US4237250A
Expired / Lapsed
US
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Polyurethanes containing aryl sulfonic acid alkyl ester groups
Assignee: Bayer AG
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Filing: 1978-07-31
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Granted: 1980-12-02
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Expires: 1998-07-31
Abstract
Abstract The instant invention is directed to polyurethanes containing sulfonic acid ester groups wherein arylsulfonic acid alkyl ester groups are attached to aromatic nuclei as chain members and to their method of preparation. The process is characterized by reacting at from 0° to 190° C. (A) aromatic isocyanatosulfonic acids; with (B) oxiranes and/or oxetanes wherein the equivalent ratio of NCO groups to SO 3 H groups is from 0.1:1 to 1.99:1 and the equivalent ratio of epoxide (and/or oxetane) groups to SO 3 H groups is from 0.2:1 to 5:1. The invention is also directed to the product by process.
Inventors
- 👤 Dieter Dieterich
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 02:45
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/72; C08G18/77; C08G18/775; C08G18/71; C08G18/715
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
71 words
Polyurethanes having a molecular weight above 12,000 and containing arylsulfonic acid alkyl ester groups produced by reacting at from 0° to 190° C. (a) aromatic polyisocyanatosulfonic acids with (b) oxiranes or oxetanes wherein the equivalent ratio of isocyanate groups (including dimerized isocyanate) to sulfonic acid groups is from 0.1:1 to 1:1 and the equivalent ratio of epoxide, oxetane and mixtures thereof groups to sulfonic acid groups is from 0.2:1 to 5:1.
Claim 2
Dependent Claim
71 words
Polyurethanes having a molecular weight above 12,000 and containing arylsulfonic acid alkyl ester groups produced by reacting at from 0° to 190° C. (a) aromatic polyisocyanatosulfonic acids with (b) oxiranes or oxetanes wherein the equivalent ratio of isocyanate groups (including dimerized isocyanate) to sulfonic acid groups is from 0.1:1 to 1:1 and the equivalent ratio of epoxide, oxetane and mixtures thereof groups to sulfonic acid groups is from 0.2:1 to 5:1.
Claim 3
Dependent Claim
12 words
The polyurethanes of claim 1, comprising polyether, polyester units or mixtures thereof.
Claim 4
Dependent Claim
24 words
The polyurethanes of claim 1, comprising arylsulfonic acid alkyl ester groups of the formula: ##STR8## wherein Ar represents a residue of an aromatic isocyanate.
Claim 5
Dependent Claim
26 words
The polyurethanes of claim 3, wherein said arylsulfonic acid alkyl ester groups are of the formula: ##STR9## wherein Ar represents a residue of an aromatic isocyanate.
Claim 6
Dependent Claim
79 words
A process for the preparation of polyurethanes having a number average molecular weight above 12,000 and containing arylsulfonic acid alkyl ester groups, comprising: reacting at from 0° to 190° C. (a) aromatic isocyanatosulfonic acids; with (b) oxiranes, oxetanes and mixtures thereof wherein the equivalent ratio of NCO groups to SO 3 H groups is from 0.2:1 to 1:1 and the equivalent ratio of epoxide, ocetane and mixtures thereof groups to SO 3 H groups is from 0.2:1 to 5:1.
Claim 7
Dependent Claim
79 words
A process for the preparation of polyurethanes having a number average molecular weight above 12,000 and containing arylsulfonic acid alkyl ester groups, comprising: reacting at from 0° to 190° C. (a) aromatic isocyanatosulfonic acids; with (b) oxiranes, oxetanes and mixtures thereof wherein the equivalent ratio of NCO groups to SO 3 H groups is from 0.2:1 to 1:1 and the equivalent ratio of epoxide, ocetane and mixtures thereof groups to SO 3 H groups is from 0.2:1 to 5:1.
Claim 8
Dependent Claim
39 words
The process of claim 5, wherein said equivalent ratio of NCO groups to SO 3 H groups is from 0.2:1 to 1:1 and said equivalent ratio of epoxide groups to SO 3 H groups is from 0.5:1 to 2:1.
Claim 9
Dependent Claim
17 words
The process of claim 5, wherein said aromatic isocyanatosulfonic acids contain polyether, polyester units or mixtures thereof.
