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Isocyanate-functional polymers containing a terminal monosulfide group

Assignee: EIDP Inc
•
Filing: 1980-10-08
•
Granted: 1982-09-28
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Expires: 2000-10-08
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Abstract

Abstract Low molecular weight polydisperse isocyanate-functional acrylic polymers are provided which contain terminal monosulfide groups on at least 10% by number of polymer molecules but are substantially free of toxic monomeric isocyanates. The polymers are prepared by direct reaction of the monomers, e.g., 2-isocyanatoethyl methacrylate and butyl acrylate, in the presence of a mercaptan chain-transfer agent and a polymerization initiator but in the substantial absence of water and of Lewis-type bases. They can be crosslinked and are useful in a variety of applications such as moisture-curing coating compositions.

Inventors

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

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 08:16
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/72; C08G18/728; C08F; C08F220/00; C08F220/02; C08F220/10; C08F220/34; C08F220/36; C09; C09D; C09D133/00; C09D133/04; C09D133/14; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31551; Y10T428/31645; Y10T428/31678; Y10T428/31692; Y10T428/31699

Claims Analysis

Total Claims: 33
Claim 1
Independent Claim 188 words
An isocyanate-functional polymer of at least 10% by weight of isocyanatoalkyl acrylate or isocyanatoalkyl methacrylate, polymerized alone or with a polymerizable comonomer, any polymerizable comonomer being at least one member of the group consisting of alkyl acrylates and methacrylates; styrene; ethylene; vinyl acetate; and vinyl chloride, in the presence of 1-20% by weight, based on the weight of the polymer, of a mercaptan chain-transfer agent, wherein at least 10% by number of the polymer molecules have the following structure: ##STR5## where RS is the residue of a mercaptan chain-transfer agent, R-- being C 4 -C 12 alkyl, phenyl, benzyl or ##STR6## where R 3 -- is C 4 -C 12 alkyl, phenyl or benzyl and m is 0-8; R 1 is hydrogen or methyl; X is COO--A--NCO or a mixture of COO--A--NCO and at least one of ##STR7## where A is an alkylene group having 2-6 carbon atoms, and R 2 is an alkyl group having 1-12 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 188 words
An isocyanate-functional polymer of at least 10% by weight of isocyanatoalkyl acrylate or isocyanatoalkyl methacrylate, polymerized alone or with a polymerizable comonomer, any polymerizable comonomer being at least one member of the group consisting of alkyl acrylates and methacrylates; styrene; ethylene; vinyl acetate; and vinyl chloride, in the presence of 1-20% by weight, based on the weight of the polymer, of a mercaptan chain-transfer agent, wherein at least 10% by number of the polymer molecules have the following structure: ##STR5## where RS is the residue of a mercaptan chain-transfer agent, R-- being C 4 -C 12 alkyl, phenyl, benzyl or ##STR6## where R 3 -- is C 4 -C 12 alkyl, phenyl or benzyl and m is 0-8; R 1 is hydrogen or methyl; X is COO--A--NCO or a mixture of COO--A--NCO and at least one of ##STR7## where A is an alkylene group having 2-6 carbon atoms, and R 2 is an alkyl group having 1-12 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 33 words
A polymer of claim 1 containing at least one polymerizable comonomer of the group consisting of methyl, ethyl, butyl, hexyl, 2-ethylhexyl and lauryl acrylates and methacrylates, styrene, ethylene, vinyl acetate and vinyl chloride.
Claim 4
Dependent Claim 12 words
The polymer of claim 1 wherein the isocyanatoalkyl methacrylate is isocyanatoethyl methacrylate.
Claim 5
Dependent Claim 16 words
A coating composition comprising a solution of a polymer of claim 1 in an organic solvent.
Claim 6
