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Patent 2225380 Summary

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(12) Patent Application: (11) CA 2225380
(54) English Title: METHOD FOR DYEING MIXED FIBERS
(54) French Title: PROCEDE DE COLORATION D'UN MELANGE FIBREUX
Status: Dead
Bibliographic Data
(51) International Patent Classification (IPC):
  • D06P 3/872 (2006.01)
  • D06P 3/82 (2006.01)
(72) Inventors :
  • HIMENO, KIYOSHI (Japan)
  • SEKIOKA, RYOUICHI (Japan)
  • HIHARA, TOSHIO (Japan)
(73) Owners :
  • DYSTAR JAPAN LTD. (Japan)
(71) Applicants :
  • DYSTAR JAPAN LTD. (Japan)
(74) Agent: FETHERSTONHAUGH & CO.
(74) Associate agent:
(45) Issued:
(86) PCT Filing Date: 1996-06-20
(87) Open to Public Inspection: 1997-01-09
Availability of licence: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): Yes
(86) PCT Filing Number: PCT/JP1996/001712
(87) International Publication Number: WO1997/000996
(85) National Entry: 1997-12-19

(30) Application Priority Data:
Application No. Country/Territory Date
7-177996 Japan 1995-06-22

Abstracts

English Abstract




A fiber mixture containing cellulosic and polyester fibers is dyed with a
reactive dye at least 60 % of which is fixed to the cellulosic fibers at a pH
of 9.0 to 12.0 and a bath temperature of 50 to 85 ~C and an alkali-fast
disperse dye at least 90 % of which is fixed to the polyester fibers at a pH
of 8.0 to 11.0 and a bath temperature of 120 to 140 ~C.


French Abstract

On colore un mélange fibreux contenant des fibres cellulosiques et polyesters à l'aide d'un colorant réactif dont 60 % au moins se fixe aux fibres cellulosiques à un pH compris entre 9,0 et 12,0 et à une température de bain comprise entre 50 et 85 ·C et d'un colorant plastosoluble résistant à l'alcali dont 90 % au moins se fixe aux fibres polyesters à un pH compris entre 8,0 et 11,0 et à une température de bain comprise entre 120 et 140 ·C.

Claims

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





- 33 -
CLAIMS
1. A dyeing method characterized in that mixed fibers
comprising cellulose fibers and polyester fibers are dyed
in a single bath with a reactive dye at least 60% of
which is fixed to cellulose fibers at a pH value of from
9.0 to 12.0 at a bath temperature of from 50 to 85°C, and
with an alkali-resistant disperse dye at least 90% of
which is fixed to polyester fibers at a pH value of from
8.0 to 11.0 at a bath temperature of from 120 to 140°C.
2. The method according to Claim 1, wherein the reactive
dye has, as a reactive group, at least one selected from
the group consisting of a pyrimidine group having a
halogen atom, a triazine group having a halogen atom,
-SO2W wherein W is -CH=CH2 or -C2H4V (V is a group to be
eliminated by an alkali) and Image


3. The method according to Claim 1, wherein he reactive
dye has, as a reactive group, at least one selected from
the group consisting of a pyrimidine group having a
fluorine atom, triazine group having a fluorine atom, and
-SO2W wherein W is as defined above.
4. The method according to Claim 1 or 2, wherein dyeing
is conducted in the presence of 10 to 80 g/~ of an
electrolyte.
5. The method according to Claim 1 or 2, wherein at
least one selected from the group consisting of an alkali
metal hydroxide, an alkali metal carbonate, an alkali





- 34 -


metal hydrogen carbonate, an alkali metal phosphate and
an alkali metal silicate is used as an agent for
adjusting a pH value, in an amount of from 0.01 to 5 g/~
in the dye bath.
6. The method according to Claim 1 or 2, wherein the
weight ratio of polyester fibers to cellulose fibers in
mixed fibers comprising cellulose fibers and polyester
fibers is 20:80 to 80:20.





Description

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


~ CA 0222~380 1997-12-19

~ ~ . .

our Ref.: MH-14

DESCRIPTION
METHOD FOR DYEING MIXED FIBERS
TECHNICAL FIELD
The present invention relates to a method for dyeing
mixed fibers comprising cellulose fibers and polyester
fibers in a single bath.
BACKGROUN~-ART

~.-- When mixed fibers comprising cellulose fibers and
polyester fibers are dyed, they are usually dyed in two
baths having pH ranges different from each other. That
is, first, polyester fibers are dyed with a disperse dye
at a pH value of from 4 to 6 at a bath temperature of
frcm 120 to 140~C. After reduction cleaning, cellulose
fibers are then dyed with a reactive dye at a pH value of
from 12 to 14 at a bath temperature of from 50 to 90~C.
When using the above-mentioned dyeing method, it
usually takes 7 to 9 hours to dye a batch, and the
productivity is very low.

