JPH0283353A - Aromatic compound and production thereof - Google Patents
Aromatic compound and production thereofInfo
- Publication number
- JPH0283353A JPH0283353A JP23206988A JP23206988A JPH0283353A JP H0283353 A JPH0283353 A JP H0283353A JP 23206988 A JP23206988 A JP 23206988A JP 23206988 A JP23206988 A JP 23206988A JP H0283353 A JPH0283353 A JP H0283353A
- Authority
- JP
- Japan
- Prior art keywords
- aromatic compound
- formula
- compound
- carbon atoms
- group
- 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.)
- Pending
Links
- 150000001491 aromatic compounds Chemical class 0.000 title claims abstract description 36
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 9
- 238000002844 melting Methods 0.000 abstract description 8
- 230000008018 melting Effects 0.000 abstract description 8
- 150000001339 alkali metal compounds Chemical class 0.000 abstract description 7
- 239000000463 material Substances 0.000 abstract description 7
- 239000003054 catalyst Substances 0.000 abstract description 6
- 229920000642 polymer Polymers 0.000 abstract description 6
- 230000007935 neutral effect Effects 0.000 abstract description 5
- 239000002798 polar solvent Substances 0.000 abstract description 5
- 239000012769 display material Substances 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 238000013329 compounding Methods 0.000 abstract 1
- 238000005034 decoration Methods 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- FFFPYJTVNSSLBQ-UHFFFAOYSA-N Phenolphthalin Chemical compound OC(=O)C1=CC=CC=C1C(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 FFFPYJTVNSSLBQ-UHFFFAOYSA-N 0.000 description 11
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- -1 polyethylene Polymers 0.000 description 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000011342 resin composition Substances 0.000 description 4
- 238000005979 thermal decomposition reaction Methods 0.000 description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- QSSXJPIWXQTSIX-UHFFFAOYSA-N 1-bromo-2-methylbenzene Chemical compound CC1=CC=CC=C1Br QSSXJPIWXQTSIX-UHFFFAOYSA-N 0.000 description 2
- QGRPVMLBTFGQDQ-UHFFFAOYSA-N 1-chloro-2-methoxybenzene Chemical compound COC1=CC=CC=C1Cl QGRPVMLBTFGQDQ-UHFFFAOYSA-N 0.000 description 2
- RINOYHWVBUKAQE-UHFFFAOYSA-N 1-iodo-2-methylbenzene Chemical compound CC1=CC=CC=C1I RINOYHWVBUKAQE-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 229910021594 Copper(II) fluoride Inorganic materials 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 229910000365 copper sulfate Inorganic materials 0.000 description 2
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(i) oxide Chemical compound [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 2
- GWFAVIIMQDUCRA-UHFFFAOYSA-L copper(ii) fluoride Chemical compound [F-].[F-].[Cu+2] GWFAVIIMQDUCRA-UHFFFAOYSA-L 0.000 description 2
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 2
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 2
- CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BSJWDQYZFBYNIM-UHFFFAOYSA-N 1,3,4,5-tetramethylpyrrolidin-2-one Chemical compound CC1C(C)N(C)C(=O)C1C BSJWDQYZFBYNIM-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
- BCNBMSZKALBQEF-UHFFFAOYSA-N 1,3-dimethylpyrrolidin-2-one Chemical compound CC1CCN(C)C1=O BCNBMSZKALBQEF-UHFFFAOYSA-N 0.000 description 1
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 1
- WLPXNBYWDDYJTN-UHFFFAOYSA-N 1-bromo-2,3-dimethylbenzene Chemical group CC1=CC=CC(Br)=C1C WLPXNBYWDDYJTN-UHFFFAOYSA-N 0.000 description 1
- HTDQSWDEWGSAMN-UHFFFAOYSA-N 1-bromo-2-methoxybenzene Chemical compound COC1=CC=CC=C1Br HTDQSWDEWGSAMN-UHFFFAOYSA-N 0.000 description 1
- ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 description 1
