US4499233A
Expired / Lapsed
US
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Water dispersible, modified polyurethane and a thickened aqueous composition containing it
Assignee: Elementis Specialties Inc
•
Filing: 1983-05-03
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Granted: 1985-02-12
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Expires: 2003-05-03
Abstract
Abstract A water dispersible, modified polyurethane which is the reaction product of polyisocyanate, polyether polyol, modifying agent containing at least two active hydrogen moieties and capping agent. The modified polyurethane is preferably prepared by reacting the polyisocyanate, the polyether polyol and the modifying agent and then adding the capping agent. The modified polyurethane resists microbial attack, exhibits superior efficiency in thickening aqueous compositions and imparts improved leveling. Included among the modifying agents are ethylene diamine, 1,6-diaminohexane, 1,10-diaminodecane, N-phenyl-p-phenylenediamine, succinic acid, suberic acid, sebacic acid, 1,10-decanedicarboxylic acid, 1,4-benzene-dicarboxylic acid, ethanolamine, 2-(ethylamino)ethanol, and p-carboxyphenol and mixtures thereof.
Inventors
- 👤 Marvin T. Tetenbaum
- 👤 Burlon C. Crowley
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 01:52
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/71; C08G18/08; C08G18/10; C08G18/12; C08G18/28; C08G18/2805; C08G18/65; C08G18/66; C08G18/6666; C08G18/6692; Y; Y10; Y10S; Y10S528/00; Y10S528/904
Claims Analysis
Total Claims: 35
Claim 1
Independent Claim
229 words
A water dispersible modified polyurethane which is the product of a reaction conducted under substantially anhydrous conditions of: (a) polyisocyanate; (b) polyether polyol in an amount ranging from about 0.10 to about 10.00 moles per mole of polyisocyanate; (c) modifying agent in an amount ranging from about 0.015 to about 3.400 moles per mole of polyisocyanate, said modifying agent having the formula X.sub.x --R--Y.sub.y wherein R represents a group containing from 0 to 10 carbon atoms, X is a group containing at least one active hydrogen moiety selected from the group consisting of primary amino, secondary amino, carboxyl and mixtures thereof, Y is a group containing at least one active hydrogen moiety selected from the group consisting of primary amino, secondary amino, carboxyl, hydroxyl, mercapto and mixtures thereof, the sum of (x+y) is an integer greater than 1 and x is at least 1 wherein the modifying agent is composed of less than about 20 mole % of compounds wherein the sum of (x+y) is at least 3 and wherein the polyisocyanate, the polyether polyol and the modifying agent are used to form the polymer chain; and (d) capping agent which is reactive with the reaction product of the polyisocyanate, the polyether polyol and the modifying agent and which is present in an amount sufficient to cap the reaction product of the polyisocyanate, polyether polyol and the modifying agent.
Claim 2
Dependent Claim
229 words
A water dispersible modified polyurethane which is the product of a reaction conducted under substantially anhydrous conditions of: (a) polyisocyanate; (b) polyether polyol in an amount ranging from about 0.10 to about 10.00 moles per mole of polyisocyanate; (c) modifying agent in an amount ranging from about 0.015 to about 3.400 moles per mole of polyisocyanate, said modifying agent having the formula X.sub.x --R--Y.sub.y wherein R represents a group containing from 0 to 10 carbon atoms, X is a group containing at least one active hydrogen moiety selected from the group consisting of primary amino, secondary amino, carboxyl and mixtures thereof, Y is a group containing at least one active hydrogen moiety selected from the group consisting of primary amino, secondary amino, carboxyl, hydroxyl, mercapto and mixtures thereof, the sum of (x+y) is an integer greater than 1 and x is at least 1 wherein the modifying agent is composed of less than about 20 mole % of compounds wherein the sum of (x+y) is at least 3 and wherein the polyisocyanate, the polyether polyol and the modifying agent are used to form the polymer chain; and (d) capping agent which is reactive with the reaction product of the polyisocyanate, the polyether polyol and the modifying agent and which is present in an amount sufficient to cap the reaction product of the polyisocyanate, polyether polyol and the modifying agent.