Dependent Claim 14 words
The polymer of claim 1 containing 15-50% of copolymerized isocyanatoalkyl acrylate or isocyanatoalkyl methacrylate.
Claim 7
Dependent Claim 9 words
The polymer of claim 1 wherein X is COO'A--NCO.
Claim 8
Dependent Claim 18 words
The polymer of claim 1 wherein 25-40% by number of the polymer molecules contain a terminal RS-- group.
Claim 9
Dependent Claim 12 words
A polymer of claim 1 of the monomers isocyanatoethyl methacrylate/methyl methacrylate/butyl methacrylate/mercaptan.
Claim 10
Dependent Claim 12 words
The polymer of claim 8 wherein the monomeric weight ratio is 45.9/22.9/19.4/11.8.
Claim 11
Dependent Claim 10 words
A polymer of claim 1 of the monomers isocyanatoethyl methacrylate/styrene/mercaptan.
Claim 12
Dependent Claim 12 words
The polymer of claim 10 wherein the monomeric weight ratio is 45.9/42.6/10.7.
Claim 13
Dependent Claim 11 words
A polymer of claim 1 of the monomers isocyanatoethyl methacrylate/butyl acrylate/mercaptan.
Claim 14
Dependent Claim 12 words
The polymer of claim 12 wherein the monomeric weight ratio is 45.5/41.6/12.8.
Claim 15
Dependent Claim 12 words
The polymer of claim 12 wherein the monomeric weight ratio is 45.7/45.4/6.7.
Claim 16
Dependent Claim 11 words
A polymer of claim 1 of the monomers isocyanatoethyl methacrylate/ethylhexyl acrylate/mercaptan.
Claim 17
Dependent Claim 12 words
The polymer of claim 15 wherein the monomeric weight ratio is 45.2/41.9/12.8.
Claim 18
Dependent Claim 12 words
A polymer of claim 1 of the monomers isocyanatoethyl methacrylate/methyl methacrylate/n-butyl acrylate/mercaptan.
Claim 19
Dependent Claim 12 words
The polymer of claim 17 wherein the monomeric weight ratio is 28.1/57.6/9.7/2.1.
Claim 20
Dependent Claim 13 words
A polymer of claim 1 of the monomers isocyanatoethyl methacrylate/methyl methacrylate lauryl methacrylate/mercaptan.
Claim 21
Dependent Claim 12 words
The polymer of claim 19 wherein the monomeric weight ratio is 30/60/10/2.1.
Claim 22
Dependent Claim 11 words
A polymer of claim 1 of the monomers isocyanatoethyl methacrylate/butyl acrylate/styrene/mercaptan.
Claim 23
Dependent Claim 12 words
The polymer of claim 19 wherein the monomeric weight ratio is 53.27/19.6/19.1/7.04.
Claim 24
Dependent Claim 20 words
A substantially anhydrous solution of at least 60% by weight of a polymer of claim 1 in an organic solvent.
Claim 25
Dependent Claim 25 words
A substantially anhydrous solution of at least 60% by weight of a polymer of claim 8, 10, 12, 15 or 17 in an organic solvent.
Claim 26
Dependent Claim 10 words
A moisture-curing coating composition of a polymer of claim 1.
Claim 27
Dependent Claim 10 words
A coating composition of claim 25 containing a curing catalyst.
Claim 28
Dependent Claim 9 words
A coating composition of claim 25 containing a pigment.
Claim 29
Dependent Claim 12 words
A coating composition of claim 25 wherein X is COOR 2 .
Claim 30
Dependent Claim 16 words
A coating composition of claim 25 wherein R 2 is an alkyl group having 1-12 carbons.
Claim 31
Dependent Claim 10 words
A coating composition of claim 25 wherein X is phenyl.
Claim 32
Dependent Claim 17 words
A moisture-curing coating composition of a polymer of claim 8, 10, 12, 15, 17, 19 or 21.
Claim 33
Dependent Claim 23 words
A coating composition comprising a solution of a polymer of claim 8, 10, 12, 15, 17, 19 or 21 in an anhydrous solvent.

References Cited (Backward Citations)

US2471959A Cited
GB774897A Cited
US2718516A Cited
GB759860A Cited
US3579482A Cited
US3498943A Cited
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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) 1985-09-27 1986-03-29 1986-09-28 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1989-09-27 1990-03-29 1990-09-28 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1993-09-27 1994-03-29 1994-09-28 $7700.00 Window Closed / Lapsed

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