US3795479A - Fixing prints of stabilized azoic and reactive dyes on cellulose and cellulose/polyester - Google Patents

Fixing prints of stabilized azoic and reactive dyes on cellulose and cellulose/polyester Download PDF

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Publication number
US3795479A
US3795479A US00189043A US3795479DA US3795479A US 3795479 A US3795479 A US 3795479A US 00189043 A US00189043 A US 00189043A US 3795479D A US3795479D A US 3795479DA US 3795479 A US3795479 A US 3795479A
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Prior art keywords
acid
steaming
vapor
dyestuffs
cellulose
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US00189043A
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English (en)
Inventor
E Feess
W Gronen
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Hoechst AG
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Hoechst AG
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Priority claimed from DE19702050631 external-priority patent/DE2050631C3/de
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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34Material containing ester groups
    • D06P3/52Polyesters
    • D06P3/54Polyesters using dispersed dyestuffs
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06BTREATING TEXTILE MATERIALS USING LIQUIDS, GASES OR VAPOURS
    • D06B19/00Treatment of textile materials by liquids, gases or vapours, not provided for in groups D06B1/00 - D06B17/00
    • D06B19/0005Fixing of chemicals, e.g. dyestuffs, on textile materials
    • D06B19/0029Fixing of chemicals, e.g. dyestuffs, on textile materials by steam
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06BTREATING TEXTILE MATERIALS USING LIQUIDS, GASES OR VAPOURS
    • D06B19/00Treatment of textile materials by liquids, gases or vapours, not provided for in groups D06B1/00 - D06B17/00
    • D06B19/0005Fixing of chemicals, e.g. dyestuffs, on textile materials
    • D06B19/0029Fixing of chemicals, e.g. dyestuffs, on textile materials by steam
    • D06B19/0035Fixing of chemicals, e.g. dyestuffs, on textile materials by steam the textile material passing through a chamber
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34Material containing ester groups
    • D06P3/52Polyesters
    • D06P3/56Preparing azo dyes on the material
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58Material containing hydroxyl groups
    • D06P3/60Natural or regenerated cellulose
    • D06P3/66Natural or regenerated cellulose using reactive dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58Material containing hydroxyl groups
    • D06P3/60Natural or regenerated cellulose
    • D06P3/68Preparing azo dyes on the material
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/82Textiles which contain different kinds of fibres
    • D06P3/8204Textiles which contain different kinds of fibres fibres of different chemical nature
    • D06P3/8223Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916Natural fiber dyeing
    • Y10S8/918Cellulose textile

