JPH0673018A - Method for synthesizing 4@(3754/24)5)-cyanoimidazole compound - Google Patents
Method for synthesizing 4@(3754/24)5)-cyanoimidazole compoundInfo
- Publication number
- JPH0673018A JPH0673018A JP4253714A JP25371492A JPH0673018A JP H0673018 A JPH0673018 A JP H0673018A JP 4253714 A JP4253714 A JP 4253714A JP 25371492 A JP25371492 A JP 25371492A JP H0673018 A JPH0673018 A JP H0673018A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- mol
- cyanoimidazole
- thiocarbamoylimidazole
- methyl
- 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
- 238000000034 method Methods 0.000 title claims abstract description 16
- 230000002194 synthesizing effect Effects 0.000 title claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 28
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- 150000003863 ammonium salts Chemical class 0.000 claims abstract description 6
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 abstract description 7
- 239000005695 Ammonium acetate Substances 0.000 abstract description 7
- 229940043376 ammonium acetate Drugs 0.000 abstract description 7
- 235000019257 ammonium acetate Nutrition 0.000 abstract description 7
- 150000003839 salts Chemical class 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 239000002243 precursor Substances 0.000 abstract description 4
- 229910001385 heavy metal Inorganic materials 0.000 abstract description 3
- 229910052751 metal Inorganic materials 0.000 abstract description 3
- 239000002184 metal Substances 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 239000003822 epoxy resin Substances 0.000 abstract description 2
- 230000001766 physiological effect Effects 0.000 abstract description 2
- 229920000647 polyepoxide Polymers 0.000 abstract description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 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 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 6
- GSBGWLFUGNVIFB-UHFFFAOYSA-N 2-methyl-1h-imidazole-5-carbonitrile Chemical compound CC1=NC=C(C#N)N1 GSBGWLFUGNVIFB-UHFFFAOYSA-N 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- MNYPQSNAWPZXRV-UHFFFAOYSA-N 2-methyl-1h-imidazole-5-carbothioamide Chemical compound CC1=NC=C(C(N)=S)N1 MNYPQSNAWPZXRV-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- -1 imidazole compound Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- NWVGXXPWOYZODV-UHFFFAOYSA-N 1h-imidazole-5-carbonitrile Chemical compound N#CC1=CN=CN1 NWVGXXPWOYZODV-UHFFFAOYSA-N 0.000 description 2
- VDTBNINWTLTCFW-UHFFFAOYSA-N 2-phenyl-1h-imidazole-5-carbonitrile Chemical compound N#CC1=CNC(C=2C=CC=CC=2)=N1 VDTBNINWTLTCFW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- MMVILKIFGQPOLE-UHFFFAOYSA-N diazanium;carbonate;hydrate Chemical compound [NH4+].[NH4+].[OH-].OC([O-])=O MMVILKIFGQPOLE-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- QMQZIXCNLUPEIN-UHFFFAOYSA-N 1h-imidazole-2-carbonitrile Chemical class N#CC1=NC=CN1 QMQZIXCNLUPEIN-UHFFFAOYSA-N 0.000 description 1
- CUOPCGNBQZKKNU-UHFFFAOYSA-N 1h-imidazole-5-carbothioamide Chemical compound NC(=S)C1=CN=CN1 CUOPCGNBQZKKNU-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明方法により得られる4(5)−
シアノイミダゾール化合物は、生理活性が期待される4
(5)−アミノメチルイミダゾール化合物、4(5)−〔イミ
ダゾリニール−(2')〕−イミダゾール化合物及び4(5)−
〔イミダゾリール−(2')〕−イミダゾール化合物等の前
駆体となり、またエポキシ樹脂の硬化剤として有用な4
(5)−〔2',4' −ジアミノ−ｓ−トリアジニール−
(6')〕−イミダゾール化合物の前駆体となるものであ
る。Industrial field: 4 (5) -obtained by the method of the present invention
Cyanoimidazole compounds are expected to have physiological activity 4
(5) -Aminomethylimidazole compound, 4 (5)-[imidazolinyl- (2 ')]-imidazole compound and 4 (5)-
[Imidazolyl- (2 ')]-is a precursor of imidazole compounds and is also useful as a curing agent for epoxy resins.
