Language selection

Search

Patent 1186456 Summary

Third-party information liability

Some of the information on this Web page has been provided by external sources. The Government of Canada is not responsible for the accuracy, reliability or currency of the information supplied by external sources. Users wishing to rely upon this information should consult directly with the source of the information. Content provided by external sources is not subject to official languages, privacy and accessibility requirements.

Claims and Abstract availability

Any discrepancies in the text and image of the Claims and Abstract are due to differing posting times. Text of the Claims and Abstract are posted:

  • At the time the application is open to public inspection;
  • At the time of issue of the patent (grant).
(12) Patent: (11) CA 1186456
(21) Application Number: 1186456
(54) English Title: PROCESS FOR THE DYEING OR PRINTING OF TEXTILE MATERIAL OF CELLULOSE FIBERS OR MIXTURES THEREOF WITH OTHER FIBERS WITH REACTIVE DYESTUFFS
(54) French Title: METHODE DE TEINTURE DES TEXTILES A BASE DE CELLULOSE OU DE SON MELANGE AVEC D'AUTRES FIBRES, ET D'IMPRESSION SUR CES MEMES TEXTILES, A L'AIDE DE COLORANTS REACTIFS
Status: Term Expired - Post Grant
Bibliographic Data
(51) International Patent Classification (IPC):
  • D06P 3/66 (2006.01)
  • C09B 67/26 (2006.01)
  • D06P 3/82 (2006.01)
(72) Inventors :
  • GLANDER, SIEGFRIED (Germany)
  • SCHON, FRANZ (Germany)
(73) Owners :
  • HOECHST AKTIENGESELLSCHAFT
(71) Applicants :
  • HOECHST AKTIENGESELLSCHAFT (Germany)
(74) Agent: SMART & BIGGAR LP
(74) Associate agent:
(45) Issued: 1985-05-07
(22) Filed Date: 1982-06-04
Availability of licence: N/A
Dedicated to the Public: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): No

(30) Application Priority Data:
Application No. Country/Territory Date
P 31 22 560.8 (Germany) 1981-06-06

Abstracts

English Abstract


Abstract of the disclosure
Certain reactive dyestuffs of commercial constitu- .
tion are available in a form which does not react with
cellulose fibers and have therefore to be converted into
their reactive form before being able to undergo a
covalent bond with the fiber materials. The methods
hitherto applied in the practice for this purpose are
unsatisfactory because they either do not produce a suffi-
cient amount of reactive dyestuff under the prevailing
conditions, or due to susceptibility of the converted
form to hydrolysis, portions of the dyestuff are in
activated, thus resulting in dyestuff losses in both cases.
In accordance with the invention these drawbacks
are overcome by converting first the dyestuffs to their
fiber-reactive form, before dyeing or printing, by
treating them under correspondingly typical conditions,
for example in an alkaline medium, and chemically
stabilizing then this converted form by alteration of
the pH, for example to the acidic range. The dyestuff
formulations so obtained are then used for the dyeing
or printing of cellulose fibers in a neutral to acidic
pH range. This is the decisive condition for acceptable
yields as compared to the hitherto known operation modes.


Claims

Note: Claims are shown in the official language in which they were submitted.


THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. In a process for the exhaust dyeing, pad-dyeing or
printing of textile material made from cellulose fibers or mixtures
thereof with other fibers, using a reactive dyestuff which in
commercial constitution is present in a form incapable of reacting
on its own with the fiber substance and containing reactive groups
being derived from esters of mono- or polyvalent, inorganic or
organic acids easily split off, with a .beta.-hydroxyethylsulfone
compound, the improvement which comprises converting the reactive
dyestuff, before application, in an aqueous medium by treatment
with an alkaline agent from the non-fiber-reactive to the fiber-
reactive vinylsulfone form and chemically stabilizing it in this
converted form by adjusting to a neutral to acidic pH range by
adding acid to the alkaline dyestuff solution, and subsequently
applying the dyestuff formulation thus obtained to the fiber
material from an aqueous, neutral to acidic medium by exhaust
dyeing, pad-dyeing or printing, and fixing the dyestuff on the
fiber.
2. A process as claimed in claim 1, wherein as reactive
dyestuff there is used a dyestuff containing as reactive group at
least one sulfatoethylsulfone radical.
3. A process as claimed in claim 1, wherein as alkaline
agent there is used an aqueous solution of alkali metal hydroxide
or salt having an alkaline reaction in water or a mixture of such
hydroxide and salt.
-16-

