CA2084613A1 - Liquid preparations of a 2:1 chromium complex dye - Google Patents
Liquid preparations of a 2:1 chromium complex dyeInfo
- Publication number
- CA2084613A1 CA2084613A1 CA002084613A CA2084613A CA2084613A1 CA 2084613 A1 CA2084613 A1 CA 2084613A1 CA 002084613 A CA002084613 A CA 002084613A CA 2084613 A CA2084613 A CA 2084613A CA 2084613 A1 CA2084613 A1 CA 2084613A1
- Authority
- CA
- Canada
- Prior art keywords
- weight
- dye
- chromium complex
- preparation
- complex dye
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/16—Monoazo compounds containing chromium
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
- C09B69/04—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds
- C09B69/045—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds of anionic azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
O.Z. 0050/42903 Abstract of the Disclosure: Dye preparations containing the dye of the formula 2 [C13H27NH3]?
one or more aliphatic amines and ethanol are useful for the ink-jet process.
one or more aliphatic amines and ethanol are useful for the ink-jet process.
Description
o- z ~50/42go3 Liquid ~reparations of a 2 l_chromium complex dye The pre~ent invention concçrns novel dye prepara-tion~ containing from 1 to 50% by weight, based on the weight of the pr~paration, of the dye of the formula 02N ~ 20 cr 0 ~ 0 2 [Cl3~27NH3]~
L3s ~ N =
fro~ 0.1 to 10% by weight, b~ed on the weigh~ of the preparation, of one or more primary 9 ~econdary or tertiary aliphatic ~mines a~d from 40 to 98.9% by w~ight, ba~ed on the weight of the preparation, of etha~ol, and th~ use thereof.
JP-A-276 871/1990 di~clo~e~ inka for the ink-~st pr~ce~ he colorant~ involved ar~ mlxtures o~ rhodamine d~ with chromium complex dye~. ~he ink~ des~ribed there alao contain amine~ and a p-hydroxyb~n~oiG a~id derivative. ~owever, i~ ha~ been found tha~ the~e ink~
have un~ati~actory application properties, in particular ~n inad~quat0 ~torage life in liquid formulation3.
It i8 an object of th~ pre~ent inv~ntion to provide novel liquid prepara~ions of a 2:1 chromium complex dye which have a long ~torage life~
We hav~ fou~d that thi~ object i8 achieved by the dy~ preparations de~i~ed at th~ b~ginningA
The dye i~ in gener,~l present therein a~ a 2~61~
- 2 - O~. 0050/42903 mixture of the 5-nitro compound of the formula ;O2N ~ N - N
~ Cr~
O ~ O 2 [Cl3H27NH3]~
L35~N=
and th~ 4-nitro compound of the formula O O
: ¦ O ~ O ¦ 2 tCI3H27NL23~3 103s~2=~ 1 It can be obtained by the ~ethod described in ~ GB-A 1 028 409.
; 5 The dye i~ present in the form of the tridecylamine 3alt. For the purpose~ of the pres~nt i~vention thi~ cover~ not only the n-tride~ylamine ~alt 2~8~
L3s ~ N =
fro~ 0.1 to 10% by weight, b~ed on the weigh~ of the preparation, of one or more primary 9 ~econdary or tertiary aliphatic ~mines a~d from 40 to 98.9% by w~ight, ba~ed on the weight of the preparation, of etha~ol, and th~ use thereof.
JP-A-276 871/1990 di~clo~e~ inka for the ink-~st pr~ce~ he colorant~ involved ar~ mlxtures o~ rhodamine d~ with chromium complex dye~. ~he ink~ des~ribed there alao contain amine~ and a p-hydroxyb~n~oiG a~id derivative. ~owever, i~ ha~ been found tha~ the~e ink~
have un~ati~actory application properties, in particular ~n inad~quat0 ~torage life in liquid formulation3.
It i8 an object of th~ pre~ent inv~ntion to provide novel liquid prepara~ions of a 2:1 chromium complex dye which have a long ~torage life~
We hav~ fou~d that thi~ object i8 achieved by the dy~ preparations de~i~ed at th~ b~ginningA
The dye i~ in gener,~l present therein a~ a 2~61~
- 2 - O~. 0050/42903 mixture of the 5-nitro compound of the formula ;O2N ~ N - N
~ Cr~
O ~ O 2 [Cl3H27NH3]~
L35~N=
and th~ 4-nitro compound of the formula O O
: ¦ O ~ O ¦ 2 tCI3H27NL23~3 103s~2=~ 1 It can be obtained by the ~ethod described in ~ GB-A 1 028 409.
