CA1048708A - Process for the preparation of disperse dyes having good printing properties for transfer printing - Google Patents
Process for the preparation of disperse dyes having good printing properties for transfer printingInfo
- Publication number
- CA1048708A CA1048708A CA75220587A CA220587A CA1048708A CA 1048708 A CA1048708 A CA 1048708A CA 75220587 A CA75220587 A CA 75220587A CA 220587 A CA220587 A CA 220587A CA 1048708 A CA1048708 A CA 1048708A
- Authority
- CA
- Canada
- Prior art keywords
- printing
- parts
- dyestuff
- liquid medium
- disperse
- 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.)
- Expired
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
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/51—N-substituted amino-hydroxy anthraquinone
- C09B1/515—N-alkyl, N-aralkyl or N-cycloalkyl derivatives
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/003—Transfer printing
- D06P5/004—Transfer printing using subliming dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/003—Transfer printing
- D06P5/004—Transfer printing using subliming dyes
- D06P5/006—Transfer printing using subliming dyes using specified dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Textile Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Coloring (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
PROCESS FOR THE PREPARATION OF DISPERSE DYES HAVING
GOOD PRINTING PROPERTIES FOR TRANSFER PRINTING
Abstract of the Disclosure:
Disperse dyestuffs which are sufficiently capable of subliming for serving in the transfer print process but which yield printing inks of a too high viscosity can be finished to fit the requirements for printing inks for transfer printing by treating said dyestuffs in a liquid medium at a temperature between 50 and 180°C. Thus printing inks of sufficiently low and constant viscosity can be obtained.
GOOD PRINTING PROPERTIES FOR TRANSFER PRINTING
Abstract of the Disclosure:
Disperse dyestuffs which are sufficiently capable of subliming for serving in the transfer print process but which yield printing inks of a too high viscosity can be finished to fit the requirements for printing inks for transfer printing by treating said dyestuffs in a liquid medium at a temperature between 50 and 180°C. Thus printing inks of sufficiently low and constant viscosity can be obtained.
Description
10~ 7l~/~ 0?~
7Q~
The present i.nvention relates to a process for the pre-paration of disperse dyes having good pri.nting properties for transfer printing.
In heat transfer or thermoprintingt disperse dyes havingr sufficient subl;mation capability are worke~ -to printing pastes using binders a~d organic sol~ents, the so-called varnishes, or water and are printed on suitable paper accor-ding to known printing processes, such as gravure pri~ting, offset printing or flexographic printing.
The predominant process is gravure printing in which anhydrous printing inks are used. Under the action of heat, the di.sperse dyestuff is transferred from the paper to the polyester fabric or to a fabric made of other synthetic fibers.
The disperse dyestuff can also be transferred from paper to blended fabrics, for example, polyester-cotton blend, provi.ded that the portion of synthetic fiber in the blend is high enough.
For the preparation of print:ing inks, there may be used pulverulent, pure disperse dyes or disperse dyes mixed with suitable diluents, for example natural or synthetic resins or cellulose derivatives. In this case, it is not necessary that the disperse dyestuff is as finely divided as it is required for its usual fields of application where the fine division required is only achieved by sand or pearl grinding in the presence of di G persing agents. The fine division necessary for the use in printing inks for heat transfer printing i.s achieved, for example, by grinding a dried, pure disperse dyestuff in a pin mill. The mixing agent to be addcd can either be g.~ound at the same time in the pin mill or mixed 29 after gr;.nding wi-th the ground disperse dyestuff in the
7Q~
The present i.nvention relates to a process for the pre-paration of disperse dyes having good pri.nting properties for transfer printing.
In heat transfer or thermoprintingt disperse dyes havingr sufficient subl;mation capability are worke~ -to printing pastes using binders a~d organic sol~ents, the so-called varnishes, or water and are printed on suitable paper accor-ding to known printing processes, such as gravure pri~ting, offset printing or flexographic printing.
The predominant process is gravure printing in which anhydrous printing inks are used. Under the action of heat, the di.sperse dyestuff is transferred from the paper to the polyester fabric or to a fabric made of other synthetic fibers.
The disperse dyestuff can also be transferred from paper to blended fabrics, for example, polyester-cotton blend, provi.ded that the portion of synthetic fiber in the blend is high enough.
For the preparation of print:ing inks, there may be used pulverulent, pure disperse dyes or disperse dyes mixed with suitable diluents, for example natural or synthetic resins or cellulose derivatives. In this case, it is not necessary that the disperse dyestuff is as finely divided as it is required for its usual fields of application where the fine division required is only achieved by sand or pearl grinding in the presence of di G persing agents. The fine division necessary for the use in printing inks for heat transfer printing i.s achieved, for example, by grinding a dried, pure disperse dyestuff in a pin mill. The mixing agent to be addcd can either be g.~ound at the same time in the pin mill or mixed 29 after gr;.nding wi-th the ground disperse dyestuff in the
- 2 -llOl 7~lJ~ 0-,7 ~U ~ ~7 ~ ~
desired ratio. T~le grain sizes achieve~ in the pin mill are, in general, about 10 to 100 times larger than tnose achieved by pearl grinding. A similar degree of fine division is achieved by treating an aqueous suspension of a disperse dyestuff, op-tionally in the presence of the desired diluent, with a dis-solver, a turbulent mixer or homogenizers having a similar effect or also with a ball mill. Very suitable preparations are a]so obtained by treating a mixture o~ dyestuf~ and diluen-t in a kneader.
