Antifouling composition, method for its production and...

Details Antifouling composition, method for its production and... Antifouling composition, method for its production and...

1998-06-29

2001-03-27

Morris, Terrel (Department: 1771)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Polymers from only ethylenic monomers or processes of...

C526S246000, C526S301000

Reexamination Certificate

active

06207777

ABSTRACT:

The present invention relates to an antifouling composition excellent in durability of the antifouling property and color fastness.
It has been common to apply a composition having a fluorine moiety and a hydrophilic moiety to clothings which are susceptible to fouling, such as working wears. Such treatment is intended to impart water and oil repellency to fibers and to impart a nature (hereinafter referred to as an antifouling property) whereby deposition of soil is prevented or any soil attached may readily be removed by washing. The following substances are known as an effective component of the composition used for such treatment. (In this specification, “R
f
” group” means a polyfluoroalkyl group, and “(meth)acrylate” means acrylate and/or methacrylate, and the same applies to a representation such as “(meth)acrylamide”.)
(1) A copolymer of a polymerizable compound having a R
f
group, a (meth)acrylate having a polyoxyethylene group and acrylonitrile (JP-A-50-20991).
(2) A compound obtained by reacting an isocyanate compound having at least two functional groups, a compound having both a R
f
group and an isocyanate reactive group, a compound having both an epoxy group and an isocyanate reactive group, and a compound having both a hydrophilic group and an isocyanate reactive group (JP-A-61-23674).
(3) A copolymer of a (meth)acrylate having a R
f
group, a polyalkylene glycol (meth)acrylate, a (meth)acrylate having a hydroxyl group, and an alkyl (meth)acrylate or butadiene (JP-A-3-103411).
(4) A copolymer of a (meth)acrylate having a R
f
group, a (meth)acrylate having a polyoxyalkylene group, and a (meth)acrylate having an epoxy group (JP-A-4-68006).
(5) A copolymer of a (meth)acrylate having a R
f
group, a (meth)acrylate having a polyoxyalkylene group, 3-chloro-2-hydroxypropyl (meth)acrylate and glycerol mono(meth)acrylate (JP-A-6-116340).
(6) A copolymer of a (meth)acrylate having a R
f
group, a (meth)acrylate having a polyoxyalkylene group, and a (meth)acrylate having a blocked isocyanate group (JP-A-6-279687).
The conventional compositions all had a drawback such that the antifouling properties of the treated fibers tended to decrease by washing. To prevent such a decrease of the antifouling properties, a method has been proposed to use these compositions in combination with a melamine resin or a compound having a blocked isocyanate group at the time of treatment of the fibers. However, in such a case, the cloth is likely to undergo yellowing, or its texture tends to be hard. Further, the copolymer as an effective component, contains a large amount of hydrophilic moieties, whereby there has been a drawback that the color fastness is poor, and application of such a method is difficult particularly to e.g. deep colored fiber materials.
It is an object of the present invention to provide an antifouling composition which is capable of imparting a durable antifouling property without a problem such as yellowing of the cloth or hardening of the texture and which provides excellent color fastness.
The present inventors have found that a product treated with an antifouling composition comprising a certain specific copolymer, has excellent durability with respect to the antifouling property and at the same time, exhibits excellent color fastness.
Namely, the present invention provides an antifouling composition comprising, as an effective component, a copolymer comprising the following polymer units (a), (b), (c) and (d):
(a) polymer units of a (meth)acrylate having a polyfluoroalkyl group,
(b) polymer units of a (meth)acrylate having a polyoxyethylene group,
(c) polymer units of a (meth)acrylate having a polyoxypropylene group, and
(d) polymer units of a (meth)acrylate having a blocked isocyanate group.
