NO811997L - PROCEDURE FOR PREPARING CONCENTRATED SOLUTIONS OF AZO COLORS. - Google Patents
PROCEDURE FOR PREPARING CONCENTRATED SOLUTIONS OF AZO COLORS.Info
- Publication number
- NO811997L NO811997L NO811997A NO811997A NO811997L NO 811997 L NO811997 L NO 811997L NO 811997 A NO811997 A NO 811997A NO 811997 A NO811997 A NO 811997A NO 811997 L NO811997 L NO 811997L
- Authority
- NO
- Norway
- Prior art keywords
- parts
- mixture
- acid
- dye
- solutions
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- 239000000987 azo dye Substances 0.000 title claims description 6
- 239000000975 dye Substances 0.000 claims description 31
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- 238000001914 filtration Methods 0.000 claims description 11
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical group C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 claims description 10
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical group NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 claims description 10
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 10
- 235000011152 sodium sulphate Nutrition 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 9
- 235000010288 sodium nitrite Nutrition 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 7
- 230000008878 coupling Effects 0.000 claims description 7
- 238000010168 coupling process Methods 0.000 claims description 7
- 238000005859 coupling reaction Methods 0.000 claims description 7
- 229950000244 sulfanilic acid Drugs 0.000 claims description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 6
- CQPFMGBJSMSXLP-ZAGWXBKKSA-M Acid orange 7 Chemical group OC1=C(C2=CC=CC=C2C=C1)/N=N/C1=CC=C(C=C1)S(=O)(=O)[O-].[Na+] CQPFMGBJSMSXLP-ZAGWXBKKSA-M 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- WPWNIQBSYQVEKJ-UHFFFAOYSA-M chembl2028451 Chemical group [Na+].CC1=CC(S([O-])(=O)=O)=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 WPWNIQBSYQVEKJ-UHFFFAOYSA-M 0.000 claims description 6
- KRLKXOLFFQWKPZ-UHFFFAOYSA-N 4-(bromomethyl)pyridine Chemical group BrCC1=CC=NC=C1 KRLKXOLFFQWKPZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000006193 diazotization reaction Methods 0.000 claims description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000007822 coupling agent Substances 0.000 claims 1
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 claims 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 6
- 238000010494 dissociation reaction Methods 0.000 description 5
- 230000005593 dissociations Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000428 dust Substances 0.000 description 3
- -1 alkyl nitriles Chemical class 0.000 description 2
- 229950011260 betanaphthol Drugs 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- LZDSILRDTDCIQT-UHFFFAOYSA-N dinitrogen trioxide Chemical compound [O-][N+](=O)N=O LZDSILRDTDCIQT-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- 206010013457 Dissociation Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 208000018459 dissociative disease Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical compound O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- HSXUHWZMNJHFRV-QIKYXUGXSA-L orange G Chemical compound [Na+].[Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1\N=N\C1=CC=CC=C1 HSXUHWZMNJHFRV-QIKYXUGXSA-L 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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
- C09B41/00—Special methods of performing the coupling reaction
-
- 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
- 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
- C09B67/0083—Solutions of dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
- C09B69/04—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds
- C09B69/045—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds of anionic azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
- Paper (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Foreliggende oppfinnelse angår en fremgangsmåte for fremstilling av azofarvestoffer direkte i form av stabile konsentrerte oppløsninger samt de således oppnådde oppløsnin-ger. The present invention relates to a method for the production of azo dyes directly in the form of stable concentrated solutions as well as the solutions thus obtained.
De anioniske farvestoffer som er oppløselige i vann selges generelt og benyttes også i form av pulvere:omfattende en større eller mindre andel av uorganiske salter. The anionic dyes which are soluble in water are generally sold and also used in the form of powders: comprising a greater or lesser proportion of inorganic salts.
Visse fordeler, men også tallrike mangler er forbundet med denne form. Hovedfordelen ligger i den store stabilitet ved lagring av disse produkter; spesielt observeres ingen modi-fikasjoner under lagringen, selve temperaturer under 0°C, noe som muliggjør at de kan lagres til alle årstider i oppvarmede rom. Certain advantages, but also numerous shortcomings are associated with this form. The main advantage lies in the great stability when storing these products; in particular, no modifications are observed during storage, temperatures themselves below 0°C, which enables them to be stored for all seasons in heated rooms.
