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Патент USA US3058858

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United States Patent 0 “ice
Patented Get. 15, 1962
It is still a further object of this invention to obtain
anti-crease ?nishings which retain the soft feel and res
piratory activity of the non-treated fabric.
The ethers of the dimethylol-imidazolidone-2 which
Giinter Gruber, Frankfurt am Main-Feehenheim, and
Hans-Andreas Wannew, Frankfurt am Main, Germany,
being soluble in water, such as the methyl-, propyl- o1‘
may be used under this invention are in particular those
assignors to tCasseiia Farhwerke Mainkur Aktiengesell
schait, Frankfurt am Main-Feehenheim, Germany, a
company of Germany
No Drawing. Fiied .iune 6, 1960, Ser. No. 33,924
Ciairns priority, appiicatien Germany June 11, 1959
4 (Iiairns. (Cl. 117—~13£P.4)
The ethers of the dimethylol
imidazolidone-2 containing unsaturated alcohols, such as
'allyl alcohol which are soluble in the impregnating ‘baths
exhibit a particularly favorable action. Even ethers
10 which contain higher alcohols, such as butyl alcohol, and
are insoluble in the impregnating liquors may be em
ployed. In this case the water-insoluble ethers have to
be admixed, in form of an emulsion, to the solution
This invention relates to a process for ?nishing cellu
‘lose materials. More particularly it relates to an anti
crease ?nishing which is resistant to chlorine by applying
dimethylol-imidazolidone-2 together with ethers derived
from dimethylol-imidazolidone-Z. The present invention
containing the dimethylol~imidazolidone-2 during the
impregnation of the fabric.
The production of the ethers mentioned above is
also relates to a novel composition of matter which is
effected according to known methods.
suitable for use in anti-crease ?nishing of cellulose fabrics.
The following examples of the method of the present
It is known that dimethylol-imidazolidone-Z in the
invention are given as illustrative only, the parts being
presence of suitable acid-forming agents imparts an ex 20 by weight and all temperatures in degrees centigrade,
cellent crease resistance to fabrics consisting of cellulose
the invention, however, not being limited to the speci?c
?bers, in particular to cotton. Further, it is known that
details of the examples:
?nishes of dimethylol-imidazolidone-2 present a chlorine
Example 1
retaining power owing to the content of nitrogen, es
pecially in those cases where, during the ?nishing of the 25 A bleached and mercerized fabric consisting of a cot
fabrics, the condensation was carried out below 150°.
ton poplin mixed fabric is impregnated on the padding
The chlorine retaining power has detrimental effects in
machine with an aqueous solution of:
that the fabrics thus ?nished assume a yellow discolora
tion and lose their strength when subjected, after
45 grams/ liter dimethylol-imidazolidone-Z
intense washing, to chlorine treatment and heating 30 15 grams/ liter diallyl-dimethylol-imidazolidone-2
Moreover, it is known from the US. patent speci?
15 grams/ liter crystallized magnesium chloride,
cation 2,373,136 that ethers of the dimethylol-imidaz
the pick-up of liquor is 75% on the weight of the air
olidone-2 may be also used for crease-proof ?nishing.
dried fabric. Subsequently, the fabric is dried at tem
The resultant effects, however, as regards the improve
peratures of 60—80° and afterheated at 130° during 3
ment of the crease resistance are so low that such proc
esses have not become of practical interest.
Two groups of samples of the fabric thus ?nished were
Furthermore, it is known that aminotriazineaformalde
washed with 3 grams/liter Marseilles soap and 2 grams/
hyde resins (according to US. patent speci?cations No.
