Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – At least one aryl ring which is part of a fused or bridged...
Reexamination Certificate
1999-11-04
2001-06-26
Michl, Paul R. (Department: 1714)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
At least one aryl ring which is part of a fused or bridged...
C524S200000
Reexamination Certificate
active
06251984
ABSTRACT:
The present invention relates to an aqueous dispersion type antisoiling composition suitable for water and oil repellency treatment or antisoiling treatment of carpets or cloths for upholstery.
For the purpose of imparting an antisoiling property to fibers, it is widely practiced to treat the fibers with a fluorine-type water and oil repellant. However, carpets and cloths for upholstery are required to have not only water and oil repellency, but also an antisoiling property against solid soil such as mud or dust, i.e. a dry soil resistance and a soil-removal property whereby soil can readily be removed. When a conventional fluorine-type water and oil repellant is used as an antisoiling composition in this field, water and oil repellency may be obtained to some extent, but it is difficult to obtain adequate dry soil resistance or its durability, since the hardness of a coating formed on the fiber surface is inadequate.
Therefore, the following treating agents (1) to (6) i.e. compositions comprising a fluorine-containing compound and another compound for improving the coating hardness, or treating agents made of e.g. a fluorine-containing copolymer having a high coating hardness, have been proposed.
(1) A mixture comprising a polymer main agent for imparting water and oil repellency and a polymer for imparting dry soil resistance,
(2) A mixture comprising a polymer containing no fluorine atom and a polyfluoroalkyl group-containing urethane compound (JP-A-55-128075),
(3) A mixture comprising a polymer having a polyfluoroalkyl group and a water-insoluble ester having both a fluorine atom and a chlorine atom (JP-A-58-134143).
(4) A copolymer of a polymerizable perfluoroalkyl group-containing urethane compound with a monomer for imparting dry soil resistance,
(5) A yarn-treating agent comprising a perfluoroalkyl group-containing urethane compound or a carbodiimide compound,
(6) A mixture comprising a fluorine-containing compound having a certain specific urethane bond and a polymethyl methacrylate (JP-B-4-28829).
However, the above treating agents have various problems. For example, the treating agents (1), (2) and (3) provide no adequate performance unless they are used in high concentrations. The copolymer (4) requires many steps for its synthesis, and the operation of such steps is cumbersome. The treating agent (5) is incapable of imparting an adequate antisoiling property. The mixture (6) is a treating agent for flame retardancy, but it is inadequate in the basic performance of e.g. dry soil resistance or soil-removal property, and its texture at the time of treatment is not satisfactory.
It is an object of the present invention to provide an antisoiling composition which satisfies both water and oil repellency and dry soil resistance (durability of an antisoiling property and a soil-removal property). Namely, it is an object of the present invention to provide an antisoiling composition whereby the hardness of a coating formed is high, durability of an antisoiling property against solid soil such as mud or stone dust, is high, and deposited soil can readily be removed.
The present invention provides an aqueous dispersion type antisoiling composition comprising an aqueous medium, and fine particles of the following reaction product (A) and fine particles of the following addition polymer (B), dispersed in the aqueous medium, or an aqueous medium, and fine particles comprising the reaction product (A) and the addition polymer (B), dispersed in the aqueous medium:
Reaction product (A): a reaction product of compounds (a1), (a2) and (a3);
Compound (a1): a compound having a polyfluoroalkyl group and a group having an active hydrogen atom reactive with an isocyanate group;
Compound (a2): a compound having no polyfluoroalkyl group and a group having an active hydrogen atom reactive with an isocyanate group;
Compound (a3): a polyisocyanate compound;
Addition polymer (B): a copolymer comprising polymer units of a polyfluoroalkyl group-containing (meth)acrylate and polymer units of methyl methacrylate.
Now, the present invention will be described in detail with reference to the preferred embodiments.