; 5 The dye i~ present in the form of the tridecylamine 3alt. For the purpose~ of the pres~nt i~vention thi~ cover~ not only the n-tride~ylamine ~alt 2~8~
- 3 - O.Z. ~050/42gO3 but also th~ isotridecylamine salt (i~stridecyl as hereinafter defined).
The aliphatic amine~ u~ed according to the invention are primary, ~econdary or tertiary amines. They have at least 8 carbon atoms in the molecule and are preferably alkylamines.
Suitable alkylamines have from 8 to 40, pre-fsrably from 10 to 30, in particular from 14 to 20, carbon atom~ in the molecul~.
Suitable prima~y amine~ are for example octyl-amine, 2-ethylhexylamine, isooctylamine, nonylamlne, i~ononylamine, decylamine, isodacylamine, undecylamine, dodecylamine, tridecylamine, i~otrid~cyl d na (the above de~ignatiOllB i800ctyl, isononyl, i~odecyl and isotridecyl are trivial name~ derived from the oxo proce~s al~ohols - cf. Ullmanns ~n~yklop~die der technischen Ch~mie, 4th Edition, Volume 7, p~ga~ 215 to 217, and Volum~ 11, page3 435 and 435), tetradecylamine, pentadecylamine, hexa-decylamine, heptadecyla~ine, octadacylamin~, nonade~yl-amine or eicosylamine~
Suitable ~econdary amine~ are for exampledibutylamine, dii30butylamine, N~thyl ~-~2-ethylhexyl)-~mine, bis(2-ethylhexyl3amine or diisotridacylamlne.
Suitable tertiary amlne~ ara for example tri-butylamine, ~,N-dim~thyl-~-~2-ethylhexyl)2mine, N,~ dim~thyl N-C10/Cl3-alkylaml~e (mixtur~), tris(2-ethyl-hexyl~amine or ~rii~otride¢ylamine.
Owing to the following equilibrium r~action the prLm3ry, s~condary or tsrtiary aliphatic ~mine~ (repre-sented in the equation by the ~tructural eleme~t ~ N) canalso be present a~ a whol~ or in part in the fo~m of their amin~ salt~:
3 N ~ C13~27NH3 _ ~, NH ~ Cl3H27NH2 The dy~ preparation~ of th¢ invention contain from 1 ~o 50% by weight, prefer~bly from 30 to 40~ by 208~613 - 4 - O.z. 0050i42903 weight, each percentage being ~ased on the weight of the preparation, of the dye.
The novel dye preparations further ~ontain from 0.1 to 10% by weight, preferably from 4 to 8% by weight, each percentage being based on the weight of the prepara-tion, of one or more primary, secondary or tertiary aliphatic amines.
The novel dye preparations further contain from 40 to 98.9% by w~ight, preferably from 52 to 66% by weight, each percentage being based on the weight of the preparation, of ethanol.
Further possible ingredients of the dye prepara-tion~ according to the invention are for example auxilia-rie~, such as conducting ~alt~ or fungicides. The propor-tion of these components iB in general within the range from 0 to 10~ by weight, preferably from 0 to 5% by weight, each percentage being ba~ed on the weight of the preparation.
The dye preparation~ of the invention can be obtained for oxample by dis~olving the dye tog-thor with th- amino or an amino mixture and, if u~ed, tho auxilia-rio~ in othanol in tho abovomontionod ratios.
Tho novol dyo preparations are advantageou~ly suitab}o for u~e in the ink-jot process.
The ink-~et process i~ known per ~e. It involves projocting droplet~ of a writing fluid ~ink) onto a sub-strate, for examplo paper, wood, textiles, pla~tic or metal, from one or more small ~ets in a ~pecific manner.
Electronic control devices group the individual droplets together to form characters or graphical patterns.
The dye preparations of the invention are also ~uitable for use as marking fluids in writing implement~
or as the baeis for coating compo~itions, for examplo wood st ins, printing inks, color ribbon ink~, stamp inks or ballpoint pen paste~.
The preparations of the invention havo a long storago lifo.
~' .
~-.... , .. - ........ . .
