JPH10130352A - Production of novolak type compound - Google Patents
Production of novolak type compoundInfo
- Publication number
- JPH10130352A JPH10130352A JP30088196A JP30088196A JPH10130352A JP H10130352 A JPH10130352 A JP H10130352A JP 30088196 A JP30088196 A JP 30088196A JP 30088196 A JP30088196 A JP 30088196A JP H10130352 A JPH10130352 A JP H10130352A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- aromatic
- reaction
- bis
- novolak type
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 22
- 229920003986 novolac Polymers 0.000 title claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- -1 aromatic hydroxyl compound Chemical class 0.000 claims abstract description 16
- 239000000126 substance Substances 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 22
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 3
- 229920005989 resin Polymers 0.000 abstract description 3
- 239000011347 resin Substances 0.000 abstract description 3
- ZZHIDJWUJRKHGX-UHFFFAOYSA-N 1,4-bis(chloromethyl)benzene Chemical compound ClCC1=CC=C(CCl)C=C1 ZZHIDJWUJRKHGX-UHFFFAOYSA-N 0.000 abstract description 2
- 238000005260 corrosion Methods 0.000 abstract description 2
- 230000007797 corrosion Effects 0.000 abstract description 2
- 238000001879 gelation Methods 0.000 abstract description 2
- 150000004820 halides Chemical group 0.000 abstract description 2
- 230000001588 bifunctional effect Effects 0.000 abstract 1
- 150000004780 naphthols Chemical class 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 239000012433 hydrogen halide Substances 0.000 description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- INZDTEICWPZYJM-UHFFFAOYSA-N 1-(chloromethyl)-4-[4-(chloromethyl)phenyl]benzene Chemical group C1=CC(CCl)=CC=C1C1=CC=C(CCl)C=C1 INZDTEICWPZYJM-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- FMGGHNGKHRCJLL-UHFFFAOYSA-N 1,2-bis(chloromethyl)benzene Chemical compound ClCC1=CC=CC=C1CCl FMGGHNGKHRCJLL-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- GRJWOKACBGZOKT-UHFFFAOYSA-N 1,3-bis(chloromethyl)benzene Chemical compound ClCC1=CC=CC(CCl)=C1 GRJWOKACBGZOKT-UHFFFAOYSA-N 0.000 description 1
- RBZMSGOBSOCYHR-UHFFFAOYSA-N 1,4-bis(bromomethyl)benzene Chemical compound BrCC1=CC=C(CBr)C=C1 RBZMSGOBSOCYHR-UHFFFAOYSA-N 0.000 description 1
- PMIHHEJEQAQZET-UHFFFAOYSA-N 1,4-bis(chloromethyl)naphthalene Chemical compound C1=CC=C2C(CCl)=CC=C(CCl)C2=C1 PMIHHEJEQAQZET-UHFFFAOYSA-N 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 1
- VDXGURZGBXUKES-UHFFFAOYSA-N 1-(bromomethyl)-2-[2-(bromomethyl)phenyl]benzene Chemical group BrCC1=CC=CC=C1C1=CC=CC=C1CBr VDXGURZGBXUKES-UHFFFAOYSA-N 0.000 description 1
- RPCGCPIVUNQAJV-UHFFFAOYSA-N 1-(bromomethyl)-2-[4-(bromomethyl)phenyl]benzene Chemical group C1=CC(CBr)=CC=C1C1=CC=CC=C1CBr RPCGCPIVUNQAJV-UHFFFAOYSA-N 0.000 description 1
- HMUGRILXVBKBID-UHFFFAOYSA-N 1-(bromomethyl)-4-[4-(bromomethyl)phenyl]benzene Chemical group C1=CC(CBr)=CC=C1C1=CC=C(CBr)C=C1 HMUGRILXVBKBID-UHFFFAOYSA-N 0.000 description 1
- FVRWZGLTJFGUJF-UHFFFAOYSA-N 1-(chloromethyl)-2-[2-(chloromethyl)phenyl]benzene Chemical group ClCC1=CC=CC=C1C1=CC=CC=C1CCl FVRWZGLTJFGUJF-UHFFFAOYSA-N 0.000 description 1
- XEIQYEHVSAUFIB-UHFFFAOYSA-N 1-(chloromethyl)-2-[4-(chloromethyl)phenyl]benzene Chemical group C1=CC(CCl)=CC=C1C1=CC=CC=C1CCl XEIQYEHVSAUFIB-UHFFFAOYSA-N 0.000 description 1
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 1
- RGAMXQRIMZYOPM-UHFFFAOYSA-N 2,6-bis(chloromethyl)naphthalene Chemical compound C1=C(CCl)C=CC2=CC(CCl)=CC=C21 RGAMXQRIMZYOPM-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- VHMSJKVLIFLUDG-UHFFFAOYSA-N BrC(C=CC=C1)=C1C(C=CC1=CC=CC=C11)=C1C(C=CC=C1)=C1Br Chemical class BrC(C=CC=C1)=C1C(C=CC1=CC=CC=C11)=C1C(C=CC=C1)=C1Br VHMSJKVLIFLUDG-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 229940106691 bisphenol a Drugs 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 235000012255 calcium oxide Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 235000012245 magnesium oxide Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明はノボラック型化合物
の製造法に関する。[0001] The present invention relates to a method for producing a novolak type compound.
【０００２】[0002]
【従来の技術】特開平４−１１０３１７には、ハロゲン
化メチル芳香族化合物と芳香族ヒドロキシ化合物の反応
により、目的とするノボラックが製造できることが記載
されている。しかし同時に、ハロゲン化水素ガスの発生
等の問題があることも記載されている。また、この反応
は、原理的に、酸触媒であるハロゲン化水素が発生し、
加速度的に反応速度が増加するため反応のコントロ−ル
が難しいという問題があった。2. Description of the Related Art Japanese Patent Application Laid-Open No. 4-110317 discloses that a desired novolak can be produced by reacting a halogenated methyl aromatic compound with an aromatic hydroxy compound. However, it also describes that there is a problem such as generation of hydrogen halide gas. In addition, this reaction generates, in principle, hydrogen halide which is an acid catalyst,
There is a problem that the control of the reaction is difficult because the reaction speed increases at an accelerated rate.
【０００３】[0003]
【発明が解決しようとする課題】本発明は、工業的に安
価なハロゲノメチル芳香族化合物を用いて、ノボラック
型樹脂の製造を、装置の腐食や、反応の激しさのために
生成物がゲル化を起こしたりすることのない方法で実現
することを目的とする。SUMMARY OF THE INVENTION The present invention relates to a process for producing a novolak resin by using an industrially inexpensive halogenomethyl aromatic compound, and the production of a novolak resin is carried out by gelation due to the corrosion of equipment and the intensity of the reaction. It is intended to realize in a method that does not cause conversion.
【０００４】[0004]
【課題を解決するための手段】すなわち本発明は（１）
下記式（１）で示されるハロゲン化メチル芳香族化合物
を、アルカリ性物質の存在下、芳香族ヒドロキシル化合
物と反応させることによるノボラック型化合物の製造方
法、 Ｒ（−ＣＨ2 Ｘ）n （１） （式中、ｎは２〜３の整数を表す。Ｒは２価または３価
の芳香族基、ＸはＣｌまたはＢｒを表す。） （２）Ｒがフェニル、ナフチル、ビフェニル由来の基で
あるハロゲン化メチル芳香族化合物を用いる上記（１）
記載の製造方法、（３）芳香族ヒドロキシル化合物が、
フェノ−ル、ナフト−ル類またはビフェノ−ル類から選
ばれる上記（１）または（２）記載の製造方法を提供す
る。That is, the present invention provides (1)
A method for producing a novolak-type compound by reacting a halogenated methyl aromatic compound represented by the following formula (1) with an aromatic hydroxyl compound in the presence of an alkaline substance: R (—CH 2 X) n (1) ( In the formula, n represents an integer of 2 to 3. R represents a divalent or trivalent aromatic group, and X represents Cl or Br.) (2) R is a halogen derived from phenyl, naphthyl or biphenyl (1) using a methylated aromatic compound
The method according to the above, wherein (3) the aromatic hydroxyl compound is
The present invention provides the production method according to the above (1) or (2), which is selected from phenol, naphtholes and biphenols.
【０００５】[0005]
【発明の実施形態】上記式（１）で示される具体的化合
物としては、１，４−ビス（クロロメチル）ベンゼン、
１，２−ビス（クロロメチル）ベンゼン、１，３−ビス
（クロロメチル）ベンゼン、１，４−ビス（ブロモメチ
ル）ベンゼン、４，４’−ビス（クロロメチル）ビフェ
ニル、２，４’−ビス（クロロメチル）ビフェニル、
２，２’−ビス（クロロメチル）ビフェニル、４，４’
−ビス（ブロモメチル）ビフェニル、２，４’−ビス
（ブロモメチル）ビフェニル、２，２’−ビス（ブロモ
メチル）ビフェニル、２，６−ビス（クロロメチル）ナ
フタレン、１，４−ビス（クロロメチル）ナフタレン、
等のビスクロロメチルナフタレン類、ビス（ブロモフェ
ニル）ナフタレン類、があげられるが上記式（１）で表
される限り、これらに限定されるものではない。BEST MODE FOR CARRYING OUT THE INVENTION As specific compounds represented by the above formula (1), 1,4-bis (chloromethyl) benzene,
1,2-bis (chloromethyl) benzene, 1,3-bis (chloromethyl) benzene, 1,4-bis (bromomethyl) benzene, 4,4′-bis (chloromethyl) biphenyl, 2,4′-bis (Chloromethyl) biphenyl,
2,2'-bis (chloromethyl) biphenyl, 4,4 '
-Bis (bromomethyl) biphenyl, 2,4'-bis (bromomethyl) biphenyl, 2,2'-bis (bromomethyl) biphenyl, 2,6-bis (chloromethyl) naphthalene, 1,4-bis (chloromethyl) naphthalene ,
Bischloromethylnaphthalenes and bis (bromophenyl) naphthalenes, but are not limited thereto as long as they are represented by the above formula (1).
【０００６】芳香族ヒドロキシル化合物としては、フェ
ノ−ル、ｏ−クレゾ−ル、ｍ−クレゾ−ル、ｐ−クレゾ
−ル、２，６−キシレノ−ル、２，４−キシレノ−ル、
カテコ−ル、レゾルシン、ハイドロキノン、α−ナフト
−ル、β−ナフト−ル、２，６−ジヒドロキシナフタレ
ン、１，５−ジヒドロキシナフタレン、ビフェノ−ル、
ビスフェノ−ル−Ａ、ビスフェノ−ル−Ｆ、等があげら
れる。これらの芳香族ヒドロキシル化合物は、１種また
は、２種以上を混合して使用することができ、その使用
量は、式（１）の化合物中のハロゲン化メチル基１モル
に対して通常０．８〜２０モル、好ましくは１〜１０モ
ルである。Examples of the aromatic hydroxyl compound include phenol, o-cresol, m-cresol, p-cresol, 2,6-xylenol, 2,4-xylenol,
Catechol, resorcinol, hydroquinone, α-naphthol, β-naphthol, 2,6-dihydroxynaphthalene, 1,5-dihydroxynaphthalene, biphenol,
Bisphenol-A, bisphenol-F and the like can be mentioned. These aromatic hydroxyl compounds can be used singly or as a mixture of two or more kinds. The amount of the aromatic hydroxyl compound is usually 0.1 to 1 mol of the methyl halide group in the compound of the formula (1). It is 8 to 20 mol, preferably 1 to 10 mol.
【０００７】使用するアルカリ物質としては、苛性ソ−
ダ、苛性カリ、水酸化リチウム、炭酸ソ−ダ、炭酸カ
リ、炭酸リチウム、重炭酸ソ−ダ、重炭酸カリ、炭酸カ
ルシウム、炭酸マグネシウム、酸化カルシウム、酸化マ
グネシウム、酢酸ソ−ダ、酢酸カリ、シュウ酸ソ−ダま
たは炭酸アンムニウム並びにトリエチルアミンまたはジ
メチルアニリン等の有機アミン類等があげられる。その
使用量は式（１）の化合物中ハロゲン化メチル基１モル
に対して等モルかまたは若干過剰となるように使用す
る。The alkaline substance used is caustic soda.
, Caustic potash, lithium hydroxide, sodium carbonate, potassium carbonate, lithium carbonate, sodium bicarbonate, potassium bicarbonate, calcium carbonate, magnesium carbonate, calcium oxide, magnesium oxide, sodium acetate, potassium acetate, shu Examples thereof include acid soda or ammonium carbonate, and organic amines such as triethylamine and dimethylaniline. The compound is used in such an amount that it is equimolar or slightly excessive with respect to 1 mol of the halogenated methyl group in the compound of the formula (1).
【０００８】反応は、通常溶媒中で行う。溶媒として
は、ヘキサン、ヘプタン、トルエン、キシレン、プソイ
ドキュメン、シクロヘキサン等の炭化水素類、ジクロロ
エタン、塩化エチレン、クロロベンゼン等のハロゲン化
炭化水素類、ジブチルエ−テル、ジオキサンまたはメト
キシエタノ−ル等のエ−テル類、ジメチルフォルムアミ
ド、ジメチルスルフォキシドまたはジメチルイミダゾリ
ジノン等の非プロトン性極性溶媒、メタノ−ル、エタノ
−ル、プロパノ−ルまたはブタノ−ル等のアルコ−ル
類、アセトン、メチルエチルケトンまたはメチルイソブ
チルケトン等のケトン類、水、等が使用できるが、溶媒
を使用しなくても良い。溶媒を使用する場合は、式
（１）の化合物の、１０重量％〜２０重量倍程度使用す
るのが好ましい。また、ジメチルスルフォキシド等の非
プロトン性極性溶媒を使用する場合は、これらがアルカ
リ性物質をよく溶解するため若干反応速度が遅くなるの
で、使用量を全反応混合物中の５０重量％以下、好まし
くは２０重量％以下程度に制限するのが良い。またテト
ラブチルアンモニウムクロライド、トリトンＢ等の相関
移動触媒を全反応混合物中の０．１〜１重量％程度使用
できる。[0008] The reaction is usually carried out in a solvent. Examples of the solvent include hydrocarbons such as hexane, heptane, toluene, xylene, pseudocumene, and cyclohexane; halogenated hydrocarbons such as dichloroethane, ethylene chloride and chlorobenzene; ethers such as dibutyl ether, dioxane and methoxyethanol. Aprotic polar solvents such as dimethylformamide, dimethylsulfoxide or dimethylimidazolidinone, alcohols such as methanol, ethanol, propanol or butanol, acetone, methyl ethyl ketone or methyl Ketones such as isobutyl ketone, water, and the like can be used, but a solvent need not be used. When a solvent is used, it is preferable to use about 10% by weight to 20% by weight of the compound of the formula (1). When an aprotic polar solvent such as dimethyl sulfoxide is used, the amount of the solvent used is preferably 50% by weight or less in the total reaction mixture, since these dissolve the alkaline substance well and the reaction rate is slightly slowed down. Is preferably limited to about 20% by weight or less. Further, a phase transfer catalyst such as tetrabutylammonium chloride and Triton B can be used in an amount of about 0.1 to 1% by weight in the whole reaction mixture.
【０００９】反応温度は、通常４０℃〜２００℃、好ま
しくは６０℃〜１５０℃で行うことが出来る。また、生
成する水を、共沸等により抜き出しながら反応を行う事
もできる。反応を制御するために、式（１）の化合物ま
たは、アルカリ性物質は少量ずつ添加する事もできる
が、アルカリ性物質が式（１）の化合物より少し過剰に
存在する様にするのが好ましい。反応時間は通常１時間
〜２５時間、好ましくは３〜１５時間である。例えば、
非プロトン性極性溶媒を使用した場合のように反応が遅
くなった場合は若干、酸類の添加を行うことで解決でき
る。ここで用いることが出来る酸類は、塩酸、硫酸、リ
ン酸、メタンスルフォン酸、トルエンスルフォン酸類、
ＢＦ3 、塩化アルミニウム、塩化第二鉄等のルイス酸類
があげられる。[0009] The reaction can be carried out at a temperature of usually 40 ° C to 200 ° C, preferably 60 ° C to 150 ° C. Further, the reaction can be carried out while extracting generated water by azeotropic distillation or the like. In order to control the reaction, the compound of the formula (1) or the alkaline substance can be added little by little, but it is preferable that the alkaline substance is present in a slightly excessive amount than the compound of the formula (1). The reaction time is generally 1 hour to 25 hours, preferably 3 to 15 hours. For example,
In the case where the reaction slows down, such as when an aprotic polar solvent is used, it can be solved by slightly adding an acid. Acids that can be used here include hydrochloric acid, sulfuric acid, phosphoric acid, methanesulfonic acid, toluenesulfonic acid,
Lewis acids such as BF3, aluminum chloride and ferric chloride.
【００１０】反応系は弱酸性〜中性に保つのが好まし
い。溶媒系としてアルカリ性物質を完全に溶解しない溶
媒を用いるのが、この条件を保つのに適している。例え
ば、原料の芳香族ヒドロキシ化合物を溶媒とした場合、
及び、トルエン、キシレン、プソイドキュメン、クロロ
ベンゼン、ヘキサン、シクロヘキサン、ヘプタン、ジク
ロロエタン、塩化エチレン等の炭化水素またはハロゲン
化炭化水素類、ジブチルエ−テル、ジオキサン等のエー
テル類、アセトン、メチルエチルケトン、メチルイソブ
チルケトン等のケトン類等を用いた場合はアルカリ性物
質を一時に加えても反応はスム−ズに進行する。また、
アルカリ性物質は固体で用いるのが好ましい。また、反
応によるハロゲン化水素の発生が、ほぼ終わった時点で
上記の酸触媒を添加し、ノボラック化反応を完結させる
のが好ましい。この場合酸触媒の濃度が、０．０１〜５
重量％程度が適している。[0010] The reaction system is preferably kept weakly acidic to neutral. The use of a solvent that does not completely dissolve the alkaline substance as the solvent system is suitable for maintaining this condition. For example, when an aromatic hydroxy compound as a raw material is used as a solvent,
And hydrocarbons or halogenated hydrocarbons such as toluene, xylene, pseudocumene, chlorobenzene, hexane, cyclohexane, heptane, dichloroethane, and ethylene chloride; ethers such as dibutyl ether and dioxane; acetone, methyl ethyl ketone, and methyl isobutyl ketone; When ketones or the like are used, the reaction proceeds smoothly even when an alkaline substance is added at a time. Also,
The alkaline substance is preferably used as a solid. Further, it is preferable to add the above-mentioned acid catalyst at the time when the generation of hydrogen halide by the reaction is almost completed, thereby completing the novolak reaction. In this case, the concentration of the acid catalyst is 0.01 to 5
A weight percent is suitable.
【００１１】反応により塩類が生成する。反応終了後、
塩類を濾過、水洗等により除いた後、溶媒及び／また
は、未反応の芳香族ヒドロキシ化合物を、蒸留または、
溶媒に溶解して除去し、ノボラック化合物を得ることが
出来る。The reaction produces salts. After the reaction,
After removing salts by filtration, washing with water, etc., the solvent and / or unreacted aromatic hydroxy compound is distilled or
The novolak compound can be obtained by dissolving in a solvent and removing.
