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US4436887A
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N-Vinyl lactam based biomedical devices
Assignee: Bausch and Lomb Inc
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Filing: 1981-11-12
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Granted: 1984-03-13
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Expires: 2001-11-12
Abstract
Abstract N-vinyl lactam monomers and comonomers are cross-linked with resonance free di(alkene tertiary amine) cyclic compounds to obtain biomedical devices, including contact lenses, which have high oxygen permeability and good mechanical properties.
Inventors
- 👤 Richard C. Chromecek
- 👤 Gary D. Friends
- 👤 Lawrence Y. Wissman
- 👤 Raymond A. Yourd, III
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 20:29
CPC Classifications
C; C08; C08F; C08F226/00; C08F226/06; A; A61; A61L; A61L27/00; A61L27/14; A61L27/16; A61L33/00; A61L33/06; A61L33/064; B; B01; B01D; B01D71/00; B01D71/06; B01D71/44; B01D71/441; G; G02; G02B; G02B1/00; G02B1/04; G02B1/041; G02B1/043
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
299 words
As a new article of manufacture, a contact lens formed from a hydrophilic polymer formed by polymerizing (a) (1) one or more N-vinyl lactams and/or heterocyclic N-vinyl monomers, said N-vinyl lactams being selected from the group consisting of N-vinyl-2-pyrrolidinone, N-(1-methyl) vinyl pyrrolidinone, N-vinyl-2-piperidone and N-vinyl-2-caprolactam which may be substituted in the lactam ring by one or more lower alkyl groups, said heterocyclic N-vinyl monomers being selected from the group consisting of N-vinyl imidazole, N-vinyl succinimide, N-vinyl diglycolylimide, N-vinyl glutarimide, N-vinyl-3-morpholinone and N-vinyl-5-methyl-3-morpholinone, and (2) from zero to 50 weight percent of the total monomer present is at least one hydrophobic monomer or hydrophilic monomer other than N-vinyl lactam and/or heterocyclic N-vinyl monomer, said hydrophobic monomer(s) being selected from the group consisting of acrylates, methacrylates, itaconates, fumarates, maleates and crotonates wherein the esterified group has from 1 to 30 carbon atoms, said hydrophilic monomer(s) being selected from the group consisting of hydroxyesters, free acids, amides and amines of acrylates, methacrylates and itaconates, and (b) a resonance free di(alkene tertiary amine) cyclic compound crosslinking agent alone or in admixture with a crosslinking agent of another chemical structure in which case said cyclic compound is at least 50 mole percent of said mixture, said cyclic compound having the formula CH 2 :CG(CH 2 ) x N˜J˜N(CH 2 ) x CH:CH 2 wherein x is 0 or 1, G is hydrogen or methyl and J is the balance of structure forming cyclic dialkene urea, said agent being present in an amount from 0.01 to 10 weight percent of the total monomer of (A) (1) and (A) (2) present to form a crosslinked 3-dimensional polymeric network, said polymer having an oxygen permeability of at least 24×10 -11 cm 2 cm/(sec.cm 2 mmHg) and a tear initiation strength of at least 3 g/mm of thickness.
Claim 2
Dependent Claim
299 words
As a new article of manufacture, a contact lens formed from a hydrophilic polymer formed by polymerizing (a) (1) one or more N-vinyl lactams and/or heterocyclic N-vinyl monomers, said N-vinyl lactams being selected from the group consisting of N-vinyl-2-pyrrolidinone, N-(1-methyl) vinyl pyrrolidinone, N-vinyl-2-piperidone and N-vinyl-2-caprolactam which may be substituted in the lactam ring by one or more lower alkyl groups, said heterocyclic N-vinyl monomers being selected from the group consisting of N-vinyl imidazole, N-vinyl succinimide, N-vinyl diglycolylimide, N-vinyl glutarimide, N-vinyl-3-morpholinone and N-vinyl-5-methyl-3-morpholinone, and (2) from zero to 50 weight percent of the total monomer present is at least one hydrophobic monomer or hydrophilic monomer other than N-vinyl lactam and/or heterocyclic N-vinyl monomer, said hydrophobic monomer(s) being selected from the group consisting of acrylates, methacrylates, itaconates, fumarates, maleates and crotonates wherein the esterified group has from 1 to 30 carbon atoms, said hydrophilic monomer(s) being selected from the group consisting of hydroxyesters, free acids, amides and amines of acrylates, methacrylates and itaconates, and (b) a resonance free di(alkene tertiary amine) cyclic compound crosslinking agent alone or in admixture with a crosslinking agent of another chemical structure in which case said cyclic compound is at least 50 mole percent of said mixture, said cyclic compound having the formula CH 2 :CG(CH 2 ) x N˜J˜N(CH 2 ) x CH:CH 2 wherein x is 0 or 1, G is hydrogen or methyl and J is the balance of structure forming cyclic dialkene urea, said agent being present in an amount from 0.01 to 10 weight percent of the total monomer of (A) (1) and (A) (2) present to form a crosslinked 3-dimensional polymeric network, said polymer having an oxygen permeability of at least 24×10 -11 cm 2 cm/(sec.cm 2 mmHg) and a tear initiation strength of at least 3 g/mm of thickness.
Claim 3
Dependent Claim
18 words
The article according to claim 1 wherein said polymer has a water absorption content from 60% to 90%.
