Process for producing anti-soil finishing agent

Details Process for producing anti-soil finishing agent Process for producing anti-soil finishing agent

2000-07-28

2002-05-14

Green, Anthony (Department: 1755)

Compositions

Durable finishes for textile materials, or processes of...

Oil or water repellent or soil resistant or retardant

C525S199000, C526S245000

Reexamination Certificate

active

06387292

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a process for producing an anti-soil finishing agent, and more particularly a process for producing an anti-soil finishing agent having a high flash point, a distinguished frozen stability, etc.
2. Related Art
Anti-soil finishing of fabrics is usually carried out by making fabrics hydrophilic or finishing with fluorine-based resins, silicone resins, oil and fat, etc. Above all, finishing with fluorine-based resin is based mainly on anti-soil finishing effect of fluorine on water- and oil-repellency or on a flip-flop mechanism derived by combination with hydrophilic groups, and is now most widely used owing to their properties and easy finishing procedure.
The finishing with the fluorine-based resin is carried out mainly with copolymers of fluoroalkyl group-containing (meth)acrylate esters with hydrophilic group-containing (meth)acrylate esters (e.g. JP-B-52-35033, JP-B-63-474, U.S. Pat. No. 3,574,791, etc.), and the copolymers are generally produced by solution polymerization, where the copolymerization reaction is based on reaction of monomers of mutually contracting properties, i.e. reaction of fluoroalkyl group-containig monomers with hydrophilic group-containing monomers and therefore the solution polymerization reaction is carried out upon appropriate selection of a best solvent for both monomers. Practically, solvents with a low flash point, e.g. alcohols such as ethanol, isopropanol, etc. and ketones such as acetone, methylisobutyl ketone, etc. or mixtures thereof with water are used in most cases (JP-A-53-134786).
Solution polymerization procedure requires no pre-emulsification by a homogenizer, etc. and no complicated polymerization operation, but a high flash point type is desirable from the viewpoints of a risk problem of solvent inflammability, etc. and an ecological problem. One of these problems can be easily solved by using a solvent of high flash point, but the polymerization reaction using such a solvent is not only costly, but also brings about a failure in dispersion when the polymerization reaction solution is diluted with water, resulting in poor stability as another problem.
SUMMARY OF THE INVENTION
An object of the present invention is to provide a process for producing an anti-soil finishing agent having not only a high flash point, but also distinguished frozen stability and high temperature stability (storage stability at a temperature of about 40~50° C. higher than room temperature).
The object of the present invention can be attained by producing an anti-soil finishing agent by copolymeriging a fluoroalkyl group-containing monomer with a hydrophilic group-containig monomer in polypropylene glycol having an average molecular weight of not more than about 1,000 or a mixture thereof with a water-soluble organic solvent having a boiling point of not less than 150° C. or a flash point of more than 61° C.
DETAILED DESCRIPTION OF THE INVENTION
Generally, fluoroalkyl group-containing (meth)acrylate esters are used as a fluoroalkyl group-containing monomer, where a perfluoroalkyl group Rf having 6, 8, 10 or 12 carbon atoms or a mixture thereof is preferably used as a fluoroalkyl group and specifically include the following compounds, wherein m being 4, 6, 8, 10 or 12, or a mixture thereof:
CH
2
═CHCOOCH
2
CH
2
Rf
CH
2
═C(CH
3
)COOCH
2
CH
2
Rf
CH
2
═CHCOOCH
2
CH(OH)CH
2
Rf
CH
2
═C(CHCOOCH
2
CH(OH)CH
2
Rf
CH
2
═CHCOO(CH
2
)
3
C
8
F
17
CH
2
═CHCOO(CH
2
)
4
CEF
17
CH
2
═CHCOOCH
2
CH
2
(CF
2
)
m
CF(CF
3
) 2
CH
2
═C(CH
3
)COOCH
2
CH
2
(CF
2
)
m
CF(CF
3
)
2
CH
2
═CHCOOCH
2
CH
2
N(CH
3
)SO
2
C
8
F
17
CH
2
═C(CH
3
) COOCH
2
CH
2
N(CH
3
)SO
2
C