(5)-[2 ', 4'-diamino-s-triazinyl-
(6 ')]-is a precursor of the imidazole compound.
【０００２】[0002]
【従来の技術】4(5)−シアノイミダゾール化合物の合成
方法として、本発明者等は先に特開平３−１９７４６５
号公報において、4(5)−チオカルバモイルイミダゾール
化合物を金属塩錯体となし、これを塩基の存在下に加熱
して目的物を得る方法を提案した。この方法の出発原料
となる4(5)−チオカルバモイルイミダゾール化合物は、
加圧下においてイミダゾール−4(5)−ジチオカルボン酸
化合物とアンモニア水を反応させて得られるものであ
る。（特開平３−１３５９６２号公報）2. Description of the Related Art As a method for synthesizing a 4 (5) -cyanoimidazole compound, the inventors of the present invention have previously disclosed JP-A-3-197465.
In the publication, a method was proposed in which a 4 (5) -thiocarbamoylimidazole compound was formed into a metal salt complex, which was heated in the presence of a base to obtain the desired product. The 4 (5) -thiocarbamoylimidazole compound that is the starting material for this method is
It is obtained by reacting an imidazole-4 (5) -dithiocarboxylic acid compound with ammonia water under pressure. (JP-A-3-135962)
【０００３】[0003]
【発明が解決しようとする課題】前記の特開平３−１９
４７６５号公報に記載の方法自体は簡単で優れたものと
思われるが、容易に廃棄できない重金属塩を使用しなけ
ればならないという欠点がある。この重金属塩を使用し
ない4(5)−シアノイミダゾール化合物の合成方法を提供
することが本発明の目的である。DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention
Although the method itself described in Japanese Patent No. 4765 seems to be simple and excellent, it has a drawback that a heavy metal salt that cannot be easily discarded must be used. It is an object of the present invention to provide a method for synthesizing a 4 (5) -cyanoimidazole compound that does not use this heavy metal salt.
【０００４】[0004]
【課題を解決するための手段】本発明者等は、種々の試
験研究を行った結果、4(5)−チオカルバモイルイミダゾ
ール化合物とアンモニウム塩をジメチルスルフォキシド
と共に加熱することにより、金属塩を用いることなく、
目的物の4(5)−シアノイミダゾール化合物が得られるこ
とを見い出し、本発明方法を完遂するに至った。Means for Solving the Problems As a result of conducting various test studies, the present inventors have found that a metal salt is formed by heating a 4 (5) -thiocarbamoylimidazole compound and an ammonium salt together with dimethylsulfoxide. Without using
It was found that a desired 4 (5) -cyanoimidazole compound was obtained, and the method of the present invention was completed.
【０００５】本発明方法の実施において用いられる4(5)
−チオカルバモイルイミダゾール化合物は化１に示され
る化合物であり、例えば特開平３−１３５９６２号公報
に記載の方法によって合成される。4 (5) used in the practice of the method of the present invention
The -thiocarbamoylimidazole compound is a compound represented by Chemical formula 1, and is synthesized by, for example, the method described in JP-A-3-135962.
【０００６】[0006]
【化１】 [Chemical 1]
【０００７】本発明方法の実施において用いられる代表
的なアンモニウム塩は、炭酸アンモニウム１水塩、酢酸
アンモニウム及びイソシアヌル酸アンモニウム等であ
り、いずれも4(5)−チオカルバモイルイミダゾール化合
物に対して２倍モル以上使用される。Typical ammonium salts used in the practice of the method of the present invention are ammonium carbonate monohydrate, ammonium acetate, ammonium isocyanurate and the like, all of which are twice as much as the 4 (5) -thiocarbamoylimidazole compound. Used over moles.
【０００８】本発明方法の実施において用いられるジメ
チルスルフォキシドの使用量は、4(5)−チオカルバモイ
ルイミダゾール化合物に対して１４倍モル以上が好まし
い。The amount of dimethylsulfoxide used in carrying out the method of the present invention is preferably 14 times or more the molar amount of the 4 (5) -thiocarbamoylimidazole compound.
