← Back to Patent Explorer
US4866148A Expired / Lapsed US ⏱️ 0.0 years remaining

Hydrophilic copolymers, the use thereof as biomedical materials and contact-optical articles produced therefrom

Assignee: Bayer AG
•
Filing: 1987-05-07
•
Granted: 1989-09-12
•
Expires: 2007-05-07
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract The invention relates to new cross-linked copolymers of N-vinyl pyrrolidone, N-alkyl-N-vinyl carboxylic acid amides, methacrylates and optionally further copolymerizing monomers of a specific composition. the copolymers have a water absorption capacity of up to about 80% by weight, based on the hydrated state, and are suitable for the production of shaped articles which are in contact with living tissue in use. Examples include soft contact lenses and scleral lenses of high mechanical strength, in particular thin to very thin lenses for prolonged wear.

Inventors

  • 👤 Otto-Christian Geyer
  • 👤 Frank Wingler

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 21:38
CPC Classifications
C; C08; C08F; C08F226/00; C08F226/06; C08F226/10; G; G02; G02B; G02B1/00; G02B1/04; G02B1/041; G02B1/043

Claims Analysis

Total Claims: 33
Claim 1
Independent Claim 119 words
A hydrophilic cross-linked copolymer have a water absorption capacity of 25 to about 80 parts by weight based on the hydrated state, and consisting essentially copolymerized monomeric units: (A) 28 to 70 parts by weight of N-vinyl pyrrolidone, (B) from 2 to 20 parts by weight of N-methyl-vinyl acetamide, (C) 10.0 to 70 parts by weight of an ester of methacrylic acid containing 1 to 8 carbon atoms in the alcohol portion, (D) 0 to 1 part by weight of a polyfunctional (meth)acrylic acid ester cross-linking agent, (E) 0.01 to 1.5 parts by weight of a polyfunctional vinyl or allyl cross-linking agent, and (F) 0 to 30 parts by weight of monomers which copolymerize with (A), (B) and (C).
Claim 2
Dependent Claim 119 words
A hydrophilic cross-linked copolymer have a water absorption capacity of 25 to about 80 parts by weight based on the hydrated state, and consisting essentially copolymerized monomeric units: (A) 28 to 70 parts by weight of N-vinyl pyrrolidone, (B) from 2 to 20 parts by weight of N-methyl-vinyl acetamide, (C) 10.0 to 70 parts by weight of an ester of methacrylic acid containing 1 to 8 carbon atoms in the alcohol portion, (D) 0 to 1 part by weight of a polyfunctional (meth)acrylic acid ester cross-linking agent, (E) 0.01 to 1.5 parts by weight of a polyfunctional vinyl or allyl cross-linking agent, and (F) 0 to 30 parts by weight of monomers which copolymerize with (A), (B) and (C).
Claim 3
Dependent Claim 25 words
A hydrophilic cross-linked copolymer according to claim 1 having a water absorption capacity of 40 to 80 parts by weight, based on the hydrated state.
Claim 4
Dependent Claim 21 words
A copolymer according to claim 1, characterised in that the content of component (A) is 45 to 65 parts by weight.
Claim 5
Dependent Claim 21 words
A copolymer according to claim 1, characterised in that the content of component (B) is 4 to 15 parts by weight.
Claim 6
Dependent Claim 21 words
A copolymer according to claim 1, characterised in that the content of component (C) is 20 to 51 parts by weight.
Claim 7
Dependent Claim 21 words
A copolymer according to claim 1, characterised in that the content of component (D) is 0.1 to 0.5 parts by weight.
Claim 8
Dependent Claim 21 words
A copolymer according to claim 1, characterised in that the content of component (E) is 0.1 to 1.0 part by weight.
Claim 9
Dependent Claim 14 words
A copolymer according to claim 1, characterised in that component (C) is methyl methacrylate.
Claim 10
Dependent Claim 132 words