4. A process as claimed in claim 1, wherein dyeing according
to the exhaust method is carried out within 15 to 180 minutes at a
temperature of from 20° to 140°C.
5. A process as claimed in claim 1, wherein fixation of the
dyestuff after padding or printing is carried out by dry heat
treatment for 30 seconds to 10 minutes at a temperature of from
120° to 240°C, by steaming for 30 seconds to 30 minutes at a
temperature of from 100° to 240° or by a combination of dry heat
treatment and steaming.
6. A process as claimed in claim 5 wherein the fixation is
carried out after an intermediate drying of the material following
the dyestuff application operation.
7. A process as claimed in claim 1, wherein for the dyeing
or printing of fiber mixtures the formulation of the reactive
dyestuff is used together with one or more dyestuffs of other
categories.
8. A process as claimed in claim 1, wherein fiber mixtures
of cellulose fibers with polyester fibers or of cellulose fibers
with natural or synthetic polyamide fibers are dyed or printed.
9. A liquid reactive dyestuff formulation capable of being
infinitely diluted with water and suitable for carrying out the
process as claimed in claim 1, in which a dyestuff of commercial
constitution is present in a form incapable of reacting on its own
with the fiber substance and containing reactive groups being
-17-

derived from esters of mono- or polyvalent, inorganic or organic
acids easily split off, with a .beta.-hydroxy-ethylsulfone compound,
the reactive dyestuff having been converted in an aqueous medium
by treatment with an alkaline agent from the non-fiber-reactive
to the fiber-reactive vinylsulfone form and having been
chemically stabilized in this converted form by adjusting to a
neutral to acidic pH range by adding acid to the alkaline dyestuff
solution.
-18-

Description

Note: Descriptions are shown in the official language in which they were submitted.


3l.~L ~
- 2 - IIOE 81/F_139
. .
The present invention relates to the exhaust dyeincJ,
pad-dyeing or printing of textile material made frorn
cellulose fibers or mi.xtures tllerevf wi-th other fibers
with reactive dyestuffs which in cor~.erci.al constitut:ion
are present in a form incapable of reactiny by itself
with the fiber substance, and which from an aqueous
medium are otherwise induced to fixation on the fiber
according to ~nown dyeing processes ~i) ei.ther directly
in their non-reactive fol-m under acidic conditions or (ii)
be converted to their reactive form by the in:Eluence of
alkali.ne agents durinc3 the dyeing operatlon prior to bei.ng
fixed under the alkaline conditions resultincJ therefrom.
The invention comprises furthe.rmore special formulations
of such reactive dyes suitable for application in the
novel process
Dyeinc3 with so-called reactive dyes islas principally
cellulose fibers are concerned, already known ~or a cer-tai.n
time and has fully proved its worth in the practice
because of the clear and dull shades and the fastnesses
so obtainable. Such coloring a~ents are of organi.c ori.~in
and li.sted in Colour Inc~ex, 3rd edition 1971, under tl1e
generic term "Reactive Dyes". DyestufEs of sai.d species
~elon~J to the serles to azo-, anthraquinone-- or phthalo-
cyanine compounds ~hich may be present in the form of
m~tal complexes and which contain at least one group
capable of reactlng with the fiber. ITI some cases, however,
such a group reactil1g with the Eiber is not present a
priori but formed by suitahle operations only in the dyeinc~
process froln precursor thereof. A current example of this
~o latter type are reacti.ve dyes on the b~sis of esters of
mono- or polyvalent, inorcJanic or orCJanic acids whichsar
easily be split OJ f, especial.ly of sul:fllric acid esters,
~ith B-hydroxyethyisuItone compounds ~st.er dyestuffs),
from which in the course of the dyeinc3 process by the
3~ in.luence oI allaline acJerlts the fiber-rea-_tive V:il~7l.-
' '~.~ '.

