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US3689593A Expired / Lapsed US ⏱️ 0.0 years remaining

Chain transfer linked urethane graft copolymers

Assignee: EIDP Inc
•
Filing: 1971-11-19
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Granted: 1972-09-05
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Expires: 1991-11-19
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Abstract

Abstract Film-forming graft copolymers having a backbone and graft segments linked together by a chain transfer agent and a diisocyanate and a process for their preparation.

Inventors

  • 👤 Bruce W Jackson

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-30 12:48
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/62; C08G18/6216; C08G18/622; C08G18/6245; C08F; C08F299/00; C08F299/02; C08F299/06; C08G18/67; C08G18/671; C08G18/672; Y; Y10; Y10S; Y10S524/00; Y10S524/923; Y10S525/00; Y10S525/909; Y10S525/91; Y10S525/92

Claims Analysis

Total Claims: 19
Claim 1
Independent Claim 79 words
The graft copolymer of claim 1 wherein the monoethylenically unsaturated monomers have the general structure where R is -H, -CH3, or -CH2CH3 and R1 is an alkyl or cycloalkyl group of of one-18 carbon atoms B is a polymeric backbone segment having a molecular weight of up to 1,000,000, said polymeric backbone segment formed from monomers having the general structure where R is -H, -CH3, or -CH2CH3 and R1 is an alkyl or cycloalkyl group of one-18 carbon atoms.
Claim 2
Dependent Claim 75 words
The graft copolymer of claim 2 wherein A has a molecular weight (number average) of about 400 to 40,000 and is selected from the group consisting of methyl methacrylate, 2-ethylhexyl acrylate, butyl acrylate, ethyl acrylate, butyl-methacrylate, lauryl methacrylate and lauryl acrylate wherein R4 is selected from the group consisting of hydroxy ethyl methacrylate, acrylic and methacrylic acid, hydroxypropyl methacrylate, aminoethyl methacrylate and hydroxyethyl acrylate and wherein B is methyl methacrylate and other methyl methacrylate copolymers.
Claim 3
Dependent Claim 25 words
The graft copolymer of claim 3 wherein A is a 60/40 to 80/20 ratio by weight of 2-ethylhexyl acrylate/methyl methacrylate respectively wherein R2 is -CH2CH20-,
Claim 4
Dependent Claim 58 words
A film-forming organosol containing from about 10 to 60 percent by weight of film-forming material wherein at least 20 percent by weight of said film-forming material is the graft copolymer of claim 1 and an organic solvent or solvent blend wherein only one of the segment of said graft copolymer is soluble in said solvent or solvent blend.
Claim 5
Dependent Claim 58 words
A film-forming organosol containing from about 10 to 60 percent by weight of film-forming material wherein at least 20 percent by weight of said film-forming material is the graft copolymer of claim 2 and an organic solvent or solvent blend wherein only one of the segments of said graft copolymer is soluble in said solvent or solvent blend.
Claim 6
Dependent Claim 58 words
A film-forming organosol containing from about 10 to 60 percent by weight of film-forming material wherein at least 20 percent by weight of said film-forming material is the graft copolymer of claim 3 and an organic solvent or solvent blend wherein only one of the segments of said graft copolymer is soluble in said solvent or solvent blend.
Claim 7
Dependent Claim 58 words
A film-forming organosol containing from about 10 to 60 percent by weight of film-forming material wherein at least 20 percent by weight of said film-forming material is the graft copolymer of claim 4 and an organic solvent or solvent blend wherein only one of the segments of said graft copolymer is soluble in said solvent or solvent blend.
Claim 8
Dependent Claim 12 words
A coating composition comprising the organosol of claim 5, pigment, and plasticizer.
Claim 9
Dependent Claim 12 words
A coating composition comprising the organosol of claim 6, pigment, and plasticizer.
Claim 10
Dependent Claim 12 words
A coating composition comprising the organosol of claim 7, pigment and plasticizer.
Claim 11
Dependent Claim 12 words
A coating composition comprising the organosol Of claim 8, pigment and plasticizer.
Claim 12
Dependent Claim 174 words
