Substituted benzotriazole phenols

Patent metadata

Field	Value
Publication number	US-10919867-B2
Application number	US-201615741647-A
Country	US
Kind code	B2
Filing date	Jun 30, 2016
Priority date	Jul 7, 2015
Publication date	Feb 16, 2021
Grant date	Feb 16, 2021

Abstract

Benzotriazole phenols with substituents either ortho to the phenol hydroxyl group and/or para to the phenol hydroxyl group can be prepared from the unsubstituted benzotriazole phenol by coupling reactions. The ortho substituent group can be a simple alkoxy or amino group, or the ortho substituent group can be a linking group, linking the benzotriazole phenol to another benzotriazole phenol group.

First claim

What is claimed is:

1. A composition comprising a substituted benzotriazole phenol with the structure of Formula I:

wherein if R 1 is an —O—R 9 , a —N—R 9 R 10 , a —B(OR 18 )(OR 19 ) group, or a —SiR 20 3 group wherein R 9 is selected from an alkyl group, or an aryl group, and R 10 is selected from a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, or a heteroatom-containing group comprising one or more oxygen, nitrogen, sulfur, or phosphorous atoms, or R 9 and R 10 together with the atoms connecting form a heterocyclic ring structure, each R 18 and R 19 is independently a hydrogen atom, an alkyl group, an aryl group, or R 18 and R 19 together with the atoms connecting form a heterocyclic ring structure, each R 20 group is an alkyl group; and
each R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 , independently is a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, or a halogen atom; and R 3 is an alkyl group with 8 carbon atoms.

2. The composition of claim 1 , wherein R 1 comprises an —O—R 9 group wherein R 9
an alkyl group with 1-20 carbon atoms; or
an aryl group.

3. The composition of claim 2 , wherein R 9 is:
an alkyl group with 1-6 carbon atoms; or
an aryl group comprising a substituted phenyl group.

4. The composition of claim 1 , wherein R 1 comprises a —N—R 9 R 10 group:
wherein R 9 is selected from an alkyl group with 1-20 carbon atoms; or
an aryl group;
R 10 is selected from a hydrogen atom or an alkyl group with 1-6 carbon atoms.

5. The composition of claim 4 , wherein R 9 is selected from:
an alkyl group with 1-6 carbon atoms; or
an aryl group comprising a 3-alkyl substituted phenyl group, wherein the alkyl substituted group has 1-6 carbon atoms;
R 10 is a hydrogen atom.

6. The composition of claim 1 , wherein R 1 comprises a hydrogen atom; R 3 is an alkoxy group comprising 4 carbon atoms; and each R 2 , R 4 , R 5 , R 6 , R 7 , and R 8 , independently is a hydrogen atom.

7. The composition of claim 2 , wherein R 1 comprises an —O—R 9 group wherein R 9 is an alkyl group with 4 carbon atoms.

8. The composition of claim 2 , wherein R 1 comprises an —O—R 9 group wherein R 9 comprises an aryl group comprising a 3-methyl phenyl group, or a 4-methyl phenyl group.

9. The composition of claim 4 , wherein R 1 comprises an —N—R 9 R 10 group wherein R 9 is an alkyl group with 1 carbon atom, or an alkyl group with 6 carbon atoms;
R 10 is a hydrogen atom.

10. The composition of claim 4 , wherein R 1 comprises an —N—R 9 R 10 group wherein R 9 is an aryl group comprising an alkyl substituted phenyl group, wherein the alkyl substituted group has 1-20 carbon atoms;
R 10 is a hydrogen atom.

11. The composition of claim 10 , wherein the alkyl substituted phenyl group is a 4-hexyl phenyl group.

12. The composition of claim 1 , comprising the structure of Formula II:

wherein X comprises an —O—, —NR 10 —, —S(O)—, —S(O) 2 —, or —S— linking group where R 10 is selected from a hydrogen atom, an alkyl group, or an aryl group,
each R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , and R 17 , independently independently is a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, or a halogen atom; and
R 3 and R 16 are each an alkyl group with 8 carbon atoms.

13. The composition of claim 12 , wherein X is an —NR 10 — linking group where R 10 is selected from a hydrogen atom, an alkyl group comprising 1-3 carbon atoms.
R 3 and R 16 , each comprises an alkyl group with 1-20 carbon.

14. The composition of claim 12 , wherein X comprises an —O— linking group.

15. The composition of claim 12 , wherein X comprises an —NR 10 — linking group where R 10 is a hydrogen atom; and each R 2 , R 4 , R 5 , R 6 , R 7 , R 8 , R 11 , R 12 , R 13 , R 14 , R 15 , and R 17 , independently is selected from a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, or a halogen atom.

16. The composition of claim 12 , wherein X comprises an —NR 10 — linking group where R 10 is a methyl group; and each R 2 , R 4 , R 5 , R 6 , R 7 , R 8 , R 11 , R 12 , R 13 , R 14 , R 15 , and R 17 , independently is selected from a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, or a halogen atom.

17. The composition of claim 12 , wherein X comprises an —O— linking group; and each R 2 , R 4 , R 5 , R 6 , R 7 , R 8 , R 11 , R 12 , R 13 , R 14 , R 15 , and R 17 , independently is selected from a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, or a halogen atom.

Assignees

• 3M Innovative Properties Co

Inventors

• Volp Kelly A
• Schultz Nathan E
• Li Fuming B

Classifications

• C07D249/20 Primary

  with aryl radicals directly attached in position 2 · CPC title

• C07B45/06

  of mercapto or sulfide groups · CPC title

• C07B43/04

  of amino groups · CPC title

• C07D403/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07B51/00

  Introduction of protecting groups or activating groups, not provided for in the preceding groups · CPC title