-` 3.~
~ 3 - HO~ 139
suIfone form ~VS form) of the dyestuff is fGrmed.
For coloring cel]uIose text1es o all kinds, reac-
tive dyes aLe ap~lied accorcling to textile printillg
processes as well as exhaust or continuous dyeing
processes. In the industrial practice these dyestuffs
are usually fi~ed on the fiber prevailing frorn an
aquoues medium and primarily in the presence of alkaline
agents. Suitable fixation alkalis'are those which cause
the conversion from the commercial form of the ~ster
d~estuffs to the VS form reacting with the polyhydroxy
- fiber, either at roorn temperature or with the aid of
heating, depending on the reactivity degree of the
dyestuffs: In the exhaust processes, as a rule;sodium
hydroxide solution, sodium carbonate or trisodium phos
phate are used for said purpose~while in pad-dyeing
water glass and sodium bicarbonate are suitable as well
as sodium hydroxide solution and sodium carhonate.
Fixation of the reactive dyes in the e~haust process
occurs il~nediately after their absorption by the fiber
. 20 at temperatures of up to the boiling point of the d~yeing
bath, while in pad-dyeing after the application or -the
dyestuff a separate operation including dwelling, steamincJ
or dry heat treatment is required for the said proceeding.
Disadvantag~ous for the pad-dyeing processes is the
reduced stability of the reactive dyes ln the alka]ine
ran~e. Under these conditions, for example, froln VS
dyestuffs due to hydrolysis B-hydroxyethylsulfone
dyestllffs are formed which cannot react with the fiber.
Although this undesirable behavior can be overcome
by a two-bath trea-tment method according to WhiCIl first
the non-reactive Ester dyestu~f is applied without
~lkalis, and then the required amount of alkali is
supplied in a second padding operation, as the conse-
~uence for such â tactical roundahout way, however,
the disadvar.tage of an interlnedia-te dryiny must he
paid.

3~
When printing with reactive dyes, the reduced stability of these
dyes in an alkaline medium can be avoided by mixing to the print-
ing pastes so-called alkali donors which set free the alkali in
the fixation E)rocess at elevated temperatures only. Such alkali
donors are for example sodium bicarbonate, sodium trichloroacetic
acid or dicyano-diamide.
From the literature, further dyeing techniques are known
according to which the commercial reactive dyes are applied from
an aqueous, neutral or acidic medium onto cellulose fibers or
10 fiber mixtures containing cellulose, and fixed there under high
temperature (HT) conditions. Exhaust processes of this kind are
described for example in German Auslegeschrift No. 2,835,035 and
German Offenlegungsschriften Nos. 2,913,718 and 2,933,343, pad-
dyeing processes in German Auslegeschrift No. 2,834,998. However,
the often low dyestuff yield in -these processes, especially in the
case of Ester dyestuffs, is not satisfactory.
It has now been found that reactive dyestuffs which in
commercial constitution are present in a form non-reactive by
itself with the fiber substance give a good colour yield on dyeing
20 or printing of cellulose fibers when the said dyestuffs are pre-
treated (before dyeing or printing) in an aqueous medium in such
a manner that they are converted to their fiber-reactive form,
and then chemically stabilized in this latter form. Therefore,
this invention seeks to provide in a process for the exhaust
dyeing, pad-dyeing or printing of textile material made from
cellulose fibers or mixtures thereof with other fibers, using a
reactive dyestuff which in commercial constitution is present in
" .

~6~5~
a forrn ineapable of reacting on its own with the fiber substanee
and containing reactive groups being derived from esters of mono~
or polyvalent, inorganic or organic aeids easily split off, with a
~-hydroxyethylsulfone eompound, the improvement whieh comprises
eonverting the reactive dyestuff, before applieation, in an aqueous
medium by treatment with an alkaline agent from the non-fiber-
reactive to the fiber-reactive vinylsulfone form and chemically
stabilizing it in this eonverted form by adjusting to a neutral
to aeidie pH range by adding acid to the alkaline dyestuff solution,
and subsequently applying the dyestuff formulation thus obtained
to t.he fiber material from an aqueous, neutral to aeidie medium
by exhaust dyeing, pad-dyeing or printing, and fixing the dyestuff
on the fiber.
More particularly this invention provides a liquid re-
active dyestuff formulation capable of being infinitely diluted
with water and suitable for carrying out the process as claimed
in elaim 1, in whieh a dyestuff of eommereial eons-titu-tion is
present in a form ineapable of reaeting on its own with the fiber
substanee and eontaining reaetive groups being derived from esters
~0 of mono- or polyvalent, inorganie or organic acids easily split
of:E, with a~ -hydroxy-ethylsulfone compound, the reactive dyestuff
having been converted in an aqueous medium by treatment with an
alkaline agent from the non-fiber-reaetive to the fiber-reaetive
vinylsulfone form and having been ehemieally stabilized in this
eonverted form by adjusting to a neutral to acidic pH range by
adding acid to the alkaline dyestuff solution.
Suitable colouring agents which can be used aceording to
" - 4a -
., ~, j; ~