A process for preparing the graft copolymer of claim 1 as a dispersion which comprises forming the graft segment by A. reacting a mixture of monomers having the general structure where R is H, -CH3 or -CH2CH3 and R1 is an alkyl or cycloalkyl group of one through 18 carbon atoms, functionally terminated chain transfer agents, and free radical initiators in an organic liquid by a free radical polymerization to produce a chain transfer agent terminated polymer B. reacting the chain transfer agent terminated polymer of (A) with a diisocyanate and optionally a catalyst by a condensation reaction to form an isocyanate terminated polymer, C. reacting the isocyanate terminated polymer with acrylic monomers having an active hydrogen to produce the graft segment, and D. polymerizing the backbone segment in situ with the graft segment by adding monomers having the same general structure as the monomers in (A) and free radical initiators to a solution of the graft segment and reacting this mixture by hydrogen abstraction and an addition reaction to form the graft copolymer.
Claim 13
Dependent Claim 76 words
The process of claim 13 wherein the monomers in (A) are esters, amides and nitriles of acrylic, methacrylic and ethacrylic acid, the functionally terminated chain transfer agents are selected from the group consisting of mercapto ethanol, 2-aminoethane thiol, mercapto isobutyric acid, thioglycolic acid, mercaptopropionic acid, and the free radical initiator is selected from the group consisting of azobisisobutyronitrile, benzoyl peroxide and acetyl peroxide and wherein the solvent forms 10 to 50% by weight of the mixture.
Claim 14
Dependent Claim 83 words
The process of claim 14 wherein the diisocyanate used in the condensation reaction of (B) is added in an amount of about 80 to 100 percent by equivalent weight of the chain transfer agent and wherein the acrylic monomers having an active hydrogen are present in an amount of about 80 to 110 percent by equivalent weight of the chain transfer agent and are selected from the group consisting of hydroxyethyl methacrylate, acrylic or methacrylic acid, hydroxypropyl methacrylate, aminoethyl methacrylate and hydroxyethyl acrylate.
Claim 15
Dependent Claim 36 words
The process of claim 15 wherein the monomers used to form the backbone segment are added in an amount such that the ratio of graft monomers to backbone monomers is from 1/1 to 1/30 by weight.
Claim 16
Dependent Claim 171 words
A process for preparing the graft copolymer of claim 2 as a dispersion which comprises forming the graft segment by A. reacting a mixture of monomers having the general structure where R is H, -CH3 or -CH2CH3 and R1 is an alkyl or cycloalkyl group of 1-18 carbon atoms functionally terminated chain transfer agents, and free radical initiators in an organic liquid by a free radical polymerization to produce a chain transfer agent terminated polymer B. reacting the chain transfer agent terminated polymer of (A) with a diisocyanate and optionally a catalyst by a condensation reaction to form an isocyanate terminated polymer, C. reacting the isocyanate terminated polymer with acrylic monomers having an active hydrogen to produce the graft segment, and polymerizing the backbone segment in situ with the graft segment by adding monomers having the same general structure as the monomers in (A) and free radical initiators to a solution of the graft segment, and reacting this mixture by hydrogen abstraction and an addition reaction to form the graft copolymer.
Claim 17
Dependent Claim 76 words
The process of claim 17 wherein the monomers in (A) are esters, amides and nitriles of acrylic, methacrylic and ethacrylic acid, the functionally terminated chain transfer agents are selected from the group consisting of mercapto ethanol, 2-aminoethane thiol, Mercapto isobutyric acid, thioglycolic acid, mercaptopropionic acid, and the free radical initiator is selected from the group consisting of azobisisobutyronitrile, benzoyl peroxide and acetyl peroxide and wherein the solvent forms 10 to 50% by weight of the mixture.
Claim 18
Dependent Claim 83 words
The process of claim 18 wherein the diisocyanate used in the condensation reaction of (B) is added in an amount of about 80 to 100 percent by equivalent weight of the chain transfer agent, wherein the acrylic monomers having an active hydrogen are present in an amount of about 80 to 110 percent by equivalent weight of the chain transfer agent and are selected from the group consisting of hydroxy ethyl methacrylate, acrylic or methacrylic acid, hydroxypropyl methacrylate, aminoethyl methacrylate and hydroxyethyl acrylate.
Claim 19
Dependent Claim 36 words
The process of claim 19 wherein the monomers used to form the backbone segment are added in an amount such that the ratio of graft monomers to backbone monomer is from 1/1 to 1/30 by weight.

References Cited (Backward Citations)

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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) 1975-09-05 1976-03-06 1976-09-05 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1979-09-05 1980-03-06 1980-09-05 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1983-09-05 1984-03-06 1984-09-05 $7700.00 Window Closed / Lapsed

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