# US 12,760,141 B2 · Aqueous resin crosslinking agent, aqueous resin crosslinking agent-containing liquid, and aqueous resin composition

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- Number: US 12,760,141 B2
- Document ID: US12760141B2
- Status: Granted
- Kind: B2
- Application number: 18/022,281
- Filed: 2021-08-20
- Published: 2023-10-12
- Granted: 2026-10-13
- Earliest claimed: 2020-08-25
- Assignees: Nisshinbo Chemical Inc.
- Applicants: Nisshinbo Chemical Inc.
- Inventors: Nami Tsukamoto; Naoki Nishikawa
- Web page: https://patentgrep.com/patent/US12760141B2

## CPC

- C08G 18/025: {the polymeric products containing carbodiimide groups}
- C08G 18/79: characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08L 79/00: Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

Provided is a waterborne resin crosslinking agent, as well as a waterborne resin crosslinking agent-containing liquid and a waterborne resin composition, including the waterborne resin crosslinking agent. The waterborne resin crosslinking agent of the present invention includes a polycarbodiimide compound (A) and a polycarbodiimide compound (B); the polycarbodiimide compound (A) has a structure in which the isocyanate groups at both terminals are each capped with a predetermined hydrophilic organic compound; the polycarbodiimide compound (B) has, as a structural unit, a diisocyanate compound having one cyclohexyl ring or one benzene ring, and has a structure in which the isocyanate groups at both terminals are each capped with a predetermined organic compound, and the polycarbodiimide compound (A) is in an amount of 5 to 90 parts by mass per 100 parts by mass in total of the polycarbodiimide compounds (A) and (B).

## Claims

### Claim 1

A waterborne resin crosslinking agent, comprising a polycarbodiimide compound (A) and a polycarbodiimide compound (B), wherein
the polycarbodiimide compound (A) has a structure in which isocyanate groups at both terminals are each capped with a hydrophilic organic compound, and at least one of the hydrophilic organic compounds has a molecular weight of 340 or more,
the polycarbodiimide compound (B) has, as a structural unit, a diisocyanate compound having one cyclohexyl ring or one benzene ring, and has a structure in which isocyanate groups at both terminals are each capped with an organic compound having a molecular weight of 300 or less,
the polycarbodiimide compound (A) is in an amount of 5 to 90 parts by mass per 100 parts by mass in total of the polycarbodiimide compound (A) and the polycarbodiimide compound (B),
the polycarbodiimide compound (A) is a product of a decarboxylation condensation reaction of a diisocyanate compound, and
wherein the degree of polymerization of carbodiimide groups in the polycarbodiimide compound (A) is 5 to 7.

### Claim 2 (depends on 1)

The waterborne resin crosslinking agent according to claim 1, wherein the hydrophilic organic compound having a molecular weight of 340 or more is a compound represented by the following formula (1):
R1(OCHR2CH2)nOH (1)
wherein R1 is an alkyl group, cycloalkyl group, or aryl group having 1 to 20 carbon atoms, R2 is a hydrogen atom or a methyl group, and n is a numeral of 7 to 30.

### Claim 3 (depends on 2)

The waterborne resin crosslinking agent according to claim 2, wherein, in the formula (1), R1 is a methyl group and R2 is a hydrogen atom.

### Claim 4 (depends on 1)

The waterborne resin crosslinking agent according to claim 1, wherein the organic compound having a molecular weight of 300 or less is a compound having one functional group that reacts with an isocyanate group.

### Claim 5 (depends on 1)

The waterborne resin crosslinking agent according to claim 1, wherein the organic compound having a molecular weight of 300 or less is a compound selected from the group consisting of a primary or secondary monoamine, a monoisocyanate, a monool, a monoepoxide, and a monocarboxylic acid.

### Claim 6 (depends on 1)

The waterborne resin crosslinking agent according to claim 1, wherein the diisocyanate compound is a compound having a primary isocyanate group.

### Claim 7 (depends on 1)

A waterborne resin crosslinking agent-containing liquid, comprising the waterborne resin crosslinking agent according to claim 1, and an aqueous medium.

### Claim 8 (depends on 7)

The waterborne resin crosslinking agent-containing liquid according to claim 7, wherein the aqueous medium is water or a mixed solvent of water and a hydrophilic solvent.

### Claim 9 (depends on 7)

The waterborne resin crosslinking agent-containing liquid according to claim 7, further comprising a surfactant.

### Claim 10 (depends on 9)

The waterborne resin crosslinking agent-containing liquid according to claim 9, wherein the surfactant is an anionic surfactant.

### Claim 11 (depends on 10)

The waterborne resin crosslinking agent-containing liquid according to claim 10, wherein the anionic surfactant is one or more selected from the group consisting of an alkylbenzenesulfonate, an alkylsulfate, and sodium N-cocoyl methyl taurate.

### Claim 12 (depends on 1)

A waterborne resin composition, comprising the waterborne resin crosslinking agent according to claim 1 and a waterborne resin.

### Claim 13 (depends on 12)

The waterborne resin composition according to claim 12, wherein the waterborne resin has a functional group selected from the group consisting of a carboxy group, an amino group and a hydroxyl group.

### Claim 14 (depends on 12)

The waterborne resin composition according to claim 12, wherein the waterborne resin is one or more selected from the group consisting of a polyester resin, an acrylic resin, a polyurethane resin, an epoxy resin, a styrene-acrylic resin, a melamine resin, a polyolefin resin, and a fluororesin.

### Claim 15 (depends on 12)

The waterborne resin composition according to claim 12, wherein the waterborne resin composition is used for an adhesive, a fiber treatment agent, a coating agent, an ink, a paint, or a pressure-sensitive adhesive.

### Claim 16 (depends on 12)

The waterborne resin composition according to claim 12, wherein the waterborne resin composition is for wet-on-wet coating.

### Claim 17 (depends on 12)

A cured film formed of the waterborne resin composition according to claim 12.

### Claim 18 (depends on 17)

An article comprising the cured film according to claim 17 formed on a base material.