the principle of the invention are especially the conversion
products of those sulfonyl type reactive dyestuffs with which the
fiber reacts according to an addition mechanism via the vinyl-
sulfone (VS) form of the dyestuff, above all dyestuffs on the
basis of esters of
. ~ - 4b -

60~
- 5 - HOE 81~F 'l39
mono- or po]yvalent/ inorganic or organic acids ~.~hich
can be easi].y split off~ with B^-hydroxyethylsu].fone com-
pounds.
By the e~ample of the sulfuric acid esters vf
5 B-hydro~y2thylsulfone dyestu~-'fs (sulfatoe~hylsulfone
dyestufs), that is, the most important and most ~idely
used comrnercial form of this type o~ reactive dyes, the
Eormulations prepared in accordance with the invention
- and the correspondincJ clyeing processes for textil.es
- 10 containing or co~sistinc~ of cellulose are explained in
detail as follows:
For earrying out the process of the invention the
Estcr dyestuE~s are first dissolved in water. Subsequently,
an alkaline agent is added to the concentrated dyestuff
15 solution so obtained or a dyestuff solution diluted previ-
ously to the intended concentration, in order -to split
the ester grouping within the sul~atoethylsu].fone radieal
ancl to convert the latter one to the directly Eiber--
reaetive vinylsulfone radieal. This is carried out at a
20 tcmperature of from room temperature to boiling tempera~-
ture, preferably 25 to 60C, and .in the alkaline ranye,
pref'erably at a pH o above ~10. ~s alkaline agen-ts, aquoues
~olutions of alka].i metal hydroxides and/or salts havincJ
an alkal.ine reaction in ~later, such as sodium carbonate,
25 sodium hydroxic~e solu~i.on, water glass, trisodium phospha-te
etc. may be llsed. Dependinc3 on the temperature, the chemical
nature of the a].kaline ac~ent and the amount thereof, the
trea-tr[lent period or dyestuff conversion to the VS form
is from 10 seconds to 'l0 minutes~ Subsequently, the
30 alkaline liquor so handled is acidified and adjusted to
a pH o-E from 7 to about 3, preferably 6.5 to 5, for
chernical stabilization of the VS forrn obtained. Acidificatior
is erlsured by addi-~ion of a mineral acid, for exam~le
hydroc'l].oric, sulfuric or phosp]-loric aci~, or an orcJ.Inic
35 acid, for cxample rormic or acetic ac:id, to ~he a].kialine

-~8&~
- 6 - HOE ~1/F 139
dyestuff solution. If adjusted to the intended dyestuff
concentration alre.~ady prior to t~1e treatment ~7ith alkali.s
the dyestuff formulation so prepared now can be direct1.y
used for the dyeing or printlng of the tex-ti]e material.
Padding is preferably carried out at room temperature.
For reasons of a rational operation mode,
preponderantly such ,olutions of the Ester clyes-tuff
obtained in a concentrated form are treated with the
alkaline agent, and after acidification only diluted
with water to the intended concentration for the dyeing
or padding bath or.the printing p~s~.e. It is recommended
to check the pH after dilution once more and to correct
it if necessary. It is, however, not required to prepare
the concentrated dyestuff formulations immediately before
dyeing, padding or printin~; they can be made for stock
and are stable to stora~e for a prolonged time in the
form of "liquid dyestuffs" or printing pastes. By
evaporation, optionally to dryness, the concentra-Lion
of such a dyestuff formulation can be increased according
to the requiremen-ts of the practice.
For use in continuous processes where ]iqllor
concentration and liquor volume have to be mai.ntained
constant by steady feedin~-up addition, produc-tion o
the spontaneous].y reactive VS form from the Est:er dyestuf
by treatmen-t with alkalis in accordance with the :invention
can also be performed automatically by simply dosing and
mi~ing the con~lerci.al dyes-tuff solu-tion and the a1kali.ne
agent, while, however,taking into consideration a certair
residence time. Subsequently, by means of a second dosage
device acidification of the dyeing medium directly intro--
duced into the applicati.on operation can be realizecl in
dependence on a predetermined, weal~]y acid:ic pH.
In view of a simplified applicability, i.t has
proved to be advantageous that in the~ liqui.d formulacions
oiÇ the inventiorl the solubility ir. ~7ater of the vinyl-

