JPH02184665A - Phthalonitrile-based compound and production thereof - Google Patents
Phthalonitrile-based compound and production thereofInfo
- Publication number
- JPH02184665A JPH02184665A JP368489A JP368489A JPH02184665A JP H02184665 A JPH02184665 A JP H02184665A JP 368489 A JP368489 A JP 368489A JP 368489 A JP368489 A JP 368489A JP H02184665 A JPH02184665 A JP H02184665A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- group
- phthalonitrile
- parts
- 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 19
- 229920006391 phthalonitrile polymer Polymers 0.000 title claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 title abstract description 6
- -1 phthalocyanine compound Chemical class 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 abstract description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 6
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 5
- 230000003287 optical effect Effects 0.000 abstract description 4
- 239000010409 thin film Substances 0.000 abstract description 4
- 230000005693 optoelectronics Effects 0.000 abstract description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000005110 aryl thio group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-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
- NAAMXDTVYZTNQQ-UHFFFAOYSA-N 3,4-dichlorobenzene-1,2-dicarbonitrile Chemical compound ClC1=CC=C(C#N)C(C#N)=C1Cl NAAMXDTVYZTNQQ-UHFFFAOYSA-N 0.000 description 1
- XOHYJKFIHOYQKA-UHFFFAOYSA-N 4,5-bis(phenylsulfanyl)benzene-1,2-dicarbonitrile Chemical compound C=1C=CC=CC=1SC=1C=C(C#N)C(C#N)=CC=1SC1=CC=CC=C1 XOHYJKFIHOYQKA-UHFFFAOYSA-N 0.000 description 1
- SRIJSZQFAMLVQV-UHFFFAOYSA-N 4,5-dichlorobenzene-1,2-dicarbonitrile Chemical compound ClC1=CC(C#N)=C(C#N)C=C1Cl SRIJSZQFAMLVQV-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000005336 safety glass Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
- C09B47/067—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
- C09B47/0675—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile having oxygen or sulfur linked directly to the skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、新規なフタロニトリル系化合物に関し、光記
録媒体、光カード、レーザープリンター、近赤外線吸収
フィルター、保護眼鏡などのオプトエレクトロニクス材
料として用いられる新規フタロシアニン化合物の中間体
として利用される。[Detailed Description of the Invention] [Field of Industrial Application] The present invention relates to a new phthalonitrile compound, which can be used as an optoelectronic material for optical recording media, optical cards, laser printers, near-infrared absorption filters, safety glasses, etc. It is used as an intermediate for new phthalocyanine compounds.
〔従来の技術］
３、４．５．６−アリールチオフタロニトリル、３．６
〜ジアルコキシフタロニトリルは公知であるが、選択的
位置にアルコキシ基と、これ以外の置換基を有するフタ
ロシアニン系化合物およびその製造方法は現在知られて
いない。[Prior art] 3,4.5.6-arylthiophthalonitrile, 3.6
Although dialkoxyphthalonitriles are known, phthalocyanine compounds having an alkoxy group and other substituents at selective positions and methods for producing the same are currently unknown.
［発明が解決しようとする課題］
本発明は選択的位置にアルコキシ基とアリールチオ基な
有する新規なフタロニトリル系化合物及びその製造方法
を提供するものである。[Problems to be Solved by the Invention] The present invention provides a novel phthalonitrile compound having an alkoxy group and an arylthio group at selective positions, and a method for producing the same.
本発明の第１の発明は、式（Ｉ）
Ｒ
Ｕｔ＋
Ｅ弐 （Ｉ）中、Ｒは直鎖又は分岐のアルキル基を表わ
し、Ｒｏは未置換又は置換アリール基を表わす。］で表
わされるフタロニトリル系化合物である。The first aspect of the present invention is the formula (I) R Ut+ E2 (I), where R represents a linear or branched alkyl group, and Ro represents an unsubstituted or substituted aryl group. ] It is a phthalonitrile compound represented by.
