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US4201852A Expired / Lapsed US ⏱️ 0.0 years remaining

Polyurethanes based on modified polyisocyanates containing sulphonic acid ester groups and process for the production thereof

Assignee: Bayer AG
•
Filing: 1977-11-03
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Granted: 1980-05-06
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Expires: 1997-11-03
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Abstract

Abstract The instant invention is directed to novel modified polyisocyanates which contain sulphonic acid ester groups and to the method of manufacture thereof. The polyisocyanates of the instant invention are produced by reacting isocyanatoaryl sulphonic acids with oxiranes and/or oxetanes. The resultant products are highly useful in the production of polyurethane resins.

Inventors

  • 👤 Dieter Dieterich

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 04:44
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/72; C08G18/77; C08G18/775; C08G18/78; C08G18/79; C08G18/798

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 128 words
A process for the preparation of modified polyisocyanates containing sulphonic acid alkyl ester groups, which may contain the isocyanate groups at least partly in dimerized form, characterized in that isocyanatoaryl sulphonic acids which contain at least two isocyanate groups and in which the isocyanate groups may be at least partly in dimerized form, are reacted with oxiranes and/or oxetanes at temperatures of from 0° to 190° C., the nature and proportions of the reactants being chosen so that the equivalent ratio of the total quantity of isocyanate groups, including the isocyanate groups which may be present in dimerized form, to the quantity of sulphonic acid groups is greater than 1 and the equivalent ratio of oxirane and/or oxetane groups to sulphonic acid groups is from 0.1:1 to 10:1.
Claim 2
Dependent Claim 128 words
A process for the preparation of modified polyisocyanates containing sulphonic acid alkyl ester groups, which may contain the isocyanate groups at least partly in dimerized form, characterized in that isocyanatoaryl sulphonic acids which contain at least two isocyanate groups and in which the isocyanate groups may be at least partly in dimerized form, are reacted with oxiranes and/or oxetanes at temperatures of from 0° to 190° C., the nature and proportions of the reactants being chosen so that the equivalent ratio of the total quantity of isocyanate groups, including the isocyanate groups which may be present in dimerized form, to the quantity of sulphonic acid groups is greater than 1 and the equivalent ratio of oxirane and/or oxetane groups to sulphonic acid groups is from 0.1:1 to 10:1.
Claim 3
Dependent Claim 58 words
The process of claim 1, wherein the aromatic polyisocyanates containing sulphonic acid ester groups are prepared by sulphonating aromatic polyisocyanates in known manner in a first reaction step and the polyisocyanate mixture obtained from this sulphonation, which mixture consists at least partly of isocyanatoaryl sulphonic acids, is reacted with oxiranes and/or oxetanes without being first isolated or purified.
Claim 4
Dependent Claim 22 words
The process of claim 1, wherein mono- and/or poly-isocyanates which are free from sulphonic acid groups are included in the reaction mixture.
Claim 5
Dependent Claim 21 words
The process of claim 1, wherein the equivalent ratio of isocyanate groups to sulphonic acid groups is from 1.05:1 to 50:1.
Claim 6
Dependent Claim 21 words
The process of claim 4, wherein the equivalent ratio of isocyanate groups to sulphonic acid groups is from 2:1 to 30:1.
Claim 7
Dependent Claim 23 words
The process of claim 4, wherein the equivalent ratio of oxirane and/or oxetane groups to sulphonic acid groups is from 0.6:1 to 2:1.
Claim 8
Dependent Claim 19 words
The process of claim 6, wherein the reaction is conducted at a temperature of from 20° to 140° C.
Claim 9
Dependent Claim 129 words
Polyisocyanate mixtures characterized as containing: (a) from about 4 to about 48%, by weight, of isocyanate groups, which may be partly in dimerized form; (b) from about 0.3 to about 38%, by weight, of groups of the formula --SO 2 --O-- forming part of an aryl sulphonic acid alkyl ester group; (c) from 0 to about 36%, by weight, of SO 3 H groups; (d) from 0 to about 25%, by weight, of urethane groups --NH--CO--O--; and (e) from 0 to about 28%, by weight, of allophanate groups ##STR12## the groups mentioned under (d) and (e) together amounting to from at least 0.4%, by weight, to not more than 28%, by weight, and the groups mentioned under (b) and (c) together amounting to not more than 38%, by weight.
Claim 10
Dependent Claim 129 words
Polyisocyanate mixtures characterized as containing: (a) from about 4 to about 48%, by weight, of isocyanate groups, which may be partly in dimerized form; (b) from about 0.3 to about 38%, by weight, of groups of the formula --SO 2 --O-- forming part of an aryl sulphonic acid alkyl ester group; (c) from 0 to about 36%, by weight, of SO 3 H groups; (d) from 0 to about 25%, by weight, of urethane groups --NH--CO--O--; and (e) from 0 to about 28%, by weight, of allophanate groups ##STR12## the groups mentioned under (d) and (e) together amounting to from at least 0.4%, by weight, to not more than 28%, by weight, and the groups mentioned under (b) and (c) together amounting to not more than 38%, by weight.
Claim 11
Dependent Claim 61 words
The mixtures of claim 8, wherein: Component (a) comprises from about 10 to about 40% by weight; Component (b) comprises from about 0.6 to about 28% by weight; Component (c) comprises from 0 to about 10% by weight: Component (d) comprises from about 0.2 to about 20% by weight; and Component (e) comprises from about 0.2 to about 20% by weight.
Claim 12
Dependent Claim 148 words
In the production of oligomeric or polymeric polyaddition products comprising reacting organic polyisocyanates with active hydrogen containing materials, the improvement wherein said polyisocyanate comprises (a) from about 4 to about 48%, by weight, of isocyanate groups, which may be partly in dimerized form; (b) from about 0.3 to about 38%, by weight, of groups of the formula --SO 2 --O-- forming part of an aryl sulphonic acid alkyl ester group; (c) from 0 to about 36%, by weight, of SO 3 H groups; (d) from 0 to about 25%, by weight, of urethane groups --NH--CO--O--; and (e) from 0 to about 28%, by weight, of allophanate groups ##STR13## the groups mentioned under (d) and (e) together amounting to from at least 0.4%, by weight, to not more than 28%, by weight, and the groups mentioned under (b) and (c) together amounting to not more than 38%, by weight.
Claim 13
Dependent Claim 148 words
In the production of oligomeric or polymeric polyaddition products comprising reacting organic polyisocyanates with active hydrogen containing materials, the improvement wherein said polyisocyanate comprises (a) from about 4 to about 48%, by weight, of isocyanate groups, which may be partly in dimerized form; (b) from about 0.3 to about 38%, by weight, of groups of the formula --SO 2 --O-- forming part of an aryl sulphonic acid alkyl ester group; (c) from 0 to about 36%, by weight, of SO 3 H groups; (d) from 0 to about 25%, by weight, of urethane groups --NH--CO--O--; and (e) from 0 to about 28%, by weight, of allophanate groups ##STR13## the groups mentioned under (d) and (e) together amounting to from at least 0.4%, by weight, to not more than 28%, by weight, and the groups mentioned under (b) and (c) together amounting to not more than 38%, by weight.

References Cited (Backward Citations)

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USB414266I5 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) 1983-05-06 1983-11-05 1984-05-06 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1987-05-06 1987-11-05 1988-05-06 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1991-05-06 1991-11-05 1992-05-06 $7700.00 Window Closed / Lapsed

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