The present inventors have studied to provide a
method for dyeing mixed fibers comprising cellulose
fibers and polyester fibers in a single bath and in a
short time, and achieved the present invention.
DISCLOSURE OF THE INVENTION

The gist of the present invention resides in a method

for dyeing mixed fibers comprising cellulose fibers and
polyester fibers with a reactive dye and a disperse dye

CA 0222~380 1997-12-19



in a single bath, characterized in that said reactive dye
is a reactive dye at least 60~ of which is fixed to
cellulose fibers at a p~ value of from 9.0 to 12.0 at a
bath temperature of from 50 to 85~C, and that said
disperse dye is an alkali-resistant disperse dye 9o% of
which is fixed to polyester fibers at a pH value of from
8.0 to 11.0 at a bath temperature of from 120 to 140CC.
The present invention makes it possible to dye
; satisfactorily mixed fibers comprising cellulose fibers
and polyester fibers in a single bath, in one step, and
in a short time.
THE BEST MODE FOR CARRYING OUT TEE INVENTION
Hereafter, the present-invention will be explained in
detail.

15The reactive dye used in the present invention is a
dye having at least one selected from the group
consisting of a pyrimidine group having a halogen atom
mainly, a triazine group having a halogen atom, a
~ vinylsulfone type reactive group, and - CO ~ N ~ Cl



which have a suitable dyeing property in a range of weak
alkalescence, a high reactivity, and a high stability at
high temperatures.
Examples of the halogen atoms include a chlorine atom
and a fluorine atom, but a fluorine atom is more suitable
due to its high reactivity. Examples of the reactive dye

include the dyes represented by the following general


CA 02225380 1997-12-19

--. 3 --
formulas [A-l ] to [A-36 ] .

CH3 R6


N ~ Rs
A I ky I

R6 ~.6

~A - 3 ~ N~N ~A - 4 ]
R2




r.~ ,¢~ (A--5 3
N
Rs




~N~ ~D~ ~A- 6 )
R7--CO-NH NII--Z

~CH3 ~1--N SO3M
N--CH ~A--7~ N~NH2 ~A--83

O \ ~
D2 NH-Z

CA 02225380 1997-12-19




D3-N S 03M
N~NH2 ~A--9)
N H--Z

O H
\N~ ~NH-Z ~A--1O~
MO3S

.. OH o
- DI\N~N ~,~NH-C~--NH--z (A--1 1 MO3S

OH
D 2~ N~N~}NH-C O--R 10 ~A - 1 2 )
MO3S

O H
D ~ N~ N ~ 3}N H-C O - R 10 [A - 1 3
MO3S

( S 0 3M ) p

N~N~NH--Z (A- 1 4)
MO3S

(S 03M)p
\N ~N~ ~ ~A - 1 5

; CA 02225380 1997-12-19


.. ~ 5 --
H0 NH-Z
~N~ ~ ~A--16)
M03S S 03M


II 0 ~}NH- Z ~A- 1 7 )

M03S S 03M
.~.
o NH - 7:
A--1 8 )
M 0 3 S S o 3M


~0 HN~ ~Rl~
D 2~ N ~ N ' ,~ (A - 1 9 )
M03S S 03M

~I O ~IH2
D ~N~ N~N~N, D2 ~A--2 0
M03S S 03M

H0 N~2
N~ ,~ ,D ~A--2 1

M03S S 03M

H0 NH2
N~ ,--~ N~N~D3 ~- 2 2)
M03S S 03M

CA 02225380 1997-12-19


-- 6


H 0 ~H2
1) \N~N ~/N~I~D3 tA--2 3
hlO3S S 03M

H 0 NH2
1~ ~ N~ N '~,N~N, D3 (A--2 4 3

M03S S 03M
....