Claim 3
Dependent Claim
26 words
The water dispersible, modified polyurethane of claim 1 wherein the polyisocyanate is composed of less than about 20 mole % of tri and higher functional polyisocyanates.
Claim 4
Dependent Claim
29 words
The water dispersible, modified polyurethane of claim 1 wherein the polyisocyanate is selected from the group consisting of 1,6-hexamethylene diisocyanate, 1-isocyanato-3-isocyanato-methyl-3,5,5-trimethyl cyclohexane, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate and mixtures thereof.
Claim 5
Dependent Claim
29 words
The water dispersible, modified polyurethane of claim 1 wherein the polyether polyol is present in an amount ranging from about 0.50 to about 5.00 moles per mole of polyisocyanate.
Claim 6
Dependent Claim
24 words
The water dispersible, modified polyurethane of claim 1 wherein the average molecular weight of the polyether polyol is from about 4,000 to about 20,000.
Claim 7
Dependent Claim
55 words
The water dispersible, modified polyurethane of claim 1 wherein the polyether polyol is a homopolymer or a block or random copolymer having the repeating unit: ##STR2## wherein R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of H, CH 3 and C 2 H 5 .
Claim 8
Dependent Claim
26 words
The water dispersible, modified polyurethane of claim 1 wherein the polyether polyol is composed of less than about 50% equivalent % of three-dimensional polymer forming material.
Claim 9
Dependent Claim
29 words
The water dispersible, modified polyurethane of claim 1 wherein the modifying agent is present in an amount ranging from about 0.025 to about 1.000 moles per mole of polyisocyanate.
Claim 10
Dependent Claim
32 words
The water dispersible, modified polyurethane of claim 1 wherein the modifying agent is composed of less than about 10 mole % of compounds wherein the sum of (x+y) is at least 3.
Claim 11
Dependent Claim
27 words
The water dispersible, modified polyurethane of claim 1 wherein the modifying agent is selected from the group consisting α, ω-diaminoalkanes, dicarboxylic acids, aminocarboxylic acids and mixtures thereof.
Claim 12
Dependent Claim
29 words
The water dispersible, modified polyurethane of claim 1 wherein the capping agent is present in an amount ranging from about 0.10 to about 10.00 moles per mole of polyisocyanate.
Claim 13
Dependent Claim
15 words
The water dispersible, modified polyurethane of claim 1 wherein the capping agent is a monoisocyanate.
Claim 14
Dependent Claim
188 words
A water dispersible, modified polyurethane which is the product of a reaction conducted under substantially anhydrous conditions of: (a) polyisocyanate selected from the group consisting of 1,6-hexamethylene diisocyanate, 1-isocyanato-3-isocyanatomethyl-3,5,5-trimethylcyclohexane, 2,6-tolylene diisocyanate, 2,4-tolylene diisocyanate and mixtures thereof; (b) polyether polyol in an amount ranging from about 0.10 to about 10.00 moles per mole of polyisocyanate, said polyether polyol having an average molecular weight in the range of from about 4,000 to about 20,000 and having the repeating unit ##STR3## wherein R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of H, CH 3 and C 2 H 5 ; (c) modifying agent in an amount ranging from about 0.015 to about 3,400 moles per mole of polyisocyanate, said modifying agent being selected from the group consisting of α, ω-diaminoalkanes, dicarboxylic acids, aminocarboxylic acids, and mixtures thereof; and (d) capping agent which is reactive with the reaction product of the polyisocyanate, the polyether polyol and the modifying agent and which is present in an amount sufficient to cap the reaction product of the polyisocyanate, the polyether polyol and the modifying agent.
Claim 15
Dependent Claim
188 words
A water dispersible, modified polyurethane which is the product of a reaction conducted under substantially anhydrous conditions of: (a) polyisocyanate selected from the group consisting of 1,6-hexamethylene diisocyanate, 1-isocyanato-3-isocyanatomethyl-3,5,5-trimethylcyclohexane, 2,6-tolylene diisocyanate, 2,4-tolylene diisocyanate and mixtures thereof; (b) polyether polyol in an amount ranging from about 0.10 to about 10.00 moles per mole of polyisocyanate, said polyether polyol having an average molecular weight in the range of from about 4,000 to about 20,000 and having the repeating unit ##STR3## wherein R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of H, CH 3 and C 2 H 5 ; (c) modifying agent in an amount ranging from about 0.015 to about 3,400 moles per mole of polyisocyanate, said modifying agent being selected from the group consisting of α, ω-diaminoalkanes, dicarboxylic acids, aminocarboxylic acids, and mixtures thereof; and (d) capping agent which is reactive with the reaction product of the polyisocyanate, the polyether polyol and the modifying agent and which is present in an amount sufficient to cap the reaction product of the polyisocyanate, the polyether polyol and the modifying agent.
