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
2000-09-25
2002-05-14
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...
C524S507000
Reexamination Certificate
active
06387999
ABSTRACT:
This invention relates to a composition comprising a fluorine-containing ester and an oligourethane or a polyurethane. It further relates to a particularly advantageous process for preparing aqueous dispersions of such compositions and to the use of such compositions for treating fiber materials.
It is known to confer an oil and water repellent finish on fiber materials, especially functional textiles in the form of sheet material, by applying fluoropolymers to them. This frequently takes the form of applying polymers that contain perfluorinated radicals (R
F
) to the textiles in the form of aqueous dispersions. Useful polymers here include such acrylate homo- or copolymers, polyurethanes and polyesters as contain R
F
radicals.
The use of R
F
-containing acrylates for the treatment of textiles is described for example in U.S. Pat. Nos. 4,742,140, 5,725,789 and 3,491,169. The use of R
F
-containing polyurethanes is disclosed in U.S. Pat. Nos. 5,019,428, 3,923,715 discloses the use of mixtures of an R
F
-containing ester and a nonfluorinated vinyl polymer. EP-A 208 421 likewise describes mixtures for the oil and water repellent finishing of textiles. WO 95/33093 relates to the finishing of textiles with fluorinated compounds and extenders. Finally U.S. Pat. Nos. 4,264,484 and 4,401,780 likewise disclose mixtures which contain fluorinated fractions and are useful for the treatment of textile sheet materials.
Prior art compositions do not have optimal properties with regard to the oil and water repellent finishing of textile materials. First, the stability of aqueous dispersions of a number of such compositions is unsatisfactory. This is a disadvantage because the use of compositions for textile treatment in the form of aqueous dispersions is the technically and economically best method. Secondly, the desired performance level is in a number of cases achievable only, if at all, with high product add-ons on the textile. Thirdly, it is a frequently observed disadvantage that the performance of finished textiles deteriorates excessively on abrasion because, in use, ie. under mechanical stress, a certain proportion of the finishing products on the surface of the textile is removed by abrasion, and this has an adverse effect on the permanence of the finishing effects.
It is an object of the present invention to provide a composition for conferring a highly effective oil and water repellent finish on fiber materials that is obtainable in the form of very stable aqueous dispersions and that provides finished fiber materials with minimal if any post-abrasion deterioration in performance.
This object is achieved by a composition comprising a component A and a component B, component A being an ester or a mixture of esters and being obtainable by reacting a dicarboxylic acid or a mixture of dicarboxylic acids of the formula (I)
HOOC&Parenopenst;CH R&Parenclosest;
a
COOH (I)
with a diol or a mixture of diols selected from diols of the formulae (II) to (XI)
[R
F1
&Parenopenst;CH
2
&Parenclosest;
b
&Parenopenst;X—CH
2
&Parenclosest;
c
]
2
C(CH
2
OH)
2
(II)
HO—CH
2
—CRR′&Parenopenst;X&Parenclosest;
d
CRR′—CH
2
OH (III)
HO&Parenopenst;CH
2
&Parenclosest;
e
&Parenopenst;SiR
2
—O&Parenclosest;
f
SiR
2
&Parenopenst;CH
2
&Parenclosest;
e
OH (IV)
HO—CH
2
CH
2
—N R″—CH
2
CH
2
OH (V)
HO&Parenopenst;CHR&Parenclosest;
t
&Parenopenst;CHR—CHR—O&Parenclosest;
g
CHR—CHR—OH (VI)
[R
F2
&Parenopenst;CH R
2
&Parenclosest;
b1
C(R
2
)(OH)—CH R
2
—]
2
X
1
(VII)
[R
F2
—CH═CH—CH
2
—Y—CH
2
—C(R
2
)(OH)—CH
2
—]
2
X
1
(VIII)
[R
F2
—CH═CH—CH
2
—Y—CH
2
—C(R
2
)(Z)—CH
2
—]
2
X
1
(IX)
[R
F2
—CH═CH—CH
2
—X
1
—CH
2
—]
2
C(CH
2
OH)
2
(X)
[R
F2
&Parenopenst;CHR
2
&Parenclosest;
b1
C(R
2
)(Z)—CHR
2
—]
2
X
1
(XI)
subject to the proviso that at least one diol of the formula (II) or of the formula (III) or of one of the formulae (VII) to (XI) participate in the reaction, and component B being an oligourethane or polyurethane obtainable by reacting a diol or a mixture of diols selected from diols of the formulae (II) to (XII)