Contact optical articles which directly contact living tissue in use which comprise the hydrophilic cross-linked copolymer having a water absorption capacity of 25 to about 80 parts by weight, based on the hydrated state, and comprising as copolymerized monomeric units: (A) 28 to 70 parts by weight of N-vinyl pyrrolidone, (B) from 2 to 20 parts by weight of N-methyl-vinyl acetamide, (C) 10.0 to 70 parts by weight of an ester of methacrylic acid containing 1 to 8 carbon atoms in the alcohol portion, (D) 0 to 1 part by weight of a polyfunctional (meth) acrylic acid ester cross-linking agent, (E) 0.01 to 1.5 parts by weight of a polyfunctional vinyl or allyl cross-linking agent, and (F) 0 to 30 parts by weight of monomers which copolymerize with (A), (B) and (C).
Claim 11
Dependent Claim 132 words
Contact optical articles which directly contact living tissue in use which comprise the hydrophilic cross-linked copolymer having a water absorption capacity of 25 to about 80 parts by weight, based on the hydrated state, and comprising as copolymerized monomeric units: (A) 28 to 70 parts by weight of N-vinyl pyrrolidone, (B) from 2 to 20 parts by weight of N-methyl-vinyl acetamide, (C) 10.0 to 70 parts by weight of an ester of methacrylic acid containing 1 to 8 carbon atoms in the alcohol portion, (D) 0 to 1 part by weight of a polyfunctional (meth) acrylic acid ester cross-linking agent, (E) 0.01 to 1.5 parts by weight of a polyfunctional vinyl or allyl cross-linking agent, and (F) 0 to 30 parts by weight of monomers which copolymerize with (A), (B) and (C).
Claim 12
Dependent Claim 20 words
Contact optical articles according to claim 9 wherein the content of component (A) is 45 to 65 parts by weight.
Claim 13
Dependent Claim 20 words
Contact optical articles according to claim 9 wherein the content of component (B) is 4 to 15 parts by weight.
Claim 14
Dependent Claim 20 words
Contact optical articles according to claim 9 wherein the content of component (C) is 20 to 51 parts by weight.
Claim 15
Dependent Claim 20 words
Contact optical articles according to claim 9 wherein the content of component (D) is 0.1 to 0.5 parts by weight.
Claim 16
Dependent Claim 20 words
Contact optical articles according to claim 9 wherein the content of component (E) is 0.1 to 1.0 parts by weight.
Claim 17
Dependent Claim 13 words
Contact optical articles according to claim 9 wherein component (C) is methyl methacrylate.
Claim 18
Dependent Claim 15 words
Contact optical article according to claim 9 wherein the article is a hydrophilic soft lense.
Claim 19
Dependent Claim 36 words
Contact optical article according to claim 16 wherein the lense has a thickness at its center of from 0.03 to 0.15 mm for a minus lense and from 0.08 to 0.3 mm for a plus lense.
Claim 20
Dependent Claim 14 words
Contact optical article according to claim 9 wherein the article is a scleral lense.
Claim 21
Dependent Claim 24 words
Contact optical article according to claim 9 wherein the article is an aphakia lense with a center thickness of from 0.1 to 0.4 mm.
Claim 22
Dependent Claim 135 words
A cylindrical disc-shaped blank for use in the manufacture of contact optical articles which comprises a hydrophilic cross-linked copolymer having a water absorption capacity of 25 to about 80 parts by weight, based on the hydrated states, and comprising as copolymerized monomeric units: (A) 28 t 70 parts by weight of N-vinyl pyrrolidone, (B) from 2 to 20 parts by weight of N-methyl-vinyl acetamide, (C) 10.0 to 70 parts by weight of an ester of meth-acrylic acid containing 1 to 8 carbon atoms in the alcohol portion, (D) 0 to 1 part by weight of a polyfunctional (meth) acrylic acid ester cross-linking agent, (E) 0.01 to 1.5 parts by weight of a polyfunctional vinyl of allyl cross-linking agent, and (F) 0 to 30 parts by weight of monomers which copolymerize with (A), (B) and (C).
