US 8,557,939 B2 · Antifouling composition, method for its production and article treated therewith

Abstract

To provide an antifouling composition which is a fluorine-type antifouling composition using a short chain perfluoroalkyl group and which is excellent in antifouling properties and water/oil repellency and presents good durability against washing. An antifouling composition comprising a fluorocopolymer which comprises from 30 to 65 mass % of polymerized units (a) having a C1-6 perfluoroalkyl group, from 1 to 67 mass % of polymerized units (b1) having —(C2H4O)— and from 3 to 34 mass % of polymerized units (b2) having —(C4H8O)—, wherein the content of —(C2H4O)— is from 20 to 65 mass %, and the content of —(C4H8O)— is from 2 to 13 mass %.

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Claims19

Dependent claims

An antifouling composition comprising a fluorocopolymer which comprises from 30 to 65 mass % of polymerized units (a) based on the following monomer (a), from 1 to 67 mass % of polymerized units (b1) based on the following monomer (b1) and from 3 to 34 mass % of polymerized units (b2) based on the following monomer (b2), wherein the content of —(C2H4O)— is from 20 to 65 mass %, and the content of —(C4H8O)— is from 2 to 13 mass %:

monomer (a):
a compound represented by (Z—Y)nX, wherein Z is a C1-6 perfluoroalkyl group or a monovalent group represented by CmF2m+1O(CFWCF2O)dCFK— wherein m is an integer of from 1 to 6, d is an integer of from 0 to 4, and each of W and K which are independent of each other, is a fluorine atom or a trifluoromethyl group, Y is a bivalent organic group or a single bond, n is 1 or 2, when n is 1, X is —CR═CH2, —COOCR═CH2, —OCOCR═CH2, —OCH2-φ-CR═CH2 or —OCH═CH2, and when n is 2, X is —CH[—(CH2)pCR═CH2]—, —CH[—CH2)pCOOCR═CH2]—, —CH[—(CH2)pOCOCR═CH2]—or —OCOCH═CHCOO—, R is a hydrogen atom, a methyl group or a halogen atom, φ is a phenylene group, and p is an integer of from 0 to 4,
monomer (b1):
a compound represented by CH2═CR1-G1-(C2H4O)q1—R2,
monomer (b2):
a compound represented by CH2═CR3-G2-(C2H4O)q2—(C4H8O)q3—R4, wherein each of R1, R2, R3 and R4 which are independent of one another, is a hydrogen atom or a methyl group, each of q1 and q3 which are independent of each other, is an integer of from 1 to 50, q2 is an integer of from 1 to 50, each of G1 and G2 which are independent of each other, is
—COO(CH2)r— or —COO(CH2)t—NHCOO— wherein r is an integer of from 0 to 4, and t is an integer of from 1 to 4.

4 more elements

A method for producing an antifouling composition, which comprises polymerizing a monomer mixture comprising from 30 to 65 mass % of the following monomer (a), from 1 to 67 mass % of the following monomer (b1) and from 3 to 34 mass % of the following monomer (b2), wherein the content of —(C2H4O)— is from 20 to 65 mass %, and the content of —(C4H8O)— is from 2 to 13 mass %, in the presence of a polymerization initiator in a medium:

monomer (a):
a compound represented by (Z—Y)nX, wherein Z is a C1-6 perfluoroalkyl group or a monovalent group represented by CmF2m+1O(CFWCF2O)dCFK— wherein m is an integer of from 1 to 6, d is an integer of from 0 to 4, and each of W and K which are independent of each other, is a fluorine atom or a trifluoromethyl group, Y is a bivalent organic group or a single bond, n is 1 or 2, when n is 1, X is —CR═CH2, —COOCR═CH2,—OCOCR═CH2, —OCH2-φ-CR═CH2 or —OCH═CH2, and when n is 2, X is —CH[—(CH2)pCR═CH2]—, —CH[—(CH2)pCOOCR═CH2]—, —CH[—CH2)pOCOCR═CH2]— or —OCOCH═CHCOO—, R is a hydrogen atom, a methyl group or a halogen atom, φ is a phenylene group, and p is an integer of from 0 to 4,
monomer (b1):
a compound represented by CH2═CR1-G1-(C2H4O)q1—R2,
monomer (b2):
a compound represented by CH2═CR3-G2-(C2H4O)q2—(C4H8O)q3—R4,
wherein each of R1, R2, R3 and R4 which are independent of one another, is a hydrogen atom or a methyl group, each of q1 and q3 which are independent of each other, is an integer of from 1 to 50, q2 is an integer of from 1 to 50, each of G1 and G2 which are independent of each other, is
—COO(CH2)r— or —COO(CH2)t—NHCOO— wherein r is an integer of from 0 to 4, and t is an integer of from 1 to 4.

