylsiloxy)methylsilane, and said hydrophilic monomer is N,N-dimethyl acrylamide.

19. The soft contact lens of claim 16 wherein said hydroxyalkylamine-functional silicone-containing monomer is:

##STR18##