Process for colouring a thermoplastic polymer

Patent metadata

Field	Value
Publication number	US-12448520-B2
Application number	US-202118001066-A
Country	US
Kind code	B2
Filing date	Jun 9, 2021
Priority date	Jun 10, 2020
Publication date	Oct 21, 2025
Grant date	Oct 21, 2025

Abstract

A process can be used for manufacturing a coloured moulding composition with an improved optical appearance and a particularly high thermal stability. The process involves providing a thermoplastic polymer and adding a colouring preparation, or a liquid composition or a master batch containing the colouring preparation. Injection moulded parts and extruded parts can be composed of the coloured moulding composition.

First claim

The invention claimed is:

1. A process for manufacturing a coloured moulding composition, the process comprising:
a) providing a thermoplastic polymer; and
b) adding to the thermoplastic polymer from a), a colouring preparation or a liquid composition or a masterbatch comprising said colouring preparation,
wherein the colouring preparation comprises a monoazo dye comprising at least one heteroaromatic moiety; and
wherein the colouring preparation comprises
less than 100 ppm of aluminium or a compound thereof, and
less than 300 ppm of silicon or a compound thereof; and
wherein the colouring preparation has mass loss in dried form of 0.0 to 5.0 wt. % in isothermal thermogravimetric analysis at 260° C. for 15 min.

2. The process according to claim 1 , wherein the liquid composition added in b) comprises, based on a weight of the liquid composition:
from 1.0 to 30.0 wt.-% of a dispersing additive,
from 0.5 to 50.0 wt.-% of the monoazo dye,
from 0.0 to 50.0 wt.-% of auxiliary additives, and
liquid,
wherein portions by weight of components of the liquid composition add up to 100 wt.-%.

3. The process according to claim 1 , wherein the masterbatch added in b) comprises, based on a weight of the masterbatch:
from 0.01 to 50.0 wt.-% of the monoazo dye,
from 50.0 to 99.99 wt.-% of the thermoplastic polymer,
from 0.0 to 10.0 wt.-% of auxiliary additives, and
from 0.0 to 10.0 wt.-% of further colourants,
wherein portions by weight of components of the masterbatch add up to 100 wt.-%.

4. The process according to claim 1 , wherein the monoazo dye is at least one selected from the group consisting of
5-[(3,4-dichlorophenyl) azo]-1,2-dihydro-6-hydroxy-1,4-dimethyl-2-oxonicotinonitrile,
2,3-dihydro-2,2-dimethyl-6-((4-(phenylazo)-1-naphthyl)azo)-1H-perimidin,
cyano-S-[[5-cyano-2,6-bis[(3-methoxypropyl)amino]-4-methylpyridin-3-yl]azo]-3-methyl-2-thiophenecarboxylic acid methyl ester,
5-methyl-2-phenyl-4-phenylazo-4H-pyrazol-3-one,
4-[(2,4-dimethylphenyl) azo]-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one,
3-[(1-oxonaphthalen-2-ylidene)methylhydrazinylidene]-1-prop-2-enylindol-2-one,
4-((o-methoxyphenyl)azo)-3-methyl-1-phenyl-2-pyrazolin-5-one, and
5-methyl-2-phenyl-4-phenylazo-4H-pyrazol-3-one.

5. The process according to claim 1 , wherein the thermoplastic polymer is selected from the group consisting of polyalkyl (meth)acrylate, polymethylmethacrylimide, polymethyl methacrylate copolymer, polystyrene, polystyrene copolymer, acrylonitrile copolymer, polycarbonate, polyester, polyamide, polyvinylidene fluoride, and a mixture thereof.

6. The process according to claim 1 , wherein the thermoplastic polymer comprises a polymer matrix and scattering particles dispersed in said polymer matrix,
wherein the scattering particles have a weight average particle diameter of from 0.01 μm to 100.0 μm, and a refractive index of the scattering particles differs from that of the polymer matrix by at least 0.01.

