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EP-4741435-A1 - POLYISOCYANATE COMPOSITION, TWO-COMPONENT CURABLE COMPOSITION, TWO-COMPONENT CURABLE COATING AGENT, TWO-COMPONENT CURABLE ADHESIVE, LAMINATE, AND PACKAGING MATERIAL

EP4741435A1EP 4741435 A1EP4741435 A1EP 4741435A1EP-4741435-A1

Abstract

To provide a novel polyisocyanate composition suitable for a two-component curable composition, such as a two-component curable adhesive or a two-component curable coating agent. The present invention provides a polyisocyanate composition (X) containing a polyisocyanate compound (A) having a plurality of isocyanate groups, in which the polyisocyanate compound (A) contains a polyurethane polyisocyanate (A1), which is a reaction product of a toluene diisocyanate (a) and a diol (b) having a molecular weight of 65 or more and 300 or less, and a two-component curable composition, coating agent, and adhesive containing the polyisocyanate composition (X) and an isocyanate reactive composition (Y).

Inventors

  • TESHIMA Tsuneyuki
  • ARAI MASAMITSU
  • TERAMURA Misato
  • CHIAPPA Christian
  • Demartini MARCO

Assignees

  • DIC Corporation

Dates

Publication Date
20260513
Application Date
20240627

Claims (15)

  1. A polyisocyanate composition (X) comprising: a polyisocyanate compound (A) having a plurality of isocyanate groups, wherein the polyisocyanate compound (A) contains a polyurethane polyisocyanate (A1), which is a reaction product of a toluene diisocyanate (a) and a diol (b) having a molecular weight of 65 or more and 300 or less.
  2. The polyisocyanate composition (X) according to claim 1, wherein the diol (b) contains a diol (b1) having an alkyl side chain having 1 or more and 4 or less carbon atoms.
  3. The polyisocyanate composition (X) according to claim 1, wherein the diol (b) contains a diol (b2) having an ether bond.
  4. The polyisocyanate composition (X) according to claim 1, wherein the polyurethane polyisocyanate (A1) has a content of 20 mass% or more in the polyisocyanate compound (A).
  5. The polyisocyanate composition (X) according to claim 1, wherein an isocyanate monomer has a content of 1.0 mass% or less in the polyisocyanate composition (X).
  6. A two-component curable composition comprising: the polyisocyanate composition (X) according to claim 1; and an isocyanate reactive composition (Y).
  7. A two-component curable coating agent comprising: the polyisocyanate composition (X) according to claim 1; and an isocyanate reactive composition (Y) containing an isocyanate reactive compound (E).
  8. The two-component curable coating agent according to claim 7, wherein the isocyanate reactive compound (E) contains at least one selected from a polyester polyol (E1), a polyether polyol (E2), a vegetable oil polyol (E3), a polyurethane polyol (E4), a sugar alcohol (E5), an acrylic polyol (E6), an amine compound (E7), and an epoxy compound (E8).
  9. The two-component curable coating agent according to claim 7, wherein the isocyanate reactive compound (E) contains at least one selected from a polyester polyol (E1-1) obtained by polycondensation of a polyhydric alcohol and a polycarboxylic acid containing an ortho-oriented polycarboxylic acid, a polyester polyol (E1-2) having an isocyanuric ring, and a polyester polyol (E1-3) having a polymerizable carbon-carbon double bond.
  10. A two-component curable adhesive comprising: the polyisocyanate composition (X) according to claim 1; and an isocyanate reactive composition (Y) containing an isocyanate reactive compound (E).
  11. The two-component curable adhesive according to claim 10, wherein the isocyanate reactive compound (E) contains at least one selected from a polyester polyol (E1), a polyether polyol (E2), a vegetable oil polyol (E3), a polyurethane polyol (E4), a sugar alcohol (E5), an acrylic polyol (E6), an amine compound (E7), and an epoxy compound (E8).
  12. The two-component curable adhesive according to claim 10, wherein the isocyanate reactive compound (E) contains at least one selected from a polyester polyol (E1-1) obtained by polycondensation of a polyhydric alcohol and a polycarboxylic acid containing an ortho-oriented polycarboxylic acid, a polyester polyol (E1-2) having an isocyanuric ring, and a polyester polyol (E1-3) having a polymerizable carbon-carbon double bond.
  13. A laminate comprising: a substrate; and a coating layer disposed on the substrate, wherein the coating layer is a cured coating film of the two-component curable coating agent according to claim 7.
  14. A laminate comprising: a first substrate; a second substrate; and an adhesive layer disposed between the first substrate and the second substrate, wherein the adhesive layer is a cured coating film of the two-component curable adhesive according to claim 10.
  15. A packaging material comprising: the laminate according to claim 13 or 14.

