U.S. patent application number 10/570473 was filed with the patent office on 2007-01-04 for process for printing or dyeing cellulose/polyester mixed fibres.
Invention is credited to Veronique Hall-Goulle, Athanassios Tzikas.
Application Number | 20070000076 10/570473 |
Document ID | / |
Family ID | 34259308 |
Filed Date | 2007-01-04 |
United States Patent
Application |
20070000076 |
Kind Code |
A1 |
Hall-Goulle; Veronique ; et
al. |
January 4, 2007 |
Process for printing or dyeing cellulose/polyester mixed fibres
Abstract
The invention relates to a process for printing or dyeing
cellulose fibres or cellulose/polyester mixed fibres characterised
in that the fibres are treated in any sequence with water, a
watersoluble organic solvent having a boiling point >150.degree.
C. and a specific disperse dye.
Inventors: |
Hall-Goulle; Veronique;
(Dornach, CH) ; Tzikas; Athanassios; (Prattein,
CH) |
Correspondence
Address: |
CIBA SPECIALTY CHEMICALS CORPORATION;PATENT DEPARTMENT
540 WHITE PLAINS RD
P O BOX 2005
TARRYTOWN
NY
10591-9005
US
|
Family ID: |
34259308 |
Appl. No.: |
10/570473 |
Filed: |
August 30, 2004 |
PCT Filed: |
August 30, 2004 |
PCT NO: |
PCT/EP04/51952 |
371 Date: |
March 1, 2006 |
Current U.S.
Class: |
8/636 |
Current CPC
Class: |
D06P 1/613 20130101;
D06P 1/6138 20130101; D06P 3/8223 20130101; D06P 3/82 20130101;
D06P 3/60 20130101; D06P 3/8233 20130101; D06P 1/908 20130101 |
Class at
Publication: |
008/636 |
International
Class: |
D06P 1/00 20060101
D06P001/00 |
Foreign Application Data
Date |
Code |
Application Number |
Sep 8, 2003 |
EP |
03405656.4 |
Claims
1. A process for printing or dyeing cellulose fibres or
cellulose/polyester mixed fibres characterised in that the fibres
are treated in any sequence with water, a water-soluble organic
solvent having a boiling point>150.degree. C. and a disperse dye
selected from the compounds of formulae (1) to (10) ##STR25##
wherein R.sub.1 and R.sub.2 are each independently of the other
C.sub.1-C.sub.8-alkyl,
--(CH.sub.2).sub.n--O--(CH.sub.2).sub.mR.sub.5, wherein R.sub.5
denotes hydrogen or C.sub.1-C.sub.8-alkyl, n is a number from 2 to
6 and m is a number from 0 to 6, C aryl, which is unsubstituted or
substituted with one or more hydroxy groups, C.sub.1-C.sub.8alkyl
groups, C.sub.1-C.sub.4alkoxy groups or halogen atoms or
C.sub.6-C.sub.30aralkyl, which is unsubstituted or substituted with
one or more hydroxy groups, C.sub.1-C.sub.4alkyl groups,
C.sub.1-C.sub.4alkoxy groups or halogen atoms, R.sub.3 and R.sub.4
are each independently of the other chlorine, bromine, cyano,
methyl or trifluoromethyl, X is a radical of formula (1a), (1b),
(1c) or (1d) ##STR26## wherein R.sub.6 and R.sub.7 independently of
the other represent hydrogen, chlorine, bromine or cyano, R.sub.8
denotes C.sub.1-C.sub.8-alkyl or
--(CH.sub.2).sub.n--O--(CH.sub.2).sub.mR.sub.5, wherein R.sub.5
denotes hydrogen or C.sub.1-C.sub.8-alkyl, n is a number from 2 to
6 and m is a number from 0 to 6, R.sub.9 is hydrogen, fluorine,
chlorine, bromine, cyano, methyl, trifluoromethyl or
--SO.sub.2CH.sub.3 and R.sub.10 represents hydrogen, hydroxy or
amino; ##STR27## wherein R.sub.11, denotes a radical of formula
(2a), (2b), (2c) or (2d) ##STR28## wherein R.sub.17 is hydrogen,
chlorine, bromine, methyl or methoxy, R.sub.18 is hydrogen,
phenylamino, benzamido or C.sub.1-C.sub.12acylamido, one of the
radicals R.sub.12, R.sub.13 and R.sub.14 denotes a radical of
formula (2a), (2b), (2c) or (2d) as defined above and the others
are hydrogen, and R.sub.15 and R.sub.16 are each independently of
the other hydrogen, bromine or chlorine; ##STR29## wherein R.sub.19
denotes C.sub.1-C.sub.8alkyl or
--(CH.sub.2).sub.n--O--(CH.sub.2).sub.m--OR.sub.20, and R.sub.20 is