På den anne side er det kjent at pulverformige farvestoffer har en markert tendens til å frigjøre støv når de be-handles. Forsøk har vært gjort på å bekjempe denne mangel ved forskjellige fremgangsmåter. Ved tilsetning av oljer eller hygroskope væsker blir frigjøringen av støv effektivt redusert, på den annen side blir oppløsningen av farvestoffene vanskeliggjort. Det har også vært gjort forsøk på å gi farvestoffene en form som har hatt en mindre tendens til å avgi støv ved å omdanne dem til granuler. Fordi farvestoffene deretter finnes i meget kompakt form var det meget vanskelig å oppløse dem, spesielt når det var snakk om farvestoffer som var mindre oppløselige i vann. Dette er tilfelle for de farvestoffer som utgjør gjenstanden for foreliggende oppfinnelse, når de er tilstede i form av pulver. On the other hand, it is known that powdered dyes have a marked tendency to release dust when they are processed. Attempts have been made to combat this deficiency by various methods. By adding oils or hygroscopic liquids, the release of dust is effectively reduced, on the other hand, the dissolution of the dyes is made more difficult. Attempts have also been made to give the dyes a form which has had a lower tendency to emit dust by converting them into granules. Because the dyes are then found in very compact form, it was very difficult to dissolve them, especially when it came to dyes that were less soluble in water. This is the case for the dyes which form the subject of the present invention, when they are present in the form of powder.
Foreliggende oppfinnelse angår en fremgangsmåte for fremstilling av stabile og meget konsentrerte oppløsninger av azofarvestoffer oppløselige i vann og mere spesielt de som er beskrevet i farveindeksen linder betegnelsen surt oransje 7 The present invention relates to a method for the production of stable and highly concentrated solutions of azo dyes soluble in water, and more particularly those described in the color index, the designation acid orange 7
og surt oransje 8. Oppløsningene som oppnås ved fremgangsmåten utgjør også en gjenstand for oppfinnelsen og disse inneholder mellom 40 og 65% farvestoff med henblikk på oppløsningens totale vekt. and acid orange 8. The solutions obtained by the method also form an object of the invention and these contain between 40 and 65% dye with regard to the total weight of the solution.
Oppløsninger av azofarvestoffer er allerede foreslått. De amerikanske patenter nr. 3.898.033, 4.019.858, 3.551.088, 3.681.320, 3/986.827, 4.082.742. 4.043.752 og 4 . 063 . 880 .. samt de franske patenter nr. 2.197.951, 2.216.324 og 2.109.806■be-skriver oppløsninger hvis konsentrasjon ikke overskrider 25% farvestoff. Andre patenter slik som de tyske patenter nr. 2.629.673 og 2.629.674 såvel som det britiske patent nr. 1.355.437 beskriver oppløsninger hvis konsentrasjon.kan gå opp i 40%, men deres fremgangsmåte går over tørre,farvestoffer; , Solutions of azo dyes have already been proposed. U.S. Patent Nos. 3,898,033, 4,019,858, 3,551,088, 3,681,320, 3/986,827, 4,082,742. 4,043,752 and 4 . 063 . 880 .. as well as the French patents Nos. 2,197,951, 2,216,324 and 2,109,806■describe solutions whose concentration does not exceed 25% dye. Other patents such as the German Patent Nos. 2,629,673 and 2,629,674 as well as the British Patent No. 1,355,437 describe solutions whose concentration can go up to 40%, but their process involves dry dyes; ,