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 1
- BNXZHVUCNYMNOS-UHFFFAOYSA-N 1-butylpyrrolidin-2-one Chemical compound CCCCN1CCCC1=O BNXZHVUCNYMNOS-UHFFFAOYSA-N 0.000 description 1
- NVLHGZIXTRYOKT-UHFFFAOYSA-N 1-chloro-2,3-dimethylbenzene Chemical group CC1=CC=CC(Cl)=C1C NVLHGZIXTRYOKT-UHFFFAOYSA-N 0.000 description 1
- RNEMUWDQJSRDMQ-UHFFFAOYSA-N 1-chloro-2-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC=C1Cl RNEMUWDQJSRDMQ-UHFFFAOYSA-N 0.000 description 1
- JUJREUXKABNEFA-UHFFFAOYSA-N 1-ethoxy-2-iodobenzene Chemical compound CCOC1=CC=CC=C1I JUJREUXKABNEFA-UHFFFAOYSA-N 0.000 description 1
- IVVVGBHWWAJRAY-UHFFFAOYSA-N 1-ethyl-3-methylpyrrolidin-2-one Chemical compound CCN1CCC(C)C1=O IVVVGBHWWAJRAY-UHFFFAOYSA-N 0.000 description 1
- DANMWBNOPFBJSZ-UHFFFAOYSA-N 1-iodo-2,3-dimethylbenzene Chemical group CC1=CC=CC(I)=C1C DANMWBNOPFBJSZ-UHFFFAOYSA-N 0.000 description 1
- DVQWNQBEUKXONL-UHFFFAOYSA-N 1-iodo-2-methoxybenzene Chemical compound COC1=CC=CC=C1I DVQWNQBEUKXONL-UHFFFAOYSA-N 0.000 description 1
- QFUYDAGNUJWBSM-UHFFFAOYSA-N 1-iodo-2-phenylbenzene Chemical group IC1=CC=CC=C1C1=CC=CC=C1 QFUYDAGNUJWBSM-UHFFFAOYSA-N 0.000 description 1
- SORQIYFSJAWBNQ-UHFFFAOYSA-N 1-iodo-2-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC=C1I SORQIYFSJAWBNQ-UHFFFAOYSA-N 0.000 description 1
- GGYVTHJIUNGKFZ-UHFFFAOYSA-N 1-methylpiperidin-2-one Chemical compound CN1CCCCC1=O GGYVTHJIUNGKFZ-UHFFFAOYSA-N 0.000 description 1
- GVDQKJQFVPXADH-UHFFFAOYSA-N 1-propan-2-ylpiperidin-2-one Chemical compound CC(C)N1CCCCC1=O GVDQKJQFVPXADH-UHFFFAOYSA-N 0.000 description 1
- GHELJWBGTIKZQW-UHFFFAOYSA-N 1-propan-2-ylpyrrolidin-2-one Chemical compound CC(C)N1CCCC1=O GHELJWBGTIKZQW-UHFFFAOYSA-N 0.000 description 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- LAXBNTIAOJWAOP-UHFFFAOYSA-N 2-chlorobiphenyl Chemical group ClC1=CC=CC=C1C1=CC=CC=C1 LAXBNTIAOJWAOP-UHFFFAOYSA-N 0.000 description 1
- DRYYJQYUHPRVBN-UHFFFAOYSA-N 3-ethyl-1-methylpiperidin-2-one Chemical compound CCC1CCCN(C)C1=O DRYYJQYUHPRVBN-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910001431 copper ion Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- SEACYXSIPDVVMV-UHFFFAOYSA-L eosin Y Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 SEACYXSIPDVVMV-UHFFFAOYSA-L 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- IMNDHOCGZLYMRO-UHFFFAOYSA-N n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1 IMNDHOCGZLYMRO-UHFFFAOYSA-N 0.000 description 1
- PZYDAVFRVJXFHS-UHFFFAOYSA-N n-cyclohexyl-2-pyrrolidone Chemical compound O=C1CCCN1C1CCCCC1 PZYDAVFRVJXFHS-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
Abstract
Description
【発明の詳細な説明】
[産業上の利用分野]
この発明は新規な芳香族化合物およびその製造方法に関
し、さらに詳しく言うと、蛍光性を有するとともに優れ
た耐熱性を有するものであって、たとえば高融点のポリ
マーに配合することにより、耐熱性に優れた表示材料や
装飾材料に好適に利用することのできる芳香族化合物、
およびこの芳香族化合物を簡単な工程で効率良く製造す
る方法に関する。[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to a novel aromatic compound and a method for producing the same. More specifically, the present invention relates to a novel aromatic compound and a method for producing the same. More specifically, the present invention relates to a novel aromatic compound and a method for producing the same. Aromatic compounds that can be suitably used in display materials and decorative materials with excellent heat resistance by being blended with high melting point polymers.
The present invention also relates to a method for efficiently producing this aromatic compound through simple steps.
[従来技術および発明が解決しようとする課題]蛍光性
樹脂組成物はたとえば夜間標識や装飾品などの形成材料
として有用であり、実際にこれらの用途に多用されてい
る。[Prior Art and Problems to be Solved by the Invention] Fluorescent resin compositions are useful, for example, as forming materials for nighttime signs, ornaments, etc., and are actually widely used for these purposes.
