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Patent 1040359 Summary

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(12) Patent: (11) CA 1040359
(21) Application Number: 208989
(54) English Title: PROCESS FOR THE PRINTING OR PAD-DYEING OF MIXED FABRICS
(54) French Title: METHODE D'IMPRESSION ET DE TEINTURE AU TAMPON SUR TEXTILES MIXTES
Status: Expired
Bibliographic Data
(52) Canadian Patent Classification (CPC):
  • 8/9
(51) International Patent Classification (IPC):
  • D06P 3/34 (2006.01)
  • D06P 1/00 (2006.01)
  • D06P 3/52 (2006.01)
  • D06P 3/60 (2006.01)
  • D06P 3/66 (2006.01)
  • D06P 3/82 (2006.01)
(72) Inventors :
  • SCHAUB, ANDRES (Not Available)
  • AESCHLIMANN, PETER (Not Available)
  • KOLLER, STEFAN (Not Available)
(73) Owners :
  • CIBA-GEIGY AG (Switzerland)
(71) Applicants :
(74) Agent:
(74) Associate agent:
(45) Issued: 1978-10-17
(22) Filed Date:
Availability of licence: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): No

(30) Application Priority Data: None

Abstracts

English Abstract




Process for the printing or pad-dyeing
of mixed fabrics
Abstract of the Disclosure
Described is a process for the tone-in-tone printing or
padding of mixed fabrics from cellulose materials and poly-
esters, wherein mixed fabrics are printed or padded with a
printing paste or padding liquor containing at least one
dyestuff of the formula
F - X - R1 - Y

wherein
F represents the radical of a disperse dyestuff free from
groups dissociating in water,
X represents an electron-attracting bridge-member,
R1 represents an ethylene radical which can be optionally
further substituted, and
Y represents the -OSO3H-group or the radical Image,
wherein R2 and R3 denote alkyl groups, different
from each other and containing 1 to 8 carbon atoms,
which together possess at least one water-solubilising
group,
subsequently dried, fixed and finished.
By this process there are obtained on mixed fabrics tone-in-tone
dyeings which are characterised by level shades and good
fastness properties, such as fastness to light, wet processing
and rubbing.


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. Process for the tone-in-tone printing or pad-dyeing of mixed fabrics
made from cellulose materials and polyester, wherein mixed fabrics are printed
and pad-dyed with a printing paste and dye liquor, respectively, containing
at least one dyestuff of formula I
F - X - R1 - Y (I)
wherein F represents the radical of a disperse dyestuff free from groups dis-
sociating in water, X represents an electron-attracting bridge-member, R1 re-
presents an ethylene radical which can be optionally further substituted by
alkyl having 1 to 4 carbon atoms, and Y represents the -OSO3H group or the
radical Image wherein R2 and R3 denote alkyl groups, different from each
other and containing 1 to 8 carbon atoms, which alkyl groups together possess
at least one water-solubilising group, and subsequently dried, fixed and
finished.

2. Process according to claim 1, wherein the printing paste or dye liquor
has a pH-value of 2 to 10.


3. Process according to claim 1, wherein the printing paste or dye liquor
contains dyestuffs of formula I in which F represents the radical of an azo
or anthraquinone dyestuff free from groups dissociating in water, X represents
an electron-attracting bridge member of the formula -NHCO-, -SO2-, Image
(wherein R4 denotes hydrogen or alkyl having 1 to 4 carbon atoms) or -OCO-,
R1 represents an ethylene radical which can be substituted by alkyl having 1
to 4 carbon atoms, and Y represents an Image radical, wherein R2 and R3
together contain at least one water-solubilising group of the formula -SO3H,
-OSO3H or -OPO3H .
19


4. Process according to claim 1, wherein the printing paste or dye
liquor contains dyestuffs of formula I in which X represents the bridge member
-NHCO-, -SO2- or -NHSO2-, R1 represents -CH2-CH2, and Y represents the OSO3H
group, or the radical of the formula Image , wherein R2 denotes an unsub-
stituted alkyl group having 1 to 4 carbon atoms, and R3 denotes an alkyl group
having 1 to 4 carbon atoms which is substituted by -SO3H.