i praksis er det egnet å fremstille farvestoffer i vann, se-parere det ved filtrering, tørke det,, oppløse det i oppløs- ; . ningsmidlet eller oppløsningsmidlene som er nødvendige og, . fjerne den uoppløselige del ved filtrering. Denne prosess er lang og nødvendiggjør tallrike trinn, den er således komplisert. Andre patenter beskriver analogé fremgangsmåter for fremstil-^ling. Dette er tilfelle i de franske patenter nr..2.193.065 og 2.316.296, de tyske patenter nr. 2 .061. 760, og , 2 .341. 293. ,.. eller belgisk patent nr. 828.876. I enkelte, tilfeller til-siktes bruk av en fuktig pasta av farvestoffet, noe som kunne utgjøre en hvis fordel hvis det ikke var nødvendig å fremstille den frie syre av farvestoffet slik som i belgisk patent nr. 631.379. Således er det ofte vanskelig å oppnå den frie syre av et sulfonert farvestoff og det oppstår ofte vanskeligheter ved filtrering...-, in practice it is suitable to prepare dyes in water, separate it by filtration, dry it, dissolve it in a solvent; . ning agent or solvents that are necessary and, . remove the insoluble part by filtration. This process is long and requires numerous steps, it is thus complicated. Other patents describe analogous methods of manufacture. This is the case in the French patents no. 2,193,065 and 2,316,296, the German patent no. 2,061. 760, and , 2 .341. 293. ,.. or Belgian Patent No. 828,876. In some cases, the use of a moist paste of the dye is intended, which could constitute an advantage if it were not necessary to prepare the free acid of the dye as in Belgian patent no. 631,379. Thus, it is often difficult to obtain the free acid of a sulphonated dye and difficulties often arise during filtration...-,
Fransk patent nr. 2.110.324 antyder oppløsninger som omfatter opptil 75 vekt-% av farvestoffet. Ikke desto mindre, og dette er også et resultat av læren fra fransk patent nr. 2.174.161, kan virkelig konsentrerte oppløsninger kun oppnås, hvis dissosiasjonene gjennomføres ved hjelp av alkylnltriler, nitrøst anhydrid eller blandinger av nitrogenoksyd og luft. Således er det åpenbart fra eksemplene 10, 11, 15 til.17 i French Patent No. 2,110,324 suggests solutions comprising up to 75% by weight of the dye. Nevertheless, and this is also a result of the teachings of French Patent No. 2,174,161, really concentrated solutions can only be obtained if the dissociations are carried out by means of alkyl nitriles, nitrous anhydride or mixtures of nitrogen oxide and air. Thus it is obvious from examples 10, 11, 15 to.17 i
det franske patent nr. 2.110.324 at bruken av natriumnitritt for dissosiering av aminer som opptrer ved konstitusjonen av farvestoffene fører til mere fortynnede oppløsninger. Således er vekten av oppløsningen som oppnås, for en del. 3-naftol . 9,13 6 deler i eksempel 10 og 8,819 deler i eksempel 11, eksempler som benytter natriumnitritt som dissosiasjonsmiddel, selv om denne vekt kun er 6,16 deler i eksemplene 15 til 17. Imidlertid nødvendiggjør bruken av alkylnitritter disses fremstilling og separering, noe som gjør fremstillingen av oppløsnin-gene av farvestoff mere tidkrevende, mere komplisert og mere the French patent no. 2,110,324 that the use of sodium nitrite for the dissociation of amines which occur in the constitution of the dyes leads to more dilute solutions. Thus, the weight of the resolution that is achieved is for a part. 3-naphthol. 9.13 6 parts in example 10 and 8.819 parts in example 11, examples using sodium nitrite as dissociating agent, although this weight is only 6.16 parts in examples 15 to 17. However, the use of alkyl nitrites necessitates their preparation and separation, which makes the preparation of the dye solutions more time-consuming, more complicated and more
belastende. - -: ■■<•''•-■■ burdensome. - -: ■■<•''•-■■
Imidlertid er det nu i laboratorier funnet'-atf ;det:'er mulig å oppnå oppløsninger i det minste like konsentrerte/ men på en mye enklere måte med som dissosiasjonsmiddel <å benytte natriumnitritt.. - -Y However, it has now been found in laboratories that it is possible to obtain solutions at least as concentrated, but in a much simpler way using sodium nitrite as a dissociation agent.
