Bis-indolylmethanes, a process for their preparation and uses thereof

Patent metadata

Field	Value
Publication number	US-10081596-B2
Application number	US-201615284670-A
Country	US
Kind code	B2
Filing date	Oct 4, 2016
Priority date	Oct 5, 2015
Publication date	Sep 25, 2018
Grant date	Sep 25, 2018

Abstract

The present invention relates to novel bis-indolylmethanes, a process for their preparation and their use in the preparation of technical textiles and PPE's (Personal Protective Equipments), namely in the preparation of UV-protective and anti-infective textiles and garments.

First claim

What is claimed is:

1. A compound of formula (I)

wherein:
R 1 is selected from the group consisting of hydrogen, a halogen atom, a non-substituted, saturated or unsaturated, linear or branched, acyclic C1-C10 alkyl group; and a non-substituted, saturated or unsaturated, linear or branched, acyclic C1-C10 alkoxy group; when R 2 and R 3 are H;
R 2 is selected from the group consisting of hydrogen, a non-substituted, saturated or unsaturated, linear or branched, acyclic C1-C10 alkyl group, and a non-substituted, saturated or unsaturated, linear or branched, acyclic C1-C10 alkoxy group; when R 1 is H and R 3 are alkyl or alkoxy groups as above defined;
R 3 is selected from the group consisting of hydrogen, a halogen atom, a non-substituted, saturated or unsaturated, linear or branched, acyclic C1-C10 alkyl group, and a non-substituted, saturated or unsaturated, linear or branched, acyclic C1-C10 alkoxy group; when R 1 is H and R 3 are halogen, alkyl or alkoxy as above defined;
R 4 is selected from the group consisting of a non-substituted, saturated or unsaturated, linear or branched, acyclic C1-C10 alkyl group, and a non-substituted, saturated or unsaturated, linear or branched, acyclic C1-C10 alkoxy group;
R 5 is selected from a halogen atom; polyvinylalcohol; polyvinylamine and a cellulose-polymer;
R 6 is selected from the group consisting of a halogen atom; polyvinylalcohol;
polyvinylamine and a cellulose-polymer; and
m is from 3 to 5.

2. The compound according to claim 1 , wherein said R 2 is hydrogen; said R 1 and said R 3 are both chlorine; said R 4 and said R 5 are both methyl groups; said R 5 and said R 6 are both bromine and m is 4.

3. The compound according to claim 1 , wherein said R 1 is hydrogen; said R 2 and said R 3 are both a methoxy group; each said R 4 is a methyl group; said R 5 and said R 6 are both bromine and m is 4.

4. The compound according to claim 1 , wherein said R 1 is fluorine; said R 2 and said R 3 are both hydrogen; each said R 4 is a methyl group; said R 5 and said R 6 are both bromine and m is 4.

5. The compound according to claim 1 , wherein said R 2 is hydrogen; said R 1 and said R 1 are both chlorine; said R 4 s are methyl groups; said R 5 is bromine and said R 6 is polyvinylalcol and m is 4.

6. The compound according to claim 1 , wherein said R 1 is hydrogen; said R 2 and said R 3 are both a methoxy group; each said R 4 is a methyl group; said R 5 is bromine and said R 6 is polyvinylalcol and m is 4.

7. The compound according to claim 1 , wherein said R 1 is fluorine; said R 2 and said R 3 are both hydrogen; each said R 4 is a methyl group; said R 5 is bromine and said R 6 is polyvinylalcol and m is 4.

8. The compound according to claim 1 , wherein said PVA molecular weight is approx. 100,000-130,000 g/mol with a Pw: 2,700 (polymerisation degree) and hydrolysis ratio: 86-88%.

9. A method to make fabrics that are sun-protective and anti-infective fabrics, said method comprising treating said fabrics with at least a compound according to claim 1 .

10. A fabric comprising clothing or a Personal Protective Equipment (PPE) treated with at least one compound according to claim 1 .

11. A process for the preparation of a compound according to claim 1 , the process comprising reacting compounds of formula (II) and (Ill) according to the following scheme

12. The process of claim 11 , wherein, in said step a, a compound of formula (II) is reacted with a compound of formula (III) in an appropriate solvent, in the presence of a strong base, the molar ratio compound (II)/compound (III)/base being about 1/4/2.

13. The process of claim 11 , wherein, in step b, a compound of formula (IV) is reacted with benzaldehyde of formula (V), in a molar ratio of at least 2/1, in the presence of catalytic amounts of 1,3-dibromo-5,5-dimethylhidantoin (DBDMH), without the presence of any solvent.

14. The process of claim 11 , wherein, in step c, a compound (VI) is reacted with a reactant selected from the group consisting of polyvinylalcohol; polyvinylamine and a cellulose-polymer, in a suitable solvent and in the presence of a base.

15. The process of claim 11 , wherein said Hal is bromine, and said R 4 is methyl.

16. The process of claim 11 , wherein said R 5 is bromine and said R 6 is polyvinylalcohol (PVA).

17. The method according to claim 9 , wherein said fabrics are cotton fabrics.

18. The method according to claim 9 , wherein said fabrics are denim fabrics.

Assignees

• Sanko Tekstil Isletmeleri San Ve Tic As
• Sanko Tekstil Isletmeleri San Ve Tic As

Inventors

• Aker Acelya
• OCAL Nuket
• ERGINDEMIR Hikmet Nil
• Hamitbeyli Agamirze

Classifications

• C07D209/10

  with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring · CPC title

• D06M2200/00

  Functionality of the treatment composition and/or properties imparted to the textile material · CPC title

• A41D2400/26

  UV light protection · CPC title

• D06M2200/25

  Resistance to light or sun, i.e. protection of the textile itself as well as UV shielding materials or treatment compositions therefor; Anti-yellowing treatments · CPC title

• C07D209/12 Primary

  Radicals substituted by oxygen atoms · CPC title