~owever, practice shows, that some disperse dyestuffs assumed to be suitable for heat transfer printing on account of their relatively poor fastness to sublimation, cannot be used because the anhydrous gravure print:ing inks prepared with th~se dyestuffs are not sufricierltly stable in their vi3cosity and more or less rapidly after~thicken until they become un-usable, or they are, a priori, in the form of a paste uncapable of flowing which can, therefore, not be processed. This un-desired property of some of the disperse dyestuffs supposedly suitable for transfer printing, cannot be overcome even by modifying the binder or varnish preparations. However, in gravure printing mainly carried out in practice, a printing ink of good flowability is absolutely necessary. Moreover, such a printing ink should retain its flowability over a longer period of time, at least for 4 weeks, for only under these conditions rational working is possible.
The present invention provides a process for the pre-paration of disperse dyestuffs which yield printing inks of suitable and constant viscosity for printing transfer printing 29 paper according to the gravure printing process, which process ~34~7~
comprises treating such disperse dyestuffs - which when obtained according to usual processes yield printing inks having viscosity properties unsuit-able for gravure printing - in an aqueous, water-containing or water-free liquid medium in which the disperse dyestuff is essentially insoluble pre-ferably at a temperature within the range of from 50 to 180C, most prefer-ably from 80 to 130C, optionally while stirring.
The process of the invention can be carried out using an already isolated, purified and, optionally, dried disperse dyestuff which was prepared according to the usual methods. Another possible method is to use directly an aqueous, water-containing or water-free suspension formed in the usual preparation method, the addition of one or several organic solvents being a possible advantage. Suitable organic solvents are those in which the dyestuffs shows a solubility as low as possible. Preferably, hydrocarbons are used, especially aliphatic hydrocarbons, but also cyclo-aliphatic or aromatic hydrocarbons which may be halogenated completely or partially, such as petroleum ether boiling within the range of from 50 to about 200C, tetrachlormethane, perchlorethylene, chlorobenzene, dichloro-benzenes, toluene and xylene. Furthermore, solvents miscible with water are used, preferably in mixture with water, such as dimethyl formamide, alkanols of up to 6 carbon atoms, lower dialkyl ketones, such as acetone, dimethyl sulfoxide and lower alkane carboxylic acids, such as acetic acid. The period of the treatment according to the invention at a temperature within the range of from 50C to 180C depends on the nature of the disperse dye-stuff, however, at the temperatures preferably applied, the period required is within the range of 30 minutes to 10 hours. The pH-value of the aqueous medium may vary within ~, ~I OE 71~ C) 5 7 1~4~8 wide limits 5 but it is, preferably to be he]d withiIl the range of 5 to 8, so that sensitive substituents optionally present in the disperse dyestuffs remain unchanged.
In the process according to the invention for the pre-paration of disperse dyestuffs which yield printing inks of suitable and constant viscosity for the printing of transfer printing paper according to the gravure printing process 9 the crystal modification can be chang~ed, for example, as described in German Offenlegungsschrift No. 1,619,535, which is, however, no prerequisite for the disperse dyestuffs treated according to the invention to yield gravure printing inlcs of suitable and constant viscosity.
The viscosity of the printing inks described in the following ~xamples is characterized by the "flow time" meas~
ured according to DIN (German Industrial Standard) 53 211 which they need to run out of a DIN beaker ("Fo d cup") pro-vided with a nozzle of 4 mm diameterO In the case of the anhydrous printing inks obtainable according to the invention this time is less than 35 seconds, preferably 25 seconds or less.
The binders used in the Examples for the preparation of the printing inks have the following composition-Binder A: 12 ~o of ethyl cel1ulose N 7
desired ratio. T~le grain sizes achieve~ in the pin mill are, in general, about 10 to 100 times larger than tnose achieved by pearl grinding. A similar degree of fine division is achieved by treating an aqueous suspension of a disperse dyestuff, op-tionally in the presence of the desired diluent, with a dis-solver, a turbulent mixer or homogenizers having a similar effect or also with a ball mill. Very suitable preparations are a]so obtained by treating a mixture o~ dyestuf~ and diluen-t in a kneader.
~owever, practice shows, that some disperse dyestuffs assumed to be suitable for heat transfer printing on account of their relatively poor fastness to sublimation, cannot be used because the anhydrous gravure print:ing inks prepared with th~se dyestuffs are not sufricierltly stable in their vi3cosity and more or less rapidly after~thicken until they become un-usable, or they are, a priori, in the form of a paste uncapable of flowing which can, therefore, not be processed. This un-desired property of some of the disperse dyestuffs supposedly suitable for transfer printing, cannot be overcome even by modifying the binder or varnish preparations. However, in gravure printing mainly carried out in practice, a printing ink of good flowability is absolutely necessary. Moreover, such a printing ink should retain its flowability over a longer period of time, at least for 4 weeks, for only under these conditions rational working is possible.
The present invention provides a process for the pre-paration of disperse dyestuffs which yield printing inks of suitable and constant viscosity for printing transfer printing 29 paper according to the gravure printing process, which process ~34~7~
comprises treating such disperse dyestuffs - which when obtained according to usual processes yield printing inks having viscosity properties unsuit-able for gravure printing - in an aqueous, water-containing or water-free liquid medium in which the disperse dyestuff is essentially insoluble pre-ferably at a temperature within the range of from 50 to 180C, most prefer-ably from 80 to 130C, optionally while stirring.