Foreliggende oppfinnelse angår derfor en fremgangsmåte for fremstilling av oppløsninger av azof arvestoff er hvori; dis-r sosiasjonen gjennomføres i vandig medium i nærvær av'et opp-løsningsmiddel som er blandbart med vann eller en blanding av oppløsningsmidler og der diazoforbindelsen som oppnås kobles med koblingskomponenten i en blanding inneholdende oppløsnings-midler og vann.Dissosiasjonen gjennomføres ved hjelp av''" ■ ■ natriumnitritt i nærvær av svovelsyre og natriumsulf at soiir - dannes fjernes fra oppløsningen ved filtrering. Oppløsnings-midler som kan benyttes i koblihgsmediet kan være etre avledet fra etylenglykol. Som oppløsningsmidler for koblingsmediét1 kan nevnes etanolaminer. De respektive proséntforhold'mellom vann og oppløsningsmiddel kan variere fra 10 : 90 til' 70 : 30 t: Det er overraskende å finne at natriumsulfatet som dannes1totalt eller så og si totalt felles ut og at, farvestoffer som oppnås helt og holdent forblir i oppløsning. The present invention therefore relates to a method for producing solutions of azof genetic material in which; The dissociation is carried out in an aqueous medium in the presence of a solvent which is miscible with water or a mixture of solvents and where the resulting diazo compound is coupled with the coupling component in a mixture containing solvents and water. The dissociation is carried out using '" ■ ■ sodium nitrite in the presence of sulfuric acid and sodium sulphate that is formed is removed from the solution by filtration. Solvents that can be used in the coupling medium can be ethers derived from ethylene glycol. Ethanolamines can be mentioned as solvents for the coupling medium. The respective percentage ratios between water and solvent may vary from 10 : 90 to' 70 : 30 t: It is surprising to find that the sodium sulphate which is formed totally or almost totally precipitates and that the dyes obtained remain entirely in solution.
Ved denne fremgangsmåte oppnås det oppløsninger'som omfatter .. , i. ; > . With this method, solutions are obtained which include .. , i. ; > .
40 til 65% farvestoff40 to 65% dye
10 til 40% av en blanding av oppløsningsmidler omfat- ... tende:<11>—<:>10 to 40% of a mixture of solvents comprise- ... tend:<11>—<:>
25 til 7 5% monoetylenglykol'<11>;-25 to 7 5% monoethylene glycol'<11>;-
7 5 til 25% av metyl- eller etyletereh av monoetylenglykol i., ; _ .r....•[.. 7 5 to 25% of methyl or ethyl ether of monoethylene glycol i., ; _ .r....•[..
0 til 30% av en blanding bestående av:0 to 30% of a mixture consisting of:
0 til 5% monoetanolamin 0 til 5% dietanolamin 0 to 5% monoethanolamine 0 to 5% diethanolamine
100 til 90% trietanolamin100 to 90% triethanolamine
10 til 3 0% vann ! ' ' - mindre enn 2% natriumsulf at.<!>' Fremgangsmåten ifølge oppfinnelsen er anvendelig "for• fremstilling av azofarvestoffene, mere spesielt til de av farve stoffene som -er kjent under navnene surt oransje 7 (natriumsaltet av [4-sulfobenzen]-1-azo-l-[2-hydroksynaftalen]) og surt oransje 8 (natriumsaltet av [4-sulfo-2-metylbenzen]-1-azo-l-[2-hydroksynaftalen]) såvel som blandinger derav. •■ . 10 to 3 0% water ! ' ' - less than 2% sodium sulphate.<!>' The method according to the invention is applicable "for production of the azo dyes, more particularly for those of colour the substances known under the names acid orange 7 (the sodium salt of [4-sulfobenzene]-1-azo-1-[2-hydroxynaphthalene]) and acid orange 8 (the sodium salt of [4-sulfo-2-methylbenzene]-1- azo-1-[2-hydroxynaphthalene]) as well as mixtures thereof. •■ .
Oppløsningene som oppnås erkarakterisert veden.meget stor oppløselighet i vann og en høy stabilitet ved lagring, , selv ved meget lave temperaturer. The solutions obtained are characterized by very high solubility in water and a high stability during storage, even at very low temperatures.