8
F
17
CH
2
═CHCOOCH
2
CH
2
N(C
2
H
5
)SO
2
C
8
F
17
CH
2
═C(CH
3
)COOCH
2
CH
2
N(C
2
H
5
)SO
2
C
8
F
17
CH
2
═CHCOOCH
2
CH
2
N(C
3
H
7
)SO
2
C
8
F
17
CH
2
═C(CH
3
)COOCH
2
CH2N(C
4
H
9
)SO
2
C
8
F
17
CH
2
═CHCOOCH
2
CH
2
N(C
4
H
9
)SO
2
C
8
F
17
CH
2
═C(CH
3
)COOCH
2
CH
2
N(C
4
H
9
)SO
2
C
8
F
17
Generally, hydrophilic group-containing (meth)acrylate esters are used as a hydrophilic group-containing monomer, and compounds represented by the following general formula are preferably used:
CH
2
═CRCOO(CH
2
CH
2
O)
m
[CH
2
CH(CH
3
)O]
n
R′
R: Hydrogen atom or methyl group
R′: Hydrogen atom or lower alkyl group
m: Integer of 1 or more
n: 0 or an integer of 1 or more
m+n:1-60
The fluoroalkyl group-containing monomer and the hydrophilic group-containing monomer are subjected to copolymerization reaction so that the resulting copolymer can have a ratio of the former to the latter of about 30-80 wt. % : about 70-20 wt. %, preferably about 30-60 wt. % : about 70-40 wt. %, total being 100 wt. %. An appropriate monomer ratio of the copolymer can be selected in view of a balance between the lipophilic property and the hydrophilic property of the resulting copolymer.
In addition to the foregoing monomers, other vinyl monomers can be further copolymerized therewith in a proportion of not more than about 30 wt. % to the sum total of the foregoing monomers to modify the copolymer or improve the adhesiveness to fibers. Such vinyl monomers include 3% (meth)acrylate esters having other hydrophobic groups than fluorine, hydrophilic group-containing (meth)acrylate esters having a lower molecular weight than that of the aforementioned hydrophobic group-containing monomers, cationic or anionic (meth)acrylate esters, etc. and specifically include the following compounds:
CH
2
═CHCOOCH
2
CH(OH) CH
3
CH
2
═C(CH
3
)COOCH
2
CH(OH)CH
3
CH
2
═CHCOOCH
2
CH(OH)CH
2
0H
CH
2
═C(CH
3
)COOCH
2
CH(OH)CH
2
OH
CH
2
═CHCOOCH
2
CH(OH)CH
2
CH
3
CH
2
═C(CH
8
)COOCH
2
CH(OH)CH
2
CH
3
CH
2
═CHCOOCH
2
CH
2
CH
2
CH
2
OH
CH
2
═C(CH
3
)COOCH
2
CH
2
CH
2
CH
2
OH
CH
2
═CHCOOCH
2
CH
2
OCH
3
CH
2
═C(CH
3
)COOCH
2
CH
2OCH
3
CH
2
═CHCOOCH
2
CH
2
OCH
2
CH
3
CH
2
═C(CH
3
)COOCH
2
CH
2
OCH
2
CH
3
CH
2
═CHCOOCH
2
CH
2
OCH
2
CH
2
CH
2
CH
3
CH
2
═C(CH
3
)COOCH
2
CH
2
OCH
2
CH
2
CH
2
CH
3
CH
2
═CHCOOC
2
H
4
N
+
(CH
3
)
3
Cl
−
CH
2
═C(CH
3
)COOC
2
H
4
N
+
(CH
3
)Cl
−
CH
2
═C(CH
3
)COOC
2
H
4
N
30
(CH
3
)
3
OSO
3
CH
3
31
CH
2
═C(CH
3
)COOC
2
H
4
N
+
(C
2
H
5
)
2
HCl
31
CH
2
═C(CH
3
)COOC
2
H
4
N
+
(CH
3
)
3
Br
31
CH
2
═C(CH
3
)COOC
2
H
4
N
+
H(C
2
H
5
)
2
CH
3
COO
31
CH
2
═C(CH
3
)COOCH
2
CH(OH)CH
2
N
+
(C
2
H
5
)
3
Cl
31
The following vinyl compounds can be also likewise used: benzyl (meth)acrylate, cyclohexyl (meth)acrylate, methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, hexyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, acrylonitrile, acrylamide, vinyl acetate, styrene, chlorostyrene, chlorobutyl vinyl ether, chloropropyl vinyl ether, chloroethyl vinyl ether, chloromethyl vinyl ether, N-methylol (meth)acrylamide, N-methylol acrylamide butyl ether, N-methylol (meth)acrylamide methyl ether, etc.
The foregoing monomers are subjected to solution polymerization in polypropylene glycol of water-soluble diol type or triol type having an average molecular weight of not more than about 1,000. The polypropylene glycol is used in an amount of about 1-10 times, preferably about 1.5-6 times the total weight of the monomers.
A water-soluble organic solvent having a boiling point of not less than 150° C. or a flash point of more than 61° C. can be used together with the polypropylene glycol, where the polypropylene glycol is used in an amount of about 0.1-2 times the total weight of the monomer and the water-soluble organic solvent is used in an amount of not more than about 3 times the total weight of the monomers.
The water-soluble organic solvent for use in the present invention includes, e.g. glycol ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, propylene glycol monomethyl ether, propylene glycol monoe

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