US4178427A
Expired / Lapsed
US
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Polyether urea epoxy curing agent
Assignee: Huntsman Corp
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Filing: 1978-02-06
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Granted: 1979-12-11
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Expires: 1998-02-06
Abstract
Abstract An improved curable epoxy resin composition of a vicinalpolyepoxide and an effective amount of a novel polyether urea curing agent is disclosed. The improved curable epoxy resins which are useful as coatings, castings, sealants, and adhesives show improved tensile shear strength, flexural strength, and ultimate elongation. The novel polyether urea curing agents of the instant invention are characterized by terminal primary amino groups and are formed by reaction of polyoxyalkylenepolyamines with urea, urea forming compounds, or bifunctional isocyanates. A preferred curing agent includes a mixture of a novel polyether urea formed by reaction of a polyoxypropylenepolyamine having a molecular weight of from about 200-2000 and an effective amount of urea; and another known epoxy resin curing agent such as polyoxyalkylenepolyamine in ratios of from about 5:1 to 1:5 by weight.
Inventors
- 👤 Harold G. Waddill
- 👤 Heinz Schulze
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 00:13
CPC Classifications
C; C08; C08G; C08G71/00; C08G71/02; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/48; C08G18/50; C08G18/5021; C08G59/00; C08G59/18; C08G59/40; C08G59/4007; C08G59/4014; C08G59/4021; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31511; Y10T428/31529
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
124 words
A curable epoxy resin composition consisting essentially of: a vicinal polyepoxide; and, an effective amount of a polyether urea curing agent having terminal primary amino groups and being formed by the reaction of a compound selected from a group consisting of bifunctional isocyanates obtained by phosgenation of an aniline formaldehyde condensation product with a polyoxyalkylenepolyamine of the formula: ##STR12## wherein X is a hydrogen, a methyl radical, or an ethyl radical; Z is a hydrocarbon radical having 2 to 5 carbon atoms forming from 2 to 4 external ether linkages, n is a number from 1 to about 15, and r is a number from 2 to 4 wherein the molar ratio of said isocyanate compound to said polyoxyalkylenepolyamine is from 0.25 to 0.50.
Claim 2
Dependent Claim
124 words
A curable epoxy resin composition consisting essentially of: a vicinal polyepoxide; and, an effective amount of a polyether urea curing agent having terminal primary amino groups and being formed by the reaction of a compound selected from a group consisting of bifunctional isocyanates obtained by phosgenation of an aniline formaldehyde condensation product with a polyoxyalkylenepolyamine of the formula: ##STR12## wherein X is a hydrogen, a methyl radical, or an ethyl radical; Z is a hydrocarbon radical having 2 to 5 carbon atoms forming from 2 to 4 external ether linkages, n is a number from 1 to about 15, and r is a number from 2 to 4 wherein the molar ratio of said isocyanate compound to said polyoxyalkylenepolyamine is from 0.25 to 0.50.
Claim 3
Dependent Claim
22 words
The curable epoxy resin composition of claim 1 wherein said polyoxyalkylenepolyamine is a polyoxypropylenepolyamine having a molecular weight of from about 200-2000.
Claim 4
Dependent Claim
38 words
The curable epoxy resin composition of claim 1 wherein said polyether urea curing agent is employed in combination with an effective amount of a co-curing agent selected from a group consisting of aliphatic polyamines, aromatic polyamines and polyoxyalkylenepolyamines.
Claim 5
Dependent Claim
35 words
The curable epoxy resin composition of claim 3 wherein said co-curing agent is a polyoxyalkylenepolyamine and is present in an amount of from about 5:1 to 1:5 by weight of said polyether urea curing agent.
Claim 6
Dependent Claim
23 words
The curable epoxy resin composition of claim 4 wherein said co-curing agent is a polyoxypropylenepolyamine having a molecular weight of from about 200-2000.
Claim 7
Dependent Claim
185 words
A curable epoxy resin composition consisting essentially of: a vicinal polyepoxide; and, an effective amount of a polyether urea curing agent of the formula: ##STR13## wherein A is a polyoxyalkylene radical containing from about 1 to about 15 oxyalkylene groups wherein each oxyalkylene group contains from 2 to about 4 carbon atoms; R is a hydrocarbon radical containing from 2 to 5 carbon atoms and forming from 2 to 4 oxycarbon linkages with A and B; B is a polyoxyalkylene amino radical containing from about 1 to 15 oxyalkylene groups wherein each oxyalkylene group contains from 2 to about 4 carbon atoms; X is a radical derived from a bifunctional isocyanate obtained by the phosgenation of an aniline formaldehyde condensation product having two ##STR14## groups; c and d are from 1 to 3 and chosen so that their sum is from 2 to 4; e is a number from 1 to 3; f is a number from 1 to 3; g is a number from 1 to 3; y is a number from 0 to about 5; z is a number from 0 to 2.