C I S 03M
~N~,o~NH-- (G--NA)r--Z

Z-- (AN--G)r--HN~0
S03M C 1 ~A--2 5

C I S O2-W
~'N~'o'~NH-- (G--~A)r--J

J - (A N - G) r- H N /~O ~ N~
S 0 2-W C l
tA--2
C I S O2-W
~Nq~ 0 ~, N H--W ~ A--2 7 )

W- HN~O~N~
S02-W C I

CA 02225380 1997-12-19




O NH2

,SO3M (A--28)
O HN~_(CH2)~-NA - Z

(S 03M)p

-- O Z
Il HN
M 0 3 S--~= \C/ ~ S o 3~L

N~ ~ M(~) ~A- 2 9 )




p~ (S 03M)a

~N~ ( s O zl\~ H2 ) b [A - 3 0

(S 03-N H~ NH - L
(S C3M)r c


OH (I~H-CO-RI~)r
N~ ~ ( S 03M)m ~A--3 1


OH (NH--Z)r
N~ ~ (SO3M)m ~A- 3 2 )

CA 02225380 1997-12-19


.-- 8 --
~,OH OH (NH--CO--Rl~)r

_~N~ N ~6 ( S 0 3~ ) ~ ~ A--3 3 )

(S 03M)o


OH OH (NH- 7:)r

(S 03M)s~ ~A--3 4

. .
,, ( S 0 3M)o


N~ ~OH OH (N~--CO--Rl~)r
Ra N~N'~ (S03M)~ ~A-3 5)


N~ ~,O H O H (~ H - Z )r
R3 N~N~ (S O3M)m [A--3 6)

CA 02225380 1997-12-19


_ ~ _
In the above formulas [A-l] to [A-36],
R8




Dl is ~ or (M 03S)o
(M 03S)~

Z - N A - (C H2)r
D2 is ~ or .~03S)o ~
(~ 03S)m (C H2)r-N A - Z

W02S
-.- 3 i ~ or (M 03S)o
R8 R8 S 02W

~ H O ~
D4 is Q ~ , (M 03S)o ~ ~ ~ , or
(M 03S)m

OH

(M03S)o b~


R2 R2
E is ~ R3 or ~ ~ R3
R4 R4
o




~ U~ ~N~C I r
A B

CA 0222~380 1997-12-19


--.. 10 --
X is F or Cl, Y is H or F, U is H or Cl, A is H, a
Cl_4 alkyl group, a phenyl group, or ~ (S O3M)r B i



H, a Cl_4 alkyl group or -(CH2)n-[O-~CH2)n]r-SO2W, or
5 ~ SO W (when Z is ~ ~ X , A and B constitute


R8 ,N~
A B
-C2H4OC2H4- and may form a heterocyclic ring together
~-~ with the nitrogen atom to which A and B are bonded.) W
is -CH=CH2 or -C2H4V (V is a group to be eliminated by an
alkali, preferably -OSO3M.) The alkyl group is a Cl_4
alkyl group which may be substituted by -SO3M, Rl is H,
-CONH2 or -CH2SO3M, each of R2, R3 is R4 is H, -SO3M,
-CH3, Cl or Br, R5 is -CH3 or -CO2M, R6 is -OH, R7 iS -CH3
or -NH2, each of R8 and R8' is H, -CH3 or -OCH3, R9 is H,
-NHCOCH3 or -NHCONH2, Rl0 is H, a Cl 4 alkyl group or a
phenyl group, M is H, Li, Na or K, G is a C2_4 alkylene
group, J is a -CO-Cl_4 alkyl group, a -CO-Cl_4
- alkylene-COOM or a benzoyl group, L is Z or D3, Mt is Cu
or Ni, Q is H, -SO3M, -SO2W or -(CH2)r-NA-Z, a is 1-3, b
is 0-2, c is l or 2, provided a+b+c = 2-4, m is l or 2, n
is 2 or 3, o is 1-3, p is
0-2, and r is 0 or l.
Z may be the group represented by the following

formula
X X




N ~ N-T-~ N
A A

CA 02225380 1997-12-19

,

, ~ 11 --

wherein T is a C2_8 straight or branched chain alkylene
group, (S 03M)r ~ (S03~)r
,C~
. (MO3S)r

S03M S03M
, ~ C H= C H ~ or

. S 03M SO3M
.. S 03M
~C2H
S03M
Examples of the reactive dye include the dyes
represented by the following formulas (1) to (33).


