WO2012120543A1 - Procédé en une seule étape pour la synthèse du colorant yellow dye 11 de ton uniforme - Google Patents

Procédé en une seule étape pour la synthèse du colorant yellow dye 11 de ton uniforme Download PDF

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Publication number
WO2012120543A1
WO2012120543A1 PCT/IN2012/000162 IN2012000162W WO2012120543A1 WO 2012120543 A1 WO2012120543 A1 WO 2012120543A1 IN 2012000162 W IN2012000162 W IN 2012000162W WO 2012120543 A1 WO2012120543 A1 WO 2012120543A1
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WO
WIPO (PCT)
Prior art keywords
dye
reaction
pntosa
synthesis
yellow
Prior art date
Application number
PCT/IN2012/000162
Other languages
English (en)
Inventor
Amol Arvind Kulkarni
Ramesh Anna Joshi
Rohini Ramesh Joshi
Original Assignee
Council Of Scientific & Industrial Research
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Council Of Scientific & Industrial Research filed Critical Council Of Scientific & Industrial Research
Priority to DE112012001131.7T priority Critical patent/DE112012001131T5/de
Publication of WO2012120543A1 publication Critical patent/WO2012120543A1/fr

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Classifications

    • 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
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0072—Preparations with anionic dyes or reactive dyes
    • C09B67/0073—Preparations of acid or reactive dyes in liquid form
    • 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
    • C09B27/00—Preparations in which the azo group is formed in any way other than by diazotising and coupling, e.g. oxidation
    • 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
    • C09B56/00—Azo dyes containing other chromophoric systems
    • C09B56/04—Stilbene-azo dyes
    • C09B56/06—Bis- or polystilbene azo dyes
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D21H21/28—Colorants ; Pigments or opacifying agents