Claim 23
Dependent Claim 135 words
A cylindrical disc-shaped blank for use in the manufacture of contact optical articles which comprises a hydrophilic cross-linked copolymer having a water absorption capacity of 25 to about 80 parts by weight, based on the hydrated states, and comprising as copolymerized monomeric units: (A) 28 t 70 parts by weight of N-vinyl pyrrolidone, (B) from 2 to 20 parts by weight of N-methyl-vinyl acetamide, (C) 10.0 to 70 parts by weight of an ester of meth-acrylic acid containing 1 to 8 carbon atoms in the alcohol portion, (D) 0 to 1 part by weight of a polyfunctional (meth) acrylic acid ester cross-linking agent, (E) 0.01 to 1.5 parts by weight of a polyfunctional vinyl of allyl cross-linking agent, and (F) 0 to 30 parts by weight of monomers which copolymerize with (A), (B) and (C).
Claim 24
Dependent Claim 19 words
A blank according to claim 20 wherein the content of component (A) is 45 to 65 parts by weight.
Claim 25
Dependent Claim 19 words
A blank according to claim 20 wherein the content of component (B) is 4 to 15 parts by weight.
Claim 26
Dependent Claim 19 words
A blank according to claim 20 wherein the content of component C) is 20 to 51 parts by weight.
Claim 27
Dependent Claim 19 words
A blank according to claim 20 wherein the content of component (D) is 0.1 to 0.5 parts by weight.
Claim 28
Dependent Claim 19 words
A blank according to claim 20 wherein the content of component E) is 0.1 to 1.0 parts by weight.
Claim 29
Dependent Claim 12 words
A blank according to claim 20 wherein component (C) is methyl methacrylate.
Claim 30
Dependent Claim 154 words
A process for the production of hydrophilic, cross-linked copolymers as claimed in claim 1 wherein: (A) 28 to 70 parts by weight of N-vinyl pyrrolidone, (B) 2 to 20 parts by weight of N-methyl-vinyl acetamide, (C) 10.0 to 70 parts by weight of an ester of meth-acrylic acid containing 1 to 8 carbon atoms in the alcohol portion, (D) 0 to 1 parts by weight of a polyfunctional (meth) acrylic acid ester cross-linking agent, (E) 0.01 to 1.5 parts by weight of a polyfunctional vinyl or allyl cross-linking agent, and (F) 0 to 30 parts by weight of monomers which copolymerize with (A), (B) and (C), are polymerized by radical polymerization in a cylindrical vessel equipped with a plunger under a pressure of about 0.4 bar provided by the plunger, under fluorescent light for about three days at about 40° C., whereupon the vessel is emptied and the polymer allowed to swell in water.
Claim 31
Dependent Claim 43 words
A process for the production of hydrophilic, cross-linked copolymers as claimed in claim 1 wherein monomers (A) through (F) are copolymerized in the presence of up to 200 parts by weight of ethylene glycol by radical polymerization at about 20° to 120° C.
Claim 32
Dependent Claim 55 words
In the method of preparing a contact lense from a polymeric blank by cutting the blank to a predetermined configuration, the improvement comprises cutting a polymeric blank as claimed in claim 20 to a center thickness of from 0.03 to 0.15 mm for a minus lense and 0.08 to 0.3 mm for a plus lense.
Claim 33
Dependent Claim 30 words
In a method of increasing the supply of oxygen to eye tissue of a contact lense wearer, the improvement compises said lense being a lense as claimed in claim 16.

References Cited (Backward Citations)

US3316224A Cited
US3696085A Cited
EP0017512A2 Cited
US4703097A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1992-09-11 1993-03-13 1993-09-12 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1996-09-11 1997-03-13 1997-09-12 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2000-09-11 2001-03-13 2001-09-12 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag