Modified copolymer, method for preparing the same, and method for preparing paste

Patent metadata

Field	Value
Publication number	US-10954329-B2
Application number	US-201816232581-A
Country	US
Kind code	B2
Filing date	Dec 26, 2018
Priority date	Sep 25, 2018
Publication date	Mar 23, 2021
Grant date	Mar 23, 2021

Abstract

A modified copolymer is provided. The modified copolymer includes a random copolymer of a repeat unit of formula (I) and a repeat unit of formula (II)

wherein M is derived from monomers with double bonds, R is a direct bond or an aliphatic hydrocarbon chain group having 1 to 12 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 16 carbon atoms, an alkylcarbonyloxy group having 2 to 6 carbon atoms, a carbonyl group, an ether group, an ester group, an amide group, an aromatic group having 6 to 16 carbon atoms, or a divalent group having any of the above groups, wherein m and x are positive integers less than 50. The weight average molecular weight of the modified copolymer is between 3000 and 30000.

First claim

What is claimed is:

1. A modified copolymer, which is a random copolymer comprising a repeat unit of Formula (I) and a repeat unit of Formula (II)

wherein M is derived from monomers with double bonds, R is a direct bond or an aliphatic hydrocarbon chain group having 1 to 12 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 16 carbon atoms, an alkylcarbonyloxy group having 2 to 6 carbon atoms, a carbonyl group, an ether group, an ester group, an amide group, an aromatic group having 6 to 16 carbon atoms, or a divalent group having any of the above groups, m and x are positive integers less than 50, and the modified copolymer has a weight average molecular weight between 3000 and 30000.

2. The modified copolymer as claimed in claim 1 , wherein the random copolymer further comprises a repeat unit of Formula (III) and/or a repeat unit of Formula (IV),

wherein M is derived from monomers with double bonds, R is a direct bond or an aliphatic hydrocarbon chain group having 1 to 12 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 16 carbon atoms, an alkylcarbonyloxy group having 2 to 6 carbon atoms, a carbonyl group, an ether group, an ester group, an amide group, an aromatic group having 6 to 16 carbon atoms, or a divalent group having any of the above groups; and m, y, z, and n are independently a positive integer less than 50.

3. The modified copolymer as claimed in claim 2 , wherein the repeat unit of Formula (I), the repeat unit of Formula (II), the repeat unit of Formula (III), and/or the repeat unit of Formula (IV) are arranged in a random fashion.

4. The modified copolymer as claimed in claim 1 , wherein M is a repeat unit of Formula (VI) which is derived from a monomer of Formula (VII):

wherein R 8 , R 9 , R 10 and R 11 are independently hydrogen, straight or branched C 1 -C 12 alkyl group or straight or branched C 1 -C 12 alkoxy group, straight or branched C 1 -C 12 alkylamine group, C 5 -C 12 cycloalkyl group, C 2 -C 8 epoxy group, C 2 -C 8 nitrocyclic group, C 6 -C 12 aryl group, —C(═O)OR 3 , —C(═O)NHR 4 , —OR 5 , —NHR 6 , —R 7 COOH, or one of R 8 and R 9 and one of R 10 and R 11 link together with the carbon atoms to which R 8 , R 9 , R 10 , and R 11 are attached to form C 5 -C 12 cycloalkyl group or cycloalkenyl group; wherein R 3 , R 4 , R 5 or R 6 are independently hydrogen, straight or branched C 1 -C 12 alkyl group, C 5 -C 12 cycloalkyl group, C 2 -C 8 alkoxy group, C 6 -C 12 aryl group, or a combination thereof; R 7 is straight or branched C 1 -C 12 alkyl group, or straight or branched C 1 -C 12 alkoxy group.

5. The modified copolymer as claimed in claim 4 , wherein one of R 8 , R 9 , R 10 , and R 11 is dicyclopentadienyl group, oxetanyl group, or a derivative thereof.

6. The modified copolymer as claimed in claim 4 , wherein R 3 , R 4 , R 5 or R 6 is

wherein R 12 is hydrogen, straight or branched C 1 -C 12 alkyl group, straight or branched C 1 -C 12 alkoxy group, or straight or branched C 1 -C 12 alkylamine group; p is an integer from 1 to 12; R 16 is straight or branched C 1 -C 12 alkyl group; R 17 is hydrogen, straight or branched C 1 -C 12 alkyl group; and d is an integer from 1 to 600.

