US4435558A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Hardenable urethane-epoxy resin mixtures
Assignee: Bayer Pharma AG
•
Filing: 1982-12-15
•
Granted: 1984-03-06
•
Expires: 2002-12-15
Abstract
Abstract The method of hardening a glycidyl compound with a polyether urethane urea amino hardener is disclosed, said hardener being prepared by reacting (1) a blocked prepolymer prepared by reacting a phenolic compound with the reaction product of a polyether polyol with an excess of polyisocyanate, with (2) a polyfunctional amino compound.
Inventors
- 👤 Christian Burba
- 👤 Hermann-Josef Lucas
- 👤 Bernd Neffgen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 12:38
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/10; C08L; C08L63/00; C08L75/00; C08L75/04; C08L75/08
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
128 words
The method of hardening a glycidyl compound having more than one epoxy group per molecule, which method comprises admixing with said glycidyl compound an approximately stoichiometric amount of an amino hardener which is a polyether urethane urea amine prepared by the reaction of (1) a prepolymer having blocked isocyanate groups, prepared by reacting a phenol or alkylphenol with the reaction product of a polyether polyol or polythioether polyol with an excess of a polyisocyanate, with (2) a polyfunctional amino compound having (a) at least two reactive amino hydrogen atoms per molecule or (b) at least one reactive amino hydrogen atom and at least one azomethine group per molecule, the amine then being liberated from the reaction product formed between (1) and 2(b) by hydrolysis of the azomethine group.
Claim 2
Independent Claim
128 words
The method of hardening a glycidyl compound having more than one epoxy group per molecule, which method comprises admixing with said glycidyl compound an approximately stoichiometric amount of an amino hardener which is a polyether urethane urea amine prepared by the reaction of (1) a prepolymer having blocked isocyanate groups, prepared by reacting a phenol or alkylphenol with the reaction product of a polyether polyol or polythioether polyol with an excess of a polyisocyanate, with (2) a polyfunctional amino compound having (a) at least two reactive amino hydrogen atoms per molecule or (b) at least one reactive amino hydrogen atom and at least one azomethine group per molecule, the amine then being liberated from the reaction product formed between (1) and 2(b) by hydrolysis of the azomethine group.
Claim 3
Dependent Claim
29 words
The method as in claim 1 wherein said mixture additionally comprises at least one member selected from the group consisting of fillers, pigments, accelerators, viscosity regulators, and other additives.
Claim 4
Dependent Claim
78 words
the method as in claim 1 wherein said blocked prepolymer is the reaction product of (A) a polyalkylene polyether polyol having an average molecular weight between 150 to 10,000 with an excess of (B) a polyfunctional aliphatic or cycloaliphatic isocyanate, the ratio of NCO groups of OH groups being between 1.5 and 2.5, followed by further reaction of the resulting prepolymer containing NCO groups with (c) a phenol, the phenol/NCO ratio being between about 1.0 and about 1.5.
Claim 5
Dependent Claim
18 words
The method as in claim 3 wherein said polyol has an average molecular weight between 400 and 5000.
Claim 6
Dependent Claim
17 words
The method as in claim 3 wherein said polyol has an average molecular weight of about 2000.
Claim 7
Dependent Claim
12 words
The method as in claim 3 wherein said isocyanate is isophorone diisocyanate.
Claim 8
Dependent Claim
15 words
The method as in claim 3 wherein said phenol is a para-noylphenol or a para-butylphenol.
Claim 9
Dependent Claim
314 words
The method as in claim 1 wherein said polyfunctional amino compound is selected from the group consisting of (A) amines of the formuls R--NH--R.sup.1 --NH--R wherein R is linear or branched alkyl having from 1 to 4 carbon atoms, or is hydrogen, and R 1 is linear or branched aliphatic, cycloaliphatic, or araliphatic hydrocarbon, which may be substituted, having from 2 to 20 carbon atoms, or is the alkyl portion of a dimeric fatty diamine which may be interrupted by hetero atoms; (B) amines of the formula R.sup.2 --(R.sup.3 --NH--).sub.m --R.sup.3 --R.sup.2, wherein R 2 is --N═C(R 4 ) (R '4 ), R 3 is --CH 2 --CH 2 -- or --CH 2 --CH 2 --CH 2 --, R 4 and R '4 are the same or different and are --CH 3 , --CH 2 CH 3 , or --C(CH 3 ) 3 , and m is 1 or 2; (C) amines of the formula ##STR3## wherein R 5 is H, or wherein R 5 is --(CH 2 ) k --R 2 and k is 2 or 3, or wherein R 5 is (--CH 2 ) h ##STR4## (CH 2 ) k --R 6 , R 6 is --NHR or --R 2 , h is 0, 1, 2 or 3, and X is C or N; (D) condensation products of an amine (A)-(C) with a carboxylic acid wherein, when an amine (B) is used with m=1 or an amine (C) is used with R 6 =R 2 , the ratio of amino hydrogen atom to carbamate aryl ester groups is 1:1, and wherein, when an amine (A) or (B) is used with m=2, or an amine (C) is used with R 6 =NHR, the ratio of amino hydrogen atoms to carbamate aryl ester groups is from 1.8:1 to 2:1, an amino group being liberated by hydrolysis from compounds containing a group R 2 .
Claim 10
Independent Claim
108 words
A method for making a polyether urethane urea amine having two or more reactive amino hydrogen atoms per molecule, which method comprises reacting (1) a prepolymer having blocked isocyanate groups, prepared by reacting a phenol or alkylphenol with the reaction product of a polyether polyol or polythioether polyol with an excess of a polyisocyanate, with (2) a polyfunctional amino compound having (a) at least two reactive amino hydrogen atoms per molecule or (b) at least one reactive amino hydrogen atom and at least one azomethine group per molecule, the amine then being liberated from the reaction product formed between (1) and 2(b) by hydrolysis of the azomethine group.
Claim 11
Independent Claim
108 words
A method for making a polyether urethane urea amine having two or more reactive amino hydrogen atoms per molecule, which method comprises reacting (1) a prepolymer having blocked isocyanate groups, prepared by reacting a phenol or alkylphenol with the reaction product of a polyether polyol or polythioether polyol with an excess of a polyisocyanate, with (2) a polyfunctional amino compound having (a) at least two reactive amino hydrogen atoms per molecule or (b) at least one reactive amino hydrogen atom and at least one azomethine group per molecule, the amine then being liberated from the reaction product formed between (1) and 2(b) by hydrolysis of the azomethine group.
Claim 12
Dependent Claim
35 words
A method as in claim 9 wherein said amino compound is present in an excess such that the ratio of reactive amino hydrogen atoms to blocked isocyanate groups is from about 2:1 to about 4:1.
Claim 13
Dependent Claim
31 words
A method as in claim 9 wherein said amino compound is present in an excess such that the ratio of reactive amino hydrogen atoms to blocked isocyanate groups is about 2:1.
Claim 14
Dependent Claim
12 words
A polyether urethane urea amine made by the method of claim 9.
References Cited (Backward Citations)
GB1399257A
Cited
DE2152606C3
Cited
DE2338256A1
Cited
GB1411485A
Cited
US3993708A
Cited
DE2418041C3
Cited
US4137276A
Cited
US4328330A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-03-06 | 1987-09-05 | 1988-03-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-03-06 | 1991-09-05 | 1992-03-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-03-06 | 1995-09-05 | 1996-03-06 | $7700.00 | Window Closed / Lapsed |