Copolymers including a triazine group and compositions including them

Patent metadata

Field	Value
Publication number	US-2017198119-A1
Application number	US-201515320562-A
Country	US
Kind code	A1
Filing date	Jun 25, 2015
Priority date	Jun 25, 2014
Publication date	Jul 13, 2017
Grant date	—

Abstract

An ultraviolet light-absorbing oligomer that includes a first divalent unit represented by formula (I): and a second divalent unit represented by formula (II): Each R 1 is independently hydrogen or methyl; V is O or NH; X is bond or X is alkylene or alkyleneoxy group having from 1 to 10 carbon atoms and optionally interrupted by one or more —O— groups and optionally substituted by a hydroxyl group; and R2 is alkyl having from 1 to 22 carbon atoms. Compositions that include fluoropolymers and the oligomers are disclosed. The composition can be an extruded film. Compositions that include pressure sensitive adhesives and these oligomers are disclosed.

First claim

1 . A composition comprising a blend of a fluoropolymer and an ultraviolet light-absorbing oligomer, wherein the ultraviolet light-absorbing oligomer comprises:
a first divalent unit represented by formula:

and
a second divalent unit represented by formula:

wherein
each R 1 is independently hydrogen or methyl;
V is O or NH;
X is a bond, alkylene, or alkyleneoxy, wherein the alkylene or alkyleneoxy have from 1 to 10 carbon atoms and are optionally interrupted by one or more —O— groups and optionally substituted by a hydroxyl group; and
R 2 is alkyl having from 1 to 4 carbon atoms.

2 . The composition of claim 1 , wherein the composition is an extruded film.

3 . The composition of claim 1 , further comprising a hindered amine light stabilizer.

4 . The composition of claim 1 , wherein the ultraviolet light-absorbing oligomer further comprises a third divalent unit represented by formula:

wherein
R 1 is independently hydrogen or methyl;
X is a bond, alkylene, or alkyleneoxy, wherein the alkylene or alkyleneoxy have from 1 to 10 carbon atoms and are optionally interrupted by one or more —O— groups and optionally substituted by a hydroxyl group;
V is O or NH; and
R 3 is hydrogen, alkyl, oxy, alkoxy, or alkanone.

5 . The composition of claim 1 , wherein the ultraviolet light-absorbing oligomer further comprises a fifth divalent unit represented by formula:

wherein
R 1 is independently hydrogen or methyl;
V is O or NH;
X is a bond, alkylene, or alkyleneoxy, wherein the alkylene or alkyleneoxy have from 1 to 10 carbon atoms and are optionally interrupted by one or more —O— groups and optionally substituted by a hydroxyl group;
R is alkyl having from one to four carbon atoms;
n is 0 or 1; and
Z is a benzoyl group optionally substituted by hydroxyl, alkyl, halogen, or hydroxyl or a 2H-benzotriazol-2-yl group optionally substituted by one or more halogens.

6 . The composition of claim 1 , wherein the ultraviolet light-absorbing oligomer further comprises a fourth divalent unit represented by formula:

wherein
Rf represents a fluoroalkyl group having from 1 to 8 carbon atoms optionally interrupted by one —O— group, or Rf represents a polyfluoropolyether group;
R 1 is independently hydrogen or methyl;
Q is a bond, —SO 2 —N(R 5 )—, or —C(O)—N(R 5 )—, wherein R is alkyl having from 1 to 4 carbon atoms or hydrogen; and
m is an integer from 0 to 10.

7 . The composition of claim 1 , wherein the ultraviolet light-absorbing oligomer is in the composition in an amount ranging from 1 percent to 25 percent by weight, based on the total weight of the composition.

8 . The composition of claim 1 , wherein in the second divalent unit, R 1 and R 2 are both methyl.

9 . The composition of claim 1 , further comprising a second, different oligomer comprising the second divalent units and at least one of:
a third divalent unit comprising a pendent 2,2,6,6-tetramethylpiperidinyl group, wherein the nitrogen of the pendent 2,2,6,6-tetramethylpiperidinyl group is substituted by hydrogen, alkyl, alkoxy, or alkanone; or a fifth divalent unit comprising a pendent ultraviolet absorbing group selected from a benzophenone and a benzotriazole.

