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US4150946A Expired / Lapsed US ⏱️ 0.0 years remaining

Water-soluble polyurethanes and compositions and application thereof to substrates

Assignee: Rhone Poulenc Industries SA
•
Filing: 1977-11-08
•
Granted: 1979-04-24
•
Expires: 1997-11-08
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Abstract

Abstract Water-soluble polyurethanes are obtained by reacting sulfonated anionic polyesters containing about 0.8 to 2% sulfur with at least one diisocyanate to form film-forming polyurethanes which are directly soluble in water. The polyurethanes of the invention are advantageously applied in aqueous solution form as sizing for textiles and for bonding leathers.

Inventors

  • 👤 Jean Neel
  • 👤 Robert Violland

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 05:47
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/42; C08G18/46; C08G18/4676; C08G18/08; C08G18/0804; C08G18/0819; C08G18/0828; D; D06; D06M; D06M15/00; D06M15/19; D06M15/37; D06M15/564; Y; Y10; Y10S; Y10S528/00; Y10S528/904; Y10S528/905; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31551; Y10T428/31558

Claims Analysis

Total Claims: 59
Claim 1
Independent Claim 58 words
A film-forming, directly water-soluble, anionic polyester-polyurethane comprising recurring units of the formula --A--B--, wherein A is a sulfonated anionic polyester having a sulfur content of between about 0.8 and 2% by weight, an acid number of less than about 200 mg KOH/g, and a molecular weight of between about 500 and 3,000, and B is a diurethane unit.
Claim 2
Dependent Claim 58 words
A film-forming, directly water-soluble, anionic polyester-polyurethane comprising recurring units of the formula --A--B--, wherein A is a sulfonated anionic polyester having a sulfur content of between about 0.8 and 2% by weight, an acid number of less than about 200 mg KOH/g, and a molecular weight of between about 500 and 3,000, and B is a diurethane unit.
Claim 3
Dependent Claim 19 words
The polyester-polyurethane as defined by claim 1, having an average molecular weight of from about 10,000 to about 100,000.
Claim 4
Dependent Claim 32 words
A liquid composition for treating textile materials comprising water and dissolved therein a polyester-polyurethane as defined by claim 2, in an amount sufficient to impart abrasion resistance to the treated textile material.
Claim 5
Dependent Claim 30 words
A process for treating textile materials which comprises applying thereto a liquid composition as defined by claim 3, in an amount sufficient to impart abrasion resistance to said textile material.
Claim 6
Dependent Claim 25 words
The polyester-polyurethane as defined by claim 1, wherein the diisocyanate is selected from a group consisting of aliphatic, cycloaliphatic, unsaturated cycloaliphatic, aryl and alkylaryl diisocyanates.
Claim 7
Dependent Claim 24 words
The polyester-polyurethane as defined by claim 5, wherein the diisocyanate is selected from the group consisting of toluene diisocyanate, diphenylmethane diisocyanate and hexamethylene diisocyanate.
Claim 8
Dependent Claim 23 words
The polyester-polyurethane as defined by claim 1, wherein the sulfonated anionic polyester has an acid number of less than about 5 mg KOH/g.
Claim 9
Dependent Claim 24 words
The polyester-polyurethane as defined by claim 1, wherein the sulfonated anionic polyester has a sulfur content of between about 1.2 and 1.8% by weight.
Claim 10
Dependent Claim 17 words
A shaped article comprising the polyester-polyurethane as defined by claim 1, in powder, granule or flake form.
Claim 11
Dependent Claim 76 words
A method for the preparation of the polyester-polyurethane as defined by claim 1, comprising reacting at least one diisocyanate with a sulfonated anionic polyester having a sulfur content of between about 0.8 and 2% by weight, an acid number of less than about 20 mg KOH/g, and a molecular weight of between about 500 and 3,000, the molar ratio of isocyanate groups to total hydroxyl and carboxyl groups in said reactants being less than about 1.
Claim 12
Dependent Claim 25 words
The method as defined by claim 10, wherein the diisocyanate is selected from a group consisting of aliphatic, cycloaliphatic, unsaturated cycloaliphatic, aryl and alkylaryl diisocyanates.
Claim 13
Dependent Claim 24 words
The method as defined by claim 11, wherein the diisocyanate is selected from the group consisting of toluene diisocyanate, diphenylmethane diisocyanate and hexamethylene diisocyanate.
Claim 14
Dependent Claim 23 words
