Polymer and antifouling agent composition containing the same

Details Polymer and antifouling agent composition containing the same Polymer and antifouling agent composition containing the same

2000-01-19

2002-03-12

Cain, Edward J. (Department: 1714)

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

Synthetic resins

Polymers from only ethylenic monomers or processes of...

C526S292400, C526S292600, C526S292700

Reexamination Certificate

active

06355753

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to a novel polymer and a stainproofing agent composition comprising the same. More particularly, the present invention relates to a polymer having a reactive group and a fluoroalkyl group, and a stainproofing agent composition containing the same, which has durability. The stainproofing agent composition of the present invention is particularly useful for a carpet.
RELATED ART
In order to impart the water repellency, oil repellency and stainproof properties to textiles (e.g. carpet), various stainproofing agents have hitherto been suggested. U.S. Pat. Nos. 4,925,906, 5,015,259 and 5,223,340 each discloses that a stainproofing agent composition comprising a copolymer containing carboxylic acid imparts the water repellency, oil repellency and stainproof properties. However, according to these copolymers, the water repellency and oil repellency after cleaning are maintained, but the stainproof properties are insufficient.
SUMMARY OF THE INVENTION
An object of the present invention is to provide a polymer imparting durability capable of maintaining sufficient water- and oil-repellency and stainproof properties before and after cleaning.
The present invention provides a stainproofing polymer having:
(i) a reactive group selected from the group consisting of a carboxyl group or its salt, a hydroxyl group, an epoxy group, a phosphoric acid group, an alkoxysilane group, an imine group, a sulfonic acid group, an amino group, an isocyanate group and a blocked isocyanate group; and
(ii) a fluoroalkyl group, characterized in that:
a melting point of a monomer having a fluoroalkyl group, which constitutes the polymer, is at least 70° C. and a melting point of the stainproofing polymer is at least 50° C.
In the present description, this stainproofing polymer is referred to as a polymer (A).
The melting point of the monomer having a fluoroalkyl group is at least 70° C., and preferably at least 80° C. The melting point of the polymer (A) is at least 50° C., and preferably at least 70° C., e.g. at least 80° C.
The amount of the reactive group may be from 0.01 to 30% by weight, e.g. 0.1 to 20% by weight, based on the weight of the polymer (A). The amount of the fluoroalkyl group may be from 30 to 90% by weight, e.g. 40 to 80% by weight, based on the weight of the polymer (A).
The polymer (A) may be a copolymer obtained by copolymerization of:
(i) a monomer having a reactive group selected from the group consisting of a carboxyl group, a carboxylic anhydride group, a hydroxyl group, an epoxy group, a phosphoric acid group, an alkoxysilane group, an imine group, a sulfonic acid group, an amino group, an isocyanate group or a blocked isocyanate group, and a chlorine atom, and a carbon-carbon double bond; and
(ii) a monomer having a fluoroalkyl group and a carbon-carbon double bond.
Alternatively, the polymer (A) may be a homopolymer or copolymer obtained by polymerization of a monomer having:
(a) a reactive group selected from the group consisting of a carboxyl group, a carboxylic anhydride group, a hydroxyl group, an epoxy group, a phosphoric acid group, an alkoxysilane group, an imine group, a sulfonic acid group, an amino group, an isocyanate group or a blocked isocyanate group, and a chlorine atom;
(b) a fluoroalkyl group; and
(c) a carbon-carbon double bond.
The monomer constituting the polymer (A) is preferably fluorine-containing maleate or fluorine-containing fumarate.
The fluorine-containing maleate and fluorine-containing fumarate include the followings:
wherein Rf is a perfluoroalkyl group having 3 to 21 carbon atoms.
Alternatively, the monomer constituting the polymer (A) may be a compound represented by the general formula:
CH
2
═CZ
1
—CO—O—Z
2
  (XI)
wherein Z
1