hydrogen, methyl or ethyl, n denotes a number from 2 to 6 and m
denotes a number from 0 to 6; ##STR30## wherein R.sub.21 is
C.sub.1-C.sub.8alkyl, C.sub.5-C.sub.24aryl, which is unsubstituted
or substituted with one or more hydroxy groups,
C.sub.1-C.sub.8alkyl groups, C.sub.1-C.sub.4alkoxy groups or
halogen atoms or C.sub.6-C.sub.30aralkyl, which is unsubstituted or
substituted with one or more hydroxy groups, C.sub.1-C.sub.4alkyl
groups, C.sub.1-C.sub.4alkoxy groups or halogen atoms; ##STR31##
wherein R.sub.22 and R.sub.23 are each independently of the other
hydrogen, bromine or chlorine; ##STR32## wherein R.sub.24 denotes
chlorine, bromine, cyano or --CONH.sub.2, R.sub.25 is
C.sub.1-C.sub.20alkyl or
--(CH.sub.2).sub.n--O--(CH.sub.2).sub.mR.sub.5, wherein R.sub.5
denotes hydrogen or C.sub.1-C.sub.8-alkyl, n is a number from 2 to
6 and m is a number from 0 to 6, D is a radical of formula (1c) as
defined above or a radical of formula (6a) ##STR33## wherein
R.sub.9, R.sub.10 and R.sub.25 are as defined above; ##STR34##
wherein R.sub.26 denotes C.sub.1-C.sub.12alkoxy; ##STR35## wherein
Me denotes Cu, Ni, Zn or Pd, R.sub.27 is hydrogen,
C.sub.1-C.sub.12alkoxy or --SO.sub.2--NH--R.sub.25 and R.sub.25 is
as defined above; ##STR36## wherein R.sub.28 and R.sub.29 are each
independently of the other a radical of formula (2b) or (2d) as
defined above; ##STR37## wherein R.sub.8 and R.sub.17 are as
defined above.
2. A process according to claim 1, characterised in that a compound
of formula (1) is used as disperse dye, wherein R.sub.3 is cyano
and R.sub.4 is methyl.
3. A process according to claim 2, characterised in that a compound
of formula (1) is used as disperse dye, wherein X is a radical of
formula (1a), (1b) or (1d).
4. A process according to claim 3, characterised in that the
disperse dye is a compound of formula (101) or (102) ##STR38##
5. A process according to claim 1, characterised in that the
organic solvent is polyethylene glycol, polypropylene glycol or an
ether or ester derivative of polyethylene glycol or polypropylene
glycol.
6. A process according to claim 5, characterised in that the
organic solvent is polyethylene glycol having a molecular weight of
100 to 600.
7. A process according to claim 1, characterised in that water,
organic solvent and disperse dye are contemporaneously applied to
the fibre.
8. A printing process according to claim 1, characterised in that
the printing paste contains 50 to 95% by weight of water, based on
the total weight of the printing paste.
9. A printing process according to claim 1, characterised in that
the printing paste contains 1 to 20% by weight of organic solvent,
based on the total weight of the printing paste.
10. A printing process according to claim 1, characterised in that
the printing paste contains 1 to 15% by weight of a dye dispersion,
based on the total weight of the printing paste.
11. A dyeing process according to claim 1, characterised in that
the fibres are heated in a liquor at 125.degree. C. to 225.degree.
C., said liquor containing as liquid ingredients 10 to 95% by
weight of water and 5 to 90% by weight of organic solvent.
12. A process according to claim 1, characterised in that the
fibres are cotton/polyester mixed fibres.
Description
[0001] The invention relates to a process for printing or dyeing
water swellable cellulose fibres or cellulose/polyester mixed
fibres with specific disperse dyes.
[0002] Many attempts have been made to develop efficient processes
for printing or dyeing polyester-cotton blends.
[0003] Two fundamentally different approaches were taken:
[0004] Processes using one class of dye only and processes using
mixtures of two classes of dyes.
[0005] Usually reactive dyes or vat dyes are combined with disperse
dyes.
[0006] However, the use of such dye mixtures is associated with
several drawbacks and it is hardly possible to obtain the same
colour and depth on the two fibres by this method.
[0007] DE 1 811 796 describes a process for dyeing cellulose fibres
or blends of cellulose fibres and synthetic fibres with a single
disperse dye which process comprises contacting said cellulosic
material with water in sufficient amount to swell the cellulose, a
solution or dispersion of the dye and a high-boiling water-soluble
solvent in an amount sufficient to maintain swelling of the
cellulose if water is removed.
[0008] In J. Soc. Dyers Colour., 96, 347-354 (1980) specific
disperse dyes (Cellestren.RTM., supplied by BASF) in combination
with Glyezin.RTM. CD, a polyalkylene oxide derivative, are
recommended for application in the printing process described in DE
1 811 796. The prints on polyester-cotton blends obtained by this
process are described as exhibiting brilliant colours with the same
depth of colour on both fibres.
[0009] However, the Cellestren/Glyezin system does not meet the top
requirements with respect to light fastness and wash fastness.
[0010] It has now been found that the application of some specific
disperse dyes in the process disclosed in DE 1 811 796 yields
prints and dyeings on polyester-cotton blends having
extraordinarily good light fastness and wash fastness.
[0011] The present invention relates to a process for printing or
dyeing cellulose fibres or cellulose/polyester mixed fibres
characterised in that the fibres are treated in any sequence with
water, a water-soluble organic solvent having a boiling
point>150.degree. C. and a disperse dye selected from the
compounds of formulae (1) to (10) ##STR1## wherein R.sub.1, and
R.sub.2 are each independently of the other C.sub.1-C.sub.8-alkyl,
--(CH.sub.2).sub.n--O--(CH.sub.2).sub.mR.sub.5, wherein R.sub.5
denotes hydrogen or C.sub.1-C.sub.8-alkyl, n is a number from 2 to
6 and m is a number from 0 to 6, C.sub.5-C.sub.24aryl, which is
unsubstituted or substituted with one or more hydroxy groups,
C.sub.1-C.sub.8alkyl groups, C.sub.1-C.sub.4alkoxy groups or
halogen atoms or C.sub.6-C.sub.30aralkyl, which is unsubstituted or
substituted with one or more hydroxy groups, C.sub.1-C.sub.4alkyl
groups, C--C.sub.4alkoxy groups or halogen atoms, R.sub.3 and
R.sub.4 are each independently of the other chlorine, bromine,
cyano, methyl or trifluoromethyl, X is a radical of formula (1a),
(1b), (1c) or (1d) ##STR2## wherein R.sub.6 and R.sub.7
independently of the other represent hydrogen, chlorine, bromine or
cyano, R.sub.8 denotes C.sub.1-C.sub.8-alkyl or
--(CH.sub.2).sub.n--O--(CH.sub.2).sub.mR.sub.5, wherein R.sub.5
denotes hydrogen or C.sub.1-C.sub.8-alkyl, n is a number from 2 to
6 and m is a number from 0 to 6, R.sub.9 is hydrogen, fluorine,
chlorine, bromine, cyano, methyl, trifluoromethyl or
--SO.sub.2CH.sub.3 and R.sub.10 represents hydrogen, hydroxy or
amino; ##STR3## wherein R.sub.11, denotes a radical of formula
(2a), (2b), (2c) or (2d) ##STR4## wherein R.sub.17 is hydrogen,
chlorine, bromine, methyl or methoxy, R.sub.18 is hydrogen,
phenylamino, benzamido or C.sub.1-C.sub.12acylamido, one of the
radicals R.sub.12, R.sub.13 and R.sub.14 denotes a radical of
formula (2a), (2b), (2c) or (2d) as defined above and the others
are hydrogen, and R.sub.15 and R.sub.16 are each independently of
the other hydrogen, bromine or chlorine; ##STR5## wherein R.sub.19
denotes C.sub.1-C.sub.8alkyl or
--(CH.sub.2).sub.n--O--(CH.sub.2).sub.m--OR.sup.20, and R.sub.20 is
hydrogen, methyl or ethyl, n denotes a number from 2 to 6 and m
denotes a number from 0 to 6; ##STR6## wherein R.sub.21 is
C.sub.1-C.sub.8alkyl, C.sub.5-C.sub.24aryl, which is unsubstituted
or substituted with one or more hydroxy groups,
C.sub.1-C.sub.8alkyl groups, C.sub.1-C.sub.4alkoxy groups or
halogen atoms or C.sub.8-C.sub.30 aralkyl, which is unsubstituted
or substituted with one or more hydroxy groups,
C.sub.1-C.sub.4alkyl groups, C.sub.1-C.sub.4alkoxy groups or
halogen atoms; ##STR7## wherein R.sub.22 and R.sub.23 are each
independently of the other hydrogen, bromine or chlorine; ##STR8##