Definitions

  • This invention discloses a continuous process for the manufacture of yellow-11 dye.
  • the invention discloses a process for the manufacture of yellow dye Y 11 with colour variations.
  • Yellow 11 is a dye used widely in the dye industry for varied applications in printing, textiles and others.
  • the synthesis of the dye using para-nitro-toluene sulphonic acid (PNTOSA) and sodium hydroxide is well known in the art. Refer US patent 4310331, BIOS Report No. 1548, page 173, 1946.
  • US Patent No.4310331 discloses the process for the preparation of the dyestuff Direct Yellow 11, in the form of stable concentrated solution which comprises, reacting caustic soda in aqueous solution with a solution containing PNTSA ( para-nitro toluene sulfonic acid) , one or more alkanolamines and one or more alcohols containing an etheroxide at a temp of 40°C to 90°C, then neutralizing caustic soda with sulfuric acid and separating the sodium sulphate by filtration, which yields crude free acid dyestuff.
  • PNTSA para-nitro toluene sulfonic acid
  • US Patent No. 4617380 discloses a process for the preparation of- a liquid dyestuff of CI Direct Yellow 11 (Paper Yellow 11) in stable form, from the tetrasodium complex of this stilbeneazo(xy) base-catalyzed condensation of 4-nitrotoluene-2-sulfonic acid using as the starting material. Further the free acid complex of said dyestuff treated with an alkanolamine/water mixture to obtain a stable liquid dyestuff Direct Yellow 11 of proper tinctorial strength. The final complex, after removal of the excess water, is adjusted to an absorbence of 24 at lambda.max 417 nm.
  • US Patent No.4617381 discloses a process is disclosed for the preparation of concentrated stable liquid dye solutions of CI Direct Yellow 11 starting with the product of the basic condensation of para-nitrotoluene-ortho-sulfonic acid in the form of its tetrasodium reaction mass; which is further treated with a lower alkanol/water medium; to obtain Direct Yellow 11- alkanolamine complex.
  • US Patent No. 5041539 discloses a batch process for preparing and concentrating storage- stable aqueous solutions of yellow azo- or azoxystilbene dyes which comprises: (a) self- condensing 4-nitrotoluene-2-sulfonic acid in an alkaline solution of an alkali metal hydroxide (NaOH, KOH); the condensation is carried out. in a pH range from about 11 to 13 and in the temperature range from 60 °C to 80°C. (b) acidifying the reaction mixture of step (a) with LLS 228
  • Typical batch process practiced in the industry is a two step process where PNTOSA is mixed with some part of NaOH (caustic lye) which leads to a temperature rise from 22.4 - 46.5 °C depending upon the quantity. Larger quantities yield much higher temperature rise and hence mixing of reactants in one step is avoided.
  • a lot of ice is added to the reactor keep the temperature in control. After stabilizing the temperature, reaction mixture is taken to 58-62 °C and then rest of the NaOH is added. This time the temperature rise is not significant and typically it goes to as much as 68 - 70 °C. Then it is maintained in this range until reaction is complete. A brown -red dye is produced, which is applied on paper after dilution.
  • the main object of the present invention is to provide a process for the synthesis of Y-ll dye resulting in consistent tone of the dye.
  • Another object of the invention is to propose optionally batch as well as continuous process for the synthesis of Y-ll dye resulting in consistent tone of the dye.
  • Yet another object of the invention is to control various process parameters precisely such that the resultant dye is consistently of uniform tone.
  • One more object of the invention is to present an online analytical technique that affords to exactly indicate the end point of the reaction which enables production of dye with uniform tone consistently.
  • the present invention provides a single step process for synthesis of Yellow dye 11 of consistent colour tone wherein the process steps comprising:
  • step (c) terminating the reaction of step (b) by addition of cold water on appearance of peak at 410 nm and
  • alkali is selected from the group consisting of hydroxides of sodium, potassium, lithium, alone or in combinations thereof.
  • ration of PNTOSA:alkali is in LLS 228 the range of 1:1 to 1:1.5
  • reaction time 85-95 minutes
  • the process of the invention resulting in consistent colour tone using online UV monitoring system comprises reacting aqueous solution of para nitro toluene sulphonic acid (PNTOSA) with aqueous solution of an alkali at reaction temperature of 65-90 °C and determining the termination time of the reaction by online uv monitoring.
  • PNTOSA para nitro toluene sulphonic acid
  • the alkali of the invention are hydroxides of sodium, potassium, lithium, alone or in
  • the acids are mineral acids selected from HCI, H 2 SO 4 and such like.
  • the online uv monitoring of the reaction to determine the termination of the reaction comprises the steps of : 50 ⁇ of reaction mixture is dissolved in 4 ml water. From this 4ml of sample only 20 ⁇ of sample is taken in UV quartz cuvette and dissolved in 1 ml of water for LLS 228
  • UV-Vis analysis UV absorption spectrum of the sample is recorded in the range of 200-800 nm.
  • the reactant has an absorbance at 278 nm while the product has an absorbance at 410 nm.
  • Consistent colour tone of Yellow dye 11 is determined by the online monitoring system of the invention. In the uv spectrum, there should be no peak at 278 nm, rather there should be a valley at 278 nm indicating the complete consumption of the reactant. A peak at 410 nm indicates formation of Yellow 11 dye. This is determines colour consistency, since the presence of the initial reactant affects the tone of the product and will therefore not exhibit a peak at 410 nm.
  • the process of the invention results in 100 % conversion of PNTOSA to yellow 11 dye.
  • the process is carried out with equivalent quantities of alkali and PNTOSA.
  • the process is carried out with a ration of 1:1.5 for PNTOSA:alkali
  • the process is optionally batch or continuous process.
  • the continuous flow synthesis employs SS tubes of length ranging from 1/16" to 1 inch in diameter, microreactors and tubular reactors.
  • the reaction time in continuous flow synthesis ranges from 60-90 minutes, though optionally reaction times are increased to get varying colour tones. Tone of colour of dye Y 11 is further dependent on temperature of process of invention.
  • the reaction times are greater than that of continuous flow synthesis, ranging from 60-120 minutes.
  • One of the following two approaches were used for enhancing mixing in the tube or reducing axial dispersion to get better product quality.
  • the mixing along the length of the reactor is increased by placing static mixers at several places inside the tube. Having static mixers helped achieve better mixing even through the viscosity of the fluids increase towards the end of the reaction tube.
  • the axial dispersion was reduced by using a segmented flow approach by passing inert gas through the reactor.
  • the process is carried out conventionally, optionally in microreactor and such like.
  • the microreactor of process of the invention varies in diameter ranging from 1/16" to 1".
  • the material of construction of the microreactor is SS316. LLS 228
  • the A max of the Y 11 dye is between 416-419 nm with standard deviation of 1.5%.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Le colorant Yellow Dye 11 est un colorant utile présentant plusieurs applications industrielles. La bibliographie existante sur la synthèse de ce colorant décrit l'obtention d'un ton non uniforme. Ce problème de l'art antérieur est résolu par la présente invention, qui concerne un procédé de synthèse en une seule étape de condensation par lots ou en continu du colorant Yellow Dye 11 intégrant un système de contrôle par ultraviolets pour garantir l'uniformité du ton.
PCT/IN2012/000162 2011-03-09 2012-03-09 Procédé en une seule étape pour la synthèse du colorant yellow dye 11 de ton uniforme WO2012120543A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE112012001131.7T DE112012001131T5 (de) 2011-03-09 2012-03-09 Einstufiges Verfahren zur Synthese von "Yellow-11"-Farbstoff mit gleichmäßigem Farbton

