IP Library › Granted Patent US 10,723,841
Granted Patent B2
US 10,723,841 · App. 16/047,674 · Granted Jul 28, 2020

Method for preparing compound and method for preparing polymer employing the same

Inventors: Po-Hsien Ho (Taipei, TW); Chih-Hsiang Lin (Taipei, TW); Feng-Jen Tsai (Taipei, TW); Cheng-Hsing Fan (Tainan, TW); Yih-Her Chang (Baoshan Township, TW); Hsin-Ching Kao (Baoshan Township, TW); Chien-Ming Chen (Taoyuan, TW)
Assignee: INDUSTRIAL TECHNOLOGY RESEARCH
C08G75/0236C07C315/00C07C315/02C07C317/22C07C319/14C07C319/20C07C323/00C08G75/02C08G75/025C08G75/029C08G75/0227C08G75/0272C08G75/20C08G75/23
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Quick Facts
Patent No.
US 10,723,841
App. No.
16/047,674
Granted
Jul 28, 2020
Kind
B2
Abstract

A method for preparing a compound and a method for preparing a polymer employing the same are provided. The method for preparing a compound includes reacting a compound having a structure represented by Formula (I) with a compound having a structure represented by Formula (III) in the presence of a compound having a structure represented by Formula (II) to obtain a compound having a structure represented by Formula (IV) wherein Ar 1 is substituted or unsubstituted aryl group; X is —O—, —S—, or —NH—; R 1 is independently hydrogen or C 1-6 alkyl group; R 2 is hydroxyl group, C 1-6 alkyl group, phenyl group, or tolyl group; and R 3 is independently C 1-6 alkyl group, C 5-8 cycloalkyl group, or C 2-6 alkoxyalkyl group.

Claims (53)

1. A method for preparing a compound, comprising:

reacting a compound having a structure represented by Formula (I) with a compound having a structure represented by Formula (III) in the presence of a compound having a structure represented by Formula (II), obtaining a compound having a structure represented by Formula (IV)

wherein Ar 1 is substituted or unsubstituted aryl group; X is —O—, —S—, or —NH—; R 1 is independently hydrogen or C 1-6 alkyl group; R 2 is hydroxyl group, C 1-6 alkyl group, phenyl group, or tolyl group; and R 3 is independently C 1-6 alkyl group, C 5-8 cycloalkyl group, or C 2-6 alkoxyalkyl group.

2. The method as claimed in claim 1 , wherein Ar 1 is substituted or unsubstituted phenyl group, biphenyl group, naphthyl group, thienyl group, indolyl group, phenanthrenyl group, indenyl group, anthracenyl group, or fluorenylene group.

3. The method as claimed in claim 1 , wherein R 1 is independently hydrogen, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, t-butyl group, sec-butyl group, isobutyl group, pentyl group, or hexyl group.

4. The method as claimed in claim 1 , wherein the compound having the structure of Formula (I) is

wherein R 1 is independently hydrogen or C 1-6 alkyl group; and R 4 is independently hydrogen or C 1-6 alkyl group.

5. The method as claimed in claim 1 , wherein the compound having the structure of Formula (II) is sulfuric acid, methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, or a combination thereof.

6. The method f as claimed in claim 1 , wherein R 3 is independently methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, t-butyl group, sec-butyl group, isobutyl group, pentyl group, hexyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, or

wherein 1≤n≤5, 0≤m≤4, and 1≤n+m≤5.

7. The method as claimed in claim 1 , wherein the compound having the structure of Formula (IV) is

wherein R 1 is independently hydrogen or C 1-6 alkyl group; R 4 is independently hydrogen or C 1-6 alkyl group; and R 3 is independently C 1-6 alkyl group, C 5-8 cycloalkyl group, or C 2-6 alkoxyalkyl group.

