Copolymer and stainproofing agent containing the same

Details Copolymer and stainproofing agent containing the same Copolymer and stainproofing agent containing the same

1998-01-29

2001-09-04

Wu, David W. (Department: 1713)

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

Synthetic resins

Polymers from only ethylenic monomers or processes of...

C526S309000, C526S310000, C526S248000, C524S805000, C428S395000

Reexamination Certificate

active

06284853

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to a copolymer, a composition containing the copolymer, and a stainproofing agent containing the copolymer as an active component.
RELATED ART
In order to impart the water repellency, oil repellency and stainproofing properties to a textile (e.g. carpet), various stainproofing agents have hitherto been suggested. Japanese Patent Kokoku Publication Nos. 17109/1988, 55515/1991 and 55516/1991 disclose that a stainproofing agent comprising a urethane compound and a specific copolymer blend imparts the water repellency, oil repellency and stainproofing properties. However, the water repellency, oil repellency and stainproofing properties after cleaning are insufficient when using these copolymers.
U.S. Patent No. 5,149,754 discloses a stainproofing agent composition containing a monomer having a carboxyl group or a carboxylic anhydride group. However, this composition can not impart sufficient water repellency and oil repellency after cleaning.
As described above, various water- and oil-repellents have hitherto been suggested, but those where sufficient water repellency, oil repellency and stainproofing properties are maintained before and after cleaning are yet to be obtained.
SUMMARY OF THE INVENTION
An object of the present invention is to provide a copolymer which imparts good durability on cleaning while maintaining good water- and oil-repellency.
The present invention provides a copolymer (A) having:
(i) a fluoroalkyl group,
(ii) a urethane or urea linkage, and
(iii) a functional group selected from the group consisting of a carboxyl group, a carboxylic anhydride group, an epoxy group, a phosphoric group, an alkoxysilane group, an imine group, a sulfonic group, an amino group, an isocyanate group and a chlorine atom.
The present invention also provides a composition (B) comprising the above copolymer (A) and an acrylic copolymer containing no fluorine.
The present invention also provides a stainproofing agent comprising:
(a) (i) the copolymer (A) alone, or (ii) a mixture of the copolymer (A) and the copolymer (B), and
(b) a solvent.
DETAILED DESCRIPTION OF THE INVENTION
The copolymer (A) of the present invention can be obtained by copolymerizing:
(I) a monomer which has a fluoroalkyl group and optionally has a urethane or urea linkage,
(II) a monomer which contains no fluorine and has at least one urethane or urea linkage and one carbon-carbon double bond, and
(III) a monomer which has a functional group selected from the group consisting of a carboxyl group, a carboxylic anhydride group, an epoxy group, a phosphoric group, an alkoxysilane group, an imine group, a sulfonic group, an amino group, an isocyanate group and a blocked adduct thereof and a chlorine atom and has a carbon-carbon double bond.
The monomer (I) and monomer (II) may be a single monomer having (a) a fluoroalkyl group, (b) a urethane or urea linkage and (c) a carbon-carbon double bond.
The fluoroalkyl group in the monomer (I) is preferably a perfluoroalkyl group.
The monomer (I) having a fluoroalkyl group may be a (meth)acrylate ester having a C
3-21
fluoroalkyl group. The monomer (I) may be a compound represented by the general formula:
Rf—R
1
—OCOC(R
2
)═CH
2
wherein Rf is a linear or branched fluoroalkyl group having 3 to 20 carbon atoms;
R
1
is a linear or branched alkylene group having 1 to 20 carbon atoms, a group of —CON(R
3
)—R
4
—, a group of —SO
2
N(R