7. The modified copolymer as claimed in claim 4 , wherein the monomer comprises dicyclopentenyloxyethyl acrylate, 3-ethyl-3-(methacryloyloxy)methyloxetane, 3,4-epoxycyclohexylmethyl acrylate, alkoxylated lauryl acrylate, 2-(2-ethoxyethoxy)ethyl acrylate, tetrahydrofurfuryl acrylate, lauryl acrylate, isodecyl acrylate, 3,3,5-trimethylcyclohexyl acrylate, isobornyl acrylate, isooctyl acrylate, tridecyl acrylate, cyclic trimethylolpropane formal acrylate, 2-hydroxyethyl acrylate, 2-ethylhexyl acrylate, vinylpyrrolidone, or a combination thereof.

8. The modified copolymer as claimed in claim 1 , wherein R is straight or branched C 1 -C 12 alkyl group, cycloalkyl group, straight or branched alkoxy group, straight or branched acyl group, aryl group, straight or branched nitroalkyl group, ether group, ester group, keto group, azo group, or a combination thereof.

9. The modified copolymer as claimed in claim 1 , wherein R is —R 13 —(CH 2 ) p —, —R 14 —O—(CH 2 ) p —, —R 15 —N—(CH 2 ) p —, wherein R 13 , R 14 , and R 15 are independently straight or branched C 1 -C 12 alkyl group, cycloalkyl group, phenyl group, benzyl group, imidazol group, benzimidazol group, 1,3,4-thiadiazole group, or pyridine group; and p is 0 or an integer from 1 to 12.

10. A method for preparing a modified copolymer, comprising:
mixing a copolymer of Formula (V), a monomer having a double bond, an initiator, and a solvent to form a prepolymer; and
irradiating the prepolymer with an ultraviolet light to undergo a grafting reaction, wherein the weight ratio of the copolymer of Formula (V) to the monomer is from 6:1 to 1:6,

wherein a is a positive integer less than 50, b is an integer from 5 to 25, R is a direct bond or an aliphatic hydrocarbon chain group having 1 to 12 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 16 carbon atoms, an alkylcarbonyloxy group having 2 to 6 carbon atoms, a carbonyl group, an ether group, an ester group, an amide group, an aromatic group having 6 to 16 carbon atoms, or a divalent group having any of the above groups, and the copolymer of formula (V) has a weight average molecular weight between 2000 and 6000.

11. The method as claimed in claim 10 , wherein the monomer having a double bond has a structure represented by Formula (VII):

wherein R 8 , R 9 , R 10 and R 11 are independently hydrogen, straight or branched C 1 -C 12 alkyl group or straight or branched C 1 -C 12 alkoxy group, straight or branched C 1 -C 12 alkylamine group, C 5 -C 12 cycloalkyl group, C 2 -C 8 epoxy group, C 2 -C 8 nitrocyclic group, C 6 -C 12 aryl group, —C(═O)OR 3 , —C(═O)NHR 4 , —OR 5 , —NHR 6 , —R 7 COOH, or one of R 8 and R 9 and one of R 10 and R 11 link together with the carbon atoms to which R 8 , R 9 , R 10 , and R 11 are attached to form C 5 -C 12 cycloalkyl group or cycloalkenyl group; wherein R 3 , R 4 , R 5 or R 6 are independently hydrogen, straight or branched C 1 -C 12 alkyl group, C 5 -C 12 cycloalkyl group, C 2 -C 8 alkoxy group, C 6 -C 12 aryl group or a combination thereof and R 7 is straight or branched C 1 -C 12 alkyl group or straight or branched C 1 -C 12 alkoxy group.

12. The method as claimed in claim 11 , wherein one of R 8 , R 9 , R 10 , and R 11 is dicyclopentadienyl group, oxetanyl group, or a derivative thereof.

13. The method as claimed in claim 11 , wherein R 3 , R 4 , R 5 or R 6 is selected from the group consisting of

wherein R 12 is hydrogen, straight or branched C 1 -C 12 alkyl group, straight or branched C 1 -C 12 alkoxy group, or straight or branched C 1 -C 12 alkylamine group; p is an integer from 1 to 12; R 16 is straight or branched C 1 -C 12 alkyl group; R 17 is hydrogen, straight or branche

Assignees

• Ind Tech Res Inst

Inventors

• Ho Shou-Yi
• Chiou Kuo-Chan

Classifications

• C08F2/48

  by ultraviolet or visible light · CPC title

• C08F212/08

  Styrene · CPC title

• C08K3/042

  Graphene or derivatives, e.g. graphene oxides · CPC title

• C08F257/02 Primary

  on to polymers of styrene or alkyl-substituted styrenes · CPC title

• C08F220/70 Primary

  Nitriles; Amides; Imides · CPC title