Nitrileoxide compound

Patent metadata

Field	Value
Publication number	US-10633333-B2
Application number	US-201615556787-A
Country	US
Kind code	B2
Filing date	Mar 10, 2016
Priority date	Mar 10, 2015
Publication date	Apr 28, 2020
Grant date	Apr 28, 2020

Abstract

The present invention provides a compound of the formula (I):

wherein, A is R 6 (R 7 ) s , N, O, S, or —NR 5 —; R 6 is an s-valent organic group; R 7 is each independently, —O—, —S—, —NR 5 — or —O—P(═O)OR 4′ —; R 2 and R 3 are each independently a hydrogen atom or a hydrocarbon group; R 4′ is each independently, a hydrocarbon group; R 5 is each independently, a hydrogen atom or a hydrocarbon group; and s is an integer of 1-10.

First claim

The invention claimed is:

1. A compound of the formula (I):

wherein:
A is R 4 O—, R 4 —NR 5 —, (R 4 O) 2 —P(═O)—, R 4 S—, R 6 (R 7 ) s , N, O, S, or —NR 5 —;
R 2 and R 3 are each independently a hydrogen atom, an aryl group, a tert-alkyl group, or a sec-alkyl group, which may have one or more substituents, and at least one of R 2 and R 3 is an aryl group, a tert-alkyl group, or a sec-alkyl group, which may have one or more substituents;
s is an integer of 1-10,
when A is R 4 O—, R 4 —NR 5 —, or (R 4 O) 2 —P(═O)—, then s is 1,
R 4 is R 13 —(R 14 ) i —R 15 —
R 13 is a hydrogen atom, a halogen atom, or a methyl group which may be substituted by a halogen atom,
R 14 is each independently at each occurrence an oxygen atom, an alkylene group, a cycloalkylene group, a heterocycloalkylene group, an arylene group, a heteroarylene group, a divalent polyalkylether group or a divalent siloxane group,
when A is R 4 O—, R 15 is an alkylene group having 2-3 carbon atoms optionally substituted by one or more substituents, wherein the substituent of alkylene is selected from the group consisting of an oxygen atom; a halogen atom; a hydroxyl group; an unsubstituted, mono-substituted or di-substituted amino group; a nitro group; an azide group; a C 1-16 alkyl group, a C 3-16 cycloalkyl group, a C 3-16 cycloalkenyl group, a C 6-16 heterocycloalkyl group, a C 6-16 heterocycloalkenyl group, a C 6-16 aryl group, a C 6-16 heteroaryl group, a C 1-16 alkoxy group, a C 6-16 aryloxy, a C 1-16 alkylthio or a C 1-20 (poly)alkyl ether group which may be substituted by one or more halogen atoms; —O—C(O)—OR a , —O—C(O)—NR a 2 , —C(O)—R a , —C(O)—OR a , —NR a —C(O)—R a , —NR a —C(NR a )—R a , —C(NR a )—R a or —C(NR a )—NR a 2 , wherein R a represents each independently a hydrogen atom, a C 1-16 alkyl group, a C 2-16 alkenyl group, a C 2-16 alkynyl group, a C 3-16 cycloalkyl group, a C 3-16 cycloalkenyl group, a C 6-16 heterocycloalkyl group, a C 6-16 heterocycloalkenyl group, a C 6-16 aryl group or a C 6-16 heteroaryl group,
when A is R 4 —NR 5 — or (R 4 O) 2 —P(═O)—, R 15 is an alkylene group optionally substituted by one or more substituents, wherein the substituent of alkylene is selected from the group consisting of an oxygen atom; a halogen atom; a hydroxyl group; an unsubstituted, mono-substituted or di-substituted amino group; a nitro group; an azide group; a C 1-16 alkyl group, a C 2-16 alkynyl group, a C 3-16 cycloalkyl group, a C 3-16 cycloalkenyl group, a C 6-16 heterocycloalkyl group, a C 6-16 heterocycloalkenyl group, a C 6-16 aryl group, a C 6-16 heteroaryl group, a C 1-16 alkoxy group, a C 6-16 aryloxy, a C 1-16 alkylthio or a C 1-20 (poly)alkyl ether group which may be substituted by one or more halogen atoms; —O—C(O)—OR a , —O—C(O)—NR a 2 , —C(O)—R a , —C(O)—OR a , —NR a —C(O)—R a , —NR a —C(NR a )—R a , —C(NR a )—R a or —C(NR a )—NR a 2 , wherein R a represents each independently a hydrogen atom, a C 1-16 alkyl group, a C 2-16 alkenyl group, a C 2-16 alkynyl group, a C 3-16 cycloalkyl group, a C 3-16 cycloalkenyl group, a C 6-16 heterocycloalkyl group, a C 6-16 heterocycloalkenyl group, a C 6-16 aryl group or a C 6-16 heteroaryl group,
l is an integer of 0-5,
R 5 is each independently a hydrogen atom or a hydrocarbon group;
when A is R 4 S—, then s is 1,
R 4 is R 13 —(R 14 ) l —R 15 —,
R 13 is a hydrogen atom, a halogen atom, or a methyl group which may be substituted by a halogen atom,
R 14 is each independently at each occurrence an oxygen atom, an alkylene group having 1-20 carbon atoms, a cycloalkylene group, a heterocycloalkylene group, an arylene group, a heteroarylene group, a divalent polyalkylether group or a divalent siloxane group,
R 15 is an alkylene group having 3 carbon atoms,
l is an integer of 0-5;
when A is R 6 (R 7 ) s , then s is an integer of 2-10,
R 6 is an s-valent organic group,
R 7 is each independently —O—, —S—, —NR 5 — or —O—P(═O)OR 4′ —,
R 4′ is each independently a hydrocarbon group,
R 5 is each independently a hydrogen atom or a hydrocarbon group;
when A is N, then s is 3, and
when A is O, S or —NR 5 —, then s is 2, and R 5 is a hydrogen atom or a hydrocarbon group.