3
)R
4
— or a group of —CH
2
CH(OR
5
)CH
2
— (R
3
is an alkyl group having 1 to 10 carbon atoms; R
4
is a linear 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 (I) 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(CH
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
(F
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 monomer (I) having a urethane or urea linkage and a fluoroalkyl group may be represented by the general formula:
Rf
1
—X
1
—A
1
—CONH—Y
1
—NHCO—A
2
—O—C(═O)—CR
2
═CH
2
wherein Rf
1
is a fluoroalkyl group having 4 to 16 carbon atoms; X
1
is —R
6
—, —CON(R
3
)—R
4
— or —SO
2
N(R
3
)—R
4
—[R
6
is an alkylene (for example, C
1
to C
30
) group; R
3
is a hydrogen atom or a lower (for example, C
1
to C
10
) alkyl group; R
4
is an alkylene (for example, C
1
to C
30
) group]; A
1
is —O—, —S— or —N(R
3
)—[R
3
is a hydrogen atom or a lower (for example, C
1
to C
10
) alkyl group]; Y
1
is a residue wherein isocyanate is removed from an aromatic or alicyclic diisocyanate; A
2
is a divalent organic group capable of having 2 to 9 carbon atoms and at least one oxygen atom; and R
2
is a hydrogen atom or a methyl group.
Specific examples of the monomer (I) having a urethane or urea linkage and a fluoroalkyl group are as follows.
The monomer (II) which contains no fluorine and has at least one urethane or urea linkage and one carbon-carbon double bond may be obtained by reacting:
(A) a compound having at least two isocyanate groups,
(B) a compound having one carbon-carbon double bond and at least one hydroxyl or amino group, and
(C) a compound having one hydroxyl or amino group.
Examples of the compound (A) are as follows.
The compound (A) is preferably a diisocyanate. However, a triisocyanate and a polyisocyanate having at least four isocyanate groups can also be used in the reaction.
For example, a trimer of the diisocyanate, polymeric MDI (diphenylmethane diisocyanate) and an adduct between a polyhydric alcohol (e.g. trimethylolpropane, trimethylolopropane and glycerin) and a diisocyanate can also be used in the reaction.
Examples of the triisocyanate and polyisocyanate are as follows.
The compound (B) may be, for example, a compound represented by the formula:
wherein R
2
is a hydrogen atom or a methyl group; p is from 0 to 300; and X is as follows.
wherein p, m and n each is an integer of 1 to 300.
The compound (C) may be a compound represented by the formula:
R
7
—OH
R
7
—NH
2
or
R
7
—NH—R
8
wherein R
7
and R
8
are the same or different and each is a C
1
-C
22
alkyl group, which may contains a hetero atom, and an aromatic or alicyclic group. Preferable groups for R
7
and R
8
include C
8
H
17
, C
17
H
35
, C
3
H
9
and cyclohexyl.
Examples of the compound (C) are butyl alcohol, 2-ethylhexyl alcohol, lauryl alcohol, stearyl alcohol, oleyl alcohol, benzyl alcohol, cyclohexyl alcohol, 2-ethylhexylamine and stearylamine.
When the compound (A) is a diisocyanate, the monomer (II) can be obtained by reacting 1 mol of the compound (B) and 1 mol of the compound (C) with 1 mol of the compound (A). When the compound (A) is a triisocyanate, the monomer (II) can be obtained by reacting 1 mol of the compound (B) and 2 mol of the compound (C) with 1 mol of the compound (A).
Both structure units (I) and (II) may be derived from a single monomer, not two monomers.
The monomer constituting the structure unit (III)
5
may be vinyl chloride (CH
2
═CHCl) or a compound represented by the general formula:
CH
2
═CA
3
—CO—O—A
4
wherein A
3
is a hydrogen atom, an alkyl (for example, C
1
-C
10
)group or a group of —CH
2
COOH; and A
4
is a hydrogen atom, —A
5
—X
2
(A
5
is a direct bond or an alkylene (for example, C
1
-C
30
) group; and X
2
is a carboxyl group, an epoxy group, a phosphoric group, an alkoxysilane group, an amino group or a residue wherein one hydrogen is removed from one carboxyl grou

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