The process of the invention can be carried out using an already isolated, purified and, optionally, dried disperse dyestuff which was prepared according to the usual methods. Another possible method is to use directly an aqueous, water-containing or water-free suspension formed in the usual preparation method, the addition of one or several organic solvents being a possible advantage. Suitable organic solvents are those in which the dyestuffs shows a solubility as low as possible. Preferably, hydrocarbons are used, especially aliphatic hydrocarbons, but also cyclo-aliphatic or aromatic hydrocarbons which may be halogenated completely or partially, such as petroleum ether boiling within the range of from 50 to about 200C, tetrachlormethane, perchlorethylene, chlorobenzene, dichloro-benzenes, toluene and xylene. Furthermore, solvents miscible with water are used, preferably in mixture with water, such as dimethyl formamide, alkanols of up to 6 carbon atoms, lower dialkyl ketones, such as acetone, dimethyl sulfoxide and lower alkane carboxylic acids, such as acetic acid. The period of the treatment according to the invention at a temperature within the range of from 50C to 180C depends on the nature of the disperse dye-stuff, however, at the temperatures preferably applied, the period required is within the range of 30 minutes to 10 hours. The pH-value of the aqueous medium may vary within ~, ~I OE 71~ C) 5 7 1~4~8 wide limits 5 but it is, preferably to be he]d withiIl the range of 5 to 8, so that sensitive substituents optionally present in the disperse dyestuffs remain unchanged.
In the process according to the invention for the pre-paration of disperse dyestuffs which yield printing inks of suitable and constant viscosity for the printing of transfer printing paper according to the gravure printing process 9 the crystal modification can be chang~ed, for example, as described in German Offenlegungsschrift No. 1,619,535, which is, however, no prerequisite for the disperse dyestuffs treated according to the invention to yield gravure printing inlcs of suitable and constant viscosity.
The viscosity of the printing inks described in the following ~xamples is characterized by the "flow time" meas~
ured according to DIN (German Industrial Standard) 53 211 which they need to run out of a DIN beaker ("Fo d cup") pro-vided with a nozzle of 4 mm diameterO In the case of the anhydrous printing inks obtainable according to the invention this time is less than 35 seconds, preferably 25 seconds or less.
The binders used in the Examples for the preparation of the printing inks have the following composition-Binder A: 12 ~o of ethyl cel1ulose N 7
3 % of ethyl cellulose N 22 10 % of ethylene glycol monoethyl ether 25 % of ethyl acetate 50 % of ethanol Binder ~: 12 p of ethyl cellulose N 7 29 3 % of ethyl cellulose N 22 HOE 74/~
~)4~7~
10 Cj~ of oth-ylcne glycol monoethyl ether 75 /6lo of ethanol.
"Ethyl cellu1ose N 7" and "N 22" are ce]lulose et}lyl ethers an~ comlnercial products of ~Iessrs. Hercules Inc., 1~
mington~ Dela. 19~,9~/USA. The numbers indicate the average viscosity of a 5 ~p solution in a 4 : 1 mixture of toluene and ethanol at 25C in cP.
The cellulose acetobutyrates used in the ~xamples are commercial produc-ts of ~lessrs. Eastman Kodak Co., Kingspolt, Tenn. 37662/USA and are distinguished as follows:
Cellulose acetobu~ra-teC~, 551-0.2: acetyl content: 2.0 'p butyryl content: 53 ~j', Cellulose acetobutyrate CA~ 3~1-2: acetyl content: 13.5 /' butyry?. content: 37 ~' The process of the invention is preferably applied for dyestuffs of the general formula X O 0~
A ~ Hal~_ ~
y 0 NH2~aRa in which one of the radicals X and Y is a hydroxy group and the other one is a radical of the formula -NH2 bR'b, R and R
being-preferably identical - alkyl groups o~ 1 or 2 carbon atoms, preferably methyl groups, Hal stands for chlorine atoms or, preferably, bromine atoms,-~is a number of O to 2, preferably 1, and a and b each is a number from O to 2, a ~ b gi~ing O to 3, preferably 0.5 to 2, especially 0.5 to 1~
~9 Such dyestuffs are, for example, described in German Patents ~101, ~ O `' ~
1'~4~7~P8 Nos. 1,029,506, 1,150,li77 and 1,162,961.
The dyestuffs rererred to in tlle Examples are prepared a5 follows; the parts bei.ng by weight:
(1) German I'atent N'o. 1,162,961, ExaMple 2) 27 Parts of 4,~-diamino-1,5-dihydroxyanthraq1linone were dissolved at 40C in 100 parts of 100 % sulfuric acid ("monohydrate"), 10 parts of polyphosphoric acid we~-e added and then, 3 parts of para~formaldehyde were intro-duced at 30 C while stirring. The mixturc was stirred for 8 hours at 30 - 35C and the reaction mixture was carefully poured onto ice. The dyestuff obtained ~a~
suction-filtered and washed un-til neutral.
(2) (German. Patent No. 1,150,1~77, Example 1) 14 Parts of 1l~8-diamino-1~5~-dihydro~yanthraquiIlone were dissolved at 40C in 68 parts of 100 o,h sul.furic acid, the solution was allowed to cool and 1.5 parts of paraform-aldehyde were introduced portionwise while stirring so that the temperature did not exceed 35C. Then, the mixture was stirred for 4 to 10 hours at 30 to 35C and carefully poured onto ice. The precipitate was suction-filtered and washed until neutral. After drying, 14.5 parts of a blue dyestuff were obtained.
