Water and oil repellent compositon

Details Water and oil repellent compositon Water and oil repellent compositon

1998-07-23

2001-01-23

Lipman, Bernard (Department: 1713)

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

Synthetic resins

Polymers from only ethylenic monomers or processes of...

C526S319000, C525S124000, C524S589000, C528S070000, C528S075000, C428S423100, C427S372200, C427S285000

Reexamination Certificate

active

06177531

ABSTRACT:

WATER AND OIL REPELLENT COMPOSITION
The present invention relates to an water and oil repellent composition excellent in durability of water and oil repellency and durability of water resistance.
In recent years, treatment of clothings, etc., for water and oil repellency and for water resistance has been common, and various compositions containing copolymers having polyfluoroalkyl groups have been proposed depending upon the particular purposes. (In this specification, a polyfluoroalkyl group will be hereinafter referred to as “a R
f
group”. Further, an acrylate and/or a methacrylate will be referred to as “a (meth)acrylate”. The same applies to other alkyl (meth)acrylates.)
For example, for sports and outdoor clothings, a high level of durability of water and oil repellency and water resistance against washing, dry cleaning, abrasion, etc., is required, and as a copolymer component to impart such durability, a copolymer of a (meth)acrylate having a R
f
group, a (meth)acrylate having a blocked isocyanate group arid a (meth)acrylate having a polyoxyalkylene chain, has been proposed (JP-A-6-279687).
Further, a copolymer of an acrylate having a R
f
group with vinyl chloride (JP-B-50-3438), a polymer of an acrylate having both a R
f
group and an aromatic blocked isocyanate group (JP-A-3-8873) or a copolymer of a (meth)acrylate having a R
f
group with a (meth)acrylate having an alicyclic or heterocyclic polyisocyanate group having a blocked isocyanate group (JP-A-6-240239) has been proposed.
Further, it has been proposed to copolymerize, as a crosslinking component to improve the durability, N-methylol acrylamide (JP-B-39-2350) or glycidyl methacrylate (JP-A-4-68006).
However, conventional compositions all had a drawback that no adequate durability against washing was obtainable. A copolymer containing polymeric units of a methacrylate having a polyoxyalkylene group, had a drawback that no adequate water repellency or water resistance was obtained. Further, in order to improve the durability, a method has also been known wherein a compound having a R
f
group and a melamine resin or a compound having a blocked isocyanate group, are used in combination for treatment of fibers. In this case, however, there has been yellowing of the cloth or hardening of the texture. Further, a method for improving water resistance by coating a polyurethane resin or an acrylic resin, has also been known. However, in this case, there is a drawback that the texture tends to be hard.
It is an object of the present invention to provide a water and oil repellent composition which is capable of imparting durable water and oil repellency and water resistance and which is free from a problem such as yellowing or hardening of the texture of a cloth.
The present invention provides a water and oil repellent composition containing, as an effective component, a copolymer comprising the following polymeric units (a), (b) and at least one member selected from (c) and (d):
polymeric units (a): Polymeric units of a (meth)acrylate having a polyfluoroalkyl group;
Polymeric units (b): Polymeric units of 2-isocyanate ethyl (meth)acrylate with the isocyanate group blocked;
Polymeric units (c): Polymeric units of vinyl chloride; and
Polymeric units (d): Polymeric units of an alkyl (meth)acrylate.
Now, the present invention will be described in detail with reference to the preferred embodiments.
The polymeric units (a) are polymeric units of a (meth)acrylate having a R
f