2. The compound according to claim 1 , which is a compound of the formula (II):

wherein:
R 2 and R 3 are each independently a hydrogen atom, an aryl group, a tert-alkyl group, or a sec-alkyl group, which may have one or more substituents, and at least one of R 2 and R 3 is an aryl group, a tert-alkyl group, or a sec-alkyl group, which may have one or more substituents;
when R 1 is R 4 O—, R 4 —NR 5 —, or (R 4 O) 2 —P(═O)—,
R 4 is R 13 —(R 14 ) l —R 15 —,
R 13 is a hydrogen atom, halogen atom, or a methyl group which may be substituted by a halogen atom,
R 14 is each independently at each occurrence an oxygen atom, an alkylene group, a cycloalkylene group, a heterocycloalkylene group, an arylene group, a heteroarylene group, a divalent polyalkylether group or a divalent siloxane group,
when R 1 is R 4 O—, R 15 is an alkylene group having 2-3 carbon atoms optionally substituted by one or more substituents, wherein the substituent of alkylene is selected from the group consisting of an oxygen atom; a halogen atom; a hydroxyl group; an unsubstituted, mono-substituted or di-substituted amino group; a nitro group; an azide group; a C 1-16 alkyl group, a C 3-16 cycloalkyl group, a C 3-16 cycloalkenyl group, a C 6-16 heterocycloalkyl group, a C 6-16 heterocycloalkenyl group, a C 6-16 aryl group, a C 6-16 heteroaryl group, a C 1-16 alkoxy group, a C 6-16 aryloxy, a C 1-16 alkylthio or a C 1-20 (poly)alkyl ether group which may be substituted by one or more halogen atoms; —O—C(O)—OR a , —O—C(O)—NR a 2 , —C(O)—R a , —C(O)—OR a , —NR a —C(O)—R a , —NR a —C(NR a )—R a , —C(NR a )—R a or —C(NR a )—NR a 2 , wherein R a represents each independently a hydrogen atom, a C 1-16 alkyl group, a C 2-16 alkenyl group, a C 2-16 alkynyl group, a C 3-16 cycloalkyl group, a C 3-16 cycloalkenyl group, a C 6-16 heterocycloalkyl group, a C 6-16 heterocycloalkenyl group, a C 6-16 aryl group or a C 6-16 heteroaryl group,
When R 1 is R 4 —NR 5 — or (R 4 O) 2 —P(═O)—, R 15 is an alkylene group optionally substituted by one or more substituents, wherein the substituent of alkylene is selected from the group consisting of an oxygen atom; a halogen atom; a hydroxyl group; an unsubstituted, mono-substituted or di-substituted amino group; a nitro group; an azide group; a C 1-16 alkyl group, a C 2-16 alkynyl group, a C 3-16 cycloalkyl group, a C 3-16 cycloalkenyl group, a C 6-16 heterocycloalkyl group, a C 6-16 heterocycloalkenyl group, a C 6-16 aryl group, a C 6-16 heteroaryl group, a C 1-16 alkoxy group, a C 6-16 aryloxy, a C 1-16 alkylthio or a C 1-20 (poly)alkyl ether group which may be substituted by one or more halogen atoms; —O—C(O)—OR a , —O—C(O)—NR a 2 , —C(O)—R a , —C(O)—OR a , —NR a —C(O)—R a , —NR a —C(NR a )—R a , —C(NR a )—R a or —C(NR a )—NR a 2 , wherein R a represents each independently a hydrogen atom, a C 1-16 alkyl group, a C 2-16 alkenyl group, a C 2-16 alkynyl group, a C 3-16 cycloalkyl group, a C 3-16 cycloalkenyl group, a C 6-16 heterocycloalkyl group, a C 6-16 heterocycloalkenyl group, a C 6-16 aryl group or a C 6-16 heteroaryl group,
l is an integer of 0-5,
R 5 is a hydrogen ato

Assignees

• Daikin Ind Ltd
• Tokyo Inst Tech

Inventors

• Kanbara Tadashi
• Noguchi Tsuyoshi
• Takata Toshikazu
• Sogawa Hiromitsu
• Tsutsuba Toyokazu

Classifications

• C07C291/06 Primary

  Nitrile oxides · CPC title

• C08K5/32

  Compounds containing nitrogen bound to oxygen · CPC title

• C07F9/40

  Esters thereof · CPC title

• C07C323/47

  to oxygen atoms · CPC title

• C08L101/00

  Compositions of unspecified macromolecular compounds · CPC title