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US4396377A Expired / Lapsed US ⏱️ 0.0 years remaining

Dental appliances having interpenetrating polymer networks

Assignee: Dentsply Research and Development Corp
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Filing: 1981-11-05
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Granted: 1983-08-02
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Expires: 2001-11-05
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Abstract

Abstract Compositions hardenable by exposure to heat or electromagnetic radiation are provided by blending from about 0% to about 50% by weight of an uncrosslinked polymer, from about 20% to about 66% of a polymerizable monomer capable of dissolving said polymer, from about 10% to about 70% of a crosslinked polymer in the form of discrete particles having average diameters of from 0.001 micron to about 500 microns and being swellable by said monomer, and from about 0.25% to about 27% of a crosslinking agent for said monomer. Such compositions exhibit superior chemical and physical characteristics when hardened and are suitable in a wide variety of applications as construction media. In accordance with a preferred form of the invention, a precursor blend is formed from a mixture comprising (A) from 13 to 52 weight percent of a crosslinked polymer of an ester of a C 1 -C 6 alkyl acrylic acid and a C 1 -C 20 alkyl or cycloalkyl alcohol, said crosslinked polymer being in the form of fine particles at least 50% by weight of which have average diameters less than 150 microns; (B) from 13 to 34 weight percent of an uncrosslinked polymerized ester of a C 1 -C 6 alkyl acrylic acid and a C 1 -C 20 alkyl or cycloalkyl alcohol having an average molecular weight of from 500,000 to 900,000 g/mole; (C) from 25 to 55% by weight of a polymerizable monomeric ester of a C 1 -C 6 alkyl acrylic acid and a C 1 -C 20 alkyl or cycloalkyl alcohol, which monomeric ester is capable of dissolving said uncrosslinked polymerized ester and of swelling, or interpenetrating, said crosslinked polymer particles; and (D) from 7% to 22% by weight of a crosslinking agent for said polymerizable monomeric ester. Such precursor blends, after being aged for a time sufficient to insure that the crosslinked polymer particles have become substantially fully swollen with or interpenetrated by the mixture of monomeric ester and crosslinking agent, is especially suitable in the production of prosthetic dental appliances, such as, for example, prosthetic teeth.

Inventors

  • 👤 Frederick D. Roemer
  • 👤 Louis H. Tateosian

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 13:58
CPC Classifications
C; C08; C08F; C08F265/00; C08F265/04; C08F265/06; A; A61; A61K; A61K6/00; A61K6/80; A61K6/884; A61K6/887; C08F291/00