5. Process according to claim 4, wherein R2 represents the -CH3 group,
and R3 represents the group -C2H4SO3H.


6. Process according to claim 1, wherein the fixing of the printing or
dyeing after drying is performed with steam or with dry heat.


7. Process according to claim 6, wherein the fixing of the printing or
dyeing after drying is performed with saturated steam under pressure.





Description

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



1040359
The invention relates to a ~-ocess for the printing
or pad-dyeing of mixed fabrics in tone-in-tone dyeings
with a single class of dyestuffs, to a printing paste
or dye liquor for carrying out this process, as well as
to the printed or dyed material as an industrial product.
The printing and dyeing of textile sheet material
made from mixtures of fibres belonging to various classes `
is becoming increasingly important, with special preference
being given to mixtures of polyester fibres with natural or
regenerated cellulose fibres, particularly viscose/cellulose. :
In the printing and dyeing of mixed fabrics with the
80-called "diffusing dyestuffs", the classes of dyestuff
to be applied to the respective substrates are, however,
always used mixed together or are combined 8uccessively.
The only procedure by which it is possible to produce
tone-in-tone dyeings on mixtures of fibres of natural origin
with polyester fibres by use of a single class of dyestuffs
is one such as is described, for example, in the Canadian
Patent Specification No. 832,343. This procedure requires,
however, the use of a large amount of a solvent or of a
swelling agent, a factor which leads to additional costs
and to considerable problems on account of the greatly
increased contamination of water and air.
It has now been found that mixed fabrics can be printed
or dyed tone-in-tone with a single class of dyestuffs, but -~



'




.'' . ' ` ' ' ` ' ` ' .. ' . . ``

104~359
with no necessi~y for the use of so].vents and swelling
agents, with which are connected so many disadvantages,
by a process wherein the mixed fabric is printed or pad-dyed with
a printing paste or dye liquor containing at least one
dyestuff of formula I
F - X - Rl - Y (I)
wherein
F represen~s the radical of a disperse dyestuff free
from groups dissociating in water,
X represents an electron-attracting bridge member,
Rl represents an ethylene radical which can be
optionally further substituted, and

Y represents the OS03H-group or the radical - N~ 2, wherein
R3
R2 and R3 denote alkyl groups, different from each
other and containing 1 to 8 carbon atoms, whlch alkyl groups
together possess at least one water-solubilising group,

and subsequently dried, fixed and finished.

The process according to the invention is characterised,
in particular, by the fact that it is possible to print or dye
mixed fabric tone-in-tone by use of only one type of dyestuff of
formula I, in that these dyestuffs contain a group that
can be split off under the fixing conditions, which group
contains at least one water-solubilising radical, so that
both the water-soluble dyestuff of formula I and the
water-insoluble disperse dyestuff formed therefrom are

~ 04~)355~
each absorbed as such on~o the corresponding material
in the mixed fabric.
This is effec~ed by subjecting the printed or pad-dyed and -
~dried mixed fabric to a fixing process, whereby the
5 fixing operation is performed, for example, at 120C
with steam and excess pressure, particularly for 20
minutes with saturated steam under pressure, or with
dry air at about 200C for about 30 seconds. It is also
possible, however, to perform the fixing process with
superheated steam for about 8 minutes at 160 to 200C.

The dyestuffs which are suitable for this process
correspond to formula I. In preferred dyestuf~s,
F represents the radical of an azo or anthraquinone
dyestuff free from groups dissociating in water,
X represents an electron-attracting bridge member of
the formulae -NHC0-, -S02-, -N-S02 (wherein R4 denotes

R4
hydr.ogen or alkyl having 1 to 4 carbon atoms) or -OC0-,
particularly, however, -NHC0-, -S02- or -NHS02 and
preferably -S02-,
Rl represents, in particular, an unsubstituted ethylene
radical, which can however be also further substituted
by ~lkyl having 1 to 4 carbon atoms, especially methyl,
and
Y represents a radical of the formula - N \ 2 or the

