Polymeric matrices with ionic additives

Patent metadata

Field	Value
Publication number	US-11053373-B2
Application number	US-201615741387-A
Country	US
Kind code	B2
Filing date	Jun 30, 2016
Priority date	Jul 7, 2015
Publication date	Jul 6, 2021
Grant date	Jul 6, 2021

Abstract

Polymeric compositions include at least one polymer that is free of ester linkages and an additive that is a benzotriazole phenolate salt with substituents either ortho to the phenol hydroxide group and/or para to the phenol hydroxide group. The substituted benzotriazole phenolate salts can be prepared from substituted benzotriazole phenols. The ortho substituent group can be a simple hydrocarbon, alkoxy, or amino group, or the ortho substituent group can be a linking group, linking the benzotriazole phenolate to another benzotriazole phenolate group.

First claim

What is claimed is:

1. A polymeric composition comprising:
at least one polymer, wherein the at least one polymer comprises a polymer that is essentially free of ester linkages, comprising an olefinic polymer or copolymer, a polyurethane, a polyamide, an aromatic polymer or copolymer, and combinations thereof, and
an additive comprising at least one macromolecular salt composition, the macromolecular salt composition comprising an assembly of metal salts comprising repeat units of a substituted benzotriazole phenolate anion and a metal cation with the structure:

wherein each R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 , independently comprises a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, a halogen atom, or a substituted heteroatom group comprising a —B(OR 18 )(OR 19 ), a —SiR 20 3 , a —CH 2 —R 9 , an —O—R 9 , a
—N—R 9 R 10 , a —S—R 9 , a —S(O)—R 9 , or a —S(O) 2 —R 9 group, where S(O) is a sulfinyl group S═O, and S(O) 2 is a sulfonyl group O═S═O, R 9 comprises 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, wherein the —B(OR 18 )(OR 19 ), —SiR 20 3 ,
—CH 2 —R 9 , —O—R 9 , —N—R 9 R 10 , —S—R 9 , —S(O)—R 9 , or —S(O) 2 —R 9 group may be neutral or anionic, and R 10 comprises 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, R 18 and R 19 are independently hydrogen atoms, alkyl groups or R 18 and R 19 together with the atoms connecting form a heterocyclic ring structure, each R 20 independently comprises an alkyl group;
n is an integer of 1-4;
and M is a metal atom with a valency of n;
and the macromolecular assembly comprises 2-4 repeat units.

2. The polymer composition of claim 1 , wherein the at least one polymer comprises polyethylene, polypropylene, a copolymer of ethylene and propylene, a copolymer of ethylene or propylene with higher alpha-olefin monomers, a copolymer of ethylene or propylene with diene monomers, or combinations thereof.

3. The polymer composition of claim 1 , wherein n=1 and M is lithium, sodium, or potassium.

4. The polymer composition of claim 1 , wherein R 1 comprises an —O—R 9 group wherein R 9 comprises:
an alkyl group with 1-20 carbon atoms; or
an aryl group; and
R 3 is an alkyl group with 1-20 carbon atoms.

5. The polymer composition of claim 4 , wherein R 9 comprises:
an alkyl group with 1-6 carbon atoms; or
an aryl group comprising a 3-methyl phenyl group, or a 4-methyl phenyl group.

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

R 3 is an alkyl group with 1-20 carbon atoms.

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

8. The polymer composition of claim 1 , wherein R 1 comprises a hydrogen atom, an alkyl, alkylene, an aryl group, or an aralkylene group; and
R 3 is an alkyl group with 1-20 carbon atoms, or an alkoxy group with 1-6 carbon atoms.

9. The polymer composition of claim 1 , wherein R 1 comprises a halogen atom or a —SiR 20 3 group wherein each R 20 comprises an alkyl group with 1-4 carbon atoms; and
R 3 is an alkyl group with 1-20 carbon atoms.

10. The polymer composition of claim 1 , wherein the repeat unit of the macromolecular salt has the structure:

where X comprises a —CH 2 —, —O—, —S—, —S(O)—, —S(O) 2 —, or —NR 10 — linking group where R 10 comprises 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 comprises a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, or a halogen atom;
m=0.5, 1, or 2;
M is a metal ion with a valency of 2m such that M is lithium, sodium or potassium when m=0.5;
M is calcium, magnesium, or cobalt, when m=1; and M is vanadium or titanium when m=2.

11. The polymer composition of claim 10 , wherein X comprises a —CH 2 — linking group, and R 3 and R 16 each comprises an alkyl group with 8 carbon atoms.

12. The polymer composition of claim 10 , wherein X comprises a —NR 10 — linking group, where R 10 comprises a hydrogen atom or a methyl group, and R 3 and R 16 each comprises an alkyl group with 8 carbon atoms.

13. The polymer composition of claim 10 , wherein X comprises an —S— linking group, and R 3 and R 16 each comprises an alkyl group with 8 carbon atoms.

14. The polymer composition of claim 1 , wherein the at least one macromolecular salts comprises a mixture of macromolecular salts.

15. The polymer composition of claim 1 , further comprising at least one additional additive.

16. The polymer composition of claim 15 , the at least one additive comprising pigments, light stabilizers, primary and secondary antioxidants, metal deactivators, nucleators, hindered amines, hindered phenols, fatty acid metal salts, triester phosphites, phosphoric acid salts, fluorine-containing compounds and combinations thereof.

17. A method of preparing the polymer composition according to claim 1 comprising:
providing at least one polymer, wherein the at least one polymer comprises a polymer that is essentially free of ester linkages, comprising an olefinic polymer or copolymer, a polyurethane, a polyamide, an aromatic polymer or copolymer, and combinations thereof,
providing at least one macromolecular substituted benzotriazole phenolate salt; and
mixing the polymer and at least one macromolecular substituted benzotriazole phenolate salt to form a polymer composition.

Assignees

• 3M Innovative Properties Co

Inventors

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

Classifications

• C08K5/3472 Primary

  Five-membered rings · CPC title

• C08F10/06

  Propene · CPC title

• C08K5/41

  Compounds containing sulfur bound to oxygen · CPC title

• C08K5/3475 Primary

  condensed with carbocyclic rings · CPC title

• C08K5/378

  containing heterocyclic rings · CPC title