# US 11,078,321 B2 · Isocyanate composition, method for producing isocyanate composition, and method for producing isocyanate polymer

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 11,078,321 B2
- Document ID: US11078321B2
- Status: Granted
- Kind: B2
- Application number: 16/340,532
- Filed: 2017-10-13
- Published: 2020-02-13
- Granted: 2021-08-03
- Earliest claimed: 2016-10-14
- Assignees: Asahi Kasei Kabushiki Kaisha
- Applicants: Asahi Kasei Kabushiki Kaisha
- Inventors: Nobuhisa Miyake; Masaaki Shinohata; Atsushi Ohkubo; Koichi Nakaoka; Yuji Kosugi
- Web page: https://patentgrep.com/patent/US11078321B2

## CPC

- C08G 18/725: {Combination of polyisocyanates of C08G18/78 with other polyisocyanates}
- C07C 263/18: Separation; Purification; Stabilisation; Use of additives
- C07C 265/04: of a saturated carbon skeleton
- C07C 265/14: containing at least two isocyanate groups bound to the same carbon skeleton
- C07C 271/52: to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
- C08G 18/771: {oxygen}
- C08G 18/775: {sulfur}
- C08G 18/792: {formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates}
- C08G 18/798: {containing urethdione groups}
- C08K 5/005: {Stabilisers against oxidation, heat, light, ozone}
- C08K 5/0091: {Complexes with metal-heteroatom-bonds}
- C08K 5/01: Hydrocarbons {(C08K5/0091 takes precedence)}
- C08K 5/06: Ethers; Acetals; Ketals; Ortho-esters
- C08K 5/098: Metal salts of carboxylic acids
- C08K 5/205: Compounds containing [IMAGE cpc-sch-C08K-1010.gif] groups, e.g. carbamates
- C08K 5/21: Urea; Derivatives thereof, e.g. biuret
- C08K 5/3442: having two nitrogen atoms in the ring
- C08K 5/34924: {containing cyanurate groups; Tautomers thereof}
- C08K 5/372: Sulfides {, e.g. R-(S)x-R'}
- C08L 75/04: Polyurethanes
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

An isocyanate composition according to the present invention contains an isocyanate compound of formula (1) and/or (2) (wherein R1 represents a hydrogen or a monovalent organic group, and R2 represents a monovalent organic group), and, relative to the total mass of the isocyanate compound in the composition, 1.0 ppm by mass to 10% by mass of a compound of formula (3): R13—(COO—R14)a (wherein R13 represents an organic group with a valence of a, R14 represents a monovalent organic group, and a represents an integer of 1 or 2), which is different from the isocyanate compound, and/or, 1.0 ppm by mass to 10% by mass of a compound having an UV absorption in an area of decamer or higher isocyanates in a measurement spectrum of gel permeation chromatography.

## Claims

### Claim 1

An isocyanate composition comprising: an isocyanate compound of formula (1) and/or formula (2); and further comprising:
a compound of formula (3), which is different from the isocyanate compound, in an amount of 1.0 ppm by mass to 10% by mass, relative to a total mass of the isocyanate compound in the composition; and/or
a compound having an UV absorption in an area of decamer or higher isocyanates in a measurement spectrum of gel permeation chromatography, in an amount of 1.0 ppm by mass to 10% by mass, relative to the total mass of the isocyanate compound in the composition;
wherein R1 represents a hydrogen or a monovalent organic group, and R2 represents a monovalent organic group, and,
R13—(COO—R14)a (3)
wherein R13 represents an organic group with a valence of a, R14 represents a monovalent organic group, and a represents an integer of 1 or 2.

### Claim 2 (depends on 1)

The isocyanate composition according to claim 1, further comprising, relative to the total mass of the isocyanate compound in the composition,
1.0 ppm by mass to 10% by mass of saturated and/or unsaturated hydrocarbon compounds having a linear-chain structure, a branched-chain structure, or a cyclic structure, and/or,
1.0 ppm by mass to 10% by mass of a compound having at least one bond selected from the group consisting an ether bond and a thioether bond.

### Claim 3 (depends on 1)

The isocyanate composition according to claim 1, further comprising 1.0 ppm by mass to 10% by mass, relative to the total mass of the isocyanate compound in the composition, of a carbamate group-containing compound and/or a carbonic acid ester.

### Claim 4 (depends on 1)

The isocyanate composition according to claim 1, further comprising:
1.0 ppm by mass to 10% by mass, relative to the total mass of the isocyanate compound in the composition, of a basic amino compound, and/or,
a halogen ion, and/or, a hydrolyzable halogen compound.

### Claim 5 (depends on 1)

The isocyanate composition according to claim 1, further comprising, relative to the total mass of the isocyanate compound in the composition,
1.0 ppm by mass to 1.0×103 ppm by mass of a phosphoric acid and/or a phosphoric acid ester, and/or,
1.0 ppm by mass to 1.0×103 ppm by mass of a sulfuric acid and/or a sulfuric acid ester.