group. The (meth)acrylate having a R
f
group is meant for a group wherein a R
f
group is present in the 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, the R
f
group is preferably a straight chain or branched group. When it is a branched group, it is preferred that the branched moiety is present at the terminal portion of the R
f
group, and it is of a short chain having from 1 to 4 carbon atoms. 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%, particularly preferably at least 80%, when represented by [(number of fluorine atoms in the R
f
group)/(number of hydrogen atoms contained in the corresponding alkyl group having the same carbon number)]×100(%). Further, the R
f
group is preferably a group having all of the hydrogen atoms of the alkyl group substituted by fluorine atoms (i.e. a perfluoroalkyl group), or a group having a perfluoroalkyl group at a terminal portion.
The carbon number of the perfluoroalkyl group is preferably from 2 to 20, particularly preferably from 6 to 16. If the carbon number is less than 6, the water repellency and the oil repellency of the water and oil repellent composition tend to decrease, and if it exceeds 16, the copolymer tends to be solid at room temperature, and the sublimation property tends to increase whereby the handling tends to be difficult.
As the (meth)acrylate having a R
f
group, a compound of the following formula (1) is preferred.
R
f
—Q—OCOCR═CH
2
  (1)
In the formula (1), R
f
represents the R
f
group, Q is a bivalent organic group, and R is a hydrogen atom or a methyl group. The R
f
group is preferably those disclosed in the following specific examples and in Examples.
Q may, for example, be preferably —(CH
2
)
p+q
—, —(CH
2
)
p
CONH(CH
2
)
q
—, —(CH
2
)
p
OCONH(CH
2
)
q
—, —(CH
2
)
p
SO
2
NR′(CH
2
)
q
—, —(CH
2
)
p
NHCONH(CH
2
)
q
—, or —(CH
2
)
p
—CH(OH)—(CH
2
)
q
—, provided R′ is a hydrogen atom or an alkyl group. Further, each of p and q which are independent of each other, is an integer of at least 0, and p+q is an integer of from 1 to 22. Preferred is the one wherein Q is —(CH
2
)
p+q
—, —(CH
2
)
p
CONH(CH
2
)
q
— or —(CH
2
)
p
SO
2
NR′ (CH
2
)
q
—, and q is an integer of at least 2, and p+q is from 2 to 6. Particularly preferred is the one wherein Q is —(CH
2
)
p+q
— where p+q is from 2 to 6, i.e. from an ethylene group to a hexamethylene group. Further, it is preferred that a fluorine atom is bonded to the carbon atom of R
f
bonding to Q.
Now, specific examples of the (meth)acrylate having a R
f
group will be given below, wherein R is a hydrogen atom or a methyl group.
CF
3
(CF
2
)
4
CH
2
OCOCR═CH
2
,
CF
3
(CF
2
)
5
CH
2
CH
2
OCOCR═CH
2
,
H(CF
2
)
6
CH
2
CH
2
OCOCR═CH
2
,
CF
3
(CF
2
)
7
CH
2
CH
2
OCOCR═CH
2
,
(CF
3
)
2
CF(CF
2
)
5
CH
2
CH
2
OCOCR═CH
2
,
CF
3
(CF
2
)
7
SO
2
N(C
3
H
7
)CH
2
CH
2
OCOCR═CH
2
,
CF
3
(CF
2
)
7
(CH
2
)
4
OCOCR═CH
2
,
CF
3
(CF
2
)
7
SO
2
N(CH
3
)CH
2
CH
2
OCOCR═CH
2
,
CF
3
(CF
2
)
7
SO
2
N(C
2
H
5
)CH
2
CH
2
OCOCR═CH
2
,
CF
3
(CF
2
)
7
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
,
CF
3
(CF
2
)
8
CH
2
OCOCR═CH
2
,
CF
3
(CF
2
)
8
CONHCH
2
CH
2
OCOCR═CH
2
,
CF
3
(CF
2
)
7
CH
2
CH(OH)CH
2
CH
2
OCOCR═CH
2
.
The copolymer of the present invention may contain one or more types of polymeric units (a). When it contains two or more different types of polymeric units (a), it is preferably a mixture of (meth)acrylates having R
f
groups with different carbon numbers.
The polymeric units (b) are polymeric units of 2-isocyanate ethyl (meth)acrylate wherein the isocyanate group is blocked. It has been unexpectedly found that by the presence of the polymeric units of 2-isocyanate ethyl methacrylate wherein the isocyanate group is blocked, not only the durability of water and oil repellency against natural fibers such as cotton, is remarkably improved, but also durability of water and oil repellency against a substrate having no functional

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