The method as defined by claim 10, wherein the sulfonated anionic polyester has an acid number of less than about 5 mg KOH/g.
Claim 15
Dependent Claim 24 words
The method as defined by claim 10, wherein the sulfonated anionic polyester has a sulfur content of between about 1.3 and 1.8% by weight.
Claim 16
Dependent Claim 21 words
The method as defined by claim 10, wherein the resultant polyester-polyurethane has an Mn value of between about 10,000 and 100,000.
Claim 17
Dependent Claim 15 words
The method as defined by claim 10, wherein the reaction is conducted in molten medium.
Claim 18
Dependent Claim 78 words
The polyester-polyurethane as defined by claim 1, which is a polycondensation product resulting from the reaction of at least one diisocyanate with a sulfonated anionic polyester having a sulfur content of between about 0.8 and 2% by weight, an acid number of less than about 20 mg KOH/g, and a molecular weight of between about 500 and 3,000, the molar ratio of isocyanate groups to total hydroxyl and carboxyl groups in said reactants being less than about 1.
Claim 19
Dependent Claim 32 words
A liquid composition for treating textile materials comprising water and dissolved therein a polyester-polyurethane as defined by claim 17, in an amount sufficient to impart abrasion resistance to the treated textile material.
Claim 20
Dependent Claim 30 words
A process for treating textile materials which comprises applying thereto a liquid composition as defined by claim 18, in an amount sufficient to impart abrasion resistance to said textile material.
Claim 21
Dependent Claim 32 words
A liquid composition for treating textile materials comprising water and dissolved therein a polyester-polyurethane as defined by claim 1, in an amount sufficient to impart abrasion resistance to the treated textile material.
Claim 22
Dependent Claim 20 words
A shaped article comprising a textile fiber bearing a water-washable sizing of the aqueous solution as defined by claim 20.
Claim 23
Dependent Claim 28 words
A shaped article comprising a flesh and grain split leather substrate, said flesh and grain splits having been bonded with the aqueous solution as defined by claim 20.
Claim 24
Dependent Claim 20 words
A liquid composition as defined by claim 20, wherein the amount of polyester-polyurethane is from about 1% to about 40%.
Claim 25
Dependent Claim 30 words
A process for treating textile materials which comprises applying thereto a liquid composition as defined by claim 23, in an amount sufficient to impart abrasion resistance to said textile material.
Claim 26
Dependent Claim 30 words
A process for treating textile materials which comprises applying thereto a liquid composition as defined by claim 20, in an amount sufficient to impart abrasion resistance to said textile material.
Claim 27
Dependent Claim 32 words
The process as defined by claim 25, which comprises applying the liquid composition to textile yarns in an amount sufficient to impart thereto an abrasion resistance sufficient to render the yarn weavable.
Claim 28
Dependent Claim 20 words
The process as defined by claim 26, wherein the textile yarn is a polyester yarn or a texturized polyester yarn.
Claim 29
Dependent Claim 39 words
The process as defined by claim 25, wherein the amount of the liquid composition applied to the textile material is equivalent to 1 to 3% by weight of the polyester-polyurethane relative to the dry weight of the textile material.
Claim 30
Dependent Claim 16 words
The process as defined by claim 25, wherein the textile material is a manmade textile material.
Claim 31
Dependent Claim 20 words
The process as defined by claim 25, wherein the textile material is a polyester material or a texturized polyester material.
Claim 32
Dependent Claim 32 words
An article of manufacture which comprises a textile material having deposited thereon an amount of a polyester-polyurethane as defined by claim 1, which is sufficient to impart abrasion resistance to said material.
Claim 33
Dependent Claim 14 words
The article of manufacture as defined by claim 31, which is a textile yarn.
Claim 34
Dependent Claim 19 words
The article of manufacture as defined by claim 32, which is a polyester yarn or a texturized polyester yarn.
Claim 35
Dependent Claim 28 words
The article of manufacture as defined by claim 31, wherein the amount of the polyester-polyurethane is from about 1 to about 3% by weight of the dry material.
Claim 36
Dependent Claim 83 words