Definitions

  • ABSTRACT I material according to a known two-phase-fixation process for fixing the reactive dyestuffs and finishing it as usual by washing, soaping and rinsing as well as'a process comprising the said very rapid fixation process of stabilized dyeing preparations forming azo dystuffs, by means of acid steam except for the use of reactive dyestuffs and for the use of the two-phase-fixation process which leads to dyeings of azo dyestuffs and of reactive dyestuffs of good fastenesses and brilliancy obtained in a very short time by means of a fully continuous process of fixing azo and reactive dyestuffs and of after-treatment the dyed material.
  • the present invention relates to a process for printing and continuous fixation of stabilized dyeing preparations forming azo dyestuffs, and of reactive dyestuffs on textile materials containing cellulose or consisting exclusively of cellulose material.
  • stabilized dyeing preparations which contain as substantial constituent a naphthol derivative and stabilized diazo compounds; by printing the fabric with different types of this dyeing preparations, various shades may be produced on the fibre, which permits independence from the respective bottom.
  • the mentioned stabilized diazo compounds are for example diazo-amino compounds obtained by reacting the non-stable diazonium salts with for example cyanamide, anthranilic acid or other amines. They are sufficiently stable in the alkaline medium for being combined with naphtholate solutions. It is also possible to convert the diazotized amines into anti-diazotate compounds with the aid of strong alkalis, and their mixtures with naphtholates lead to similar, however less stable dyeing preparations.
  • Dyeing preparations of the mentioned type are in commerce since many years; their stabilized diazo compounds may be converted again on the fibre into the diazotized base by steaming processes, in which case coupling takes place with the coupling component, preferably with a naphthol'derivative, to form the dyestuff. If steaming is effecting in an acidic medium, more brilliant shades are obtained than in the case of neutral steaming. Depending on the steaming devices used, recommendations found in literature are for steaming processes of 35 or of 5-7 minutes. However, these steaming periods are so long that a continuous working, for example continuous steaming and washing may hardly be realized in practice if the best possible speeds of the. washing process shall be achieved.
  • the long steaming periods are due to the fact that in the case of the usual steamers of rather big volume, the content of acid of the steaming atmosphere decreases in close vicinity to the fabric printed with an alkaline agent and that the fabric has not sufficient amount of acid available for developing the diazonium salts and the azo dyestuffs.
  • the steaming periods are too long to permit reactive dyestuffs, applied on the fibre simultaneously with the dyeing preparations or by overprinting to be fixed subsequently to this steaming process in a continuous two-phase-fast-fixing process.
  • This method according to the invention also permits to utilize the acid in the best possible way, whereas in the commonly used steaming devices, large portion of the acid escapes with the exhaust steam from the steamer without being completely utilized.
  • a 5 second-steaming period if thin fabrics are treated a shorter steaming time is sufficient to ensure a complete splitting of the stable diazo compound and fully developing of the azo dyestuff.
  • the steaming aggregates used for these short steaming processes are therefore very small, so that devices of this kind may be intercalated without difficulty into the continuous development of a production process.
  • the present invention relates to a process for printing and continuous fixation of stabilized dyeing preparations forming azo dyestuffs, and of reactive dyestuffs on textile material containing cellulose or consisting exclusively of cellulose material.
  • This process is characterized by the fact that thematerial printed with the dyeing preparations and reactive dyestuffs is steamed for a short time in a continuous working process for developing and fixing the azo dyestuffs by means of high acid concentrations and, if desired, of a counter-current operation method, and that the material is treated thereafter according to a known two-phase-fixation-process for fixing the reactive dyestuffs and finished as usual by washing, soaping and rinsing.
  • Channel steamers having a very narrow channel and, if desired, additional obstacles for the vapor, in which the vapor flowing in is enriched with acid by spraying volatile organic acid by means of a inlet pipe or by introducing these acids dropwise onto a heated plate directly behind the vapor inlet pipe, in which process this acid vapor is guided towards the fabric which passes through the steamer (counten r current principle);
  • Rapid steamer System Hoechst a channel steamer manufactured in a folded form, provided, if desired, with obstacles for the vapor, in which the vapor is enriched with acid, as indicated above, and guided towards the printed good.
  • a device particulary suitable for the process of the present invention is the so-called perforated drum steamer according to Belgian Patent specification No. 741,831, in which the printed fabric is led around a perforated drum, through which the vapor enriched with acid is suctioned into the drum, passing through the fabric.
  • the acid may also be contacted with the acid completely or in part by printing preferably the non-printed side of the good with relatively concentrated acids using a-so-called thousand point roller (finely engraved roller).
  • a relatively uneven application of the acid in this process practically implies no danger for the quality of the print, since the acid is levelled at any rate by the vapor in the steamer.
  • the counter-current method has the further advantage that the acid used is economically better utilized.
