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Патент USA US3084026

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3,084,015
United, States Patent ,Of?ce
Patented 'Apr.°2,-1963
. a.
T2
In, order’ to produce strong dyeingson polyethylene
.terephthalate?bers it.is..o£ advantage .toincorporate a
3,084,015
swelling agent in the dyebath, or- to carry out the dyeing
»BROCESS 1FOR~ DYEING . OR .
.
,.
-
.
,
,
_
.PRINTINGwFIBROUS
.process.under.pressureata.EIIIP?I?tDIQJbWe 100° (3-,
MATERIALS- 01F~ AnoMancrQLY-aswss
"Raymond _ :Defago,
for example, within theirange.v of 1:20to 140° C. As
swelling agents there may be used aromaticcarboxylic
acids, forexamplebenzoic acid or salicylic acid-‘or
I
.Rieliéri; Switzerland, ,as‘signors' to * Ciba Limited, ' Basel,
Switzerland, a’ Swiss‘ company
No‘ Drawing. >Filed~ 0Ct.'-25,'-1960,~S8l‘.1'N0.=i64§109
applicationv nSwitzerland .‘Oct. 3730,11959
phenol-s, vforexample, ortho- or rpara-hydroxyediphenyl,
or aromatic halogen-compounds, for example,'cchloro
- - Claims priority, ..
.6 (Claims. ;..(C_l._-;8-,-,-_39)
'10
benzene, ortho-dichlorobenzene or trichlorobenzene, or
15
partsand percentagesjbeing by weight.
;This :inyention; is based on: the (observation 1; that~.yalu
able dyeings and prints are produced on ?brous materials
of aromatic polyesters, especiallyipolyethylene,tereph
phenyl methyl earbinol. or diphenyl. ‘The dyeings so ob
tained are distinguished by their good vfastness to sublima
tion and light.
The ~followingexamples illustratel'the invention, the
ff “a 11,-,arnino-Z-cyano-4
.alkylamino. especially learning-Howe salkyl-aminow
, lraminoJZ-cyano<4¢cyc1oalkylamino- “or gl-aminor2fcyano
Example 1 v
.4rpheny1amino-a.nthraquinone.freertw
:-1 part of;an aqueous ‘paste of the dyestut‘f of the
‘formula
.partingsoluhili-ty in water. ,Ihe ern'rlower falkyLmeans
alkyl having ‘at most_,6,carbon,atorns; '_—The dyestu?s may
20
:. besubstituteddn. the alkyl en-phenyl radisal,:.f.or;exernple
in the alkyl radicalpbyL a eyanogroup andin- the phenyl
.radical we halogen;- atom, grtanal‘ky-ltalkoxy. orhydroxyl
group.
.
.As :examplesp?such dyestuffs: there.;-may bementionem
25
lramino52¢cyano4~methylamino7,
II
0
NH
‘ li-amino#2-cyano-4-ethylamino7,
lraminoJpyanoA-cyanethylaminof,
,and approximately-one part ofbdried sul?te cellulose
waste liquor are ground'in a roller-mill to form a1?ne
" ~1Lamino;2-cyanoe4-isopropyleaminog
1-amino-2-cyano-4-butylamino-,
1-amino-2~cyano~4-cyclohexylamino-,
1-aminoi2-cyano4-phenylamino,
30 pastelhaving a dyestulf content of about ‘10%.
lOO‘partsof a'?brous material of polyethylene tereph
thalate are cleaned for half an hour in a bath containing,
-l-amino-2~cyano-4— (_p ara- or =meta7methylpheny1) -amino»,
1l_amino-2-cyano-4~(para-methoxyphenyl)lamino-,
:-l1arriino-2écyano~4~(ortho-, —meta- or .para-chlorophenyl) -
in 1000 parts of-water, l to '2 parts of the sodium salt‘of
N-benzyl-n-heptadecyl-benzimidazol disulfonic acid and
35 onepartof a concentrated aqueous solution of ammonia.
“amino-or
‘The material isthen/transferred to a dyebath containing
' iyl)-am_ino-anthraquinone.
-as described above hasbeen dispersed with the. aid of 4
3‘000-parts. of'water inwhich the dyestuff pasteobtained
-Ifarnino-LcyanoA-(ortho, ~meta- vor .pa-ra-hydroxyphen
parts. of the sodiumsalt of Nebenzyl-n-heptadecyl-benzirn
, -_These compounds can‘ be obtaineddn .known,manner by 40 'idazol-disulfonic acid. The rwholeis heated in apres
3 heating . the appropriate 1-amino-4-alkylamino-, ‘l-amino
none-Z-sulfonic?acid, in water with an alkali metal cyanide.