(3) (German Patent No. 1,029,506, Example 2) 27 Parts of 4,8-diamino-1,5-di.hydroxyanthraquinone and 10 parts of boric acid were dissolved in 250 parts of 100 % sulfuric acid to ~hich solution 0.1 part of iodine and 10 parts of bromine were added. Then, the solution was st;rred at 50C until the bromi.ne had been consumed, 29 then the reaction mixture was poured onto ice, the -- 7 ~
~ o~/~? 057 1¢~4~37~8 preciI)itate was suction-filtered and washed un"il neutral.
So, 35 parts of a blue d~escuff were obtained which con-tained about 25 % of bromine.
~)4~7~
10 Cj~ of oth-ylcne glycol monoethyl ether 75 /6lo of ethanol.
"Ethyl cellu1ose N 7" and "N 22" are ce]lulose et}lyl ethers an~ comlnercial products of ~Iessrs. Hercules Inc., 1~
mington~ Dela. 19~,9~/USA. The numbers indicate the average viscosity of a 5 ~p solution in a 4 : 1 mixture of toluene and ethanol at 25C in cP.
The cellulose acetobutyrates used in the ~xamples are commercial produc-ts of ~lessrs. Eastman Kodak Co., Kingspolt, Tenn. 37662/USA and are distinguished as follows:
Cellulose acetobu~ra-teC~, 551-0.2: acetyl content: 2.0 'p butyryl content: 53 ~j', Cellulose acetobutyrate CA~ 3~1-2: acetyl content: 13.5 /' butyry?. content: 37 ~' The process of the invention is preferably applied for dyestuffs of the general formula X O 0~
A ~ Hal~_ ~
y 0 NH2~aRa in which one of the radicals X and Y is a hydroxy group and the other one is a radical of the formula -NH2 bR'b, R and R
being-preferably identical - alkyl groups o~ 1 or 2 carbon atoms, preferably methyl groups, Hal stands for chlorine atoms or, preferably, bromine atoms,-~is a number of O to 2, preferably 1, and a and b each is a number from O to 2, a ~ b gi~ing O to 3, preferably 0.5 to 2, especially 0.5 to 1~
~9 Such dyestuffs are, for example, described in German Patents ~101, ~ O `' ~
1'~4~7~P8 Nos. 1,029,506, 1,150,li77 and 1,162,961.
The dyestuffs rererred to in tlle Examples are prepared a5 follows; the parts bei.ng by weight:
(1) German I'atent N'o. 1,162,961, ExaMple 2) 27 Parts of 4,~-diamino-1,5-dihydroxyanthraq1linone were dissolved at 40C in 100 parts of 100 % sulfuric acid ("monohydrate"), 10 parts of polyphosphoric acid we~-e added and then, 3 parts of para~formaldehyde were intro-duced at 30 C while stirring. The mixturc was stirred for 8 hours at 30 - 35C and the reaction mixture was carefully poured onto ice. The dyestuff obtained ~a~
suction-filtered and washed un-til neutral.
(2) (German. Patent No. 1,150,1~77, Example 1) 14 Parts of 1l~8-diamino-1~5~-dihydro~yanthraquiIlone were dissolved at 40C in 68 parts of 100 o,h sul.furic acid, the solution was allowed to cool and 1.5 parts of paraform-aldehyde were introduced portionwise while stirring so that the temperature did not exceed 35C. Then, the mixture was stirred for 4 to 10 hours at 30 to 35C and carefully poured onto ice. The precipitate was suction-filtered and washed until neutral. After drying, 14.5 parts of a blue dyestuff were obtained.
(3) (German Patent No. 1,029,506, Example 2) 27 Parts of 4,8-diamino-1,5-di.hydroxyanthraquinone and 10 parts of boric acid were dissolved in 250 parts of 100 % sulfuric acid to ~hich solution 0.1 part of iodine and 10 parts of bromine were added. Then, the solution was st;rred at 50C until the bromi.ne had been consumed, 29 then the reaction mixture was poured onto ice, the -- 7 ~
~ o~/~? 057 1¢~4~37~8 preciI)itate was suction-filtered and washed un"il neutral.
So, 35 parts of a blue d~escuff were obtained which con-tained about 25 % of bromine.
(4) (German Patent ~o. 1,162,961, ~xample 1) 27 Parts of a miYture of 55 parts of 4,8-diamino-1,5-di-hydro~y-anthraquinone and 45 parts of 4,5-diamino-1,8-di-hydroxyanthraquinone were dissol~red at 40 C in 100 parts of 100 G/~ sulfuric acid, the mixture was allowed to cool and into the solution obtained a previously prepared mixture of 100 parts of 100 o~h sulfuric acid, 3 parts of paraform-aldehyde, 5 parts of phosphorous pentox:ide, and 20 parts of N-methylacetam~de was added dropwise at 30 -to 35 C wllile stirring. Then, the solution was again stirred at t~lat temperature for 4 to 10 hours and the reaction IniY.ture was caref`ully put onto ice. The precipitate obta:ined was suction-filtered and washed until neutral.