Claims Analysis

Total Claims: 21
Claim 1
Independent Claim 116 words
A dental appliance comprising a hard, water insensitive shaped body having at least one portion comprising a polymerized blend of: (A) from 0% to about 50% of an uncrosslinked polymer capable of dissolving in component (B); (B) from about 20% to about 66% of a monofunctional polymerizable monomer; (C) from about 10% to about 70% of a crosslinked polymer in the form of discrete particles having average diameters up to about 500 microns and being swellable by said monomer; and (D) from about 7% to about 27% of a di- or polyfunctional crosslinking agent reactive with said polymerizable monomer; said percentages being based upon the total weight of A, B, C and D in said composition.
Claim 2
Dependent Claim 116 words
A dental appliance comprising a hard, water insensitive shaped body having at least one portion comprising a polymerized blend of: (A) from 0% to about 50% of an uncrosslinked polymer capable of dissolving in component (B); (B) from about 20% to about 66% of a monofunctional polymerizable monomer; (C) from about 10% to about 70% of a crosslinked polymer in the form of discrete particles having average diameters up to about 500 microns and being swellable by said monomer; and (D) from about 7% to about 27% of a di- or polyfunctional crosslinking agent reactive with said polymerizable monomer; said percentages being based upon the total weight of A, B, C and D in said composition.
Claim 3
Dependent Claim 23 words
The appliance of claim 1 wherein said crosslinked polymer is present in an amount of from about 13% to about 52% by weight.
Claim 4
Dependent Claim 23 words
The appliance of claim 1 wherein said uncrosslinked polymer is present in an amount of from about 13% to about 34% by weight.
Claim 5
Dependent Claim 23 words
The appliance of claim 1 wherein said polymerizable monomer is present in an amount of from about 25% to about 55% by weight.
Claim 6
Dependent Claim 22 words
The appliance of claim 1 wherein said crosslinking agent is present in amount of from about 7% to about 22% by weight.
Claim 7
Dependent Claim 21 words
The appliance of claim 1 wherein at least 50% by wight of said particles have average diameters below about 150 microns.
Claim 8
Dependent Claim 89 words
The appliance of claim 1 wherein said crosslinked polymer is present in an amount of about 13% to about 52% by weight, said uncrosslinked polymer is present in an amount of from about 13% to about 34% by weight, said polymerizable monomer is present in an amount of from about 25% to about 55% by weight, said crosslinking agent is present in an amount of from about 7% to about 22% by weight, and at least 50% bt weight of said particles have average diameters below about 150 microns.
Claim 9
Dependent Claim 41 words
The appliance of claims 1, 5, 6 or 7 wherein said crosslinking agent is selected from the group consisting of 2,2-bis(methacryloxyphenyl)propane; ethylene "glycol" dimethacrylate; ethylene "glycol" diacrylate; 2,2-bis[4-(2-hydroxy-3-methacryloxypropoxy)phenyl[propane; and the reaction product of either hydroxyethyl acrylate or hydroxyethyl methacrylate and 2,2,4-trimethylhexyl-1,6-diisocyanate.
Claim 10
Dependent Claim 33 words
The appliance of claims 1, 6 or 7 further comprising one or more members selected from the group consisting of free radical initiators, photochemical initiators, activators, pigments, fillers, adhesion modifiers and radiopaquing agents.
Claim 11
Dependent Claim 79 words
The appliance of claim 1 wherein said polymerizable monomer comprises an ester of an acid selected from the group consisting of acrylic acid and C 1 to C 6 alkyl acrylic acids and an alcohol selected from the group consisting of alkyl alcohols having from 1 to about 20 carbon atoms, cycloalkyl alcohols having from 1 to about 20 carbon atoms, phenol, and alkyl substituted phenol having from 1 to about 6 carbon atoms in the alkyl substituents thereof.
Claim 12
Dependent Claim 59 words
The appliance of claim 1 wherein said crosslinking agent comprises an ester of at least two moles of an acid selected from the group consisting of acrylic acid and C 1 to C 6 alkyl acrylic acids reacted with one moleof an alcohol having at least two hydroxylic functionalities said alcohol having from 2 to about 30 carbon atoms.
Claim 13
Dependent Claim 27 words
The appliance of claim 1 wherein said polymerizable monomer is selected from the group consisting of methyl-, ethyl-, trifluoroethyl-, propyl-, butyl-, pentyl-, and hexyl-, acrylate and methacrylate.
Claim 14
Dependent Claim 18 words
The appliance of claim 1 wherein said uncrosslinked polymer comprises a polymerized mixture of two or more monomers.
Claim 15
Dependent Claim 72 words
The appliance of claim 1 wherein said uncrosslinked polymer comprises a polymerized ester of an acid selected from the group consisting of acrylic acid and C 1 to C 6 alkyl acrylic acids and an alcohol selected from the group consisting of alkyl and cycloalkyl alcohols having from 1 to about 20 carbon atoms, phenol, and alkyl substituted phenol having from 1 to about 6 carbon atoms in the alkyl substituents thereof.
Claim 16
Dependent Claim 28 words
The appliance of claim 1 wherein said uncrosslinked polymer is selected from the group consisting of polymerized methyl-, ethyl-, propyl-, isopropyl- and butyl-acrylate and methacrylate and mixtures thereof.
Claim 17
Dependent Claim 33 words
The appliance of claim 1 wherein said crosslinked polymer comprises a polymerized misture of from about 70% to about 99.99% monomer and from about 0.01% to about 30% crosslinking agent for said monomer.
Claim 18
Dependent Claim 78 words
The appliance of claim 16 wherein said monomer comprises an ester of an acid selected from the group consisting of acrylic acids, and C 1 to C 6 alkyl acrylic acids and an alcohol selected from the group consisting of alkyl alcohols having from 1 to about 20 carbon atoms, cycloalkyl alcohols having from 1 to about 20 carbon atoms, phenol, and alkyl substituted phenol having from 1 to about 6 carbon atoms in the alkyl substituents thereof.
Claim 19
Dependent Claim 42 words
The appliance of claim 17 wherein said crosslinking agent comprises an ester of at least two moles of said acid reacted with one mole of an alcohol having at least two hydroxylic functionalities and having from 2 to about 30 carbon atoms.
Claim 20
Dependent Claim 59 words
The appliance of claim 16 wherein said crosslinking agent comprises an ester of at least two moles of an acid selected from the group consisting of acrylic acid and C 1 to C 6 alkyl acrylic acids, reacted with one mole of an alcohol having at least two hydroxylic functionalities and having from 2 to about 30 carbon atoms.
Claim 21
Dependent Claim 25 words
The appliance of claim 1 or 7 wherein said appliance exhibits the structure of an interpenetrating polymeric network at least locally interior to said portion.

References Cited (Backward Citations)

CA511802A Cited
GB569975A Cited
US3470615A Cited
US3427274A Cited
US4076671A Cited
US4302376A Cited
US4308190A Cited
US4369262A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1986-08-01 1987-01-31 1987-08-02 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1990-08-01 1991-01-31 1991-08-02 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1994-08-01 1995-01-31 1995-08-02 $7700.00 Window Closed / Lapsed

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