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Phosphorus-containing flame-retardant hardeners, epoxy resins, advanced epoxy resins and cured epoxy resins

a flame-retardant hardener and phosphorus technology, which is applied in the direction of printed circuits, circuit susbtrate materials, electrical equipment, etc., can solve the problems of not meeting safety requirements, generating toxic and corrosive fumes, etc., and achieves high glass transition temperature (tg), high decomposition temperature, and high elastic modulus

Inactive Publication Date: 2005-01-06
CHUN SHAN WANG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention also provides a cured flame-retardant epoxy resin by using the hardener of the present invention and a cured flame-retardant epoxy resin from the flame-retardant epoxy resin of the present invention. The cured flame-retardant epoxy resins so prepared have a high glass transition temperature (Tg), high decomposition temperature and high elastic modulus, and are free of toxic and corrosive fumes during combustion, and thus are suitable for printed circuit board and semiconductor encapsulation applications.

Problems solved by technology

The advanced epoxy resins and cured epoxy resins prepared with these hardeners do not have flame retardancy, and thus can not meet the safety requirements.
Although the tetrabromobisphenol A-containing advanced epoxy resin shows flame retardant property, major problems encountered with this system are concerned with the generation of toxic and corrosive fumes during combustion such as dioxin and benzofuran.

Method used

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  • Phosphorus-containing flame-retardant hardeners, epoxy resins, advanced epoxy resins and cured epoxy resins
  • Phosphorus-containing flame-retardant hardeners, epoxy resins, advanced epoxy resins and cured epoxy resins
  • Phosphorus-containing flame-retardant hardeners, epoxy resins, advanced epoxy resins and cured epoxy resins

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1 -

Preparation Example 1-A (P-1-A, ODOPM-BPA-A):

To an one liter four-inlet flask equipped with a thermocouple and temperature controller, a reflux condenser, a nitrogen feed and a mechanical stirrer, 1 mole (228 g) bisphenol-A (BPA) was added, heated to 170° C. and then stirred to a molten state. 0.7 g (0.3 wt %) potassium acetate was mixed with the molten BPA followed by adding slowly 1 mole (246 g) 2-(6-oxid-6H-dibenz<c,e><1,2>oxa-phosphorin-6-yl) methanol (ODOPM). The mixture was heated gradually to a temperature of 220° C. when the addition of ODOPM was completed. The substitution reaction was continued for 6 hours. The reaction product was dissolved in cyclohexanone, and washed with water several times before the solvent was evaporated under vacuum to obtain ODOPM-BPA-A (P-1-A). Yield, 98%; softening temperature, 125-132° C. Phosphorus content: 6.79%.

preparation example 1-b (

P-1-B, ODOPM-BPA-A):

To an one liter four-inlet flask equipped with a thermocouple and temperature controller, a reflux condenser, a nitrogen feed and a mechanical stirrer, 1 mole (228 9) bisphenol-A (BPA) was added, heated to 170° C. and then stirred to a molten state. 1.14 g (0.5 wt %) potassium acetate was mixed with the molten BPA followed by adding slowly 1.5 mole (369 g) ODOPM. The mixture was heated gradually to a temperature of 220° C. when the addition of ODOPM was completed. The substitution reaction was continued for 8 hours. The reaction product was dissolved in cyclohexanone, and washed with water several times before the solvent was evaporated under vacuum to obtain ODOPM-BPA-B (P-1-B). Yield, 96%; softening temperature, 136-140° C. Phosphorus content: 8.16%.

preparation example 1-c (

P-1-C, ODOPM-BPA-A):

To an one liter four-inlet flask equipped with a thermocouple and temperature controller, a reflux condenser, a nitrogen feed and a mechanical stirrer, 1 mole (228 g) bisphenol-A (BPA) was added, heated to 170° C. and then stirred to a molten state. 1.14 g (0.5 wt %) potassium acetate was mixed with the molten BPA followed by adding slowly 2 mole (492 g) ODOPM. The mixture was heated gradually to a temperature of 220° C. when the addition of ODOPM was completed. The substitution reaction was continued for 10 hours. The reaction product was dissolved in cyclohexanone, and washed with water several times before the solvent was evaporated under vacuum to obtain ODOPM-BPA-C (P-1-C). Yield, 92%; softening temperature, 143-148° C. Phosphorus content: 9.06%.

Preparation Example 2 (P-2, DPOM-BPA):

To an one liter four-inlet flask equipped with a thermocouple and temperature controller, a reflux condenser, a nitrogen feed and a mechanical stirrer, 1 mole (228 g) bisphe...

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Abstract

The present invention discloses an active-hydrogen-containing phosphorus compound for cross-linking a resin and for imparting flame-retardancy to the cured resin, and in particular to a cured frame-retardant epoxy resin prepared by reacting the hardener with a di- or poly-functional epoxy resin via an addition reaction between the active hydrogen and the epoxide group. The present invention also discloses an epoxy resin made from the active-hydrogen-containing phosphorus compound and epihalohydrin.

Description

FIELD OF THE INVENTION The present invention relates generally to an active-hydrogen-containing phosphorus compound for cross-linking a resin and for imparting flame-retardancy to the cured resin, and in particular to a cured frame-retardant epoxy resin prepared by reacting the hardener with a di- or poly-functional epoxy resin via an addition reaction between the active hydrogen and the epoxide group. It also relates to an epoxy resin made from the active-hydrogen-containing phosphorus compound and epihalohydrin. BACKGROUND OF THE INVENTION Typical hardeners for epoxy resins and advanced epoxy resins are phenol-formaldehyde novolac resin, dicyandiamide, methylenedianiline, diaminodiphenyl sulfone, phthalic anhydride, and hexahydrophthalic anhydride, etc. The advanced epoxy resins and cured epoxy resins prepared with these hardeners do not have flame retardancy, and thus can not meet the safety requirements. Several approaches for modification of epoxy backbone for enhancing the ...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C08G59/10C08G59/20C08G59/40C08G59/50C08G59/62C08L63/00H05K1/03
CPCC08G59/4021H05K1/0326C08G59/621C08G59/504
Inventor WANG, CHUN-SHANSHIEH, JENG-YUEHLIN, CHING HSUAN
Owner CHUN SHAN WANG