  • the acid in the case of the perforated drum steamer the acid is utilized to an optimum by making the vapor circulating and new amounts of acid which is used up by neutralization of the alkalis contained in the print and by absorption by the fabric are continuously added to the circulating vapor.
  • acids there are commonly used volatile organic acids, in general acetic acid or formic acid or mixtures of both acids.
  • a folded channel steamer for example the rapid steamer System Hoechst having a transport speed of 6m
  • a development and fixation speed of 72m/min. which corresponds absolutely to the speed of a usual two phase-steaming device for fixing reactive dyestuffs; thus, both devices may be combined, in which process both types of dyestuff may be developed and fixed continuously.
  • Such an overall device suitable for the continuous fixation of reactive dyestuffs besides and in overprints with stabilized dyeing preparations forming azo dye stuffs may also consist of a rapid steamer and a wet fixing box, the latter having also a transport speed of 6m; thus, in both fixing apparatuses the fixation time amounts to 5 seconds.
  • the investment volume for both plants is much smaller than the volume of one individual acid steamer of traditional structure, which represents also a technical progress.
  • the operation method depends on two criteria: During the short time of acidsteamin g, the reactive dyestuffs must not be submitted to acidic hydrolysis and furthermore, it must be possible to fix them on the fibre by an equally short fixation process.
  • Suitable dyestuffs are preferably reactive dyestuffs reacting to an ether bond with the hydroxyl group of the cellulose and belonging to the type of the ,B-oxyethylsulfone-sulfuric acid ester and -phosphoric acid ester as well as reactive dyestuffs possessing one or several N-methyl'N-B- sulfatoethylsulfonamido groups, B-sulfatoethylaminosulfone groups, chloropropionylamido groups, B-sulfatoethylcarbonamido groups, phenylpropionylamido sulfone groups or 2,2,3,3tetrafluorocyclobutane-l-acryloylamino groups.
  • the sensitivity to the acidic hydrolisis may be reduced, for example by adding sodium acetate to the printing paste
  • dyestuffs reacting to an ether bond-with the cellulose, for instance dyestuffs containing a monoor dichlorotriazine a -trichloropyrimidine group, a dichloroquinoxaline, or dichloro-phthalazine group, or the like.
  • the fixation temperature of the acid-steaming must at least amount to C'in this case.
  • the simultaneous fixing of the disperse dyestuffs during the acid-steaming of the dyeing preparations forming azo dyestuffs may be effected more rapidly, if acid-steaming is not carried out in an aqueous vapor medium but in a solvent vapor, for example ethylene glycol vapor. In this case, steaming times of 5 to 10 seconds at temperatures of from to 200C are sufficient. However,. if solvents containing hydroxyl groups are used in the steaming process, these ones have to be eliminated by an intermediate drying process before wet fixing, since the fixation of the reactive dyestuff is affected adversely as concerns its yield.
  • EXAMPLE 1 15 g of a commercial dyeing preparation from the coupling component of the Colour Index No. 37505 and the stabilized diazonium compound having the Colour Index No. 37 175 were dissolved cold under addition of 20 g of a 32.5 sodium hydroxide solution 50 g of ethanol 200 g of water and 50 g of urea, introduced while stirring into 500 g of a neutral wheatstarch-tragacanth thickening and adjusted with water or thickener to 1 kg of printing paste.
  • a mercerized cotton fabric was first printed with this paste with any design desired by means of a stencil according to the film printing process and subsequently overprinted in overlapping manner with a neutral reactive dyestuff printing paste.
  • This cover-print paste was prepared in the following way: 50 g of the dyestuff of the formula were dissolved by pouring 300 g of hot water on the dyestuff and the whole introduced while stirring into 500 g of a 4 percent by weight of aqueous alginate thickening, to which g'of a sequestering agent on the basis of polyphosphate and 10g of sodium of the mnitrobenzene sulfonic acid were added, before the whole was adjusted to 1 kg of printing paste with water or thickener.
  • the cotton fabric was first developed for 5 seconds in the acid vapor in a rapid steamer System Hoechst for splitting off the diazoamino compound and for subsequent coupling by dropwise introduction of an acid mixture consisting of 5 parts of a 50 percent acetic acid and 1 part of an 85 percent formic acid, into an evaporator which is heated indirectly within the vapor chamber, the passing vapor was enriched very intensely with acid by the vaporizing acid was carrying it along.
  • the fabric was then subsequently passed for 5 seconds at 95-98C through an alkaline aqueous bath containing per liter 100 g of sodium chloride 150 g of sodium carbonate g of potassium carbonate and g of a 32.5 sodium hydroxide solution and then finished as usual by washing, soaping and rins-
  • the rapid development and fixation of the azo dyestuff according to the present process permits to fix the reactive dyestuff subsequently in a homogeneous continuous process (for example .in a wet fixing trough type Goller having a triple transport speed of a total of 6 m per 5 sec.) and to finish the good subsequently on a large-size washing machine so that, at a fixation time of 5 seconds, the whole fixation of the dyestuff and after-treatment may be carried out continuously with a transport speed of 72 m/min.
  • EXAMPLE 2 15 g of a commercially standardized dyeing preparation from a coupling component with the Colour Index No. 37 585 and a stabilized diazonium compound having the Colour index No. 37 were dissolved as in Example 1 and processed to a printable printing paste.
  • a mercerized bleached cotton fabric was printed with this paste with any design desired on a roll printing machine and subsequently provided with' overprints with a neutral reactive dyestuffiprinting paste.
