Isocyanate composition, method for producing isocyanate composition, and method for producing isocyanate polymer

Patent metadata

Field	Value
Publication number	US-11118001-B2
Application number	US-201716340532-A
Country	US
Kind code	B2
Filing date	Oct 13, 2017
Priority date	Oct 14, 2016
Publication date	Sep 14, 2021
Grant date	Sep 14, 2021

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.

First claim

The invention claimed is:

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 R 1 represents a hydrogen or a monovalent organic group, and R 2 represents a monovalent organic group, and,
R 13 —(COO—R 14 ) a   (3)

wherein R 13 represents an organic group with a valence of a, R 14 represents a monovalent organic group, and a represents an integer of 1 or 2.

2. 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.

3. 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.

4. 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.

5. 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 1.0×10 3 ppm by mass of a phosphoric acid and/or a phosphoric acid ester, and/or,
1.0 ppm by mass to 1.0×10 3 ppm by mass of a sulfuric acid and/or a sulfuric acid ester.

6. 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.

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 1.0×10 3 ppm by mass of a phosphoric acid and/or a phosphoric acid ester, and/or, 1.0 ppm by mass to 1.0×10 3 ppm by mass of a sulfuric acid and/or a sulfuric acid ester,

wherein, R 1 represents a hydrogen or a monovalent organic group, Fe represents a monovalent organic group, and.

8. 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.

9. 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.

10. 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.

11. 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 R 1 represents a hydrogen or a monovalent organic group, and R 2 represents a monovalent organic group,
R 13 —(COO—R 14 ) a   (3)

wherein R 13 represents an organic group with a valence of a, R 14 represents a monovalent organic group, and a represents an integer of 1 or 2.

12. 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.

13. 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 R 3 independently represents a divalent hydrocarbon group and each R 4 independently represents a monovalent organic group.

14. 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.

15. 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.

16. 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 1.0×10 3 ppm by mass, relative to a total mass of the isocyanate compound in the composition.

17. 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 3.0×10 3 ppm by mass, relative to a total mass of the isocyanate compound in the composition.

18. 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 3.0×10 3 ppm by mass, relative to the total mass of the isocyanate compound in the composition.

19. 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 1.0×10 3 ppm by mass, relative to the total mass of the isocyanate compound in the composition.

20. The isocyanate composition according to claim 1 , wherein the monovalent organic group of R 1 represents a group represented by —C(═O)OR 2 or —CH 2 —C(═O)O—R 2 .

21. An isocyanate composition according t

Assignees

• Asahi Chemical Ind

Inventors

• Miyake Nobuhisa
• Shinohata Masaaki
• Ohkubo Atsushi
• Nakaoka Koichi
• Kosugi Yuji

Classifications

• C07C271/52

  to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups · CPC title

• C08K5/01

  Hydrocarbons {(C08K5/0091 takes precedence)} · CPC title

• C08K5/372

  Sulfides {, e.g. R-(S)x-R'} · CPC title

• C08K5/098

  Metal salts of carboxylic acids · CPC title

• C07C263/18

  Separation; Purification; Stabilisation; Use of additives · CPC title