この蛍光性樹脂組成物としては、たとえば、ポリエチレ
ン、ポリプロピレン、ポリスチレン、塩化ビニル系樹脂
などの熱可塑性樹脂に、フルオレセイン、ローダミンB
、エオシンYなどの蛍光体を配合してなるものが従来よ
り一般に用いられている。This fluorescent resin composition includes, for example, a thermoplastic resin such as polyethylene, polypropylene, polystyrene, vinyl chloride resin, fluorescein, rhodamine B, etc.
, Eosin Y, and other phosphors have been commonly used.
しかしながら、従来の蛍光体はいずれも耐熱性や耐候性
が充分ではないので、これらの蛍光体を配合してなる従
来の蛍光性樹脂組成物は、高温環境下での使用に耐えら
れない。However, all conventional phosphors do not have sufficient heat resistance or weather resistance, so conventional fluorescent resin compositions containing these phosphors cannot withstand use in high-temperature environments.
また、従来の蛍光体においては、融点の高い高強度樹脂
に配合することが困難であるという問題がある。Furthermore, conventional phosphors have a problem in that they are difficult to blend into high-strength resins with high melting points.
すなわち、充分な耐熱性を有していて熱安定性の優れた
蛍光体が望まれているのか現状である。In other words, there is currently a need for a phosphor that has sufficient heat resistance and excellent thermal stability.
この発明は前記の事情に基いてなされたものである。This invention was made based on the above circumstances.
この発明の目的は、蛍光性を有するとともに優れた耐熱
性を有していて、たとえば高融点のポリマーに配合する
ことにより蛍光性樹脂組成物に好適に使用することのて
きる芳香族化合物と、この芳香族化合物を簡単な工程で
効率良く製造する方法とを提供することにある。An object of the present invention is to provide an aromatic compound which has fluorescence and excellent heat resistance, and which can be suitably used in a fluorescent resin composition by being blended with a high melting point polymer, for example; The object of the present invention is to provide a method for efficiently producing this aromatic compound through simple steps.
[課題を解決するための手段]
前記課題を解決するために、本発明者が鋭意検討を重ね
た結果、特定の構造を有する芳香族化合物は、蛍光性を
有するとともに優れた耐熱性を示し、この特定の芳香族
化合物はフェノールフタリン類と、特定のハロゲン化芳
香族化合物とを用いた特定の反応によって簡単な工程で
、効率良く製造することかてきることを見い出して、こ
の発明に到達した。[Means for Solving the Problems] In order to solve the above problems, as a result of intensive studies by the present inventors, it was found that an aromatic compound having a specific structure has fluorescence and exhibits excellent heat resistance, This invention was achieved by discovering that this specific aromatic compound can be efficiently produced in a simple process through a specific reaction using phenolphthalins and a specific halogenated aromatic compound. did.
すなわち、請求項1の発明の構成は、次式[]:
素数6〜8のアリール基、炭素数6〜8のアリールオキ
シ基のいずれかであり、mEよびnは、それぞれOおよ
び1〜4の整数のいずれかであり、pは0および1〜5
の整数のいずれかである。)で表わされる芳香族化合物
てあり、
請求項2の発明の構成は、次式[nl ;[1]
(ただし、式[I]中 R1およびR2は炭素数1〜6
のアルキル基、炭素数1〜6のアルコキシ基、炭素数6
〜8のアリール基、炭素数6〜8のアリールオキシ基、
カルボキシル基およびハロゲン原子のいずれかであり、
R3は炭素数1〜6のアルキル基、炭素数1〜6のアル
コキシ基、炭(たたし1式[11中、R’ 、R2,m
およびnは前記と同じ意味である。)
で表わされるフェノールフタリン類と、次式[■];
(ただし、式[III]中、R3およびpは前記と同じ
意味であり、Xはハロゲン原子である。)で表わされる
ハロゲン化芳香族化合物とを反応させることを特徴とす
る請求項lに記載の芳香族化合物の製造方法である。That is, the structure of the invention of claim 1 is the following formula [ ]: Either an aryl group having a prime number of 6 to 8 or an aryloxy group having 6 to 8 carbon atoms, mE and n are O and 1 to 4, respectively. p is any integer of 0 and 1 to 5
is one of the integers. ), and the structure of the invention of claim 2 is the following formula [nl;[1] (wherein R1 and R2 have 1 to 6 carbon atoms in formula [I])
alkyl group, alkoxy group having 1 to 6 carbon atoms, 6 carbon atoms
-8 aryl group, C6-8 aryloxy group,
Either a carboxyl group or a halogen atom,
R3 is an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, charcoal (R', R2, m
and n have the same meanings as above. ) Phenolphthalins represented by the following formula [■]; (However, in the formula [III], R3 and p have the same meanings as above, and X is a halogen atom.) The method for producing an aromatic compound according to claim 1, characterized in that the aromatic compound is reacted with a compound of the aromatic group.