CO~H OH ~ Cl ~ N
~ N=N P (1)

H~3Sf~,So3H

HO3S HO3S~G~NH ~N~ NH~
H3C~N=N ~ N~,N ( 2 )
SO3H OH

~NH ~N~ NHCH2~
S03H N ~ N ~ SO3HS03H S03H (3)


OH ~HCO ~

CA 02225380 1997-12-19


.,
. 12 --

HzN OH SO3H
H33SOH4C202S~N=N~ rN=N~ ( 4 )
SO3~1 SO3H NH ~ ~7
CIJ~N
p




Cl CH3
~- NH ~ N~ NH -~ N=N ~ CONH2 ( 5 )
SO3H ~ SO3H HO N O
- F
. - C2H5

HO SO ,~


~ ~SD;H CH~

SO3H
,~ ~N=N~NH~N~NH~ ( 7 )
SO3H SO3H NHC31YH2 ~ C~3

~.,. ~-
SO3H HO


SO~H ~ ~ N ~ ( 8 )
SO3H N~, N CH
F




SO3H HO
H3CO ~ N=N ~

SO3~NH ~ N~ N~9 ( 9 )
N N
~ C2Hs

CA 02225380 l997-l2-l9


-..13 ~

SO3H HO NH ~N~NH~Ci - --
~N=N~SN3~N (10)

SO3H

SO3H
~,
~~C~
SO3H o=Cu "C~9 ( 11)
.: - ~ N1 NH - N
-' ~NH ~ ~ NH
N~, N ~J
F SO3H


SO 3H N ,~N~ O ~j, NHC3H 6NH ~ ~ NH ~S
~H~ ~HNH6C3HN O N ~Y SO3H
Sa3H ~ S33H C I F
(12)


SO3H O--Cu O
N=N~N=N ~
SO3H CH~ SO~N ~ ~ NH2 (13)
IH N~N

H2N OH
HO3S~N=N ~53~ ~ Cl

CA 02225380 l997-l2-l9


-.14 -

O--Cu O F


50'~503H~ ~


~ N~N~YH~ ~16)
SO~ NHCOCH 3 C

H03S O--Cu--O F
r- SOlh~503H H~N N (17)


SO3H OH

'NH ~ (18)
C


- P~N CH3 ~N ~SO3H (19)
, . N~ NH ~ N=N~ N
P C I CH3
SO3H

HO
F~N \~ ~ ~ ~SO3H (20)
N~ NH ~ ~ C I

SO3H

CA 02225380 1997-12-19


-- .15
O
HO3S ~ - N ~ ~ NH
~ N ~h S~===' o~ NH (21)
N ~ NH ~
F Cl SO3H

SO3H OH NH-CO
N=N ~
~ N ~ S ~ (22)
N ~ NHCH2 SO3H
F Cl

~ N OH NHCOC~3
N ~ 7-CH2 ~ N N ~ (23)
Cl CH3 SO3~ SO3
Sa3H

~ OH NHCO ~
N ~ N-CH2 ~ N=N ~ 'i~ (24)
F Cl CH3 SO3H SO3
SO3H
O NH3

O~NH--~3N~N ~25)

HOOCH4C2 C I F
O NH2
SD3H

~ NH ~ CH3 F (26)
r N ~
CHzNH ~ N
Cl F

CA 02225380 1997-12-19


- 16 -

Cl SO2C2H40S03H
~N~, o ~HC2~40so3H (27)
HO3SOH4C2HN~o~N~
Ho3soH4 C20 2 S N ~
SO3H HO NH~ N
~rN=N~N--/~ (28)

so2C2H4oso3H
SO3H F
~ N=N~NH~ 11 (2g)
SO3H SO3H NHCONH2 N-C3H6SO2c2H40so3H


SO3H SO3H
f~N=N~NH~N~NHCH2CH2NH~N~lYH~lY=~
NHC~NH2 ~ N~,N ~HCOI~H
S03 H ~ F SU3H
(30)
OH
Ho3soH~c2o2s~N=N ~ f ~ P (31)
SO3~NH~ ~N
N p

SO3H OH NH2
ClN ~N=N~ gSO2C2H~OSO3H (32)

CI~N~ C-HN SO ;~ SO~H

N~N ~ 0
SO3H HO NH~ N
~, ~r ; ~ ~H~ (33)
SO~So3H So2c2H4oso3H

CA 0222~380 1997-12-19


-. 17 -
The alkali-resistant disperse dye is a dye having a
specific dyeing property in a range of weak alkalescence.
A disperse dye suitable for the present invention can be
selected by the following dyeing method. Namely, first,
0.2 g of powder of a disperse dye (which is obtained by
finely dispersing 0.05 g of a cake of the disperse dye
with 0.15 g of a lignin type disperse agent) is added to
200 ml of a buffer agent adjusted at a pH value of 5 by
adding sodium acetate/acetic acid. Second, the dye in
the same amount as above is added to 200 ml of a buffer
agent adjusted at a pH value of 7.5 by adding potassium
dihydrogen phosphate/borax. 10 g of polyester cloth is
dipped into each of the solutions above obtained. The
temperature of each solution is raised to 130~C at
1~C/min., and each cloth is dyed at 130~C for 60 minutes.
After dyeing, reduction cleaning is conducted by a normal
method in order to remove unfixed dyes. A reflectivity
of each dyed cloth is then measured and a relative dyeing
~~ property is calculated by the following formula.

