NO163993B - PROCEDURE TE FOR PREPARING A RECONSTITUTABLE PRODUCT - Google Patents
PROCEDURE TE FOR PREPARING A RECONSTITUTABLE PRODUCT Download PDFInfo
- Publication number
- NO163993B NO163993B NO860863A NO860863A NO163993B NO 163993 B NO163993 B NO 163993B NO 860863 A NO860863 A NO 860863A NO 860863 A NO860863 A NO 860863A NO 163993 B NO163993 B NO 163993B
- Authority
- NO
- Norway
- Prior art keywords
- aminophenol
- sulfonamide
- mixture
- naphthylamine
- nitro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 239000000203 mixture Substances 0.000 claims description 12
- 238000010168 coupling process Methods 0.000 claims description 11
- AVQFHKYAVVQYQO-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonamide Chemical compound NC1=CC(S(N)(=O)=O)=CC=C1O AVQFHKYAVVQYQO-UHFFFAOYSA-N 0.000 claims description 10
- 230000008878 coupling Effects 0.000 claims description 10
- 238000005859 coupling reaction Methods 0.000 claims description 10
- 239000000987 azo dye Substances 0.000 claims description 7
- SWFNPENEBHAHEB-UHFFFAOYSA-N 2-amino-4-chlorophenol Chemical compound NC1=CC(Cl)=CC=C1O SWFNPENEBHAHEB-UHFFFAOYSA-N 0.000 claims description 5
- GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 claims description 5
- VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 238000006193 diazotization reaction Methods 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000001869 cobalt compounds Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 description 16
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 8
- 229910017052 cobalt Inorganic materials 0.000 description 5
- 239000010941 cobalt Substances 0.000 description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- DOPJTDJKZNWLRB-UHFFFAOYSA-N 2-Amino-5-nitrophenol Chemical compound NC1=CC=C([N+]([O-])=O)C=C1O DOPJTDJKZNWLRB-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- RHPXYZMDLOJTFF-UHFFFAOYSA-N 3-amino-4-hydroxy-5-nitrobenzenesulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC([N+]([O-])=O)=C1O RHPXYZMDLOJTFF-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Fremgangsmåte til fremstilling av blandkompleks- Process for the production of mixed complex-
azofargestoffer av typen 1:2, inneholdende kobolt. azo dyes of the 1:2 type, containing cobalt.
Oppfinnelsen vedrører en fremgangsmåte til fremstilling av blandkompleks-azofargestoffer av typen 1:2, som inneholder kobolt og har formel The invention relates to a process for the production of mixed complex azo dyes of the type 1:2, which contain cobalt and have the formula
hvori Y betyr et kloratom eller en nitrogruppe. wherein Y means a chlorine atom or a nitro group.
Man kjenner metallkompleks-azofargestoffer til farging Metal complex azo dyes are known for dyeing
av ull og polyamidfibre med svart og grått, inneholdende ett metallatom pr. 2 molekyler monoazofargestoffer. Slike fargestoffer fremstilles f.eks. ved kopling av diazoterte 2-aminofenol-4-sulfonamider med 2-naftylamin i surt medium, surgjort med eddiksyre eller mineralsyre, og omdannes deretter under anvendelse av metallavgivende midler, til komplekser av typen 1:2. of wool and polyamide fibers with black and grey, containing one metal atom per 2 molecules of monoazo dyes. Such dyes are produced e.g. by coupling diazotized 2-aminophenol-4-sulfonamides with 2-naphthylamine in an acidic medium, acidified with acetic acid or mineral acid, and then converted using metal-releasing agents, into complexes of the type 1:2.