請求項1に記載の芳香族化合物は、請求項2に記載の方
法にしたがって、フェノールフタリン類と、ハロゲン化
芳香族化合物とを反応させることにより、製造すること
ができる。The aromatic compound according to claim 1 can be produced by reacting phenolphthalins and a halogenated aromatic compound according to the method according to claim 2.
請求項2に記載の製造方法において、使用に供される前
記フェノールフタリン類としては、たとえば、次式:
で表わされるフェノールフタリンや、
(本頁、以下余白)
などのフェノールフタリン誘導体が挙げられる。In the manufacturing method according to claim 2, the phenolphthalins used include, for example, phenolphthalin represented by the following formula: and phenolphthalin derivatives such as (this page, hereafter in the margin). Can be mentioned.
これらの中でも、好ましいのはフェノールフタリン、ク
レゾールフタリン、チモールフタリンである。Among these, preferred are phenolphthalin, cresolphthalin, and thymolphthalin.
請求項2に記載の製造方法において、使用に供される前
記ハロゲン化芳香族化合物としては、たとえばクロロベ
ンゼン、ブロムベンゼン、ヨードベンゼン、クロロトル
エン、ブロムトルエン、ヨードトルエン、クロロキシレ
ン、ブロムキシレン、ヨードキシレン、クロロクメン、
ブロムクメン、ヨードクメン、クロロアニソール、ブロ
ムアニソール、ヨードアニソール、クロロアニソ−ル、
プロムフェネトール、ヨードフェネトール、クロロビフ
ェニル、ブロムビフェニル、ヨードビフェニルなどが挙
げられる。In the production method according to claim 2, the halogenated aromatic compound used includes, for example, chlorobenzene, bromobenzene, iodobenzene, chlorotoluene, bromotoluene, iodotoluene, chloroxylene, bromoxylene, iodoxylene. , chlorocumene,
Bromcumene, iodocumene, chloroanisole, bromoanisole, iodoanisole, chloroanisole,
Examples include promphenetole, iodophenetol, chlorobiphenyl, brombiphenyl, iodobiphenyl, and the like.
これらの中でも、好ましいのはクロロベンゼン、ブロム
ベンゼン、ヨードベンゼン、クロロトルエン、ブロムト
ルエン、ヨードトルエン、ブロムビフェニルである。Among these, preferred are chlorobenzene, brombenzene, iodobenzene, chlorotoluene, bromotoluene, iodotoluene, and brombiphenyl.
請求項2に記載の製造方法においては、前記フェノール
フタリン類と、前記ハロゲン化芳香族化合物とを、通常
、触媒およびアルカリ金属化合物の存在下に、中性極性
溶媒中で反応させて、請求項1に記載の芳香族化合物を
得る。In the manufacturing method according to claim 2, the phenolphthalin and the halogenated aromatic compound are reacted in a neutral polar solvent, usually in the presence of a catalyst and an alkali metal compound. The aromatic compound described in Item 1 is obtained.
前記触媒としては、銅および銅の一価または二価のイオ
ンを好適なものとして挙げることかてきる。さらに具体
的には、たとえば銅、酸化銅(I)、#化銅(■)、塩
化銅(I)、塩化銅(■)、硫酸銅(り、硫酸銅(■)
、硝酸銅(I)、硝酸銅(■)、臭化銅(1)、臭化銅
(■)、フッ化銅(I)、フッ化銅(■)、ヨウ化銅(
■)、ヨウ化銅(n)などが挙げられる。Suitable examples of the catalyst include copper and monovalent or divalent copper ions. More specifically, examples include copper, copper(I) oxide, copper chloride(■), copper(I) chloride, copper chloride(■), copper sulfate(RI), copper sulfate(■)
, copper nitrate (I), copper nitrate (■), copper bromide (1), copper bromide (■), copper fluoride (I), copper fluoride (■), copper iodide (
(2), copper iodide (n), etc.
前記アルカリ金属化合物については、前記式[■]で表
わされるフェノールフタリン類をアルカリ金属塩にする
ことのできるものであればよく、特に制限はないが、好
ましいのはアルカリ金属水酸化物である。The alkali metal compound is not particularly limited as long as it can convert the phenolphthalin represented by the formula [■] into an alkali metal salt, but alkali metal hydroxides are preferred. .
前記アルカリ金属水酸化物としては、たとえば水酸化リ
チウム、水酸化ナトリウム、水酸化カリウム、水酸化ル
ビジウム、水酸化セシウムなどが挙げられる。Examples of the alkali metal hydroxide include lithium hydroxide, sodium hydroxide, potassium hydroxide, rubidium hydroxide, and cesium hydroxide.