  • This cover-print paste was prepared as in Example 1 using 30 g of the dyestuff of the formula After printing and drying the fabric, the continuous fixation of the dyestuffs and completion of the good was effected as in Example 1 by acid-steaming, subsequently alkaline wet fixation and completion on a large-size washing machine.
  • a mcrcerized cotton poplin was first printed with this paste with any design desired on a film printing machine and subsequently overprinted with a neutral printing paste containing a reactive'dyestuff.
  • This cover-print paste was prepared as in Example 1 using 50 g of the dyestuff of the formula For improving the resistance to acidic hydrolisis, 30 g of sodium acetate were added to this paste.
  • the dyestuff was fixed by acid steaming on a perforated drum steamer of Messrs. Fleissner, Egelsbach, and subsequent wet fixation as in Example 1.
  • EXAMPLE 4 30 g of a commercially standardized dyeing preparation from a coupling component with the Colour Index No. 37 600 and a stabilized diazonium compound having the Colour Index No. 37 120 were dissolved as in Example 1 and processed to a printable printing paste. A mercerized cotton fabric was printed with the print-- ing paste thus-prepared with any design desired according to the film printing process and then dried.
  • the fabric was developed for 5 seconds in the acid vapor in a rapid steamer System Hoechst, in which process by dropwise addition of an acid mixture of 5 parts of a 50 acetic acid and 1 part of an 85 percent formic acid to an evaporator which is heated indirectly within the vapor chamber, the passing vapor was enriched very intensely with acid by the vaporizing acid carrying it along.
  • EXAMPLE 5 40 g of a commercially standardized dyeing preparation from a coupling component with the Colour Index No. 37 610 and a stabilized diazonium compound having the Colour Index No. 37 090 were dissolved as in Example 1 but without addition of urea, and processed to a printable printing paste.
  • the fabric was dried and then nippadded before steaming on the non-printed side with an acid solution of 1 part of a 50 percent acetic acid, 1 part of an percent formic acid and 1 part of water or humidified with a thousand point roller.
  • the subsequent steaming could be effected for 6 seconds with normal vapor, for example in a rapid steamer or preferably on a perforated drum steamer of Messrs. Fleissner, Egelsbach, so that the after-treatment could be directly carried out continuously on a large-size washing machine as in Example 1.
  • EXAMPLE 6 40 g of a commercially standardized dyeing preparation from a coupling component with the Colour Index No. 37 520 and a stabilized diazonium compound having the Colour Index No. 37 090 were dissolved as in Example 1, but without addition of urea, and processed to a printable printing paste.
  • the fabric was steamed as in Example 1 on a rapid steamer System Hoechst with acid vapor for 15 seconds at 180C and finished in a fully continuous way.
  • a bright orange printing sample having a very good fastness to light and an excellent fastness to wet processing was obtained in a good yield and, to a large extent, a tone-in tone-dyeing of both types of fibres.
  • the color yield and the tone-in-tone-dyeing can be improved by a subsequent therrnofixation process for 30-45 seconds at I EXAMPLE 7 g of a commercially standardized dyeing preparation from the coupling component of the Colour Index No. 37590 and the Colour Index No. 37 525 and of a stabilized diazonium compound having the Colour Index No. 37 were dissolved without urea but by addition of 50 g of thiodiglycol as in Example 1, and processed to a finished printing paste with 50 g of sodium chlorate.
  • an acid solution was applied with a thousand point roller onto the non-printed side of the fabric, which was subsequently steamed in counter-current for 15 seconds at 180C on a converscd channel steamer, wherein the channel through which the printed good was passing, was very narrow and contained additional obstacles for the steam; then the fabric was finished continuously on a large-size washing machine.
  • a deep black printing sample was obtained with a good yield and a satisfactory tone-in-tone-dyeing.
  • EXAMPLE 8 50 g of a dyeing preparation from the coupling component having the Colour Index No. 37 550 and the stabilized diazonium compound having the Colour Index No. 37 150 as well as 30 g of a disperse dyestuff of the formula OH NHZ l ll l 1 u NH2 OH were dissolved cold under addition of 20 g of a 32.5 sodium hydroxide solution 50 g of ethanol 200 g of water and 50 g of urea and dispersed, then introduced while stirring into 500 g of a neutral wheat starch-tragacanth-thickening and adjusted to 1 kg of printing paste with water or thickener.
  • any design desired was printed on a mixed fabric of polyester/cotton 67:33 according to the roller printing process.
  • the reverse side of the fabric was humidified by means of a thousand point roller with an acid solution consisting of 1 part of a 50 percent acetic acid, 1 part of an 85 formic acid and 1 part of water and subsequently steamed in a solvent steamer for seconds at l90200C.
  • the fabric introduced into the steamer was pre-heated to C in a pre-posed infra-red chamber. Fixation was carried out in the steamer with ethylene glycol vapor.
  • This method permits to develop and to fix, in one step, the red azo dyestuff from the dyeing preparation on the cotton portion and, at the same time, to fix the blue disperse dyestuff on the polyester portion.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Coloring (AREA)
US00189043A 1970-10-15 1971-10-13 Fixing prints of stabilized azoic and reactive dyes on cellulose and cellulose/polyester Expired - Lifetime US3795479A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19702050631 DE2050631C3 (de) 1970-10-15 Verfahren zum kontinuierlichen Fixieren von stabilisierten, Azofarbstoffe bildenden Färbepräparaten allein, neben oder in Mischung mit Reaktivfarbstoffen auf damit bedrucktes cellulosehaltiges oder ausschließlich aus Cellulosematerial bestehendes Textilgut und Vorrichtung zur Durchführung des Verfahrens