liter calcined soda at boiling temperature 3 or 10 times
2,690,404 and U.S. 2,833,674) or polymeriza-ble vinyl 40 each ‘for half an hour and subsequently subjected to
or vinylidene compounds together with a compound co
chlorine stability test which is conducted as follows:
polymerizable therewith (according to US. patent speci
In connection with the Tentative Test Method 69-52,
?cation No. 2,755,198) may be added to the impregnat
“Damage Caused ‘by Retained Chlorine,” by the Amer
ing liquors with a view to reducing the chlorine retain
ican Association of Textile Chemists and Colorists, the
ing power of fabrics ?nished with dimethylol-imidaz
?nished fabric cutting is boiled out at ?rst in distilled
olidone-Z. The ?nishings so obtained, however, do no
water for 3 minutes and treated at 27° for 15 minutes
longer exhibit the soft feel and the high respiratory
in the wetted state with a sodium hypochlorite solution
activity of the non-?nished ‘fabric which is due to the
containing v0.25% active chlorine in the liquor ratio 1:50.
resinous nature of the additives as above mentioned.
Then the chlorinated sample is rinsed in fresh water for
Now, we have found surprisingly that the detrimental -
e?ects of the chlorine retaining power may be avoided
in the case of anti-crease ?nishing of fabrics which are
improved with dimethylol-imidazolidone-Z by impreg
nating the fabric with liquors ‘containing a mixture of
dimethylol-irnidazolidone? and ethers thereof prepared
from dimethylol-imidazolidone-2 with aliphatic alcohols,
and ?nishing by drying and heating the impregnated ma
one minute at a temperature of ‘2l—27°, afterwards the
excess water being squeezed by hand and this rinsing
process being repeated ‘6 times. Subsequently, the sam
ple is dried in the drying oven at 80° and suspended
55 for 4 hours in an air-conditioned test room possessing
a temperature of 20° and a relative dampness of 65%.
At the end of this period the ?nished sample is heated
for 30 seconds with an ironing press, the metal plate of
terial to ?x the impregnating agents onto the fabric.
which is heated to 185°.
The ratio between dimethylol-imidazolidone-2 and its
To make comparisons as to the deterioration of the
ether may range from 95—60% to 5—40%, whereby the 60 ?ber during the heating process that is caused by the
impregnating liquors may contain 20 to 100 grams of
chlorine retaining power, the ?nish is prepared with di
the mixture per liter solution. Concentration and con
without admixing the ‘allyl
ditions of application may be controlled to provide 1 t0
ether by means of an aqueous solution of:
7% pick-up of the impregnating ‘agents on the weight of
the fabric.
60 grams/liter dimethylol-imidazolidone-2
It is an object of the invention to provide anti-crease
15 grams/liter crystallized magnesium chloride
?nishings without any loss of strength of the treated
The treatment on the padding machine and the further
It is further object of this invention to provide anti
working processes as well as the investigations as to the
crease ?nishings which do not exhibit any discoloration
effects of the chlorine retaining power are effected as
when subjected, after intense washing, to chlorine treat
described above.
ment and subsequent ironing.
The present test yielded the following result:
an insigni?cant percentage in tensile strength after the
treatment with chlorine and subsequent heating of the
fabric which had "been washed repeatedly. Moreover,
Tensile strength (weft)
there was no discoloration to be observed, whereas a
3 washings
unwashed at boiling
fabric ?nished in the same method only with dimethylol
imidazolidone-Z gets brown and loses its stability almost
10 Wash
ings at
non-chlori- temperaboiling
nated, kg. ture, chlori- tempera
nated, kg. ture, chlori
nated, kg.
The bis-glycol-dimethylol-imidazolidone-2 which is
used in the above example may be prepared in the fol
10 lowing manner:
methylol~imidazolidone-2 and
the allylether thereof (accord
260 parts imidazolidone-Z and 190 parts paraformalde
hyde are dissolved at 5‘0—60° in 500 parts ‘glycol in the
presence of 0.5 part 10 n caustic soda lye. The ‘clear
(alone) _______________________ -_
33. 7_
viscous solution is cooled as low as 20°, admixed with
15 14 parts concentrated hydrochloric ‘acid and agitated for
1 hour at 2‘0-25°. Subsequently, the solution is neu
From the above table it becomes obvious ‘that the
tralized with 10 n caustic soda lye and sucked off from
tensile strength of the fabric ?nished with the mixture
the common salt which might have precipitated.
out ‘of dimethylol-imidazolidone-‘Z together with the allyl
Rough yield: 970 parts of a clear solution of about
ether of the dimethylol-imidazolidone-2 remained rather
ing to the present invention).--
32. 8
28. 9
27. 4
stable after chlorine treatment and subsequent heating, 20 50% bis-glycol-dimethylol-imidazolidone-2. The raw
material may be used straightly for the ?nish.