8. The method as claimed in claim 1 , further comprising:

reacting the compound having the structure represented by Formula (IV) with a compound (A), obtaining a compound having the structure represented by Formula (V)

wherein the compound (A) is nitric acid, sulfuric acid, acetic acid, hydrogen peroxide, or a combination thereof; Ar 1 is substituted or unsubstituted; X is —O—, —S—, or —NH—; R 1 is independently hydrogen or C 1-6 alkyl group; and R 3 is independently C 1-6 alkyl group, C 5-8 cycloalkyl group, or C 2-6 alkoxyalkyl group.

9. The method as claimed in claim 8 , wherein the compound having the structure of Formula (V) is

wherein R 1 is independently hydrogen or C 1-6 alkyl group; R 4 is independently hydrogen or C 1-6 alkyl group; and R 3 is independently C 1-6 alkyl group, C 5-8 cycloalkyl group, or C 2-6 alkoxyalkyl group.

10. A method for preparing a polymer, comprising:

reacting a compound having a structure represented by Formula (I) with a compound having a structure represented by Formula (III) in the presence of a compound having a structure represented by Formula (II), obtaining a compound having a structure represented by Formula (IV);

reacting the compound having the structure represented by Formula (IV) with a compound (A), obtaining a compound having the structure represented by Formula (V), wherein the compound (A) is nitric acid, sulfuric acid, acetic acid, hydrogen peroxide, or a combination thereof; and

reacting the compound having the structure represented by Formula (V) with a compound having a structure represented by Formula (VI), obtaining a polymer having a repeat unit represented by Formula (VII)

wherein Ar 1 is substituted or unsubstituted aryl group; X is —O—, —S—, or —NH—; R 1 is independently hydrogen or C 1-6 alkyl group; R 2 is hydroxyl group, C 1-6 alkyl group, phenyl group, or tolyl group; R 3 is independently C 1-6 alkyl group, C 5-8 cycloalkyl group, or C 2-6 alkoxyalkyl group; R 5 is hydroxyl group, C 1-6 alkyl group, phenyl group, or tolyl group; and Ar 2 is substituted or unsubstituted aryl diradical.

11. The method as claimed in claim 10 , wherein Ar 1 is substituted or unsubstituted phenyl group, biphenyl group, naphthyl group, thienyl group, indolyl group, phenanthrenyl group, indenyl group, anthracenyl group, or fluorenylene group.

12. The method as claimed in claim 10 , wherein R 1 is independently hydrogen, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, t-butyl group, sec-butyl group, isobutyl group, pentyl group, or hexyl group.

13. The method as claimed in claim 10 , wherein the compound having the structure of Formula (I) is

wherein R 1 is independently hydrogen or C 1-6 alkyl group; and R 4 is independently hydrogen or C 1-6 alkyl group.

14. The method as claimed in claim 10 , wherein the compound having the structure of Formula (II) is sulfuric acid, methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid or a combination thereof.

15. The method as claimed in claim 10 , wherein R 3 is independently methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, t-butyl group, sec-butyl group, isobutyl group, pentyl group, hexyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, or

wherein 1≤n≤5, 0≤m≤4, and 1≤n+m≤5.

16. The method as claimed in claim 10 , wherein the compound having the structure of Formula (IV) is

wherein R 1 is independently hydrogen or C 1-6 alkyl group; R 4 is independently hydrogen or C 1-6 alkyl group; and R 3 is independently C 1-6 alkyl group, C 5-8 cycloalkyl group, or C 2-6 alkoxyalkyl group.

17. The method as claimed in claim 10 , wherein the compound having the structure of Formula (V) is

wherein R 1 is independently hydrogen or C 1-6 alkyl group; R 4 is independently hydrogen or C 1-6 alkyl group; and R 3 is independently C 1-6 alkyl group, C 5-8 cycloalkyl group, or C 2-6 alkoxyalkyl group.

18. The method as claimed in claim 10 , wherein the compound having the structure of Formula (VI) is sulfuric acid, methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, or a combination thereof.

