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EP-4741437-A1 - POLYURETHANE RESIN COMPOSITION

EP4741437A1EP 4741437 A1EP4741437 A1EP 4741437A1EP-4741437-A1

Abstract

Provided is a polyurethane resin composition containing a polyurethane resin (U) and an organic solvent (S), in which the polyurethane resin (U) contains a structural unit derived from a polyoxyethylene diol (A), a structural unit derived from a polycarbonate diol (B), a structural unit derived from an aliphatic isocyanate compound (C), a structural unit derived from a diol (D) having 2 to 6 carbon atoms, and a structural unit derived from a diamine (E) having 2 to 20 carbon atoms, and the structural unit derived from the aliphatic isocyanate compound (C) is a structural unit derived from an acyclic aliphatic diisocyanate (c1) in which two isocyanate groups are directly bonded to an acyclic hydrocarbon having an odd number of carbon atoms, or a structural unit derived from an alicyclic diisocyanate (c2) in which the number of isocyanate groups directly bonded to an alicyclic hydrocarbon is 0 or 1.

Inventors

  • SHIRAI, Kazuaki
  • OHARA, TERUHIKO
  • MORI, ATSUSHI

Assignees

  • Mitsubishi Chemical Corporation

Dates

Publication Date
20260513
Application Date
20240704

Claims (19)

  1. A polyurethane resin composition, comprising: a polyurethane resin (U); and an organic solvent (S), wherein the polyurethane resin (U) comprises a structural unit derived from a polyoxyethylene diol (A), a structural unit derived from a polycarbonate diol (B), a structural unit derived from an aliphatic isocyanate compound (C), a structural unit derived from a diol (D) having 2 to 6 carbon atoms, and a structural unit derived from a diamine (E) having 2 to 20 carbon atoms, and the structural unit derived from the aliphatic isocyanate compound (C) comprises a structural unit derived from an acyclic aliphatic diisocyanate (c1) in which two isocyanate groups are directly bonded to an acyclic hydrocarbon having an odd number of carbon atoms, or a structural unit derived from an alicyclic diisocyanate (c2) in which the number of isocyanate groups directly bonded to an alicyclic hydrocarbon is 0 or 1.
  2. The polyurethane resin composition according to claim 1, wherein, in the polyurethane resin (U), a weight ratio (A)/((A) + (B)) of the structural unit derived from the polyoxyethylene diol (A) relative to a total weight of the structural unit derived from the polyoxyethylene diol (A) and the structural unit derived from the polycarbonate diol (B) is from 0.50 to 0.90.
  3. The polyurethane resin composition according to claim 1, wherein a molar ratio of isocyanate group-derived nitrogen atoms in the structural unit derived from the aliphatic isocyanate compound (C), relative to a number of moles of amino group-derived nitrogen atoms in the diamine (E), is from 1.5 to 2.5.
  4. The polyurethane resin composition according to claim 1, wherein the structural unit derived from the polyoxyethylene diol (A) comprises a structural unit derived from a polyoxyethylene diol having a hydroxyl value of from 26.0 to 140.0 mgKOH/g.
  5. The polyurethane resin composition according to claim 1, wherein the structural unit derived from the polycarbonate diol (B) comprises a structural unit derived from a polycarbonate diol having a hydroxyl value of from 32.0 to 124.7 mgKOH/g.
  6. The polyurethane resin composition according to claim 1, wherein the structural unit derived from the polycarbonate diol (B) comprises a structural unit represented by the following Formula (b1) and a structural unit represented by the following Formula (b2), or the structural unit represented by the following Formula (b2), and when both the structural units of Formula (b1) and Formula (b2) are present, a molar ratio (b1)/(b2) is from 95/5 to 5/95: -O-R 1 -O- (b1) -O-R 2 -O- (b2) in Formula (b1), R 1 represents a divalent alkylene group having 3 to 5 carbon atoms which may have a substituent; and, in Formula (b2), R 2 represents a divalent alkylene group having 6 to 20 carbon atoms which may have a substituent.
  7. The polyurethane resin composition according to claim 1, wherein a content of the structural unit derived from the aliphatic isocyanate compound (C) in the polyurethane resin (U) is 50% by weight or less.
  8. The polyurethane resin composition according to claim 1, wherein the diamine (E) comprises a diamine having 6 to 12 carbon atoms.
  9. The polyurethane resin composition according to claim 1, wherein, in the polyurethane resin (U), a molar ratio of hydroxy group-derived oxygen atoms of the polyoxyethylene diol (A) and hydroxy group-derived oxygen atoms of the polycarbonate diol (B) relative to a number of moles of hydroxy group-derived oxygen atoms of the diol (D) is from 0.5 to 1.5.
  10. The polyurethane resin composition according to claim 1, wherein, in the polyurethane resin (U), a molar ratio of isocyanate group-derived nitrogen atoms of the aliphatic isocyanate compound (C) relative to a total number of moles of hydroxy group-derived oxygen atoms of the polyoxyethylene diol (A), hydroxy group-derived oxygen atoms of the polycarbonate diol (B), and hydroxy group-derived oxygen atoms of the diol (D) is from 1.5 to 4.0.
  11. The polyurethane resin composition according to claim 1, wherein a content of a polar solvent (Y) satisfying the following conditions (y1) and (y2) in the organic solvent (S) is 5% by weight or less: (y1) Not classified into the carcinogenicity category according to the GHS (9th revised edition) classification; and (y2) The acute toxicity is classified into Categories 1 to 3 according to the GHS (9th revised edition) classification, or the reproductive toxicity is classified into Category 1A or 1B according to the GHS (9th revised edition) classification.
  12. The polyurethane resin composition according to claim 1, wherein the organic solvent (S) comprises a monohydric alcohol having 5 or fewer carbon atoms, and at least one selected from the group consisting of a ketone having 6 or fewer carbon atoms and an ester having 8 or fewer carbon atoms.
  13. The polyurethane resin composition according to claim 1, wherein a content of the polyurethane resin (U) is from 5 to 50% by weight.
  14. The polyurethane resin composition according to claim 1, further comprising a biomass-derived compound.
  15. A moisture-permeable waterproof fabric comprising the polyurethane resin composition according to any one of claims 1 to 14.
  16. A sportswear comprising the polyurethane resin composition according to any one of claims 1 to 14.
  17. A rainwear comprising the polyurethane resin composition according to any one of claims 1 to 14.
  18. A ten comprising the polyurethane resin composition according to any one of claims 1 to 14.
  19. A hygiene product comprising the polyurethane resin composition according to any one of claims 1 to 14.