De følgende eksempler der alle deler er på vektbasis illustrerer oppfinnelsen uten å begrense den. <■ - , Eksempel 1 The following examples where all parts are by weight illustrate the invention without limiting it. <■ - , Example 1
173 deler sulfanilsyre blandes med 50 deler monoetylenglykol, 50 deler av metyleteren av monoetylenglykol, 50 • deler vann, 100 deler is og 53 deler 94%-ig svovelsyre.;. Deretter tilsettes 70 deler natriumnitritt i løpet av 30 minutter. :n Blandingen settes hen for reaksjon i 10 minutter inntil det ikke lenger er mulig å avfarve sulfanilsyre hvoretter. 14 4. deler .i., naftol tilsettes i løpet av 30 minutter, deretter tilsettes i løpet av 1 time 210 deler av en industriell blanding inrieholr dende 96% trietanolamin, 2% dietanolamin og 2% monoetanolamin Blandingen settes hen for reaksjon i 30 minutter og deretter'>.•;-'blir natriumsulfat separert ved filtrering. Det oppnås -772 deler av en oppløsning inneholdende '58,2% av trietanolaminsaltet av farvestoffet surt oransje 7. Ved tilsetning til denne opp-løsning av 23 deler vann oppnås 79 5 deler av en oppløsning med en konsentrasjon slik at 100 deler av oppløsningen er ekvi-valent 70 deler av det kommersielle farvestoff i form av et pulver. 173 parts of sulphanilic acid are mixed with 50 parts of monoethylene glycol, 50 parts of the methyl ether of monoethylene glycol, 50 • parts of water, 100 parts of ice and 53 parts of 94% sulfuric acid.;. 70 parts of sodium nitrite are then added over the course of 30 minutes. :n The mixture is set aside for reaction for 10 minutes until it is no longer possible to decolourise sulphanilic acid, after which. 14 4th parts i.e., naphthol is added over the course of 30 minutes, then 210 parts of an industrial mixture containing 96% triethanolamine, 2% diethanolamine and 2% monoethanolamine are added over the course of 1 hour. The mixture is set aside for reaction for 30 minutes and then'>.•;-'the sodium sulfate is separated by filtration. 772 parts of a solution containing 58.2% of the triethanolamine salt of the dye acid orange 7 are obtained. By adding to this solution 23 parts of water, 795 parts of a solution are obtained with a concentration such that 100 parts of the solution are equivalent to 70 parts of the commercial dye in the form of a powder.
Denne oppløsning er helt stabil ved lagring. Etter et lagringstidsrom på 1 måned ved -20°C er det tilstrekkelig å : gjenoppvarme til 0°C for å oppnå en oppløsning helt komformt. med det opprinnelige produkt og som ikke viser noen tegn til krystallisering. Vekten av oppløsningen pr. del 3-naftol er 5,52 deler. Oppløsningen inneholder mindre enn 1% mineralsyrer. This solution is completely stable during storage. After a storage period of 1 month at -20°C, it is sufficient to: reheat to 0°C to obtain a solution completely comfortable. with the original product and which shows no signs of crystallization. The weight of the solution per part 3-naphthol is 5.52 parts. The solution contains less than 1% mineral acids.
Eksempel 2Example 2
Hvis man arbeider som i eksempel 1, men med 150 delerIf you work as in example 1, but with 150 parts
av blandingen av alkanolaminer i stedet for 210 deler varer koblingen ca. 6 timer i stedet for 30 minutter. Etter separering av natriumsulfatét ved filtrering ved 40°C, oppnås 720 deler av en'oppløsning inneholdende 62,4% farvestoff. Ved til- of the mixture of alkanolamines instead of 210 parts, the coupling lasts approx. 6 hours instead of 30 minutes. After separation of the sodium sulphate by filtration at 40°C, 720 parts of a solution containing 62.4% dye are obtained. By to-
setning av vann reguleres konsentrasjonen av oppløsningen ■ til den ønskede verdi. Eksempel 3 addition of water, the concentration of the solution ■ is adjusted to the desired value. Example 3
187 deler 2-aminotoluen-5-sulfonsyre blandes med 20O deler monoetylenglykol og 200 deler av metyleteren av monoetylenglykol hvoretter det tilsettes 100 deler is og deretter 187 parts of 2-aminotoluene-5-sulfonic acid are mixed with 200 parts of monoethylene glycol and 200 parts of the methyl ether of monoethylene glycol, after which 100 parts of ice are added and then