Claim 16
Dependent Claim
20 words
The water dispersible modified polyurethane of claim 13 wherein the polyisocyanate is a mixture of 2,4-tolylene diisocyanate and 2,6-tolylene diisocyanate.
Claim 17
Dependent Claim
46 words
The water dispersible modified polyurethane of claim 13 wherein the polyether polyol is present in an amount ranging from about 0.50 to about 5.00 moles per mole of the polyisocyanate and has an average molecular weight in the range of from about 4,000 to about 14,000.
Claim 18
Dependent Claim
15 words
The water dispersible modified polyurethane of claim 15 wherein the polyether polyol is polyethylene glycol.
Claim 19
Dependent Claim
19 words
The water dispersible modified polyurethane of claim 13 wherein the modifying agent is ethylenediamine, succinic acid or mixtures thereof.
Claim 20
Dependent Claim
15 words
The water dispersible modified polyurethane of claim 13 wherein the capping agent is a monoisocyanate.
Claim 21
Dependent Claim
14 words
The water dispersible modified polyurethane of claim 18 wherein the capping agent is 1-isocyanatooctadecane.
Claim 22
Dependent Claim
248 words
A thickened aqueous composition comprising: (a) water; and (b) from about 0.005 to about 10.00% by weight of a water dispersible, modified polyurethane which is the product of a reaction conducted under substantially anhydrous conditions of: (i) polyisocyanate; (ii) polyether polyol in an amount ranging from about 0.10 to about 10.00 moles per mole of polyisocyanate; (iii) modifying agent in an amount ranging from about 0.015 to about 3.400 moles per mole of polyisocyanate, said modifying agent having the formula X.sub.x --R--Y.sub.y wherein R represents a group containing from 0 to 10 carbon atoms, X is a group containing at least one active hydrogen moiety selected from the group consisting of primary amino, secondary amino, carboxyl and mixtures thereof, Y is a group containing at least one active hydrogen moiety selected from the group consisting of primary amino, secondary amino, carboxyl, hydroxyl, mercapto and mixtures thereof, the sum of (x+y) is an integer greater than 1 and x is at least 1 wherein the modifying agent is composed of less than about 20 mole % of compounds wherein the sum of (x+y) is at least 3 and wherein the polyisocyanate, the polyether polyol and the modifying agent are used to form the polymer chain; and (iv) capping agent which is reactive with the reaction product of the polyisocyanate, the polyether polyol and the modifying agent and which is present in an amount sufficient to cap the reaction product of the polyisocyanate, the polyether polyol and the modifying agent.
Claim 23
Dependent Claim
248 words
A thickened aqueous composition comprising: (a) water; and (b) from about 0.005 to about 10.00% by weight of a water dispersible, modified polyurethane which is the product of a reaction conducted under substantially anhydrous conditions of: (i) polyisocyanate; (ii) polyether polyol in an amount ranging from about 0.10 to about 10.00 moles per mole of polyisocyanate; (iii) modifying agent in an amount ranging from about 0.015 to about 3.400 moles per mole of polyisocyanate, said modifying agent having the formula X.sub.x --R--Y.sub.y wherein R represents a group containing from 0 to 10 carbon atoms, X is a group containing at least one active hydrogen moiety selected from the group consisting of primary amino, secondary amino, carboxyl and mixtures thereof, Y is a group containing at least one active hydrogen moiety selected from the group consisting of primary amino, secondary amino, carboxyl, hydroxyl, mercapto and mixtures thereof, the sum of (x+y) is an integer greater than 1 and x is at least 1 wherein the modifying agent is composed of less than about 20 mole % of compounds wherein the sum of (x+y) is at least 3 and wherein the polyisocyanate, the polyether polyol and the modifying agent are used to form the polymer chain; and (iv) capping agent which is reactive with the reaction product of the polyisocyanate, the polyether polyol and the modifying agent and which is present in an amount sufficient to cap the reaction product of the polyisocyanate, the polyether polyol and the modifying agent.