これらの中でも、特に好ましいのは水酸化ナトリウム、
水酸化カリウムである。Among these, particularly preferred are sodium hydroxide,
Potassium hydroxide.
前記中性極性溶媒としては、たとえばN、N−ジメチル
ホルムアミド、N、N−ジエチルホルムアミド、N、N
−ジメチルアセトアミド、N、N−ジエチルアセトアミ
ド、 N、N−ジエチルアセトアミド、N、N−ジメチ
ル安息香酸アミド、N−メチル−2−ピロリドン、N−
エチル−2−ピロリドン、N−イソプロピル−2−ピロ
リドン、N−インブチル−2−ピロリドン、N−n−プ
ロとルー2−ピロリドン、N−n−ブチル−2−ピロリ
ドン、N−シクロへキシル−2−ピロリドン、N−メチ
ル−3−メチル−2−ピロリドン、N−エチル−3−メ
チル−2−ピロリドン、N−メチル−3,4,5−トリ
メチル−2−ピロリドン、N−メチル−2−ピペリドン
、N−エチル−2−ピペリトン、N−イソプロピル−2
−ピペリドン、N−メチル−6−メチル−2−ピペリト
ン、N−メチル−3−エチルピペリドン、ジメチルスル
ホキシド、ジエチルスルホキシド、l−メチル−1−オ
キソスルホラン、l−エチル−1−オキソスルホラン、
1−フェニル−1−オキソスルホラン、ジメチルイミダ
ゾリジノン、ジフェニルスルホンなどが挙げられる。Examples of the neutral polar solvent include N,N-dimethylformamide, N,N-diethylformamide, N,N
-dimethylacetamide, N,N-diethylacetamide, N,N-diethylacetamide, N,N-dimethylbenzoic acid amide, N-methyl-2-pyrrolidone, N-
Ethyl-2-pyrrolidone, N-isopropyl-2-pyrrolidone, N-inbutyl-2-pyrrolidone, N-n-pro-2-pyrrolidone, N-butyl-2-pyrrolidone, N-cyclohexyl-2 -pyrrolidone, N-methyl-3-methyl-2-pyrrolidone, N-ethyl-3-methyl-2-pyrrolidone, N-methyl-3,4,5-trimethyl-2-pyrrolidone, N-methyl-2-piperidone , N-ethyl-2-piperitone, N-isopropyl-2
-piperidone, N-methyl-6-methyl-2-piperitone, N-methyl-3-ethylpiperidone, dimethyl sulfoxide, diethyl sulfoxide, l-methyl-1-oxosulfolane, l-ethyl-1-oxosulfolane,
Examples include 1-phenyl-1-oxosulfolane, dimethylimidazolidinone, and diphenylsulfone.
請求項2に記載の芳香族化合物の製造方法において、前
記フェノールフタリン類と、前記ハロゲン化芳香族化合
物との使用割合は、前記フェノールフタリン類に対する
前記ハロゲン化芳香族化合物のモル比で、通常、1.9
8〜2.02の割合であり、好ましくは2.00〜2.
旧の割合である。In the method for producing an aromatic compound according to claim 2, the usage ratio of the phenolphthalin and the halogenated aromatic compound is a molar ratio of the halogenated aromatic compound to the phenolphthalin, Usually 1.9
The ratio is between 8 and 2.02, preferably between 2.00 and 2.02.
This is the old ratio.
前記触媒の使用割合は、前記フェノールフタリン類に対
する前記触媒のモル分率で、通常、0.1〜20モル%
、好ましくは1〜20モル%の割合である。この割合が
0.1モル%未満であると、得られる芳香族化合物の収
率が低下することかある。一方、20モル%を超えると
、生成物が著しく着色し易くなる。The usage ratio of the catalyst is the molar fraction of the catalyst to the phenolphthalin, and is usually 0.1 to 20 mol%.
, preferably 1 to 20 mol%. If this ratio is less than 0.1 mol%, the yield of the aromatic compound obtained may decrease. On the other hand, if it exceeds 20 mol %, the product will be extremely likely to be colored.
前記アルカリ金属化合物の使用割合は、前記アルカリ金
属化合物の種類により異なるので一様に規定することは
できないが、たとえば前記アルカリ金属水酸化物を用い
る場合の前記アルカリ金属水酸化物の使用割合は、前記
フェノールフタリン類に対する前記アルカリ金属水酸化
物のモル比で、通常、2.0〜4.0であり、好ましく
は3.0〜3.5である。The usage ratio of the alkali metal compound varies depending on the type of the alkali metal compound and cannot be uniformly defined, but for example, when the alkali metal hydroxide is used, the usage ratio of the alkali metal hydroxide is as follows: The molar ratio of the alkali metal hydroxide to the phenolphthalin is usually 2.0 to 4.0, preferably 3.0 to 3.5.