Claim 10
Dependent Claim
24 words
The process of claim 5, wherein components (A) and (B) are reacted in the presence of: (C) ether polyols, polyester polyols and mixtures thereof.
Claim 11
Dependent Claim
31 words
The process of claim 5, wherein component (A) is selected from the group consisting of the dimeric forms of mono- and di-sulfonic acids of 4,4'-diisocyanato-diphenylmethane, 2,4-diisocyanato-diphenylmethane, 2,4-diisocyantotoluene, 2,6-diisocyanatotoluene and mixtures thereof.
Claim 12
Dependent Claim
12 words
The process of claim 5, wherein component (B) is a polyglycidyl ether.
Claim 13
Dependent Claim
24 words
The process of claim 10, wherein said polyglycidyl ether is of the formula: ##STR10## wherein n is an integer of from 0 to 1,000.
Claim 14
Dependent Claim
16 words
The process of claim 5, wherein component (B) is a triglycidyl isocyanurate of the formula: ##STR11##
Claim 15
Dependent Claim
10 words
The process of claim 5, wherein component (B) is N,N'-diglycidyl-dimethylhydantoin.
Claim 16
Dependent Claim
17 words
The process of claim 5, wherein component (B) is a polyglycidyl ether of bis-(-p-hydroxyphenyl)-dimethyl methane (bis-phenol A).
Claim 17
Dependent Claim
101 words
A procss for the preparation of polyurethanes having a number average molecular weight above 12,000 and containing aryl sulfonic acid alkyl ester groups, comprising: reacting at from 0° to 190° C. (a) aromatic isocyanatosulfonic acids; with (b) oxiranes, oxetanes and mixtures thereof wherein the equivalent ratio of NCO groups to SO 3 H groups is from 0.1:1 to 1.99:1 and the equivalent ratio of epoxide, oxetane and mixtures thereof groups to SO 3 H groups is from 0.2:1 to 5:1 provided that when there is an NCO excess, Zerewitinoff-active compounds are also used in an amount which corresponds to said excess.
Claim 18
Dependent Claim
101 words
A procss for the preparation of polyurethanes having a number average molecular weight above 12,000 and containing aryl sulfonic acid alkyl ester groups, comprising: reacting at from 0° to 190° C. (a) aromatic isocyanatosulfonic acids; with (b) oxiranes, oxetanes and mixtures thereof wherein the equivalent ratio of NCO groups to SO 3 H groups is from 0.1:1 to 1.99:1 and the equivalent ratio of epoxide, oxetane and mixtures thereof groups to SO 3 H groups is from 0.2:1 to 5:1 provided that when there is an NCO excess, Zerewitinoff-active compounds are also used in an amount which corresponds to said excess.
Claim 19
Dependent Claim
92 words
Polyurethanes having a molecular weight above 12,000 and containing arylsulfonic acid alkyl ester groups produced by reacting at from 0° to 190° C. (a) aromatic polyisocyanatosulfonic acids with (b) oxiranes or oxetanes wherein the equivalent ratio of isocyanate groups (including dimerized isocyanate) to sulfonic acid groups is from 0.1:1 to 1.99:1 and the equivalent ratio of epoxide, oxetane and mixtures thereof groups to sulfonic acid groups is from 0.2:1 to 5:1, provided that when there is an NCO excess, Zerewitinoff-active compounds are also used in an amount which corresponds to said excess.
Claim 20
Dependent Claim
92 words
Polyurethanes having a molecular weight above 12,000 and containing arylsulfonic acid alkyl ester groups produced by reacting at from 0° to 190° C. (a) aromatic polyisocyanatosulfonic acids with (b) oxiranes or oxetanes wherein the equivalent ratio of isocyanate groups (including dimerized isocyanate) to sulfonic acid groups is from 0.1:1 to 1.99:1 and the equivalent ratio of epoxide, oxetane and mixtures thereof groups to sulfonic acid groups is from 0.2:1 to 5:1, provided that when there is an NCO excess, Zerewitinoff-active compounds are also used in an amount which corresponds to said excess.
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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) | 1983-12-02 | 1984-06-02 | 1984-12-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-12-02 | 1988-06-02 | 1988-12-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-12-02 | 1992-06-02 | 1992-12-02 | $7700.00 | Window Closed / Lapsed |