E X A M P I E S:
E X A M P L E
10 Parts of the disperse dyestuff (I) in the form of 30 parts of the fi]ter cake, which had been washed until neutral were suspended in 80 parts of water and heated to 130C for 1 hour in the stirring autoclave. After cooling, 17.3 parts of cellulose acetobutyrate CAB 551-0.2 and 1.3 parts of cellulose aceto-butyrate CAB 381-2 were added to the dyestuff suspension and passed twice through a colloid mill. Suction-filtering and drying in the vacuum drying cabinet at 60C followed. The dry filter cake disintegrated to loose granules, 5 parts of uhich were worked into 95 parts of binder A in an attritor.
29 Immediately after its preparation, this printing ink showed a
E X A M P I E S:
E X A M P L E
10 Parts of the disperse dyestuff (I) in the form of 30 parts of the fi]ter cake, which had been washed until neutral were suspended in 80 parts of water and heated to 130C for 1 hour in the stirring autoclave. After cooling, 17.3 parts of cellulose acetobutyrate CAB 551-0.2 and 1.3 parts of cellulose aceto-butyrate CAB 381-2 were added to the dyestuff suspension and passed twice through a colloid mill. Suction-filtering and drying in the vacuum drying cabinet at 60C followed. The dry filter cake disintegrated to loose granules, 5 parts of uhich were worked into 95 parts of binder A in an attritor.
29 Immediately after its preparation, this printing ink showed a
5 7 i341~7~?~3 flow time of 1~ seconds and. Was excellently suitable for printing heat trans~`er printing papers according to the gravure printing process. 4fter a 7 days~ ~torage at 50 C, which approxinlately correspond.s to a storage of 4 we~ks at room temperatl~re, the flow time of the printing ink was 19 seconds.
However~ when the pr;ntillg ink was prepared from a pre-paration having the same composition and bei~g prepared. in the same manner, but which conta.ined the d.i.sperse dye (1) llOt being after-treated in the autoclave, -the flow time of the printing ink was 25 seconds immediately after the preparation of the pri.nting ink. Afte3- a 7 days' stor~ge at 50C tlle printing il-lk .had completely thickened., could not flow any longer and had become unusable.
10 Parts of dry dyestuff (2) were heated in 100 parts of perchloroethylene to 100C for 2 hours while stirring. Then, the perchloroethylene was eliminated by steam distillation, the dyestuff was suction-filtered from the aqueous suspension obtained and dried at 60C in vacuo. This dyestuff was ground in a pin mill. 1.75 parts of the pulverulent dyestuff were processed with 98.25 parts of binder A in an attritor to yield a printing ink which showed a flow time of 24 seconds and excellently suits for printing heat transfer paper according to the gravure printing process. After a storage time of 7 days at 50C, the viscosity of the prinling ink re~lained unchanged.
However, when 1.75 parts of dyestuff (2) not being *reated with perchloroethylene were used for the preparation of the printing ink the resulting printing ink showed a flow time of 29 26 seconds. After a 7 days~ storage at 50C, the printi.ng ink - 9 _ ~~_ 7~1 ` 0-~7 4f~7~'B
had completel.)~ thickened. Th~ viscosity could not be de-termined any longer.
E X A M P L ~, 3 .
10 Parts of disperse dye~stuff (2) were introduced in the form of the dri,ed filter cake in a mix-ture of 90 parts of water and 10 parts of dimethyl formamide and heated to 100C fo-r l~ hours. Then, the dyestuff waS suction-fi,ltered, washed alld dried at 60C in vacuo. 7.5 par-ts of this dyestuff were grc,und with 16.4 parts of cellulose acetobutyrate CAE 551-0.2 arld 1.1 parts of cellulose acetobutyrate C~B 381-~ iIl a pin mi.ll, After incorporating 5 parts of this preparati.on into 95 par-cs of binder B by means of` a usual dispersing aggregate, the printlng ink showed a flow t:ime of 25 seconds ~nd s~ited very well for printing heat transfe:r paper accordiIlg to the gr3vure printing process. After a storage time of 7 clays at 50C, the viscosity remained unchanged. ~lso :in the ,following storage for
However~ when the pr;ntillg ink was prepared from a pre-paration having the same composition and bei~g prepared. in the same manner, but which conta.ined the d.i.sperse dye (1) llOt being after-treated in the autoclave, -the flow time of the printing ink was 25 seconds immediately after the preparation of the pri.nting ink. Afte3- a 7 days' stor~ge at 50C tlle printing il-lk .had completely thickened., could not flow any longer and had become unusable.
10 Parts of dry dyestuff (2) were heated in 100 parts of perchloroethylene to 100C for 2 hours while stirring. Then, the perchloroethylene was eliminated by steam distillation, the dyestuff was suction-filtered from the aqueous suspension obtained and dried at 60C in vacuo. This dyestuff was ground in a pin mill. 1.75 parts of the pulverulent dyestuff were processed with 98.25 parts of binder A in an attritor to yield a printing ink which showed a flow time of 24 seconds and excellently suits for printing heat transfer paper according to the gravure printing process. After a storage time of 7 days at 50C, the viscosity of the prinling ink re~lained unchanged.
However, when 1.75 parts of dyestuff (2) not being *reated with perchloroethylene were used for the preparation of the printing ink the resulting printing ink showed a flow time of 29 26 seconds. After a 7 days~ storage at 50C, the printi.ng ink - 9 _ ~~_ 7~1 ` 0-~7 4f~7~'B
had completel.)~ thickened. Th~ viscosity could not be de-termined any longer.
E X A M P L ~, 3 .