Whereas the fabric finished only with dimethylol-imidaz
It will bervunderstood that this invention is capable to
olidone-2 had been considerably destroyed under the
' further modi?cation and, ‘accordingly, it is desired to
same procedure. The considerable deterioration of the
include such modi?cations within this invention as may
fabric ?nished with dimethylol-imidazolidone-2 which
fall within the scope of the appended claims.
was caused by the chlorine treatment during the heating
We claim:
and repeated washing process, may furthermore 1be ob
1. An article of manufacture comprising ‘a cellulosic
served in an intense browning of the material. In con
fabric containing from 1 to 7% of an anti-crease mixture
of dimethylol-irnidazolidone-Z and an ether thereof
trast thereto, the fabric ?nished with the mixture out of
dimethylol-imidazolidone-Z and the allylether thereof,
which had ‘been subjected to the same test, remained 30 whereby the ratio between dimethylol-imidazolidone-2
and its ether range from 95-60% to 5~40%.
entirely white.
2. A process of anti-crease ?nishing ‘of cellulosic
The dially ether of the dimethylol-imidazolidone-2
fabrics which comprises impregnating the fabric with
utilized in the above example may be prepared as
258 parts imidazolidone-Z, 190 parts paraformaldehyde
impregnating liquors containing a mixture of dimethylol
imidazolidone-‘Z and ethers thereof whereby the ratio be
tween dimethylol-imidazolidone-2 and its ether ranges
from ‘95-60% to 5—40% and the impregnating liquors
and 1000 parts \allyl alcohol are stirred in the presence of
1 part 10 n caustic soda lye at 50~6'0°. After approxi
contain 20 to 1100 grams of the mixture per liter of
mately 20 minutes’ time the mixture is cooled down to
room temperature and admixed in portions with 20 parts 40 solution, controlling the concentration and conditions of
application to provide 1 to 7% pick-up of the impreg
in total of concentrated hydrochloric acid while stirring.
nating agents on the weight of the fabric, ‘and ?xing the
The temperature is held for 1 hour at 20~25°. Then
impregnating agents on the ‘fabric by drying and heating
the solution is neutralized with caustic soda lye, the ex
the impregnated materials.
cess allyl alcohol distilled, sucked off from the resultant
sodium chloride and the ?ltrate is distilled in the high 45 3. The process according to claim 2 wherein the im-'
pregnating liquor contains a mixture of dimethylol
vacuum. The diallyl-dimethylol-imidazolidone-2 has a
midazOlidione-Z and the diallyl ether of ‘dimethylol
boiling point of 145 °/2 mm.
Example 2
imidazolidone-Z with the ratio between dimethylol
imidazolidone-Z and its ether ranges from 95-60% to
A cotton fabric treated with caustic soda ‘and bleached
4. The process ‘according to claim 2 wherein the im
is ?nished with an aqueous solution consisting of:
v50 grams/liter dimethylol-imidazolidone-2
20 grams/liter Ibis-glycol-dimethylol-imidazolidone-2
15 grams/liter crystallized magnesium chloride
as described in Example 1 ‘and subjected to the chlorine 55
stability test. It becomes apparent that a’fabric ?nished
with dimethylol-imidazolidone-2 in the presence of its
ethyleneglycolether according to this recipe loses only
pregnating liquor contains a mixture consisting of di
methylol-imidazolidone-Z and the diethylene-glycol ether
of the dimethylol-imidazolidone-Z.
References Cited in the ?le of this patent
Hoover et a1 __________ __ Apr. 10, 1945
Barnard et al. _________ __ Jan. 7, ‘1958
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