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US4222909A Expired / Lapsed US ⏱️ 0.0 years remaining

Coating compositions comprising isocyanate-functional polymers containing a terminal thioalkyl group

Assignee: EIDP Inc
•
Filing: 1978-06-20
•
Granted: 1980-09-16
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Expires: 1998-06-20
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Abstract

Abstract Low molecular weight isocyanate-functional acrylic polymers are provided, which contain at least 10% by weight of copolymerized isocyanatoalkyl (meth)acrylate, are substantially free of toxic monomeric isocyanates, and have the following general structure: ##STR1## where R is alkyl or aryl, R 1 is hydrogen or methyl; X is COO--A--NCO or a mixture of COO--A--NCO and at least one of phenyl, COOR 2 , ##STR2## Cl, H; where A is an alkylene group having 2-6 carbon atoms, and R 2 is an alkyl group having 1-18 carbon atoms; and n is 2-400. These polymers can be crosslinked and are useful in a variety of applications such as finishes, pigment surface treatments and dispersants, and rheology control agents.

Inventors

  • 👤 Darryl W. Brixius
  • 👤 John A. Simms

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 19:08
CPC Classifications
C; C09; C09D; C09D125/00; C09D125/02; C09D125/04; C09D125/08; C09D125/14; C08; C08F; C08F20/00; C08F20/02; C08F20/10; C08F20/34; C08F20/36; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/72; C08G18/728; C08G18/77; C08G18/775; C09D7/00; C09D7/40; C09D7/45; C08L; C08L33/00; C08L33/04; C08L33/06; C08L33/062