Claim 8
Dependent Claim
185 words
A curable epoxy resin composition consisting essentially of: a vicinal polyepoxide; and, an effective amount of a polyether urea curing agent of the formula: ##STR13## wherein A is a polyoxyalkylene radical containing from about 1 to about 15 oxyalkylene groups wherein each oxyalkylene group contains from 2 to about 4 carbon atoms; R is a hydrocarbon radical containing from 2 to 5 carbon atoms and forming from 2 to 4 oxycarbon linkages with A and B; B is a polyoxyalkylene amino radical containing from about 1 to 15 oxyalkylene groups wherein each oxyalkylene group contains from 2 to about 4 carbon atoms; X is a radical derived from a bifunctional isocyanate obtained by the phosgenation of an aniline formaldehyde condensation product having two ##STR14## groups; c and d are from 1 to 3 and chosen so that their sum is from 2 to 4; e is a number from 1 to 3; f is a number from 1 to 3; g is a number from 1 to 3; y is a number from 0 to about 5; z is a number from 0 to 2.
Claim 9
Dependent Claim
113 words
The curable epoxy resin composition of claim 6 where A corresponds to the formula: ##STR15## wherein n is a number from 0 to 15; B corresponds to the formula: ##STR16## wherein m is a number from 0 to 15; c and d are from 1 to 2 and chosen so that their sum is from 2 to 3; e is a number from 1 to 2; g is a number from 1 to 2; f is a number from 1 to 2; z is a number from 0 to 1; y is a number from 1 to 4; and x is a radical selected from a group consisting of ##STR17## and mixtures thereof.
Claim 10
Dependent Claim
20 words
The curable epoxy resin composition of claim 7 wherein n and m are, independently, numbers from about 1 to 10.
Claim 11
Dependent Claim
44 words
The curable epoxy resin composition of claim 6 wherein the amount of polyether urea curing agent to polyepoxide is that amount required such that the total number of amine equivalents is from about 0.8 to about 1.2 times the number of epoxide equivalents present.
Claim 12
Dependent Claim
23 words
The curable epoxy resin composition of claim 9 wherein said amine equivalent and said epoxide equivalents are present in a ratio of 1:1.
Claim 13
Dependent Claim
37 words
The curable epoxy resin composition of claim 6 further consisting essentially of: an effective amount of additive selected from a group consisting of conventional pigments, dyes, fillers, flame retardant agents, compatible natural resins and compatible synthetic resins.
Claim 14
Dependent Claim
38 words
The curable epoxy resin composition of claim 6 wherein said polyether urea curing agent is employed in combination with an effective amount of a co-curing agent selected from a group consisting of aliphatic polyamines, aromatic polyamines, and polyoxyalkylenepolyamine.
Claim 15
Dependent Claim
35 words
The curable epoxy resin composition of claim 12 wherein said co-curing agent is a polyoxyalkylenepolyamine which is present in an amount of from about 5:1 to 1:5 by weight of said polyether urea curing agent.
Claim 16
Dependent Claim
15 words
The curable epoxy resin composition of claim 13 wherein said co-curing agent is a polyoxypropylenepolyamine.
Claim 17
Dependent Claim
120 words
An epoxy resin curing agent for curing vicinal epoxy resins consisting essentially of: a polyether urea having terminal primary amino groups and being formed by the reaction of a compound selected from a group consisting of bifunctional isocyanates obtained by the phosgenation of an aniline formaldehyde condensation product with a polyoxyalkylenepolyamine of the formula: ##STR18## wherein X is a hydrogen, a methyl radical, or an ethyl radical; Z is a hydrocarbon radical having 2 to 5 carbon atoms forming from 2 to 4 external ether linkages; n is a number from 1 to about 15; and r is a number from 2 to 4 wherein the molar ratio of said isocyanate compound to said polyoxyalkylenepolyamine is from 0.25 to 0.50.
Claim 18
Dependent Claim
120 words
An epoxy resin curing agent for curing vicinal epoxy resins consisting essentially of: a polyether urea having terminal primary amino groups and being formed by the reaction of a compound selected from a group consisting of bifunctional isocyanates obtained by the phosgenation of an aniline formaldehyde condensation product with a polyoxyalkylenepolyamine of the formula: ##STR18## wherein X is a hydrogen, a methyl radical, or an ethyl radical; Z is a hydrocarbon radical having 2 to 5 carbon atoms forming from 2 to 4 external ether linkages; n is a number from 1 to about 15; and r is a number from 2 to 4 wherein the molar ratio of said isocyanate compound to said polyoxyalkylenepolyamine is from 0.25 to 0.50.
Claim 19
Dependent Claim
22 words
The epoxy resin curing agent of claim 15 wherein said polyoxyalkylenepolyamine is a polyoxypropylenepolyamine having a molecular weight of from about 200-2000.