~ ~ & ~ ~ ~6
- ,7 - ~O~ 81/~ 1~9
suIfone dyestu~fs, which before had been present already
in ti1e form of dissolved sulfatoethylsulfone dyestl1ffs,
is greater than in tl1e case where pulverulellt vinyl-
sulfone dyestuffs are ciirectly u.sed for preparing
5 such a soluti,on. This is of practical. importance in
the case of formuIations where due -to a hiyh concentration
and poor solubility crystallized dyest~lff has set-tled on
storage,.and this precipitate must be redissolved on
dilution.
In the speci.al dyeing and printing techni.qlles
described as follows in order to illustrate the utilization,
the dyestuff formul.ations obtained i.n accordance witn the
invention are used iIl the acidic range at a pH of prefer-
ably from 5 to 6.5. In an acidic medium, the hydrolysis
rate is relativel,y low, so that less hydrolyzed dyestuff
is formed; thus avoiding the formation of a large amount
of inactive hydroxyethylsulfone dyestuff from the vinyl~
sulfone form, which cannot react any more with the fiber
and is therefore los-t.
According to the exhaust method, cellulose fi.bers
are dyed in accordance with the inventi.or1 with the
dyestuff formulati.ons in thP acidic rangc; the d~7einy
being carried out wi.th:in 15 to 1~0 minutes at a tempe-
rature of from 20 to 140C.
As compared to tl1e exhaust- dyeiny with reactive
dyes in an alkaline medium usual in the industrlal
practice, the novel process has the fo~.lo-~ing advantages:
~ Mixed fabrics can be dyed in one single bath.
For exaople, these special reactive dyestuff for~nul.ations
can be used together t~ith disperse dyes in an acidic
bath for the dyeing of mixtures of polyester fibers and
cotton. E'urthermore, mi.xed fabrics of natura] or
synthetic polyarnide fibers and cellulose fiber.s can
jointly be 'created ~ith these reactlve dye fo:rmulations;
3~ both fiber types he:in~ dyed si.mll.1,taneously in thi.s case.

~ ,8 - - HOE_81/E 139
- Due to the fact that in accordance with the :inven-
t:ion nearly no inactive B-h~droxyethyl.su1.forle dyestuff i.s
formed, there are no dyestuff l,osses.
- Moreover, due to the improved dyestuff utiliz.ation,
5 less waste water polluti.on occurs.
As compared to the known exhaust dyeing of cel],ulosf
fibers with reactive dyes in an acidic medium rnentioned
above, the novel process brings about increased dye-
stuff yields and likewise less waste water pollution.
In the conti.nuous dyeing processes such as padding
and printing, the reactive dye formulati.ons obtained are
applied to the cellulose fiber material also in the
acidic pH range. The dyestuff is fixed subsequently by
steaming or dry heat trea-tment. Preferably, such a heat
fixation directly after padding or printing is effec-ted
upon the moist goods. Alternativëly, the padded or printed
fiber material can be subjected to an intermediate dry.ing
at a tempera.ture around 100C after the appl,ication step
of the dyestuff.
The dry hea-t treatment is carried out within 30
seconds to 10 mlnutes, preferably 2 to 5 mi,nutes, at a
temperature of from 120C to 240C, preferably 150 to
200C. Stearning or high temperature steaml,ng ls carried
out withi.n 30 seconds to 30 minutes at 100 to 240C.
Preferred is high temperature steaming, for example for
5 m.inutes a~ 183C. A saturated steam atmosphere is not
absolutely required. Good results ace for e~ample obta,inef.
when the moisture in the steaming apparatus is abou.t 90 %
of the satu.ration arnount present at the correspvndi.ng
temperature.
The adva.ntages of the i.nvention l.isted above in the
detai].ed description of the e~haust processes in compa-cison
witll the state of the art are identical when com~ar.ing
continuous dyeing processes. In addition tl~ereto, no
prohlems arise in the nove]. process with respe~t to t}1e

