Fluorine-containing polymer and treatment agent

Patent metadata

Field	Value
Publication number	US-2016237614-A1
Application number	US-201415031104-A
Country	US
Kind code	A1
Filing date	Oct 22, 2014
Priority date	Oct 23, 2013
Publication date	Aug 18, 2016
Grant date	—

Abstract

A fluorine-containing polymer including: (a) a repeat unit in which the α-position is an acrylate ester monomer substituted with a monovalent organic group or a halogen atom and which is derived from a fluorine-containing monomer having a fluoroalkyl group; (b) a repeat unit which is an alkyl acrylate having a C 6-13 alkyl group and is derived from a non-fluorine monomer; and (c) a repeat unit derived from a non-fluorine (meth)acrylate monomer having a cyclic hydrocarbon group. Also disclosed is a surface treatment agent containing the fluorine-containing polymer, a method of treating a substrate with the surface treatment agent and a treated substrate.

First claim

1 . A fluorine-containing polymer comprising:
(a) repeating units derived from a fluorine-containing monomer having a fluoroalkyl group which is an acrylate ester monomer substituted at α-position with a monovalent organic group or a halogen atom, (b) repeating units derived from a fluorine-free monomer which is alkyl acrylate having an alkyl group having 6-13 carbon atoms, and (c) repeating units derived from a fluorine-free (meth)acrylate monomer having a cyclic hydrocarbon group.

2 . The fluorine-containing polymer according to claim 1 , wherein the fluorine-containing monomer (a) is a compound represented by the formula:
CH 2 ═C(—X)—C(═O)—Y—Z—Rf  (I)
wherein X is a linear or branched alkyl group having 2-21 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a CFX 1 X 2 group (where X 1 and X 2 are a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom or an iodine atom), a cyano group, a linear or branched fluoroalkyl group having 1-21 carbon atoms, a substituted or unsubstituted benzyl group, or a substituted or unsubstituted phenyl group;
Y is —O— or —NH—;
Z is an aliphatic group having 1-10 carbon atoms, an aromatic group or cycloaliphatic group having 6-18 carbon atoms,
a —CH 2 CH 2 N(R 1 )SO 2 — group (where R 1 is an alkyl group having 1-4 carbon atoms), a —CH 2 CH(OZ 1 )CH 2 -(Ph-O) p — group (where Z 1 is a hydrogen atom or an acetyl group, Ph is a phenylene group, and p is 0 or 1), a —(CH 2 ) n -Ph-O— group (where Ph is a phenylene group and n is 0-10) a —(CH 2 ) m —SO 2 —(CH 2 ) n — group or a —(CH 2 ) m —S—(CH 2 ) n — group (where m is 1-10 and n is 0-10),
Rf is a linear or branched fluoroalkyl group having 1 to 20 carbon atoms.

3 . The fluorine-containing polymer according to claim 1 , wherein the fluorine-containing monomer (a) is alkyl acrylate which has the α-position substituted with a chlorine atom.

4 . The fluorine-containing polymer according to claim 2 , wherein, in the fluorine-containing monomer (a), the number of carbon atoms of Rf is from 1 to 6.

5 . The fluorine-containing polymer according to claim 1 , wherein the alkyl acrylate (b) is an alkyl acrylate represented by the formula:
CH 2 ═CA 1 COOA 2
wherein A 1 is a hydrogen atom, a methyl group or a halogen atom other than a fluorine atom (for example, a chlorine atom, a bromine atom, and an iodine atom), and A 2 is an alkyl group expressed by C n H 2n+1 (n=6-13).

6 . The fluorine-containing polymer according to claim 1 , wherein the alkyl acrylate monomer (b) is at least one selected from the group consisting of hexyl (meth)acrylate, heptyl (meth)acrylate, octyl (meth)acrylate, nonyl (meth)acrylate, decyl (meth)acrylate, undecyl (meth)acrylate, lauryl (meth)acrylate and tridecyl (meth)acrylate.

7 . The fluorine-containing polymer according to claim 1 , wherein the cyclic hydrocarbon group-containing acrylate ester monomer (c) is a compound represented by the formula:
CH 2 ═CA-C(═O)—O-Q
wherein A is a hydrogen atom, a methyl group or a halogen atom other than a fluorine atom (for example, a chlorine atom, a bromine atom, and a iodine atom), and Q is a cyclic hydrocarbon group.

8 . The fluorine-containing polymer according to claim 1 , wherein the fluorine-containing polymer further comprises at least one repeating unit selected from the group consisting of:
(d) repeating units derived from a halogenated olefin monomer, and (e) repeating units derived from a fluorine-free monomer other than the monomers (b)-(d).

9 . The fluorine-containing polymer according to claim 8 , wherein the halogenated olefin monomer (d) is an olefin having 2-20 carbon atoms and substituted by 1-10 chlorine atoms, bromine atoms or iodine atoms.

10 . The fluorine-containing polymer according to claim 1 , wherein the amount of the acrylate ester monomer (b) is 5 to 300 parts by weight and the amount of the fluorine-free acrylate monomer (c) is 0.1 to 800 parts by weight, based on 100 parts by weight of fluorine-containing monomer (a).

11 . A surface treatment agent which comprises the fluorine-containing polymer according to claim 1 .

12 . The surface treatment agent according to claim 11 which is a water- and oil-repellent agent, a soil resistant agent or a soil release agent.

13 . The surface treatment agent according to claim 11 which contains also an aqueous medium.

14 . A method of treating a substrate, which comprises treating the substrate with the surface treatment agent according to claim 11 .

15 . A substrate which is treated with the surface treatment agent according to claim 11 .

Assignees

• Daikin Ind Ltd

Inventors

• Kawabe Rumi
• Hara Ryousuke
• Sawaki Kyouhei
• Yamamoto Ikuo

Classifications

• D06M15/248

  containing chlorine · CPC title

• C08F220/24

  containing perhaloalkyl radicals · CPC title

• D06M2200/11

  Oleophobic properties · CPC title

• D06M15/277 Primary

  containing fluorine · CPC title

• C08F220/22

  Esters containing halogen · CPC title