I mange tilfelle kan man også få monoazofargestoffer med generell'formel I, In many cases, monoazo dyes of general formula I can also be obtained,
hvori X betegner nitro- eller sulfogrupper, når man i ovennevnte reaksjon i stedet for 2-naftylamin anvender 2-naftylamin-l-sulfonsyre, eller o-aminofenolderivater med tilsvarende høy koplingsenergi, hvilken energi er tilstrekkelig til fortrengning av sulfogruppen i 2-naftylamin-l-sulfonsyren og for dannelse av monoazofargestoffet. in which X denotes nitro or sulfo groups, when in the above reaction instead of 2-naphthylamine 2-naphthylamine-l-sulfonic acid is used, or o-aminophenol derivatives with correspondingly high coupling energy, which energy is sufficient to displace the sulfo group in 2-naphthylamine- the l-sulfonic acid and to form the monoazo dye.
Fra sveitsisk patent nr. 298.883 er det kjent å frem-stille azofargestoffer ved kopling av diazotert 6-nitro-2-aminofenol-4-sulfonsyre méd 2-naftylamin-l-sulfonsyre i et svakt surt til svakt alkalisk medium, hvorved sulfogruppen samtidig sikrer diazogruppen. From Swiss patent no. 298,883, it is known to produce azo dyes by coupling diazotized 6-nitro-2-aminophenol-4-sulfonic acid with 2-naphthylamine-1-sulfonic acid in a weakly acidic to weakly alkaline medium, whereby the sulfo group simultaneously ensures the diazo group.
Sveitsisk patent nr. '.,02.050 og polsk patent nr. 45.016 vedrører fremstillingen av monoazofargestoffer med formel 2, ved kopling av diazotert 5-nitro-2-aminofenol med 2-naftylamin-l-sulfonsyre i surt miljø i nærvær av arylsulfonatforbindelser. Mono-azofargestof f er ifølge formlene 1 og 2 kan omdannes til metallkom-plekser som er i stand til å farge ull og polyamidfibre, eller som kan brukes som lakkfargestoffer i organiske oppløsningsmidler. Swiss Patent No. 02,050 and Polish Patent No. 45,016 relate to the production of monoazo dyes of formula 2, by coupling diazotized 5-nitro-2-aminophenol with 2-naphthylamine-1-sulfonic acid in an acidic environment in the presence of arylsulfonate compounds. According to formulas 1 and 2, mono-azo dyes f can be converted into metal complexes which are able to dye wool and polyamide fibres, or which can be used as lacquer dyes in organic solvents.
Fremgangsmåten i henhold til oppfinnelsen muliggjør fremstilling av nye fullverdige metallkompleksazofargestoffer som har den foran angitte formel. The method according to the invention enables the production of new full-fledged metal complex azo dyes having the above formula.
Fremgangsmåten ifølge oppfinnelsen er karakterisert ved at en blanding ivstøkiometrisk forhold av 2-aminofenol-lJ-sulfon-amid og 4-klor-2-aminofenol, eJler en blanding av 2-aminofenol-4-sulfonamid og 4-nitro-2-aminofenol, underkastes diazotering og kopling med 2-naftylamin-l-sulfonsyre i mineralsurt medium, og at monoazo-fargestof fblandingen ifølge formlene The method according to the invention is characterized in that a stoichiometric mixture of 2-aminophenol-1J-sulfonamide and 4-chloro-2-aminophenol, or a mixture of 2-aminophenol-4-sulfonamide and 4-nitro-2-aminophenol, is subjected to diazotization and coupling with 2-naphthylamine-1-sulfonic acid in a mineral acid medium, and that the monoazo dye mixture according to the formulas
eller ifølge formlene or according to the formulas
isoleres og på kjent måte behandles med koboltforbindelser. is isolated and treated in a known manner with cobalt compounds.
Fargestoffene danner blandkomplekser som inneholder ett metallatom pr. 2 molekyler monoazofargestoff. Til tross for innholdet av bare én sulfonamidgruppe i molekylet, utmerker disse fargestoffer seg ved stor vannoppløselighet. De fikseres godt på ull og polyamidfibre fra nøytrale vandige bad og kan også anvendes for lærfarging. Artikler farget med disse forbindelser utmerker seg ved høy bestandig-het mot fuktighet, og ved god lysbestandighet. The dyes form mixed complexes containing one metal atom per 2 molecules of monoazo dye. Despite the content of only one sulfonamide group in the molecule, these dyes are distinguished by high water solubility. They fix well on wool and polyamide fibers from neutral aqueous baths and can also be used for leather dyeing. Articles dyed with these compounds are distinguished by high resistance to moisture and good light resistance.