is a hydrogen atom, an alkyl group or a —CH
2
COOH group; Z
2
is a hydrogen atom, —Z
3
—X
1
(with the proviso that Z
3
is a direct bond or an alkylene group; and X
1
is a carboxyl group, a hydroxyl group, an epoxy group, a phosphoric acid group, an alkoxysilane group, or a residue wherein one hydrogen is removed from one carboxyl group of dicarboxylic acid) or —CH
2
—C(OZ
4
)H—CH
2
—Cl (Z
4
is a hydrogen atom or an acyl group); and Z
1
and Z
2
may be combined each other to form carboxylic anhydride. For example, the monomer (XI) constituting the polymer (A) may be a (meth)acrylate compound.
Specific examples of the monomer (XI) are as follows.
(trade name: Light Ester HO-MS (manufactured by Kyoei-Sha Chemical Co., Ltd.))
(trade name: Light Ester HO-HH (manufactured by Kyoei-Sha Chemical Co., Ltd.))
(trade name: Light Ester HOA-MS (manufactured by Kyoei-Sha Chemical Co., Ltd.))
(trade name: Light Ester HOA-MPL (manufactured by Kyoei-Sha Chemical Co., Ltd.))
(trade name: Light Ester PM (manufactured by Kyoei-Sha Chemical Co., Ltd.))
(trade name: Light Ester PA (manufactured by Kyoei-Sha Chemical Co., Ltd.))
(trade name: Light Ester G (manufactured by Kyoei-Sha Chemical Co., Ltd.))
(trade name: Light Ester CL (manufactured by Kyoei-Sha Chemical Co., Ltd.))
(trade name: SZ6030 (manufactured by Toray Dow Corning Silicone Co., Ltd.))
(n=1 to 20) (sulfonic acid-group containing monomer)
(Isocyanate Group-containing Monomer)
The monomer (XI) having a reactive group is copolymerized with a monomer (XII) having a fluoroalkyl group to obtain the polymer (A) of the present invention.
In the polymer (A), the amount of the monomer (XI) may be from 0.01 to 30% by weight, e.g. 0.1 to 20% by weight, based on the weight of the copolymer (A), while the amount of the monomer (XII) may be from 30 to 90% by weight, e.g. from 40 to 80% by weight, based on the weight of the copolymer (A).
The fluoroalkyl group in the monomer (XII) having the fluoroalkyl group may be a perfluoroalkyl group. The monomer (XII) may be a (meth)acrylate containing a fluoroalkyl group having 3 to 21 carbon atoms. The monomer (XII) maybe a compound represented by the general formula:
Rf—R
1
—OCOC(R
2
)═CH
2
wherein Rf is a straight-chain or branched fluoroalkyl group having 3 to 20 carbon atoms; R
1
is a straight-chain or branched alkylene group having 1 to 20 carbon atoms, a —CON(R
3
)—R
4
— group, a —SO
2
N(R
3
)R
4
— group or a —CH
2
CH(OR
5
)—CH
2
— group (with the proviso that R
3
is an alkyl group having 1 to 10 carbon atoms, R
4
is a straight-chain or branched alkylene group having 1 to 10 carbon atoms, and R
5
is a hydrogen atom or an acyl group having 1 to 10 carbon atoms); and R
2
is a hydrogen atom or a methyl group.
Examples of the monomer (XII) having a fluoroalkyl group are as follows:
CF
3
(CF
2
)
4
CH
2
═OCOC(CH
3
)═CH
2
CF
3
(CF
2
)
7
(CH
2
)
2
OCOC(CH
3
)═CH
2
CF
3
(CF
2
)
7
(CH
2
)
2
OCOCH═CH
2
(CF
3
)
2
CF(CF
2
)
4
(CH
2
)
2
OCOCH═CH
2
CF
3
(CF
2
)
7
SO
2
N(C
3
H
7
)(CH
2
)
2
OCOCH═CH
2
CF
3
(CF
2
)
7
SO
2
N(C
3
)(CH
2
)
2
OCOC(CH
3
)═CH
2
CF
3
(CF
2
)
7
SO
2
N(C
2
H
5
)(CH
2
)
2
OCOCH═CH
3
CF
3
(CF
2
)
7
CONH(CH
2
)
2
OCOCH═CH
2
(CF
3
)
2
CF(CF
2
)
6
(CH
2
)
3
OCOCH═CH
2
(CF
3
)
2
CF(CF
2
)
6
CH
2
CH(OCOCH
3
)CH
2
OCOC(CH
3
)═CH
2
(CF
3
)
2
CF(CF
2
)
6
CH
2
CH(OH)CH
2
OCOCH═CH
2
CF
3
(CF
2
)
9
(CH
2
)
2
OCOCH═CH
2
CF
3
(CF
2
)
9
(CH
2
)
2
OCOC(CH
3
)═CH
2
CF
3
(CF
2
)
9
CONH(CH
2
)
2
OCOC(CH
3
)═CH
2
The polymer (A) may have an adherent group capable of accelerating adhesion of the polymer to the substrate to be treated. The adherent group includes, for example, a chlorine atom, a urethane group, an amide group and an ester group. The adherent group can be introduced into the polymer (A) by polymerizing the monomer having the adherent group. In the polymer (A), a monomer having a reactive group, a fluoroalkyl group and an adherent group may be used.
Specific examples of the monomer having an adherent group include the followings: vinyl chloride,
The amount of the adherent group may be from 0.1 to 50% by weight based on the weight of the polymer (A).
The stainproofing agent composition of the present invention comprises the polymer (A) and other polymer (B).
The

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