IP Library Granted Patent US 9,328,188
Granted Patent B2
US 9,328,188 · App. 14/103,415 · Granted May 3, 2016

Method for preparing phenol-formaldehyde resins, resin materials and method for preparing resin molding materials

Inventors: I-Min Tseng (Nantou, TW); Jinn-Jong Wong (Hsinchu, TW); Wen-Chuan Hsu (Hsinchu, TW); Hua-Tang Yue (Zhudong Township, Hsinchu County, TW)
Assignee: Industrial Technology Research Institute
C08G14/04C08G8/04C08G8/08C08G8/24C08J5/24C08K5/05C08L61/06C08L61/12C08L97/02C08J2361/06Y02P30/10
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Quick Facts
Patent No.
US 9,328,188
App. No.
14/103,415
Granted
May 3, 2016
Kind
B2
Abstract

A method for preparing a phenol-formaldehyde resin is provided. The method includes extracting a biomass pyrolysis oil to obtain a first phenolic mixture, mixing the first phenolic mixture, furfural and an alkaline catalyst to proceed to a first polymerization reaction to form a phenol-formaldehyde resin precursor solution, and adding the alkaline catalyst to the phenol-formaldehyde resin precursor solution to proceed to a second polymerization reaction to form a phenol-formaldehyde resin solution. The disclosure also provides a resin material prepared from the phenol-formaldehyde resin. The disclosure further provides a method for preparing a resin molding material.

Claims (18)

1. A method for preparing a phenol-formaldehyde resin, comprising the following steps:

extracting a biomass pyrolysis oil to obtain a first phenolic mixture;

mixing the first phenolic mixture, furfural and an alkaline catalyst to proceed to a first polymerization reaction to form a phenol-formaldehyde resin precursor solution;

adding the alkaline catalyst to the phenol-formaldehyde resin precursor solution to proceed to a second polymerization reaction to form a phenol-formaldehyde resin solution; and

adding an alcohol during the first polymerization reaction, wherein the alcohol and the first phenolic mixture have a weight ratio of 0.25:1-10:1, wherein the alcohol is ethanol, methanol, n-propanol, isopropanol, n-butanol, isobutanol, n-pentanol, n-hexanol or t-butanol.

2. The method for preparing a phenol-formaldehyde resin as claimed in claim 1 , wherein the first phenolic mixture comprises at least two of phenol, 2-cresol, 4-cresol, 3-cresol, guaiacol, 2,6-dimethyl phenol, 2,4-dimethyl phenol, 4-ethyl phenol, m-ethyl phenol, 2-methoxy-4-methyl phenol, 1,2-benzenediol, 3,4-xylenol, 4-ethyl-m-cresol, 3-methoxy catechol, 3-methyl pyrocatechol, 1,4-benzenediol, 4-ethyl guaiacol, 4-methyl catechol, 4-vinyl-2-methoxy phenol, 2-methyl-1,4-benzenediol, 2,6-dimethoxy phenol, 2-methoxy-4-propyl phenol, isoeugenol, 2-methoxy-4-propyl phenol, 2,6-dimethoxy-4-allyl phenol, or 3-allyl-6-methoxy phenol.

3. The method for preparing a phenol-formaldehyde resin as claimed in claim 1 , wherein the biomass pyrolysis oil is extracted by an extractant, and the extractant is ethyl acetate, propyl acetate, butyl acetate, methyl isopropyl ketone, methyl isobutyl ketone, methyl i-amyl ketone, ethyl ethyl ketone- or toluene.

4. The method for preparing a phenol-formaldehyde resin as claimed in claim 3 , wherein the extractant further comprises a second phenolic compound.

5. The method for preparing a phenol-formaldehyde resin as claimed in claim 4 , wherein the second phenolic compound comprises phenol, 2-cresol, 4-cresol, 3-cresol, guaiacol, 2,6-dimethyl phenol, 2,4-dimethyl phenol, 4-ethyl phenol, m-ethyl phenol, 2-methoxy-4-methyl phenol, 1,2-benzenediol, 3,4-xylenol, 4-ethyl-m-cresol, 3-methoxy catechol, 3-methyl pyrocatechol, 1,4-benzenediol, 4-ethyl guaiacol, 4-methyl catechol, 4-vinyl-2-methoxy phenol, 2-methyl-1,4-benzenediol, 2,6-dimethoxy phenol, 2-methoxy-4-propyl phenol, isoeugenol, 2-methoxy-4-propyl phenol, 2,6-dimethoxy-4-allyl phenol, or 3-allyl-6-methoxy phenol, or a combination thereof.

6. The method for preparing a phenol-formaldehyde resin as claimed in claim 4 , wherein the second phenolic compound and the biomass pyrolysis oil have a weight ratio of 0.1:1-1:1.

7. The method for preparing a phenol-formaldehyde resin as claimed in claim 1 , wherein the furfural and the first phenolic mixture have a weight ratio of 0.1:1-4:1.

8. The method for preparing a phenol-formaldehyde resin as claimed in claim 1 , wherein the first polymerization reaction has a reaction temperature greater than or equal to 130° C. and smaller than or equal to 160° C.

9. The method for preparing a phenol-formaldehyde resin as claimed in claim 1 , wherein the second polymerization reaction has a reaction temperature greater than or equal to 70° C. and smaller than 130° C.

10. The method for preparing a phenol-formaldehyde resin as claimed in claim 1 , further comprising diluting the phenol-formaldehyde resin solution to form a phenol-formaldehyde resin diluent.

11. The method for preparing a phenol-formaldehyde resin as claimed in claim 10 , wherein the phenol-formaldehyde resin solution is diluted with a second alcohol.

12. The method for preparing a phenol-formaldehyde resin as claimed in claim 10 , further comprising impregnating a matrix with the phenol-formaldehyde resin diluent to form a resin-impregnated material.

13. The method for preparing a phenol-formaldehyde resin as claimed in claim 12 , further comprising hot-pressing the resin-impregnated material to form a resin molding material.

14. The method for preparing a phenol-formaldehyde resin as claimed in claim 1 , wherein the alcohol and the first phenolic mixture have a weight ratio of 0.25:1-0.6:1.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 18, 2013
From: TSENG, I-MIN; WONG, JINN-JONG; HSU, WEN-CHUAN; YUE, HUA-TANG
To: INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE
Reel/Frame 031847/0459 →
Priority Claims (1)
TW 100149455 A · Dec 29, 2011 · national
Continuity (2)
Continuation In Part 13558027 · Jul 25, 2012
Related Publication 20140100308A1 · Apr 10, 2014