Polytriazole copolymer compositions

Patent metadata

Field	Value
Publication number	US-11814473-B2
Application number	US-202117140685-A
Country	US
Kind code	B2
Filing date	Jan 4, 2021
Priority date	Jul 17, 2020
Publication date	Nov 14, 2023
Grant date	Nov 14, 2023

Abstract

A polytriazole copolymer may include substituted phenyls, substituted benzyls, or both substituted phenyls and substituted benzyls. The substituted phenyls and the substituted benzyls may be independently substituted with hydrogen, bromo, fluoro, chloro, iodo, hydroxy, methyl, trifluoromethyl, dimethylamino, tert-butyl, carboxyl, triphenylmethyl, tris(4-fluorophenyl)methyl, tris(4-methylphenyl)methyl, (4-hydroxyphenyl)diphenylmethyl, and difluoromethoxy groups. The polytriazole copolymer may have a degree of polymerization from 25 to 250.

First claim

What is claimed is:

1. A polytriazole copolymer having a structure according to formula (I):

where:
R 1 and R 2 are independently selected from —C(CF 3 ) 2 — and —O—;
R 3 and R 4 are independently selected from substituted phenyls according to formula (a) and substituted benzyls according to formula (b):

where:
X 1 , X 2 , X 3 , X 4 , and X 5 are independently selected from hydrogen, bromo, fluoro, chloro, iodo, trifluoromethyl, dimethylamino, tert-butyl, carboxyl, triphenylmethyl, tris(4-fluorophenyl)methyl, tris(4-methylphenyl)methyl, (4-hydroxyphenyl)diphenylmethyl, and difluoromethoxy, provided at least one of X 1 , X 2 , X 3 , X 4 , or X 5 on each R 3 and each R 4 is not hydrogen;
m and n represent monomer mole fractions in the polytriazole copolymer;
0<m<1;
0<n<1;
m+n=1,

provided that when R 1 and R 2 are identical, R 3 and R 4 are not identical,

the polytriazole copolymer having a degree of polymerization from 25 to 250.

2. The polytriazole copolymer of claim 1 , wherein in each R 3 and each R 4 , X 1 , X 2 , X 3 , X 4 , and X 5 are independently selected from the group consisting of hydrogen, bromo, chloro, and fluoro, provided at least one of X 1 , X 2 , X 3 , X 4 , or X 5 on each R 3 and each R 4 is not hydrogen.

3. The polytriazole copolymer of claim 1 , wherein in each R 3 and each R 4 , exactly four of X 1 , X 2 , X 3 , X 4 , and X 5 are hydrogen.

4. The polytriazole copolymer of claim 3 , wherein R 3 and R 4 are independently selected from the group consisting of:
3-(trifluoromethyl)phenyl,
4-bromophenyl,
4-fluorophenyl,
4-tert-butylphenyl,
4-(dimethylamino)phenyl,
4-(triphenylmethyl)phenyl,
4-[tris(4-fluorophenyl)methyl]phenyl,
4-[tris(4-methylphenyl)methyl]phenyl,
4-[(4-hydroxyphenyl)diphenylmethyl]phenyl,
4-(triphenylmethyl)benzyl,
4-[tris(4-fluorophenyl)methyl]benzyl,
4-[tris(4-methylphenyl)methyl]benzyl,
4-[(4-hydroxyphenyl)diphenylmethyl]benzyl,
4-(trifluoromethyl)benzyl,
4-fluorobenzyl, and
4-carboxybenzyl.

5. The polytriazole copolymer of claim 3 , wherein R 3 and R 4 are independently selected from the group consisting of:
3-(trifluoromethyl)phenyl
4-bromophenyl,
and
4-fluorophenyl.

6. The polytriazole copolymer of claim 3 , wherein R 3 and R 4 are independently selected from the group consisting of:
3-(trifluoromethyl)phenyl
4-bromophenyl, and
4-fluorophenyl.

7. The polytriazole copolymer of claim 1 , wherein in each R 3 and each R 4 , exactly three of X 1 , X 2 , X 3 , X 4 , and X 5 are hydrogen.

8. The polytriazole copolymer of claim 7 , wherein R 3 and R 4 are independently selected from the group consisting of:
2,4-difluorophenyl,
2,5-difluorophenyl,
2-bromo-4-fluorophenyl,
2-chloro-4-(triphenylmethyl)phenyl,
3-chloro-5-fluorophenyl,
3-chloro-4-fluorophenyl,
4-fluoro-3-(trifluoromethyl)phenyl,
3-bromo-4-methylphenyl, and
3,5-(di-trifluoromethyl)benzyl.

9. The polytriazole copolymer of claim 7 , wherein R 3 and R 4 are 2,5-difluorophenyl.

10. The polytriazole copolymer of claim 1 , wherein in each R 3 and each R 4 , exactly two of X 1 , X 2 , X 3 , X 4 , and X 5 are hydrogen.

11. The polytriazole copolymer of claim 10 , wherein R 3 and R 4 are independently selected from the group consisting of:
4-bromo-2,5-difluorophenyl,
4-bromo-2,6-difluorophenyl,
2,6-dibromo-4-fluorophenyl,
3,5-dibromo-4-methylphenyl,
2,4,6-trimethylphenyl,
2,4,6-trifluorobenzyl,
3,4,5-trifluorobenzyl,
2,3,4-trifluorobenzyl, and
2,4,6-trimethylbenzyl.

12. The polytriazole copolymer of claim 10 , wherein R 3 and R 4 are 4-bromo-2,5-difluorophenyl.

13. The polytriazole copolymer of claim 1 , wherein in each R 3 and each R 4 , exactly one of X 1 , X 2 , X 3 , X 4 , or X 5 is hydrogen.

14. The polytriazole copolymer of claim 1 , wherein in each R 3 and each R 4 , none of X 1 , X 2 , X 3 , X 4 , and X 5 is hydrogen.

15. The polytriazole copolymer of claim 14 , wherein R 3 and R 4 are 2,3,4,5,6-pentafluorophenyl.

16. The polytriazole copolymer of claim 1 , wherein R 3 is 4-fluorophenyl and R 4 is 4-bromophenyl.

17. The polytriazole copolymer of claim 1 , wherein the polytriazole copolymer has a structure according to formula (II):

where:
m, n, R 3 , and R 4 are as defined in formula (I); and
the polytriazole copolymer has a degree of polymerization from 50 to 200.

18. The polytriazole copolymer of claim 1 , wherein the polytriazole copolymer has a structure according to formula (III):

m, n, R 3 , and R 4 are as defined in formula (I); and
the polytriazole copolymer has a degree of polymerization from 25 to 175.

19. The polytriazole copolymer of claim 1 , wherein the polytriazole copolymer has a structure according to formula (IV):

m, n, R 3 , and R 4 are as defined in formula (I); and
the polytriazole copolymer has a degree of polymerization from 75 to 250.

Assignees

• Saudi Arabian Oil Co

Inventors

• Maab Husnul
• Alanazi Nayef M
• Al-Khaldi Turki A

Classifications

• C08G61/123 Primary

  derived from five-membered heterocyclic compounds · CPC title

• C08G2261/12

  Copolymers · CPC title

• C08G2261/148

  Side-chains having aromatic units · CPC title

• C08G2261/3221

  containing one or more nitrogen atoms as the only heteroatom, e.g. pyrrole, pyridine or triazole · CPC title

• C08G2261/334

  containing heteroatoms · CPC title