53 deler 94%-ig svovelsyre. 70 deler natriumnitritt tilsettes deretter i løpet av 30 minutter. Blandingen settes hen for . reaksjon inntil det ikke-diazoterte amin ikke lenger kan opp-dages. Suspensjonen blir deretter i løpet av 30 minutter helt på en 20°C varm oppløsning av 144 deler> 3-naftol i 120 deler teknisk trietanolamin inneholdende 2% dietanolamin og 2% monoetanolamin. Etter at koblingen er ferdig separeres natriumsulf atet ved filtrering. Det oppnås 9 50 deler av én -'< oppløsning inneholdende 48% farvestoff.<:>Ved tilsetning '■ av ■'"vann reguleres konsentrasjonen til' den ønskede verdi. Opp- ' løsningen er perfekt stabil ved lagring. Den inneholder mindre enn 1% mineralsalter. Eksempel 4 53 parts 94% sulfuric acid. 70 parts of sodium nitrite are then added over 30 minutes. The mixture is set aside for . reaction until the non-diazotized amine can no longer be detected. The suspension is then poured over the course of 30 minutes on a 20°C hot solution of 144 parts > 3-naphthol in 120 parts of technical triethanolamine containing 2% diethanolamine and 2% monoethanolamine. After the coupling is complete, the sodium sulphate is separated by filtration. 9 50 parts of one -'< solution containing 48% dye is obtained.<:>By adding '■ of ■'"water, the concentration is regulated to' the desired value. The solution is perfectly stable when stored. It contains less than 1% mineral salts Example 4
Hvis man i stedet for å benytte 200 deler étylenglykol og 200 deler metyleter av étylenglykol benytter 100 deler !av den første og 300 deler av den andre eller 300 av den førster og 10 0 av den andre, oppnås oppløsninger som viser de samme karakteristika. Eksempel 5 If, instead of using 200 parts of ethylene glycol and 200 parts of methyl ether of ethylene glycol, one uses 100 parts of the first and 300 parts of the second or 300 of the first and 100 of the second, solutions are obtained which show the same characteristics. Example 5
Diasoforbindelsen fremstilles fra 173 deler sulfanilsyre i henhold til det som er angitt i eksempel 1 hvoretter den oppnådde suspensjon, i løpet av 30 minutter helles i en oppløsning av 144 deler 3-naftol i 210 deler trietanolamin. Etter filetrering oppnår man den samme oppløsning som i'eksempel 1. ''' ' ' Eksempel 6 ''' ■'' ' The diazo compound is prepared from 173 parts of sulphanilic acid according to what is stated in example 1, after which the resulting suspension is poured into a solution of 144 parts of 3-naphthol in 210 parts of triethanolamine within 30 minutes. After filtration, the same solution as in example 1 is obtained. ''' ' ' Example 6 ''' ■'' '
Hvis i eksempel 3 de 187 deler 2-aminotoluen-5-sulfon-syre erstattes med 168,3 deler av det samme produkt og 17,3 deler sulfanilsyre oppnås en oppløsning som inneholder en blanding av 9 0% av farvestoffet surt oransje 8 og 10% av farvestoffet surt oransje 7. ' .. ''--li If in example 3 the 187 parts of 2-aminotoluene-5-sulfonic acid are replaced by 168.3 parts of the same product and 17.3 parts of sulphanilic acid, a solution is obtained which contains a mixture of 90% of the dye acid orange 8 and 10 % of the dye acid orange 7. ' .. ''--li
Eksempel 7Example 7
187 deler 2-aminotoluen-5-sulfonsyre, 100 deler monoetylenglykol, 100 deler metyleter av monoetylenglykol, 100 deler is og 70 deler natriumnitritt blandes. 53 deler 9.4%.r-ig svovelsyre tilsettes i løpet av 15 minutter og diasoser.ings-reaksjonen tillates å fortsette inntil det diazoterbare amin ikke lenger avfarves. Deretter tilsettes 144 deler . 3-rnaftol . 187 parts of 2-aminotoluene-5-sulfonic acid, 100 parts of monoethylene glycol, 100 parts of methyl ether of monoethylene glycol, 100 parts of ice and 70 parts of sodium nitrite are mixed. 53 parts of 9.4% r.g. sulfuric acid are added over 15 minutes and the diazotization reaction is allowed to continue until the diazotizable amine is no longer decolorized. Then 144 parts are added. 3-rnaphthol.