- ~ - HOE 81/F 139
stabillty of alkali.ne pac1ding liquors and persisten-t
soil.incJ oE the foulard rol.ls by alkali.ne agents such as
water glass. When the reactive dye formuIations accordlncJ
to the invention are used for pri.nting, the durabili-ty
of the printing pastes is prolonged as compared to those
used in kno~n one-phase printing processes. Furthermore,
the addition oE alkali donors may be renounced in one-
phase printlng processes.
As in the ~nown processes, the dyestuff yield of
the process of the invention can be improved hy increasincJ
the dyestuff substantivi-ty, ~or e~ample by ~ddition of
electroly-tes.
The followincJ E~amples illustrate the inventi.on. The
percentages are by wei~ht unless otherwi.se stated, and
relati.ve to the wei.ght of the dry goods in the case of
textile material.
E X M P L E
500 cm3 of boiling water are poured over 100 g of
the reactive dyestuff oE the formu]a
/ / S02-NI~-C 3 -S2 C~2 -2 3 -- 2
CuPc
/ S031-~_72
which is dissolvec~ in the water. AEter cooli.ng~ 20 cm3
of a 32.5 '~ sodium hydrox:ide solution are added to thjs
dyestuff solvt;on, the batch is stirred for 1 further
minute , and then acidified with acetic acicl to a pH
of 5.5.
100 cm3 are drawn off from the formu].aL-iol1 so
obtairled and fil.!ed u~ witn cold water unti] L^1 licluGr

- 10 -- HOE 81/F 139
volume of -I liter is attained. After addition of 1 g/l
of a commerclal wet-ting ayent~ a cotton fabric is padded
with tl1is liquor at a liquor uptake of 70'%. SubsequentJy,
t7ne padded fab~ic is steamed for 5 minutes at 150C in
order to fix the dyestuff; a mois-ture of 95 % of the satura-
tion amount being predetermined in the steamlncJ apparatus.
After steaming, the dyed t,extile material is first
rinsed with hot alld cold water, and subsecluen-tly soaped
at boiling temperature for 10 minll-tes in an aqueous bath
containing 1 g/l of a nonionic detergent. A turquoise-blue
dyeing having the fastnesses which are characteristic
for this dyestuff is obtained.
-E X A M P L E 2
50 g of the dyestuff Reactive Orange 16, C.I. No.
17757 are dissolved in 200 cm3 of boiling water, and then
diluted by adding further 800 cr~!3 of warm water. The
solution havin~ a temperature of about 60C is then
adjusted to pH 10 by means of sodium carbonate, and the
t~mperature is maintained for a further 10 minutes.
Su~sequently, the batch is acidified by means of hydro-
chloric acid unti] a pEI'of 6 7,1as adjus-ted. 7~efore paddincJ,
3 c~ of a commercia] we-ttiny agen~ are aclded.
The further treatInent for paddirlg of the goods is
as described in Example 1. A deep orange dyeing having
the fastnesses cl1aractel-istic for this clyestuffs is obtained.
.
E X_A'M P L E _3
'30 20 g of the dyestuff described in Ex~mple 1 are
formulated as indicated in Exarnple 2. After addlt:ion of
2 g of a corn7rlercial ~7ettiny agent, â cotton fabrjc is
paddrc'd with the padding :Liquor so prepared at a liquor
uptake of 75'~, The paddecl fabric is f:irs-t dried at
3~ 90 -- 100~C, and then the clyestuff fixation on thF' fib--7x

- 11 - . HOE ~1/F 139
is completed by a hot ai.r treatment at 200C for 3
minutes.
Subsequently~ the pad-dyed ce].lulose material is
rlnsed with hot and cold water and then soaped for 10
minutes at boiling temperature. Z~ turquoise-blue dyeing
having the fastnesses characteristic for this dyestuff
is obtained.
E X A M P L E 4
2 g of the dyestuff Reactive Blue 19, C.I. No. ~1200
are dissolved in 50 cm3 of hot water, and cold water is
added until a liquor volume of 1 liter is atta.ined. The
dyestuff solut.ion is then adjusted at pH 11 by means of
sodium hydroxide solution, and af-ter dwelling for 1 minute
under these conditions acetic acid is added to the batch
until a pH of 6.4 is attained in the liquor.
After having added 80 g of sodium sulfate to the
dyei.ng bath so obtained, 100 g of mercerized cotton yarn
are dyed therewith in a pressure vessel for 1 hour a-t
130C wi.th exhaustion. Subsequently, the dyed texti.le
material is rinsed wi.th hot and cold water and soaped
at boiling temperature for 20 minu-tes in an aqueous liquor
containing 1 g/l of a nonioni.c deteryent. A. blue dyeing
i.s obtained.
F X A M P L E 5
-
50 g of the reactive dyestuff of the formula
CIl3
O2S ~ N - N - C - - C - CH3
C~2 ~ N
I C 3 \ /
Cl~2
SV3Na
~3 a

