Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From phenol – phenol ether – or inorganic phenolate
Patent
1998-11-03
2000-04-11
Dawson, Robert
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From phenol, phenol ether, or inorganic phenolate
523456, 528103, 5281037, 549555, C08G 5968, C08G 6510
Patent
active
060489561
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a glycidyl ether useful as a reactive diluent for epoxy resins, a composition containing the glycidyl ether, and epoxy resin cured product.
BACKGROUND ART
Epoxy resins demonstrate good adhesion to a variety of materials to be coated, limited contraction upon curing, excellent resistance to heat, chemicals, and solvents, and excellent electrical insulatingproperties and the like. Accordingly, epoxy resins are widely used as coating materials, printing ink, and adhesives.
However, epoxy resins are brittle, and cracks occur due to thermal shock or stress-strain when cured or used.
In order to resolve these problems and to facilitate handling of the epoxy resin, a technique is known in which a diluent is employed in the epoxy resin.
Polyglycidyl ethers of aliphatic polyoyls are known for use as epoxy resin diluents. In general, they have low viscosity, with two or more epoxy groups in the molecule. Specific examples of such polyglycidyl ethers of aliphatic polyols include polyglycidyl ethers of 1,6-hexanediol, neopentylglycol, and trimethylolpropane and the like. In addition, U.S. Pat. No. 4,481,348 discloses *glycidyl ethers derived from 2-butyl-2-ethyl-1,3-propanediol. However, such glycidyl ethers do not impart sufficient flexibility to the epoxy resin, and thus are not satisfactory in terms of their practical applications.
DISCLOSURE OF THE INVENTION
The present invention provides a diglycidyl ether represented by the following general formula (I): ##STR2## (wherein, R.sup.1 and R.sup.2 are the same or different, and represent lower alkyl having 1.about.6 carbon atoms), and provides a reactive diluent for an epoxy resin containing a diglycidyl ether represented by the above general formula (I).
The present invention also provides a composition containing an epoxy resin and the diglycidyl ether represented by the above general formula (I), and an epoxy resin cured product obtained by adding a curing agent to the composition and curing the composition.
In addition, the present invention also provides a method for curing an epoxy resin in which the aforementioned diglycidyl ether is mixed with an epoxy resin, a curing agent is added to the mixture, and the mixture is cured.
MODES FOR CARRYING OUT THE INVENTION
In the definition for the general formula (I) in the present invention, R.sup.1 and R.sup.2 are lower alkyl having 1.about.6 carbon atoms and are either a linear or branched chain. Examples include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, isopentyl, neopentyl, hexyl and the like.
Diglycidyl ether of the present invention represented by general formula (I) can be obtained by reacting epihalohydrin and 2,4-dialkyl-1,5-pentanediol having R.sup.1 and R.sup.2 at positions 2 and 4 in a two-phase system of an organic solvent phase and a solid phase in the presence of a solid alkali and a phase transfer catalyst [see Synthesis, p. 649 (1985), for example].
Specific examples of 2,4-dialkyl-1,5-pentanediol which is one of the starting materials the diglycidyl ether of the present invention represented by general formula (I) include 2,4-dimethyl-1,5-pentanediol, 2-ethyl-4-methyl-1,5-pentanediol, 2-methyl-4-propyl-1,5-pentanediol, 2-isopropyl-4-methyl-1,5-pentanediol, 2,4-diethyl-1,5-pentanediol, 2-ethyl-4-propyl-1,5-pentanediol, 2-ethyl-4-isopropyl-1,5-pentanediol, 2,4-dipropyl-1,5-pentanediol, 2-isopropyl-4-propyl-1,5-pentanediol, 2,4-diisopropyl-1,5-pentanediol, 2,4-dibutyl-1,5-pentanediol, 2,4-dipentyl-1,5-pentanediol, 2,4-dihexyl-1,5-pentanediol and the like.
These 2,4-dialkyl-1,5-pentanediols can be produced using a known method. Preferably, 2,4-dialkyl-1,5-pentanediols are produced by reacting formaldehyde with 2-butenal derivative represented by general formula (III) (step 1), and then hydrogenating a mixture of the thus obtained reaction products (IV) and (V) (step 2) as disclosed in Japanese Published Unexamined Patent Application No. 48642/96 or in EP807617A. ##STR3##
A 2-butenal derivative represented by general for
REFERENCES:
patent: 4417033 (1983-11-01), Bowditch
Murayama Toshikazu
Muto Kenji
Tsuzaki Nobuko
Aylward D.
Dawson Robert
Kyowa Yuka Co., Ltd.
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