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US3795479A true US3795479A (en) 1974-03-05

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US00189043A Expired - Lifetime US3795479A (en) 1970-10-15 1971-10-13 Fixing prints of stabilized azoic and reactive dyes on cellulose and cellulose/polyester

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US (1) US3795479A (US06277897-20010821-C00009.png)
FR (1) FR2110457B1 (US06277897-20010821-C00009.png)
GB (1) GB1372884A (US06277897-20010821-C00009.png)
NL (1) NL7113828A (US06277897-20010821-C00009.png)
OA (1) OA03815A (US06277897-20010821-C00009.png)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4790043A (en) * 1983-09-27 1988-12-13 Ciba-Geigy Corporation Process and apparatus for applying a chemical to a textile substrate

Families Citing this family (41)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2740679C2 (de) 1977-09-09 1980-01-03 Hoechst Ag, 6000 Frankfurt Verfahren zum Bedrucken von Cellulosefasergeweben
DE2740587C2 (de) 1977-09-09 1979-08-16 Hoechst Ag, 6000 Frankfurt Verfahren zum Bedrucken von textlien Mischgeweben aus Polyester- und Cellulosefasern
DE3841482A1 (de) * 1988-12-09 1990-06-13 Hoechst Ag Einphasen-verfahren zur herstellung von drucken mit reaktivfarbstoffen neben azo-entwicklungsfarbstoffen auf alkalisch vorgrundierten textilien
US5700850A (en) 1993-08-05 1997-12-23 Kimberly-Clark Worldwide Colorant compositions and colorant stabilizers
US5643356A (en) 1993-08-05 1997-07-01 Kimberly-Clark Corporation Ink for ink jet printers
US5773182A (en) 1993-08-05 1998-06-30 Kimberly-Clark Worldwide, Inc. Method of light stabilizing a colorant
US5645964A (en) 1993-08-05 1997-07-08 Kimberly-Clark Corporation Digital information recording media and method of using same
US5865471A (en) 1993-08-05 1999-02-02 Kimberly-Clark Worldwide, Inc. Photo-erasable data processing forms
US6017661A (en) 1994-11-09 2000-01-25 Kimberly-Clark Corporation Temporary marking using photoerasable colorants
US6017471A (en) 1993-08-05 2000-01-25 Kimberly-Clark Worldwide, Inc. Colorants and colorant modifiers
US5733693A (en) 1993-08-05 1998-03-31 Kimberly-Clark Worldwide, Inc. Method for improving the readability of data processing forms
US6211383B1 (en) 1993-08-05 2001-04-03 Kimberly-Clark Worldwide, Inc. Nohr-McDonald elimination reaction
US5681380A (en) 1995-06-05 1997-10-28 Kimberly-Clark Worldwide, Inc. Ink for ink jet printers
US5721287A (en) 1993-08-05 1998-02-24 Kimberly-Clark Worldwide, Inc. Method of mutating a colorant by irradiation
CA2120838A1 (en) 1993-08-05 1995-02-06 Ronald Sinclair Nohr Solid colored composition mutable by ultraviolet radiation
US6033465A (en) 1995-06-28 2000-03-07 Kimberly-Clark Worldwide, Inc. Colorants and colorant modifiers
US5685754A (en) 1994-06-30 1997-11-11 Kimberly-Clark Corporation Method of generating a reactive species and polymer coating applications therefor
US6242057B1 (en) 1994-06-30 2001-06-05 Kimberly-Clark Worldwide, Inc. Photoreactor composition and applications therefor
US5739175A (en) 1995-06-05 1998-04-14 Kimberly-Clark Worldwide, Inc. Photoreactor composition containing an arylketoalkene wavelength-specific sensitizer
US6071979A (en) 1994-06-30 2000-06-06 Kimberly-Clark Worldwide, Inc. Photoreactor composition method of generating a reactive species and applications therefor
US6008268A (en) 1994-10-21 1999-12-28 Kimberly-Clark Worldwide, Inc. Photoreactor composition, method of generating a reactive species, and applications therefor
