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

Definitions

• the dried product creates dusting problems during grinding and in subsequent processing steps, such as measuring, pouring' and packaging and use in the dye house.
• the fine 4 dust. particles so created are a work hazard in the form of possible skin irritations and other health hazards among the workers.
• improved stabilized diazonium compounds may be obtained by first reacting the diazotization product with a surface active agent, thereby effecting a partial stabilization of the diazonium compound with the, surface active agent, and then effecting the remainder of the stabilization with one of the usual Fast Color Salt stabilizers mentioned above.
• the surface active agents which have been found effective are those of the anionic reactive groupwherein the surface active agent contains an aliphatic hydrophobic group and an aliphatically linked hydrophilic group. Included in this group are surface active alkyl carboxylates, sulfonates, alcohol sulfates and phosphates. More specifically, there are included the following classes of surface active agents:
• Alkali metal soaps such as sodium oleate
• CH3(CH2)'1CHZCH(CH2)1COONa and sodium stearate CH3 (CH2) uCOONa 2.
• sulfates of higher fatty acids such as sulfonated castor oil (triglyceride of ricinoleic acid) OSOSNfl CHKCHDsHCHzCH:CH(CHz)1C 0 O CH;
• Sulfonated higher fatty alcohols such as" the cetyl sulfonic acid and the sodium salt of f dodecyl s-ulfonic acid of USP 1,966,187.
• Alkylsulfonamido acetates such a e product known as Emulphor S'I'H i 13.
• Alkylphenoxyalkyl sulfates such as the sodium sulfuric ester of isooetyl phenyl monoglycolether ooiHio'soiNa The sodium sulfuric ester of dodecyl phenyl monoglycolether CizHz O CgHfOSOsNB butylphenoxy ethanol l4.
• Amino soaps of fatty acids such as the stearic acid soap of 2-amino-l-butanol
• the diazonium compounds stabilizedby the surface activeagents and the salts or acids generally ve nployedas stabilizing agents in Fast Color Salts 'F'SuchasmetaIlic chlorides, particularly the mercury, iron, zinc, cadmium, tin, antimony, platinum, gold, copper and arsenic chlorides, naphthalenefiulfonicacids such as naphtha1ene1.5
• I disulfonic acid, and fiuoroboric acid are prepared by introducing a solutionsof'the surface active agent into the diazotization solution.
• the combihed diazo solution and surface active agent solution is then mixed withasolution'eontaining the additional stabilizing agent.
• the exact order of mixing the reactants is-not' material, although it is preferableto initially mix the diazonium compoundand the' surface active agent.
• the diazo-,andfsurface active agent can be combined first-and the combined solutions added to a solution of the Fast Color Salt stabilizer (such as 2171012)?
• the stabilization of the diazonium salts by means of the surface active agents ,of this-invention thus results in an appreciable reduction of the water content of the filtered diazo cake, as a direct result of the change in crystal pattern or v formation of larger crystals or crystal aggregates.
• the comparative ratio being in the range of 25 to 50% for the conventionally stabilized diazonium salts to 5 to for the diazonium salts stabilized in accordance with this invention.
• the surface active agent Preferably about 5 to 20% of the surface active agent based on the. amount of the diazo compound is employed. Afterfiltering and dry. mixing'of the filter cake it may be noted that. the dusting characteristic I of the drypowdered.
• the filter cake contains only a fraction of the-water which "is present in'the same di-' azonium salt stabilized by the usual complex salt formation with such compounds as ZnClzand hence requires smaller amounts of the dehydrating agents. Also-the necessity for rigorous'oven drying is eliminated in those cases where the Fast Color'Salts stabilized with the usual stabiliz ers' retain a large amount of-waten In' such cases it is normally necessary not only to hydraulically press them, but also to pre-dry them in ovens heated to approximately 40 C.
• taining 6.0 .gr..sodium'oleate per cc. of water is run into the diazo solution.
• the resulting solution is run intov a solution containing 57.6 gr. 1.5-naphthalene disulfonic acid in 100 cc. of water.
• the precipitate is filtered, sucked dry, and dry mixed and standardized with sodium sulfate, aluminum sulfate and calcined magnesium sulfate.
• Example 2 follov v ing mixture is slurried for 2 to 3 hours: v 76 cc. water I 50.6 cc. hydrochloric acid (21 B.) 33.6 g-r.- i-nitro-oanisidine The mixture is cooled to 10 C. and 13.8 gr.
• the product thus obtained has a coarser crystalline structure than the product obtained in a similar manner, but without the addition of the sulfonated castor oil.' Because of this coarser crystalline structure the filter cake has a higher degree of initial dryness, thus requiring the addi- 8 tion of smalleramounts of the drying compounds used in dry mixing and lessening the tendency to dust of the dry particles.
• I v s r Erample 3 32.4 gr.-2.5-dichloroaniline are slurried with 46 cc. of water and then heated to 60 C. While applying fast agitation 78 cc. hydrochloric acid (21 B.) are added over a ten minute period.
• sulfonicgacid are then added, followed by 7 gr. ZnQh'. disso v d in a' small amount of water.
• the product obtained in accordancewith this example has properties similar to'thecon ipositions of Examples'l and 2 as comparedwitlithe product f; obtained in a similar manner to that of thisg'f example by omitting the sodium salt of ,dodejcyl'i sulfonic acid.
• Ezrample 4 l sulting stabilized diazonium salt is salted'out with NaCl equivalent to 10% of the volume, filtered, sucked-dry, dry mixed and standardized with sodium sulfate, aluminum sulfate and calcined I