- .12 - HOE 81/F 139
are dissolved in ~0 cm3.of hot water, and diluted wi.th
cold water to 1 liter. 20 cm3 of sodium hydroxide
solution (32.5 ~ strength) are added to this dyestuEf
solution, ancl after 1 minute oE dwelllng the formulatlon
is neutralized by means of acetic acld, and adjustPd
to prl 6.5.
Uslng the l.lquor so obtained, fabrlcs of
a1 rnercerized co-tton and
b) spun rayon
are padded. Subse~uently, the padded fabrics are
treated ln both cases for dyestuff fixatlon as follows:
(I) for one part with hot air for 3 minutes at 180C,
and for the other part
(II) by s-team:ing for 5 minutes at 130C, the steam
amount being 95 % of the saturatlon amount
possible at this tempera-ture.
Subsequently, the dyeings are rinsed with hot and
co].d water, and soaped at boiling temperature for 10
minutes in an aqueous bath containing 1 g/l of a
nonionic detergent. Yellow dyei.ngs are obtained in both
cases.
Similar results in the corresponding shades are
obtained when according to the operation mode oE the
above Example 5 the dyestuffs indicated in the followlng
Examples 6 to 9 are used:
E ~ A M ~ L E 6
Reactlve dyestuff of the formula
O/li \
~ r N ~ N ~ N ~3
S03~1 So2-clI2-c~l2--oso3

6~6
- 13 - HOE ~1/F 139
......
E X A M P L E _7
Dyestuff Reactive Orange 16, C.I.-No. 17757.
.
E X A M P L E, 8
Dyestuff Reac-ti~e slue 19, C.I.~No. 61200.
E X A M P L E 9
Dyestuff Reactive Black 5, C.I.-No. 20205.
E X A M P L E 1V
30 g of the dyestuff of Example 7 are formulated
as described in Example 5. Two mixed fabrics of polyamide/
cotton and polyamide/spun rayon, respectively, are
padded wlth this liquor, and subsequently for dyestuff
fixation steamed for 5 minutes at 130C (90 % moisture
in the steaming apparatus). The dyeings are then rinsed
with hot and cold water, and soaped at 60C in an aqueous
bath containing 1 g/l of a nonionic detergent. Orange
dyeings are obtained; in each case both fiber components
o the mi.xed fabrics are dyed in identical shades.
.
F X A M P J, ~ 11
40 g of the reactive dyestuff of the formula
Cll3-CO~
~ ~ co~
3 ~ - SO3~1 SO2~CH2-CI-~2 OSO~
3o
are dissolved in 200 crn3 of hot water. After cooling,
1 0 cm3 of a 32.5 ~ sodium hydroxide solution are added
to the dyestuff solution~ -the batch is al.lowed to dwell
for 1 minute, and is then neutralized wi.th the aid of
acetic acid, and adjusted -to pH 6.5.