Dyeing depth of the cloth
dyed at pH 7.5
Relative dyeing property = x 100
Dyeing depth of the cloth
dyed at pH 5

If the relative dyeing property of a disperse dye is at
least 95%, it can be used for the present invention. It
is particularly preferable to use a disperse dye having a
relative dyeing property of 9g to 100. Examples of such
disperse dyes include the dyes represented by the


CA 02225380 l997-l2-l9


- 18 -

following general formulas [B-l] to [B-l0].

R~l
OH O
~ R12

H\C ~ ~ ' [B-l]


Il ~13


wherein Rll is H or Br, and each of Rl2 and Rl3 is H, Cl

or Br.
Rl~


D - N=N ~ N\R S [B-2]
R]7
wherein D is a residue of a diazo component as described
below, Rl4 is H, C1, a Cl_2 alkoxy group or a Cl_2 alkoxy-
Cl_2 alkyl group, each of Rl5 and Rl6 is H, a Cl_5 alkyl
group, an allyl group, a Cl_4 alkoxy-C2_3 alkyl group,

-C2H4CN, a -C2H4CO-Cl_4 alkyl group, a -C2H40CO-Cl_4 alkyl
O O
group, -C2H4CO ~ , -CH2 ~ , C2H4 ~ or




C2~4~ ~ , Rl7 is H, methyl group, a -NHC-Cl_4 alkyl

o
group, -NHC ~ , a -NHC-Cl_2 alkyleneoxy-Cl_2 alkyl
O O


group or a -NHSO2-Cl_4 alkyl group. D is a residue of a
diazo component represented by the following formula.

~ CA 02225380 1997-12-19


.
-- ,19

Rl~
02N ~ [Ds] ~~

Rl9
wherein R18 is H, a nitro group, a sulfomethyl group, a
cyano group, Cl, Br or a trifluoromethyl group, and Rl9
is H, Cl or Br. R21

R20J~ S~ [ D6 ~
- wherein R20 is a nitro group, a sulfomethyl group, Cl or
Br, and R21 is H, Cl or Br.
C 1'1
~22 ~ [D7]
CN
wherein R22 is H, a Cl 2 alkyl group, Cl or Br.
R2qR~

R28 ~ [D8]

wherein R23 is a nitro group, a formyl group or a cyano
- group, R24 is H, Cl or Br, and C25 is a cyano group or a
-C-Cl_2 alkyl group.
R2~
S [D9]
R27
wherein R26 is a nitro group, Cl or Br, and R27 is H, Cl
or Br. R29 C ~
~ ~=N ~ [Dlo]

R23

CA 02225380 1997-12-19


-.20 -
wherein R28 is H, a cyano group, a nitro group or Cl, and
R29 is H, a methyl group or Cl.

CH3C~

D ~ ~ [B-3]
~ NHR
NHR~

wherein D is the same residue of a diazo component as
: above, and each of R30 and R31 is H, a Cl_4 alkyl group
.. which may have a substituent, or a phenyl group.
,,
0 NH2C~O
~, ~ C ~ [B-4]

O NH2 ~
wherein R32 is a Cl 4 alkyl group, a Cl_4alkoxy-C2_3 alkyl
group or a Cl 2alkoxy-C2 3 alkyleneoxy-C2_3 alkyl group.
O NH2
~3 [B-5]

O NH2

wherein R33 is Cl or -O ~ , and R34 is Cl, -O ~ ,

-O ~ C2H4CN or -OC2H4CN.
O NH2
R35 [B-6]

O OH

CA 02225380 1997-12-19


- 21 -

--- CH
wherein R35 is -O ~ , -o ~ -OCH3~ -O ~ C2H4CN~

-OC2H4OH or -OC6Hl2OH.