本発明の第２の発明は式ＣＩ）で表わされる化合物の製
造方法であって、
一般式（ＩＩ）
Ｒ
Ｕに
［式（ＩＩ）中、Ｒは直鎖又は分岐のアルキル基を表わ
す、］で表わされる３、６−ジアルコキシ−４，５−ジ
クロロフタロニトリルと一般式（ＩＩ［）ｐｏｓｈ
（ｍ）
〔式（Ｉｎ）中、Ｒｏは未置換又は置換アリール基を表
わす、〕で表わされる化合物を塩基の存在下で反応させ
て製造する方法である。The second invention of the present invention is a method for producing a compound represented by formula (CI), in which the general formula (II) R U [in formula (II), R represents a linear or branched alkyl group] 3,6-dialkoxy-4,5-dichlorophthalonitrile represented by the general formula (II[)posh
(m) A method for producing a compound represented by [In formula (In), Ro represents an unsubstituted or substituted aryl group] in the presence of a base.
式（Ｉ）、 （ＩＩＩ中のＲの直鎖のアルキル基の例
としては、メチル基、エチル基、ｎ−プロピル基、ロー
ブチル基、ローペンチル基、ｎ−ヘキシル基、ｎ−へブ
チル基、オクチル基、ドデシル基などが挙げられ、分岐
のアルキル基の例としては、１ｓｏ−プロピル基、ｉｓ
吋アミル基、２．２−ジメチルプロピル基、２−エチル
ヘキシル基、３．５．５−トリメチルヘキシル基などが
挙げられる。Examples of the straight chain alkyl group for R in formula (I), (III) include methyl group, ethyl group, n-propyl group, lobetyl group, loopentyl group, n-hexyl group, n-hebutyl group, octyl group. Examples of branched alkyl groups include 1so-propyl group, iso-propyl group, and dodecyl group.
Examples thereof include a 2-amyl group, a 2,2-dimethylpropyl group, a 2-ethylhexyl group, and a 3,5,5-trimethylhexyl group.
式 （Ｉ）、 （ＩＩＩ）中のＲｏの未置換又は置換
アリール基の例としては、フェニル基、４−ｔｅｒｔ−
ブチルフェニル基、４−ニトロフェニル基、α−ナフチ
ル基、β−ナフチル基などが挙げられる。Examples of the unsubstituted or substituted aryl group for Ro in formulas (I) and (III) include phenyl group, 4-tert-
Examples include butylphenyl group, 4-nitrophenyl group, α-naphthyl group, β-naphthyl group, and the like.
また塩基としてはＫＯＨ，ＮａＯＨ，にａｃｔｓ、 Ｎ
ａＨＣＯ３゜ＫＨＣＯ３，ＮａＨＣＯ３，Ｃ）ＩｓＣＯ
ＯＮａなどが挙げられる。Also, as bases, KOH, NaOH, acts, N
aHCO3゜KHCO3, NaHCO3, C) IsCO
Examples include ONa.
前記反応は溶媒中で行われる。用いる溶媒の例としては
、アセトン、ジエチルケトン、メチルエチルケトン、シ
クロヘキサノンなどのケトン系溶媒、ジメチルホルムア
ミド、Ｎ、Ｎ−ジメチルアセトアミド、ジメチルスルホ
キシド、ジメチルイミダゾリジノン、Ｎ−メチルピロリ
ドンなどの非プロトン性極性溶媒が挙げられ、これは単
独又は水との混合系で用いることができその含水率は３
０％以下が好ましい、また使用する溶媒の量は化合物（
ＩＩ）１モルに対し１００ｎ＋ｊ２〜１００Ｊ２であり
、好ましくは１〜１０βである。The reaction is carried out in a solvent. Examples of solvents used include ketone solvents such as acetone, diethyl ketone, methyl ethyl ketone, and cyclohexanone, and aprotic polar solvents such as dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, dimethylimidazolidinone, and N-methylpyrrolidone. It can be used alone or in a mixed system with water, and its water content is 3.
