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- Nachgewiesen in: USPTO Patent Grants
- Sprachen: English
- Patent Number: 11787,904
- Publication Date: October 17, 2023
- Appl. No: 17/112757
- Application Filed: December 04, 2020
- Assignees: CPC CORPORATION, TAIWAN (Kaohsiung, TW)
- Claim: 1. A phosphinated (2,6-dimethylphenyl ether) oligomer, having a structure represented by Formula (1): [chemical expression included] wherein X is a single bond, —CH 2 —, —O—, —C(CH 3) 2 — or [chemical expression included] R′ 0 , R 0 , R 1 , R 2 and R 3 are independently hydrogen, C1-C6 alkyl or phenyl, n and m are independently an integer from 1 to 300, p and q are independently an integer from 1 to 4, Y is [chemical expression included] and U is a methylene group.
- Claim: 2. A preparation method for the phosphinated (2,6-dimethylphenyl ether) oligomer having a structure represented by Formula (1) of claim 1 , comprising: reacting a phenolic terminal (2,6-dimethylphenyl ether) oligomer represented by Formula (2) with a phenone compound or a benzaldehyde compound represented by Formula (3) under a catalysis of an alkaline catalyst to obtain a bifunctional (2,6-dimethylphenyl ether) oligomer represented by Formula (4); reacting the bifunctional (2,6-dimethylphenyl ether) oligomer, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide with phenol containing R 3 represented by Formula (5) under the catalysis of an acid catalyst to obtain a phosphinated bisphenol (2,6-dimethylphenyl ether) oligomer represented by Formula (6); reacting the phosphinated bisphenol (2,6-dimethylphenyl ether) oligomer with methyl acrylic anhydride under the catalysis of a nitrogen-containing or alkaline catalyst, or reacting the phosphinated bisphenol (2,6-dimethylphenyl ether) oligomer with 3-vinylbenzyl chloride, 4-vinylbenzyl chloride or a combination thereof under the catalysis of the alkaline catalyst to obtain the phosphinated (2,6-dimethylphenyl ether) oligomer, [chemical expression included] wherein X is a single bond, —CH 2 —, —O—, —C(CH 3) 2 — or [chemical expression included] R′ 0 , R 0 , R 1 , R 2 or R 3 are independently hydrogen, C1-C6 alkyl or phenyl, Z is fluorine or chlorine, n and m are independently an integer from 1 to 300, p and q are independently an integer from 1 to 4.
- Claim: 3. The preparation method for the phosphinated (2,6-dimethylphenyl ether) oligomer according to claim 2 , wherein the phenone compound comprises 4-fluoroacetophenone and 4-chloroacetophenone; the benzaldehyde compound comprises 4-fluorobenzaldehyde and 4-chlorobenzaldehyde; the bifunctional (2,6-dimethylphenyl ether) oligomer comprises (2,6-dimethylphenyl ether) oligomer containing a diketone structure or (2,6-dimethylphenyl ether) oligomer containing a dialdehyde structure, wherein the (2,6-dimethylphenyl ether) oligomer containing the diketone structure is a compound when R 2 in the Formula (4) is a methyl group, and the (2,6-dimethylphenyl ether) oligomer containing the dialdehyde structure is a compound when R 2 in the Formula (4) is hydrogen.
- Claim: 4. The preparation method for the phosphinated (2,6-dimethylphenyl ether) oligomer according to claim 2 , wherein the alkaline catalyst comprises potassium carbonate, sodium carbonate, potassium hydroxide, sodium hydroxide, sodium bicarbonate, sodium acetate, or a combination thereof.
- Claim: 5. The preparation method for the phosphinated (2,6-dimethylphenyl ether) oligomer according to claim 2 , wherein the acid catalyst comprises hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, methanesulfonic acid, methylbenzenesulfonic acid, or a combination thereof.
- Claim: 6. The preparation method for the phosphinated (2,6-dimethylphenyl ether) oligomer according to claim 2 , wherein the nitrogen-containing catalyst comprises 4-dimethylaminopyridine, pyridine, imidazole, dimethylimidazole, or a combination thereof.
- Claim: 7. A cured product, which is obtained by curing a mixture of the phosphinated (2,6-dimethylphenyl ether) oligomer as defined in claim 1 and a catalyst by heating.
- Claim: 8. The cured product according to claim 7 , wherein the catalyst comprises benzoyl peroxide, tert-butyl cumene peroxide, or a combination thereof.
- Claim: 9. The cured product according to claim 7 , wherein the content of the catalyst is 0.1% to 1.0% by weight based on the total weight of the phosphinated (2,6-dimethylphenyl ether) oligomer.
- Claim: 10. A cured product, which is obtained by mixing the phosphinated (2,6-dimethylphenyl ether) oligomer as defined in claim 6 with an epoxy resin, followed by copolymerizing under a catalyst by heating, wherein the catalyst comprises an epoxy resin ring open agent and a double bond initiator.
- Claim: 11. The cured product according to claim 10 , wherein the epoxy resin ring open agent comprises 4-dimethylaminopyridine, pyridine, imidazole, dimethylimidazole, or a combination thereof.
- Claim: 12. The cured product according to claim 10 , wherein the content of the epoxy resin ring open agent is 0.5% to 2.0% by weight based on the total weight of the epoxy resin.
- Claim: 13. The cured product according to claim 10 , wherein the double bond initiator comprises benzoyl peroxide, tert-butyl cumene peroxide, di-tert-butyl peroxide, or a combination thereof.
- Claim: 14. The cured product according to claim 10 , wherein the content of the double bond initiator is 0.1% to 1.0% by weight based on the total weight of the phosphinated (2,6-dimethylphenyl ether) oligomer.
- Claim: 15. A method of using the phosphinated (2,6-dimethylphenyl ether) oligomer as defined in claim 1 , comprising providing the phosphinated (2,6-dimethylphenyl ether) oligomer as a material for making a base board, a copper clad laminate or a printed circuit board.
- Patent References Cited: 6627704 September 2003 Yeager et al. ; 6995195 February 2006 Ishii et al. ; 8822723 September 2014 Su ; 20130012668 January 2013 Lin ; 20170088669 March 2017 Hsieh et al. ; 201502133 January 2015 ; I537281 June 2016
- Other References: Lin, C.H. et al., “Novel phosphorus-containing epoxy resins Part I. Synthesis and properties”, Polymer, vol. 42, Issue 5, Mar. 2001, pp. 1869-1878. cited by applicant ; Hwang, Hann-Jang, et al., “Synthesis and properties of bismaleimide resin containing dicyclopentadiene or dipentene. VI”, Polymer Internatonal, vol. 55, Issue 11, Nov. 2006, pp. 1341-1349. cited by applicant ; Hwang, Hann-Jang, et al., “Flame Retardancy and Dielectric Properties of Dicyclopentadiene-Based Benzoxazine Cured with a Phosphorus-Containing Phenolic Resin”, Journal of Applied Polymer Science, Nov. 15, 2008, vol. 110, Issue 4, pp. 2413-2423. cited by applicant
- Primary Examiner: Yoon, Tae H
- Attorney, Agent or Firm: Muncy, Geissler, Olds & Lowe, P.C.
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