US4115446A
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Polyether polyureides
Assignee: Huntsman Corp
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Filing: 1976-11-22
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Granted: 1978-09-19
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Expires: 1996-11-22
Abstract
Abstract Novel polyether polyureides useful in the manufacture of plastics, sealants, molds, foams and coatings. The novel composition comprises a mono- or di-substituted ureido-terminated polyoxyalkylene prepared by reacting a primary amine-terminated polyoxyalkylene containing material with suitable substituted ureido forming compounds at temperatures in the range from about 20° C to about 150° C in a molar ratio of about one molecule of ureido forming material for each terminal primary amino group.
Inventors
- 👤 Heinz Schulze
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 12:00
CPC Classifications
C; C08; C08G; C08G65/00; C08G65/02; C08G65/32; C08G65/321; C08G65/326; C07; C07C; C07C275/00; C07C275/04; C07C275/28; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/48; C08G18/50; C08G18/5021; C08G65/325; C08G65/338; C08G71/00; C08G71/02
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
244 words
A polyether polyureide comprising a substituted ureido-terminated polyoxyalkylene selected from the group consisting of a compound of the formula: ##STR27## wherein R 1 and R 2 are, independently, hydrogen or an aliphatic or aromatic monovalent hydrocarbon radical, provided at least one R 1 or R 2 is not hydrogen; X' is 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 20; and, r is a number from 2 to 4; and a compound of the formula: ##STR28## wherein R 1 and R 2 are as defined above; A is a polyoxyalkylene radical containing from about 1 to 17 oxyalkylene groups; B is a polyoxyalkylene amino radical containing from about 1 to 17 oxyalkylene groups; R is a hydrocarbon radical having from 2 to 5 carbon atoms and forming from 2 to 4 oxycarbon linkages with A and B; X is a C═O radical, a C═S radical or a radical derived from a difunctional isocyanate having two ##STR29## groups; c and d are from 1 to 3 chosen such that their sum is from 1 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, and z is a number from 0 to 2.
Claim 2
Dependent Claim
244 words
A polyether polyureide comprising a substituted ureido-terminated polyoxyalkylene selected from the group consisting of a compound of the formula: ##STR27## wherein R 1 and R 2 are, independently, hydrogen or an aliphatic or aromatic monovalent hydrocarbon radical, provided at least one R 1 or R 2 is not hydrogen; X' is 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 20; and, r is a number from 2 to 4; and a compound of the formula: ##STR28## wherein R 1 and R 2 are as defined above; A is a polyoxyalkylene radical containing from about 1 to 17 oxyalkylene groups; B is a polyoxyalkylene amino radical containing from about 1 to 17 oxyalkylene groups; R is a hydrocarbon radical having from 2 to 5 carbon atoms and forming from 2 to 4 oxycarbon linkages with A and B; X is a C═O radical, a C═S radical or a radical derived from a difunctional isocyanate having two ##STR29## groups; c and d are from 1 to 3 chosen such that their sum is from 1 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, and z is a number from 0 to 2.
Claim 3
Dependent Claim
32 words
The polyether polyureide of claim 1 wherein X' is a methyl radical; n is a number from 2 to 17, Z is a 1,2-propylene radical and r is about 2 or 3.
Claim 4
Dependent Claim
102 words
The polyether polyureide of claim 1 wherein A corresponds to the formula: ##STR30## wherein n is a number from 0 to 15; B corresponds to the formula: ##STR31## 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 C═O radical.
Claim 5
Dependent Claim
18 words
The polyether polyureide of claim 3 wherein n and m are, independently, numbers from about 1 to 10.
Claim 6
Dependent Claim
21 words
The polyether polyureide of claim 1 wherein X is the radical selected from a group consisting of ##STR32## and mixtures thereof.
Claim 7
Dependent Claim
269 words
A polyether polyureide comprises a substituted ureido-terminated polyoxyalkylene material, formed by the reaction of a substituted ureido group forming compound with a compound selected from a polyoxyalkylenepolyamine of the formula ##STR33## wherein X' is a hydrogen, a methyl radical or an ethyl radical; Z is a hydrocarbon radical having from 2 to 5 carbon atoms forming from 2 to 4 external either linkages; n is a number from 1 to about 20 and r is a number from 2 to 4 and a polyoxyalkylene ureylene or thioureylene having terminal primary amino groups of the formula ##STR34## wherein A is a poloyxyalkylene radical containing from about 1 to about 17 oxyalkylene groups wherein each oxyalkylene group contains from 2 to about 4 carbon atoms; B is a polyoxyalkylene amino radical containing from about 1 to 17 oxyalkylene groups where each oxyalkylene group contains from 2 to about 4 carbon atoms; R is a hydrocarbon radical having from 2 to 5 carbon atoms forming from 2 to 4 oxycarbon linkages with A and B; X is a C═O radical, a C═S radical or a radical derived from a difunctional isocyanate having two ##STR35## groups; c and d are from 1 to 3 chosen such that their sum is 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 in a molar ratio of about 1 mole of the substituted ureido forming compound for each mole of amine.