10 Parts of disperse dye~stuff (2) were introduced in the form of the dri,ed filter cake in a mix-ture of 90 parts of water and 10 parts of dimethyl formamide and heated to 100C fo-r l~ hours. Then, the dyestuff waS suction-fi,ltered, washed alld dried at 60C in vacuo. 7.5 par-ts of this dyestuff were grc,und with 16.4 parts of cellulose acetobutyrate CAE 551-0.2 arld 1.1 parts of cellulose acetobutyrate C~B 381-~ iIl a pin mi.ll, After incorporating 5 parts of this preparati.on into 95 par-cs of binder B by means of` a usual dispersing aggregate, the printlng ink showed a flow t:ime of 25 seconds ~nd s~ited very well for printing heat transfe:r paper accordiIlg to the gr3vure printing process. After a storage time of 7 clays at 50C, the viscosity remained unchanged. ~lso :in the ,following storage for
6 weelcs at room temperature, the viscosity of this printing ink did not change.
However, when the printing ink was prepared by means of a preparation having the same composition with the difference of containing a dyestuff (2) which had not been after-trea-ted ~rith water-containing dimethyl formamide5 the flow time was 45 seconds. Already after 24 hours, this printing ink had thickened to be completely unusable and the viscosity could not be determined any longer.
10 Parts of dyestuff (3) in the form o`f 35 parts of the filter cake washed until neutral were heated in 75 parts of 29 water in the autoclave to 130C for 3 hours while stirring.
--o~7~ o >z ~4~
~fter cooling, t~-,c dyestuff was suction-f;.l-tered, dried at 60 C in vacuo and pulverized i~ a pin mill. ~sing 1.75 parts of this dyestuff powder and 98.25 parts of binder E, a printing ink was obtained in the attritor having a flow tim~ of 17 seconds which excellently suited for prin-ting heat transler printing paper according to the gravure pri.nting process.
After a storage period-of 7 days at 50C the printing ink hacl a flow time of 24 seconds.
However, when the printing inlc was prepared using the dye.stuff (3) which had not been treated in the autoclave, dried.
and ground i.n the pin mill, the printi.ng in]c thickened so much a]ready during its preparation in the attritor that it could ILOt be used at all. The viscosity could not be meas1lred.
E X J'~ ~ P L E 5 10 Parts of the disperse dyestuIf (4~ in the form of the filter cake washed neutral and. dried were heated to 110 C
during 2 hours in 100 parts of chlorobenzene, while stirring.
Then, the chlorobenzene was eliminated by steam distillation.
18.6 parts of rosin (colophony~ were added to the aqueous dyestuff suspension, the whole being passed through a colloid mill.
After suction-filtering and drying at 60C in vacuo 9 a preparation in the form of loose granules was obtained.
5 parts of this preparation yielded, upon being worked into 95 parts of binder A, a printing ink of a flow time of 28 seconds which suited very much for printing heat transfer printing paper according to the gravure printing process.
After a 7 days~ storage at 50C, the flow time was 32 second.s.
- 29 However, when the printi.ng ink was prepared using a .
~I~JI~ ~/r~
preparat:ion of the same composition, wit}l the difference -that it conta~ned l,-e i-uf~ ) which h~d not been treated with chloro~
benzene, the flo~.~ time was 41 secon(is. ~*ter a storage period of 7 days at 50 C, th~t printing illlc had thickened ancl could no longer be usecl for printing. Its viscosi-ty could no 7onger be deterniined.
E X A ~l P I E 6 . . _ - 10 Parts of dyestuff (3) in the I`orm of llo parts of filtecake were heated to 130 C for 1 hour in 70 parts of water ln the autoclave, while stirring. After cool:ing, there were added to the aqueous dyestuff suspension 17.3 parts of cellulosr-acetobutyrate C~B 551-0.2 and 1.3 parts of cellulose aceto-butyrate C~13 381-2 and the whole was ground in a colloid mill.
A~ter suc(:io~ i.ltering5 the fi~ter caXe ~a.s drled at 60C i~
vacuo. 5 parts of this dye~tuff preparation were incorporated into 95 parts of binder A by means of an attritor~
The flow time of the printing ink was 21 seconcls. Af`ter a storage period of 7 days at 50C, the flow time had not changed and the printing ink still suited excellent;y for printing heat transfer printing paper accordin~ to the gravure printing process.
Even when the storage period was extended to seveIal week.s at room temperature, the viscosi-ty did not increase.
When in the preparation of the printing ink a preparation was used which had the same composition with the di~ference~
however, that it contained dyestuff (3) which had not been treated in the autoclave, the flow time of ~the printing ink immediately aIter preparation was 20 second~, increasing to 29 3~ seconds after a storage of 7 days at 50 C. The viscosity ~/
4~7 ~ 8 ~ creasecl cluring su~secluent stolage a-t room temperature reach:ing after a ~ days~ storage at ~0 (` and a 2 weeks~ s-torage at roo~
temperature a c~egree of viscosity that couicl not be determilJcd any longer and the ~rintirlg ink was spoilt for use ln printin~r.
However, when the printing ink was prepared by means of a preparation having the same composition with the difference of containing a dyestuff (2) which had not been after-trea-ted ~rith water-containing dimethyl formamide5 the flow time was 45 seconds. Already after 24 hours, this printing ink had thickened to be completely unusable and the viscosity could not be determined any longer.
10 Parts of dyestuff (3) in the form o`f 35 parts of the filter cake washed until neutral were heated in 75 parts of 29 water in the autoclave to 130C for 3 hours while stirring.
