Oligomeric materials for UV blocking applications and methods thereof

Patent metadata

Field	Value
Publication number	US-12180150-B2
Application number	US-202017433176-A
Country	US
Kind code	B2
Filing date	Feb 19, 2020
Priority date	Feb 25, 2019
Publication date	Dec 31, 2024
Grant date	Dec 31, 2024

Abstract

The present invention describes an oligomer for use as a UV stabiliser. In particular, the oligomer is suitable for use as a UV stabiliser in a polymer matrix. The present invention also describes a method of forming said oligomer. The method of forming said oligomer comprises a polymerising step, wherein the polymerising step comprises forming a C—C bond on the hydroxyphenyl ring of a monomer. In preferred embodiments, the oligomer is formed from polymerizing bio-derived monomer such as curcumin, its hydrogenated analogue, and an aldol condensation product of cyclic ketone and vanillin.

First claim

The invention claimed is:

1. An oligomer of Formula (I):

wherein X is selected from a heteroatom, C 1 -C 8 acyclic, cyclic or heterocyclic linker; and
n is an integer selected from 2 to 15;
wherein the oligomer does not contain a metal impurity.

2. The oligomer of claim 1 , wherein X is a C 4 -C 8 acyclic, cyclic or heterocyclic linker.

3. The oligomer of claim 1 , wherein X is selected from

wherein m is an integer selected from 0 to 5;
Y 1 , Y 2 , Z 1 and Z 2 are independently H or C 1 -C 5 alkyl; and
Y 3 and Z 3 are independently C 4 -C 6 cycloalkyl.

4. The oligomer according to claim 1 , wherein X is selected from

5. The oligomer according to claim 1 , wherein n is an integer selected from 3 to 8.

6. The oligomer according to claim 1 , having a number average molecular weight of about 1000 Da to about 3000 Da.

7. The oligomer according to claim 1 , having a UV absorption within the range of about 200 nm to about 500 nm.

8. The oligomer according to claim 1 , having a molar extinction coefficient of more than 30,000 M −1 cm −1 .

9. A method of forming an oligomer, the method including the step of:
a) providing a monomer of Formula (II)

wherein X is selected from a heteroatom, C 1 -C 8 acyclic, cyclic or heterocyclic linker; and
b) polymerising the monomer to form an oligomer of Formula (I);

wherein the polymerising step comprises forming a C—C bond on the hydroxyphenyl ring of Formula (II);
wherein the polymerizing step is catalysed by an enzyme.

10. The method of claim 9 , wherein the C—C bond is formed at an ortho position on the hydroxyphenyl ring of Formula (II).

11. The method according to claim 9 , wherein the polymerising step is catalysed by laccase.

12. The method according to claim 9 , wherein the polymerising step is performed in a solvent mixture, the solvent mixture comprising an aqueous solvent and another solvent, the combination of which results in a final single phase.

13. The method according to claim 9 , wherein the monomer of Formula (II) is selected from:

14. A composite, comprising:
a) an oligomer of Formula (I)

wherein X is selected from a heteroatom, C 1 -C 8 acyclic, cyclic or heterocyclic linker; and
n is an integer selected from 2 to 15; and
b) a polymer matrix.

15. The composite of claim 14 , wherein the polymer matrix is selected from polyvinyl chloride (PVC) or polystyrene (PS).

16. The composite of claim 14 , wherein the oligomer of Formula (I) is present from about 1 wt/wt % to about 10 wt/wt %.

17. The composite according to claim 14 , having a transmittance of more than 90% at about 400 nm to about 800 nm.

18. The composite according to claim 14 , having a degradation of less than 20% after exposure to UV light for 120 h.

19. The composite according to claim 14 , having a leaching rate in 95% ethanol of less than 20%.

20. The composite according to claim 14 , wherein the composite does not contain a metal impurity.

Assignees

• Agency Science Tech & Res

Inventors

• Ramalingam Balamurugan

Classifications

• C08G2261/93

  Applications in textiles, fabrics and yarns · CPC title

• C08G2261/43

  Chemical oxidative coupling reactions, e.g. with FeCl3 · CPC title

• C08G2261/142

  Side-chains containing oxygen · CPC title

• C07C2601/06

  with a five-membered ring · CPC title

• C12P7/26

  Ketones · CPC title