Claim 24
Independent Claim
258 words
A method of increasing the viscosity and improving the leveling characteristics of an aqueous composition comprising mixing the aqueous composition with from 0.005 to about 10.000% by weight of a water dispersible, modified polyurethane which is the product of a reaction conducted under substantially anhydrous conditions of (a) polyisocyanate; (b) polyether polyol is an amount ranging from about 0.10 to about 10.00 moles per mole of polyisocyanate; (c) modifying agent in an amount ranging from about 0.015 to about 3.400 moles per mole of polyisocyanate, said modifying agent having the formula X.sub.x --R--Y.sub.y wherein R represents a group containing from 0 to 10 carbon atoms, X is a group containing at least one active hydrogen moiety selected from the group consisting of primary amino, secondary amino, carboxyl and mixtures thereof, Y is a group containing at least one active hydrogen moiety selected from the group consisting of primary amino, secondary amino, carboxyl, hydroxyl, mercapto and mixtures thereof, the sum of (x+y) is an integer greater than 1 and x is at least 1 wherein the modifying agent is composed of less than about 20 mole% of compounds wherein the sum of (x+y) is at least 3 and wherein the polyisocyanate, the polyester polyol and the modifying agent are used to form the polymer chain; and (d) capping agent which is reactive with the reaction product of the polyisocyanate, the polyether polyol and the modifying agent and which is present in an amount sufficient to cap the reaction product of the polyisocyanate, the polyether polyol and the modifying agent.
Claim 25
Independent Claim
258 words
A method of increasing the viscosity and improving the leveling characteristics of an aqueous composition comprising mixing the aqueous composition with from 0.005 to about 10.000% by weight of a water dispersible, modified polyurethane which is the product of a reaction conducted under substantially anhydrous conditions of (a) polyisocyanate; (b) polyether polyol is an amount ranging from about 0.10 to about 10.00 moles per mole of polyisocyanate; (c) modifying agent in an amount ranging from about 0.015 to about 3.400 moles per mole of polyisocyanate, said modifying agent having the formula X.sub.x --R--Y.sub.y wherein R represents a group containing from 0 to 10 carbon atoms, X is a group containing at least one active hydrogen moiety selected from the group consisting of primary amino, secondary amino, carboxyl and mixtures thereof, Y is a group containing at least one active hydrogen moiety selected from the group consisting of primary amino, secondary amino, carboxyl, hydroxyl, mercapto and mixtures thereof, the sum of (x+y) is an integer greater than 1 and x is at least 1 wherein the modifying agent is composed of less than about 20 mole% of compounds wherein the sum of (x+y) is at least 3 and wherein the polyisocyanate, the polyester polyol and the modifying agent are used to form the polymer chain; and (d) capping agent which is reactive with the reaction product of the polyisocyanate, the polyether polyol and the modifying agent and which is present in an amount sufficient to cap the reaction product of the polyisocyanate, the polyether polyol and the modifying agent.
Claim 26
Dependent Claim
24 words
The method of claim 21 wherein the water dispersible, modified polyurethane in the form of a dry powder is mixed with the aqueous composition.
Claim 27
Dependent Claim
30 words
The method of claim 21 wherein the water dispersible, modified polyurethane in the form of a slurry or solution in a water compatible solvent is mixed with the aqueous composition.
Claim 28
Dependent Claim
21 words
The method of claim 23 wherein the slurry or solution is the reaction mixture for preparing the water dispersible, modified polyurethane.
Claim 29
Dependent Claim
25 words
The method of claim 21 wherein the water dispersible, modified polyurethane in the form of a premixed aqueous gel is mixed with the aqueous composition.
