Fluorine-containing nitrile-oxide compound

Patent metadata

Field	Value
Publication number	US-9637446-B2
Application number	US-201414772908-A
Country	US
Kind code	B2
Filing date	Mar 7, 2014
Priority date	Mar 7, 2013
Publication date	May 2, 2017
Grant date	May 2, 2017

Abstract

A stable and easily producible compound of the formula (I):

wherein R 1 represents a hydrocarbon group; and R 2 and R 3 represent each independently a hydrogen atom or a hydrocarbon group: provided that in at least one of R 1 , R 2 and R 3 , at least one hydrogen atoms are substituted by a fluorine atom, and each of R 1 , R 2 and R 3 is attached via its carbon atom to a carbon atom to which a nitrileoxide group is attached.

First claim

The invention claimed is:

1. A compound of the formula (I):

wherein
R 1 represents a fluoroalkyl group or a group substituted by one or more fluoroalkyl groups;
R 2 and R 3 represent each independently a hydrogen atom or a hydrocarbon group; and
a carbon atom of R 1 is attached to a carbon atom to which a nitrile oxide is attached, and when one or both of R 2 and R 3 is represented by a hydrocarbon group, a carbon atom of the hydrocarbon group is attached to a carbon atom to which a nitrile oxide group is attached.

2. The compound according to claim 1 wherein at least one of R 1 , R 2 and R 3 are a perfluoroalkyl group or comprise one or more perfluoroalkyl groups.

3. The compound according to claim 1 wherein R 1 represents a perfluoroalkyl group, or an alkyl group substituted by one or more perfluoroalkyl groups.

4. The compound according to claim 1 which meets one or more of the following items (b)-(c);
(b) R 2 is an aryl group, a tert-alkyl group or a sec-alkyl group which may be substituted by one or more substituents; and
(c) R 3 is an aryl group, a tert-alkyl group or a sec-alkyl group which may be substituted by one or more substituents.

5. The compound according to claim 1 wherein at least one of R 2 and R 3 are an aryl group, a tert-alkyl group or a sec-alkyl group which may be substituted by one or more substituents.

6. The compound according to claim 1 wherein
R 1 is a perfluoroalkyl group, or an alkyl group substituted by one or more perfluoroalkyl groups; and
R 2 and R 3 are a phenyl group which may be substituted by one or more substituents.

7. The compound according to claim 1 wherein
at least one of R 2 and R 3 are a perfluoroalkyl group or an alkyl group which is substituted by one or more perfluoroalkyl groups.

8. The compound according to claim 2 wherein the perfluoroalkyl group is —C m F 2m+1 wherein m represents an integer of 1-16.

9. A process for preparing the compound of the formula (I) described in claim 1 comprising the following steps:
(i) reacting a compound of the formula (II):

wherein: R 2 and R 3 are as defined in claim 1 with a compound of the formula (III):
R 1 L  (III)

wherein:
R 1 is as defined in claim 1 ;
L represents MX t ;
M represents Li, Zn, Na, K, Al, Cu, B, Si, Ti, Cr, Fe, Ni, Pd, Pt, Rh, Ru, Ir, Mg or Sm;
X represents a halogen atom or an alkoxy group; and
t represents an integer of 0-6; and then,

(ii) dehydrating.

10. A composition applied to a material containing a group reactive with a nitrileoxide group which comprises one or more compounds according to claim 1 .

11. The composition according to claim 10 which is a surface treatment agent.

12. The composition according to claim 10 which is a modifying agent.

13. An article comprising a base material and a layer which is formed from the surface treatment agent according to claim 11 on the surface of the base material.

14. A modified polymer material treated with the modifying agent according to claim 12 .

Assignees

• Daikin Ind Ltd
• Tokyo Inst Tech

Inventors

• Kanbara Tadashi
• Noguchi Tsuyoshi
• Mouri Haruhiko
• Takata Toshikazu
• Koyama Yasuhito
• Uchida Satoshi
• Wang Chengang
• Sumitra Cheawchan

Classifications

• C08F8/30

  Introducing nitrogen atoms or nitrogen-containing groups · CPC title

• C07C291/06 Primary

  Nitrile oxides · CPC title