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US4675374A Expired / Lapsed US ⏱️ 0.0 years remaining

Solventless polymeric composition reaction product of (1) adduct of amine and acrylate with (2) polyacrylate

Assignee: Individual
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Filing: 1985-07-18
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Granted: 1987-06-23
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Expires: 2005-07-18
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Abstract

Abstract Solventless polymeric compositions suitable for coatings and moldings are formed by the addition reaction product of a first component comprising mono, di or polyamines, or an adduct of mono, di or polyamines with mono, di or polyfunctional acrylates and/or epoxides and a second component comprising mono, di or polyacrylates or mixtures with mono, di or polyepoxides.

Inventors

  • 👤 Gus Nichols

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 09:23
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/40; C08G59/4007; C08G59/4014; C08G59/4035; C08G59/50; C08G59/52; C08G59/54; C08G59/56

Claims Analysis

Total Claims: 15
Claim 1
Independent Claim 64 words
A copolymer comprising the addition reaction product of: a first solventless component comprising an adduct of a mono, di or polyamine with a mono, di or polyfunctional acrylate or epoxide or mixtures thereof; and a second, solventless component comprising a di or polyacrylate or mixture thereof, or a mixture of a di or polyacrylate and a glycidyl ester of acrylic acid or methacrylic acid.
Claim 2
Dependent Claim 64 words
A copolymer comprising the addition reaction product of: a first solventless component comprising an adduct of a mono, di or polyamine with a mono, di or polyfunctional acrylate or epoxide or mixtures thereof; and a second, solventless component comprising a di or polyacrylate or mixture thereof, or a mixture of a di or polyacrylate and a glycidyl ester of acrylic acid or methacrylic acid.
Claim 3
Dependent Claim 40 words
A copolymer as defined in claim 1 wherein the first component is an adduct of p,p'methyl dianiline with hexane diol diacrylate and the second component is a mixture of hexane diol diacrylate and the condensation product of epichlorohydrin and bisphenol-A.
Claim 4
Dependent Claim 39 words
A polymerizable composition as defined in claim 1 wherein the first and second components are mixed together in substantially stoichiometric proportions such that the number of aminic hydrogens is substantially equal to the number of acrylic linkages plus epoxides.
Claim 5
Dependent Claim 27 words
A polymerizable composition as defined in claim 1 wherein the first and second components are liquids having a viscosity below about 1500 centipoise at about 25° C.
Claim 6
Dependent Claim 35 words
A polymerizable composition as defined in claim 1 wherein the first and second components thermoset to dry-through consistency when mixed together at a temperature of about 25° C. in about 1 to about 8 hours.
Claim 7
Dependent Claim 27 words
A polymerizable composition as defined in claim 1 further comprising from about 1 to about 3 percent wt. hexakis methoxy methylene melamine as a surface tension reducer.
Claim 8
Dependent Claim 91 words
A polymerizable composition as defined in claim 1 wherein the mono, di or poly functional amine has an aliphatic, cycloaliphatic, heterocyclic or aromatic structure represented by the general formulas R n (NH 2 ) n or R n (NHR 1 ) wherein the R n , R 1 radicals are composed of carbon and hydrogen atoms in simple amines and nitrogen, oxygen, sulfur, and halogen derivatives thereof in amine terminated compounds containing amide, imide, amide-imide, oxo, ketone, nitrile, sulfone, thiol, urea, or hydroxyl, backbone linkages and wherein n is an integer.
Claim 9
Dependent Claim 466 words
A polymerizable composition as defined in claim 1 wherein: said monoamine is selected from the group consisting of ethanol amine, diethanol amine, 2-ethyhexyl amine, dodecyl amine, tetradecyl amine, hexadecyl amine, octadecylamine, furfuryl amine, cyclohexylamine, aniline, chloro aniline, and the condensation products of n moles of 1,6 hexamethylene diamine, trimethyl hexamethylene diamine, isophorone diamine, or polyoxopropylene-230, 400, 600, 800, 1000, 2,000 diamines with n moles of a monofunctional anhydride selected from the group consisting of dodecenyl succinic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, maleic anhydride, succininc anhydride, and itaconic anhydride, or n moles of an acid selected from the group consisting of 2-ethyl hexanoic acid, pelargonic acid, dodecanoic acid, octadecanoic acid, furoic acid, benzoic acid, hydroxy acetic acid, and formic acid, or lower esters, substituted derivatives, higher or lower homologues thereof, or the amide-imide amine of polyoxypropylenetriamine-400, or a monohydrazide of dodecanoic acid, 2-ethyl hexanoic acid, or octadecanoic acid; said diamine is a simple diamine selected from the group consisting of hydrazine diamine, ethylene diamine, butylene diamine, hexamethylene diamine, 2-methyl, 1,5 pentane diamine, trimethyl hexamethylene diamine, isophorone diamine, cyclohexamethylene diamine, xylene diamines, p,p' methylene dianiline, metaphenylene diamine, oxo or sulfone dianiline, their isomers, halo, ester and ether anologues, higher or lower homologues and substituted derivatives, and the adduct of n mole of the above amines with n or 2n moles of at least one monofunctional acrylate or methacrylate selected from the group consisting of hydroxyethylene acrylate, acrylamide, acrylonitrile, methyl acrylonitrile, and the adducts of n moles of a difunctional acrylate or methacrylate selected