FR2652585A1 - PIGMENTARY COLORANTS. - Google Patents

Abstract

Pigment dyes of formula I (CF DRAWING IN BOPI) in which F represents the residue of a metal-free dye with 1 to 4 acid groups, A a compound having 1 to 4 residues with sterically hindered nitrogen atoms, among which at least n ammonium nitrogen atoms n is 1 or 2

Description

The subject of the invention is salts of acidic dyes with compounds

  containing at least one residue with a sterically hindered amine, largely insoluble

  in organic compounds. These compounds are suitable

  iably as pigments for coloring syn-

thetics with and without solvents.

  The new pigments correspond to the formula I Fn. A (I) wherein F is the residue of a metal-free dye with 1 to 4 acid groups, A a compound having 1 to 4 residues with sterically hindered nitrogen atoms, of which at least n are nitrogen atoms ammonium

and n is 1 or 2.

  The pigments according to the invention are suitable

  for PVC, for all polyolefins (eg polyethylene)

  high and low pressure, polypropylene), polyiso-

  butylene, poly-4-methylpentene and copolymers obtained from these synthetic materials. They can also be used for the coloration of polystyrene (and its copolymers>, ABS, polyvinyl acetate), poly

  (polyvinyl alcohol), polyacetate, polyacrylates,

  lyacrylonitrile, polyacrylamide, polyvinyl chloride,

  lidene), polyesters, polyethers (POMs), polythers

  ethers and thioplasts, polycarbonates, polyurethane,

  derivatives of cellulose, maleic resins, pheno-

  melamine, aniline, furan resins, carbamidic, epoxy and silicone resins, as well as for the pigmentation of varnishes and printing inks for

the graphic industry.

  As dyes F, non-metallized azo dyes containing acidic groups are preferred, but other acid dyes of different constitution may

  find a use, for example phthalate dyes

  cyanines, anthraquinones, perylene dyes,

  indigo dyes, thioindigoides, dyes of the

  rinone, quinacridone, dioxazine dyes,

  dyes of isoindoline, isoindolinone, colourants

  Diketopyrrolo-pyrroleic agents, in particular phthalocyanine, indigo, anthraquinone, dioxazinic dyes

  and the dyes of isoindolinone.

  Examples of very suitable dye components F correspond to the formulas F.O. R Ci C! C o CE E3 Ci Cl C 03.s3 coeB I

% CONE00

3 6% 5

  S5050 E, 3C / n 3yjS0 i / i Key 65-N-C Sa3 Ci Ci y = N / \ N = Ca P: i ii24! D CR3Ci so. e; ocE3 C! J Ci

--N '--- AF- 3E

FllACOOg'F2 [tIIIiIIfO

'S-N = N

  ECEF3ci COQ CaRo Ci Coo 2. C * / k - Fis E..C6-k - 3 E 6II h He N. CE,

o -

C 2; O NE, o NE, 1- so - soo

N. 3 'N., 3

  Fi, A * CH3, Fia N "'bU / \ CH3 o J / \ NEcO-C6H5

O NE CH ..,

  He is so-so. 3 ... 1 d F20 JI

H NHCOCC1CH2 'N.

O bU 3 / \ CH3 Q -

- 4 /

HC O O NE

12

  f - 'SO F21 * N. i N. O - C2H5 o .. / \ NEcoc3 O NE2 e

so j-

-. N. 3, F24

N. - "EC Br N. -

O "CE3 O bU CE

- 3

  CU 3r F25 ,, F26 Br 0,% qI-C 0 O 0 -, 0 5 -C00e

0 NE, C0

O kaO

N 0

  o N0 * Br N 0e a0; o oo y. ,, e0 3 / S NEOC HO CON / - \ Oc

CE3 (F

- \ T.

  (Rg) F32 O or R9 = Chlorine, bromine, C1-C3 alkyl or C1-C4 alkoxy CONE S0 and m = 1, 2 or 3 Cl SO9 i HI COON F33 D 3 F34 -s 09 F3s 2 S038

0 3 3

EN-C

- NOT

Q0

0 31CK

"30

  N, F32 oQ R9 = Chlorine, bromine, alkylNH in

7 LC T = III

## EQU1 ##

1-1 1-4

  OIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIO

O '"' '- \ N N O

  c g OS o OS r g ú I i -S O r eOS-jli - e t SOg LdN

ID O 9

98999

  Monoazoic dyes with an acid group

  sulfonic acid are particularly preferred.

  Particularly preferred pigments according to the invention contain in component A one, two, three or four radicals of formula a 'CE3 RI S'N'-' 3 (a '), CH3

  wherein R11 is hydrogen or methyl.

  Particular preference is also given to pigment dyes in which component A (as free amine) is a compound of formula f, g or h R MIi (g)

I C05-R3) R3

  Wherein R3 is 2,2,6,6-tetramethylpiperidyl44, R8 is chlorine or 2,2,6,6-tetramethylpiperidyl-4-amino and n is 1, 2, 3 or 4, whereby two of the substituents - (CO-NHR3) in the formula f are in the meta or para position and, when n = 3 or 4, more than two of these substituents

  shall not be in a vicinal position, one

port to another.

  Preferred radicals having a steroid amino group

  In other words, the following formulas are defined: ## EQU1 ##

R 12 MR

R. / s <A Ca),)

_2 R, 2.12

  12! 2; Wherein R 11 is hydrogen or C 1 -C 4 alkyl, preferably hydrogen or methyl, especially hydrogen, all R 12 are C 1 -C 5 alkyl, preferably a methyl,

  the two R13s represent, independently, the hydro-

  gene, a C1 to C2 alkyl, an R13 also represents a

  nyl or both R1 together a group of formula - (Ca2) 11- and

  Y a group of formula -N-CO- or -CO-N-

  Particularly preferred components A (in the form of a free amino compound) are, for example:

  A triamide of 1,3,5-tri- (2 ', 2', 6 ', 6'-tetramethyl-

péridyl-4 ') - trimesic,

  A2 2,4-bis (2 ', 2', 6 ', 6'-tetramethylpiperidyl-4'-amino) -6-chloro

rotriazine,

  A3 2,4,6-tri (2 ', 2', 6 ', 6'-tetramethylpiperidyl-4'amino) -

triazine

  A4 bis- (2 ', 2', 6 ', 6'-tetramethylpiperidyl-4'-aminocarbonyl)

  paraphenylene) terephthalamide, A5 bis- (2 ', 2', 6 ', 6'-tetramethylpiperidyl4') terephthalamide,

  A6 2,4-bis- (2 ', 2', 6 ', 6'-tetramethylpiperidyl-4-amino) -qui

nazoline,

  A7 2,3-bis (2 ', 2', 6 ', 6'-tetramethylpiperidyl-4'amino) -quinoline

xaline,

  A8 1,4-bis (2,2 ', 6', 6'-tetramethylpiperidyl-4'-amino) -phthalate

lazine,

  A9 2-chloro-4,6-bis- (2 ', 2', 6 ', 6'-tetramethylpiperidyl-4'-

amino) -pyrimidine,

  A10 2,5-dichloro-4,6-bis- (2 ', 2', 61,6'-tetramethylpiperidyl)

4'-amino) -pyrimidine,

  All 2-fluoro-5-chloro-4,6-bis- (2 ', 2', 6 ', 6-tetramethylpiperamine)

ridyl-4'-amino) -pyrimidine, A12