### Claim 6 (depends on 1)

The isocyanate composition according to claim 1, comprising, as the isocyanate compound, a trifunctional isocyanate compound having three isocyanate groups in a molecule thereof, and a difunctional isocyanate compound having two isocyanate groups in a molecule thereof.

### Claim 7

An isocyanate composition comprising an isocyanate compound of formula (1) and/or formula (2), comprising, relative to a total mass of the isocyanate compound in the composition, 1.0 ppm by mass to 1.0×103 ppm by mass of a phosphoric acid and/or a phosphoric acid ester, and/or, 1.0 ppm by mass to 1.0×103 ppm by mass of a sulfuric acid and/or a sulfuric acid ester,
wherein, R1 represents a hydrogen or a monovalent organic group, Fe represents a monovalent organic group, and.

### Claim 8 (depends on 1)

The isocyanate composition according to claim 1, wherein an amount of the isocyanate compound, relative to the total mass of the isocyanate composition, is 90% by mass or more.

### Claim 9 (depends on 1)

The isocyanate composition according to claim 1, comprising the isocyanate compound of formula (1), and the isocyanate compound has a structure derived from an α-amino acid.

### Claim 10 (depends on 1)

The isocyanate composition according to claim 1, comprising the isocyanate compound of formula (2), and the isocyanate compound has a structure derived from a β-amino acid.

### Claim 11 (depends on 9)

A method for producing an isocyanate composition of claim 9, comprising: preparing the isocyanate compound of formula (1) using a corresponding α-amino acid by fermentation; and mixing the isocyanate compound with a compound of formula (3) and/or a compound having an UV absorption in an area of decamer or higher isocyanates in a measurement spectrum of gel permeation chromatography, wherein the α-amino acid is an amino acid having a purity of 90% or more,
wherein R1 represents a hydrogen or a monovalent organic group, and R2 represents a monovalent organic group,
R13—(COO—R14)a (3)
wherein R13 represents an organic group with a valence of a, R14 represents a monovalent organic group, and a represents an integer of 1 or 2.

### Claim 12 (depends on 11)

The method for producing an isocyanate composition according to claim 11, further comprising a step in which the isocyanate compound is subjected to distillation purification.

### Claim 13 (depends on 1)

A method for producing an isocyanate polymer comprising a step in which an isocyanate compound contained in an isocyanate composition of claim 1 is reacted, wherein
the isocyanate polymer comprises a unit of formula (4) and at least one unit selected from the group consisting of units of formulae (5), (6), (7), (8), (9), (10), (11) and (12), and
a nitrogen atom constituting the isocyanate polymer is bonded with a carbon atom,
wherein each R3 independently represents a divalent hydrocarbon group and each R4 independently represents a monovalent organic group.

### Claim 14 (depends on 1)

The isocyanate composition according to claim 1, comprising the compound of formula (3), which is different from the isocyanate compound, in an amount of 1.0 ppm by mass to 10% by mass, relative to a total mass of the isocyanate compound in the composition.

### Claim 15 (depends on 1)

The isocyanate composition according to claim 1, comprising the compound having an UV absorption in an area of decamer or higher isocyanates in a measurement spectrum of gel permeation chromatography, in an amount of 1.0 ppm by mass to 10% by mass, relative to the total mass of the isocyanate compound in the composition.

### Claim 16 (depends on 1)

The isocyanate composition according to claim 1, comprising the compound of formula (3), which is different from the isocyanate compound, in an amount of 3.0 ppm by mass to 1.0×103 ppm by mass, relative to a total mass of the isocyanate compound in the composition.

### Claim 17 (depends on 1)

The isocyanate composition according to claim 1, comprising the compound of formula (3), which is different from the isocyanate compound, in an amount of 5.0 ppm by mass to 3.0×103 ppm by mass, relative to a total mass of the isocyanate compound in the composition.

### Claim 18 (depends on 1)

The isocyanate composition according to claim 1, comprising the compound having an UV absorption in an area of decamer or higher isocyanates in a measurement spectrum of gel permeation chromatography, in an amount of 3.0 ppm by mass to 3.0×103 ppm by mass, relative to the total mass of the isocyanate compound in the composition.

### Claim 19 (depends on 1)

The isocyanate composition according to claim 1, comprising the compound having an UV absorption in an area of decamer or higher isocyanates in a measurement spectrum of gel permeation chromatography, in an amount of 10 ppm by mass to 1.0×103 ppm by mass, relative to the total mass of the isocyanate compound in the composition.

### Claim 20 (depends on 1)

The isocyanate composition according to claim 1, wherein the monovalent organic group of R1 represents a group represented by —C(═O)OR2 or —CH2—C(═O)O—R2.

### Claim 21 (depends on 7)

An isocyanate composition according to claim 7, wherein the monovalent organic group of R1 represents a group represented by —C(═O)OR2 or —CH2—C(═O)O—R2.

### Claim 22 (depends on 11)

The method according to claim 11, wherein the monovalent organic group of R1 represents a group represented by —C(═O)OR2 or —CH2—C(═O)O—R2.