Synthesis and properties of a novel, liquid, trifunctional, cycloaliphatic epoxide

Meiran Xie; Zhonggang Wang; Yunfeng Zhao

doi:10.1002/pola.1259

Synthesis and properties of a novel, liquid, trifunctional, cycloaliphatic epoxide

Meiran Xie
, Zhonggang Wang^*
, Yunfeng Zhao

^*Corresponding author for this work

CAS - Institute of Chemistry

Research output: Contribution to journal › Article › peer-review

57 Scopus citations

Abstract

A novel cycloaliphatic triepoxide, 1,1-bis(2′,3′-epoxycyclohexyloxymethyl)-3,4-epoxycyclohexane (II), and its precursor, 1,1-bis(2′-cyclohexenyloxymethyl)-3-cyclohexene, were synthesized. Their chemical structures were confirmed with IR spectroscopy, elemental analysis, and ¹H NMR spectroscopy. II was easily cured with hexahydro-4-methylphthalic anhydride with 1,3,5-triethylhexahydro-s-triazine as a curing accelerator. The physical properties of the cured product were examined with thermomechanical analysis, thermogravimetric analysis, and dynamic mechanical analysis. Compared with the commercial diepoxide ERL-4221 under the same curing conditions, the cured product based on II showed a much higher glass-transition temperature (198°C), a higher crosslinking density (2.08 × 10^-3 mol/cm³), and a lower coefficient of thermal expansion [6.2 × 10⁵(/°C)]. II may become a promising candidate material for modern microelectronic packaging.

Original language	English
Pages (from-to)	2799-2804
Number of pages	6
Journal	Journal of Polymer Science, Part A: Polymer Chemistry
Volume	39
Issue number	16
DOIs	https://doi.org/10.1002/pola.1259
State	Published - 15 Aug 2001
Externally published	Yes

Keywords

Cycloaliphatic epoxide
Electronic packaging
Mechanical properties
Synthesis
Thermal properties
Thermosets

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10.1002/pola.1259

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title = "Synthesis and properties of a novel, liquid, trifunctional, cycloaliphatic epoxide",

abstract = "A novel cycloaliphatic triepoxide, 1,1-bis(2′,3′-epoxycyclohexyloxymethyl)-3,4-epoxycyclohexane (II), and its precursor, 1,1-bis(2′-cyclohexenyloxymethyl)-3-cyclohexene, were synthesized. Their chemical structures were confirmed with IR spectroscopy, elemental analysis, and 1H NMR spectroscopy. II was easily cured with hexahydro-4-methylphthalic anhydride with 1,3,5-triethylhexahydro-s-triazine as a curing accelerator. The physical properties of the cured product were examined with thermomechanical analysis, thermogravimetric analysis, and dynamic mechanical analysis. Compared with the commercial diepoxide ERL-4221 under the same curing conditions, the cured product based on II showed a much higher glass-transition temperature (198°C), a higher crosslinking density (2.08 × 10-3 mol/cm3), and a lower coefficient of thermal expansion [6.2 × 105(/°C)]. II may become a promising candidate material for modern microelectronic packaging.",

keywords = "Cycloaliphatic epoxide, Electronic packaging, Mechanical properties, Synthesis, Thermal properties, Thermosets",

author = "Meiran Xie and Zhonggang Wang and Yunfeng Zhao",

year = "2001",

month = aug,

day = "15",

doi = "10.1002/pola.1259",

language = "英语",

volume = "39",

pages = "2799--2804",

journal = "Journal of Polymer Science, Part A: Polymer Chemistry",

issn = "0887-624X",

publisher = "John Wiley \& Sons Inc.",

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}

TY - JOUR

T1 - Synthesis and properties of a novel, liquid, trifunctional, cycloaliphatic epoxide

AU - Xie, Meiran

AU - Wang, Zhonggang

AU - Zhao, Yunfeng

PY - 2001/8/15

Y1 - 2001/8/15

N2 - A novel cycloaliphatic triepoxide, 1,1-bis(2′,3′-epoxycyclohexyloxymethyl)-3,4-epoxycyclohexane (II), and its precursor, 1,1-bis(2′-cyclohexenyloxymethyl)-3-cyclohexene, were synthesized. Their chemical structures were confirmed with IR spectroscopy, elemental analysis, and 1H NMR spectroscopy. II was easily cured with hexahydro-4-methylphthalic anhydride with 1,3,5-triethylhexahydro-s-triazine as a curing accelerator. The physical properties of the cured product were examined with thermomechanical analysis, thermogravimetric analysis, and dynamic mechanical analysis. Compared with the commercial diepoxide ERL-4221 under the same curing conditions, the cured product based on II showed a much higher glass-transition temperature (198°C), a higher crosslinking density (2.08 × 10-3 mol/cm3), and a lower coefficient of thermal expansion [6.2 × 105(/°C)]. II may become a promising candidate material for modern microelectronic packaging.

AB - A novel cycloaliphatic triepoxide, 1,1-bis(2′,3′-epoxycyclohexyloxymethyl)-3,4-epoxycyclohexane (II), and its precursor, 1,1-bis(2′-cyclohexenyloxymethyl)-3-cyclohexene, were synthesized. Their chemical structures were confirmed with IR spectroscopy, elemental analysis, and 1H NMR spectroscopy. II was easily cured with hexahydro-4-methylphthalic anhydride with 1,3,5-triethylhexahydro-s-triazine as a curing accelerator. The physical properties of the cured product were examined with thermomechanical analysis, thermogravimetric analysis, and dynamic mechanical analysis. Compared with the commercial diepoxide ERL-4221 under the same curing conditions, the cured product based on II showed a much higher glass-transition temperature (198°C), a higher crosslinking density (2.08 × 10-3 mol/cm3), and a lower coefficient of thermal expansion [6.2 × 105(/°C)]. II may become a promising candidate material for modern microelectronic packaging.

KW - Cycloaliphatic epoxide

KW - Electronic packaging

KW - Mechanical properties

KW - Synthesis

KW - Thermal properties

KW - Thermosets

UR - https://www.scopus.com/pages/publications/0035882379

U2 - 10.1002/pola.1259

DO - 10.1002/pola.1259

M3 - 文章

AN - SCOPUS:0035882379

SN - 0887-624X

VL - 39

SP - 2799

EP - 2804

JO - Journal of Polymer Science, Part A: Polymer Chemistry

JF - Journal of Polymer Science, Part A: Polymer Chemistry

IS - 16

ER -

Synthesis and properties of a novel, liquid, trifunctional, cycloaliphatic epoxide

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Keywords

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