【０００９】本発明方法の実施に当たって夫々所定量の
4(5)−チオカルバモイルイミダゾール化合物、アンモニ
ウム塩及びジメチルスルフォキシドの３者を９５〜１０
０℃の温度において３時間以上加熱して反応させる。反
応終了後、不溶物（主として単体硫黄）を濾別し、濾液
を乾固して得られる乾固物を水で再結晶すると、化２で
示される所期の4(5)−シアノイミダゾール化合物が得ら
れる。In carrying out the method of the present invention, a predetermined amount of
The ratio of 4 (5) -thiocarbamoylimidazole compound, ammonium salt and dimethyl sulfoxide to 95-10
The reaction is carried out by heating at a temperature of 0 ° C. for 3 hours or more. After completion of the reaction, insoluble matter (mainly elemental sulfur) is filtered off, and the dried matter obtained by drying the filtrate is recrystallized with water to give the desired 4 (5) -cyanoimidazole compound represented by the chemical formula 2. Is obtained.
【００１０】[0010]
【化２】 [Chemical 2]
【００１１】本発明方法によって合成される代表的な４
−シアノイミダゾール化合物としては、４−シアノイミ
ダゾール〔m.p. 143〜145 ℃（水）〕、４−シアノ−２
−メチルイミダゾール〔m.p. 236〜238 ℃（水）〕、４
−シアノ−２−フェニルイミダゾール〔m.p. 180〜181
℃（水）〕、4(5)−シアノ−２，5(4)−ジメチルイミダ
ゾール〔m.p. 164〜165 ℃（水）〕が挙げられる。Representative 4 synthesized by the method of the present invention
-Cyanoimidazole compounds include 4-cyanoimidazole [mp 143-145 ° C (water)], 4-cyano-2
-Methylimidazole [mp 236-238 ° C (water)], 4
-Cyano-2-phenylimidazole [mp 180-181
C. (water)], 4 (5) -cyano-2,5 (4) -dimethylimidazole [mp 164-165 ° C. (water)].
【００１２】[0012]
【作用】4(5)−チオカルバモイルイミダゾール化合物と
4(5)−シアノイミダゾール化合物の間には化３で示され
る平衡関係があると言われている。生成系のＨ2 Ｓをジ
メチルスルフォキシドを用いて酸化して水と単体硫黄に
変えることにより、平衡は生成系側に移り、目的物4(5)
−シアノイミダゾール化合物が得られるものと考えられ
る。[Function] With 4 (5) -thiocarbamoylimidazole compound
It is said that the 4 (5) -cyanoimidazole compound has an equilibrium relationship shown in Chemical formula 3. By oxidizing H 2 S in the production system with dimethyl sulfoxide and converting it into water and elemental sulfur, the equilibrium shifts to the production system side, and the target compound 4 (5)
It is believed that a cyanoimidazole compound is obtained.
【００１３】[0013]
【化３】 [Chemical 3]
【００１４】[0014]
（実施例１）４−チオカルバモイルイミダゾール２．５
ｇ（0.02モル）、酢酸アンモニウム６．２ｇ（0.08モ
ル）及びジメチルスルフォキシド２０ｍｌ（0.28モル）
を９５〜１００℃の温度で５時間加熱したのち、不溶物
除去のために反応混合物を濾過し、濾液を乾固し、乾固
物を水で再結晶し、粗目的物の４−シアノイミダゾール
０．７３ｇ（粗収率39モル％）を得た。(Example 1) 4-thiocarbamoyl imidazole 2.5
g (0.02 mol), ammonium acetate 6.2 g (0.08 mol) and dimethyl sulfoxide 20 ml (0.28 mol)
Was heated at a temperature of 95 to 100 ° C. for 5 hours, the reaction mixture was filtered to remove insolubles, the filtrate was evaporated to dryness, and the dried solid was recrystallized from water to give the crude 4-cyanoimidazole as a crude product. 0.73 g (crude yield 39 mol%) was obtained.