HO O NH2
[B-7]

~2N O OH
-~ wherein e is 0-2.
HO O N H2
~ R36 [B-8]

H2N O OH

wherein R36 is H or a Cl_2 alkyl group.
O2N O OH
~ R37 [B-9]

HO O NH ~

wherein R37 is H, Cl, OE or -C2H4OE.
R~

N [B-10]
O=C' 'C=O


~ '~ N = 1'~ 4~ R 3g

wherein R38 is a Cl 3 alkyl group or a Cl_3 alkoxy-C2 3
alkyl group, R39 is a nitro group or Cl, and R40 is H or

CA 0222~380 1997-12-19


: -.22-

a Cl_2 alkoxy group.
Examples of these dyes include C. I. Disperse Blue
27, 55, 56, 60, 73, 77, 87, 143, 214, 283, 291, 321, and
333,C. I. Disperse Violet 1, 26, 27, 28, 38, 46, 57, and
93.1,C. I. Disperse Red 50, 60, 65, 88, 91, 117, 125,
143, 145, 146, 152, 153, 183, 185, 191, 192, 200, 225,
240, 279, 283, and 343,C. I. Disperse Orange 1, 13, 41,
43, 44, 61, 62, 73, 74, and 76,C. I. Disperse Yellow 44,
. - 54, 64, 67, 149, 160, 163, and 192, and the dyes
represented by the following formulas ( 34)-(51).

CA 02225380 1997-12-19


- 23 -


~~2 OCH3
02N~N-N~NHC~Hs (34)
C I NHCOCH 3

CN

02N~ ~¢ ~ \C2H4CN
CN
--, 02N~N=N ~ N=N ~N ~ ; (36)

C,H3
o C,N~C o
OCH3 ,\~3 (37)

HO

Cl2H5
o C,N~C o

- -:- 02N~N-~ ~ (38)
HO
Cl N~ ~ ~C2H40COCH3 (39

CL S \C2H5

. CA 02225380 1997-12-19

- ~:
- 24 -



CI~N~ ~ <~zH40C0

Cl N
~ ~N N~N/C2H-4ococH3 (41)
Cl ~S\C2H40COCH3

. Cl
:: ,~N~~ <C2HgOCOOc2Hs (42)
Cl SY C2H4OCOOc2Hs
NHCOCH 3

~ ~ N N~N <C2H40COOc2Hs
Cl S NHCOCH C2HgOCOOC2H5


~N~ ~ <C2H4CN
C I S CsH l l (n)
NHCûCH3

- 02N~ N=N~3N(C2H40cl~3)2
N' NHCOCH3

CN

02NJ~N=N~N< ~ (46

CA 02225380 1997-12-19



8r~N=N~N(C2H40CH3)2
~S NHC3C~3
Br

CN CH3

7~'NH~ (48)

NHC2H~aC2H40H
CN
~ (t2Hs


CN
g~_ "~ ~, <C2H5


CN

~N=N~' ~ C2H~CN (51)

CA 0222~380 1997-12-19


-..26 -
The proportion of such a disperse dye is determined
suitably depending on the proportion of polyester in the
mixed fibers. When using a disperse dye, a disperse dye
composition is prepared with a disperse agent and other
auxiliary agents in accordance with a usual method.
Examples of cellulose fibers to be dyed by the method
of the present invention usually include cotton, viscose
rayon, cupra ammonium rayon, and hemp. Examples of
-- polyester fibers include polyethylene terephthalate,
polybutylene terephthalate, and the like. The dyeing
method of the present invention is effective also for
easily dyeable polyester fibers. Mixed fibers comprising
cellulose fibers and polyester fibers are usually in the
form of mixed fabric, mixed knitted fabric, or non-woven
fabric. The mixing ratio of polyester fibers to
cellulose fibers is 1:99 to 99:1 by weight, preferably
20:80 to 80:20 by weight.
To dye the mixed fibers by the method of the present
- invention, a water-soluble alkali is used as an agent for
adjusting the pH value together with the above-mentioned
reactive dye and disperse dye. Examples of said water-
soluble alkali include alkali metal hydroxides such as
sodium hydroxide and potassium hydroxide, alkali metal
carbonates such as sodium carbonate and potassium
carbonate, alkali metal hydrogen carbonates such as
sodium hydrogen carbonate and potassium hydrogen
carbonate, alkali metal silicates such as sodium silicate


CA 0222~380 1997-12-19


.27
and lithium silicate, alkali metal phosphates such as
sodium phosphate and potassium phosphate, alkali metal
borates such as sodium borate, an alkali metal salt of an
organic fatty acid having a carbon number of one or two
such as sodium formate and potassium acetate, and a
mixture of such alkali metal salts. The amount of the
water-soluble alkali to be used is usually 0.01 to 5 g/~
in the dye bath. It is particularly preferable to use
-; 0.1 to 1 g/e of an alkali metal silicate, an alkali metal
carbonate, or a mixture of such alkali metal salts.
Further, if necessary, usually 1 to 150 g/e, preferably
10 to 80 g/~ of an electrolyte (sodium chloride or sodium
sulfate) is added to the dye bath. The mixed fibers are
dipped into this dye bath and dyed.