US5786132A (en) 1995-06-05 1998-07-28 Kimberly-Clark Corporation Pre-dyes, mutable dye compositions, and methods of developing a color
US5798015A (en) 1995-06-05 1998-08-25 Kimberly-Clark Worldwide, Inc. Method of laminating a structure with adhesive containing a photoreactor composition
ATE195815T1 (de) 1995-06-05 2000-09-15 Kimberly Clark Co Farbstoffvorläufer und diese enthaltende zusammensetzungen
US5747550A (en) 1995-06-05 1998-05-05 Kimberly-Clark Worldwide, Inc. Method of generating a reactive species and polymerizing an unsaturated polymerizable material
US5811199A (en) 1995-06-05 1998-09-22 Kimberly-Clark Worldwide, Inc. Adhesive compositions containing a photoreactor composition
US5855655A (en) 1996-03-29 1999-01-05 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US6099628A (en) 1996-03-29 2000-08-08 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
JPH10513502A (ja) 1995-11-28 1998-12-22 キンバリー クラーク ワールドワイド インコーポレイテッド 改良された着色剤安定剤
US5782963A (en) 1996-03-29 1998-07-21 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5891229A (en) 1996-03-29 1999-04-06 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US6524379B2 (en) 1997-08-15 2003-02-25 Kimberly-Clark Worldwide, Inc. Colorants, colorant stabilizers, ink compositions, and improved methods of making the same
CA2298468A1 (en) 1998-06-03 1999-12-09 John Gavin Macdonald Novel photoinitiators and applications therefor
CA2298615C (en) 1998-06-03 2009-03-31 Kimberly-Clark Worldwide, Inc. Neonanoplasts produced by microemulsion technology and inks for ink jet printing
WO2000004104A1 (en) 1998-07-20 2000-01-27 Kimberly-Clark Worldwide, Inc. Improved ink jet ink compositions
JP2003533548A (ja) 1998-09-28 2003-11-11 キンバリー クラーク ワールドワイド インコーポレイテッド 光重合開始剤であるキノイド基を含むキレート
ES2195869T3 (es) 1999-01-19 2003-12-16 Kimberly Clark Co Nuevos colorantes, estabilizantes de colorantes, compuestos de tinta y metodos mejorados para su fabricacion.
US6331056B1 (en) 1999-02-25 2001-12-18 Kimberly-Clark Worldwide, Inc. Printing apparatus and applications therefor
US6294698B1 (en) 1999-04-16 2001-09-25 Kimberly-Clark Worldwide, Inc. Photoinitiators and applications therefor
US6368395B1 (en) 1999-05-24 2002-04-09 Kimberly-Clark Worldwide, Inc. Subphthalocyanine colorants, ink compositions, and method of making the same
KR100772772B1 (ko) 2000-06-19 2007-11-01 킴벌리-클라크 월드와이드, 인크. 신규한 광개시제 및 그의 용도

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3567356A (en) * 1966-05-11 1971-03-02 Hoechst Ag Reactive and disperse dyes fixed on cellulose blended fabrics travelling on drum radially passing hot gas

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3567356A (en) * 1966-05-11 1971-03-02 Hoechst Ag Reactive and disperse dyes fixed on cellulose blended fabrics travelling on drum radially passing hot gas

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Fortess et al., ADR, 5/27/63, p. 16 25. *
Wygand, ADR, 12/7/64, p. 106 109. *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4790043A (en) * 1983-09-27 1988-12-13 Ciba-Geigy Corporation Process and apparatus for applying a chemical to a textile substrate

Also Published As

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DE2050631B2 (de) 1977-03-03
NL7113828A (US06277897-20010821-C00009.png) 1972-04-18
FR2110457A1 (US06277897-20010821-C00009.png) 1972-06-02
OA03815A (fr) 1971-12-24
GB1372884A (en) 1974-11-06
DE2050631A1 (de) 1972-06-08
FR2110457B1 (US06277897-20010821-C00009.png) 1977-01-14

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