Hydrophilic, soft and oxygen permeable copolymer compositions

• US 4,343,927 A
• Filed: 07/17/1978
• Issued: 08/10/1982
• 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): Bleutge, John C.
• Assistant Examiner(s): Lilling, Herbert J.
• Application Number:
  US05/925,640
• Time in Patent Office: 1,485 Days
• Field of Search: 526/262, 526/264, 526/265, 526/279, 526/303
• US Class Current: 526/262
• CPC Class Codes: C08F 226/06 by a heterocyclic ring containing nitrogen
• CPC Class Codes: C08F 226/10 N-Vinyl-pyrrolidone
• CPC Class Codes: C08F 230/08 containing silicon
• CPC Class Codes: C08F 283/124 on to polysiloxanes having carbon-to-carbon double bonds
• 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: C08L 51/085 on to polysiloxanes
• 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 about 65% by weight of one or more of the hydrophilic amide group containing monomers and about 10 to about 75% by weight of one or more of the polysiloxanylalkyl methacrylates or acrylates. Optionally, about 0.1 to about 65% by weight of at least one property modifier, a vinyl group containing monomer such as methyl methacrylate, 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 used. In general, the transparent composition is suitable for use in making contact lenses.

Claims

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

(A) about 15 to about 65% by weight of at least one amide group containing monomer being selected from a group consisting essentially of;

(a) heterocyclic amide group containing monomers consisting essentially of;

(1) N-(olefin containing group)-2-pyrrolidone,

(2) N-(olefin containing group)-2-piperidone,

(3) N-(olefin containing group)-2-imidazolidone, and

(4) N-(olefin containing group) succinimide,

wherein said olefin containing group is selected from a group consisting essentially of vinyl, acryloxy, methacryloxy, acrylatoalkyl, methacrylatoalkyl, acrylamidoalkyl and methacrylamidoalkyl groups, wherein the alkyl group contains from one to 4 carbon atoms, and

(b) noncyclic amide group containing monomers consisting essentially of N-alkyl acrylamide, N-alkyl methacrylamide, N,N-dialkyl acrylamide and N,N-dialkyl methacrylamide, wherein the alkyl group is individually selected from a group consisting of unsubstituted and substituted monovalent hydrocarbon radicals having from one to 6 carbon atoms, and

(B) about 10 to about 75% by weight of at least one organosilicon compound, wherein the essential constituent units of each molecular compound have the formulas;

##EQU3## wherein each molecular compound contains one M group and the molar ratio of from about 1 to 99 to about 99 to 1;

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

R'"'"' and R", which may be the same or different, are monovalent hydrocarbon groups selected from a group consisting of C₁ -C₄ alkyl groups, cyclohexyl groups and phenyl groups;

n is an integer of from one to three inclusive;

a is an integer selected from a range of 0 to 2 inclusive and b is an integer selected from a range of zero to three inclusive.

2. The composition of claim 1, wherein said amide group containing monomer being selected from a group consisting essentially of N-vinyl-2-pyrrolidone, N-(2'"'"'-methacrylatoethyl)-2-pyrrolidone, N-vinyl-2-piperidone, N-(2'"'"'-methacrylatoethyl)-2-piperidone, N-alkyl acrylamide, N-alkyl methacrylamide, N,N-dialkyl acrylamide, N,N-dialkyl methacrylamide and mixture thereof.

3. The composition of claim 1, wherein there is about 20 to about 55% by weight of at least one amide group containing monomer and about 20 to about 55% by weight of at least one organosilicon compound.

4. The composition of claim 3, wherein said prosthetic device is a contact lens device.

5. The composition of claim 4, wherein there is about 25 to about 45% by weight of at least one amide group containing monomer.

6. The composition of claim 5, wherein said amide group containing monomer is N-vinyl-2-pyrrolidone.

7. The composition of claim 5, wherein said amide group containing monomer is N-(2'"'"'-methacrylatoethyl)-2-pyrrolidone.

8. The composition of claim 5, wherein said amide group containing monomer is N,N-dimethyl methacrylamide.

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

(A) about 15 to about 65% by weight of at least one amide group containing monomer being selected from a group consisting essentially of;

(a) heterocyclic amide group containing monomers consisting essentially of;

(1) N-(olefin containing group)-2-pyrrolidone,

(2) N-(olefin containing group)-2-piperidone,

(3) N-(olefin containing group)-2-imidazolidone, and

(4) N-(olefin containing group) succinimide,

wherein said olefin containing group is selected from a group consisting essentially of vinyl, acryloxy, methacryloxy, acrylatoalkyl, methacrylatoalkyl, acrylamidoalkyl and methacrylamidoalkyl groups, wherein the alkyl group contains from one to 4 carbon atoms, and

(b) noncyclic amide group containing monomers consisting essentially of N-alkyl acrylamide, N-alkyl methacrylamide, N,N-dialkylacrylamide and N,N-dialkylmethacrylamide, wherein the alkyl group is individually selected from a group consisting of unsubstituted and substituted monovalent hydrocarbon radicals having from one to 6 carbon atoms;

(B) about 10 to about 75% by weight of at least one organosilicon compound, wherein the essential constituent units of each molecular compound have the formulas;

##EQU4## wherein each molecular compound contains one M group and the molar ratio of from about 1 to 99 to about 99 to 1;

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

R'"'"' and R", which may be the same or different, are monovalent hydrocarbon groups selected from a group consisting of C₁ -C₄ alkyl groups, cyclohexyl groups and phenyl groups;

n is an integer of from one to three inclusive;

a is an integer selected a range of from 0 to 2 inclusive and b is an integer selected a range of from zero to three inclusive; and

(C) about 0.1 to about 65% by weight of at least one ester of a C₁ -C₂₀ alkanol and an acid selected from a group consisting of acrylic and methacrylic acids.

10. The composition of claim 9, wherein there is about 20 to about 55% by weight of at least one amide group containing monomer and about 20 to about 55% by weight of at least one organosilicon compound, the said amide group containing monomer is selected from a group consisting essentially of N-vinyl-2-pyrrolidone, N-(2'"'"'-methacrylatoethyl)-2-pyrrolidone, N-vinyl-2-piperidone, N-alkyl acrylamide, N-alkyl methacrylamide, N,N-dialkyl acrylamide, N,N-dialkyl methacrylamide and mixture thereof.

11. A composition of matter specially adapted for use as a contact lens device having the characteristics of increased hydrophilicity, and oxygen permeability, said composition being a copolymer of comonomers consisting essentially of:

(A) about 20 to about 45% by weight of at least one amide group containing monomer being selected from a group consisting essentially of N-vinyl-2-pyrrolidone, N-(2'"'"'-methacrylatoethyl)-2-pyrrolidone, N-methyl acrylamide, N-methyl methacrylamide, N,N-dimethyl acrylamide and N,N-dimethyl methacrylamide;

(B) about 10 to about 50% by weight of at least one organosilicon compound, wherein the essential constituent units of each molecular compound have the formulas;

##EQU5## wherein each molecular compound contains one M group and the molar ratio of about 1 to 99 to about 99 to 1;

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

R'"'"' and R", which may be the same or different, are monovalent hydrocarbon groups selected from a group consisting of C₁ -C₄ alkyl groups and phenyl groups;

n is an integer of from one to three inclusive;

a is an integer selected a range of from 0 to 2 inclusive and b is an integer selected a range of from zero to three inclusive; and

(C) 0.2 to about 35% by weight of at least one ester of a C₁ -C₂₀ alkanol and an acid selected from a group consisting of acrylic and methacrylic acids.