Description

TECHNICAL FIELD The present invention relates to a polyisocyanate composition, a two-component curable composition, a two-component curable coating agent, a two-component curable adhesive, a laminate, and a packaging material. BACKGROUND ART A polyurethane resin is generally produced by a reaction between a polyisocyanate and an active hydrogen group-containing compound, and is widely used in various industrial fields as coating agents, adhesives, pressure-sensitive adhesives, elastomers, hard foams, soft foams, binders, and the like. In addition, among products using such a urethane resin, a so-called two-component curable product in which a polyisocyanate and an active hydrogen compound are mixed and used immediately before use is known. As the polyisocyanate, a diisocyanate monomer such as hexamethylene diisocyanate, toluene diisocyanate, or diphenylmethane diisocyanate may be used, and an oligomer of a diisocyanate monomer or a urethane polyisocyanate derived from a diisocyanate and a polyol may also be used for the purpose of improving the physical properties of the polyurethane resin or reducing the vapor pressure to ensure the safety of the handling operator. CITATION LIST PATENT LITERATURE PTL 1: JP2014-159548APTL 2: JP2001-172602APTL 3: JP2017-210519A SUMMARY OF INVENTION TECHNICAL PROBLEM An object of the present invention is to provide a novel polyisocyanate composition suitable for a two-component curable composition, such as a two-component curable adhesive or a two-component curable coating agent. SOLUTION TO PROBLEM That is, the present invention relates to a polyisocyanate composition (X) containing a polyisocyanate compound (A) having a plurality of isocyanate groups, in which the polyisocyanate compound (A) contains a polyurethane polyisocyanate (A1), which is a reaction product of a toluene diisocyanate (a) and a diol (b) having a molecular weight of 65 or more and 300 or less. ADVANTAGEOUS EFFECTS OF INVENTION According to the present invention, it is possible to provide a novel polyisocyanate composition suitable for a two-component curable composition, such as a two-component curable adhesive or a two-component curable coating agent. DESCRIPTION OF EMBODIMENTS <Polyisocyanate Composition (X)> (Polyurethane Polyisocyanate (A1)) A polyisocyanate composition (X) according to the present invention contains a polyisocyanate compound (A) having a plurality of isocyanate groups, in which the polyisocyanate compound (A) contains a polyurethane polyisocyanate (A1), which is a reaction product of a toluene diisocyanate (a) and a diol (b) having a molecular weight of 65 or more and 300 or less. The toluene diisocyanate (a) may be any one or both of 2,4'-toluene diisocyanate and 2,6'-toluene diisocyanate. The diol (b) for use in the synthesis of the polyurethane polyisocyanate (A1) is not particularly limited as long as it has a molecular weight of 65 or more and 300 or less, and a known diol can be used. By using the diol (b) having a molecular weight of 65 or more, a polyisocyanate composition (X) having excellent storage stability can be obtained. By using a diol having a molecular weight of 300 or less, a reaction with the isocyanate reactive composition (Y) to be described later proceeds smoothly, and a two-component curable composition having fast expression of physical properties can be obtained. The diol (b) preferably contains at least one of a diol (b1) having an alkyl side chain having 1 or more and 4 or less carbon atoms and a diol (b2) having an ether bond. As the diol (b), a diol having both characteristics of the diol (b1) and the diol (b2) may be used. Examples of the diol (b1) having an alkyl side chain having 1 or more and 4 or less carbon atoms include 1,2-propanediol, neopentyl glycol, 2-butyl-2-ethyl-1,3-propanediol, 1,3-butanediol, 2-methyl-1,3-butanediol, 2-ethyl-1,3-butanediol, 2-propyl-1,3-butanediol, 2-butyl-1,3-butanediol, 2-pentyl-1,3-butanediol, 2-(1-methylethyl)-1,3-butanediol, 2,2-dimethyl-1,3-butanediol, 2,3-dimethyl-1,3-butanediol, 2-ethyl-2-methyl-1,3-butanediol, 3-methyl-1,3-butanediol, 1,2-pentanediol, 1,3-pentanediol, 2,4-pentanediol, 2-methyl-1,3-pentanediol, 2-ethyl-1,3-propanediol, 2-propyl-1,3-propanediol, 4-methyl-1,3-pentanediol, 2,4-dimethyl-1,3-pentanediol, 2,2,4-trimethyl-1,3-pentanediol, 2-methyl-2,4-pentanediol, 3-methyl-2,4-pentanediol, 3-ethyl-2,4-pentanediol, 1,2-hexanediol, 1,3-hexanediol, 2-methyl-1,3-hexanediol, 2-ethyl-1,3-hexanediol, 4-methyl-1,3-hexanediol, 5-methyl-1,3-hexanediol, 2,4-hexanediol, 1,3-heptanediol, 2-methyl-1,3-methyl-heptanediol, 4-methyl-1,3-heptanediol, 5-methyl-1,3-heptanediol, 6-methyl-1,3-heptanediol, 2,4-heptanediol, 2,4-octanediol, 3,5-octanediol, 2,4-nonanediol, 3,5-nonanediol, and 4,6-nonanediol. Examples of the diol (b2) having an ether bond include diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, dipropylene glycol, tripropylene glycol, tetrapropylene glycol, polypropylene glycol,