-0503H-r1dical, whorein R2 and R3 together contain




.
, ~. .. ,. . . , ~ . :

104~)359
at least one water-solubilising group of the
formula -S03H, -OS03H or -OP03H2, and wherein R2
represents an unsubstituted alkylgroup having 1 to 4 ~ .
carbon atoms, particularly the methyl group, and
R3 represents an alkyl group having 1 to 4 carbon
atoms which is substituted by these water-solubilising
groups, especially by the -S03H group; R3 preferably
represents the -C2H4S03H group.
All these dyestuffs are known and can be prepared
by known methods (see, for example, the Belgian Patent
Specifications Nos. 803,131, 813,216 and 813,217).
The printing paste or dye liquor employed contains,
in addition to the defined dyestuff of formula I or mixtures
thereof, which may be present in an amount of 5 to l5 g
per kg of printing paste or dye liquor, the usual
auxiliaries, such as, thickening agents, agents for improving
solubility and diffusion, such as urea, oxidising agents,
acids or alkalies and water. A thickening agent to be
mentioned in particular is an aqueous alginate thickening.
Suitable oxidising agents are aromatic nitroarylsulphonic
acids, such as the sodium salt of m-nitrobenzenesulphonic
acid, The pH-value of this printing paste or dye liquor can
vary within wide limits, and is between about pH 2 and 10.
Suitable mixed fabrics which can be printed or dyed
according to the invention are those made from cellulose




. - . ~ . . , . ............ , ~
,, ! , . ; ' . .
" ,, , , ' ' , . :

' 104V3Sg
fibres, s~ch a~ cotton or regenerated cellulose and
polyester fibres.
The mixed fabric can be in any desired form, such
as thread, knitwear, fabric or yarn.
The printing itself is performed on known machines,
such as on a cylinder printing machine, or on a screen
printing machine; and the pad-dyeing is carried out, for
example, on a padding machine.
After being printed or pad-dyed, the material is dried,
subjected to a fixing process, and subsequently finished
by rinsing.
By the process according to the invention, there are
obtained on mixed fabrics tone-in-tone dyeings which are
characterised by a uniform shade and by good fastness
lS properties, such as fastness to light, wet processing
and rubbing.
The following examples illustrate the invention without
in any way limiting its scope. Temperatures are expresséd
in degrees Centigrade.


lU4~)3S9
Example 1
A mixed fabric made from polyester fibres and cotton
fibres (67:33) is preliminarily treated, in the usual
manner for printing, and is then printed on a cylinder
printing machine with a printing paste having the
S following composition:
10 g of l:he dyestuff of the formula

NaO3SO - CH2CH2S2 ~ ~ ~ N 2 5
NHCOCH3

500 g of a 12% aqueous solution of sodium alginate,
50 g of urea,
50 g of a 10% aqueous solution of the sodium salt
of nitrobenzenesulphonic acid,
20 g of sodium bicarbonate and
370 g of wa~er
1000 g.
This printing is subsequently continuously dried at
about 100, and then fixed with saturated steam of 1.5 bars
for 20 minutes. For removal of the excess dyestuff, the
material is firstly rinsed cold, then soaped at 90 by
means of an aqueous solution containing per litre 2 g
of an anion-active ethoxylation product based on vegetable
oils, and again rinsed.
The result is a printing in an orange shade having
-- 7 --




,


1~)4~359
very good fastness properties in service, with both
types of fibre being dyed with the same depth of colour
and in the same shade.
If, instead of the dyestuff of the above formula,
S identical amounts of a dyestuff of the formula



NaO3SO - C~2 - CH2 S02NH ~ N = N ~ /C2H5


,
are used, with otherwise the same procedure, then a
gold-yellow printing is obtained, with likewise both
fibre constituents being dyed in the same shade and
depth of colour.

,

, ~
.




- 8 -




... .- . - . . . . . .
... .