Claim 4
Dependent Claim
18 words
The article according to claim 2 wherein the polymer has a water absorption content of at least 70%.
Claim 5
Dependent Claim
34 words
The article according to claim 1 wherein the article is hydrolytically stable, the polymer has no more than a one percent change in water absorption content after heating in boiling water for 120 hours.
Claim 6
Dependent Claim
51 words
The article according to claim 1 wherein the resonance free di(alkene tertiary amine) cyclic compound is selected from the group consisting of cyclic dialkene urea, dialkene amides, dialkene hydrazides, dialkene hydantoins, dialkene hydrouracils, dialkene 2,2'-bis-imidazolin and mixtures thereof, said alkene being either vinyl, alpha methyl vinyl, alpha methyl allyl or allyl.
Claim 7
Dependent Claim
20 words
The article according to claim 5 wherein the resonance free di(alkene tertiary amine) cyclic compound is a cyclic divinyl area.
Claim 8
Dependent Claim
15 words
The article according to claim 6 wherein the cyclic divinyl urea is divinyl ethylene urea.
Claim 9
Dependent Claim
14 words
The article according to claim 5 wherein the cyclic compound is a dialkene 2,2'-bis-imidazolin.
Claim 10
Dependent Claim
12 words
The article according to claim 8 wherein the dialkene 2,2'-bis-imidazolin is 1,1'-divinyl-2,2'-bis-imidazolin.
Claim 11
Dependent Claim
11 words
The article according to claim 8 wherein the 2,2'-bis-imidazolin is 1,1-diallyl-2,2'-bis-imidazolin.
Claim 12
Dependent Claim
20 words
The article according to claim 5 wherein the resonance free di(alkene tertiary amine) cyclic compound is a cyclic allyl urea.
Claim 13
Dependent Claim
15 words
The article according to claim 11 wherein the cyclic allyl urea is diallyl ethylene urea.
Claim 14
Dependent Claim
25 words
The article according to claim 1 wherein at least 80 mole percent of the crosslinking agent is the resonance free di(alkene tertiary amine) cyclic compound.
Claim 15
Dependent Claim
21 words
The article according to claim 1 wherein the crosslinking agent is present in an amount from 0.1 to 3.0 weight percent.
Claim 16
Dependent Claim
18 words
The article according to claim 1 wherein the N-vinyl lactam and/or heterocyclic N-vinyl monomer is an N-vinyl lactam.
Claim 17
Dependent Claim
12 words
The article according to claim 15 wherein the N-vinyl lactam is N-vinyl-2-pyrrolidinone.
Claim 18
Dependent Claim
12 words
The article according to claim 15 wherein the N-vinyl lactam is N-vinyl-2-piperidone.
Claim 19
Dependent Claim
12 words
The article according to claim 15 wherein the N-vinyl lactam is N-vinyl-2-caprolactam.
Claim 20
Dependent Claim
19 words
The article according to claim 1 wherein the N-vinyl lactam and/or heterocyclic N-vinyl monomer is a heterocyclic N-vinyl monomer.
Claim 21
Dependent Claim
14 words
The article according to claim 19 wherein the N-vinyl heterocyclic monomer is N-vinyl imidazole.
Claim 22
Dependent Claim
47 words
The article according to claim 1 wherein from 70% to 90% by weight of the total monomers employed is the N-vinyl lactam or a mixture of the N-vinyl lactams and from 10% to 30% by weight is the hydrophobic comonomer, the hydrophilic comonomer or a mixture thereof.
Claim 23
Dependent Claim
23 words
The article according to claim 21 wherein the N-vinyl lactam is N-vinyl pyrrolidinone and the hydrophobic monomers are methyl methacrylate and cyclohexyl methacrylate.
Claim 24
Dependent Claim
27 words
The article according to claim 21 wherein the N-vinyl lactam is N-vinyl pyrrolidinone and the hydrophobic monomers are methyl methacrylate and either isobornyl acrylate or isobornyl methacrylate.
Claim 25
Dependent Claim
30 words
The article according to claim 21 wherein the N-vinyl lactam is N-vinyl pyrrolidinone, the hydrophilic monomer is hydroxyethyl methacrylate and the hydrophobic monomer is either isobornyl acrylate or isobornyl methacrylate.
Claim 26
Dependent Claim
26 words
The article according to claim 21 wherein the N-vinyl lactam is N-vinyl pyrrolidinone, the hydrophilic monomer is hydroxyethyl methacrylate and the hydrophobic monomer is methyl methacrylate.
Claim 27
Dependent Claim
51 words
A process for preparing the article of claim 1 comprising (a) admixing together the monomer and crosslinking agent with a free radical initiator, (b) charging the mixture to a mold and (c) activating and maintaining the activation of the free radical initiator until the desired degree of crosslinking has been obtained.
Claim 28
Dependent Claim
35 words
The process of claim 26 wherein a water soluble or solvent soluble diluent is admixed with the monomer and crosslinking agent and after the article has been formed removing the diluent by hydrating the article.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-03-13 | 1987-09-12 | 1988-03-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-03-13 | 1991-09-12 | 1992-03-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-03-13 | 1995-09-12 | 1996-03-13 | $7700.00 | Window Closed / Lapsed |