wherein R.sub.24 denotes chlorine, bromine, cyano or --CONH.sub.2,
R.sub.25 is C.sub.1-C.sub.20alkyl or
--(CH.sub.2).sub.n--O--(CH.sub.2).sub.mR.sub.5, wherein R.sub.5
denotes hydrogen or C.sub.1-C.sub.8-alkyl, n is a number from 2 to
6 and m is a number from 0 to 6, D is a radical of formula (1c) as
defined above or a radical of formula (6a) ##STR9## wherein
R.sub.9, R.sub.10 and R.sub.25 are as defined above; ##STR10##
wherein R.sub.26 denotes C.sub.1-C.sub.12alkoxy; ##STR11## wherein
Me denotes Ni, Zn, Pd or preferably Cu, R.sub.27 is hydrogen,
C.sub.1-C.sub.12alkoxy or --SO.sub.2--NH--R.sub.25 and R.sub.25 is
as defined above; ##STR12## wherein R.sub.26 and R.sub.29 are each
independently of the other a radical of formula (2b) or (2d) as
defined above; ##STR13## wherein R.sub.8 and R.sub.17 are as
defined above.
[0012] The compounds of formulae (1) to (10) are known and either
commercially available or can be prepared according to known
processes.
[0013] Preferred compounds of formula (1) are those wherein R.sub.3
is cyano and R.sub.4 is methyl.
[0014] In a preferred embodiment of the invention a compound of
formula (1) is used as disperse dye, wherein R.sub.3 is cyano,
R.sub.4 is methyl and X is a radical of formula (1a), (1b) or
(1d).
[0015] Particularly preferred disperse dyes are the compounds of
formula (1), wherein R.sub.3 is cyano, R.sub.4 is methyl and X is a
radical of formula (1d).
[0016] Further preferred disperse dyes are the following compounds:
##STR14## ##STR15## ##STR16## ##STR17## ##STR18## ##STR19##
##STR20## ##STR21## ##STR22## ##STR23## ##STR24##
[0017] Particularly preferred disperse dyes are the compounds of
formulae (101), (102), (108), (109), (110), (115), (116), (118),
(119), (120), (124), (133), (141), (143), (144), (152) and
(154).
[0018] The most preferred disperse dyes are the compounds of
formula (101) and (102)
[0019] All the embodiments described in DE 1 811 796, hereby
incorporated by reference, can basically be performed by using the
disperse dyes of formula (1) to (10).
[0020] The organic solvent used in the process according to the
invention should be water-soluble and have a high dissolving
capacity for the disperse dyes of formulae (1) to (10) at the
fixation temperature.
[0021] Water-soluble in this context means solubility in water of
at least 2.5% by weight at 25.degree. C.
[0022] Suitable solvents of this type are glycols and their
derivatives, in particular the ethers and esters.
[0023] The preferred organic solvents that can be applied in the
process according to the invention are polyethylene glycol,
polypropylene glycol or an ether or ester derivative of
polyethylene glycol or polypropylene glycol.
[0024] Polyethylene glycol having a molecular weight of 100 to 600
is particularly preferred.
[0025] In dyeing cellulosic materials by the process of the
invention, water, dye and solvent can be applied to the substrate
in any sequence. The preferred method for dyeing fabrics composed
of cellulosic fibres or mixtures of cellulosic and synthetic fibres
is to impregnate the fabric with a mixture of one or more dyes,
water and solvent in a conventional dye pad bath followed by
squeezing to remove excess dye liquor, or to print with a
solvent-containing printing paste, and subsequently heating to
evaporate sufficient water to effect dissolution of the dye, at
which lime the fabric is dyed. Alternatively, water is evaporated,
but in an insufficient amount to effect dissolution of the dye,
after which pressure and heat are applied to effect dissolution
without further evaporation of water. Dye pastes can be prepared by
conventional techniques such as by milling the dye in the presence
of a dispersing agent or surfactant. A dyebath can be prepared by
diluting the dye paste with water or with aqueous solvent. Addition
of a solvent to the dye paste before addition of water may cause
dye separation and usually is avoided. It will be understood by
those skilled in the art that conventional additives other than a
dye solvent and a dispersing agent can be present in dye baths and
printing pastes.