Examp]e 2 1~40359
A mixed fabric made from polyester and regenerated
cellulose (50:50) is printed with the foIlowing printing
paste, and finished as described in Example 1:
10 g of the dyestuff of the formula

5~ ~ CH2~H2 - S02 ~ N = N ~ , CH3
CH CH -S03:Na C 3
2 2 NHCOCH3

500 g of a 12% aqueous solution of sodi.um alginate,
50 g of urea,
50 g of a 10%.aqueous solution of the sodium salt
of nitrobenzenesulphonic acid,
1035 g of trichloroacetic acid sodium, and
355 g of water
1000 g.
The~e i8 obtained a printing of orange shade having
very good fastness properties in service, with both fibre
constituents being dyed in the same shade and depth of colour.
If, instead of the dyestuff of the above formula,
there are used identical amounts of a dyestuff of the
formula o NH2
~ I
~ 2 02C2H40s03Na
g_ ,

.' , , , ,' ,''' ' ''~
1. ,

1~4S)359
or of ~he formula

O OH

) CH
O ~H ~ NHCOC~12CH2 - N
CH2CH2 -S3Na
with otherwise the same procedure, then a blue printing
is obtained.

.




- 10 - ' . '




.: ,

104~59
Example 3
A mixed fabric made from polyester and cotton
(50:50) is printed with the following printing.paste:
10 g of the dyestuff of the formula


3 ~2CH2s2 ~ - N = N ~ ,CH2 ~


S500 g of a 12% aqueous solution of sodium alginate,
50 g of urea,
5 g of sodium salt of nitrobenzenesulphonic acid,
35 g of trichloroacetic acid sodium and
400 g of water
101000 g.
The material is subsequently finished according to
the procedure described in Example 1.
There is obtained a printing of gold-yellow shade
having very good fastness properties in service, with
both fibre constituents being dyed in the same shade
and depth of colour.




- 1 1 - -
, '~, .



I . .. - . . .

1~4~3S9
Exampl e 4
A mixed fabric made from cotton and polyester (33:67)
is printed with the following printing paste:
10 g of the dyestuff of the formula

CH3S02~-- N = N~ ~ C H

Co-cH2-cH2-N-cH2-cH2-so3 Na
CH3
.
500 g of a 12% aqueous solution of sodium alginate,
50 g of urea,
10 g of citric acid,
5 g of sodium salt of nitrobenzenesulphonic acid,
425 g of water
.
1000 g. ' ~,
After being printed, the material is dried, and fixed
in dry air at 200 for 60 seconds. The unfixed portion .
of dyestuff is removed by cold rinsing in water, then : -
hot soaping at 60 using an aqueous solution containing
per litre 2 g of an anion-active ethoxylation product
based on vegetable oils, and ~inally again cold rinsing. ~-
Theré is obtained an orange-red printing of high purity
having very good fastness properties; both fibre
constituents are dyed in the same shade and depth of
colour. .

- 12 - . .




.


. .. . . . . .

~4V359
If, instead of the aforementioned dyestuff, there is
used 10 g of the dyestuff of the formula
Cl
CH3S02 ~ N = N ~ - N~ C H
N
CO
CH2




CH2
H3C ~H2C~12S03Na
,
and, in the above printing paste, 10 g of citric acid
is replaced by 10 g of water, and fixing is performed
for 20 minutes under saturated-steam conditions in a
8u8pension loop steamer, then there i8 obtained, with
otherwise the same procedure, a printing in a deep red
shade having very good fastness properties in service,
with both fibre constituents being dyed in the same shade
~nd depth of colour.




- 13 -


1~4V359
Example 5
A mixed fabric made from cotton and polyester ~33:67)
is printed.with the following printing paste: :~
10 g of the dyestuff of the formula

Nad3SOC2H4S02 ~ N - N ~ 3
(~

500 g of a 12% aqueous solution of sodiwn alginate,
50 g of urea,
10 g of citric acid, .
5 g of sodium salt of nitrobenzenesulphonic acid,
425 g of water
1000 g. ..
Subsequent to printing, the material is dried, and :.
fixed in dry air at 200 for 60 seconds. The unfixed .
portion of dyestuff is removed by cold rinsing in water,
then hot soaping at 60 using an.aqueous solution .:
containing per litre 2 g of an anion-active ethoxylation
prod~ct based on vegetable oils, and finally again cold ~
rinsing . ' '
There is obtained a yellow printing which is of high .
purity and which has very good fastness properties; both fibre
constituents are dyed in the same shade and depth of
colour.
- 14 - :




:, . .

