IP Library Granted Patent US 11,078,321
Granted Patent B2
US 11,078,321 · App. 16/340,532 · Granted Aug 3, 2021

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

Inventors: Nobuhisa Miyake (Tokyo, JP); Masaaki Shinohata (Tokyo, JP); Atsushi Ohkubo (Tokyo, JP); Koichi Nakaoka (Tokyo, JP); Yuji Kosugi (Tokyo, JP)
Assignee: Asahi Kasei Kabushiki Kaisha
C08G18/725C07C263/18C07C265/04C07C265/14C07C271/52C08G18/771C08G18/775C08G18/792C08G18/798C08K5/005C08K5/0091C08K5/01C08K5/06C08K5/098C08K5/205C08K5/21C08K5/3442C08K5/34924C08K5/372
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Quick Facts
Patent No.
US 11,078,321
App. No.
16/340,532
Granted
Aug 3, 2021
Kind
B2
Abstract

An isocyanate composition according to the present invention contains an isocyanate compound of formula (1) and/or (2) (wherein R 1 represents a hydrogen or a monovalent organic group, and R 2 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): R 13 —(COO—R 14 )a (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), 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 (40)

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 to claim 7 , 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 .

22. The method according to claim 11 , 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 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 9, 2019
From: MIYAKE, NOBUHISA; SHINOHATA, MASAAKI; OHKUBO, ATSUSHI; NAKAOKA, KOICHI; KOSUGI, YUJI
To: ASAHI KASEI KABUSHIKI KAISHA
Reel/Frame 048836/0415 →
Priority Claims (1)
JP JP2016-203101 · Oct 14, 2016 · national
Continuity (1)
Related Publication 20200048403A1 · Feb 13, 2020