Claim 20
Dependent Claim
26 words
The epoxy resin curing agent of claim 15 wherein said bifunctional isocyanates are selected from a group consisting of 4,4'-diphenylmethane diisocyanate, 2,4'-diphenylmethane diisocyanate, and mixtures thereof.
Claim 21
Dependent Claim
173 words
An epoxy resin curing agent consisting essentially of a polyether urea of the formula: ##STR19## wherein A is a polyoxyalkylene radical containing from about 1 to about 15 oxyalkylene groups wherein each oxyalkylene group contains from 2 to about 4 carbon atoms; R is a hydrocarbon radical containing from 2 to 5 carbon atoms forming from 2 to 4 oxycarbon linkages with A and B; B is a polyoxyalkylene amino radical containing from about 1 to 15 oxyalkylene groups wherein each oxyalkylene group contains from 2 to about 4 carbon atoms; X is a radical derived from a bifunctional isocyanate obtained by the phosgenation of an aniline formaldehyde condensation product having two ##STR20## groups; c and d are from 1 to 3 and chosen so that their sum is from 2 to 4; e is a number from 1 to 3; f is a number from 1 to 3; g is a number from 1 to 3; y is a number from 0 to 5; z is a number from 0 to 2.
Claim 22
Dependent Claim
173 words
An epoxy resin curing agent consisting essentially of a polyether urea of the formula: ##STR19## wherein A is a polyoxyalkylene radical containing from about 1 to about 15 oxyalkylene groups wherein each oxyalkylene group contains from 2 to about 4 carbon atoms; R is a hydrocarbon radical containing from 2 to 5 carbon atoms forming from 2 to 4 oxycarbon linkages with A and B; B is a polyoxyalkylene amino radical containing from about 1 to 15 oxyalkylene groups wherein each oxyalkylene group contains from 2 to about 4 carbon atoms; X is a radical derived from a bifunctional isocyanate obtained by the phosgenation of an aniline formaldehyde condensation product having two ##STR20## groups; c and d are from 1 to 3 and chosen so that their sum is from 2 to 4; e is a number from 1 to 3; f is a number from 1 to 3; g is a number from 1 to 3; y is a number from 0 to 5; z is a number from 0 to 2.
Claim 23
Dependent Claim
23 words
The epoxy resin curing agent of claim 18 where X is the radical selected from a group consisting of ##STR21## and mixtures thereof.
Claim 24
Dependent Claim
97 words
The epoxy resin curing agent of claim 18 where A corresponds to the formula: ##STR22## wherein n is a number from 0 to 15; B corresponds to the formula: ##STR23## wherein m is a number from 0 to 15; c and d are 1 to 2 chosen so that their sum is from 2 to 3; e is a number from 1 to 2; g is a number from 1 to 2; f is a number from 1 to 2; z is a number from 0 to 1; and y is a number from 1 to 4.
Claim 25
Dependent Claim
20 words
The epoxy resin curing agent of claim 20 wherein n and m are, independently, numbers from about 1 to 10.
Claim 26
Dependent Claim
124 words
A process for preparing a polyether urea having terminal primary amino groups comprising the steps of: reacting, at temperatures of 245° C. to 250° C. a compound selected from a group consisting of bifunctional isocyanates obtained by the phosgenation of an aniline formaldehyde condensation product with a polyoxyalkylenepolyamine of the formula: ##STR24## wherein X is a hydrogen, a methyl radical, or an ethyl radical, Z is a hydrocarbon radical having 2 to 5 carbon atoms forming from 2 to 4 external ether linkages, n is a number from 1 to about 15; and r is a number from 2 to 4; wherein the molar ratio of said isocyanate to polyoxyalkylenepolyamine is from 0.25 to 0.50 and, recovering said polyether urea from the reaction mixture.
Claim 27
Dependent Claim
124 words
A process for preparing a polyether urea having terminal primary amino groups comprising the steps of: reacting, at temperatures of 245° C. to 250° C. a compound selected from a group consisting of bifunctional isocyanates obtained by the phosgenation of an aniline formaldehyde condensation product with a polyoxyalkylenepolyamine of the formula: ##STR24## wherein X is a hydrogen, a methyl radical, or an ethyl radical, Z is a hydrocarbon radical having 2 to 5 carbon atoms forming from 2 to 4 external ether linkages, n is a number from 1 to about 15; and r is a number from 2 to 4; wherein the molar ratio of said isocyanate to polyoxyalkylenepolyamine is from 0.25 to 0.50 and, recovering said polyether urea from the reaction mixture.
Claim 28
Dependent Claim
25 words
The process of claim 22 wherein said compound is a bifunctional isocyanate selected from a group consisting of 4,4'-diphenylmethane diisocyanate, 2,4'-diphenylmethane diisocyanate, and mixtures thereof.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-12-10 | 1983-06-11 | 1983-12-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-12-10 | 1987-06-11 | 1987-12-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-12-10 | 1991-06-11 | 1991-12-11 | $7700.00 | Window Closed / Lapsed |