前記中性極性溶媒の使用量については、特に制限はない
か、通常、前記フェノールフタリン類と、前記ハロゲン
化芳香族化合物と、前記アルカリ金属化合物との合計1
00 l撮部当り、200〜1000重量部の範囲で選
ばれる。Is there any particular restriction on the amount of the neutral polar solvent used? Usually, the amount of the phenolphthalin, the halogenated aromatic compound, and the alkali metal compound is 1
The amount is selected in the range of 200 to 1000 parts by weight per 00 liter imaging unit.
請求項2に記載の製造方法により、請求項1に記載の芳
香族化合物を得るには、たとえば前記中性極性溶媒中に
、前記フェノールフタリン類と、前記ハロゲン化芳香族
化合物と、前記触媒およびアルカリ金属化合物とを、同
時に、または適当に分けて適宜に添加し、通常は50〜
250°C1好ましくは100〜200℃の範囲の温度
において反応を行なわせる0反応温度が50°C未満で
は、反応速度か遅すぎて実用的ではないし、250°C
を超えると副反応を招くことがある。In order to obtain the aromatic compound according to claim 1 by the production method according to claim 2, for example, the phenolphthalins, the halogenated aromatic compound, and the catalyst are added to the neutral polar solvent. and an alkali metal compound at the same time or in appropriate portions, and usually 50 to
250°C1 Preferably, the reaction is carried out at a temperature in the range of 100 to 200°C.If the reaction temperature is less than 50°C, the reaction rate is too slow to be practical;
Exceeding this may lead to side reactions.
また、この反応における反応時間は、通常1時間〜50
時間であり、好ましくは10〜20時間である。In addition, the reaction time in this reaction is usually 1 hour to 50 minutes.
time, preferably 10 to 20 hours.
このようにして得られる請求項1に記載の芳香族化合物
は、融点および熱分解開始温度が高くて耐熱性に優れた
蛍光体であり、たとえば高融点のポリマーに配合するこ
とにより、耐熱性に優れた表示材料や装飾材料に好適に
利用することかできる。The aromatic compound according to claim 1 obtained in this way is a phosphor having a high melting point and a high thermal decomposition initiation temperature and has excellent heat resistance. It can be suitably used for excellent display materials and decorative materials.
そして、上記の優れた特性を有する芳香族化合物は、請
求項2の方法により簡単な工程で効率良く製造すること
ができる。The aromatic compound having the above-mentioned excellent properties can be efficiently produced in a simple process by the method of claim 2.
[実施例]
次に、この発明の実施例を示し、この発明についてさら
に具体的に説明する。[Example] Next, an example of the present invention will be shown and the present invention will be explained in more detail.
(実施例1)
攪拌装置、アルゴンガス吹込管、ディーンスタルクトラ
ップを備えた300■文のセパラブルフラスコに、フェ
ノールフタリン48.05 g (0,15モル)、水
酸化カリウム19.8g (含量85%、0.3モル)
、ジメチルアセトアミド150■立および水15■文を
入れ、攪拌した。(Example 1) 48.05 g (0.15 mol) of phenolphthalin and 19.8 g of potassium hydroxide (content 85%, 0.3 mol)
, 150 liters of dimethylacetamide and 15 liters of water were added and stirred.
内容物か溶解したのを確認した後、トルエン20■文を
入れ、温度150°Cのオイルバスて加熱した。その間
、トルエンを満たしたディーンスタルクトラップにより
木を除去した。この状態を2時間続けて水の留出かない
ことを確認した後、フラスコ内のトルエンを留去した。After confirming that the contents had dissolved, 20 μm of toluene was added and heated in an oil bath at a temperature of 150°C. Meanwhile, trees were removed using Dean-Starck traps filled with toluene. After continuing this state for 2 hours and confirming that no water was distilled out, the toluene in the flask was distilled off.
次いて、ブロムベンゼン50.2g (0,32モル)
、塩化第一銅3.og (0,0:1モル)を加え、温
度140°Cで12時間加熱攪拌した。Then, 50.2 g (0.32 mol) of bromobenzene
, cuprous chloride3. og (0.0:1 mol) was added, and the mixture was heated and stirred at a temperature of 140°C for 12 hours.
冷却後、希塩酸lす中に反応溶液を入れ、有機層を希塩
酸て2回洗浄した後、未反応のブロムベンゼンを留去し
て生成物53.8g (収率76%)を得た。After cooling, the reaction solution was poured into diluted hydrochloric acid, and the organic layer was washed twice with diluted hydrochloric acid, and unreacted bromobenzene was distilled off to obtain 53.8 g of product (yield: 76%).