i løpet av 3 0 minutter hvoretter det i løpet av 1 time.tilr settes industriell trietanolamin i en mengde av 210 deler;, Blandingen settes hen for reaksjon i 30 minutter, oppvarmes deretter til 40°C hvoretter natriumsulfat separeres ved filtrering. Det oppnås 810 deler av en oppløsning inneholdende 57% av farvestoffet surt oransje 8..C Eksempel 8 in the course of 30 minutes, after which, in the course of 1 hour, industrial triethanolamine is added in an amount of 210 parts;, The mixture is set aside for reaction for 30 minutes, then heated to 40°C, after which sodium sulfate is separated by filtration. 810 parts of a solution containing 57% of the dye acid orange 8..C Example 8 are obtained
173 deler sulfanilsyre blandes med 40.deler monoetylenglykol, 40 deler metyleter av monoetylenglykol og 120 deler vann. I løpet av 1 time tilsettes 70 deler natriumnitritt og deretter i 1 time 53 deler 94%-ig svovelsyre. Diazoteringen tillates å gå til ende hvoretter 144 deler 3-naftol tilsettes. Deretter tilsettes i løpet av 1 time 180 deler ren trietanolamin eller den samme blanding som i eksempel 1. Man tillater blandingen å reagere i 30 minutter, oppvarmes til 60°C, og 173 parts of sulfanilic acid are mixed with 40 parts of monoethylene glycol, 40 parts of methyl ether of monoethylene glycol and 120 parts of water. In the course of 1 hour, 70 parts of sodium nitrite are added and then in 1 hour 53 parts of 94% sulfuric acid. The diazotization is allowed to go to completion after which 144 parts of 3-naphthol are added. 180 parts of pure triethanolamine or the same mixture as in example 1 are then added over the course of 1 hour. The mixture is allowed to react for 30 minutes, heated to 60°C, and
natriumsulfatet separeres ved filtrering. Man oppnår 7.10, ,:deler av en oppløsning inneholdende ca. 62% farvestoff der konsentrasjonen reguleres til en verdi slik at 140 deler av oppløsningen tilsvarer 100 deler av det kommersielle produktpulver.; Denne the sodium sulfate is separated by filtration. One obtains 7.10, ,:parts of a solution containing approx. 62% dye where the concentration is regulated to a value so that 140 parts of the solution corresponds to 100 parts of the commercial product powder.; This
operasjon gjennomføres enten ved å tilsette vann eller monoetylenglykol eller metyleteren ..av monoetylenglykol eller av en blanding av to av disse produkter,der ett av dem,er vann. operation is carried out either by adding water or monoethylene glycol or the methyl ether ..of monoethylene glycol or by a mixture of two of these products, where one of them is water.
Claims (11)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8013144A FR2484431A1 (en) | 1980-06-13 | 1980-06-13 | PROCESS FOR THE PREPARATION OF CONCENTRATED SOLUTIONS OF AZO DYES AND SOLUTIONS THUS OBTAINED |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO811997L true NO811997L (en) | 1981-12-14 |
Family
ID=9243050
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO811997A NO811997L (en) | 1980-06-13 | 1981-06-12 | PROCEDURE FOR PREPARING CONCENTRATED SOLUTIONS OF AZO COLORS. |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS5728163A (en) |
| AU (1) | AU7169181A (en) |
| BE (1) | BE889088A (en) |
| BR (1) | BR8103760A (en) |
| DE (1) | DE3123236A1 (en) |
| DK (1) | DK251981A (en) |
| ES (1) | ES503014A0 (en) |
| FI (1) | FI811844L (en) |
| FR (1) | FR2484431A1 (en) |
| GB (1) | GB2079771A (en) |
| IT (1) | IT1144810B (en) |
| NL (1) | NL8102811A (en) |
| NO (1) | NO811997L (en) |
| SE (1) | SE8103715L (en) |
| ZA (1) | ZA813939B (en) |
Families Citing this family (9)
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|---|---|---|---|---|
| JPS59148207A (en) * | 1983-02-14 | 1984-08-24 | 昭和電線電纜株式会社 | Crosslinked polyethylene insulated cable |
| DE3574721D1 (en) * | 1984-04-09 | 1990-01-18 | Hoechst Ag | METHOD FOR PRODUCING LIQUID, LOW-SALT, AQUEOUS DYE PREPARATIONS. |