from the group consisting of butene diol diacrylate, neopentyl glycol diacrylate, 1,6 hexamethylene diol diacrylate, oxydiethylene diacrylate, oxotetra ethylene glycol diacrylate, dihydrazides and the diamide-amines obtained from the condensation of n moles of dimer fatty acid, dodecenedioic acid, sabacic acid or their dimethyl esters with 2n moles of hydrazine or 2n moles of a diamine of above simple diamines with the sulfone, urea or amide imide diamines obtained from the condensation of n moles of sulfuryl chloride, urea, or trimellitic anhydride with 2n moles of Amine-6, hexamethylene diamine, methylene bis cyclohexamethylene diamine, polyoxypropylene diamines 230, 400, 600, 800, 1000, 2000; and said amine is a tri or poly amine selected from the group consisting of diethylene triamine, dipropylene triamine, triethylene tetraamine, tetraethylene pentamine, polyoxypropylene triamine-400, 2,4-bis(p-aminobenzyl) aniline, and condensates thereof with dicarboxylic or tricarboxylic acids and their lower esters with acids selected from the group consisting of oxalic acid, adipic acid, azelaic acid, sebalic acid, sebacic acid, dodecedioc acid, dimer fatty acids, isophthalic and terephthalic acids, trimellitic anhydride, trimesic acid, sulfuryl chloride, or urea at a molar ratio of 2 to 1 of di or tri poly amine to difunctional acid or ester or a molar ratio of 3 to 1 or di or tri poly amine to a trifunctional acid or ester.
Claim 10
Dependent Claim 223 words
A polymerizable composition as defined in claim 1 wherein: said acrylate is a monofunctional acrylate selected from the group consisting of hydroxyl ethylene acrylate, hydroxyl propylene acrylate, acrylonitrile, acrylamide, methylol acrylamide, dimethylol acrylamide, diacetone acrylamide, methyl acrylate, ethyl acrylate or butyl acrylate, methyl and alkyl derivatives thereof, and the analogues of crotonic acid; said difunctional acrylate is selected from the group consisting of butane diacrylate, neopentyl diacrylate, 1,6 hexamethylene diacrylate, oxo diethylene diacrylate, oxo triethylene diacrylate, oxo tetraethylene diacrylate, polyoxoethylene diol diacrylates or dimethyl acrylates, and di, tri or poly oxo propylene diol diacrylates or dimethyl acrylates, N,N' methylene bis acrylamide, N,N' methylene bis methyl acrylamide, and the adducts of n moles of an amine or an ethanol imine with n moles of a triacrylate; and said tri functional acrylate or methyl acrylate is selected from the group consisting of trimethylol propane triacrylate, pentaerythritol triacrylate, the tetra acrylate or methyl acrylate of pentaerythritol; the adducts of n moles of an imine with n moles of pentaerythritol tetracrylate or tetramethyl acrylate; and the adducts of n moles of a di-imine or n moles of a primary amine with 2n moles of a di, tri or polyacrylate or methyl acrylate, and the adducts of n moles of primary diamines with 3n or 4n moles of a di, tri or tetra functional acrylate or methyl acrylate.
Claim 11
Dependent Claim 66 words
A polymerizable composition as defined in claim 1 in which said epoxide is selected from the group consisting of ethylene, propylene, butene, styrene, and cyclohexamethylene oxides; aliphatic diepoxides; diglycidyl ether or bishenol A; terephathalic acid; aniline, novolac, phenol and cresol di epoxides; glycolate or adipates of dicyclohexamethylene and dimethyl cyclohexamethylene diepoxides; the halo and alkyl substituted derivatives, isomers, and higher or lower analogues of the above.
Claim 12
Dependent Claim 59 words
A polymerizable composition as defined in claim 1 wherein the first component is formed by mixing 2n moles of a monoacrylate with n moles of a first diamine to form a di imine diacrylate followed by the addition of 2n moles of second diamine to form a mixture which is heated to condense and evolve 2n moles of methanol.
Claim 13
Dependent Claim 64 words
A polymerizable composition as defined in claim 1 wherein the first component is formed by mixing n moles of a mono acrylate with n moles of a first diamine to form an amine-imine followed by the addition of n moles of a second mono amine to form a mixture which is heated to condense and evolve n moles of methanol, ethanol, ammonia or water.
Claim 14
Dependent Claim 86 words
A copolymer comprising the addition reaction product of a first component comprising a mono, di or polyamine, hydrazine, or an amino-hydrazine terminated derivative, or a mixture thereof with a mono, di or polyfunctional acrylate and a second component comprising a di or polyacrylate wherein the first and second components are mixed together in proportions such that the number of acrylic linkages are in excess of the aminic hydrogens so as to form a photoprepoymer which can be further polymerized by ultraviolet light or an electron beam.
Claim 15
Dependent Claim 86 words
A copolymer comprising the addition reaction product of a first component comprising a mono, di or polyamine, hydrazine, or an amino-hydrazine terminated derivative, or a mixture thereof with a mono, di or polyfunctional acrylate and a second component comprising a di or polyacrylate wherein the first and second components are mixed together in proportions such that the number of acrylic linkages are in excess of the aminic hydrogens so as to form a photoprepoymer which can be further polymerized by ultraviolet light or an electron beam.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1990-06-22 1990-12-22 1991-06-23 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1994-06-22 1994-12-22 1995-06-23 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1998-06-22 1998-12-22 1999-06-23 $7700.00 Window Closed / Lapsed

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