,Iynsteadjof a single dyestuff there maybe usedéa mixture
sure vessel to 130° C. andmaintained at that‘temperature
~for abouthalfan-hour. . The materialisthen rinsed well,
and, if necessary, washediforhalf an hour at 60 to- 80° C.
ture, for example, 1:5-dihydroxy-4-nitro-8- or -1:8-dihy
This dyestul’r' has a surprisingly good a?inity for poly
w~4-cycl7oalkylarnino- or ‘llamino-4-phenylamino-anthraqui
‘ of such dyestuffs, :and~=in-this way the ai?nity is~often 45 with a solution which contains, in 1000 partsof water
one part of the sodium salt of N-benzyl-n-heptadecyl
considerably enhanced. There may be used a mixture of
benzimi'dazol-disulfonic acid. There is obtained a strong
different dyestuffs of the kind de?ned above or a mixture
greenish-blue ‘dyeing having good properties of fastness.
of such a dyestutf with another dyestu? of similar struc
droxy-4-nitro-5-phenylami-no-anthraquinone.
For dyeing the aforesaid dyestuffs are advantageously
50
used in a ?nely dispersed form and in the presence of a
dispersing agent, such as a soap, sul?te cellulose waste
liquor or a synthetic detergent, or a mixture of a wetting
agent and dispersing agent. It is generally of advantage
before dyeing to convert the dyestuff into a dyestuif prepa
ration which contains a dispersing agent and the ?nely
divided dyestulf in a form such that a ?ne dispersion is
ester ?bers, in view of the fact that it has been disclosed
by Salvin (American Dyestuif Reporter, 48th year
(13.7.59), page 35), that this dyestuff is unsuitable for
dyeing cellulose acetate silk on account of its insuf?cient
affinity and insuf?cient stability in the dyebath and also
owing to its slow speed of absorption.
By using, instead of l-amino-2-cyano-4-pheny1amino
anthraquinone,
l-amino - 2 - cyano - 4 - cyclohexy-larnino
anthraquinone there is obtained a somewhat less greenish
blue dyeing having the same good properties of fastness.
obtained when the dyestu? preparation is diluted with
water. Such dyestuff preparations can be made in known 60
The good affinity of this dyestuff for polyester ?bers
manner, for example, by reprecipitating the dyestuff
is surprising because it must be concluded from Example
from sulfuric acid and grinding the suspension so ob
6 of the German Patent No. 580,012 to LG. Farben
tained with sul?te cellulose waste liquor, and, if desired,
in'dustr-ie A.G., issued July 4, 1933, that it hardly dyed
by grinding the dyestutf in a highly e?icient grinding
apparatus in the dry or wet state in the presence or ab 65
sence of :a dispersing agent.
'
cellulose acetate silk at all.
The dyestuffs mentioned in the ?rst and third para
3,084,015
3
4.
graphs of this example can be obtained by the process
described in British Patent No. 359,850 to I.G. Farben
Example 12
The following ingredients are mixed together:
industrie A.G., accepted October 29, 1931, by heating 20
300 parts of gum arabic ( 1:1)
300 parts of crystal gum (1:2)
parts of sodium 1-amino-4-anilino- or 1~amin0-4~hexahy
droanilino-anthraquinone-Z-sulfonate with 20 or 30 5
250 parts of water
parts, respectively, of potassium cyanide in 1000 parts of
water at a temperature of 85° C. to 140° C.
Examples 2——l0
In the following table are mentioned further dyestuffs 10
which dye polyethylene terephthalate ?bers by the process
40 parts of cyclohexanone
40 parts of thiodiglycol
50 parts of a solution of 100% strength of the sodium
salt of meta-nitrobenzene sulfonic acid
20 parts of a mixture of potassium oleate and pine-oil
described in Example 1 the tints given in column II.
1000 parts
Dyestuft
Tint
Into 800 parts of the above stock thickening are stirred
15 by means of a high speed stirring device 200 parts of the
2 ____ __ l-amino-2-eyano~4-methyleminoanthraqulnone.
3 ____ __ 1-amino-2~cyano-4-isopropylaminoanthraquinone.
