DD296294A5 - PROCESS FOR PREPARING DISAZOPIGMENTS (9) - Google Patents

Abstract

The invention relates to a process for the preparation of Disazopigmenten (9) of the general formula by azo coupling of diazotized Dialkoxysulfanilsaeureanilid, Alkoxyaminobenzanilid to Aminomonofarbstoff and after renewed diazotization and azo coupling to violet, blue and especially black pigments for camouflage and disguise colors in paints, printing inks, plastics and as a toner in electrophotography. Formula {azo pigment; disazo; Dialkoxysulfanilsaeureanilid; Alkoxyaminobenzanilid; cresidine; Aminohydrochinondimethylaether; b-naphthol; 2,3-hydroxynaphthoic acid; 2,3-Oxynaphthoesaeurearylide; azo coupling; Paint pigment; Pigment inks}

Description

For this 2 pages drawings

Field of application of the invention

The invention enables the synthesis of disazo pigments which can be used in paints, printing inks, plastics, elastomers, in particular as camouflage dyes for camouflage and illusion colors and as toners in electrophotography.

Characteristic of the known state of the art

Some inventions are known which describe sulfamide- or carbamide-bearing anilines as diazotization components. In the case of the known disazo pigments, these are always primary disazo pigments or ice colors of the naphthol AS series.

Object of the invention

It is an object of the invention to produce novel azo pigments which can preferably be used in camouflage pigment mixtures.

Explanation of the essence of the invention

a) Technical task

The object is to use known diazo components in monoazo pigments for the preparation of novel secondary disazo pigments.

b) Features of the invention

According to the invention, the amines of the general formula

with R = -OCH ₃ , -OC ₂ H ₅

R ₁ = -SO ₂ NHCH ₃ , -SO ₂ NHC ₂ H ₆ , -SO ₂ NHphenyl

and R ₂ = -OCH ₃₁ -OC ₂ H ₅

or R ₁ = dog

R ₂ = CONH ₂ , -CONHalkyKC, - ,,), CONHphenyl

as diazo component with serving as coupling components primary aromatic amines of the general formula

^ mH Rj = -CH ₃ , - (

coupled to Aminomonoazofarbstoff.

The latter is again diazotized and with coupling components of the general formula

A ₆ -H ₁ alkyl (C _1-

R ₄ = -H, -COOH, with R ₅ --H ₁ -Br, -OCH ₅₁

, -napkilnyl

R ₇ , R ₈ , R ₉ = -H, -CH ₃ , -OCH ₃ , -OC ₂ H ₆ , -Cl, -CONH ₂ , -CONH-alkyl (C ₁ ^), - NHCOCH ₃ , -CONH- phenyl, -SO ₂ NH-phenyl R ₁₀ = -H, -CH ₃ , -OCH ₃ , -OC ₂ H ₅ , -Cl

in aqueous medium at pH 3-9 and temperatures between ± 0 ⁰ C and + 60 ⁰ C, possibly in the presence of surfactants to the secondary disazo pigments of the general formula according to the invention

wherein Ri to R _{5 have} the meaning given above reacted.

With possibly proportional use of water-soluble and / or water-insoluble organic solvents during the final coupling can be achieved by the thereby achieved improvement in the crystallization of a significant increase in light fastness and migration fastness.

The resulting new secondary disazo pigments are usually obtained as a grain-soft black powder, the z. B. can be easily distributed in soft PVC or chlorinated rubber. They give violet, bluish or deep black colorations.

Exemplary embodiments

30.8 g of 2,5-dimethoxy-sulfanilsäureanilid are diazotized as usual, then by known methods with

13.7 g of cresidine in the presence of

0.5 g of dispersant BO (VEB Buna-Werke Schkopau) coupled, then again diazotized at + 40 ° C.

27.7 g of 2,3-oxynaphthoic acid 2'-methylanilide be vermäischt with

200ml ethanol and slow

30 ml sodium hydroxide solution (32%) added dropwise. The resulting clear, deep yellow solution is with

200ml of water carefully diluted.

The coupling solution drips simultaneously with the above diazo solution while stirring in 200 ml of water containing 1.0 g of dispersant, maintaining the pH at 9 to 10. After 20 minutes congo is made, then worked up.

example

Diazokomp.

Kuppl.komp.

KUPPL.-Komp.2

nuance

2,5-dimethoxy-

sulfanilsäure-

anilide

2,5-dimethoxy-

sulfanilsäure-

anilide

2,5-dimethoxy-

sulfanilsäure-

anilide

cresidine

cresidine

cresidine

2,3-hydroxynaphthoic acid violettst. black 2,3-oxynaphthoic acid 2'-methylanilide violettst. black 2,3-oxynaphthoic acid 2'-methyl-4-chloroanilide deep purple 2,3-oxynaphthoic acid 4'-methoxyanilide violettst. black 2,3-oxynaphthoic acid 2 ', 4'-dimethoxy-5'-chloroanilide tiefbordo 2,3-oxynaphthoic acid 4'-chloroanilide violet black 2,3-oxynaphthoic acid 2 ', 5'-dimethoxy-4'-chloroanilide corinth

