CS259291B1 - 4,5,6,7-tetrachloro-2- (2-benzothiazolyl) -1,3-indanedione and its preparation - Google Patents
4,5,6,7-tetrachloro-2- (2-benzothiazolyl) -1,3-indanedione and its preparation Download PDFInfo
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- CS259291B1 CS259291B1 CS87107A CS10787A CS259291B1 CS 259291 B1 CS259291 B1 CS 259291B1 CS 87107 A CS87107 A CS 87107A CS 10787 A CS10787 A CS 10787A CS 259291 B1 CS259291 B1 CS 259291B1
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Abstract
Oranžový pigment na báze novej zlúčeniny 4,5,6,7-tetrahchlór-2-(2-benzotiazolyl) - -1,3-indandiónu vzorce I vhodný na farbenie PVC, polyetylénu, polyesterového hodvábu, metakrylových živíc a podobných materiálov. Spůsob výroby zlúčeniny vzorca I sa vyznačuje tým, že sa kondenzuje 3,4,5,6-tetrachlórftalanhydrid s 2- -metylbenzotiazolom za přítomnosti octanu draselného pri teplote 140—150 °G.Orange pigment based on the new compound 4,5,6,7-tetrachloro-2-(2-benzothiazolyl)-1,3-indanedione of formula I suitable for dyeing PVC, polyethylene, polyester silk, methacrylic resins and similar materials. The method for producing the compound of formula I is characterized in that 3,4,5,6-tetrachlorophthalic anhydride is condensed with 2-methylbenzothiazole in the presence of potassium acetate at a temperature of 140-150 °C.
Description
Vynález sa týká 4,5,6,7-tetrachlór-2-(2-benzotiazolyl] 1,3-indandiónu vzorce; I,
Cl
ČíAxCO I o! c-r'VC0
Cl ( I ) a sposobu jeho výroby vyznačeného tým, že sa kondenzuje! 2-metylbenzotiazol s 3,4,5,6-tetrachlórftalanhydridom v tavenine za přítomnosti bázy. Produkt reakcie ako oranžový až červený, pigment je vhodný na farbenie PVC, polyesterového· hodvábu, polypropylénu, polyetylénu, termoplastickej gumy a podobných materiálov. V literatuře su známe pyridinové alebo chipolínpvé deriváty 1,3-indandiónu ako fafebné pigmenty pod názvom alfa alebo gama-pyroftalóny alebo chinoftalón, resp. chinaldínová žlť. Uvedené pigmenty sú velmi vhodné na larbenie PVC, polyetylénu, polyesterového hodvábu, polystyrénu metakrylových živíc a podobných materiálov a sa v uvedených odvetviach farbiarskeho priemyslu využívajú. Z rozsiahlej patentovej a časopiseckej literatúry venovanej ftalónom možno uviesť nasledujúce citácie: Schefczik E. Ger. Offen 2 132 681; Hunter C., Shellburn US 3 904 420; Gailis A., Kolesnikov V. A., Silens E.; Latv. P. S. R. Zmat. Akad. Vestis 20 (1978); Nagahama S., Shimada K., Harada T., Koga M.: Japan Kokai 7847, 439.
Teraz bolo zistené, že 2-metylbenzotiazol sa kondenzuje s 3,4,5,6-tetrachlórftalanhydridom pri teplote 140—150 °C v přítomnosti CH3COOK ako bázy a poskytuje v jednom syntetickom stupni intenzívně oranžový, velmi nerozpustný pigment vo vysokom výtažku (cca 90 %).
Pigment vo vodě a v běžných organických rozpúšťadlách aiko sú etanol, metanol, chlo- roform, dichlórmetán, acetón, kyselina octová, sa nerozpúšťa, v dimetylsulfoxide za studená málo, za tepla sa rozpúšťa dobré, takže sa može z dimetylsulfoxidu krystalizovat Připravená zlúčenina podlá vynálezu je stála, stálofarebná a sýtofarebná, zvlášť ked sa vylúči zo zásaditého prostredia. K získaniu vhodného odtieňa so móže použiť aj v zmesiach s inými farebnými pigmentami.
Nasledujúci příklad ozřejmuje, ale neobmedzuje možnosti využitia podlá vynálezu. Příklad 1 K zmesi 3,4,5,6-tetrachlórftalanhydridu (0,1 mólu) a 2-metylbenzotiazolu (0,12 mólu) sa přidá přetavený octan draselný (0,01 mólu), intenzívně sa mieša a zahrieva na 140—150 °C 1 h za súčasného odvádzania kondenzačnej vody. Po ukončení reakcie za stálého miešania reakčná zmes sa ochladí přibližné na 70 °C a přidá sa k nej 50 cm3 etanolu, mieša sa 30 min., potom sa přidá 30 cm3 5 %-ného etanolátu sodného a pokračuje sa v miešaní pri teplote 25—30 °C 1 h.