4 ____ __ 1—amin0—2-cyano~4-n-butylaminoanthrnquinone
5 ____ __
l-emino-2-cyano-4~cyauethylaminoanthraqui-
6 ____ --
l-amino-2-cyand4-(meta-methyl-phenyl)-
Blue;
dyestutf obtained as described in the ?rst paragraph of
Example 1, the stirring being continued until the dyestu?
is completely dispersed. A fabric is printed with the
resulting printing paste, and the print is dried and steamed
Do.
Do.
Do.
_
none.
aminonnthraquinone.
7 .... __
l-amino-2-eyano~4-(para-methyl-phenyl)-am-
8 ____ __
l-amino-2-cyano4-(ortho-methoxyphenyl)-
9 ____ -.
l-amino~2-eyano4-(para-methoxyphenyD-
inonnthraquinone.
blue.
Do.
cold water, centrifuged and dried. There is obtained a
fast blue print.
Green-blue.
aminoanthraquinone.
aminoanthraquinone.
10-____ l-nmino-2-eyano-4-(parn-ethoxyphenyl)-arninoanthraquinone.
for 45 minutes under a pressure of % of an atmosphere
(gauge). The material is then rinsed for 10 minutes in
Greenish
‘
Blue-green.
‘ What is claimed is:
25
Green.
‘
industrie A.G., accepted October 29, 1931, by heating the
sodium salt of the appropriate 1-amino-4-alkylamino- or
‘
3. Polyethylene terephthalate ?bers dyed with l-amino
2-cyano-4-phenylaminoanthraquinone.
4. Polyethylene terephthalate ?bers dyed with l-amino
2-cyano-4-(p-ethoxy-phenyl)-aminoanthraquinone;
5. Polyethylene terephthalate ?bers dyed with l-amino
thalate are cleaned for half an hour in a bath containing
in 1000 parts of water 1 to 2 parts of the sodium salt
2-cyano-4-isopropylaminoanthraquinone.
acid 40
and 1 part of a concentrated aqueous solution of am
monia. The material is then treated in a bath which con
tains in 1000 parts of water 3 to 5 parts of diammonium
phosphate and 0.5 to 1 part of N-benzyl-,u—heptadecyl
benzimidazol-disulfonic'acid for 10 to 15 minutes at 50° 45
C. There are then added 3 to 5 parts of the sodium salt
of ortho-phenylphenol dissolved in 1000 parts of water,
and the liquor is maintained at 50 to 55° C. for 15 min
utes while circulating the liquor. A dyestutf paste ob
tained as described in the ?rst paragraph of Example 1 is
added and the bath is brought to the boil in the course of
half an hour and dyeing is carried on for l to 11/2 hours
at the boil, and the material is then rinsed while warm. A
‘
6. Polyethylene terephthalate ?bers dyed with l-amino
2-cyano-4-butylaminoanthraquinone.
‘
References Cited in the ?le of this patent
UNITED STATES PATENTS
1,938,029
2,496,414
2,881,045
2,922,691
Kugel ________________ .. Dec. 5,
Seymour et al ___________ __ Feb. 7,
Mecco et al. ___‘ ________ __ Apr. '7,
Grossman ____________ __ Jan. 26,
1933
1950
1959
1960
- 2,926,987
Freyermuth et al. ______ __ Mar. 1, 1960
2,937,190
3,005,822
Straley et al ___________ _. May 17, 1960
Jenny ________________ __. Oct. 24, 1961
359,850
Great Britain __________ __ Oct. 29, 1931
FOREIGN PATENTS
greenish-blue dyeing having good properties of fastness
is obtained.
l-amino-Z
2-cyano-4-cyclohexylamino-anthraquinone.
acid
with potassium cyanide in water.
Example 11
100 parts of a ?brous material of polyethylene tereph
of N-benzyl - [.L - heptadecyl-benzimidazol-disulfonic
cyano - 4 - lower - alkylaminoanthraquinones,
cyano~4-cycloalkylaminoanthraquinones and 1-amino~2
cyano-4-phenylaminoanthraquinones free vfrom acid
groups imparting solubility‘in Water.
2. Polyethylene terephthalate ?bers dyed with l-amino
The above mentioned dyestuffs can also be made by
the process of British Patent No. 359,850, to LG. Farben
l-amino-4—phenylamino-anthraquinone - 2 - sulfonic
i
l. Polyethylene terephthalate ?bers dyed with a dye
stu?’ selected from the group consisting of 1-amino-2
55
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