5 more elements

Dependencies are inferred from the claim text.

Description9,927 words

Summary999 words

#The present invention relates to an antifouling composition, a method for its production and an article treated with the antifouling composition.

#Heretofore, as treating agents for water/oil repellent treatment or antifouling treatment of clothing, various compositions have been provided depending upon the particular purposes. For work wears such as work clothes, linen such as rental sheets, etc., it has been common to employ a fluorine type SR (soil release) agent which has both water/oil repellency to prevent soiling and SR (soil release) properties whereby any soil attached may readily be removed by cleaning or washing.

#For example, there have been proposed a fluorine type antifouling agent containing, as an effective component, a copolymer of a (meth)acrylate containing a polyfluoroalkyl group, a (meth)acrylate containing a polyoxyalkylene chain and a (meth)acrylate containing a blocked isocyanate group (the following Patent Document 1), a fluorine type antifouling agent containing, as an effective component, a copolymer of a (meth)acrylate containing a polyfluoroalkyl group, a (meth)acrylate containing a polyoxyalkylene chain and a (meth)acrylate containing an acetoacetyl group (the following Patent Document 2), etc.

Detailed description8,928 words

#The fluorocopolymer contained in the antifouling composition of the present invention comprises at least polymerized units (a) based on the monomer (a), polymerized units (b1) based on the monomer (b1) and polymerized units (b2) based on the monomer (b2). Further, it may contain polymerized units (c) based on the monomer (c) and/or polymerized units (d) based on the monomer (d).

#<Monomer (a)>

#The polymerized units (a) are polymerized units formed by cleavage of a double bond in a polymerizable unsaturated group in the monomer (a).

Facts

Application

12/622,949Filed 20 Nov 2009 · continuation

Priority

JP 2007-13541222 May 2007

Published

US 2010/0069565 A118 Mar 2010

Granted

15 Oct 2013

Term ends

6 May 2029

Estimated · how

20 years from earliest known nonprovisional domestic filing plus recorded patent term adjustment, including 350 days of adjustment. Maintenance-fee lapses, terminal disclaimers and statutory extensions have not been checked. The continuity chain may be incomplete; this is not an enforceability determination.

Classification7 codes

D06M 15/277
Of unsaturated carboxylic acids; Salts or esters thereof: containing fluorine
C08F 220/24
Esters containing halogen: containing perhaloalkyl radicals
C08F 220/282
Containing no aromatic rings in the alcohol moiety: and containing two or more oxygen atoms
D06M 2200/11
Repellency against liquids: oleophobic properties

Timeline

22 May 2007Priority claimedJP 2007-135412
20 Nov 2009Application filedUS 12/622,949
20 Nov 2009Assigned to Asahi Glass Company, Limitedassignment of assignor's interest
18 Mar 2010PublishedUS 2010/0069565 A1
9 Nov 2011Assigned to Asahi Glass Company, Limitedcorporate address change
15 Oct 2013GrantedUS 8,557,939 B2
7 Aug 2018Assigned to Agc Inc.change of name
12 Oct 2026TodayWithin its term
6 May 2029Term endsEstimated, includes 350 days of adjustment

Antifouling composition, method for its production and article treated therewith

Life of this patent

Antifouling composition, method for its production and article treated therewith

Life of this patent

Life of this patent

Abstract

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Claims19

Description9,927 words

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Classification7 codes

Life of this patent

Description9,927 words