Water- and oil-repellent antifouling finishing agent

• US 5,069,941 A
• Filed: 02/07/1991
• Issued: 12/03/1991
• Est. Priority Date: 03/16/1988
• Status: Expired due to Term

• Current Assignee: Daikin Industries Ltd
• Original Assignee: Daikin Industries Ltd
• Inventors: Ueda, Akihiko, Inukai, Hiroshi, Kitahara, Takahiro, Ohmori, Akira
• Primary Examiner(s): Schofer, Joseph L.
• Assistant Examiner(s): SAROFIM, NABIL F
• Application Number:
  US07/652,402
• Time in Patent Office: 299 Days
• Field of Search: 427/385.5, 427/393.4
• US Class Current: 427/385.5
• CPC Class Codes: D06M 15/277 containing fluorine

Abstract

This invention provides an antifouling finishing agent comprising a fluorine-containing polymer comprising at least 50% by weight of a fluorine-containing acrylate represented by the formula ##STR1## wherein Y is alkylene group having 1 to 3 carbon atoms, a group of the formula --CH₂ CH₂ N(R)SO₂ -- (wherein R is alkyl group having 1 to 4 carbon atoms) or a group of the formula --CH₂ CH(OZ)CH₂ -- (wherein Z is hydrogen atom or acetyl group), and R_f is fluoroalkyl group having 3 to 21 carbon atoms or fluoralkyl group having 3 to 21 carbon atoms and containing 1 to 10 oxygen atoms in the carbon chain (provided that no oxygen atom is adjacent or closest to other oxygen atom), said fluoroalkyl groups having at least 5 fluorine atoms.

Claims

1. A method of providing an article surface with anti-fouling properties which comprises applying to said surface a solution of an anti-fouling finishing agent comprising at least 50% by weight of a fluorine-containing acrylate represented by the formula ##STR12## wherein Y is alkylene group having 1 to 3 carbon atoms, a group of the formula --CH₂ CH₂ N(R)SO₂ -- (wherein R is alkyl group having 1 to 4 carbon atoms) or a group of the formula --CH₂ CH(OZ)CH₂ -- (wherein Z is hydrogen atom or acetyl group), and R_f is fluoroalkyl group having 3 to 21 carbon atoms and containing 1 to 10 oxygen atoms in the carbon chain (provided that no oxygen atom is adjacent or closest to other oxygen atom), said fluoroalkyl groups having at least 5 fluorine atoms and drying the applied solution.

2. A method according to claim 1 wherein the fluorine-containing polymer is a copolymer comprising:

(a) about 65 to about 90% by weight of a fluorine-containing acrylate represented by the formula ##STR13## wherein Y is alkylene group having 1 to 3 carbon atoms, a group of the formula --CH₂ CH₂ N(R)SO₂ -- (wherein R is alkyl group having 1 to 4 carbon atoms) or a group of the formula --CH₂ CH(OZ)CH₂ -- (wherein Z is hydrogen atom or acetyl group), and R_f is fluoroalkyl group having 3 to 21 carbon atoms or fluoroalkyl group having 3 to 21 carbon atoms and containing 1 to 10 oxygen atoms in the carbon chain (provided that no oxygen atom is adjacent to other oxygen atom), said fluoroalkyl groups having at least 5 fluorine atoms;

(b) about 10 to about 35% by weight of an acrylate or methacrylate represented by the formula ##STR14## wherein A is hydrogen atom, fluorine atom, chlorine atom or methyl group and B is alkyl group having 1 to 10 carbon atoms, alicyclic group or aromatic group having 6 to 10 carbon atoms, or fluoroalkyl group having 1 to 10 carbon atoms; and

(c) 0 to about 10% by weight of an ethylenically unsaturated monomer.

3. A method according to claim 1 wherein:

(i) the fluorine-containing acrylate (a) is a compound represented by the formula ##STR15## wherein m is an integer of 1 to 3 and n is an integer of 5 to 13;

(ii) the acrylate or methacrylate (b) is a compound represented by the formula ##STR16## wherein A'"'"' is hydrogen atom, fluorine atom or methyl group and B'"'"' is methyl group, ethyl group, phenyl group, benzyl group, cyclohexyl group, tert-butyl group, neopentyl group, tricyclodecanyl group, bornyl group, isobornyl group, dicyclopentenyl group or phenoxyethyl group; and

(iii) the ethylenically unsaturated monomer (c) is an acrylate or methacrylate having functional group.

4. A method according to claim 1 wherein the fluorine-containing polymer has a glass transition temperature or a melting point of 35°

C. or higher.

5. A method according to claim 1 wherein the fluorine-containing polymer has a number-average molecular weight of about 10000 to about 4000000 as determined by gel permeation chromatography.