_ 5 _ O.Z. 0050/42gO3 The inv~n~ion i8 further illu~trated by the following ~xample:
EXAMP~E
2 g of ~is(2-ethylhexyl)amine were di~olved in 568 g of ethanol (99.5% by weight). 30 g of the dye of the formula r ~ ~
t ~ 2 [Cl3a27NH3]~
~35 ~ N =
(the dye comprisi~g, as mentio~d earlier~ an isomer mixture) were added ~ith stirring and di~solved at room temp~rature in th~ cour~ of 2 hour~. Then 10 g of a filter aid based on diatomaceous earth were added a~d the mixture wa~ filtered ~hrou~h a pre~ur~ ilter.
The liquid dye preparatio~ thu3 obtai~d wa~ fxe~
of cry~talline matt2r~ a8 wa~ veriied l~nder the microscope at ~bout 700-fold magnification.
15~h~ ~tability o~ thia liquid ~o~mulation at -18~C, ~ 0C a~d ~7C i~ excellent.
The aliphatic amine~ u~ed according to the invention are primary, ~econdary or tertiary amines. They have at least 8 carbon atoms in the molecule and are preferably alkylamines.
Suitable alkylamines have from 8 to 40, pre-fsrably from 10 to 30, in particular from 14 to 20, carbon atom~ in the molecul~.
Suitable prima~y amine~ are for example octyl-amine, 2-ethylhexylamine, isooctylamine, nonylamlne, i~ononylamine, decylamine, isodacylamine, undecylamine, dodecylamine, tridecylamine, i~otrid~cyl d na (the above de~ignatiOllB i800ctyl, isononyl, i~odecyl and isotridecyl are trivial name~ derived from the oxo proce~s al~ohols - cf. Ullmanns ~n~yklop~die der technischen Ch~mie, 4th Edition, Volume 7, p~ga~ 215 to 217, and Volum~ 11, page3 435 and 435), tetradecylamine, pentadecylamine, hexa-decylamine, heptadecyla~ine, octadacylamin~, nonade~yl-amine or eicosylamine~
Suitable ~econdary amine~ are for exampledibutylamine, dii30butylamine, N~thyl ~-~2-ethylhexyl)-~mine, bis(2-ethylhexyl3amine or diisotridacylamlne.
Suitable tertiary amlne~ ara for example tri-butylamine, ~,N-dim~thyl-~-~2-ethylhexyl)2mine, N,~ dim~thyl N-C10/Cl3-alkylaml~e (mixtur~), tris(2-ethyl-hexyl~amine or ~rii~otride¢ylamine.
Owing to the following equilibrium r~action the prLm3ry, s~condary or tsrtiary aliphatic ~mine~ (repre-sented in the equation by the ~tructural eleme~t ~ N) canalso be present a~ a whol~ or in part in the fo~m of their amin~ salt~:
3 N ~ C13~27NH3 _ ~, NH ~ Cl3H27NH2 The dy~ preparation~ of th¢ invention contain from 1 ~o 50% by weight, prefer~bly from 30 to 40~ by 208~613 - 4 - O.z. 0050i42903 weight, each percentage being ~ased on the weight of the preparation, of the dye.
The novel dye preparations further ~ontain from 0.1 to 10% by weight, preferably from 4 to 8% by weight, each percentage being based on the weight of the prepara-tion, of one or more primary, secondary or tertiary aliphatic amines.
The novel dye preparations further contain from 40 to 98.9% by w~ight, preferably from 52 to 66% by weight, each percentage being based on the weight of the preparation, of ethanol.
Further possible ingredients of the dye prepara-tion~ according to the invention are for example auxilia-rie~, such as conducting ~alt~ or fungicides. The propor-tion of these components iB in general within the range from 0 to 10~ by weight, preferably from 0 to 5% by weight, each percentage being ba~ed on the weight of the preparation.
The dye preparation~ of the invention can be obtained for oxample by dis~olving the dye tog-thor with th- amino or an amino mixture and, if u~ed, tho auxilia-rio~ in othanol in tho abovomontionod ratios.
Tho novol dyo preparations are advantageou~ly suitab}o for u~e in the ink-jot process.
The ink-~et process i~ known per ~e. It involves projocting droplet~ of a writing fluid ~ink) onto a sub-strate, for examplo paper, wood, textiles, pla~tic or metal, from one or more small ~ets in a ~pecific manner.
Electronic control devices group the individual droplets together to form characters or graphical patterns.
The dye preparations of the invention are also ~uitable for use as marking fluids in writing implement~
or as the baeis for coating compo~itions, for examplo wood st ins, printing inks, color ribbon ink~, stamp inks or ballpoint pen paste~.