Fremgangsmåten ifølge oppfinnelsen beror på at 2-amino-fenol-4-sulfonamid og 4-klor-2-aminofenol, eller 2-aminofenol-4-sulfonamid og 4-nitro-2-aminofenol i s-tøkiomet risk forhold underkastes diazoterings- og koplings-prosesser med 2-naftylamin-l-sulfonsyre i mineralsurt medium ved en temperatur på 55-60°C, og at den spesielle blanding, av monoazof argestof f er ifølge formel 3 og 4 eller formel 3 og 5 på kjent måte behandles med forbindelser som avgir kobolt, fortrinnsvis koboltklorid, under dannelse av det koboltholdige fargestoff. The method according to the invention is based on 2-amino-phenol-4-sulfonamide and 4-chloro-2-aminophenol, or 2-aminophenol-4-sulfonamide and 4-nitro-2-aminophenol in a s-stoichiometric ratio being subjected to diazotization and coupling processes with 2-naphthylamine-l-sulfonic acid in a mineral acid medium at a temperature of 55-60°C, and that the special mixture, of monoazof argestof f is according to formula 3 and 4 or formula 3 and 5 is treated in a known manner with compounds which emit cobalt, preferably cobalt chloride, during formation of the cobalt-containing dye.
Ved anvendelsen i henhold til oppfinnelsen av de spesielle aktive bestanddeler, nemlig 2-aminofenol-4-sulfonamid, 4-klor-2-aminofenol eller 4-nitro~2-aminofenor, oppnås en lavere- koplingsenergi enn med de aminer som. er anvendt tidligere. Man kunne ikke- forut-se at blandingen av diazoterte forbindelser av.4-klor-2-aminofenol When using according to the invention the special active ingredients, namely 2-aminophenol-4-sulfonamide, 4-chloro-2-aminophenol or 4-nitro~2-aminophenor, a lower coupling energy is achieved than with the amines which. has been used previously. One could not foresee that the mixture of diazotized compounds of 4-chloro-2-aminophenol
med 2-aminofenol-4-sulfonamid eller 4-nitro-2-amin6fenol med 2-amino-fenol-4-sulfonamid skulle, ha en så høy koblingsenergi- som er tilstrekkelig til fortrengning av sulfogruppen i. 2-naftylamin-l-sulfonsy-ren, under dannelse av.de tilsvarende- monoazofargestoffer. with 2-aminophenol-4-sulfonamide or 4-nitro-2-amine6phenol with 2-amino-phenol-4-sulfonamide should have such a high coupling energy that is sufficient for displacement of the sulfo group in 2-naphthylamine-l-sulfonsy -pure, with the formation of the corresponding monoazo dyes.
Oppfinnelsen skal belyses ved nedenstående eksempler. Eksempel 1. The invention shall be illustrated by the examples below. Example 1.