15The p~ of the dye bath is maintained in a range of
9.0 to 12.0, preferably 9.5 to 12.0 before raising the
temperature. After dyeing, the p~ is lowered to a range
of 8.0 to 11.0 by consumption of an alkali by the
reactive dye. The dyeing temperature is 100 to 150~C,
preferably 120 to 140~C, and the dyeing time is 30 to 180
minutes, preferably 60 to 120 minutes.
The method of the present invention makes it possible
to dye both of cellulose fibers and polyester fibers
satisfactorily in a single bath and in one step. That
is, the present method is an industrially extremely
advantageous method.
Hereinafter, the present invention will be described

CA 0222~380 1997-12-19


-.28 -


in further detail with reference to Examples. However,
the present invention is by no means restricted to such
specific Examples, unless it is beyond the gist of the
present invention.
EXAMPLE 1
A dye bath was prepared by adding 0.2 g of the
reactive dye represented by the above formula (l), 0.2 g
of Resolin (registered trademark) Red F3BS (C. I.
- Disperse Red 343), 8.0 g of Glauber's salt and 20 mg of
silicate of soda as an agent for adjusting the pH to 200
ml of water. Into the dye bath thus obtained, 10 g of
mixed fabric comprising polyester and cotton
(polyester:cotton = 50:50) was dipped. The temperature
was raised to 130~C at 1~C/min., and the fabric was dyed
at 130~C for 60 minutes. Thereafter, water-washing,
soaping, water-washing and drying were conducted
successively to obtain a brilliant red fabric dyed
excellently with the same color. The pH of the dye bath
-' was 11.5 before dyeing and 8.5 after dyeing. The dyeing
property of the dye was extremely good, and the dyed
fabric thus obtained showed excellent fastness against
light, washing and rubbing.
COMPARATIVE EXAMPLE 1
A dye bath was prepared by adding 0.2 g of Resolin
Red F3BS to 200 ml of water and by adjusting the pH at 5
with acetic acid. Into the dye bath thus obtained, 10 g
of mixed fabric comprising polyester and cotton


CA 0222~380 1997-12-19


-.29 -

(polyester:cotton = 50:50) was dipped. The temperature
was raised to 130~C at 1~C/min., and the fabric was dyed
at 130~C for 60 minutes. Thereafter, reduction cleaning
and water-washing were conducted to obtain a fabric
wherein polyester was dyed.
A dye bath was then prepared by adding 0.2 g of the
reactive dye represented by above formula (1), 12.0 g of
Glauber's salt and 3 g of soda ash as an agent for
- adjusting a pH value to 20~ ml of water. Into the dye
bath thus obtained, the above fabric wherein polyester
was dyed was dipped. The temperature was raised to 60~C
at 1~C/min., and the fabric was dyed at 60~C for 60
minutes. Thereafter, water-washing and drying were
conducted to obtain a brilliant red fabric dyed excellent
with the same color. It took 8 hours to dye the mixed
fabric comprising polyester and cotton. The dyed fabric
thus obtained showed excellent fastness against light,
washing and rubbing.
~- EXAMPLE 2

A dye bath was prepared by adding 0.4 g of the
reactive dye represented by the above formula (4), 0.4 g
of Dianix (registered trademark) Navy Blue BG-SF (a
mixture of C. I. Disperse Violet 93.1 and C. I. Disperse
Blue 291 wherein the mixing ratio is 1:1), 8.0 g of
Glauber's salt, 0.2 g of a higher alcohol sulfate and 40
mg of soda carbonate to 200 ml of water. Into the dye
bath thus obtained, 10 g of mixed fabric comprising


CA 0222~380 1997-12-19


-..30 -
polyester and cotton (polyester:cotton = 50:50) was
added. The temperature was raised to 130~C at 1~C/min.,
and the fabric was dyed at 130~C for 60 minutes.
Thereafter, water-washing, soaping, water-washing and
drying were conducted successively to obtain a navy color
fabric dyed excellently with the same color. A p~ of the
dye bath was 11.5 before dyeing and 8.5 after dyeing. A
dyeing property of the dye was extremely good, and the
fabric thus obtained showed excellent fastness against
light, washing and rubbing.
EXAMPLES 3-1 TO 3-11
Using the reactive dyes and the disperse dyes
described on Table 1, mixed fabrics comprising polyester
and cotton (polyester:cotton = 50:50) were dyed by the
same method as in Example 1. With regard to fastness
against light, washing and rubbing, the fabrics thus dyed
had such high qualities as not be inferior to a dyed
fabric obtained by a conventional method conducted in two
baths and two steps.