The preparations of the invention havo a long storago lifo.
~' .
~-.... , .. - ........ . .
_ 5 _ O.Z. 0050/42gO3 The inv~n~ion i8 further illu~trated by the following ~xample:
EXAMP~E
2 g of ~is(2-ethylhexyl)amine were di~olved in 568 g of ethanol (99.5% by weight). 30 g of the dye of the formula r ~ ~
t ~ 2 [Cl3a27NH3]~
~35 ~ N =
(the dye comprisi~g, as mentio~d earlier~ an isomer mixture) were added ~ith stirring and di~solved at room temp~rature in th~ cour~ of 2 hour~. Then 10 g of a filter aid based on diatomaceous earth were added a~d the mixture wa~ filtered ~hrou~h a pre~ur~ ilter.
The liquid dye preparatio~ thu3 obtai~d wa~ fxe~
of cry~talline matt2r~ a8 wa~ veriied l~nder the microscope at ~bout 700-fold magnification.
15~h~ ~tability o~ thia liquid ~o~mulation at -18~C, ~ 0C a~d ~7C i~ excellent.
Claims (3)
1. Dye preparations containing from 1 to 50% by weight, based on the weight of the preparation, of the dye of the formula
2 [C13H27NH3]?
from 0.1 to 10% by weight, based on the weight of the preparation, of one or more primary, secondary or tertiary aliphatic amines and from 40 to 98.9% by weight, based on the weight of the preparation, of ethanol.
2. Dye preparations as claimed in claim 1, con-taining an amine having at least 8 carbon atoms in the molecule.
from 0.1 to 10% by weight, based on the weight of the preparation, of one or more primary, secondary or tertiary aliphatic amines and from 40 to 98.9% by weight, based on the weight of the preparation, of ethanol.
2. Dye preparations as claimed in claim 1, con-taining an amine having at least 8 carbon atoms in the molecule.
3. The use of the dye preparations of claim 1 in the ink-jet process.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4141761.5 | 1991-12-18 | ||
| DE4141761A DE4141761A1 (en) | 1991-12-18 | 1991-12-18 | LIQUID PREPARATIONS OF A 1: 2 CHROME COMPLEX DYE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2084613A1 true CA2084613A1 (en) | 1993-06-19 |
Family
ID=6447352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002084613A Abandoned CA2084613A1 (en) | 1991-12-18 | 1992-12-04 | Liquid preparations of a 2:1 chromium complex dye |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0547431A1 (en) |
| JP (1) | JPH05302047A (en) |
| CA (1) | CA2084613A1 (en) |
| DE (1) | DE4141761A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0856562A1 (en) * | 1997-01-31 | 1998-08-05 | Hodogaya Chemical Co Ltd | Recording liquid and novel metal complex compound contained therein |
| US7294730B2 (en) * | 2005-11-30 | 2007-11-13 | Xerox Corporation | Colorant compounds |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1263947B (en) * | 1962-04-13 | 1968-03-21 | Basf Ag | Process for the preparation of ammonium salts of chromium complex dyes containing sulfonic acid groups |
| ES287018A1 (en) * | 1962-04-18 | 1963-11-16 | Aziende Colori Naz Affini Acna S P A | A procedure for the preparation of azoic coloring metalized with black tone (Machine-translation by Google Translate, not legally binding) |
| CH524012A (en) * | 1969-02-25 | 1972-01-31 | Ciba Geigy Ag | Process for the continuous dyeing or printing of textile material made of synthetic polyamide |
| DE3143361A1 (en) * | 1981-11-02 | 1983-05-11 | Basf Ag, 6700 Ludwigshafen | METAL COMPLEX DYE |
| BE892137Q (en) * | 1982-02-15 | 1982-08-16 | Sandoz Sa | NEW ASYMMETRIC CHROMIUM COMPLEXES 1: 2 THEIR PREPARATION AND THEIR APPLICATION AS DYES |
-
1991
- 1991-12-18 DE DE4141761A patent/DE4141761A1/en not_active Withdrawn
-
1992
- 1992-12-02 EP EP92120529A patent/EP0547431A1/en not_active Withdrawn
- 1992-12-04 CA CA002084613A patent/CA2084613A1/en not_active Abandoned
- 1992-12-16 JP JP4335927A patent/JPH05302047A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE4141761A1 (en) | 1993-06-24 |
| JPH05302047A (en) | 1993-11-16 |
| EP0547431A1 (en) | 1993-06-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |