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Diglycidyl Ethers

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Diglycidyl Ethers Europaisches Patentamt (19) J European Patent Office Office europeen des brevets (11) EP0 911 326 A1 (12) EUROPEAN PATENT APPLICATION published in accordance with Art. 158(3) EPC (43) Date of publication: (51) Int. CI.6: C07D 303/27, C08G 59/04 28.04.1999 Bulletin 1999/17 (86) International application number: (21) Application number: 98905732.8 PCT/JP98/00861 (22) Date of filing: 03.03.1998 (87) International publication number: WO 98/3931 4 (1 1 .09.1 998 Gazette 1 998/36) (84) Designated Contracting States: • MURAYAMA, Toshikazu AT BE CH DE DK ES Fl FR GB GR IE IT LI LU MC Yokkaichi-shi, Mie 51 2-091 1 (JP) NL PT SE • TSUZAKI, Nobuko Yokkaichi-shi, Mie 51 2-091 1 (JP) (30) Priority: 04.03.1997 J P 48632/97 (74) Representative: (71 ) Applicant: Kyowa Yuka Co., Ltd. Le Guen, Gerard et al Tokyo 1 00-0004 (JP) CABINET LAVOIX 2, place d'Estienne d'Orves (72) Inventors: 75441 Paris Cedex 09 (FR) • MUTO, Kenji Yokkaichi-shi, Mie551 2-091 1 (JP) (54) DIGLYCIDYL ETHERS (57) The present invention relates to a diglycidyl ether represented by the following general formula (I): R' CH?-CH-CH2-0-CH2-CH-CH2-CH-CH2-O— CH2-CH-CH2 \/ v O 0 (I) (wherein, R1 and R2 are the same or different, and represent lower alkyl having 1-6 carbon atoms), a composition including the glycidyl ether and epoxy resin, and epoxy resin cured product obtained by the composition. The glycidyl ether can be used as a reactive diluent for epoxy resins. CO CM CO <7> o Q_ LU Printed by Xerox (UK) Business Services 2.16.7/3.6 EP0 911 326 A1 Description TECHNICAL FIELD 5 [0001] 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 10 [0002] Epoxy resins demonstrate good adhesion to a variety of materials to be coated, limited contraction upon cur- ing, excellent resistance to heat, chemicals, and solvents, and excellent electrical insulating properties and the like. Accordingly, epoxy resins are widely used as coating materials, printing ink, and adhesives. [0003] However, epoxy resins are brittle, and cracks occur due to thermal shock or stress-strain when cured or used. [0004] In order to resolve these problems and to facilitate handling of the epoxy resin, a technique is known in which 15 a diluent is employed in the epoxy resin. [0005] 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 poly- ols include polyglycidyl ethers of 1,6-hexanediol, neopentylglycol, and trimethylolpropane and the like. In addition, US Patent No. 4,481,348 discloses glycidyl ethers derived from 2-butyl-2-ethyl-1,3-propanediol. However, such glycidyl 20 ethers do not impart sufficient flexibility to the epoxy resin, and thus are not satisfactory in terms of their practical appli- cations. DISCLOSURE OF THE INVENTION 25 [0006] The present invention provides a diglycidyl ether represented by the following general formula (I): R R' I I 30 CH2 CH2 ' -0-CH2-CH-CH2-CH- CH2-0— CH2-CH-CH2 \/ O (I) (wherein, R1 and R2 are the same or different, and represent lower alkyl having 1-6 carbon atoms), and provides a reactive diluent for an epoxy resin containing a diglycidyl ether represented by the above general formula (I). [0007] The present invention also provides a composition containing an epoxy resin and the diglycidyl ether repre- sented by the above general formula (I), and an epoxy resin cured product obtained by adding a curing agent to the 40 composition and curing the composition. [0008] 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 45 [0009] In the definition for the general formula (I) in the present invention, R1 and R2 are lower alkyl having 1 -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. [0010] Diglycidyl ether of the present invention represented by general formula (I) can be obtained by reacting epi- 50 halohydrin and 2,4-dialkyl-1 ,5-pentanediol having R1 and R2 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]. [0011] 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- 55 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. 2 EP0 911 326 A1 [0012] These 2,4-dialkyl-1,5-pentanediols can be produced using a known method. Preferably, 2,4-dialkyl-1 ,5-pen- tanediols 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. 5 step 1 R1CH2CH=CR2CHO + HCHO - (ill) 10 step 2 HOCH2CHR1CH=CR2CHO (V) HOCH2CHR1CH2CHR2CH2OH (ii) 25 [0013] A 2-butenal derivative represented by general formula (III) is obtained by aldol condensation of one or two types of aldehydes and dehydration reaction. 30 [0014] In step 1, reaction between formaldehyde and a 2-butenal derivative represented by general formula (III) is carried out using a basic catalyst preferably in the presence of a water soluble organic solvent at 15~100°C, preferably at 30~80°C. The molar ratio of formaldehyde based on the butenal derivative is in the range of 0.4-2, and preferably in the range of 0.5-1.5. [0015] Examples of the basic catalyst employed in step 1 include such alkaline metal hydroxides such as lithium 35 hydroxide, sodium hydroxide, and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; sodium alcohola- tes such as sodium methylate, sodium ethylate, and sodium butylate; tertiary amines such as triethylamine and trib- utylamine; quaternary ammonium hydroxides such as benzyltrimethylammonium hydroxide and tetrabutylammonium hydroxide; and strong basic ion-exchange resins. The catalyst is employed in an amount such that its molar ratio based 40 on the 2,4-diethyl-1 ,5-pentanediol is 0.01-0.5, and preferably 0.02-0.3. [0016] The water soluble organic solvent employed in step 1 is not particularly limited, provided that it is inert under the reaction conditions. For example, alcohols such as methanol, ethanol, propanol, isopropyl alcohol, ethylene glycol, and propylene glycol; ethers such as dimethoxyethane, tetrahydrofuran, and dioxane; and glycol ethers such as ethyl- ene glycol monoethyl ether may be suitably employed. The amount of the water soluble organic solvent employed is not 45 particularly limited, but is preferably 1 00% by weight or less of the total amount of the 2-butenal derivative and formalin employed. [001 7] Impurities are removed from the mixture of compound (IV) and compound (V) obtained in step 1 , preferably by a usual method such as neutralizing, concentrating, separating or washing with water. A mixture of compound (IV) and compound (V) obtained in step 1 is then subjected to hydrogenation reaction by dispersing or suspending a hydrogen- 50 ation catalyst in a suitable solvent or without-solvent, in the presence of hydrogen, or by supplying a solution of the mix- ture of compound (IV) and compound (V) obtained in step 1 to a reaction tube filled with the hydrogenation catalyst. The hydrogenation reaction is carried out at 30~200°C, and preferably 50~150°C, at a hydrogen pressure of 1-150 kg/cm2, and preferably 5-80 kg/cm2 (step 2). [0018] The solvent employed in step 2 is not particularly limited provided that it is inert wider the reaction conditions. 55 Suitable examples thereof include various alcohols such as methanol, ethanol, propanol, isopropyl alcohol, and buta- nol; ethers such as dimethoxyethane, tetrahydrofuran, and dioxane; water; or mixed solvents thereof. Examples of hydrogenation catalysts include those containing one or more of metals such as nickel, ruthenium, platinum, copper, or rhodium, as the catalytic active component. They may further include metals such as chrome, zinc, barium, aluminum, 3 EP0 911 326 A1 magnesium, tungsten or the like. After completion of the reaction, the target 2,4-dialkyl-1 ,5-pentanediol can be obtained from the reaction mixture by a usual method, for example, distilling off low boiling point compounds from the reaction mixture at normal or reduced pressure after the catalyst has been removed, and then purifying the obtained residue by distillation under reduced pressure. 5 [001 9] Specific examples of the epihalohydrin which is reacted with 2,4-dialkyl-1 ,5-pentanediol in order to obtain the diglycidyl ether of the present invention include epichlorohydrin, epibromohydrin, epiiodohydrin and the like.
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