2,5-dimethoxy-

sulfanilsäure-

anilide

2,5-dimethoxy-

sulfanilsäure-

anilide

2,5-dimethoxy-

sulfanilsäure-

anilide

2,5-dimethoxy-

sulfanilsäure-

anilide

2,5-dimethoxy-

sulfanilsäure-

anilide

cresidine

cresidine

cresidine

cresidine

cresidine

2,3-oxynaphthoic acid-2'-methyl-4'-methoxyanilide

brown-red

2,5-dimethoxy-

sulfanilsäure-

anilide

2,5-dimethoxy-

sulfanilsäure-

anilide

2,5-dimethoxy-

sulfanilsäure-

anilide

2,5-dimethoxy-

sulfanilsäure-

anilide

2,5-dimethoxy-

sulfanilsäure-

anilide

2,5-dimethoxy-

sulfanilsäure-

anilide

cresidine

cresidine

cresidine

cresidine

cresidine

cresidine

2,3-oxynaphthoic acid-2 ', 5'-dimethoxy-anilide

corinth

2,3-oxynaphthoic acid-1'-naphthamide violettst. black 2,3-oxynaphthoic acid 4'-ethoxyanilide violet black 2,3-oxynaphthoic acid 2'-methyl-5'-chloroanilide Braunst, black 2,3-oxynaphthoic acid-5'-benzimidazolonamide black 2,3-oxynaphthoic acid 4'-phthalimidoamide violettst. black

Diazokomp. Kuppl.komp.1 KUPPL.-Komp.2 -5- 296 294 example 2,5-dimethoxy- cresidine , 2,3-oxynaphthoic acid-2 '4'- nuance 15 sulfanilsäure- bisacetylamidoanilid black anilide 2,5-dimethoxy- cresidine 2,3-oxynaphthoic acid-3'- 16 sulfanilsäure- carbamoylanilide black anilide 2,5-dimethoxy- cresidine 6-methoxy-2,3-oxynaphthoic acid 17 sulfanilsäure- anilide black anilide 2,5-dimethoxy- cresidine 6-methoxy-2,3-oxynaphthoic acid 18 sulfanilsäure- 2'-methylanilide black anilide 2,5-dimethoxy- cresidine e-Methoxy ^^ - oxynaphthoic acid 19 sulfanilsäure- 2 ', 5'-dimethoxy-4'-chloroanilide black anilide 2,5-dimethoxy- 2,5-diethoxy 6-methoxy-2,3-oxynaphthoic acid 20 sulfanilsäure- aniline 2'-5'-dimethoxy-4'-chloroanilide greenest. anilide black 2,5-dimethoxy- 2,5-diethoxy 2,3-Oxynaphthoe- 21 sulfanilsäure- aniline acid anilide blaust. anilide black 2,5-dimethoxy- cresidine 2,3-Oxynaphthoesäureanilid- 22 sulfanilsäure- 2'-methylanilide black anilide -N-methyl amide 2,5-dimethoxy- cresidine 2,3-Oxynaphthoesäureanilid- 23 sulfanilsäure- 5'-benzimid- black anilide azolonamid -N-methyl amide 2-methoxy cresidine 2,3-hydroxynaphthoic acid 24 aniline-5-carbanilide violet 2-methoxy cresidine 2,3-oxynaphthoic acid black 25 aniline-5-carbanilide 4'-methoxyanilide violettst. 2-methoxy cresidine 2,3-oxynaphthoic acid black 26 aniline-5-carbanilide 2,5'-dimethoxyanilide violettst. 2-methoxy cresidine 2,3-oxynaphthoic acid black 27 aniline-5-carbanilide 1'-naphthamide violettst. black

The pigments of the examples of the table, as indicated in the appendices as curves, show a remission course in the VIS and NIR remission spectrum, which makes their use in retreatants for pigmenting camouflage films as well as stealth and illusion paintings possible in order to reduce the remission of green foliage ( Chlorophyll) to be able to imitate. The curves in the appendices show the characteristic remission curve, as required between 650 and 850 nm. However, these pigments still require special recipe processing if they are to fully fulfill their intended purpose within the tolerance curves.

The remission spectra shown in Appendix 1 and 2 were recorded on films with the spectrograph Beckman DK2 A. To this was added 0.5 wt% pigment in e.g. a CPVC clearcoat and pulled to a film of 400 nm wet film thickness.

Claims (1)

Claim: Process for the preparation of disazo pigments, characterized in that the diazotization component is an amine of the general formula 1? with R = -OCH ₃ , -OC ₂ H ₅ R ₁ = -SO ₂ NHCH ₃ , -SO ₂ NHC ₂ H ₅ , -SO ₂ NHphenyl and R ₂ = -OCH ₃ , -OC ₂ H ₅ or Ri = -Hund R ₂ = -CONH ₂ , -CONHalkyl (C _w ), - CONHphenyl with intermediate components of the general formula With - -OCH ₅₁ - , -CH coupled to Aminomonoazofarbstoff and after renewed diazotization with coupling components of the general formula _Λ,. 'K _n . -H ₁ ' COOH, -CONHR. Urf <a ^ψ t> with R ₅ r -H ₁ -Br, -OCH ₂ , OC ₂ H ₅ -η, R ₇ , R ₈ , R ₉ = -H, -CH ₃ , -OCH ₃ , -OC ₂ H ₅ , -Cl, -CONH ₂ , -NHCOCH ₃ , -CONH-phenyl, CONH-alkyl (C ₁ ^) Rio = -H, -CH ₃ , -OCH ₃ , -OC ₂ H ₅ , -Cl to disazo pigments of the general formula OU wherein R ₁ to R _{5 have} the abovementioned meaning, in an aqueous medium at pH 3-10 and temperatures between ± O ⁰ C and + 60 ⁰ C, possibly in the presence of surfactants and / or organic solvents are reacted.