US5354834A
Expired / Lapsed
US
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Polyisocyanate curing agent, and coating composition and adhesive composition employing the same
Assignee: Nippon Polyurethane Industry Co Ltd
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Filing: 1992-01-10
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Granted: 1994-10-11
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Expires: 2012-01-10
Abstract
Abstract A curing agent for a two-component type polyurethane, containing as a main constituent a polyisocyanate derived from hexamethylene diisocyanate, the polyisocyanate having a viscosity of lower than 1,400 mP.a/25 DEG C. in substantially free from monomeric hexamethylene diisocyanate and a solvent, having a uretidine dione dimer content of more than 10%, and having an isocyanurate cyclic trimer content of less than 60%.
Inventors
- 👤 Mitsuhiro Yoshida
- 👤 Susumu Sato
- 👤 Yukio Obuchi
- 👤 Shin Konishi
- 👤 Masanori Shindo
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 13:51
CPC Classifications
C; C09; C09J; C09J175/00; C09J175/04; C08; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/72; C08G18/77; C08G18/78; C08G18/79; C08G18/791; C08G18/792; C08G18/798; C09D; C09D175/00; C09D175/04
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
93 words
A method for making a curing agent for a two-component polyurethane comprising the steps of: (i) partially urethanizing hexamethylene diisocyanate; (ii) Polymerizing said partially urethanized hexamethylene diisocyanate by exposing it to a sufficient amount of catalyst under conditions suitable to produce polyisocyanate having a viscosity lower than 1400 millipascal.second/measured at 25° C. in the state substantially free from monomeric hexamethylene diisocyanate and solvent, and having a uretidine dione dimer content of more than 10 percent by weight and an isocyanurate cyclic trimer content of less than 60 percent by weight of the polyisocyanate.
Claim 2
Independent Claim
93 words
A method for making a curing agent for a two-component polyurethane comprising the steps of: (i) partially urethanizing hexamethylene diisocyanate; (ii) Polymerizing said partially urethanized hexamethylene diisocyanate by exposing it to a sufficient amount of catalyst under conditions suitable to produce polyisocyanate having a viscosity lower than 1400 millipascal.second/measured at 25° C. in the state substantially free from monomeric hexamethylene diisocyanate and solvent, and having a uretidine dione dimer content of more than 10 percent by weight and an isocyanurate cyclic trimer content of less than 60 percent by weight of the polyisocyanate.
Claim 3
Independent Claim
99 words
A method for making a polyurethane coating composition comprising the steps of: (i) partially urethanizing hexamethylene diisocyanate; (ii) Polymerizing said partially urethanized hexamethylene diisocyanate by exposing it to a sufficient amount of catalyst under conditions suitable to produce polyisocyanate having a viscosity lower than 1400 millipascal.second/measured at 25° C. in the state substantially free from monomeric hexamethylene diisocyanate and solvent, and having a uretidine dione dimer content of more than 10 percent by weight and an isocyanurate cyclic trimer content of less than 60 percent by weight of the polyisocyanate; and (iii) adding said polyisocyanate to a polyhydroxyl compound.
Claim 4
Independent Claim
99 words
A method for making a polyurethane coating composition comprising the steps of: (i) partially urethanizing hexamethylene diisocyanate; (ii) Polymerizing said partially urethanized hexamethylene diisocyanate by exposing it to a sufficient amount of catalyst under conditions suitable to produce polyisocyanate having a viscosity lower than 1400 millipascal.second/measured at 25° C. in the state substantially free from monomeric hexamethylene diisocyanate and solvent, and having a uretidine dione dimer content of more than 10 percent by weight and an isocyanurate cyclic trimer content of less than 60 percent by weight of the polyisocyanate; and (iii) adding said polyisocyanate to a polyhydroxyl compound.
Claim 5
Dependent Claim
32 words
The method of claim 1 and further wherein the polyisocyanate has a uretidine dione dimer content of from about 15 percent by weight to about 40 percent by weight of the polyisocyanate.
Claim 6
Dependent Claim
32 words
The method of claim 2 and further wherein the polyisocyanate has a uretidine dione dimer content of from about 15 percent by weight to about 40 percent by weight of the polyisocyanate.
Claim 7
Dependent Claim
36 words
The method of claim 1, and further wherein the polyisocyanate has a viscosity of from about 100 to about 1,000 millipascal.second/measured at 25° C. in the state substantially free from monomeric hexameric hexamethylene diisocyanate and solvent.