【００１２】[0012]
【実施例】以下実施例で本発明を更に詳細に説明する
が、本発明はこれらの実施例に限定されるものではな
い。EXAMPLES The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples.
【００１３】実施例１ ３００ｍｌ、４口フラスコに、トルエン５５ｇ、フェノ
−ル２０．７ｇ、炭酸ソ−ダ２３．３ｇ、を仕込み７０
℃に昇温した。ここに、４，４’−ビス（クロロメチ
ル）ビフェニル２５．１ｇを少量ずつ仕込んだ。１時間
で添加を終了した。この後、８０℃で８時間、９５℃で
５時間反応させた。塩化水素ガスの発生は殆ど認められ
なかった。反応終了後、析出した塩を除去し、濾液に念
のためメタンスルフォン酸を０．１ｇ添加し、９０℃で
１時間反応させた。過剰のメタンスルフォン酸を苛性ソ
−ダで中和した後、トルエンを留去し、冷却後３４ｇの
ノボラック型化合物を得た。得られたノボラック型化合
物の軟化点は７５℃、であり、１５０℃における溶融粘
度は２．４ポイズであった。Example 1 A 300-ml four-necked flask was charged with 55 g of toluene, 20.7 g of phenol, and 23.3 g of sodium carbonate, and charged 70.
The temperature was raised to ° C. Here, 25.1 g of 4,4'-bis (chloromethyl) biphenyl was charged little by little. The addition was completed in one hour. Thereafter, the reaction was carried out at 80 ° C. for 8 hours and at 95 ° C. for 5 hours. Almost no generation of hydrogen chloride gas was observed. After completion of the reaction, the precipitated salt was removed, 0.1 g of methanesulfonic acid was added to the filtrate just in case, and the reaction was carried out at 90 ° C. for 1 hour. After neutralizing excess methanesulfonic acid with caustic soda, toluene was distilled off, and after cooling, 34 g of a novolak compound was obtained. The softening point of the obtained novolak type compound was 75 ° C., and the melt viscosity at 150 ° C. was 2.4 poise.
【００１４】実施例２ 式（１）の化合物として１，４−ビス（クロロメチル）
ベンゼンを１７．５ｇを用いた以外は、実施例１と同様
に反応させ、２６．８ｇのノボラック型化合物を得た。
得られたノボラック型化合物の軟化点は７３℃であり、
１５０℃における溶融粘度は３．１ポイズであった。Example 2 As a compound of the formula (1), 1,4-bis (chloromethyl)
The reaction was carried out in the same manner as in Example 1 except that 17.5 g of benzene was used to obtain 26.8 g of a novolak-type compound.
The softening point of the obtained novolak type compound is 73 ° C.,
The melt viscosity at 150 ° C. was 3.1 poise.
【００１５】実施例３ 実施例１においてトルエンを用いず、フェノ−ルを５０
ｇ使用し、炭酸ソ−ダの代わりに炭酸カリを１９ｇ使用
した以外は、実施例１と同様に反応させ、３４．８ｇの
ノボラック型化合物を得た。得られたノボラック型化合
物の軟化点は１０８℃であり、１５０℃における溶融粘
度は０．９ポイズであった。Example 3 In Example 1, 50 parts of phenol was used without using toluene.
The reaction was carried out in the same manner as in Example 1 except that 19 g of potassium carbonate was used instead of sodium carbonate to obtain 34.8 g of a novolak type compound. The softening point of the obtained novolak type compound was 108 ° C., and the melt viscosity at 150 ° C. was 0.9 poise.
【００１６】[0016]
【発明の効果】本発明によればハロゲン化メチル芳香族
化合物より、効率的にノボラック型化合物が得られるよ
うになった。得られたノボラック型化合物は、半導体封
止用のエポキシ樹脂硬化剤やエポキシ樹脂の合成原料と
して有用である。According to the present invention, a novolak type compound can be obtained more efficiently than a halogenated methyl aromatic compound. The obtained novolak type compound is useful as an epoxy resin curing agent for semiconductor encapsulation or as a raw material for synthesizing an epoxy resin.
