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US4154724A Expired / Lapsed US ⏱️ 0.0 years remaining

Polyether polyureides and resinous compositions therefrom

Assignee: Huntsman Corp
•
Filing: 1976-06-28
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Granted: 1979-05-15
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Expires: 1996-06-28
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Abstract

Abstract Novel polyether polyureides useful in the manufacture of plastics, sealants, molds, foams and coatings. The novel composition comprises a ureido-terminated polyoxyalkylene prepared by reacting a primary amine-terminated polyoxyalkylene with urea at temperatures in the range from about 120° C. to about 150° C. in a molar ratio of about one mole of urea for each terminal primary amino group.

Inventors

  • 👤 Heinz Schulze

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 17:15
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/48; C08G18/50; C08G18/5021; C07; C07C; C07C275/00; C07C275/04; C07C275/28; C08G65/00; C08G65/02; C08G65/32; C08G65/321; C08G65/325; C08G65/326; C08G65/338; C08G71/00; C08G71/02

Claims Analysis

Total Claims: 30
Claim 1
Independent Claim 206 words
A polyether polyureide comprising a ureido-terminated polyoxyalkylene selected from the group consisting of a compound of the formula: ##STR20## wherein 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: ##STR21## wherein 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 ##STR22## 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 206 words
A polyether polyureide comprising a ureido-terminated polyoxyalkylene selected from the group consisting of a compound of the formula: ##STR20## wherein 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: ##STR21## wherein 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 ##STR22## 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: ##STR23## wherein n is a number from 0 to 15; B corresponds to the formula: ##STR24## 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 ##STR25## and mixtures thereof.
Claim 7
Dependent Claim 279 words
A polyether polyureide comprises a ureido-terminated polyoxyalkylene material, formed by the reaction of a ureido group forming compound with a compound selected from a polyoxyalkylenepolyamine of the formula ##STR26## 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 ether 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 ##STR27## wherein A is a polyoxyalkylene 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 wherein 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 --NHC-- 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 ratio of about 1 mole of ureide forming compound for each terminal primary amine group at temperatures in the range of from about 120° C. to about 150° C.
Claim 8
Dependent Claim 279 words
A polyether polyureide comprises a ureido-terminated polyoxyalkylene material, formed by the reaction of a ureido group forming compound with a compound selected from a polyoxyalkylenepolyamine of the formula ##STR26## 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 ether 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 ##STR27## wherein A is a polyoxyalkylene 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 wherein 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 --NHC-- 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 ratio of about 1 mole of ureide forming compound for each terminal primary amine group at temperatures in the range of from about 120° C. to about 150° C.
Claim 9
Dependent Claim 33 words
The polyether polyureide of claim 6 wherein said ureido group forming compound is selected from urea and isocyanates of the general formula M + NCO - wherein M + is an alkali metal.
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: ##STR28## wherein n is a number from 0 to 16 and preferably a number from 1 to 10, B corresponds to the formula: ##STR29## 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 ##STR30## 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 59 words
A polyether polyureide comprising a ureidoterminated polyoxyalkylene of the formula: ##STR31## wherein 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 59 words
A polyether polyureide comprising a ureidoterminated polyoxyalkylene of the formula: ##STR31## wherein 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 32 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.
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.
Claim 19
Dependent Claim 105 words
A polyether polyureide formed by the reaction of a ureido group forming compound with a compound selected from a polyoxyalkylenepolyamine of the formula ##STR32## 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 ether linkages; n is a number from 1 to about 20 and r is a number from 2 to 4 wherein the ratio of said ureido group forming compound is one mole to each terminal primary amino group at temperatures in the range of about 120° C. to about 150° C.
Claim 20
Dependent Claim 105 words
A polyether polyureide formed by the reaction of a ureido group forming compound with a compound selected from a polyoxyalkylenepolyamine of the formula ##STR32## 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 ether linkages; n is a number from 1 to about 20 and r is a number from 2 to 4 wherein the ratio of said ureido group forming compound is one mole to each terminal primary amino group at temperatures in the range of about 120° C. to about 150° C.
Claim 21
Dependent Claim 32 words
The polyether polyureide of claim 16 wherein the ureido forming compound is selected from urea and isocyanates of the general formula M + NCO - wherein M + is an alkali metal.
Claim 22
Dependent Claim 40 words
The polyether polyureide of claim 17 wherein the ureido forming compound is urea and 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 23
Dependent Claim 20 words
The polyether polyureide of claim 18 wherein r is 2 and said polyoxyalkylenepolyamine has a molecular weight of about 2000.
Claim 24
Dependent Claim 16 words
The polyether polyureide of claim 18 wherein said polyoxyalkylenepolyamine has a molecular weight of about 400.
Claim 25
Independent Claim 105 words
A method for producing a polyether polyureide comprising the step of: reacting a 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 ether linkages; n is a number from 1 to about 20 and r is a number from 2 to 4 in a ratio of 1 mole of ureido group forming compound to each terminal amine group at temperatures in the range of 120° C. to 150° C.
Claim 26
Independent Claim 105 words
A method for producing a polyether polyureide comprising the step of: reacting a 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 ether linkages; n is a number from 1 to about 20 and r is a number from 2 to 4 in a ratio of 1 mole of ureido group forming compound to each terminal amine group at temperatures in the range of 120° C. to 150° C.
Claim 27
Dependent Claim 31 words
The method of claim 21 wherein the ureido forming compound is selected from urea and isocyanates of the general formula M + NCO - wherein M + is an alkali metal.
Claim 28
Dependent Claim 39 words
The method of claim 21 wherein the ureido forming compound is urea and 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 29
Dependent Claim 19 words
The method of claim 23 wherein r is 2 and said polyoxyalkylenepolyamine has a molecular weight of about 2000.
Claim 30
Dependent Claim 15 words
The method of claim 23 wherein said polyoxyalkylenepolyamine has a molecular weight of about 400.

References Cited (Backward Citations)

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CA717151A Cited
US3080343A Cited
GB981813A Cited
GB1104209A Cited
US3704321A Cited
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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) 1982-05-14 1982-11-13 1983-05-15 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-05-14 1986-11-13 1987-05-15 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-05-14 1990-11-13 1991-05-15 $7700.00 Window Closed / Lapsed

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