IP Library Granted Patent US 12,473,394
Granted Patent B2
US 12,473,394 · App. 17/964,526 · Granted Nov 18, 2025

Urethane compound

Inventors: Ikuo Yamamoto (Osaka, JP); Shinichi Minami (Shanghai, CN); Bin Zhou (Shanghai, CN)
Assignee: DAIKIN INDUSTRIES, LTD.
C08G18/285C08G18/283C08G18/48C08G18/8058C09D175/08D06M15/277D06M15/564D06M2101/06D06M2101/34D06M2200/11D06M2200/12
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Quick Facts
Patent No.
US 12,473,394
App. No.
17/964,526
Granted
Nov 18, 2025
Kind
B2
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.

Claims (42)

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.

Assignments (2)
CHANGE OF ADDRESS Recorded Jan 11, 2023
From: DAIKIN INDUSTRIES LTD.
To: DAIKIN INDUSTRIES LTD.
Reel/Frame 062355/0697 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 12, 2022
From: YAMAMOTO, IKUO; MINAMI, SHINICHI; ZHOU, BIN
To: DAIKIN INDUSTRIES, LTD.
Reel/Frame 061398/0722 →
Priority Claims (1)
CN 202010284458.X · Apr 13, 2020 · national
Continuity (2)
Continuation PCTJP2021015176 · Apr 12, 2021
Related Publication 20230050864A1 · Feb 16, 2023
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