(HO—CH
2
)
3
C—H
2
—CH
3
(XII)
with a diisocyanate or a mixture of diisocyanates of the formula (XIII)
OCN—R′″—NCO (XIII)
where any R is independently of the others hydrogen or an alkyl radical of 1 to 4 carbon atoms,
a is from 2 to 10, preferably from 2 to 6,
b is from 1 to 4,
c is 0 or 1,
d is 0 or 1,
R
F1
is CF
3
&Parenopenst;CF
2
&Parenclosest;
h1
,
h1 is from 3 to 15, preferably from 7 to 11,
R′ is &Parenopenst;CH
2
&Parenclosest;
b
when d is 1 and —X&Parenopenst;CH
2
&Parenclosest;
b
when d is 0,
e is from 1 to 4,
f is from 10 to 50,
g is from 0 to 6,
t is from 0 to 8,
X is —O—, —S—, —NR— or —PR—, preferably —S—,
R″ is R or —CH
2
CH
2
OH,
X
1
is —O—, —S—, —NR
2
—, —PR
2
—, —S&Parenopenst;CH
2
&Parenclosest;
b1
S—, &Parenopenst;S&Parenclosest;
u
, —S(O
2
)— or —S(O
2
)—(CH
2
&Parenclosest;
b1
S(O
2
)— preferably —S—,
Y is —O—, —S—, —NR
2
— or —PR
2
—, preferably —O—,
Z is &Parenopenst;CH
2
&Parenclosest;
c1
&Parenopenst;OC
p
H
2p
&Parenclosest;
e1
&Parenopenst;OCHR—CHR&Parenclosest;
d1
OH,
b1 is from 1 to 4, preferably 1,
c1 is from 0 to 18,
d1 is from 0 to 8,
R
F2
is CF
3
&Parenopenst;CF
2
&Parenclosest;
h2
,
h2 is from 3 to 19, preferably from 7 to 11,
e1 is from 0 to 8,
any R
2
is independently of the others hydrogen or a branched or unbranched alkyl radical of 1 to 18, preferably 2 to 6 or 16 to 18, carbon atoms,
p is from 3 to 8,
u is from 2 to 8,
R′″ is a divalent aliphatic or cycloaliphatic radical of 4 to 40 carbon atoms or is a divalent aromatic radical of the formula
—C
6
H
3
(R)— or —C
6
H
3
(R)—CH
2
—C
6
H
3
(R)— or —C
6
H
3
(R)—CR
2
—C
6
H
3
(R)—,
where C
6
H
3
is a trivalent radical derived from benzene, and if desired blocking any isocyanate groups left in the reaction product of diol and diisocyanate.
Compositions according to the invention are very useful for the treatment of fiber materials, especially textile sheet materials such as upholstery fabrics. The fiber materials here are preferably textile sheet materials which are 50 to 100% by weight synthetic polymer, especially polyester, polyacrylonitrile or polyamide or mixtures thereof, and 0 to 50% by weight native fiber, especially cellulose. The sheet materials acquire oil and water repellent properties as a result. A particular advantage of the use of compositions according to the invention is that the finished fiber materials suffer little if any loss of oil and water repellent performance on mechanical abrasion. Treatment with compositions according to the invention also makes it possible to confer a pleasantly soft hand and substantial resistance to yellowing on fiber materials.
Compositions according to the invention are preferably used in the form of aqueous dispersions. A preferred embodiment thus includes water and one or more dispersants as well as the components A and B. They preferably include at least one nonionic dispersant or a mixture of nonionic dispersants. In individual cases it is also possible for them to additionally include an anionic, cationic or amphoteric dispersant. In some cases, useful aqueous dispersions are obtainable by using a mixture of a nonionic dispersant and a cationic dispersant.
Compositions according to the invention include at least a component A and a component B.
Component A is an ester or a mixture of esters obtainable by reacting a dicarboxylic acid or a mixture of dicarboxylic acids of the formula (I)
HOOC&Parenopenst;CH R&Parenclosest;
a
COOH (I)
with a diol or a mixture of diols selected from diols of the formulae (II) to (XI)
[R
F1
&Parenopenst;CH
2
&Parenclosest;
b
&Parenopenst;X—CH
2
&Parenclosest;
c
]
2
C(CH
2
OH)
2
(II)
HO—CH
2
—CRR′&Parenopenst;X&Parenclosest;
d
CRR′—CH
2
OH (III)
HO&Parenopenst;CH
2
&Parenclosest;
e
&Parenopenst;SiR
2
—O&Parenc
Artner Wilhelm
Dirschl Franz
Gaugenrieder Heinz
Lüdemann Simpert
Schidek Edeltraud
Ciba Specialty Chemicals Corporation
Mansfield Kevin T.
Michl Paul R.
LandOfFree
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