10 . The composition of claim 1 , wherein the fluoropolymer is present in the blend in an amount of at least 70 percent by weight, based on the total weight of the blend.

11 . The composition of claim 1 , wherein the blend further comprises poly(methyl methacrylate).

12 . The composition of claim 1 , wherein the fluoropolymer is selected from the group consisting of ethylene-tetrafluoroethylene copolymer, a tetrafluoroethylene-hexafluoropropylene copolymer, a tetrafluoroethylene-hexafluoropropylene-vinylidene fluoride copolymer, or polyvinylidene fluoride.

13 . An article comprising the composition of claim 1 , wherein the article is a photovoltaic device, vehicle wrap, graphic film, architectural film, or window film.

14 . An ultraviolet light-absorbing oligomer comprising:
a first divalent unit represented by formula:

and
a second divalent unit represented by formula:

wherein
each R 1 is independently hydrogen or methyl;
V is O or NH;
X is a bond, alkylene, or alkyleneoxy, wherein the alkylene or alkyleneoxy have from 1 to 10 carbon atoms and are optionally interrupted by one or more —O— groups and optionally substituted by a hydroxyl group; and
R 2 is alkyl having from 1 to 22 carbon atoms.

15 . A pressure sensitive adhesive comprising the ultraviolet light-absorbing oligomer of claim 14 .

16 . The ultraviolet light-absorbing oligomer of claim 14 , wherein the ultraviolet light-absorbing oligomer further comprises a third divalent unit represented by formula:

wherein
R 1 is independently hydrogen or methyl;
X is a bond, alkylene, or alkyleneoxy, wherein the alkylene or alkyleneoxy have from 1 to 10 carbon atoms and are optionally interrupted by one or more —O— groups and optionally substituted by a hydroxyl group;
V is O or NH; and
R 3 is hydrogen, alkyl, oxy, alkoxy, or alkanone.

17 . The ultraviolet light-absorbing oligomer of claim 14 , wherein the ultraviolet light-absorbing oligomer further comprises a fifth divalent unit represented by formula:

wherein
R 1 is independently hydrogen or methyl;
V is O or NH;
X is a bond, alkylene, or alkyleneoxy, wherein the alkylene or alkyleneoxy have from 1 to 10 carbon atoms and are optionally interrupted by one or more —O— groups and optionally substituted by a hydroxyl group;
R is alkyl having from one to four carbon atoms;
n is 0 or 1; and
Z is a benzoyl group optionally substituted by hydroxyl, alkyl, halogen, or hydroxyl or a 2H-benzotriazol-2-yl group optionally substituted by one or more halogens.

18 . The ultraviolet light-absorbing oligomer of claim 14 , wherein the ultraviolet light-absorbing oligomer further comprises a fourth divalent unit represented by formula:

wherein
Rf represents a fluoroalkyl group having from 1 to 8 carbon atoms optionally interrupted by one —O— group, or Rf represents a polyfluoropolyether group;
R 1 is independently hydrogen or methyl;
Q is a bond, —SO 2 —N(R 5 )—, or —C(O)—N(R 5 )—, wherein R is alkyl having from 1 to 4 carbon atoms or hydrogen; and
m is an integer from 0 to 10.

19 . The ultraviolet light-absorbing oligomer of claim 14 , wherein the ultraviolet light-absorbing oligomer further comprises a sixth divalent unit comprising a penden

Assignees

• 3M Innovative Properties Co

Inventors

• Olson David B
• Savu Patricia M
• North Diane

Classifications

• C08L27/16 Primary

  Homopolymers or copolymers or vinylidene fluoride · CPC title

• C08J2327/16

  Homopolymers or copolymers of vinylidene fluoride · CPC title

• C09K15/30

  containing heterocyclic ring with at least one nitrogen atom as ring member · CPC title

• C09J133/14

  of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen · CPC title

• C08F14/18

  Monomers containing fluorine · CPC title