The amount of solvent used is preferably 0% or less, and the amount of solvent used is
II) 100n+j2 to 100J2 per mole, preferably 1 to 10β.
この反応で使用する式（ＩＩＩ）で表される化合物の量
は、化合物（ＩＩ）に対して１．５〜４．０モル比、好
ましくは１．８〜２．５モル比であり、塩基の使用量は
化合物 （ＩＩ）に対して１．５〜４．０モル比、好ま
しくは１．８〜２．５モル比である０反応温度はＯ℃〜
溶媒の還流温度であり、好ましくは５０℃〜溶媒の還流
温度である０反応時間は５分〜４時間が好ましい、また
化合物 （ＩＩ）は化合物（ＩＶ） と一般式 （Ｖ
）
〔式（Ｖ）中のＲは、式（ＩＩ）中のＲと同一の意味を
表わし、ＸはＦ、 Ｃ１，Ｂｒ、 １などのハロゲン原
子またはｐ−トルエンスルホニルオキシ基などのアリー
ルスルホニルオキシ基を表わす。〕で表わされる化合物
をに２Ｃ０３などの塩基の存在下、反応させることによ
り得ることができる。The amount of the compound represented by formula (III) used in this reaction is 1.5 to 4.0 molar ratio, preferably 1.8 to 2.5 molar ratio to compound (II), and the base The amount used is 1.5 to 4.0 molar ratio, preferably 1.8 to 2.5 molar ratio with respect to compound (II).The reaction temperature is 0°C to
The reflux temperature of the solvent is preferably 50°C to the reflux temperature of the solvent. The reaction time is preferably 5 minutes to 4 hours. Compound (II) is a compound (IV) with general formula (V
) [R in formula (V) represents the same meaning as R in formula (II), and X is a halogen atom such as F, C1, Br, 1, or arylsulfonyloxy such as p-toluenesulfonyloxy group represents a group. It can be obtained by reacting a compound represented by ] in the presence of a base such as 2C03.
本発明のフタロニトリル化合物から誘導されるフタロシ
アニンは、樹脂上に薄膜を形成させると、既知のフタロ
シアニンの薄膜と比較してすぐれた反射率を示す。The phthalocyanine derived from the phthalonitrile compound of the present invention, when formed into a thin film on a resin, exhibits superior reflectivity compared to known phthalocyanine thin films.
［実施例］ 以下本発明を実施例により、さらに詳細に説明する。[Example] The present invention will be explained in more detail below using Examples.
実施例中の部および％はすべで重量部、重量％を示す。All parts and percentages in the examples indicate parts by weight and percentages by weight.
実施例−１
ＫＯＨ１２，３部、チオフェノール２４２部、水５３部
よりなる混合物に３．６−シオクチルオキシー４．５−
ジクロルフタロニトリル４５．３部とアセトン４００部
よりなる溶液を５０℃以下で滴下した。その後５５〜６
０℃で２時間加熱攪拌した０反応液を濃縮し、トルエン
により抽出を行い、濃縮後カラムクロマトグラフィーに
より精製し、３．６−シオクチルオキシー４．５−ジフ
ェニルチオフタロニトリル５４．１部（収率９０％）を
得た。Example-1 3.6-shioctyloxy-4.5-
A solution consisting of 45.3 parts of dichlorophthalonitrile and 400 parts of acetone was added dropwise at below 50°C. then 55-6
The reaction solution heated and stirred at 0°C for 2 hours was concentrated, extracted with toluene, and purified by column chromatography after concentration to obtain 54.1 parts of 3.6-cyoctyloxy-4.5-diphenylthiophthalonitrile ( A yield of 90% was obtained.
