Hydrophilic, soft and oxygen permeable copolymer composition

• US 4,182,822 A
• Filed: 11/08/1976
• Issued: 01/08/1980
• Est. Priority Date: 11/08/1976
• Status: Expired due to Term

• Current Assignee: Sing-Hsiung Chang
• Original Assignee: Sing-Hsiung Chang
• Inventors: Chang, Sing-Hsiung
• Primary Examiner(s): Lilling, Herbert J.
• Application Number:
  US05/740,128
• Time in Patent Office: 1,156 Days
• Field of Search: 526/279, 526/264, 526/262
• US Class Current: 526/264
• CPC Class Codes: C08F 220/14 Methyl esters , e.g. methyl (meth)acrylate
• CPC Class Codes: C08F 220/56 Acrylamide; Methacrylamide
• CPC Class Codes: C08F 226/06 by a heterocyclic ring containing nitrogen
• CPC Class Codes: C08F 230/08 containing silicon
• CPC Class Codes: C08L 39/00 Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 43/04 Homopolymers or copolymers of monomers containing silicon
• CPC Class Codes: G02B 1/04 made of organic materials, e.g. plastics G02B1/08 takes precedence
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

A new composition of matter specially adapted for the production of contact lenses, artificial eyes or other prosthetic devices. The composition has the characteristics of increased hydrophilicity, softness after hydration and oxygen permeability. The composition is a solid copolymer of comonomers consisting essentially of about 15 to 65 parts by weight of one or more of the amide group containing monomers and about 10 to 85 parts by weight of one or more of the polysiloxanylalkyl ester of acrylate or methacrylate. Optionally, 0 to 75 parts by weight of at least one of the property modifier vinyl monomers such as methyl methacrylate, ethylacrylate, etc., can be employed into the copolymers. The inventive material is optionally transparent, translucent or opaque depending on the type, composition and relative content of the comonomers. In general, the transparent composition is suitable for use in making contact lenses.

Claims

1. A composition of matter having the characteristics of increased hydrophilicity, softness after hydration and oxygen permeability, said composition being a copolymer of comonomers consisting essentially of:

(a) about 15 to 65 parts by weight of at least one of the amide group containing monomers consisting of;

(1) N-vinyl pyrrolidone having the structure ##STR12## wherein R₁, R₂ and R₃, which may be the same or different. are selected from a class consisting of hydrogen and C₁ -C₄ alkyl groups; and

(2) acrylamide and methacrylamide having the structure ##STR13## wherein R₄ is selected from a class consisting of a methyl group and hydrogen;

R₅ and R₆, which may be the same or different, are selected from a class consisting of hydrogen and C₁ -C₄ alkyl groups, wherein the selection both of R₅ and R₆ from hydrogen is excluded; and

(b) about 10 to 85 parts by weight of at least one of a polysiloxanylalkyl ester having the structure;

##STR14## wherein X and Y, which may be the same or different, are selected from a class consisting of C₁ -C₄ alkyl groups, phenyl groups and a Z group having the structure;

##STR15## wherein A, B, C, A'"'"', B'"'"' and C'"'"', which may be the same or different, are selected from a class consisting of C₁ -C₄ alkyl groups and phenyl groups;

R is selected from a class consisting of a methyl group and hydrogen;

m and m'"'"', which may be the same or different, are integers from one to four, and n is an integer from one to three.

2. The composition of claim 1 being especially adapted for use as a prosthetic device.

3. The composition of claim 2, wherein said X and Y are selected from a class consisting of a methyl group, phenyl groups and a Z group;

said A, B, C, A'"'"', B'"'"' and C'"'"' are selected from a class consisting of a methyl group and phenyl groups.

4. The composition of claim 2, wherein said X and Y are selected from a class consisting of a methyl group and a Z group;

said A, B, C, A'"'"', B'"'"' and C'"'"' are selected from a class consisting of a methyl group.

5. The composition of claim 4, wherein said hydrophilic vinyl pyrrolidone monomers are selected from a class consisting of a 1-vinyl pyrrolidone.

6. The composition of claim 5, wherein said X and Y are a Z group;

m and m'"'"' are integers from one to two.

7. The composition of claim 6, wherein there is about 20 to 45 parts by weight of 1-vinyl pyrrolidone and about 20 to 55 parts by weight of at least one of a polysiloxanylalkyl ester.

8. A composition of matter having the characteristics of increased hydrophilicity, softness after hydration and oxygen permeability, said composition being a copolymer of comonomers consisting essentially of:

(a) about 15 to 65 parts by weight of at least one of the amide group containing monomers consisting of;

(1) N-vinyl pyrrolidone having the structure ##STR16## wherein R₁, R₂ and R₃, which may be the same or different, are selected from a class consisting of hydrogen and C₁ -C₄ alkyl groups; and

(2) acrylamide and methacrylamide having the structure ##STR17## wherein R₄ is selected from a class consisting of a methyl group and hydrogen;

R₅ and R₆, which may be the same or different, are selected from a class consisting of hydrogen and C₁ -C₄ alkyl groups, wherein the selection both of R₅ and R₆ from hydrogen is excluded; and

(b) about 10 to 85 parts by weight of at least one of a polysiloxanylalkyl ester having the structure;

##STR18## wherein X and Y, which may be the same or different, are selected from a class consisting of C₁ -C₄ alkyl groups, phenyl groups and a Z group having the structure;

##STR19## wherein A, B, C, A'"'"', B'"'"' and C'"'"', which may be the same or different, are selected from a class consisting of C₁ -C₄ alkyl groups and phenyl groups;

R is selected from a class consisting of a methyl group and hydrogen;

m and m'"'"', which may be the same or different, are integers from one to four, and n is an integer from one to three; and

(c) 0 to about 75 parts by weight of at least one of an ester of a C₁ -C₂₀ monohydric alkanol and an acid selected from a class consisting of acrylic and methacrylic acids.

9. The composition of claim 8 being especially adapted for use as a prosthetic device.

10. The composition of claim 9, wherein said X and Y are selected from a class consisting of a methyl group, phenyl groups and a Z group;

said A, B, C, A'"'"', B'"'"' and C'"'"' are selected from a class consisting of a methyl group and phenyl groups.

11. The composition of claim 9, wherein said X and Y are selected from a class consisting of a methyl group and a Z group;

said A, B, C, A'"'"', B'"'"' and C'"'"' are selected from a class consisting of a methyl group.

12. The composition of claim 11, wherein said hydrophilic vinyl pyrrolidone monomers are selected from a class consisting of a 1-vinyl pyrrolidone.

13. The composition of claim 12, wherein said X and Y are a Z group;

m and m'"'"' are integers from one to two.

14. A composition of matter specially adapted for use as a prosthetic device having the characteristics of increased hydrophilicity, softness after hydration and oxygen permeability, said composition being a copolymer of comonomers consisting essentially of:

(a) about 20 to 45 parts by weight of at least one of the amide group containing monomers consisting of N-vinyl pyrrolidone and N,N-dimethyl methacrylamide;

(b) about 20 to 55 parts by weight of at least one of a polysiloxanyl ester having the structure;

##STR20## wherein X and Y, which may be the same or different, are selected from a class consisting of a methyl group and a Z group having the structure;

##STR21## wherein R is selected from a class consisting of a methyl group and hydrogen;

m and m'"'"', which may be the same or different, are integers from one to two, and n is an integer from one to three; and

(c) 0 to about 30 parts by weight of at least one of an ester of a C₁ -C₂₀ monohydric alkanol and an acid selected from a class consisting of acrylic and methacrylic acids.