US3971764A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for producing a cationic polyurethane
Assignee: Akzona Inc
•
Filing: 1974-12-26
•
Granted: 1976-07-27
•
Expires: 1994-12-26
Abstract
Abstract Cationic polyurethanes and a process for their production wherein a polyisocyanate, preferably a diisocyanate such as 2,4- or 2,6-tolylene-diisocyanate is reacted with an aliphatic dihydroxy compound substituted with an aliphatic side-chain of at least 10 carbon atoms to form a preliminary adduct or so-called prepolymer with terminal - NCO groups. This prepolymer is then reacted for chain-lengthening with an aliphatic monomeric diol (A) containing a tertiary nitrogen atom convertible into an ammonium compound or an aliphatic monomeric diol (B) containing a tertiary nitrogen atom already converted into an ammonium compound. The new cationic polyurethanes are especially useful as sizing agents for the sizing of paper.
Inventors
- 👤 Horst Schurmann
- 👤 Josef Bung
- 👤 Hendrikus Alouisius Van Aalten
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 15:26
CPC Classifications
D; D21; D21H; D21H17/00; D21H17/20; D21H17/33; D21H17/46; D21H17/54; D21H17/57; C; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/0804; C08G18/0809; C08G18/0814; C08G18/10; C08G18/28; C08G18/30; C08G18/36; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31551; Y10T428/31591
Claims Analysis
Total Claims: 27
Claim 1
Independent Claim
89 words
A process for the production of a cationic polyurethane which comprises: converting a monomeric aliphatic dihydroxy compound substituted with an aliphatic side-chain of at least 10 carbon atoms, by reaction with a polyisocyanate into a preliminary adduct with terminal --NCO groups; and chain-lengthening said adduct by reacting the terminal --NCO groups with A. an aliphatic monomeric diol containing a tertiary nitrogen atom which is subsequently converted into the corresponding ammonium compound, or B. an aliphatic monomeric diol containing a tertiary nitrogen atom previously converted into the corresponding ammonium compound.
Claim 2
Dependent Claim
89 words
A process for the production of a cationic polyurethane which comprises: converting a monomeric aliphatic dihydroxy compound substituted with an aliphatic side-chain of at least 10 carbon atoms, by reaction with a polyisocyanate into a preliminary adduct with terminal --NCO groups; and chain-lengthening said adduct by reacting the terminal --NCO groups with A. an aliphatic monomeric diol containing a tertiary nitrogen atom which is subsequently converted into the corresponding ammonium compound, or B. an aliphatic monomeric diol containing a tertiary nitrogen atom previously converted into the corresponding ammonium compound.
Claim 3
Dependent Claim
22 words
A process as claimed in claim 1 wherein said aliphatic side-chain substituent of the dihydroxy compound contains at least 16 carbon atoms.
Claim 4
Dependent Claim
19 words
A process as claimed in claim 1 wherein said monomeric aliphatic dihydroxy compound is a glycerol fatty acid monoester.
Claim 5
Dependent Claim
13 words
A process as claimed in claim 3 wherein said monoester is glycerol monostearate.
Claim 6
Dependent Claim
17 words
A process as claimed in claim 3 wherein said monoester is the behenic acid monoester of glycerol.
Claim 7
Dependent Claim
33 words
A process as claimed in claim 1 wherein the monomeric aliphatic dihydroxy compound is one in which the two hydroxy groups are connected by an aliphatic chain of not more than 7 atoms.
Claim 8
Dependent Claim
49 words
A process as claimed in claim 6 wherein said aliphatic chain as from 2 to 7 atoms and is selected from the group consisting of alkylene and dialkyleneamine with the side-chain being alkyl connected to a carbon atom of said alkylene or to the nitrogen atom of said dialkyleneamine.
Claim 9
Dependent Claim
15 words
A process as claimed in claim 1 wherein said monomeric aliphatic dihydroxy compound is N-stearyl-diethanolamine.
Claim 10
Dependent Claim
17 words
A process as claimed in claim 1 wherein said monomeric aliphatic dihydroxy compound is 1,2- or 1,4-dihydroxyoctadecane.
Claim 11
Dependent Claim
17 words
A process as claimed in claim 1 wherein hydrogen chloride is used to form the ammonium compound.
Claim 12
Dependent Claim
19 words
A process as claimed in claim 1 wherein said aliphatic monomeric diol containing a tertiary nitrogen atom is N-methyl-diethanolamine.
Claim 13
Dependent Claim
19 words
A process as claimed in claim 1 wherein said aliphatic monomeric diol containing a tertiary nitrogen atom is 1,2-propanediol-3-dimethylamine.