--o~7~ o >z ~4~
~fter cooling, t~-,c dyestuff was suction-f;.l-tered, dried at 60 C in vacuo and pulverized i~ a pin mill. ~sing 1.75 parts of this dyestuff powder and 98.25 parts of binder E, a printing ink was obtained in the attritor having a flow tim~ of 17 seconds which excellently suited for prin-ting heat transler printing paper according to the gravure pri.nting process.
After a storage period-of 7 days at 50C the printing ink hacl a flow time of 24 seconds.
However, when the printing inlc was prepared using the dye.stuff (3) which had not been treated in the autoclave, dried.
and ground i.n the pin mill, the printi.ng in]c thickened so much a]ready during its preparation in the attritor that it could ILOt be used at all. The viscosity could not be meas1lred.
E X J'~ ~ P L E 5 10 Parts of the disperse dyestuIf (4~ in the form of the filter cake washed neutral and. dried were heated to 110 C
during 2 hours in 100 parts of chlorobenzene, while stirring.
Then, the chlorobenzene was eliminated by steam distillation.
18.6 parts of rosin (colophony~ were added to the aqueous dyestuff suspension, the whole being passed through a colloid mill.
After suction-filtering and drying at 60C in vacuo 9 a preparation in the form of loose granules was obtained.
5 parts of this preparation yielded, upon being worked into 95 parts of binder A, a printing ink of a flow time of 28 seconds which suited very much for printing heat transfer printing paper according to the gravure printing process.
After a 7 days~ storage at 50C, the flow time was 32 second.s.
- 29 However, when the printi.ng ink was prepared using a .
~I~JI~ ~/r~
preparat:ion of the same composition, wit}l the difference -that it conta~ned l,-e i-uf~ ) which h~d not been treated with chloro~
benzene, the flo~.~ time was 41 secon(is. ~*ter a storage period of 7 days at 50 C, th~t printing illlc had thickened ancl could no longer be usecl for printing. Its viscosi-ty could no 7onger be deterniined.
E X A ~l P I E 6 . . _ - 10 Parts of dyestuff (3) in the I`orm of llo parts of filtecake were heated to 130 C for 1 hour in 70 parts of water ln the autoclave, while stirring. After cool:ing, there were added to the aqueous dyestuff suspension 17.3 parts of cellulosr-acetobutyrate C~B 551-0.2 and 1.3 parts of cellulose aceto-butyrate C~13 381-2 and the whole was ground in a colloid mill.
A~ter suc(:io~ i.ltering5 the fi~ter caXe ~a.s drled at 60C i~
vacuo. 5 parts of this dye~tuff preparation were incorporated into 95 parts of binder A by means of an attritor~
The flow time of the printing ink was 21 seconcls. Af`ter a storage period of 7 days at 50C, the flow time had not changed and the printing ink still suited excellent;y for printing heat transfer printing paper accordin~ to the gravure printing process.
Even when the storage period was extended to seveIal week.s at room temperature, the viscosi-ty did not increase.
When in the preparation of the printing ink a preparation was used which had the same composition with the di~ference~
however, that it contained dyestuff (3) which had not been treated in the autoclave, the flow time of ~the printing ink immediately aIter preparation was 20 second~, increasing to 29 3~ seconds after a storage of 7 days at 50 C. The viscosity ~/
4~7 ~ 8 ~ creasecl cluring su~secluent stolage a-t room temperature reach:ing after a ~ days~ storage at ~0 (` and a 2 weeks~ s-torage at roo~
temperature a c~egree of viscosity that couicl not be determilJcd any longer and the ~rintirlg ink was spoilt for use ln printin~r.
Claims (15)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A process for preparing disperse dyestuffs capable of yield-ing printing inks useful for transfer printing which comprises treating a disperse dyestuff capable of subliming but yielding printing inks of too high or inconstant viscosity in a liquid medium in which the disperse dye-stuff is essentially insoluble at a temperature of 50 to 180°C.
2. A process as defined in claim 1, wherein the temperature is 80 to 130°C.
3. A process as defined in claim 1, wherein the liquid medium is an aqueous medium.
4. A process as defined in claim 1, wherein the liquid medium is an organic medium.
5. A process as defined in claim 1, wherein the liquid medium is a water containing organic water-miscible solvent.
6. A process as defined in claim 1, wherein the liquid medium is an aliphatic hydrocarbon boiling between 50 and 200°C., a chlorinated aliphatic hydrocarbon of 1 to 4 carbon atoms, toluene, xylene, chlorobenzene, dichlorobenzene or a mixture thereof.
7. A process as defined in claim 1, wherein the liquid medium is dimethyl, formamide, an alkanol of 1 to 6 carbon atoms, acetone, di-methylsulfoxide, an alkanoic acid of 1 to 4 carbon atoms or a mixture there-of or a mixture of one or more of said solvents with water.
8. A process as defined in claim 1, wherein the dyestuff is stirred in the liquid medium.
9. A process as defined in claim 1, wherein the dyestuff has the formula wherein one of the substituents X and Y is hydroxy and the other is -NH2-b R'b' and R' are equal or different groups selected from methyl and ethyl, a and b are numbers from zero to 2, the sum of which is zero to 3, Hal is chlorine or bromine and x is a number of zero to 2.