A film-forming, directly water-soluble, anionic polyester-polyurethane comprising recurring units of the formula --A--B--, wherein A is a sulfonated anionic polyester having a sulfur content of between about 0.8 and 2% by weight, an acid number of less than about 200 mg KOH/g, and a molecular weight of between about 500 and 3,000, and B is a diurethane unit, wherein the sulfonated anionic polyester is the co-condensation product of an organic diacid, an organic sulfonated diacid and a diol, or the ester-forming derivatives thereof.
Claim 37
Dependent Claim 83 words
A film-forming, directly water-soluble, anionic polyester-polyurethane comprising recurring units of the formula --A--B--, wherein A is a sulfonated anionic polyester having a sulfur content of between about 0.8 and 2% by weight, an acid number of less than about 200 mg KOH/g, and a molecular weight of between about 500 and 3,000, and B is a diurethane unit, wherein the sulfonated anionic polyester is the co-condensation product of an organic diacid, an organic sulfonated diacid and a diol, or the ester-forming derivatives thereof.
Claim 38
Dependent Claim 35 words
The polyester-polyurethane as defined by claim 35, wherein the organic diacid is selected from the group consisting of saturated or unsaturated aliphatic diacids, aromatic diacids, polynuclear aromatic diacids, araliphatic diacids, and the ester-forming derivatives thereof.
Claim 39
Dependent Claim 30 words
The polyester-polyurethane as defined by claim 36, wherein the organic diacid is selected from the group consisting of succinic, adipic, suberic, sebaric, maleic, fumaric, itaconic, orthophthalic, isophthalic and terephthalic acid.
Claim 40
Dependent Claim 24 words
The polyester-polyurethane as defined by claim 37, wherein the organic diacid is selected from the group consisting of adipic, orthophthalic, isophthalic and terephthalic acid.
Claim 41
Dependent Claim 21 words
The polyester-polyurethane as defined by claim 35, wherein the diol is selected from the group consisting of aliphatic and cycloaliphatic glycols.
Claim 42
Dependent Claim 24 words
The polyester-polyurethane as defined by claim 39, wherein the diol is selected from the group consisting of ethylene glycol, diethylene glycol and neopentyl glycol.
Claim 43
Dependent Claim 28 words
The polyester-polyurethane as defined by claim 35, wherein the organic sulfonated diacid is selected from the group consisting of sulfoisophthalic and sulfosuccinic acid, and the ester-forming derivatives thereof.
Claim 44
Dependent Claim 26 words
The polyester-polyurethane as defined by claim 41, wherein the organic sulfonated compound is selected from the group consisting of 5-sulfo-isophthalic acid, sodium dimethylisophthalate-5-sulfonate and sodium dimethylsulfosuccinate.
Claim 45
Dependent Claim 131 words
A film-forming, directly water-soluble, anionic polyester-polyurethane comprising recurring units of the formula --A--B--, wherein A is a sulfonated anionic polyester having a sulfur content of between about 0.8 and 2% by weight, an acid number of less than 200 mg KOH/g, and a molecular weight of between about 500 and 3,000, and B is a diurethane unit, wherein the polyester chain A comprises at least one unit of the formula I and at least one unit of the formula II ##STR5## wherein R 1 is a divalent saturated hydrocarbon group, a divalent unsaturated aliphatic hydrocarbon group or a divalent monocyclic aromatic group, R 2 is a divalent saturated aliphatic group or a divalent saturated cyclic hydrocarbon group, and R 3 is a ##STR6## group wherein M is an alkali metal ion.
Claim 46
Dependent Claim 131 words
A film-forming, directly water-soluble, anionic polyester-polyurethane comprising recurring units of the formula --A--B--, wherein A is a sulfonated anionic polyester having a sulfur content of between about 0.8 and 2% by weight, an acid number of less than 200 mg KOH/g, and a molecular weight of between about 500 and 3,000, and B is a diurethane unit, wherein the polyester chain A comprises at least one unit of the formula I and at least one unit of the formula II ##STR5## wherein R 1 is a divalent saturated hydrocarbon group, a divalent unsaturated aliphatic hydrocarbon group or a divalent monocyclic aromatic group, R 2 is a divalent saturated aliphatic group or a divalent saturated cyclic hydrocarbon group, and R 3 is a ##STR6## group wherein M is an alkali metal ion.
Claim 47
Dependent Claim 53 words
The polyester-polyurethane as defined by claim 43, wherein the polyester units A are linked together by diurethane unit B having the formula ##STR7## wherein R 2 is as defined above, and R 4 is a divalent group selected from the group consisting of hexamethylene, tetramethylene ##STR8## m-phenylene, p-phenylene, 2,4-tolylene, 2,6-tolylene, 4,4'-diyl-dicyclohexylmethane, 4,4'-diphenylmethane, 1,5-diyl-naphthalene.
