Curable poly(polyphenylene ether) oligomer compositions for coatings

Patent metadata

Field	Value
Publication number	US-11897990-B2
Application number	US-202017606905-A
Country	US
Kind code	B2
Filing date	Apr 3, 2020
Priority date	Apr 30, 2019
Publication date	Feb 13, 2024
Grant date	Feb 13, 2024

Abstract

An ultraviolet light-curable coating composition includes 5-40 weight percent of an ultraviolet light-curable poly(polyphenylene ether) oligomer; 60-95 weight percent of an ultraviolet light-curable monomer, oligomer, polymer, or a combination thereof; and 0.01-3 weight percent of a photoinitiator.

First claim

What is claimed is:

1. An ultraviolet light-curable coating composition comprising:
5-40 weight percent of an ultraviolet light-curable poly(polyphenylene ether) oligomer;
60-95 weight percent of an ultraviolet light-curable monomer, oligomer, polymer, or a combination thereof, wherein the monomer comprises a linear or branched alkyl group, a non-aromatic cyclic group, or a partially aromatic group; and
0.01-3 weight percent of a photoinitiator activated by ultraviolet light.

2. The ultraviolet light-curable coating composition of claim 1 , wherein the ultraviolet light-curable poly(polyphenylene ether) oligomer comprises the structure

wherein
each occurrence of Q 1 and Q 2 is independently halogen, unsubstituted or substituted C 1-12 primary or secondary hydrocarbyl, C 1-12 hydrocarbylthio, C 1-12 hydrocarbyloxy, or C 2-12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms;
each occurrence of Q 3 and Q 4 is independently hydrogen, halogen, unsubstituted or substituted C 1 -C 12 primary or secondary hydrocarbyl, C 1 -C 12 hydrocarbylthio, C 1-12 hydrocarbyloxy, or C 2-12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms;
x and y are each independently 0-30;
Z is hydrogen, allyl, vinyl, or (meth)acrylate provided that at least one Z is allyl, vinyl, or (meth)acrylate;
L is of the formula

wherein
each occurrence of R 3 , R 4 , R 5 , and R 6 is independently hydrogen, halogen, unsubstituted or substituted C 1-12 primary or secondary hydrocarbyl, C 1-12 hydrocarbylthio, C 1-12 hydrocarbyloxy, or C 2-12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms;
w is 0 or 1; and
Y is

wherein
each occurrence of R 7 is independently hydrogen or C 1-12 hydrocarbyl,
each occurrence of R 8 and R 9 is independently hydrogen, C 1-12 hydrocarbyl, or

R 8 and R 9 together form a C 4-12 cyclohydrocarbylene with the carbon atom; or

L is of the formula

wherein
E is 6-100,
each occurrence of R is independently an unsubstituted or substituted C 1-13 alkyl, C 1-13 alkoxy, C 3-6 cycloalkyl, C 3-6 cycloalkoxy, C 6-14 aryl, C 6-10 aryloxy, C 7-13 arylalkylene, or C 7-13 alkylarylene; each p and q are independently 0 or 1,
R 1 is a divalent C 2-8 aliphatic group,
each occurrence of M is independently halogen, cyano, nitro, C 1-8 alkylthio, C 1-8 alkyl, C 1-8 alkoxy, C 2-8 alkenyl, C 2-8 alkenyloxy, C 3-8 cycloalkyl, C 3-8 cycloalkoxy, C 6-10 aryl, C 6-10 aryloxy, C 7-12 aralkyl, C 7-12 aralkoxy, C 7-12 alkylaryl, or C 7-12 alkylaryloxy, and
each n is independently 0, 1, 2, 3, or 4.

3. The ultraviolet light-curable coating composition of claim 1 , wherein the ultraviolet light-curable poly(polyphenylene ether) oligomer comprises
at least one allyl, vinyl, or (meth)acrylate terminal group;
a poly(polyphenylene ether) block of the formula

wherein
each occurrence of Z 1 is independently halogen, unsubstituted or substituted C 1-12 primary or secondary hydrocarbyl, C 1-12 hydrocarbylthio, C 1-12 hydrocarbyloxy, or C 2 -C 12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms, and
each occurrence of Z 2 is independently hydrogen, halogen, unsubstituted or substituted C 1-12 primary or secondary hydrocarbyl, C 1-12 hydrocarbylthio, C 1-12 hydrocarbyloxy, or C 2-12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms; and a polysiloxane block comprising repeating units of the formula
a polysiloxane block comprising repeating units having the structure

wherein
each occurrence of R 3 is independently C 1-12 hydrocarbyl or C 1-12 halohydrocarbyl, and the polysiloxane block further comprises a terminal unit of formula (6)

wherein
Y is hydrogen, halogen, C 1-12 hydrocarbyl, or C 1-12 hydrocarbyloxy, and
each occurrence of R 3 is independently hydrogen, C 1-12 hydrocarbyl, or C 1-12 halohydrocarbyl.

4. The ultraviolet light-curable coating composition of claim 1 , wherein the ultraviolet light-curable poly(polyphenylene ether) oligomer comprises the polysiloxane block is of the formula

wherein n has an average value of 5-100.

5. The ultraviolet light-curable coating composition of claim 1 , wherein the poly(polyphenylene ether) oligomer comprises at least one terminal (meth)acrylate group.

6. The ultraviolet light-curable coating composition of claim 1 , wherein the ultraviolet light-curable poly(polyphenylene ether) comprises the formula

wherein
each occurrence of Q 1 and Q 2 is independently halogen, unsubstituted or substituted C 1-6 primary or secondary hydrocarbyl, C 1-6 hydrocarbylthio, C 1-6 hydrocarbyloxy, or C 2-6 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms;
each occurrence of Q 3 and Q 4 is independently hydrogen, halogen, unsubstituted or substituted C 1 -C 6 primary or secondary hydrocarbyl, C 1 -C 6 hydrocarbylthio, C 1-6 hydrocarbyloxy, or C 2-6 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms;
x and y are each independently 0-30; and
L is of the formula (3)

wherein
each occurrence of R 3 , R 4 , R 5 , and R 6 is independently hydrogen, halogen, unsubstituted or substituted C 1-6 primary or secondary hydrocarbyl, C 1-6 hydrocarbylthio, C 1-6 hydrocarbyloxy, or C 2-6 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms;
w is 0 or 1;
R 10 is methyl or hydrogen; and
Y is

wherein
each occurrence of R 7 is independently hydrogen or C 1-6 hydrocarbyl,
each occurrence of R 8 and R 9 is independently hydrogen, C 1-6 hydrocarbyl.

7. The ultraviolet light-curable coating composition of claim 1 , wherein the ultraviolet light-curable poly(polyphenylene ether) oligomer is of the formula

wherein
each occurrence of Q 5 and Q 6 is independently methyl, cyclohexyl, phenyl, di-n-butylaminomethyl, or morpholinomethyl;
each occurrence of a and b is independently 0-20, with the proviso that the sum of a and b is at least 2; and
each occurrence of R 10 is methyl or hydrogen.

8. The ultraviolet light-curable coating composition of claim 1 , wherein the ultraviolet light-curable poly(polyphenylene ether) has a number average molecular weight of 500-7,000

Assignees

• Shpp Global Tech Bv

Inventors

• Rice Brian Jason
• Tarkin-Tas Eylem

Classifications

• C08F290/062 Primary

  Polyethers · CPC title

• C08F290/068 Primary

  Polysiloxanes · CPC title

• C08J5/249

  characterised by the additives used in the prepolymer mixture · CPC title

• C09D4/00

  Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16} · CPC title

• C09D151/085

  on to polysiloxanes · CPC title