Fluorine-containing coating agents

• US 4,804,709 A
• Filed: 03/01/1988
• Issued: 02/14/1989
• Est. Priority Date: 12/24/1985
• Status: Expired due to Fees

• Current Assignee: Shin-Etsu Chemical Company Limited
• Original Assignee: Shin-Etsu Chemical Company Limited
• Inventors: Yamamoto, Yasushi, Yamaguchi, Kouichi, Takago, Toshio
• Primary Examiner(s): Marquis, Melvyn I.
• Application Number:
  US07/162,682
• Time in Patent Office: 350 Days
• Field of Search: 525/102, 528/25, 528/18, 528/17
• US Class Current: 525/102
• CPC Class Codes: C08F 14/18 Monomers containing fluorine
• CPC Class Codes: C08F 8/42 Introducing metal atoms or metal-containing groups

Abstract

A fluorine-containing coating agent which can be used for forming a fluorocarbon resin coating film on a substrate comprises a polymer which has a fluorine-containing polymer as a main chain and an alkoxysilyl group in the side chain and which is obtained by the reaction of a hydroxyl group of a fluorine-containing polymer having the hydroxyl group in the side chain with an isocyanato group of an alkoxysilane having the isocyanato group. The fluorine-containing polymer having a hydroxyl group in the side chain is a copolymer of a fluoro-olefin and a hydroxyalkyl vinyl ether having a straight or branched alkyl group having 2 to 5 carbon atoms. The alkoxysilane having an isocyanato group is a compound represented by the following formula:

OCN(CH.sub.2).sub.3 SiX.sub.n R.sub.(3-n)                  (I)

wherein

R is hydrogen or a monovalent hydrocarbon group haviang 1 to 10 carbon atoms,

X is an alkoxyl group having 1 to 5 carbon atoms, and

n is an integer of 1 to 3.

Claims

1. A fluorine-containing coating agent which can be used to form a fluorocarbon resin coating film on a substrate comprising a polymer which has a fluorine-containing polymer as a main chain and an alkoxysilyl group in the side chain and which is obtained by the reaction of a hydroxyl group of a fluorine-containing polymer having the hydroxyl group in the side chain with an isocyanato group of an alkoxysilane having the isocyanato group, wherein said fluorine-containing polymer having a hydroxyl group in the side chain is a copolymer of a fluoro-olefin and a hydroxyalkyl vinyl ether having a straight or branched alkyl group having 2 to 5 carbon atoms, and said alkoxysilane having an isocyanato group is a compound represented by the following formula:

space="preserve" listing-type="equation">OCN(CH.sub.2).sub.3 SiX.sub.n R.sub.(3-n) (I)

wherein

R is hydrogen or a monovalent hydrocarbon group having 1 to 10 carbon atoms,

X is an alkoxyl group having 1 to 5 carbon atoms, and

n is an integer of 1 to 3.

2. The fluorine-containing coating agent in accordance with claim 1, wherein said fluorine-containing polymer having the hydroxyl group is a copolymer of a perhalogenated fluoro-olefin, the hydroxyalkyl vinyl ether, and an alkyl vinyl ether having an alkyl group selected from the group consisting of a cyclohexyl group and straight and branched alkyl groups having 1 to 8 carbon atoms, and the fluoro-olefin content based on the total monomer components is 40 to 70% by mole.

3. The fluorine-containing coating agent in accordance with claim 1, wherein said fluoro-olefin is a perhalogenated fluoro-olefin.

4. The fluorine-containing coating agent in accordance with claim 1, wherein said fluoro-olefin is chlorotrifluoroethylene, tetrafluoroethylene, or mixtures thereof.

5. The fluorine-containing coating agent in accordance with claim 1, wherein said hydroxyalkyl group of the hydroxyalkyl vinyl ether is a hydroxybutyl group.

6. The fluorine-containing coating agent in accordance with claim 1, wherein said alkoxysilane having an isocyanato group is one or more compounds selected from the group consisting of gamma-isocyanatopropyl methyl diethoxy silane, gamma-isocyanatopropyl triethoxy silane, gamma-isocyanatopropyl methyl dimethoxy silane, and gamma-isocyanatopropyl trimethoxy silane.

7. The fluorine-containing coating agent in accordance with claim 1, wherein said copolymer has 40 to 65% by mole of the fluoro-olefin, 5 to 40% by mole of cyclohexyl vinyl ether, 5 to 40% by mole of alkyl vinyl ethers other than cyclohexyl vinyl ether, and 3 to 15% by mole of hydroxyalkyl vinyl ethers.

8. The fluorine-containing coating agent in accordance with claim 1, wherein said fluorine-containing polymer having a hydroxy group has a molecular weight in the range from 1000 to 200,000 and 2 to 50 hydroxyl groups in the molecule.

9. The fluorine-containing coating agent in accordance with claim 1, which further includes a member selected from the group consisting of pigments, dyestuffs, flexibility-imparting agents, and antioxidants.