Stock material or miscellaneous articles – Composite – Of epoxy ether
Reexamination Certificate
2002-01-04
2003-09-09
Dawson, Robert (Department: 1712)
Stock material or miscellaneous articles
Composite
Of epoxy ether
C252S601000, C252S609000, C525S482000, C525S490000, C528S116000, C528S118000, C528S163000
Reexamination Certificate
active
06617029
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a nitrogen-containing flame retarding epoxy resin and their composition comprising the nitrogen-containing flame retarding epoxy resin.
BACKGROUND OF THE INVENTION
Under the consideration of economics and productivity, an encapsulating material for currently semiconductor devices is an epoxy-based resin composition. To insure the use safety. electronic parts for the semiconductor are required to meet a flame retarding specification regulated by the UL. The approach to attain the flame retarding specification is addition of halogen-containing epoxy resin and diantimony trioxide as a flame retarding assistant into epoxy resin compositions for encapsulating electronic parts. However it is known that such flame retarding assistants are harmful to human and animal. For example. Diantimony trioxide has been classified a cancerous material while an epoxy resin containing halogen such as bromine will produce corrosive bromine free radical and hydrogen bromide during burning. Also, an aryl compound containing high content bromine will produce toxic brominated furanes and brominated dioxins compounds. Such toxic material have adverse effects to human, animal and environment. Thus, it is eagerly required to semiconductor manufacture for developing a novel epoxy resin without halogen neither diantimony trioxide to resolve the problems associated with the use of halogen-containing epoxy resin and diantimony trioxide.
For flame retarding resins, a nitrogen-containing compound is widely used as a new generation flame retarding agent. Among others, examples of commonly used flame retarding agents include non-reactive type nitrogen-containing compounds such as melamine, and triazine-containing cyanate, and non-reactive phosphorus-containing compounds such as red phosphorus, triphenyl phosphate (TPP), tricresyl phosphate (TCP), and poly(ammonium phosphate), and non-reactive nitrogen-containing flame retarding agent such as melamine dimer and trimer. To attain desired flame retarding effect is required to incorporating such non-reactive flame retarding agent in a large amount to epoxy resin composition formulations, which will cause the lowing of relative amount of the epoxy resin and the curing agent contained in the formulation so that the performances of the epoxy formulation will decrease.
Recently, under the considerations of environmental protection and safety, a reactive type resin flame retarding agent is used to substitute for currently used flame retarding agent. Since reactive nitrogen-containing flame retarding resin can react with other components and has better heat stability, it is widely used to substitute for halogen-containing resin. For example, Japan Unexamined Patent Publication No. 2000-297284 discloses a reactive type nitrogen-containing flame retarding agent which is a product from reacting a triazine compound and formaldehyde. Japan Examined Patent Publication No. Hei 6-31276 discloses a phosphorous-containing organic cyclic compound as a flame retarding agent. In addition, EP 0877040A1 discloses a novolac phenolic resin composition containing triazine ring possessing a flame retarding property. Such reactive type nitrogen-containing compounds have widely been used as a flame retarding agent in resin composition to be required a flame retarding property for electronic parts. Currently, the development of such reactive type nitrogen-containing flame retarding resin is mainly novolac-based resin, but for semiconductor encapsulating, such a novolac-based resin composition can not improve a flame retarding property of the resin composition due to its low addition proportion.
To overcome the disadvantages associated with the current semiconductor encapsulating technique, the present inventors have investigated on epoxy resin and then developed a modified nitrogen-containing epoxy resin. Thus the present invention is completed.
The nitrogen-containing epoxy resin of the present invention has excellent flame retardant effect and heat resistance, it is therefore useful as an encapsulating material or semiconductor and imparts the encapsulated article with excellent flame retardant effect and heat resistance. Further, the nitrogen-containing epoxy resin of the present invention is also useful as a flame retarding agent or stabilizer for resin other than epoxy resin, such as thermoset and thermoplastic resin and is useful for producing various electronic products.