| DE3413315A1 (en) * | 1984-04-09 | 1985-10-17 | Hoechst Ag, 6230 Frankfurt | METHOD FOR PRODUCING LIQUID, LOW-SALT, AQUEOUS REACTIVE DYE PREPARATIONS |
| DE3426931A1 (en) * | 1984-07-21 | 1986-01-23 | Hoechst Ag, 6230 Frankfurt | METHOD FOR PRODUCING LIQUID, LOW-SALT, AQUEOUS REACTIVE DYE PREPARATIONS |
| CH675425A5 (en) * | 1988-08-24 | 1990-09-28 | Ciba Geigy Ag | |
| DE19621840A1 (en) * | 1996-05-31 | 1997-12-04 | Basf Ag | Process for the preparation of phenylazonaphthalenes |
| US7008911B2 (en) | 2002-09-06 | 2006-03-07 | Ecolab, Inc. | Non-surfactant solubilizing agent |
| US6767881B1 (en) | 2003-03-19 | 2004-07-27 | Ecolab, Inc. | Cleaning concentrate |
| FR2862656B1 (en) * | 2003-11-26 | 2007-01-12 | Sebia Sa | CONCENTRATED AZO COLORANT SOLUTION, COLORING KIT COMPRISING THE SAME, AND PROCESS FOR PREPARING A PROTEIN COLORING SOLUTION |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE631379A (en) * | ||||
| US3681320A (en) * | 1970-01-13 | 1972-08-01 | Du Pont | Preparation of disazo j acid urea dyestuffs |
| FR2109806A5 (en) * | 1970-10-07 | 1972-05-26 | Althouse Tertre | Stable tinctorial prepns for dyeing paper by - direct application |
| DE2049620C3 (en) * | 1970-10-09 | 1975-04-30 | Basf Ag, 6700 Ludwigshafen | Stable, concentrated, acidic stock solutions of anionic dyes, processes for their preparation and their use |
| DE2051303C3 (en) * | 1970-10-20 | 1978-12-21 | Bayer Ag, 5090 Leverkusen | Polyhydroxyalkylamine salts of anionic dyes |
| DE2209478C3 (en) * | 1972-02-29 | 1975-04-10 | Basf Ag, 6700 Ludwigshafen | Process for the preparation of concentrated solutions of metal-free anionic azo dyes containing sulfonic acid groups |
| US4082742A (en) * | 1973-08-17 | 1978-04-04 | E. I. Du Pont De Nemours And Company | Process for preparing an aqueous disazo dye concentrate |
| GB1527602A (en) * | 1974-12-23 | 1978-10-04 | Clayton Aniline Co Ltd | Preparation of concentrated aqueous solutions of tertiary amine salts of disazo dyestuffs |
| DE2527703A1 (en) * | 1975-06-21 | 1977-01-13 | Bayer Ag | PROCESS FOR THE PREPARATION OF CONCENTRATED SOLUTIONS OF ANIONIC COLORS |
| US4043752A (en) * | 1975-12-17 | 1977-08-23 | E. I. Du Pont De Nemours And Company | Phenylazoaminophenylpyrazole acid dye solutions containing two nonionic surfactants |
-
1980
- 1980-06-13 FR FR8013144A patent/FR2484431A1/en active Pending
-
1981
- 1981-06-04 BE BE0/204992A patent/BE889088A/en not_active IP Right Cessation
- 1981-06-10 DK DK251981A patent/DK251981A/en not_active Application Discontinuation
- 1981-06-11 NL NL8102811A patent/NL8102811A/en not_active Application Discontinuation
- 1981-06-11 ZA ZA813939A patent/ZA813939B/en unknown
- 1981-06-11 DE DE19813123236 patent/DE3123236A1/en not_active Withdrawn
- 1981-06-11 IT IT67801/81A patent/IT1144810B/en active
- 1981-06-12 ES ES503014A patent/ES503014A0/en active Granted
- 1981-06-12 GB GB8118078A patent/GB2079771A/en not_active Withdrawn
- 1981-06-12 SE SE8103715A patent/SE8103715L/en not_active Application Discontinuation
- 1981-06-12 NO NO811997A patent/NO811997L/en unknown
- 1981-06-12 FI FI811844A patent/FI811844L/en not_active Application Discontinuation
- 1981-06-12 BR BR8103760A patent/BR8103760A/en unknown
- 1981-06-12 AU AU71691/81A patent/AU7169181A/en not_active Abandoned
- 1981-06-12 JP JP9068481A patent/JPS5728163A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IT1144810B (en) | 1986-10-29 |
| SE8103715L (en) | 1981-12-14 |
| ES8300825A1 (en) | 1982-11-01 |
| FR2484431A1 (en) | 1981-12-18 |
| ZA813939B (en) | 1982-06-30 |
| BR8103760A (en) | 1982-03-02 |
| GB2079771A (en) | 1982-01-27 |
| DE3123236A1 (en) | 1982-06-16 |
| JPS5728163A (en) | 1982-02-15 |
| AU7169181A (en) | 1981-12-17 |
| FI811844L (en) | 1981-12-14 |
| BE889088A (en) | 1981-12-04 |
| ES503014A0 (en) | 1982-11-01 |
| NL8102811A (en) | 1982-01-04 |
| IT8167801A0 (en) | 1981-06-11 |
| DK251981A (en) | 1981-12-14 |
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