Urethane compound

Patent metadata

Field	Value
Publication number	US-12473394-B2
Application number	US-202217964526-A
Country	US
Kind code	B2
Filing date	Oct 12, 2022
Priority date	Apr 13, 2020
Publication date	Nov 18, 2025
Grant date	Nov 18, 2025

Abstract

A urethane compound (A) including units formed from (A1) an isocyanate and (A2) a long-chain alcohol represented by the formula HO—Z(Y—R) n [wherein the R moieties are each independently —O—, —NH—, —O—C(═O)—, —NH—C(═O)—, —C(═O)—NH—, —O—C(═O)—NH—, —NH—C(═O)—O—, —NH—C(═O)—NH—, —NH—S(═O) 2 —, —S(═O) 2 —NH—, —NH—(CH 2 ) m —NH—S(═O) 2 —, —NH—(CH 2 ) m —S(═O) 2 —NH—, etc. (m is an integer of 1-5), Z is a direct bond or a di- or trivalent hydrocarbon group having 1-5 carbon atoms, and n is 1 or 2]. Also disclosed is a urethane mixture containing the urethane compound (A), and at least one selected from the polyisocyanate (A1), the long-chain alcohol (A2), a blocking agent (A3) and an alcohol compound (A4); an aqueous urethane composition; a method for producing the aqueous urethane composition; a method of treating a substrate; and a treated textile product.

First claim

What is claimed is:

1 . An aqueous urethane composition comprising:
(A) a urethane compound, and (B) water;
wherein
the urethane compound (A) comprises units formed from:
(A1) an isocyanate, and
(A2) a long-chain alcohol represented by the formula:
HO—Z(Y—R) n

wherein
R is each independently a hydrocarbon group having 7 to 40 carbon atoms,
Y is each independently —O—, —NH—, —NH—C(═O)—, —C(═O)—NH—, —NH—C(═O)—O—, —NH—C(═O)—NH—, —C 6 H 4 —, —NH—(CH 2 ) m —NH—, —NH—(CH 2 ) m —O—, —O—C(═O)—, —C(═O)—O—, —NH—(CH 2 ) m —O—C(═O)—, —NH—(CH 2 ) m —C(═O)—O—, —O—C(═O)—NH—, —O—C 6 H 4 —, —NH—S(═O) 2 —, —S(═O) 2 —NH—, —NH—(CH 2 ) m —O—C(═O)—NH—, —NH—(CH 2 ) m —NH—C(═O)—O—, —NH—(CH 2 ) m —C(═O)—NH—, —NH—(CH 2 ) m —NH—C(═O)—, —NH—(CH 2 ) m —NH—C(═O)—NH—, —NH—(CH 2 ) m —O—C 6 H 4 —, —NH—(CH 2 ) m —NH—C 6 H 4 —, —NH—(CH 2 ) m —NH—S(═O) 2 —, or —NH—(CH 2 ) m —S(═O) 2 —NH—, wherein m is an integer of 1 to 5,
Z is a direct bond or a divalent hydrocarbon group having 1 to 5 carbon atoms, and
n is 1.

2 . The aqueous urethane composition according to claim 1 , further comprising a unit formed from at least one selected from:
(A3) a blocking agent, and (A4) an alcohol compound.

3 . The aqueous urethane composition according to claim 1 , wherein the isocyanate (A1) is at least one selected from tolylene diisocyanate (TDI), diphenylmethane diisocyanate (MDI), an MDI oligomer, naphthalene-1,5-diisocyanate, xylylene diisocyanate, hexamethylene diisocyanate (HDI), 4,4-dicyclohexylmethane diisocyanate, norbornane diisocyanate, isophorone diisocyanate (IPDI), an adduct of diisocyanate, an allophanate-modified product, a biuret-modified product, an isocyanurate-modified product or a carbodiimide-modified product, and a urethane prepolymer.

4 . The aqueous urethane composition according to claim 1 , wherein the long-chain alcohol (A2) is at least one selected from:
HO—(CH 2 ) m —NH—C(═O)—R, HO—(CH 2 ) m —C(═O)—NH—R, HO—(CH 2 ) m —O—C(═O)—R, HO—(CH 2 ) m —C(═O)—O—R, HO—(CH 2 ) m —NH—C(═O)—O—R, HO—(CH 2 ) m —O—C(═O)—NH—R, HO—(CH 2 ) m —NH—C(═O)—NH—R, HO—(CH 2 ) m —NH—S(═O) 2 —R, and HO—(CH 2 ) m —S(═O) 2 —NH—R,
wherein R is a hydrocarbon group having 12 to 30 carbon atoms, and m is an integer of 1 to 5.

5 . The aqueous urethane composition according to claim 2 , wherein the blocking agent (A3) is at least one selected from oxime, phenol, alcohol, mercaptan, amide, imide, imidazole, urea, amine, imine, pyrazole, and an active methylene compound.

6 . The aqueous urethane composition according to claim 2 , wherein
the alcohol compound (A4) is a monool or a polyol, the monool is a compound obtained by adding a C 2 or C 3 alkylene oxide to a starting monoalcohol having 1 to 10 carbon atoms, and the polyol is a diol or a polyol having 3 or more hydroxyl groups, and is at least one selected from a low molecular weight polyol, a polyether polyol, a polyester polyol, a polyester polycarbonate polyol, and a crystalline or non-crystalline polycarbonate polyol.

7 . The aqueous urethane composition according to claim 1 , wherein the aqueous urethane composition is a urethane mixture comprising the urethane compound (A), and at least one selected from the group consisting of the polyisocyanate (A1), the long-chain alcohol (A2), the blocking agent (A3), and the alcohol compound (A4).

8 . The aqueous urethane composition according to claim 1 , wherein the aqueous urethane composition is an aqueous dispersion.

9 . The aqueous urethane composition according to claim 1 , wherein the aqueous urethane composition is a cross-linking agent or an adjuvant.

10 . A method for producing the aqueous urethane composition according to claim 1 , the method comprising:
mixing the isocyanate (A1) and the long-chain alcohol (A2) in an organic solvent to react the isocyanate (A1) and the long-chain alcohol (A2), and subsequently mixing the reaction product with water.

11 . A method for treating a substrate, the method comprising:
treating a substrate the aqueous urethane composition according to claim 1 .

12 . A treated textile product, comprising the urethane compound in the aqueous urethane composition according to claim 1 attached as a crosslinked product to a treatment substrate.

Assignees

• Daikin Ind Ltd

Inventors

• Yamamoto Ikuo
• Minami Shinichi
• Zhou Bin

Classifications

• D06M2200/12

  Hydrophobic properties · CPC title

• D06M2200/11

  Oleophobic properties · CPC title

• D06M2101/34

  Polyamides · CPC title

• D06M2101/06

  cellulosic · CPC title

• D06M15/564

  Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them · CPC title