[0026] Further components which may be present in the printing
pastes or dye baths are e.g. natural or synthetic thickeners,
pigments, acids, bases and/or salts to adjust the pH to the desired
value, anionic, nonionic or cationic surfactants, antifoaming and
antifrosting agents, dispersing agents, fixing agents, polyhydroxy
compounds, reaction products of hydroxyl compounds and isocyanates,
polyesters prepared by reaction of terephthalic acid and one or
more polyethylene glycols. These components are commonly used or
recommended for textile printing or finishing.
[0027] Although it is possible to treat the fibres in any sequence
with water, solvent and dye, the three components are preferably
contemporaneously applied to the fibre.
[0028] The relative amounts of water, solvent and dye that can be
applied in the printing pastes and dye baths are known to the
skilled artisan.
[0029] The printing paste which can be applied in the process
according to the invention preferably contains 50 to 95%, more
preferably 60 to 90% and in particular 70 to 85 by weight of water,
based on the total weight of the printing paste.
[0030] The amount of organic solvent is preferably 1 to 20%, more
preferably 2 to 15% and in particular 5 to 10 by weight of, based
on the total weight of the printing paste.
[0031] The amount of dye dispersion is preferably 1 to 15%, more
preferably 2 to 10% and in particular 3 to 8 by weight of, based on
the total weight of the printing paste.
[0032] The temperature at which dyeing or printing is effected by
the instant process depends on the solubility of the dye in the dye
solvent or aqueous dye solvent
[0033] Preferably, the fibres are heated in a liquor at 125.degree.
C. to 225.degree. C., said liquor containing as liquid ingredients
10 to 95% by weight of water and 5 to 90% by weight of organic
solvent.
[0034] The cellulosic materials which can be dyed by the process of
this invention include all forms of cellulose which increase in
size and flexibility upon exposure to water. Suitable materials
include natural fibres and purified wood pulps as well as
reconstituted cellulose in fiber and film form.
[0035] The invention is particularly useful for dyeing
cotton/polyester mixed fibres.
[0036] The following non-limitative Examples illustrate the
invention in more detail.
APPLICATION EXAMPLES
1. Dispersion
[0037] Each dye is dispersed according to the following
formulation: [0038] 29,2% dye [0039] 7.3% 1,2-propylenglykol
(solvent) [0040] 3.7% Lutensol AT25 (dispersant) [0041] 0.8%
Geropon T77 (wetting agent) [0042] 0.1% Surfinol DF58 (antifoam
agent) [0043] 0.4% Proxel GXL (antimicrobial) [0044] 58.5%
delonised water
[0045] Zirconium beads (diameter 0.6 to 1 mm) are then added to the
above-obtained dispersion in a glass bottle tightly closed. The
bottle is then placed in a Scandex apparatus and thereby agitated
for 4 hours.
[0046] The thus obtained fine dispersion is then filtered on a
conventional Buchner funnel to provide the final dye
dispersion.
2. Printing Paste
[0047] A typical run consists in the preparation of a mother paste,
to which a quantity of the dye dispersion and water will be
subsequently added.
Mother Paste:
[0048] 84.2% deionised water [0049] 0.8% NH.sub.4OH (28%) [0050]
0.4% Alcoprint PA-NS [0051] 9.9% PEG400 [0052] 2.3% Alcoprint PSC
[0053] 2.4% Alcoprint PTP Printing Paste [0054] 33.3% deionised
water [0055] 60.1% mother paste [0056] 6.6% dye dispersion
[0057] The amount of added deionised water can vary as a function
of the viscosity of the dye dispersion and/or of the printing
paste.
3. Printing
[0058] The printing paste is applied in a classical way on the
textile (CO or PES/CO) through a screen. After drying at 90.degree.
C., the textile is thermofixed at 220.degree. C. for 1 minute.
[0059] After a brief cold rinse, a 30 minutes wash at 80.degree. C.
is performed in a bath containing: [0060] 2g/L carbonate [0061] 1
g/L Calgon [0062] 1g/L Ultravon JU [0063] 4. Tests
[0064] All thus obtained printed fabrics exhibit a very good light
fastness, wash fastness and wet rubbing fastness.
* * * * *