CA 0222~380 1997-12-19
' ~ _

~ 31 -

Table 1
Color of
Example Reactive dye % (o.w.f.) Disperse dye % (o.w.f.) dyed
fabric

3-1 C. I. Reactive Blue 116 2% C. I. Disperse Blue 60 2% Turquoise
blue
C. I. Disperse blue 291 2%
3-2 C. I. Reactive blue 120 4% Navy blue
C. I. Disperse Violet 93.1 2%
Dye represented by the
3_3 C. I. Disperse Yellow 64 2% Yellow
formula (7) 2%
Dye represented by the
-- 3_4 C. I. Disperse Orange 73 2% Orange
- _. formula (8) 2%
3 5 Dye represented by the C. I. Disperse Yellow 163 2% Yellow
formula (16) 2%
3-6 Dye represented by the Dye represented by the Blue
formula (25)3% formula (46) 0.5%
Dye represented by the
3-7 Dianix Navy Blue BG-SE 200 2% Navy blue
formula (4) 4%
Dye rep-esented by the
3-8 formula (4) % Dianix Black BG-FS 200 4% Black
Dye represented by the
formula (18) 3%
Dye represented by the
formula (30) 3% C. I. Disperse Yellow 54 2%
- Dye represented by the C. I. Disperse Yellow 44 0.2%
formula (29) 1%
Dye represented by the
~ formula (31) 2% Dye represented by the Yellowish
Dye represented by the formula (40) 2% red
formula (28) 0.1%
Dye represented by the
3-11 formula (29) 2.5% Dye represented by the Red
Dye represented by the formula (48) 2%
formula (18) 0.5%

CA 0222~380 1997-12-19


- -.32 -

EXAMPLE 4
By the same method as in Example 1 except for using a
mixed fabric comprising polyester and rayon
(polyester:rayon = 50:50), dyeing was conducted. As a
result, a brilliant red fabric dyed well with the same
color was obtained.
EXAMPLE 5
By the same method as in Example 1 except for using a
mixed fabric comprising polyester and cotton (polyester:

.
cotton = 80:20), and using 0.13 g of the reactive dye
represented by the formula (1) and 0.32 g of Resolin Red
F3BS, dyeing was conducted. As a result, a brilliant red
fabric dyed excellently with the same color was obtained.
EXAMPLE 6

By the same method as in Example 1 except for using a
mixed fabric comprising polyester and cotton
(polyester:cotton = 20:80), and using 0.3 g of the
reactive dye represented by the formula (1) and 0.12 g of
-~ Resolin Red F3BS, dyeing was conducted. As a result, a
brilliant red fabric dyed excellently with the same color
was obtained.


Representative Drawing

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Administrative Status

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Administrative Status

Title Date
Forecasted Issue Date Unavailable
(86) PCT Filing Date 1996-06-20
(87) PCT Publication Date 1997-01-09
(85) National Entry 1997-12-19
Dead Application 2003-06-20

Abandonment History

Abandonment Date Reason Reinstatement Date
2002-06-20 FAILURE TO PAY APPLICATION MAINTENANCE FEE

Payment History

Fee Type Anniversary Year Due Date Amount Paid Paid Date
Application Fee $300.00 1997-12-19
Registration of a document - section 124 $100.00 1998-04-21
Maintenance Fee - Application - New Act 2 1998-06-22 $100.00 1998-06-18
Maintenance Fee - Application - New Act 3 1999-06-21 $100.00 1999-06-08
Maintenance Fee - Application - New Act 4 2000-06-20 $100.00 2000-06-19
Maintenance Fee - Application - New Act 5 2001-06-20 $150.00 2001-06-06
Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
DYSTAR JAPAN LTD.
Past Owners on Record
HIHARA, TOSHIO
HIMENO, KIYOSHI
SEKIOKA, RYOUICHI
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) 
Description 1997-12-19 32 693
Claims 1997-12-19 2 47
Abstract 1997-12-19 1 10
Cover Page 1998-04-14 1 28
PCT 1997-12-19 12 414
PCT 1998-06-29 5 178
Assignment 1998-04-21 2 98
Assignment 1997-12-19 3 95
Correspondence 1998-03-24 1 29
Fees 2000-06-19 1 40