10. A process as defined in claim 9, wherein R and R' are methyl.
11. A process as defined in claim 9, wherein the sum of a and b is 0.5 to 2.
12. A process as defined in claim 9, wherein the sum of a and b is 0.5 to 1.
13. A process as defined in claim 9, wherein Hal is bromine.
14. A process as defined in claim 9, wherein x is 1.
15. An unhydrous printing ink of a constant viscosity useful for printing paper for the transfer printing process containing a dyestuff obtained by a process as defined in claim 1.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742408899 DE2408899B1 (en) | 1974-02-23 | 1974-02-23 | Process for the production of disperse dyes, which result in printing inks with a suitable and constant viscosity for printing transfer printing paper by the gravure printing process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1048708A true CA1048708A (en) | 1979-02-20 |
Family
ID=5908353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA75220587A Expired CA1048708A (en) | 1974-02-23 | 1975-02-21 | Process for the preparation of disperse dyes having good printing properties for transfer printing |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS50121323A (en) |
| AR (1) | AR205183A1 (en) |
| BE (1) | BE825880A (en) |
| BR (1) | BR7501085A (en) |
| CA (1) | CA1048708A (en) |
| CH (1) | CH610345A5 (en) |
| DE (1) | DE2408899B1 (en) |
| DK (1) | DK67275A (en) |
| FR (1) | FR2262087B1 (en) |
| GB (1) | GB1504583A (en) |
| IT (1) | IT1031972B (en) |
| LU (1) | LU71892A1 (en) |
| NL (1) | NL7501906A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2714768C3 (en) * | 1977-04-02 | 1979-09-13 | Bayer Ag, 5090 Leverkusen | Transfer printing process |
-
1974
- 1974-02-23 DE DE19742408899 patent/DE2408899B1/en not_active Ceased
-
1975
- 1975-01-01 AR AR25771875A patent/AR205183A1/en active
- 1975-02-18 NL NL7501906A patent/NL7501906A/en not_active Application Discontinuation
- 1975-02-20 CH CH212175A patent/CH610345A5/en not_active IP Right Cessation
- 1975-02-21 JP JP50021080A patent/JPS50121323A/ja active Pending
- 1975-02-21 LU LU71892A patent/LU71892A1/xx unknown
- 1975-02-21 CA CA75220587A patent/CA1048708A/en not_active Expired
- 1975-02-21 IT IT2055075A patent/IT1031972B/en active
- 1975-02-21 DK DK67275A patent/DK67275A/da unknown
- 1975-02-21 BR BR7501085A patent/BR7501085A/en unknown
- 1975-02-24 GB GB762375A patent/GB1504583A/en not_active Expired
- 1975-02-24 BE BE153652A patent/BE825880A/en unknown
- 1975-02-24 FR FR7505618A patent/FR2262087B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE825880A (en) | 1975-08-25 |
| JPS50121323A (en) | 1975-09-23 |
| NL7501906A (en) | 1975-08-26 |
| DK67275A (en) | 1975-10-20 |
| IT1031972B (en) | 1979-05-10 |
| CH610345A5 (en) | 1979-04-12 |
| LU71892A1 (en) | 1977-01-05 |
| FR2262087B1 (en) | 1980-09-12 |
| FR2262087A1 (en) | 1975-09-19 |
| BR7501085A (en) | 1975-12-02 |
| DE2408899B1 (en) | 1975-10-16 |
| GB1504583A (en) | 1978-03-22 |
| AR205183A1 (en) | 1976-04-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3759733A (en) | Pigment compositions | |
| US2007382A (en) | Production of dispersions | |
| EP1694776B2 (en) | Disperse dyes | |
| JPS58189259A (en) | Aqueous dye blend of water-soluble or water hardly soluble dyes | |
| US6682573B2 (en) | Azo disperse dye mixtures | |
| KR20080011317A (en) | Disperse azo dyes and mixtures comprising these disperse azo dyes | |
| US5024698A (en) | Monoazo pigment compositions | |
| US4207067A (en) | Transfer dye | |
| US4073615A (en) | Stable dye solution | |
| EP1499683A1 (en) | Compositions and methods for imparting improved rheology on pigment based inks and paints | |
| EP0300626B1 (en) | Disperse dye mixture | |
| US4323396A (en) | Process for the preparation of pigment formulations and their use | |
| CA1048708A (en) | Process for the preparation of disperse dyes having good printing properties for transfer printing | |
| US4145182A (en) | Process for the preparation of disperse dyes having good printing properties for transfer printing | |
| US3153564A (en) | Dispersing dispersed acetate dyes and a lignin sulfonate alkyl naphthalene sulfonate and sulfo carboxylic acid alkyl ester mixture therefor | |
| US4523923A (en) | Solid disperse dye formulations containing non-ionic dispersants for transfer printing inks | |
| JPS587454A (en) | Metamorphosis stable to disperse dye dying, manufacture and dyeing or printing method thereby | |
| US4186029A (en) | Aqueous dyestuff dispersions | |
| TW499465B (en) | Dye mixtures and their uses | |
| JPH06184480A (en) | Ink composition for ink jet print | |
| EP0030695A1 (en) | Process for printing synthetic, hydrophobic fibrous material by the transfer printing principle | |
| JPS5845509B2 (en) | Transfer printing method for polyester moldings | |
| US2007386A (en) | Iproduction of dispersions | |
| US4306874A (en) | Process for printing synthetic, hydrophobic fiber material in accordance with the principle of transfer printing | |
| US2346957A (en) | Printing composition |