Claim 48
Dependent Claim 32 words
A liquid composition for treating textile materials comprising water and dissolved therein a polyester-polyurethane as defined by claim 44, in an amount sufficient to impart abrasion resistance to the treated textile material.
Claim 49
Dependent Claim 52 words
The polyester-polyurethane as defined by claim 43, wherein R 1 is a divalent group selected from the group consisting of ethylene, tetramethylene, hexamethylene, octamethylene, vinylene, 2,3-propenylene, o-phenylene, m-phenylene, and p-phenylene, and R 2 is a divalent group selected from the group consisting of ethylene, tetramethylene, hexamethylene, 2,2-dimethylpropylene, 3,-oxopentamylene, 4-oxoheptanylene, 1,3-cyclohexylene and 4,4'-diyl-2,2-dicyclohexylpropane.
Claim 50
Dependent Claim 32 words
A liquid composition for treating textile materials comprising water and dissolved therein a polyester-polyurethane as defined by claim 43, in an amount sufficient to impart abrasion resistance to the treated textile material.
Claim 51
Independent Claim 100 words
A method for the preparation of a film-forming, directly water-soluble, anionic polyester-polyurethane comprising reacting at least one diisocyanate with a sulfonated anionic polyester having a sulfur content of between about 0.8 and 2% by weight, an acid number of less than about 20 mg KOH/g, and a molecular weight of between about 500 and 3,000, the molar ratio of isocyanate groups to total hydroxyl acid carboxyl groups in said reactants being less than about, 1 wherein the sulfonated anionic polyester is the co-condensation product of an organic diacid, an organic sulfonated diacid and a diol, or the ester-forming derivatives thereof.
Claim 52
Independent Claim 100 words
A method for the preparation of a film-forming, directly water-soluble, anionic polyester-polyurethane comprising reacting at least one diisocyanate with a sulfonated anionic polyester having a sulfur content of between about 0.8 and 2% by weight, an acid number of less than about 20 mg KOH/g, and a molecular weight of between about 500 and 3,000, the molar ratio of isocyanate groups to total hydroxyl acid carboxyl groups in said reactants being less than about, 1 wherein the sulfonated anionic polyester is the co-condensation product of an organic diacid, an organic sulfonated diacid and a diol, or the ester-forming derivatives thereof.
Claim 53
Dependent Claim 35 words
The method as defined by claim 48, wherein the organic diacid is selected from the group consisting of saturated or unsaturated aliphatic diacids, aromatic diacids, polynuclear aromatic diacids, araliphatic diacids, and the ester-forming derivatives thereof.
Claim 54
Dependent Claim 30 words
The method as defined by claim 49, wherein the organic diacid is selected from the group consisting of succinic, adipic, suberic, sebaric, maleic, fumaric, itaconic, orthophthalic isophthalic and terephthalic acid.
Claim 55
Dependent Claim 24 words
The method as defined by claim 50, wherein the organic diacid is selected from the group consisting of adipic, orthophthalic, isophthalic and terephthalic acid.
Claim 56
Dependent Claim 21 words
The method as defined by claim 48, wherein the diol is selected from the group consisting of aliphatic and cycloaliphatic glycols.
Claim 57
Dependent Claim 24 words
The method as defined by claim 52, wherein the diol is selected from the group consisting of ethylene glycol, diethylene glycol and neopentyl glycol.
Claim 58
Dependent Claim 28 words
The method as defined by claim 48, wherein the organic sulfonated diacid is selected from the group consisting of sulfoisophthalic and sulfosuccinic acid, and the ester-forming derivatives thereof.
Claim 59
Dependent Claim 26 words
The method as defined by claim 54, wherein the organic sulfonated compound is selected from the group consisting of 5-sulfo-isophthalic acid, sodium dimethylisophthalate-5-sulfonate and sodium dimethylsulfosuccinate.

References Cited (Backward Citations)

US3018272A Cited
US3189578A Cited
GB1128568A Cited
UST862017I4 Cited
US3998871A Cited
US3920598A Cited
US4110284A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1982-04-23 1982-10-23 1983-04-24 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-04-23 1986-10-23 1987-04-24 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-04-23 1990-10-23 1991-04-24 $7700.00 Window Closed / Lapsed

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