【００１５】（実施例２）２−メチル−４−チオカルバ
モイルイミダゾール２．８ｇ（0.02モル）、酢酸アンモ
ニウム３．１ｇ（0.04モル）及びジメチルスルフォキシ
ド２０ｍｌ（0.28モル）を９５〜１００℃の温度で５時
間加熱したのち、実施例１と同様の後処理を行い、粗目
的物の２−メチル−４−シアノイミダゾール１．８ｇ
（収率84モル％）を得た。Example 2 2.8 g (0.02 mol) of 2-methyl-4-thiocarbamoylimidazole, 3.1 g (0.04 mol) of ammonium acetate and 20 ml (0.28 mol) of dimethyl sulfoxide were added at 95 to 100 ° C. After heating at the temperature for 5 hours, the same post-treatment as in Example 1 was performed to obtain 1.8 g of the crude target product, 2-methyl-4-cyanoimidazole.
(Yield 84 mol%) was obtained.
【００１６】（実施例３）２−メチル−４−チオカルバ
モイルイミダゾール２．８ｇ（0.02モル）、炭酸アンモ
ニウム１水塩４．６ｇ（0.04モル）及びジメチルスルフ
ォキシド２０ｍｌ（0.28モル）を９５〜１００℃の温度
で５時間加熱したのち、実施例１と同様の後処理を行い
粗目的物の２−メチル−４−シアノイミダゾール０．６
５ｇ（収率30モル％）を得た。Example 3 2.8 g (0.02 mol) of 2-methyl-4-thiocarbamoylimidazole, 4.6 g (0.04 mol) of ammonium carbonate monohydrate and 20 ml (0.28 mol) of dimethylsulfoxide were added to 95-90 parts. After heating at a temperature of 100 ° C. for 5 hours, the same post-treatment as in Example 1 was carried out to give the crude product of 2-methyl-4-cyanoimidazole 0.6.
5 g (yield 30 mol%) was obtained.
【００１７】（実施例４）２−メチル−４−チオカルバ
モイルイミダゾール２．８ｇ（0.02モル）、酢酸アンモ
ニウム６．２ｇ（0.08モル）及びジメチルスルフォキシ
ド２０ｍｌ（0.28モル）を９５〜１００℃の温度で３時
間加熱したのち、、実施例１と同様の後処理を行い、粗
目的物の２−メチル−４−シアノイミダゾール１．１２
ｇ（収率52モル％）を得た。(Example 4) 2.8 g (0.02 mol) of 2-methyl-4-thiocarbamoylimidazole, 6.2 g (0.08 mol) of ammonium acetate and 20 ml (0.28 mol) of dimethyl sulfoxide were added at 95-100 ° C. After heating at a temperature for 3 hours, the same post-treatment as in Example 1 was performed to give the crude target product 2-methyl-4-cyanoimidazole 1.12.
g (yield 52 mol%) was obtained.
【００１８】（実施例５）２−メチル−４−チオカルバ
モイルイミダゾール２．８ｇ（0.02モル）、イソシアヌ
ール酸アンモニウム１水塩４．９ｇ（0.03モル）及びジ
メチルスルフォキシド２０ｍｌ（0.28モル）を９５〜１
００℃の温度で５時間加熱したのち、反応混合物を濾過
し、濾液を乾固し、乾固物を熱アセトンを用いて抽出
し、抽出液を乾固し、乾固物を水を用いて再結晶して粗
目的物２−メチル−４−シアノイミダゾール１．７ｇ
（粗収率79モル％）を得た。(Example 5) 2.8 g (0.02 mol) of 2-methyl-4-thiocarbamoylimidazole, 4.9 g (0.03 mol) of ammonium isocyanurate monohydrate and 20 ml (0.28 mol) of dimethyl sulfoxide were added. 95-1
After heating at a temperature of 00 ° C. for 5 hours, the reaction mixture was filtered, the filtrate was evaporated to dryness, the dried solid was extracted with hot acetone, the extract was dried to dryness, and the dried solid was dried with water. Recrystallized crude product 2-methyl-4-cyanoimidazole 1.7 g
(Crude yield 79 mol%) was obtained.
【００１９】（実施例６）２−フェニル−４−チオカル
バモイミダゾール４．１ｇ（0.02モル）、酢酸アンモニ
ウム６．２ｇ（0.08モル）及びジメチルスルフォキシド
２０ｍｌ（0.28モル）を９５〜１００℃の温度で５時間
加熱したのち、反応混合物を濾過し、濾液を乾固し、乾
固物を熱メタノール抽出し、抽出液を乾固し、乾固物を
水を用いて再結晶して粗目的物の２−フェニル−４−シ
アノイミダゾール２．０４ｇ（粗収率60モル％）を得
た。Example 6 4.1 g (0.02 mol) of 2-phenyl-4-thiocarbamoimidazole, 6.2 g (0.08 mol) of ammonium acetate and 20 ml (0.28 mol) of dimethyl sulfoxide were added at 95 to 100 ° C. After heating at the temperature of 5 hours, the reaction mixture was filtered, the filtrate was evaporated to dryness, the dried solid was extracted with hot methanol, the extract was evaporated to dryness, and the dried solid was recrystallized with water to obtain a crude product. 2.04 g (crude yield 60 mol%) of 2-phenyl-4-cyanoimidazole of the target product was obtained.
【００２０】（実施例７）2,4(5)−ジメチル−5(4)−チ
オカルバモイルイミダゾール２．８ｇ（0.02モル）、酢
酸アンモニウム６．２ｇ（0.08モル）及びジメチルスル
フォキシド２０ｍｌ（0.28モル）を９５〜１００℃の温
度で３時間加熱したのち、、実施例１と同様の後処理を
行い、粗目的物の2,4(5)−ジメチル−5(4)−シアノイミ
ダゾール０．９８ｇ（収率46モル％）を得た。(Example 7) 2.8 g (0.02 mol) of 2,4 (5) -dimethyl-5 (4) -thiocarbamoylimidazole, 6.2 g (0.08 mol) of ammonium acetate and 20 ml (0.28 mol) of dimethyl sulfoxide. Of the crude product, 2,4 (5) -dimethyl-5 (4) -cyanoimidazole. 98 g (yield 46 mol%) was obtained.
Claims (1)
合物とアンモニウム塩をジメチルスルフォキシドと共に
加熱することを特徴とする4(5)−シアノイミダゾール化
合物の合成方法。1. A method for synthesizing a 4 (5) -cyanoimidazole compound, which comprises heating a 4 (5) -thiocarbamoylimidazole compound and an ammonium salt together with dimethylsulfoxide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4253714A JPH0673018A (en) | 1992-08-27 | 1992-08-27 | Method for synthesizing 4@(3754/24)5)-cyanoimidazole compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4253714A JPH0673018A (en) | 1992-08-27 | 1992-08-27 | Method for synthesizing 4@(3754/24)5)-cyanoimidazole compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0673018A true JPH0673018A (en) | 1994-03-15 |
Family
ID=17255131
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4253714A Pending JPH0673018A (en) | 1992-08-27 | 1992-08-27 | Method for synthesizing 4@(3754/24)5)-cyanoimidazole compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0673018A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7919219B2 (en) | 2004-11-24 | 2011-04-05 | Hodogaya Chemical Co., Ltd. | Electrophotographic photosensitive body |
| US8486594B2 (en) | 2006-01-25 | 2013-07-16 | Hodogaya Chemical Co., Ltd. | P-terphenyl compound mixture and electrophotographic photoreceptors made by using the same |
-
1992
- 1992-08-27 JP JP4253714A patent/JPH0673018A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7919219B2 (en) | 2004-11-24 | 2011-04-05 | Hodogaya Chemical Co., Ltd. | Electrophotographic photosensitive body |
| US8486594B2 (en) | 2006-01-25 | 2013-07-16 | Hodogaya Chemical Co., Ltd. | P-terphenyl compound mixture and electrophotographic photoreceptors made by using the same |
| US8673792B2 (en) | 2006-01-25 | 2014-03-18 | Hodogaya Chemical Co., Ltd. | p-Terphenyl compound mixture and electrophotographic photoreceptors made by using the same |
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