19. The method as claimed in claim 10 , wherein Ar 2 is substituted or unsubstituted phenylene group, biphenylene group, naphthylene group, thienylene group, indolylene group, phenanthrenylene group, indenylene group, anthracenylene group, or fluorenylene group.

20. The method as claimed in claim 10 , further comprising:

reacting a nucleophile with the polymer having the repeat unit represented by Formula (VII), obtaining a polymer having a repeat unit represented by Formula (VIII)

wherein X is —O—, —S—, or —NH—; R 1 is independently hydrogen or C 1-6 alkyl group; R 3 is independently C 1-6 alkyl group, C 5-8 cycloalkyl group, or C 2-6 alkoxyalkyl group; R 5 is hydroxyl group, C 1-6 alkyl group, phenyl group, or tolyl group; and Ar 2 is substituted or unsubstituted aryl diradical.

21. The method as claimed in claim 20 , wherein the nucleophile is pyridine, 4-methylpyridine, triethylamine, potassium chloride, methanol, ethanol, dimethylformamide, dimethylacetamide, N-methylpyrrolidone, or a combination thereof.

22. The method as claimed in claim 20 , when X of the polymer having the repeat unit represented by Formula (VIII) is —O— or —NH—, further comprising:

reacting the polymer having the repeat unit represented by Formula (VIII) with hydrogen peroxide, obtaining a polymer having a repeat unit represented by Formula (X)

wherein X is —O— or —NH—; R 1 is independently hydrogen or C 1-6 alkyl group; and Ar 2 is substituted or unsubstituted aryl diradical.

23. The method as claimed in claim 20 , wherein a polymer having the repeat unit represented by Formula (VIII) is reacted with hydrogen peroxide in the presence of a compound having a structure represented by Formula (IX)

wherein R 6 is C 1-6 alkyl group.

24. The method as claimed in claim 10 , when X of the polymer having the repeat unit represented by Formula (VII) is —S—, further comprising:

reacting the polymer having the repeat unit represented by Formula (VII) with hydrogen peroxide, obtaining a polymer having a repeat unit represented by Formula (XI)

wherein X is —S—; R 1 is independently hydrogen or C 1-6 alkyl group; R 3 is independently C 1-6 alkyl group, C 5-8 cycloalkyl group, or C 2-6 alkoxyalkyl group; R 5 is hydroxyl group, C 1-6 alkyl group, phenyl group, or tolyl group; and Ar 2 is substituted or unsubstituted aryl diradical.

25. The method as claimed in claim 24 , wherein the polymer having the repeat unit represented by Formula (VII) is reacted with hydrogen peroxide in the presence of a compound having a structure represented by Formula (IX)

wherein R 6 is C 1-6 alkyl group.

26. The method as claimed in claim 24 further comprising:

reacting a nucleophile with the polymer having the repeat unit represented by Formula (XI), obtaining a polymer having a repeat unit represented by Formula (XII)

wherein R 1 is independently hydrogen or C 1-6 alkyl group; R 3 is independently C 1-6 alkyl group, C 5-8 cycloalkyl group, or C 2-6 alkoxyalkyl group; R 5 is hydroxyl group, C 1-6 alkyl group, phenyl group, or tolyl group; and Ar 2 is substituted or unsubstituted aryl diradical.

27. The method as claimed in claim 26 , wherein the nucleophile is pyridine, 4-methylpyridine, triethylamine, potassium chloride, methanol, ethanol, dimethylformamide, dimethylacetamide, N-methylpyrrolidone, or a combination thereof.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 17, 2018
From: HO, PO-HSIEN; LIN, CHIH-HSIANG; TSAI, FENG-JEN; FAN, CHENG-HSING; CHANG, YIH-HER; KAO, HSIN-CHING; CHEN, CHIEN-MING
To: INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE
Reel/Frame 046857/0518 →
Priority Claims (1)
TW 106145978 A · Dec 27, 2017 · national
Continuity (2)
Provisional Application 62539681 · Aug 1, 2017
Related Publication 20190040202A1 · Feb 7, 2019