• the thus obtained product has properties similar to those of the productobmagnesium sulfate.
• Example 5 i 33.6 gr. 5-nitro-o-anisidine are slurried with cc. of water. To this are added 65 cc. hy-
• the filter 'cake has a higher degree of initial dryness, thus .ree 1' 'quiring asmaller amount of the drying compound used in dry mixing and lessening the tendency toiff dust of the particles.
• V Escample'd S nitrO-o-anisidine is diazotized in the same. manner as in Example 5. After filteringwtheq charcoal treated diazo solution, petroleum oilsul-e. fonate such as Twitchell Oil 3X is added in the;
• the precipitate is filtered, sucked dry, stand-1 ardized and dry mixed with sodium sulfate, alu-f 5 minum sulfate and calcinedmagnesium sulfate.
• the product thus obtained has acoarser crystal-, line structure than the product. obtained in a.- v
• the mixture is cooled chloric acid"in"80 cc.” of water.
• the mixture is cooled to C. and 13.8 gr. sodium nitrite in a" 33 solution'are added while maintaining the temperature belowj C.
• the resulting di'azo The staride equivalent'to 10% ofthe volume; then fil-' tered, sucked dry,- standardized. and dry.
• Example 8 31 .5 r; of 5 -chloro -o'-'anisidin'e are added to l ccfiof "water and the mixture heated togetheri't'o 85" CI 27jcc. of hydrochloricacid (21 Be.) are then 'added. The resulting solution is cooled to chloric' acid are added. The solution is" again addedas ja1333% solution. The resultingsolution is purified'jby the addition of charcoal and filtered. To the filtered'solution there is added ⁇ a solution'of 5 er.
• Example 9 2813 of:ii chloro-o toluidine are added.- 115 cc. ofwater "and the solution. heated tot85t" C. 2'z'cct of 21 B. HCl. are thenradded andthe solution coole'd'to- 5 C. while adding:antaddis. tional'i27 cc.” of 21.B; HCl.
• diazogcompoun'd is purifiedbythe addia tion' of charcoaland filtered.
• diaizo solution thereareadded 4 gn ofthev sodiumi': salt' 'ofoleyl sarcosine in 20 cc; of water;- A con-'- eentrated aqueous solution of 7 gr, Of 'ZIiCIQ'ar'e those obtained .as-the product ofExample thenfradded. and the stabilized: diazoncompoundt.
• the productcobei tained has a coarser crystallineistructurea than;
• cined magnesium sulfate The crystalline product .thus obtained has characteristics similar to Emmpze 12 33.6 gr. Z-nitro-p-anisidine are slurriedrin r46 cc. of water. 53 color 21 BVHCI are addedto: 1 the slurry and theresulting solutionis .cooledto 5 C.,- after which 13.8 gr. sodium"nitritev aref addedas 9. 33% solution. Thisdiazotizationrsolution is then salted to saturation; clarified byr treatment with charcoal and filtered.
• the product thusuobtained has a coarser crystalline structure than that obtained ina similar manner but without the addiation of: thesulfated'mixed fatty acid monoglyceride.,,:..,
• the stabilized diazo is salted out with an amount of NaCl equivalent to 10% .of the volume, filtered, sucked dry, and dry mixed and standardized by the addition of sodium sulfate, aluminum sulfate and calcined magnesium sulfate.
• the crystalline product thus obtained is similar in characteristics to the product of Example 10.
• Example 16 The following mixture is slurried for 1 hr.:
• a stable, dry, non-dusting clia position comprising an aromatic diazonium salt in complex combination with a mixture of an anionic surface-active agent containing at least one long chain alkyl group and having its hydrovphilic group aliphatically. linked, and cadmium chloride, said complex diazonium salt combination having a crystalline form which retains less mother liquor in a filter cake obtained by filtration of an aqueous suspension thereof than a filter cake of the corresponding aromatic diazonium salt combined as a complex solely with cadmium chloride.
• a stable, dry, non-dusting diazonium composition comprising an aromatic diazonium salt in complex combination with a mixture of an anionic surface-active agent containing at least one long chain alkyl group and having its hydrophilic group aliphatically linked, and 1,5-naphthalene disulfonic acid, said complex diazonium salt combination having a crystalline form which retains less mother liquor in a filter cake obtained position" comprising an -aromatic diazonium' saltv diazonium salt in solid form which involves precipitationxof: anxaromatic: :diazonium risalt.
• stai'bilizerjithe improvement which comprises adding to"the'"aqueous'solution of said diazonium salt, prior to said precipitation,"an"'anionicisur-' face-active .agentcontaining at 1e'ast"one long fc'liain” alkyk'group and having its hydrophilic i j jg'roupiaiiphatica'lly linkedfi the surface active "agenti'being added in anramount 'equal' to at ?*leas't %ofthe' amount of'the"idia”zonium'salt,
• Idiazonium:comzposition comprising: an raromaticirdiazoniumaisalt in complex combination with a mixturasof a Fast Color Saltvstabilizerz and an anionic surl5 face-active .agent.containing .at least one long i chaimalkyl"grouptandi.

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• Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Organic Chemistry (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Heat Sensitive Colour Forming Recording (AREA)
• Cosmetics (AREA)

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Citations (5)

• 1948
  • 1948-10-22 US US56047A patent/US2612494A/en not_active Expired - Lifetime
• 1949
  • 1949-08-02 FR FR991566D patent/FR991566A/fr not_active Expired
  • 1949-09-05 CH CH280836D patent/CH280836A/fr unknown
  • 1949-10-13 DE DEG79A patent/DE855117C/de not_active Expired
  • 1949-10-13 GB GB26330/49A patent/GB661533A/en not_active Expired

Patent Citations (5)

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