Indigo-derivatives as irreversible color changeable dyes for textile materials and process for dyeing textile materials

Patent metadata

Field	Value
Publication number	US-10246820-B2
Application number	US-201715498580-A
Country	US
Kind code	B2
Filing date	Apr 27, 2017
Priority date	Jun 17, 2016
Publication date	Apr 2, 2019
Grant date	Apr 2, 2019

Abstract

Provided are novel compounds of indigo-derivatives as irreversible color changeable dyes. Also provided are methods for the use of various indigo-derivatives for irreversibly color changeable dyes for textile materials and to novel compounds. Also provided is a process for dyeing textile materials, especially denim, with indigo-irreversible color changeable dyes and for textiles and garment articles made by the dyeing process for textile materials.

First claim

The invention claimed is:

1. A process for dyeing textile materials, said process comprising applying an indigo-derivative of formula (I)

wherein
R 1 , R 2 , R 3 and R 4 each represent a hydrogen atom or a halogen atom, provided that R 1 , R 2 , R 3 and R 4 are not all hydrogen atoms and
R 5 and R 6 each represent a hydrogen atom or a tert-butoxycarbonyl group, provided that R 5 and R 6 are not both hydrogen,

onto a textile material.

2. The process according to claim 1 , wherein said process is an irreversible color changeable dyeing process.

3. The process according to claim 1 , wherein each of said R 1 , R 2 , R 3 and R 4 comprises a halogen atom.

4. The process according to claim 3 , wherein each said halogen atom comprises a bromine atom.

5. The process according to claim 1 , wherein one of said R 5 and said R 6 is a hydrogen atom and the other of said R 5 and said R 6 comprises a tert-butoxycarbonyl group.

6. The process according to claim 1 , wherein said textile material is denim.

7. The process according to claim 1 , wherein said textile material comprises cotton, wool, linen, viscose, or a mixture thereof.

8. The process according to claim 1 , further comprising subsequently processing said textile material with one or more external stimuli, to configure a surface of said textile material.

9. The process according to claim 8 , wherein said textile material comprises one of cotton, wool, linen, viscose and a mixture thereof.

10. The process according to claim 8 , wherein said textile material is denim.

11. The process of claim 1 , further comprising, after said applying, forming said textile material into a garment article then processing said garment article with one or more external stimuli, in order to configure a surface of said garment article.

12. An indigo-derivative of formula (I)

wherein each of said R 1 , R 2 , R 3 and R 4 comprises a halogen atom and R 5 and R 6 are, each independently, a hydrogen atom or a tert-butoxycarbonyl group (t-BOC), provided that R 5 and R 6 are not both hydrogen.

13. The indigo-derivative according to claim 12 , wherein each of said R 1 , R 2 , R 3 and R 4 comprises a bromine atom and formula (I) comprises formula (II)

14. Indigo-derivatives of formula (I)

wherein each of said R 1 , R 2 , R 3 and R 4 comprises a hydrogen atom, one of said R 5 and said R 6 is a hydrogen atom and the other of said R 5 and said R 6 comprises a tert-butoxycarbonyl group.

15. A textile material dyed according to the process of claim 1 .

16. A textile material formed according to the process of claim 8 .

17. A garment article dyed according to the process of claim 1 .

18. A garment article formed according to the process of claim 8 .

19. The process according to claim 1 , wherein two of R 1 , R 2 , R 3 and R 4 are a hydrogen atom and the other two are a halogen atom.

20. The process according to claim 1 , wherein R 1 and R 4 are a hydrogen atom and R 2 and R 3 are a halogen atom.

21. The process according to claim 1 , wherein R 1 and R 4 are a halogen atom and R 2 and R 3 are a hydrogen atom.

22. The process according to claim 1 , wherein R 1 , R 2 , R 3 and R 4 are each a chlorine atom.

Assignees

• Sanko Tekstil Isletmeleri San Ve Tic As

Inventors

• Kaplan Gokhan
• Akdemir Ozgur
• Cobanoglu Ozgur

Classifications

• D06P1/228 Primary

  Indigo · CPC title

• D06P3/6025

  using vat or sulfur dyes · CPC title

• C09B7/04 Primary

  Halogenation thereof · CPC title

• D06M10/005

  Laser beam treatment · CPC title

• D06P5/2005

  Treatments with alpha, beta, gamma or other rays, e.g. stimulated rays · CPC title