US4351755A
Expired / Lapsed
US
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Isocyanate-functional polymers containing a terminal monosulfide group
Assignee: EIDP Inc
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Filing: 1980-10-08
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Granted: 1982-09-28
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Expires: 2000-10-08
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 07:52
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.
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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 |