;6
- 14 - ~lOE 81/F 139
.
The dyes'cuff formulation so prepared is then made
up to 1 kg of printing paste by adding water and a usual
thickener, and 50 g/~g of urea are added to the printing
paste. A cotton fabric is subsequently printed with
this paste, and the dyestuff is fixed by steaming for
5 minutes at 180C 198 % moisture in the steaming
apparatus). Subsequently, the textile material is rinsed
with hot and cold water, and soaped at boiling tempera-
ture for 15 minutes in an aqueous liquor containing
1 g/l of a nonionic detergent. A red print on the fabric
is obtained.
.
E X A M P L E 12
50 g of the dyestuEf Reactive Blue 19, C.I. No.
61200 are formulated as descrihed in Example 5. 40 g of
the dyes-tuff D sperse Yellow 64, C.I. No. 47023 and
2 g of a commercial wetting agent are added to this
dyestuff liquor.
A mixed fabric of polyester/cotton ~mixing ratio
67/33) is padded with this padding liquor. ThereaEter,
the fabric is steamed for 4 minutes at 150~C (95 % of
moisture in the steaming apparatus) for fixation of
the two dyestuffs. Subsequently, the goods so dyed are
rins~d with hot and cold water, and soaped Eor 10 minu-tes
at 70~C in an aqueous bath containing 2 g/l of a
nonionic detergent. A bicolor dyeing is ob-tained on the
mixed fabric; the polyester fiber portion being dyed
yellow and the cotton portion being dyed blue.
E X A 2`i P L E 13
30 C3 oE the dyestuff accordin~3 to Example 11 are
disso]vecl in 200 cm3 of boiling water, and diluted by
adding 800 cm3 of cold water. 5 cm3 of a 32.5 % sodium
hydroxide solution are added to this dyestuff solution,
and the batch is treated for 1 minute with stirring. The

;~&~5~
- 15 - HOE 81/F 139
formulation is then neutralized by means of acetic acid,
ancl adjusted to p~-~ 6.5.
After addition of 2 g/l of a commercial wetting
ayent and 15 g/l of sodium acetate, a cotton fabric is
padded with thi.s padding liquor at a liquor uptake of
70 ~. Subsequently, the padded fabric is steamed for
5 minu'ces at 120C in order to fix the dyestuff; a
moisture of ~8 % of the saturation amount bei.ng adjusted
in the steamlng apparatus. ~fter steaming, the dyed
goods are first rinsed with hot and cold water, and
then soaped at boiling temperature for 10 minute~ in
an aqueous liquor containiny I g of nonionic detergent.
A red dyeing having the fastnesses characteristic for
this dyestuff is obtained.
.. .
E X ~ M P L E 1~
30 g of the dyestuff accordiny to Example 2 are
prepared as described in Example 13, and applied onto
a cotton fabric. For dyestuff fixation, the padded fabric
is then steamed for 20 minutes in sa-lurated steam of
100C, the dyeing so obtained is then rinsed witll hot
and cold water, and subsequently soaped at boiling
temperature. An oranye dyei.ng haviny the fas-tnesses
characteristic or this dyestuff is obtained.

Representative Drawing

Sorry, the representative drawing for patent document number 1186456 was not found.

Administrative Status

2024-08-01:As part of the Next Generation Patents (NGP) transition, the Canadian Patents Database (CPD) now contains a more detailed Event History, which replicates the Event Log of our new back-office solution.

Please note that "Inactive:" events refers to events no longer in use in our new back-office solution.

For a clearer understanding of the status of the application/patent presented on this page, the site Disclaimer , as well as the definitions for Patent , Event History , Maintenance Fee  and Payment History  should be consulted.

Event History

Description Date
Inactive: IPC from MCD 2006-03-11
Inactive: IPC from MCD 2006-03-11
Inactive: Expired (old Act Patent) latest possible expiry date 2002-06-04
Inactive: Reversal of expired status 2002-05-08
Inactive: Expired (old Act Patent) latest possible expiry date 2002-05-07
Grant by Issuance 1985-05-07

Abandonment History

There is no abandonment history.

Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
HOECHST AKTIENGESELLSCHAFT
Past Owners on Record
FRANZ SCHON
SIEGFRIED GLANDER
Past Owners that do not appear in the "Owners on Record" listing will appear in other documentation within the application.
Documents

To view selected files, please enter reCAPTCHA code :



To view images, click a link in the Document Description column. To download the documents, select one or more checkboxes in the first column and then click the "Download Selected in PDF format (Zip Archive)" or the "Download Selected as Single PDF" button.

List of published and non-published patent-specific documents on the CPD .

If you have any difficulty accessing content, you can call the Client Service Centre at 1-866-997-1936 or send them an e-mail at CIPO Client Service Centre.


Document
Description 
Date
(yyyy-mm-dd) 
Number of pages   Size of Image (KB) 
Abstract 1993-06-09 1 30
Claims 1993-06-09 3 83
Cover Page 1993-06-09 1 20
Drawings 1993-06-09 1 8
Descriptions 1993-06-09 16 582