In the following description, “a polyfluoroalkyl group” will be represented by “a R
f
group”, “a perfluoroalkyl group” will be represented by “a R
F
group”, and “a group having an active hydrogen atom reactive with an isocyanate group” will be represented by “an active hydrogen-containing group”. Further, “acrylate and/or methacrylate” will be represented by “(meth)acrylate”. A similar representation applies to other expressions such as “(meth)acrylic acid”.
The reaction product (A) in the present invention is a reaction product of compounds (a1), (a2) and (a3) and is usually a reaction product obtained by a condensation reaction of such compounds.
The compound (a1) is a compound having a R
f
group and an active hydrogen-containing group. As the compound (a1), preferred is a compound having one R
f
group and one active hydrogen-containing group.
The R
f
group is 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 4 to 20, particularly preferably from 6 to 16. The R
f
group may be of a linear structure or a branched structure. Further, the R
f
group may have an etheric oxygen atom inserted between a carbon-carbon bond or may contain a carbon-carbon double bond.
The number of fluorine atoms in the R
f
group is preferably at least 60%, particularly preferably at least 80%, when represented by [the number of fluorine atoms in the R
f
group/the number of hydrogen groups contained in the corresponding alkyl group having the same carbon number as the R
f
group]×100 (%). Further, as the R
f
group, preferred is a group having all hydrogen atoms in the alkyl group substituted by fluorine atoms i.e. a R
F
group represented by the formula C
m
F
2m+1
— (wherein m is an integer of from 4 to 20), and particularly preferred is a linear R
F
group wherein the average of m is from 6 to 16.
The R
f
group may be a group having hydrogen atoms or chlorine atoms at the terminal portion, or may be a group having an oxypolyfluoroalkylene moiety. For example, the terminal may be a difluoromethyl group or a chlorodifluoromethyl group.
Specific examples of the R
f
group will be given below, but the R
f
group is not limited to such specific examples.
C
4
F
9
— (any one of structurally isomeric groups, such as F(CH
2
)
4
—, (CF
3
)
2
CFCF
2
—, (CF
3
)
3
C— or CF
3
CF
2
CF(CF
3
)—), C
5
F
11
— (such as F(CF
2
)
5
—), C
6
F
13
— (such as F(CF
2
)
6
—), C
7
F
15
— (such as F(CF
2
)
7
—, C
8
F
17
— (such as F(CF
2
)
8
—), C
9
F
19
— (such as F(CF
2
)
9
—), C
10
F
21
— (such as F(CF
2
)
10
—), and H(CF
2
)
p
— (wherein p is an integer of from 2 to 16).
As the compound (a1), preferred is a compound represented by the following formula 1. Namely, preferred is a compound wherein the R
f
group and an active hydrogen-containing group are indirectly bonded via a connecting group. Particularly preferred is a compound wherein one R
f
group is bonded to an active hydrogen-containing group via a bivalent organic group.
R
f
—Q—X formula 1
In the formula 1, R
f
represents a R
f
group and is preferably a R
F
group. Q represents a bivalent connecting group, and X represents an active hydrogen-containing group, or a hydrogen atom when the X side terminal of Q is an oxygen atom, a nitrogen atom or a sulfur atom. It is preferred that at least one hydrogen atom is bonded to the carbon atom of R
f
bonded to Q.
Preferred as Q is, for example, —(CH
2
)
n
—, —CO—, —CONR—, —SO
2
NR—, —SO
2
NR(CH
2
)
n
—, —SO
2
—, —C
6
H
4
— (1,4—phenylene group), —C
6
H
3
Cl—(chloro-1,4—phenylene group) or —OC
2
H
4
— (wherein R is a hydrogen atom or a C
1-6
alkyl group, and n is an integer of from 1 to 20). In Q, —CONR— may be —NRCO—, and likewise, the direction is not questioned also with respect to other groups. Among these groups, preferred is —(CH
2
)
n
— or —SO
2
NR(CH
2
)
n
— (wherein R is a C
1-6
alkyl group
Maekawa Takashige
Shimada Toyomichi
Asahi Glass Company Ltd.
Michl Paul R.
Oblon & Spivak, McClelland, Maier & Neustadt P.C.
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