7. The process according to claim 1 , wherein the thermoplastic polymer comprises at least one impact modifier selected from the group consisting of particulate impact modifier and thermoplastic impact modifier.

8. The process according to claim 1 , wherein the colouring preparation has a mass loss in dried form of from 0.01 to 4.0 wt. %, in isothermal thermogravimetric analysis at 260° C. for 15 min.

9. The process according to claim 1 , wherein b) is carried out in an extruder.

10. The process according to claim 1 , wherein the thermoplastic polymer is polymethyl methacrylate having a weight average molecular weight Mw of from 80,000 g/mol to 180,000 g/mol and is obtainable by polymerization of a polymerizable composition whose polymerizable constituents comprise, based on a weight of the polymerizable composition:
(i) from 50.0 to 99.9 wt.-% of methyl methacrylate,
(ii) from 0.1 to 50.0 wt.-% of an acrylic acid ester of a C 1 -C 4 alcohol, and
(iii) from 0.0 to 30.0 wt.-% of at least one further monomer copolymerizable with monomers (i) and (ii).

11. The process according to claim 1 , wherein the masterbatch or the liquid composition added in b) further comprises
at least one further dye selected from the group consisting of perinone dye, quinophthalone dye, and anthraquinone dye;
at least one inorganic pigment;
at least one phthalocyanine pigment; or
any mixture of the above.

12. A coloured moulding composition, comprising a thermoplastic polymer and a monoazo dye, wherein the coloured moulding composition is obtainable by the process according to claim 1 .

13. The coloured moulding composition according to claim 12 , comprising:
less than 100 ppm of aluminium or a compound thereof, and
less than 300 ppm of silicon or a compound thereof.

14. The coloured moulding composition according to claim 12 , wherein the coloured moulding composition has a melt flow rate from 0.5 to 10.0 g/10 min, measured at 230° C. with a load of 3.8 kg.

15. A process for the manufacturing of a moulded part, the process comprising:
injection moulding the coloured moulding composition according to claim 12 at a temperature ranging from 200° C. to 320° C., into a mould which can produce the moulded part,
wherein the coloured moulding composition comprises the monoazo dye comprising at least one heteroaromatic moiety, and
wherein the coloured moulding composition comprises
less than 100 ppm of aluminium or a compound thereof, and
less than 300 ppm of silicon or a compound thereof.

16. A process for the manufacturing of an extruded part, the process comprising:
extruding the coloured moulding composition according to claim 12 at a temperature ranging from 200° C. to 320° C., wherein the coloured moulding composition is melted and die-casted to the extruded part,
wherein the coloured moulding composition comprises the monoazo dye comprising at least one heteroaromatic moiety, and
wherein the coloured moulding composition comprises
less than 100 ppm of aluminium or a compound thereof, and
less than 300 ppm of silicon or a compound thereof.

17. The process according to claim 15 , wherein the moulded part has different wall thicknesses, one or more perforations, at least one non-planar surface, or a combination of these features.

18. A moulded part, obtainable by the process according to claim 15 .

19. An extruded part, obtainable by the process according to claim 16 .

20. The process according to claim 1 , wherein the colouring preparation comprises less than 50 ppm of aluminium or a compound thereof, and less than 200 ppm of silicon or a compound thereof.

Assignees

• Roehm Gmbh

Inventors

• Golchert Ursula
• Richter Ralf
• Kraft Jörg
• Dietrich Gerald
• Becker Ernst
• Nau Stefan

Classifications

• C09B67/0041

  mixtures containing one azo dye · CPC title

• C09B39/00

  Other azo dyes prepared by diazotising and coupling · CPC title

• C08K5/45

  Heterocyclic compounds having sulfur in the ring · CPC title

• C08J2333/12

  Homopolymers or copolymers of methyl methacrylate · CPC title

• C08J3/226

  using a polymer as a carrier · CPC title