Claim 8
Dependent Claim
269 words
A polyether polyureide comprises a substituted ureido-terminated polyoxyalkylene material, formed by the reaction of a substituted ureido group forming compound with a compound selected from a polyoxyalkylenepolyamine of the formula ##STR33## wherein X' is a hydrogen, a methyl radical or an ethyl radical; Z is a hydrocarbon radical having from 2 to 5 carbon atoms forming from 2 to 4 external either linkages; n is a number from 1 to about 20 and r is a number from 2 to 4 and a polyoxyalkylene ureylene or thioureylene having terminal primary amino groups of the formula ##STR34## wherein A is a poloyxyalkylene radical containing from about 1 to about 17 oxyalkylene groups wherein each oxyalkylene group contains from 2 to about 4 carbon atoms; B is a polyoxyalkylene amino radical containing from about 1 to 17 oxyalkylene groups where each oxyalkylene group contains from 2 to about 4 carbon atoms; R is a hydrocarbon radical having from 2 to 5 carbon atoms forming from 2 to 4 oxycarbon linkages with A and B; X is a C═O radical, a C═S radical or a radical derived from a difunctional isocyanate having two ##STR35## groups; c and d are from 1 to 3 chosen such that their sum is 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 in a molar ratio of about 1 mole of the substituted ureido forming compound for each mole of amine.
Claim 9
Dependent Claim
24 words
The polyether polyureide of claim 6 wherein said substituted ureido group forming compound is selected from mono substituted isocyanates and mono and disubstituted ureas.
Claim 10
Dependent Claim
32 words
The polyether polyureide of claim 7 wherein X' is a methyl radical, n is a number from 2 to 17, Z is a 1,2-propylene radical and r is about 2 or 3.
Claim 11
Dependent Claim
119 words
The polyether polyureide of claim 7 wherein A corresponds to the formula: ##STR36## wherein n is a number from 0 to 16 and preferably a number from 1 to 10, B corresponds to the formula: ##STR37## wherein m is a number from 0 to 16 and preferably a number from 1 to 10, c and d are from 1 to 2 chosen such 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 C═O or C═S radical.
Claim 12
Dependent Claim
21 words
The polyether polyureide of claim 9 wherein X is the radical selected from a group consisting of ##STR38## and mixtures thereof.
Claim 13
Dependent Claim
27 words
The polyether polyureide of claim 9 wherein X is a mixture of C═O and C═S radicals throughout the formula such as to yield a mixed polyether ureylenethioureylene.
Claim 14
Dependent Claim
130 words
A polyether polyureide comprising a ureido-terminated polyoxyalkylene of the formula: ##STR39## wherein R 1 and R 2 are independently hydrogen, provided only one is hydrogen; or alkyl, alkenyl, alkadienyl, alkatrienyl radicals of from 1 to 20 carbon atoms; or aryl, alkaryl or aralkyl monocyclic, polycyclic, or fused ring aromatic radicals of from 6 to 30 carbon atoms; or R 1 and R 2 , taken together with the nitrogen atom to which each is attached, form a 5 or 6 membered heterocyclic ring; X' is 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 20; and, r is a number from 2 to 4.
Claim 15
Dependent Claim
130 words
A polyether polyureide comprising a ureido-terminated polyoxyalkylene of the formula: ##STR39## wherein R 1 and R 2 are independently hydrogen, provided only one is hydrogen; or alkyl, alkenyl, alkadienyl, alkatrienyl radicals of from 1 to 20 carbon atoms; or aryl, alkaryl or aralkyl monocyclic, polycyclic, or fused ring aromatic radicals of from 6 to 30 carbon atoms; or R 1 and R 2 , taken together with the nitrogen atom to which each is attached, form a 5 or 6 membered heterocyclic ring; X' is 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 20; and, r is a number from 2 to 4.
Claim 16
Dependent Claim
50 words
The polyether polyureide of claim 12 wherein X; is a methyl radical; n is a number from 2 to 17, Z is a 1,2-propylene radical and r, is about 2 or 3, R 1 and R 2 are alkyl radicals of from 1 to 4 carbon atoms; or monocyclic aryl.
Claim 17
Dependent Claim
22 words
The polyether polyureide of claim 13 wherein r is 2 and the ureido terminated polyoxyalkylene has a molecular weight of about 2000.
Claim 18
Dependent Claim
18 words
The polyether polyureide of claim 13 wherein the ureido terminated polyoxyalkylene has a molecular weight of about 400.
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) | 1981-09-18 | 1982-03-20 | 1982-09-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-09-18 | 1986-03-20 | 1986-09-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-09-18 | 1990-03-20 | 1990-09-19 | $7700.00 | Window Closed / Lapsed |