Fluorine-containing nitrile-oxide compound
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.
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 .