DETAILED DESCRIPTION OF THE PRESENT INVENTION
The present invention relates to a nitrogen-containing epoxy resin of the following formula:
wherein R's are the same or different and each represents a hydrogen atom or —R
13
—C
6-10
aryl-(OR
14
)
p
, and the aryl group is optionally substituted with C
1-6
alkyl group, in which R
13
represents a C
1-6
alkylene group or a phenylene —CH
2
— group optionally substituted with a hydroxy group, R
14
represents a glycidyl group, and p is an integer of 1 or 2, provided that at least one R group is not a hydrogen atom; R
1
represents a phenyl group or —N(R)
2
group in which R is defined as above;
which is produced from reacting melamine derivatives sequential with aldehydes, phenolic compound and epihalohydrin.
The present invention also relates to a flame retarding epoxy resin composition comprising the nitrogen-containing epoxy resin of the present invention.
The present invention further relates to a flame retarding epoxy resin composition comprising the nitrogen-containing epoxy resin of the present invention and a phosphorous-containing, flame retarding agent:
wherein R
1
represents —O—, —NiH
2
—, —S—, —COO—, —SO
2
—, —CO—, CH
2
CON<; Ar represents a phenylene group, a biphenylene group, a bisphenol divalent group, a polyphenol divalent group, a divalent group selected from the following formulae:
wherein R
2
represents a hydrogen atom, a C
1-6
alkyl or C
1-6
aryl;
R
3
represents —OH, —NH
2
, —SH, —COOH, —SO
3
H, —CHO, —NHCOCH
3
;
R
4
represents —CH
2
—, —(CH
3
)
3
C—, —SO
2
—, —CO—, —O—;
m represents an integer of 0 to 2, and n represents an integer of 1 to 20.
Furthermore, the present invention also relates to the use of the present nitrogen-containing epoxy resin as a flame retarding agent or stabilizer for resin material other than epoxy resin which is in turn useful for producing various electronic products.
The term “C
1-6
alkyl group” used herein means a liner or branched alkyl group having 1 to 6 carbon atoms such as methyl, ethyl, n-propyl, isopropyl, n-butyl, s-butyl, t-butyl, n-pentyl, isopentyl, n-hexyl and isohexyl and the like. The term “C
1-6
alkylene group” used herein means a residue obtained by subtracting two hydrogens atom from a linear or branched alkane having 1 to 6 carbon atoms.
The term “C
1-6
aryl group” used herein means an aryl group having from 6 to 12 carbon atoms, such as phenyl group, naphthyl group, and biphenyl group and the like.
The term “arylene group” used herein means a residue obtained by subtracting two hydrogens atom from an aromatic hydrocarbon.
The term “C
1-6
aryl group” used herein means an aryl group having from 6 to 12 carbon atoms, such as phenyl group, naphthyl group, and the like.
The flame retarding nitrogen-containing epoxy resin according to the present invention is prepared from reacting melamine derivatives sequential with aldehydes of formula R
12
COH, functional-containing benzene compound and epihalohydrin. Thus, the present invention also relates to a process for producing a flame retarding nitrogen-containing epoxy resin, the process comprises:
(a) reacting melamine derivatives of following formula (2):
(in which R
5
represents —NH, or a phenyl group), with aldehydes of formula R
12
COH (in which R
12
represents C
1-6
alkyl group or unsubstituted or hydroxy-substituted phenyl group) in a suitable reaction solvent at a temperature of from 40 to 150° C., preferably at a temperature of from 60 to 100° C., to give a hydroxy-containing triazine derivative containing a functional group of the formula —NHCR
12
HOH; and
(b) dehydrat
Chao Huan-Chang
Chen Chih-Fu
Chen Hong-Hsing
Hwang Kuen-Yuan
Bacon & Thomas
Chang Chun Plastics Co. Ltd.
Dawson Robert
Feely Michael J.
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