DE1913614A1 - Process for coloring synthetic polymers - Google Patents

Description

19136H

FARBWERKE HOECHST AG. formerly Master Lucius & Brüning

File number: Fw 6030

Date: March 11, 1969

Dr.B / Blt.

Process for coloring synthetic polymers

It has been found that dyes of the general formula

where R is an alkyl radical with 8-20 carbon atoms and R ₁ and Rn are hydrogen or halogen atoms, alkyl, alkoxy or carbalkog groups, especially suitable for coloring water-soluble, thermoplastic synthetic polymers in bulk.

The main synthetic polymers are polystyrene, Polymethacrylate and plasticizer-free polyvinyl chloride into consideration.

The dyes mentioned are distinguished by high color strength and, in particular, by very good thermal stability. They are therefore einsetzbax for refractory polystyrene brands * that are processed at temperatures up to ⁰ C 3QO, your effective solution behavior leads both polystyrene and polymethacrylate and in weichmaeherfreieni poly-

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vinyl chloride to a rapid homogeneous coloring and one obtains brilliant yellow, intensely yellow-green fluorescent transparent dyeings of very good lightfastness, which are retained even when lightened with white pignient Surprisingly, they are particularly notable for the good solubility of these dyes in organic solvents in plasticizer-free polyvinyl chloride, by a excellent migration fastness.

The dyes are used in the materials to be colored in the usual way, for example by kneading at higher Temperature, colored. The dye content of the process colored polymers depends on the desired depth of color. Generally there will be amounts of dye between about 0.02 and 5%, based on the weight of the material to be colored, used.

The dyes of the above formula used in accordance with the process can be prepared according to the British patent 1,095,784 processes described can be obtained by converting the diazonium salts of compounds of the formula

where R * and R _{2 have} the meanings given above, X- is a hydrogen atom and X _{0 is} an amino group or X _{1 is} an amino group and X "is a hydrogen atom, and Y is the group> N - R, where H is the above Has the meaning ", or represents an oxygen atom, in the present" from lupf er or copper aisen and, if Y

009840/204%

- 3 - Fw 6 (330

represents an oxygen atom, the compounds thus obtained with compounds of the formula

"R-HH ₈

in which R has the meaning given above, condensed. Examples of suitable amines of the above formula are octyl-, dodecyl-, hexadecyl- and, preferably, stearylamine.

example 1

100 parts by weight of plasticizer-free polyvinyl chloride as Suspension polymer are on a two-roll mixer at a Yialzent temperature of 170 C and one Friction of 1: 1.2 plastically softened / calibrated. Afterward 0.5 part by weight of titanium dioxide and 0.1 part by weight of benzothiojranthen-3, 4-dicarboxylic acid-N-stearylimide added, rolled for 10 minutes, the polyvinyl chloride mass on a; Heheizbax * en calender given and at 170 C films of 1 ram thickness peeled off. Yellow-colored films with excellent migration and lightfastness are obtained.

Instead of benzothioxantben-3, 4-dicarboic acid-K-stearylimide can with the same success also .8-methyl-, 9,10-dimethyl-, " 10-Kethyl-, 9-methoxy-, 8,10-dichloro- or 9-Methyl-10-chlQrbenzotIn.oxanthene-3, 4-dicarboxylic acid-it ™ stearylimide or --Ii-dodecylimide uses v / crden.

009840/2043

Fw 6030

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Example 2

100 parts by weight of non-modified polystyrene granules with a melt index E5 of 1.56 at 200 ° C. are dry mixed with 0.1 part by weight of benzothioxanthene-3,4-dicarboxylic acid-N-octylimide. The mixture is poured into a screw-injection molding machine at 220 ° - 300 ⁰ C sprayed. This gives bright yellow, k intensely yellow-green fluorescent, transparent injection molded parts of high lightfastness and bleeding resistance.

Example 3

A commercial Polymethacrylatgranulat is mixed with 0.05 Ge \ Vicht percent lO-Methoxybenzothioxanthen-3, 4-dicarboxylic ^acid-N-r hexadec5 lir> iid dry and sprayed in a screw injection molding machine at 220 C. The strong yellow-green fluorescent, bright yellow colored, transparent injection molded parts have very good fastness properties.

QQ98A0 / 2CU3

Claims (2)

- 5 - Fw 6030 patent claims 1) Process for coloring water-insoluble thermoplastic synthetic polymers in the Composition, characterized in that these materials are mixed with benzothioxanthendicarboximide dyes the general formula 0
R, where R is an alkyl radical with 8-20 carbon atoms and R and R _{2 are} hydrogen or halogen atoms, alkyl, alkoxy or carbalkoxy groups, colors in the mass. 2) Those with benzothioxanthendicarboxylic acid dyes the general formula where R is an alkyl radical having _{8-20 carbon atoms and R 1} and R are hydrogen or halogen atoms, alkyl, alkoxy or carbalkaxy groups, water-insoluble, thermo-elastic synthetic polymers which are colored in the mass. . _{; <} c 009840/2043