Claim 8
Dependent Claim
36 words
The method of claim 2, and further wherein the polyisocyanate has a viscosity of from about 100 to about 1,000 millipascal.second/measured at 25° C. in the state substantially free from monomeric hexameric hexamethylene diisocyanate and solvent.
Claim 9
Dependent Claim
31 words
The method of claim 1, and further wherein the polyisocyanate has an isocyanurate cyclic trimer content of from about 15 percent by weight and 45 percent by weight of the polyisocyanate.
Claim 10
Dependent Claim
31 words
The method of claim 2, and further wherein the polyisocyanate has a isocyanurate cyclic trimer content of from about 15 percent by weight and 45 percent by weight of the polyisocyanate.
Claim 11
Dependent Claim
26 words
The method of claim 1, and further wherein the polyisocyanate contains isocyanate groups and uretidine groups in a ratio of from about 0.2:1 to about 0.7:1.
Claim 12
Dependent Claim
26 words
The method of claim 2, and further wherein the polyisocyanate contains isocyanate groups and uretidine groups in a ratio of from about 0.2:1 to about 0.7:1.
Claim 13
Dependent Claim
29 words
The method of claim 1, and further wherein the catalyst is selected from the group consisting of triethylphosphine, dibutylethylphosphine, tri-n-propylphosphine, triisopropylphosphine, tri-n-butylphosphine, triisobutylphosphine, tri-tert-butylphosphine, triamylphosphine, trioctylphosphine, tribenzylphosphine, and benzylmethylphosphine.
Claim 14
Dependent Claim
52 words
The method of claim 11, and further wherein the polyisocyanate-producing reaction is stopped by adding phosphoric acid or methyl p-toluenesulfonate to the reaction mixture, and in which sufficient, unreacted monomeric hexamethylene diisocyanate is removed from the reaction mixture so the polyisocyanate contains not more than about 0.5% by weight monomeric hexamethylene diisocyanate.
Claim 15
Dependent Claim
28 words
The method of claim 2, and further wherein catalyst is selected from the group consisting of triethylphosphine, dibutylethylphosphine, tri-n-propylphosphine, triisopropylphosphine, tri-n-butylphosphine, triisobutylphosphine, tri-tert-butylphosphine, triamylphosphine, trioctylphosphine, tribenzylphosphine, and benzylmethylphosphine.
Claim 16
Dependent Claim
53 words
The method of claim 13, and further wherein the polyisocyanate-producing reaction is stopped by adding phosphoric acid or methyl p-toluenesulfonate to the reaction mixture, and in which sufficient, unreacted monomeric hexamethylene diisocyanate is removed from the reaction mixture so that the polyisocyanate contains not more than about 0.5% by weight monomeric hexamethylene diisocyanate.
Claim 17
Dependent Claim
47 words
The method of claim 2, and further wherein the polyhydroxyl compound contains saturated or unsaturated polyester resins, polycaprolactone resins, saturated or unsaturated oil-modified or fatty acid-modified alkyd resins, aminoalkyd resins, polycarbonate resins, acrylic resins, polyether resins, epoxy resins, polyurethane resins, cellulose acetate butyrate resins, or fluorine-containing resins.
Claim 18
Dependent Claim
31 words
The method of claim 2, and further wherein the molar ratio of isocyanate groups in the polyisocyanate to hydroxyl groups in the polyhydroxyl compound ranges from about 6:4 to about 4:6.
Claim 19
Dependent Claim
15 words
The method of claim 2, and further wherein the polyhydroxyl compound is a polyester polyol.
Claim 20
Dependent Claim
23 words
The method of claim 1, and further wherein the partially urethanized hexamethylene diisocyanate is prepared by the reaction of hexamethylene diisocyanate and 1,3-butanediol.
Claim 21
Dependent Claim
23 words
The method of claim 2, and further wherein the partially urethanized hexamethylene diisocyanate is prepared by the reaction of hexamethylene diisocyanate and 1,3-butanediol.
Claim 22
Dependent Claim
25 words
The method of claim 1 and further wherein the polymerization reaction is conducted at a temperature within the range of from 50° to 90° C.
Claim 23
Dependent Claim
25 words
The method of claim 2 and further wherein the polymerization reaction is conducted at a temperature within the range of from 50° to 90° C.
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1997-10-10 | 1998-04-11 | 1998-10-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2001-10-10 | 2002-04-11 | 2002-10-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2005-10-10 | 2006-04-11 | 2006-10-11 | $7700.00 | Window Closed / Lapsed |