この生成物の特性について測定したところ、融点162
°C1熱分解開始温度396°C(空気中、5%重量減
)てあった。The properties of this product were measured and found to have a melting point of 162
°C1 Thermal decomposition initiation temperature was 396 °C (5% weight loss in air).
また、IR測測定行なったところ、 1690cm−’
にカルボン酸による吸収が、また、1240cm−’に
エーテルによる吸収かそれぞれ確認された。In addition, when IR measurement was performed, it was 1690 cm-'
Absorption by carboxylic acid was confirmed at 1240 cm-', and absorption by ether was confirmed at 1240 cm-'.
このポリマーの赤外吸収スペクトルを第1図に示す。The infrared absorption spectrum of this polymer is shown in FIG.
さらに、元素分析を行なったところ、以下のような結果
を得た。Furthermore, elemental analysis was performed and the following results were obtained.
これらの測定結果に基〈この生成物の構造を下記の式で
示す。Based on these measurement results, the structure of this product is shown by the following formula.
元Xn折
C:測定値81.73
計算値81.34
H:測定値4.99
計算値5.12
0:測定値13.28
計算値13.54
さらにまた、このボッマーに410n■の光を照射した
ところ、4g0n■〜500nmの強い蛍光を発した。Original Xn fold C: Measured value 81.73 Calculated value 81.34 H: Measured value 4.99 Calculated value 5.12 0: Measured value 13.28 Calculated value 13.54 Furthermore, a light of 410n■ was applied to this bomber. When irradiated, strong fluorescence of 4gOn■ to 500nm was emitted.
(実施例2)
前記実施例1において、ブロムベンゼン50.2g(0
,32モル)に代えて、4−ブロモビフェニル74.5
9 g(0,:12モル)を使用したほかは前記実施例
1と同様にして実施した。(Example 2) In Example 1, 50.2 g of bromobenzene (0
, 32 mol), 4-bromobiphenyl 74.5
The procedure was carried out in the same manner as in Example 1 except that 9 g (0,:12 mol) was used.
得られた生成物は、59.1g (収率63%)てあっ
た。The amount of product obtained was 59.1 g (yield 63%).
この生成物の特性について測定したところ、融点179
°C1熱分解開始温度405°C(空気中、5%重量減
)であった。The properties of this product were measured and found to have a melting point of 179
°C1 Thermal decomposition initiation temperature was 405 °C (5% weight loss in air).
また、IR測測定行なったところ、1590cm−’に
カルボン酸による吸収か、また、1240cm−’にエ
ーテルによる吸収かそれぞれ確認された。Further, when IR measurement was carried out, it was confirmed that absorption was due to carboxylic acid at 1590 cm-' and absorption due to ether was at 1240 cm-'.
さらに1元素分析を行なったところ、以下のような結果
を得た。Further single element analysis was performed and the following results were obtained.
これらの測定結果に基〈この生成物の構造を下記の式て
示す。Based on these measurement results, the structure of this product is shown by the following formula.
元」L1折
C;測定値84.17
計算値84.59
H:測定値5.29
計算値5.16
0=測定値10.54
計算値10.25
さらにまた、このポリマーに4100−の光を照射した
ところ、 480n+s〜500nmの強い蛍光を発し
た。Original L1 fold C: Measured value 84.17 Calculated value 84.59 H: Measured value 5.29 Calculated value 5.16 0 = Measured value 10.54 Calculated value 10.25 Furthermore, this polymer was exposed to 4100- When irradiated with , strong fluorescence of 480n+s to 500nm was emitted.
(実施例3)
前記実施例1において、ブロムベンゼン50.1g(0
,32モル)に代えて、P−ブロムトルエン54.73
g (O12モル)を使用したほかは前記実施例1と
同様にして実施した。(Example 3) In Example 1, 50.1 g of bromobenzene (0
, 32 mol), P-bromotoluene 54.73
Example 1 was carried out in the same manner as in Example 1, except that g (12 moles of O) was used.
得られた生成物は、37g(収率49%)てあった。The amount of product obtained was 37 g (yield 49%).
この生成物の特性について測定したところ、ワックス状
であり、熱分解開始温度400°C(空気中、5%重量
減)であった。When the properties of this product were measured, it was found to be waxy, with a thermal decomposition onset temperature of 400°C (5% weight loss in air).
また、IRa定を行なったところ、1690cm−’に
カルボン酸による吸収が、また、1240cm−’にエ
ーテルによる吸収かそれぞれ確認された。Further, when IRa measurement was carried out, absorption due to carboxylic acid at 1690 cm-' and absorption due to ether at 1240 cm-' were confirmed.
さらに1元素分析を行なったところ、以下のような結果
を得た。Further single element analysis was performed and the following results were obtained.
