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US4284551A Expired / Lapsed US ⏱️ 0.0 years remaining

Tertiary aromatic amine accelerators derived from para-aminophenethanol

Assignee: HAROLD ARGENTAR 4721 IRIS PLACE ROCKVILLE MARYLAND 20853
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Filing: 1979-11-30
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Granted: 1981-08-18
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Expires: 1999-11-30
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Abstract

Abstract Tertiary aromatic amines derived from para-aminophenethanol act as accelerators for the peroxide catalyzed polymerization of vinyl monomers, especially methacrylates and acrylates, and for the curing of unsaturated polyesters. The amines are characterized by generally high reactivity and low toxicity, and by their yielding polymers of high strength and low color, and are thereby particularly suited for use in polymerizable or curable formulations employed in the filling and restoration of human teeth, in the preparation of cold-curing denture base materials for fabricating or repairing dentures and in the cementing of bone.

Inventors

  • 👤 Harold Argentar

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-26 20:52
CPC Classifications
A; A61; A61L; A61L24/00; A61L24/001; A61K; A61K6/00; A61K6/80; A61K6/884; A61K6/887; A61L24/0047; A61L24/0073; A61L24/04; A61L24/06; A61L27/00; A61L27/14; A61L27/16; A61L27/40; A61L27/44; A61L27/50; C; C08; C08F; C08F299/00; C08F299/02; C08F299/04; C08F299/0442; C08F299/0457; C08F4/00; C08F4/40

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 374 words
A composition of matter comprising (1) a component selected from the group consisting of polymerizable vinyl monomers and unsaturated polyesters, (2) a peroxide catalyst, and (3) a tertiary aromatic amine having the following structure: ##STR22## where R 1 and R 2 are the same or different and are selected from the following groups: (a) --CH 3 , (b) --CH 2 CH 2 C n H 2n+1 with n varying between 0 and 18, ##STR23## where R 1 ', R 2 ' and R 3 ' are each either hydrogen, normal alkyl, --C n H 2n+1 , with n varying between 1 and 20, or t-butyl, but if one R' is t-butyl, then the adjacent R' is hydrogen, ##STR24## where R 1 " is --C n H 2n+1 with n varying from 0 to 17, or (f) --CH 2 CH 2 OH; and where R 3 is either hydrogen, or a lower normal alkanoyl group, ##STR25## with n varying between 1 and 20, or ##STR26## wherein R is hydrogen or a methyl group; or (B) a polymeric amine having 10 or fewer amine groups which is the reaction product of the amine ##STR27## in which R 1 and R 2 are each hydrogen and R 3 is as defined in (A), with the diglycidyl ether of bisphenol A, viz., ##STR28## where n varies between 1 and 10, or the hydrolysis product of this polymeric amine, viz., ##STR29## (C) an amine having the formula ##STR30## with n varying between 1 and 10, where R 1 and R 2 are as defined in (A) or are of the formula ##STR31## and where R 3 is as defined in (A); or (D) a polymeric amine having 10 or fewer amine groups which is the reaction product of the amine (B) with methacrylic or acrylic acid; or (E) an amine having the formula ##STR32## where R 1 and R 2 are as defined in (A) but with no greater than 5 carbon atoms in the alkyl substituents of R 1 and R 2 , and where n varies between 2 and 10; or (F) an amine having the formula ##STR33## where R 1 and R 2 are as defined in (A), and where n varies between 2 and 10.
Claim 2
Dependent Claim 374 words
A composition of matter comprising (1) a component selected from the group consisting of polymerizable vinyl monomers and unsaturated polyesters, (2) a peroxide catalyst, and (3) a tertiary aromatic amine having the following structure: ##STR22## where R 1 and R 2 are the same or different and are selected from the following groups: (a) --CH 3 , (b) --CH 2 CH 2 C n H 2n+1 with n varying between 0 and 18, ##STR23## where R 1 ', R 2 ' and R 3 ' are each either hydrogen, normal alkyl, --C n H 2n+1 , with n varying between 1 and 20, or t-butyl, but if one R' is t-butyl, then the adjacent R' is hydrogen, ##STR24## where R 1 " is --C n H 2n+1 with n varying from 0 to 17, or (f) --CH 2 CH 2 OH; and where R 3 is either hydrogen, or a lower normal alkanoyl group, ##STR25## with n varying between 1 and 20, or ##STR26## wherein R is hydrogen or a methyl group; or (B) a polymeric amine having 10 or fewer amine groups which is the reaction product of the amine ##STR27## in which R 1 and R 2 are each hydrogen and R 3 is as defined in (A), with the diglycidyl ether of bisphenol A, viz., ##STR28## where n varies between 1 and 10, or the hydrolysis product of this polymeric amine, viz., ##STR29## (C) an amine having the formula ##STR30## with n varying between 1 and 10, where R 1 and R 2 are as defined in (A) or are of the formula ##STR31## and where R 3 is as defined in (A); or (D) a polymeric amine having 10 or fewer amine groups which is the reaction product of the amine (B) with methacrylic or acrylic acid; or (E) an amine having the formula ##STR32## where R 1 and R 2 are as defined in (A) but with no greater than 5 carbon atoms in the alkyl substituents of R 1 and R 2 , and where n varies between 2 and 10; or (F) an amine having the formula ##STR33## where R 1 and R 2 are as defined in (A), and where n varies between 2 and 10.
Claim 3
Dependent Claim 17 words
A composition of matter as in claim 1 wherein R 1 and R 2 are the same.
Claim 4
Dependent Claim 8 words
A composition of matter as in claim 1(B).
Claim 5
Dependent Claim 13 words
A composition of matter as in claim 1 further comprising a reinforcing filler.
Claim 6
Dependent Claim 18 words
A composition of matter as in claim 4 wherein the peroxide catalyst is benzoyl peroxide or lauroyl peroxide.
Claim 7
Dependent Claim 40 words
A restorative dental material comprising a composition of matter as in claim 1 wherein the component selected from the group consisting of polymerizable vinyl monomers and unsaturated polyesters is a methacrylate ester and the peroxide catalyst is a diacyl peroxide.
Claim 8
Dependent Claim 13 words
A restorative dental material as in claim 6 further comprising a reinforcing filler.
Claim 9
Dependent Claim 20 words
A bone cement comprising a composition of matter as in claim 1 wherein the peroxide catalyst is a diacyl peroxide.
Claim 10
Dependent Claim 14 words
A cold-curing denture base material comprising a composition of matter as in claim 1.
Claim 11
Dependent Claim 20 words
A composition of matter as in claims 1, 6, 7, 8 or 9 wherein the tertiary aromatic amine is para-dimethylaminophenethanol.
Claim 12
Dependent Claim 25 words
A method of fabricating a cold-curing denture base material which comprises preparing a composition as in claim 1 and permitting it to polymerize or cure.
Claim 13
Dependent Claim 17 words
A composition of matter as in claim 3 wherein R 3 is hydrogen and n is 2.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-08-17 1985-02-16 1985-08-18 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-08-17 1989-02-16 1989-08-18 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-08-17 1993-02-16 1993-08-18 $7700.00 Window Closed / Lapsed

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