, ~.. . ...... .. .. ... . .. . . . . .. .
. . .

1~4~;~S9
Example 6
A mixed knit~ed fabric made from cotton and
polyester (50:50) is printed with the following
printing paste:
10 g of the dyestuff of the formula



3 2 ~ ~ 2 5

Nll
co-cH2c~l2-N-c~l2cH2-so3Na
~3


500 g of a 12% aqueous solution of sodium alginate,
50 g of urea,
70 g of sodium salt of trichloroacetic acid,
5 g of sodium salt of nitrobenzenesulphonic acid and
10365 g of water
1000 g.
The finishing is subsequently performed as in Rxample 1.
There is obtained a printing of orange shade having
very good fastness properties in service, with both
fibre constituents being dyed in the same shade and
depth of colour.
If, instead of the dyestuff of the above formula,

identical amounts of a dyestuff of the formula
- OCH3


Na03sOc2~ s02 ~ N ~ N(C2HS)2
_
N ICOCH3
are used, with otherwise the same ~rocedure, then a red

printing is obtain~d.
- 15 -




:: , - - ..... ,
. . :
. . :


Examp1e 7 104V359
If, with the procedure otherwise as described in
Example 5, fixing is performed, not in dry air at 200
for 60 seconds, but by steaming at atmospheric pressure
in superheated steam at 180 for 5 minutes, then an
S equally well printed mixed fabrLc Ls obtained.



',' ... ..

~


Example 8 ~4V3~59
A mixed fabric made from polyester fibres and cotton
fibres (67:33) is impregnated on a padding machine at 25
with a liquor having the following composition:
15 g of the dyestuff of the formula


NaO35C)C2H4502~N = N~N~C2H5)2

NHCOCH2

200 g of a 2.5% aqueous solution of sodium alginate,
100 g o~ urea,
10 g of sodium bicarbonate,
5 g of borax, and
670 R of water
1000 g.
The fabric, squeezed out to about 100% liquor absorption,
is dried at 100 and subsequently fixed for 90 seconds
at 210. In order to remove the excess dyestuff, the material
is firstly rinsed cold, and then at 90 by means of an aqueous
solution containing per litre 2 g of an anion-active
ethoxylation product based on vegetable oils; it is
afterwards soaped and again rinsed cold.
A red dyeing having very good fastness properties in
service is obtained, with both fibre constituents being
dyed in the same shade and depth of-colour.
; .
- 17 - ~


,.~,..


10403S9
I~, instead of ~he dyes~uff of the above formula,
identical amounts of a dyestuff of the formula .

OH
NaO3SOC2H4CON~ ~ = N
CH3




are used, with otherwise the same procedure, then a
S yellow dyeing ls obtained.




- 18 -




... , , ~ - . :

Representative Drawing

Sorry, the representative drawing for patent document number 1040359 was not found.

Administrative Status

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 , Administrative Status , Maintenance Fee  and Payment History  should be consulted.

Administrative Status

Title Date
Forecasted Issue Date 1978-10-17
(45) Issued 1978-10-17
Expired 1995-10-17

Abandonment History

There is no abandonment history.

Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
CIBA-GEIGY AG
Past Owners on Record
None
Past Owners that do not appear in the "Owners on Record" listing will appear in other documentation within the application.
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Document
Description 
Date
(yyyy-mm-dd) 
Number of pages   Size of Image (KB) 
Drawings 1994-05-19 1 5
Claims 1994-05-19 2 57
Abstract 1994-05-19 1 30
Cover Page 1994-05-19 1 15
Description 1994-05-19 17 411