9,4 2-aminofenol-4-sulfonamid og* 7,2 g 4-klor-2-aminoTenoI oppløses i 500 ml vann og 30 g 30%- ig saltsyre ved en temperatur på 40°-50°C 9.4 2-aminophenol-4-sulfonamide and* 7.2 g of 4-chloro-2-aminoTenoI are dissolved in 500 ml of water and 30 g of 30% hydrochloric acid at a temperature of 40°-50°C
Oppløsningen avkjøles med is til 5°-10°C og man til-drypper 23 g 30#-og natriumnitrit i løpet av 30 minutter ved denne temperatur. I separat beholder tilsettes 24 g 2-naftylamin-l-sulfonsyre til 500 ml vann, som blandes i 10 timer. Til den således fremstilte suspen&j-on settes ovennevnte blanding av diazotert for-bindelse, og blandingene•røres i 8 timer ved værelsestemperatur. Deretter blir blandingen oppvarmet, til 60°C og holdes ved 55°-60°C i 30 timer inntil koblingen er fullendt. Den avkjølte fargestoffsuspensjon filtreres, vaskes med en mettet oppløsning av natriumklorid inntil man får en nøytral reaksjon og avpresses godt. Den fremstilte fargestoff-pasta opptas i 600 ml vann og røres til man får en enhetlig suspensjon, som oppvarmes til 80°C og deretter tilsettes 35 g 50$-ig natrium-hydroksydoppløsning. Til den fremstilte oppløsning helles 50 ml varm oppløsning inneholdende 13 g koboltklorid, og man blander i 3 timer ved 85°-90°C. The solution is cooled with ice to 5°-10°C and 23 g of 30# sodium nitrite are added dropwise over the course of 30 minutes at this temperature. In a separate container, 24 g of 2-naphthylamine-1-sulfonic acid is added to 500 ml of water, which is mixed for 10 hours. The above-mentioned mixture of diazotized compounds is added to the thus prepared suspension, and the mixtures are stirred for 8 hours at room temperature. The mixture is then heated to 60°C and held at 55°-60°C for 30 hours until coupling is complete. The cooled dye suspension is filtered, washed with a saturated solution of sodium chloride until a neutral reaction is obtained and squeezed well. The produced dye paste is taken up in 600 ml of water and stirred until a uniform suspension is obtained, which is heated to 80°C and then 35 g of 50% sodium hydroxide solution is added. 50 ml of hot solution containing 13 g of cobalt chloride is poured into the prepared solution and mixed for 3 hours at 85°-90°C.
Etter å ha slått fast at metalliser-ingen er ferdig, avsluttes oppvarmningen, man tilsetter 50 g koksalt og nøytraliserer med 30$-ig saltsyreoppløsning til pH = 7,5 — 8. Det utskilte bunn-fall frafiltreres, avpresses godt og tørkes ved en temperatur på 80-90°C. After establishing that the metallization is complete, the heating is terminated, 50 g of common salt is added and neutralized with a 30% hydrochloric acid solution to pH = 7.5 - 8. The separated precipitate is filtered off, squeezed well and dried in a temperature of 80-90°C.
- Eksempel !!_._ - Example !!_._
Et svart fargestoff med grønn sjattering og like god holdbarhet som ovennevnte forbindelser kan fremstilles ved kobling av en diazoteringsblanding inneholdende 9,4 g 2-aminofenol-4-sulfonamid og 7,4 g 4-nitro-2-aminofenol med 2-naftylamin-l-sulfonsyre og på-følgende koboltbehandling som beskrevet i eksempel I. A black dye with a green tint and as good durability as the above compounds can be prepared by coupling a diazotization mixture containing 9.4 g of 2-aminophenol-4-sulfonamide and 7.4 g of 4-nitro-2-aminophenol with 2-naphthylamine-l -sulfonic acid and subsequent cobalt treatment as described in example I.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO860863A NO163993C (en) | 1986-03-07 | 1986-03-07 | PROCEDURE FOR MANUFACTURING A RECONSTITUTABLE FOOD PRODUCT. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO860863A NO163993C (en) | 1986-03-07 | 1986-03-07 | PROCEDURE FOR MANUFACTURING A RECONSTITUTABLE FOOD PRODUCT. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO860863L NO860863L (en) | 1987-09-08 |
| NO163993B true NO163993B (en) | 1990-05-14 |
| NO163993C NO163993C (en) | 1990-08-22 |
Family
ID=19888792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO860863A NO163993C (en) | 1986-03-07 | 1986-03-07 | PROCEDURE FOR MANUFACTURING A RECONSTITUTABLE FOOD PRODUCT. |
Country Status (1)
| Country | Link |
|---|---|
| NO (1) | NO163993C (en) |
-
1986
- 1986-03-07 NO NO860863A patent/NO163993C/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO860863L (en) | 1987-09-08 |
| NO163993C (en) | 1990-08-22 |
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