Vylúčená zrazenina sa odsaje, premyje etanolom, vodou a vysuší, može sa prekryštalizovať z dimetylsulfoxidu, ale aj bez kryštalizácie je produkt dostatočne čistý pře ďalšie použitie.
Analýza pre 4,5,6,7-tetrachlór-2-(2-benzotiazolyl]-l,3-indandión, sumárneho vzorca C16H5O2NCUS (M = 417,0), teplota topenia je nad 360 °C, do teploty 365 °C sa nerozkládá, Amax (v DMSO po zahriati) = 388, 578 nm; vypočítané: 46,07 % C, 1,20 % H, 3,35 % N, 33,99 % Cl; zistené: 46,28 % C, 1,55 % H, 3,58 % N, 33,61 % Cl.
The invention relates to 4,5,6,7-tetrachloro-2- (2-benzothiazolyl) 1,3-indanedione of the formula;
Cl
WhExCO I o! c-r'VC0
Cl (I) and the process for its production characterized in that it is condensed! 2-methylbenzothiazole with 3,4,5,6-tetrachlorophthalic anhydride in the presence of a base. The reaction product as orange to red, the pigment is suitable for dyeing PVC, polyester silk, polypropylene, polyethylene, thermoplastic rubber and the like. In the literature, pyridine or chipolinium derivatives of 1,3-indanedione are known as phosphorous pigments under the name alpha or gamma-pyrophthalones or quinophthalones, respectively. quinaldine yellow. Said pigments are very suitable for larvae of PVC, polyethylene, polyester silk, polystyrene methacrylic resins and the like and are used in the dyeing industry. From the extensive patent and magazine literature on phthalones, the following citations can be cited: Schefczik E. Ger. Offen 2,132,681; Hunter C., Shellburn US 3,904,420; Gailis A., Kolesnikov VA, Silens E .; Latv. PSR Zmat. Akad. Vestis 20 (1978); Nagahama S., Shimada K, Harada T., Koga M .: Japan Kokai 7847, 439.
It has now been found that 2-methylbenzothiazole is condensed with 3,4,5,6-tetrachlorophthalic anhydride at 140-150 ° C in the presence of CH3COOK as a base and provides in one synthetic step an intensely orange, highly insoluble high-yield pigment (about 90%). %).
Pigment in water and in conventional organic solvents such as ethanol, methanol, chloroform, dichloromethane, acetone, acetic acid, does not dissolve, cold in dimethyl sulphoxide, dissolves well in the heat, so that it can crystallize from dimethyl sulphoxide. it is stable, color-fast and sophisticated, especially when it is excluded from the alkaline environment. It can also be used in blends with other color pigments to obtain a suitable shade.
The following example illustrates, but does not limit, the use of the invention. Example 1 To a mixture of 3,4,5,6-tetrachlorophthalic anhydride (0.1 mol) and 2-methylbenzothiazole (0.12 mol) was added remelted potassium acetate (0.01 mol), vigorously stirred and heated to 140-150. ° C for 1 h while removing condensation water. After the reaction is complete with stirring, the reaction mixture is cooled to about 70 ° C and 50 cm 3 of ethanol are added thereto, stirred for 30 minutes, then 30 cm 3 of 5% sodium ethoxide are added and stirring is continued at 25 ° C. 30 ° C 1 h.
The precipitate formed is filtered off with suction, washed with ethanol, water and dried, recrystallized from dimethyl sulfoxide, but even without crystallization, the product is sufficiently pure for further use.
Analysis for 4,5,6,7-tetrachloro-2- (2-benzothiazolyl) -1,3-indanedione, C16H5O2NCUS (M = 417.0), melting point above 360 ° C, up to 365 ° C % N, (DMSO after heating) = 388, 578 nm, calculated: 46.07% C, 1.20% H, 3.35% N, 33.99% Cl; H, 1.55; N, 3.58; Cl, 33.61.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS87107A CS259291B1 (en) | 1987-01-06 | 1987-01-06 | 4,5,6,7-tetrachloro-2- (2-benzothiazolyl) -1,3-indanedione and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS87107A CS259291B1 (en) | 1987-01-06 | 1987-01-06 | 4,5,6,7-tetrachloro-2- (2-benzothiazolyl) -1,3-indanedione and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS10787A1 CS10787A1 (en) | 1988-02-15 |
| CS259291B1 true CS259291B1 (en) | 1988-10-14 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS87107A CS259291B1 (en) | 1987-01-06 | 1987-01-06 | 4,5,6,7-tetrachloro-2- (2-benzothiazolyl) -1,3-indanedione and its preparation |
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| CS (1) | CS259291B1 (en) |
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1987
- 1987-01-06 CS CS87107A patent/CS259291B1/en unknown
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| Publication number | Publication date |
|---|---|
| CS10787A1 (en) | 1988-02-15 |
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