これらの測定結果に基くこの生成物の構造を下記の式で
示す。The structure of this product based on these measurement results is shown by the formula below.
元」し1折
CAM定値81.11
計算値81.58
H:測定値5.83
計算値5.64
0:測定値13.06
計算値12.78
さらにまた、このポリマーに400n■の光を照射した
ところ、 480ns〜520n−の強い蛍光を発した
。Original 1-fold CAM fixed value 81.11 Calculated value 81.58 H: Measured value 5.83 Calculated value 5.64 0: Measured value 13.06 Calculated value 12.78 Furthermore, 400n of light was applied to this polymer. When irradiated, strong fluorescence of 480ns to 520n was emitted.
[発明の効果]
この発明によると、
(1) 蛍光性を示し、しかも充分な耐熱性を有する
ものであって、たとえば融点の高い高強度樹脂に配合す
ることにより、高温環境下での使用にも耐え得る表示材
料や装飾材料などに好適に利用することのてきる新規な
芳香族化合物を提供するとともに。[Effects of the Invention] According to the present invention, (1) It exhibits fluorescence and has sufficient heat resistance, and can be used in high-temperature environments by, for example, being blended with a high-strength resin with a high melting point. The present invention also provides a novel aromatic compound that can be suitably used for display materials, decorative materials, etc. that can withstand high temperatures.
(2) このような特有の性質を有する芳香族化合物
を、簡単な工程て効率良く製造することかできる、
等の利点を有する芳香族化合物およびその製造方法を提
供することかできる。(2) It is possible to provide an aromatic compound and a method for producing the same, which have the following advantages: an aromatic compound having such unique properties can be efficiently produced using a simple process.
第1図は、この発明の芳香族化合物の一例についての赤
外線吸収スペクトル図である。FIG. 1 is an infrared absorption spectrum diagram of an example of the aromatic compound of the present invention.
Claims (2)
〜6のアルキル基、炭素数1〜6のアルコキシ基、炭素
数6〜8のアリール基、炭素数6〜8のアリールオキシ
基、カルボキシル基およびハロゲン原子のいずれかであ
り、R^3は炭素数1〜6のアルキル基、炭素数1〜6
のアルコキシ基、炭素数6〜8のアリール基、炭素数6
〜8のアリールオキシ基のいずれかであり、mおよびn
は、それぞれ0および1〜4の整数のいずれかであり、
pは0および1〜5の整数のいずれかである.}で表わ
される芳香族化合物.(1) The following formula [I]: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ {However, in formula [I], R^1 and R^2 are the number of carbon atoms l
-6 alkyl group, C1-6 alkoxy group, C6-8 aryl group, C6-8 aryloxy group, carboxyl group, and halogen atom, and R^3 is carbon Alkyl group having 1 to 6 carbon atoms, 1 to 6 carbon atoms
alkoxy group, aryl group having 6 to 8 carbon atoms, 6 carbon atoms
~8 aryloxy groups, m and n
are each an integer of 0 and 1 to 4,
p is either 0 or an integer from 1 to 5. } aromatic compound.
前記と同じ意味である.} で表わされるフェノールフタリン類と、 次式[III]: ▲数式、化学式、表等があります▼ {ただし、式[III]中、R^3およびpは前記と同じ
意味であり、Xはハロゲン原子である.}で表わされる
ハロゲン化芳香族化合物とを反応させることを特徴とす
る請求項1に記載の芳香族化合物の製造方法.(2) The following formula [II]: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ {However, in formula [II], R^1, R^2, m and n have the same meanings as above. } Phenolphthalins represented by the following formula [III]: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ {However, in formula [III], R^3 and p have the same meanings as above, and X It is a halogen atom. } The method for producing an aromatic compound according to claim 1, which comprises reacting the aromatic compound with a halogenated aromatic compound represented by }.
Priority Applications (1)
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JP23206988A JPH0283353A (en) | 1988-09-16 | 1988-09-16 | Aromatic compound and production thereof |
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JP23206988A JPH0283353A (en) | 1988-09-16 | 1988-09-16 | Aromatic compound and production thereof |
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JPH0283353A true JPH0283353A (en) | 1990-03-23 |
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JP23206988A Pending JPH0283353A (en) | 1988-09-16 | 1988-09-16 | Aromatic compound and production thereof |
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JP (1) | JPH0283353A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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JP4866857B2 (en) * | 2004-10-18 | 2012-02-01 | フェデラル−モーグル コーポレイション | Cover assembly |
-
1988
- 1988-09-16 JP JP23206988A patent/JPH0283353A/en active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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JP4866857B2 (en) * | 2004-10-18 | 2012-02-01 | フェデラル−モーグル コーポレイション | Cover assembly |
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