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN650DE2011 2011-03-09
IN0650/DEL/2011 2011-03-09

Publications (1)

Publication Number Publication Date
WO2012120543A1 true WO2012120543A1 (fr) 2012-09-13

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Application Number Title Priority Date Filing Date
PCT/IN2012/000162 WO2012120543A1 (fr) 2011-03-09 2012-03-09 Procédé en une seule étape pour la synthèse du colorant yellow dye 11 de ton uniforme

Country Status (2)

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DE (1) DE112012001131T5 (fr)
WO (1) WO2012120543A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3557079A (en) * 1967-02-01 1971-01-19 Allied Chem Production of stilbene azo dyes
DE2601470B1 (de) * 1976-01-16 1976-09-16 Bayer Ag Verfahren zur herstellung von kondensationsfarbstoffen
US4310331A (en) 1980-03-21 1982-01-12 Produits Chimiques Ugine Kuhlmann Process for the preparation of the dyestuff direct yellow 11 in the form of concentrated stable solutions, the solutions obtained and their applications
US4617381A (en) 1984-09-11 1986-10-14 Ciba-Geigy Corporation Process for the preparation of concentrated stable liquid dye solutions of CI Direct Yellow 11 utilizing an alkanol/water solvent in a desalting procedure
US4617380A (en) 1984-09-11 1986-10-14 Ciba-Geigy Corporation Process for the preparation of concentrated stable liquid dye solutions of CI Direct Yellow 11 utilizing an extended surface silica filter aid during a desalting procedure
US5041539A (en) 1984-11-12 1991-08-20 Ciba-Geigy Corporation Preparation of aqueous concentrates of yellow azo and azoxystilbene dyes utilizing alkanolamine salts

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3557079A (en) * 1967-02-01 1971-01-19 Allied Chem Production of stilbene azo dyes
DE2601470B1 (de) * 1976-01-16 1976-09-16 Bayer Ag Verfahren zur herstellung von kondensationsfarbstoffen
US4310331A (en) 1980-03-21 1982-01-12 Produits Chimiques Ugine Kuhlmann Process for the preparation of the dyestuff direct yellow 11 in the form of concentrated stable solutions, the solutions obtained and their applications
US4617381A (en) 1984-09-11 1986-10-14 Ciba-Geigy Corporation Process for the preparation of concentrated stable liquid dye solutions of CI Direct Yellow 11 utilizing an alkanol/water solvent in a desalting procedure
US4617380A (en) 1984-09-11 1986-10-14 Ciba-Geigy Corporation Process for the preparation of concentrated stable liquid dye solutions of CI Direct Yellow 11 utilizing an extended surface silica filter aid during a desalting procedure
US5041539A (en) 1984-11-12 1991-08-20 Ciba-Geigy Corporation Preparation of aqueous concentrates of yellow azo and azoxystilbene dyes utilizing alkanolamine salts

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
ARTHUR GEORGE GREEN; PERCY FIELD CROSLAND: "CLXII.-The colouring matters of the Stilbene group. Part III", JOURNAL. CHEM. SOC., TRANS., vol. 89, 1906, pages 1602 - 1614, XP009160143, DOI: doi:10.1039/CT9068901602
BIOS REPORT, no. 1548, 1946, pages 173
K.VENKATARAMAN: "The Chemistry of Synthetic Dyes", vol. I, 1952, ACADEMIC PRESS INC., New York, pages: 628 - 631, XP002677699 *

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