Claims (3)
芳香族化合物を、アルカリ性物質の存在下、芳香族ヒド
ロキシル化合物と反応させることによるノボラック型化
合物の製造方法。 Ｒ（−ＣＨ2 Ｘ）n （１） （式中、ｎは２〜３の整数を表す。Ｒは２価または３価
の芳香族基、ＸはＣｌまたはＢｒを表す。）1. A method for producing a novolak compound by reacting a halogenated methyl aromatic compound represented by the following formula (1) with an aromatic hydroxyl compound in the presence of an alkaline substance. R (-CH 2 X) n ( 1) ( wherein, n represents an integer of 2 to 3 .R divalent or trivalent aromatic group, X represents Cl or Br.)
由来の基であるハロゲン化メチル芳香族化合物を用いる
請求項１記載の製造方法。2. The method according to claim 1, wherein R is a halogenated methyl aromatic compound, which is a group derived from phenyl, naphthyl or biphenyl.
ル、ナフト−ル類またはビフェノ−ル類から選ばれる１
種以上である請求項１または２記載の製造方法。3. The method according to claim 1, wherein the aromatic hydroxyl compound is pheno-
1 selected from phenols, naphtholes and biphenols
3. The method according to claim 1, wherein the method is at least one kind.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30088196A JP3819089B2 (en) | 1996-10-28 | 1996-10-28 | Method for producing novolac type compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30088196A JP3819089B2 (en) | 1996-10-28 | 1996-10-28 | Method for producing novolac type compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH10130352A true JPH10130352A (en) | 1998-05-19 |
| JP3819089B2 JP3819089B2 (en) | 2006-09-06 |
Family
ID=17890250
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP30088196A Expired - Fee Related JP3819089B2 (en) | 1996-10-28 | 1996-10-28 | Method for producing novolac type compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3819089B2 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002241685A (en) * | 2001-02-22 | 2002-08-28 | Nippon Kayaku Co Ltd | Method for producing polyphenol resin-containing varnish |
| JP2006335841A (en) * | 2005-06-01 | 2006-12-14 | Ube Ind Ltd | p-Xylylene-phenolic resin and process for producing the same |
| JP2008056944A (en) * | 2007-11-19 | 2008-03-13 | Nippon Kayaku Co Ltd | Epoxy resin composition |
| JP2010138311A (en) * | 2008-12-12 | 2010-06-24 | Jfe Chemical Corp | Production method of 4,4'-biphenyldiyl methylene-phenol resin |
| JP2012229436A (en) * | 2012-07-18 | 2012-11-22 | Nippon Kayaku Co Ltd | Epoxy resin composition |
-
1996
- 1996-10-28 JP JP30088196A patent/JP3819089B2/en not_active Expired - Fee Related
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002241685A (en) * | 2001-02-22 | 2002-08-28 | Nippon Kayaku Co Ltd | Method for producing polyphenol resin-containing varnish |
| JP2006335841A (en) * | 2005-06-01 | 2006-12-14 | Ube Ind Ltd | p-Xylylene-phenolic resin and process for producing the same |
| JP2008056944A (en) * | 2007-11-19 | 2008-03-13 | Nippon Kayaku Co Ltd | Epoxy resin composition |
| JP2010138311A (en) * | 2008-12-12 | 2010-06-24 | Jfe Chemical Corp | Production method of 4,4'-biphenyldiyl methylene-phenol resin |
| TWI402291B (en) * | 2008-12-12 | 2013-07-21 | Jfe Chemical Corp | Method for manufacturing 4,4'-biphenyldiylmethylene-phenol resin |
| JP2012229436A (en) * | 2012-07-18 | 2012-11-22 | Nippon Kayaku Co Ltd | Epoxy resin composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3819089B2 (en) | 2006-09-06 |
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