Claims Analysis

Total Claims: 14
Claim 1
Independent Claim 159 words
A coating composition consisting essentially of (A) a polymeric or a low molecular weight polyfunctional material containing a functional group complementary to an isocyanate functionality selected from the group consisting of hydroxyl, amino, and carboxyl; and (B) a crosslinking agent which is an isocyanate-functional polymer containing at least 10%, by weight of the polymer, of copolymerized isocyanatoalkyl acrylate or isocyanatoalkyl methacrylate, wherein at least 10% by number of the polymer molecules have the following structure: ##STR10## where R is alkyl or aryl; R 1 is hydrogen or methyl; X is a COO--A--NCO or a mixture of COO--A--NCO and at least one of phenyl, COOR 2 , ##STR11## Cl, H; where A is an alkylene group having 2-6 carbon atoms, and R 2 is an alkyl group having 1-18 carbon atoms; and n is 2-400 so that the polymer has a number average molecular weight, determined by gel permeation chromatography, utilizing polystyrene standards of polydispersity less than 1.1, of 500-10,000.
Claim 2
Dependent Claim 159 words
A coating composition consisting essentially of (A) a polymeric or a low molecular weight polyfunctional material containing a functional group complementary to an isocyanate functionality selected from the group consisting of hydroxyl, amino, and carboxyl; and (B) a crosslinking agent which is an isocyanate-functional polymer containing at least 10%, by weight of the polymer, of copolymerized isocyanatoalkyl acrylate or isocyanatoalkyl methacrylate, wherein at least 10% by number of the polymer molecules have the following structure: ##STR10## where R is alkyl or aryl; R 1 is hydrogen or methyl; X is a COO--A--NCO or a mixture of COO--A--NCO and at least one of phenyl, COOR 2 , ##STR11## Cl, H; where A is an alkylene group having 2-6 carbon atoms, and R 2 is an alkyl group having 1-18 carbon atoms; and n is 2-400 so that the polymer has a number average molecular weight, determined by gel permeation chromatography, utilizing polystyrene standards of polydispersity less than 1.1, of 500-10,000.
Claim 3
Dependent Claim 153 words
A coating composition of claim 1 consisting essentially of (A) a polymer containing functional group complementary to an isocyanate functionality selected from the group consisting of hydroxyl, amino, and carboxyl; and (B) a crosslinking agent which is an isocyanate-functional polymer containing at least 10%, by weight of the polymer, of copolymerized isocyanatoalkyl acrylate or isocyanatoalkyl methacrylate, wherein at least 10% by number of the polymer molecules have the following structure: ##STR12## where R is alkyl or aryl, R 1 is hydrogen or methyl; X is COO--A--NCO or a mixture of COO--A--NCO and at least one of phenyl, COOR 2 , ##STR13## Cl, H; where A is an alkylene group having 2-6 carbon atoms, and R 2 is an alkyl group having 1-18 carbon atoms; and n is 2-400 so that the polymer has a number average molecular weight, determined by gel permeation chromatography, utilizing polystyrene standards of polydispersity less than 1.1, of 500-10,000.
Claim 4
Dependent Claim 165 words
A coating composition of claim 1 consisting essentially of (A) a polymer which is the copolymer of styrene, methyl methacrylate, and the esterification product of hydroxyethyl acrylate, phthalic anhydride, and a glycidyl ester of the formula ##STR14## where R 4 is a tertiary aliphatic hydrocarbon group containing 8-10 carbon atoms; in the weight ratio of approximately 30:15:55; and (B) an isocyanate-functional polymer containing at least 10%, by weight of the polymer, of copolymerized isocyanatoethyl methacrylate wherein at least 10% by number of the polymer molecules have the following structure: ##STR15## where R is alkyl; R 1 is hydrogen, methyl or mixtures thereof; X is a mixture of COO--CH 2 CH 2 --NCO and at least one of phenyl, COOR 2 , ##STR16## Cl, and H, where R 2 is an alkyl group having 1-18 carbon atoms; and n is 2-400 so that the polymer has a number average molecular weight, determined by gel permeation chromatography, utilizing polystyrene standards of polydispersity less than 1.1, of 500-10,000.
Claim 5
Dependent Claim 24 words
A coating composition of claim 1 consisting essentially of (A) a polyol and (B) a polymer of butyl acrylate, isocyanatoethyl methacrylate and lauryl mercaptan.
Claim 6
Dependent Claim 23 words
A coating composition of claim 1 consisting essentially of (A) 2-ethyl-1,3-hexanediol and (B) a polymer of butyl acrylate, isocyanatoethyl methacrylate and lauryl mercaptan.
Claim 7
Dependent Claim 11 words
A self-supporting film formed from a coating composition of claim 5.
Claim 8
Dependent Claim 24 words
A coating composition of claim 1 consisting essentially of (A) a diamine and (B) a polymer of butyl acrylate, isocyanatoethyl methacrylate and lauryl mercaptan.
Claim 9
Dependent Claim 11 words
A self-supporting film formed from a coating composition of claim 7.
Claim 10
Dependent Claim 17 words
A coating composition of claim 1 which is air-curable and wherein (A) is a drying oil alcohol.
Claim 11
Dependent Claim 38 words
A coating composition of claim 1 wherein (A) is a low molecular weight polyfunctional material selected from the group consisting of ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, butylene glycols, 1,12-dodecanediol, 2,2,4-trimethylpentane-1,3-diol, 2-ethyl-1,3-hexanediol, trimethylol propane, and pentaerythritol.
Claim 12
Dependent Claim 26 words
A coating composition of claim 1 wherein (A) is a low molecular weight polyfunctional material selected from the group consisting of 2,2,6,6-tetramethylpiperazine and bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate.
Claim 13
Dependent Claim 159 words
A graft polymer obtained by contacting (A) An isocyanate-functional polymer containing at least 10%, by weight of the polymer, of copolymerized isocyanatoalkyl acrylate or isocyanatoalkyl methacrylate, wherein at least 10% by number of the polymer molecules have the following structure: ##STR17## where R is alkyl or aryl, R 1 is hydrogen or methyl; X is COO--A--NCO or a mixture of COO--A--NCO and at least one of phenyl, COOR 2 , ##STR18## Cl, H; where A is an alkylene group having 2-6 carbon atoms, and R 2 is an alkyl group having 1-18 carbon atoms; and n is 2-400 so that the polymer has a number average molecular weight, determined by gel permeation chromatography, utilizing polystyrene standards of polydispersity less than 1.1, of 500-10,000; and (B) a substantially mono-functional polymer whose functional group is selected from the group consisting of OH, COOH, NH 2 , and NHR 3 , where R 3 is an alkyl group having 1-4 carbon atoms.
Claim 14
Dependent Claim 159 words
A graft polymer obtained by contacting (A) An isocyanate-functional polymer containing at least 10%, by weight of the polymer, of copolymerized isocyanatoalkyl acrylate or isocyanatoalkyl methacrylate, wherein at least 10% by number of the polymer molecules have the following structure: ##STR17## where R is alkyl or aryl, R 1 is hydrogen or methyl; X is COO--A--NCO or a mixture of COO--A--NCO and at least one of phenyl, COOR 2 , ##STR18## Cl, H; where A is an alkylene group having 2-6 carbon atoms, and R 2 is an alkyl group having 1-18 carbon atoms; and n is 2-400 so that the polymer has a number average molecular weight, determined by gel permeation chromatography, utilizing polystyrene standards of polydispersity less than 1.1, of 500-10,000; and (B) a substantially mono-functional polymer whose functional group is selected from the group consisting of OH, COOH, NH 2 , and NHR 3 , where R 3 is an alkyl group having 1-4 carbon atoms.

References Cited (Backward Citations)

US2718516A Cited
US3943159A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1983-09-16 1984-03-17 1984-09-16 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1987-09-16 1988-03-17 1988-09-16 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1991-09-16 1992-03-17 1992-09-16 $7700.00 Window Closed / Lapsed

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