Claim 14
Dependent Claim
18 words
A process as claimed in claim 1 wherein the cationic polyurethane is produced in acetone as a solvent.
Claim 15
Dependent Claim
26 words
A process as claimed in claim 1 wherein the chain-lengthened product obtained with the diol (A) is first dried before being converted into said ammonium compound.
Claim 16
Dependent Claim
11 words
The cationic polyurethane product obtained by the process of claim 1.
Claim 17
Dependent Claim
107 words
A cationic polyurethane consisting essentially of the structural units of the formula ABAD in which: A is CO-NH-R-NH-CO, R being the hydrocarbon radical of a diisocyanate; B is a member selected from the group consisting of ##EQU4## n being an integer of from 9 to 21 and m being an integer of from 10 to 22; and D is a member selected from the group consisting of ##EQU5## R' being lower alkyl of 1 to 4 carbon atoms, r and s each being an integer of 2 to 6 and r + s being not more than 6 and X - being the anion of an acid.
Claim 18
Dependent Claim
107 words
A cationic polyurethane consisting essentially of the structural units of the formula ABAD in which: A is CO-NH-R-NH-CO, R being the hydrocarbon radical of a diisocyanate; B is a member selected from the group consisting of ##EQU4## n being an integer of from 9 to 21 and m being an integer of from 10 to 22; and D is a member selected from the group consisting of ##EQU5## R' being lower alkyl of 1 to 4 carbon atoms, r and s each being an integer of 2 to 6 and r + s being not more than 6 and X - being the anion of an acid.
Claim 19
Dependent Claim
37 words
A cationic polyurethane as claimed in claim 16 wherein n is an integer of 15 to 21, m is an integer of 16 to 22, and r and s each denotes an integer of 2 to 3.
Claim 20
Dependent Claim
14 words
A cationic polyurethane as claimed in claim 16 wherein R is 2,4- or 2,6-tolylene.
Claim 21
Dependent Claim
19 words
A paper sizing composition in which the essential sizing agent is the cationic polyurethane as claimed in claim 16.
Claim 22
Dependent Claim
20 words
A cationic polyurethane as claimed in claim 16 having a molecular weight in the range of about 3,000 to 20,000.
Claim 23
Dependent Claim
45 words
A cationic polyurethane as claimed in claim 16 wherein the diisocyanate of the radical R consists essentially of a mixture of toluene-diisocyanate - (2,4) and - (2,6), B is the member ##EQU6## n being 17, D has the same meaning as given in claim 16.
Claim 24
Dependent Claim
72 words
A process for making a cationic polyurethane which comprises reacting a monomeric aliphatic dihydroxy compound substitued with an aliphatic side-chain of at least 10 carbon atoms, an organic polyisocyanate and (1) an aliphatic monomeric diol containing a tertiary nitrogen atom and subsequently converting the tertiary nitrogen atom into the corresponding ammonium compound; or (2) an aliphatic monomeric diol which contains a nitrogen atom which has been converted into the corresponding ammonium compound.
Claim 25
Dependent Claim
72 words
A process for making a cationic polyurethane which comprises reacting a monomeric aliphatic dihydroxy compound substitued with an aliphatic side-chain of at least 10 carbon atoms, an organic polyisocyanate and (1) an aliphatic monomeric diol containing a tertiary nitrogen atom and subsequently converting the tertiary nitrogen atom into the corresponding ammonium compound; or (2) an aliphatic monomeric diol which contains a nitrogen atom which has been converted into the corresponding ammonium compound.
Claim 26
Dependent Claim
62 words
The process of claim 22 wherein the said substituted monomeric aliphatic dihydroxy compound has 2 to 7 carbon atoms in its main chain, the organic polyisocyanate is a diisocyanate, and the diol (1) or (2) has only one or two tertiary nitrogen atoms or corresponding ammonium compounds which are in the main chain at a point removed from between the hydroxyl groups.
Claim 27
Dependent Claim
10 words
A cationic polyurethane prepared by the process of claim 23.
References Cited (Backward Citations)
US3480592A
Cited
US3479310A
Cited
US3491050A
Cited
US3436361A
Cited
US3499852A
Cited
US3637540A
Cited
US3792023A
Cited
US3726838A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-07-27 | 1980-01-26 | 1980-07-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-07-27 | 1984-01-26 | 1984-07-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-07-27 | 1988-01-26 | 1988-07-27 | $7700.00 | Window Closed / Lapsed |