Now, the present invention will be described in detail with reference to the preferred embodiments.
The polymer units (a) are polymer units of a (meth)acrylate having a R
f
group. The (meth)acrylate having a R
f
group is meant for a compound having a R
f
group at an alcohol residue of the (meth)acrylate.
The R
f
group is meant for a group having at least two hydrogen atoms of an alkyl group substituted by fluorine atoms. The carbon number of the R
f
group is preferably from 2 to 20, particularly preferably from 6 to 16. Further, as the R
f
group, a linear or branched group is preferred. In the case of a branched group, it is preferred that the branched moiety is present at a terminal portion of the R
f
group, and it is a short chain having a carbon number of from about 1 to 4. The R
f
group may contain halogen atoms other than fluorine atoms. As such other halogen atoms, chlorine atoms are preferred. Further, a carbon atom in the R
f
group may be substituted by an etheric oxygen atom.
The number of fluorine atoms in the R
f
group is preferably at least 60%, more preferably at least 80%, as represented by [(the number of fluorine atoms in the R
f
group)/(the number of hydrogen atoms contained in an alkyl group having the same carbon number as the R
f
group)]×100 (%). Further, the R
f
group is preferably a group having all of hydrogen atoms of an alkyl group substituted by fluorine atoms (i.e. a perfluoroalkyl group), or a group having a perfluoroalkyl group at its terminal portion.
The carbon number of the perfluoroalkyl group is preferably from 2 to 20, more preferably from 6 to 16. If the carbon number is less than 6, the water repellency and oil repellency of the antifouling composition tend to decrease. On the other hand, if it exceeds 16, the copolymer tends to be solid at room temperature, and tends to readily sublime, whereby its handling tends to be difficult.
The (meth)acrylate having a R
f
group is preferably a compound represented by the following formula 1. In the formula 1, R
f
represents a R
f
group, Q represents a bivalent organic group, and R is a hydrogen atom or a methyl group. As the R
f
group, those disclosed in the following specific examples and Examples are preferred.
R
f
—Q—OCOCR═CH
2
  (1)
Q may, for example, be —(CH
2
)
p+q
—, an alkylene group having a branch, —(CH
2
)
p
CONH(CH
2
)
q
—, —(CH
2
)
p
NHCO(CH
2
)
q
—, —(CH
2
)
p
OCONH(CH
2
)
q
—, —(CH
2
)
p
NHOCO (CH
2
)
q
—, —(CH
2
)
p
SO
2
NR′(CH
2
)
q
—, —(CH
2
)
p
NR′SO
2
(CH
2
)
q
—, —(CH
2
)
p
NHCONH(CH
2
)
q
—, or —(CH
2
)
p
CH(OH)(CH
2
)
q
—, wherein R′ is a hydrogen atom or an alkyl group, and each of p and q is an integer of at least 0, provided that p+q is an integer of from 1 to 22.
It is preferred that Q is —(CH
2
)
p+q
—, —(CH
2
)
p
CONH(CH
2
)
q
— or —(CH
2
)
p
SO
2
NR′ (CH
2
)
q
—, wherein q is an integer of at least 2, and p+q is from 2 to 6. Particularly preferred is —(CH
2
)
p+q
—, wherein p+q is from 2 to 6, i.e. from an ethylene group to a hexamethylene group. It is preferred that fluorine atoms are bonded to the carbon atom of R
f
bonded to Q.
The alkylene group having a branch may, for example, be preferably —CH
2
CH(CH
3
)—, —CH(CH
3
)CH
2
—, —CH
2
CH(CH
3
)CH
2
—, —CH
2
CH
2
CH(CH
3
)—, —CH(CH
3
)CH
2
CH
2
—, —CH
2
CH
2
CH(CH
3
CH
2
—, or —CH
2
CH(CH
3
)CH
2
CH
2
—, particularly preferably —CH
2
CH
2
CH(CH
3
)—.
Specific examples of the (meth)acrylate having a R
f
group will be given below. In these examples, R represents a hydrogen atom or a methyl group.
F(CF
2
)
5
CH
2
OCOCR═CH
2
.
F(CF
2
)
6
CH
2
CH
2
OCOCR═CH
2
.
H(CF
2
)
6
CH
2
CH
2
OCOCR═CH
2
.
F(CF
2
)
8
CH
2
CH
2
OCOCR═CH
2
.
(CF
3
)
2
CF(CF
2
)
5
CH
2
CH
2
OCOCR═CH
2
.
F(CF
2
)
8
SO
2
N(C
3
H
7
)CH
2
CH
2
OCOCR═CH
2
.
F(CF
2
)
8
CH
2
CH
2
CH
2
OCOCR═CH
2
.
F(CF
2
)
8
(CH
2
)
4
OCOCR═CH
2
.
F(CF
2
)
8
CH
2
CH
2
CH(CH
3
)OCOCR═CH
2
.
F(CF
2
)
8
SO
2
N(CH
3
)CH
2
CH
2
OCOCR═CH
2
.
F(CF
2
)
8
SO
2
N(C
2
H
5
)CH
2
CH
2
OCOCR═CH
2
.
F(CF
2
)
8
CONHCH
2
CH
2
OCOCR═CH
2
.
(CF
3
)
2
CF(CF
2
)
5
(CH
2
)
3
OCOCR═CH
2
.
(CF
3
)
2
CF(CF
2
)
5
CH
2
CH(OCOCH
3
)—OCOCR═CH
2
.
(CF
3
)
2
CF(CF
2
)
5
CH
2
CH(OH)CH
2
OCOCR═CH
2
.
F(CF
2
)
9
CH
2
CH
2
OCOCR&bo

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