Claim 30
Independent Claim
273 words
A method of preparing a water dispersible modified polyurethane comprising: (a) reacting at a temperature in the range of from about 20 to about 150° C. for from about 0.1 to about 48 hours under substantially anhydrous conditions (i) polyisocyanate, (ii) polyether polyol in an amount ranging from about 0.10 to about 10.00 moles per mole of polyisocyanate, and (iii) modifying agent in an amount ranging from about 0.015 to about 3.400 moles per mole of polyisocyanate, said modifying agent having the formula X.sub.x --R--Y.sub.y wherein R represents a group containing from 0 to 10 carbon atoms, X is a group containing at least one active hydrogen moiety selected from the group consisting of primary amino, secondary amino, carboxyl and mixtures thereof, Y is a group containing at least one active hydrogen moiety selected from the group consisting of primary amino, secondary amino, carboxyl, hydroxyl, mercapto and mixtures thereof, the sum of (x+y) is an integer greater than 1 and x is at least 1 wherein the modifying agent is composed of less than about 20 mole % of compounds wherein the sum of (x+y) is at least 3 and wherein the polyisocyanate, the polyether polyol and the modifying agent are used to form the polymer chain; (b) reacting with the reaction product of step a), at a temperature in the range of from about 20° to about 150° C. for from about 1 to about 48 hours and under substantially anhydrous conditions, capping agent in an amount sufficient to cap the reaction product of step (a) to thereby form the water dispersible modified polyurethane; and (c) recovering the water dispersible, modified polyurethane.
Claim 31
Independent Claim
273 words
A method of preparing a water dispersible modified polyurethane comprising: (a) reacting at a temperature in the range of from about 20 to about 150° C. for from about 0.1 to about 48 hours under substantially anhydrous conditions (i) polyisocyanate, (ii) polyether polyol in an amount ranging from about 0.10 to about 10.00 moles per mole of polyisocyanate, and (iii) modifying agent in an amount ranging from about 0.015 to about 3.400 moles per mole of polyisocyanate, said modifying agent having the formula X.sub.x --R--Y.sub.y wherein R represents a group containing from 0 to 10 carbon atoms, X is a group containing at least one active hydrogen moiety selected from the group consisting of primary amino, secondary amino, carboxyl and mixtures thereof, Y is a group containing at least one active hydrogen moiety selected from the group consisting of primary amino, secondary amino, carboxyl, hydroxyl, mercapto and mixtures thereof, the sum of (x+y) is an integer greater than 1 and x is at least 1 wherein the modifying agent is composed of less than about 20 mole % of compounds wherein the sum of (x+y) is at least 3 and wherein the polyisocyanate, the polyether polyol and the modifying agent are used to form the polymer chain; (b) reacting with the reaction product of step a), at a temperature in the range of from about 20° to about 150° C. for from about 1 to about 48 hours and under substantially anhydrous conditions, capping agent in an amount sufficient to cap the reaction product of step (a) to thereby form the water dispersible modified polyurethane; and (c) recovering the water dispersible, modified polyurethane.
Claim 32
Dependent Claim
15 words
The method of claim 26 wherein the polyether polyol is dried prior to the reaction.
Claim 33
Dependent Claim
25 words
The method of claim 26 wherein the polyether polyol is placed in a reaction vessel and the polyisocyanate and the modifying agent are added thereto.
Claim 34
Dependent Claim
22 words
The method of claim 26 wherein the reactions of steps (a) and (b) occur in the presence of a substantially anhydrous solvent.
Claim 35
Dependent Claim
41 words
The method of claim 29 wherein the water dispersible, modified polyurethane is recovered by evaporating any remaining solvent, cooling to at or below the glass transition temperature of the modified polyurethane and comminuting the modified polyurethane to obtain a fine powder.
References Cited (Backward Citations)
US3377308A
Cited
US3442843A
Cited
US3923926A
Cited
US4008196A
Cited
US3997491A
Cited
US4016121A
Cited
US4016120A
Cited
US4155892A
Cited
US4079028A
Cited
US4079028B1
Cited
US4180491A
Cited
US4314924A
Cited
US4293679A
Cited
US4298511A
Cited
US4327008A
Cited
US4373083A
Cited
US4408008A
Cited
US4426485A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-02-12 | 1988-08-13 | 1989-02-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-02-12 | 1992-08-13 | 1993-02-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-02-12 | 1996-08-13 | 1997-02-12 | $7700.00 | Window Closed / Lapsed |