Description

TECHNICAL FIELD The present disclosure relates to: a polyurethane resin composition; and a moisture-permeable waterproof fabric, a sportswear, a rainwear, a tent, and a hygiene product, in which the polyurethane resin composition is used. BACKGROUND ART Polyurethane resins have excellent elasticity and durability (wear resistance and heat resistance) and are thus used in a variety of materials and, in recent years, because of their excellent properties, they are expected to be developed as moisture-permeable waterproof materials in particular. The moisture-permeable waterproof materials are used in outdoor products, sportswear, sports shoes, rainwear (e.g., raincoats), tents, disposable diapers, wound dressings (bandages), and the like, and the polyurethane resins used for these applications are strongly desired to have a good balance of physical properties, such as durability, in addition to moisture-permeable waterproof performance. As a polyurethane resin for a moisture-permeable waterproof material, Patent Document 1 proposes a polyurethane resin formed from a polyurethane resin composition for a moisture-permeable waterproof fabric, which composition is composed of an alcohol solution of a hydrophilic polyurethane resin having an oxyethylene group content of 10 to 80% by weight in the resin, and a polyisocyanate. Further, Patent Document 2 proposes an aqueous polyurethane resin that has a structural unit derived from an emulsifier having a polyoxyethylene group as a side chain. Moreover, Patent Document 3 proposes a polyurethane resin obtained by curing a composition that contains a monofunctional epoxy compound and a polyurethane obtained by reacting one or more polyols selected from polytetramethylene polyols, polycarbonate polyols, and polyolefin polyols, with a polyisocyanate, a carboxy group-containing polyol, and a chain extender. PRIOR ART DOCUMENTS PATENT DOCUMENTS Patent Document 1: JP 2007-211239 APatent Document 2: JP 2006-335951 APatent Document 3: WO 2021/187504 A1 SUMMARY OF INVENTION TECHNICAL PROBLEMS An object of the present disclosure is to provide a polyurethane resin composition that can give a moisture-permeable waterproof material excellent in moisture-permeable waterproof performance and durability. Another object of the present disclosure is to provide a moisture-permeable waterproof fabric, a sportswear, a rainwear, a tent, and a hygiene product, in which the polyurethane resin composition is used. SOLUTION TO PROBLEMS The present inventors intensively studied to solve the above-described problems and consequently discovered that a moisture-permeable waterproof material excellent in moisture-permeable waterproof performance and durability can be obtained from a polyurethane resin composition that contains a polyurethane resin having specific structure and composition and an organic solvent; and that the polyurethane resin composition is suitable for use in moisture-permeable waterproof fabrics, sportswear, rainwear, tents, hygiene products, and the like. That is, the present disclosure has the following characteristics. [1] A polyurethane resin composition, comprising: a polyurethane resin (U); andan organic solvent (S),whereinthe polyurethane resin (U) comprises a structural unit derived from a polyoxyethylene diol (A), a structural unit derived from a polycarbonate diol (B), a structural unit derived from an aliphatic isocyanate compound (C), a structural unit derived from a diol (D) having 2 to 6 carbon atoms, and a structural unit derived from a diamine (E) having 2 to 20 carbon atoms, andthe structural unit derived from the aliphatic isocyanate compound (C) comprises a structural unit derived from an acyclic aliphatic diisocyanate (c1) in which two isocyanate groups are directly bonded to an acyclic hydrocarbon having an odd number of carbon atoms, or a structural unit derived from an alicyclic diisocyanate (c2) in which the number of isocyanate groups directly bonded to an alicyclic hydrocarbon is 0 or 1.[2] The polyurethane resin composition according to [1], wherein, in the polyurethane resin (U), a weight ratio (A)/((A) + (B)) of the structural unit derived from the polyoxyethylene diol (A) relative to a total weight of the structural unit derived from the polyoxyethylene diol (A) and the structural unit derived from the polycarbonate diol (B) is from 0.50 to 0.90.[3] The polyurethane resin composition according to [1] or [2], wherein a molar ratio of isocyanate group-derived nitrogen atoms in the structural unit derived from the aliphatic isocyanate compound (C) relative to the number of moles of amino group-derived nitrogen atoms in the diamine (E) is from 1.5 to 2.5.[4] The polyurethane resin composition according to any one of [1] to [3], wherein the structural unit derived from the polyoxyethylene diol (A) is a structural unit derived from a polyoxyethylene diol having a hydroxyl value of from 26.0 to 140.0 mgKOH/g.[5] The polyurethane resin composition according