元素分析 Ｃｓ６Ｈ４４Ｎ２０ｚＳｘ実測値（％）
７１．７１ ７．２４ ４．７０ １０．４９ＨＭ
Ｒ（ＣＤＣ１３）δ： ７．１７（ｓ、１０Ｈ）、
４．０８（ｔ、４旧。Elemental analysis Cs6H44N20zSx actual value (%)
71.71 7.24 4.70 10.49HM
R (CDC13) δ: 7.17 (s, 10H),
4.08 (t, 4 old.
２、（ＩＱ 〜Ｏ，Ｂ３（ｍ、２４Ｈ）、 ０．９０
（ｔ、６Ｈ）ＩＲ（ｎｅａｔ）ｃｍ−’： ２２３０
実施例−２
ＫＯ）１１２．３部、チオフェノール２４．２部、水５
３部よりなる混合物に３．６−ジｎ−ペンチルオキシ−
４，５−ジクロルフタロニトリル３６．８部とアセトン
４００部よりなる溶液を５０℃以下で滴下した。その後
５５〜６０℃で２時間加熱攪拌した０反応液を濃縮し、
トルエンにより抽出を行い、濃縮後カラムクロマトグラ
フィーにより精製し、３．６−ジｎ−ペンチルオキシ−
４，５−ジフェニルチオフタロニトリル４６．０部（収
率８９％）を得た。2, (IQ ~O, B3 (m, 24H), 0.90
(t,6H)IR(neat)cm-': 2230
Example-2 KO) 112.3 parts, thiophenol 24.2 parts, water 5
3,6-di-n-pentyloxy-
A solution consisting of 36.8 parts of 4,5-dichlorophthalonitrile and 400 parts of acetone was added dropwise at 50°C or lower. Thereafter, the 0 reaction solution was heated and stirred at 55 to 60°C for 2 hours, and concentrated.
Extraction was performed with toluene, and after concentration, purification was performed by column chromatography to obtain 3,6-di-n-pentyloxy-
46.0 parts (yield: 89%) of 4,5-diphenylthiophthalonitrile were obtained.
元素分析 Ｃ８゜ＨｓＪ＊Ｏ□Ｓ２
実測値（％） ６９．６１ ６．２０ ５．３４
１２．３８ＨＭＲ（ＣＤＣｌ２）δ： ７．１３（ｓ
、ｌ０Ｈ）、 ４．０７（ｔ、４Ｈ）。Elemental analysis C8゜HsJ*O□S2 Actual value (%) 69.61 6.20 5.34
12.38HMR(CDCl2)δ: 7.13(s
, 10H), 4.07(t, 4H).
２、００〜１．０３ （ｍ、 １２Ｈ） 、 ０．８
９ （ｔ、 ６Ｈ）ＩＲ（ｎｅａｔ）ｃｍ−’： ２
２３０実施例−３
にＯＨ１２，３部、チオフェノール２４．２部、水５３
部よりなる混合物に３．６−ジ（２−エチルへキシルオ
キシ）−４，５−ジクロルフタロニトリル４５．２部と
アセトン４００部よりなる溶液を５０℃以下で滴下した
。2,00~1.03 (m, 12H), 0.8
9 (t, 6H)IR(neat)cm-': 2
230 Example-3 12.3 parts of OH, 24.2 parts of thiophenol, 53 parts of water
A solution of 45.2 parts of 3,6-di(2-ethylhexyloxy)-4,5-dichlorophthalonitrile and 400 parts of acetone was added dropwise to the mixture at 50° C. or lower.
その後５５〜６０℃で２時間加熱攪拌した。反応液を濃
縮し、トルエンにより抽出を行い、濃縮後カラムクロマ
トグラフィーにより精製し、３，６−ジ（２−エチルへ
キシルオキシ）−４，５−ジフェニルチオフタロニトリ
ル４８．２部（収率８０％）を得た。Thereafter, the mixture was heated and stirred at 55 to 60°C for 2 hours. The reaction solution was concentrated, extracted with toluene, and purified by column chromatography to obtain 48.2 parts of 3,6-di(2-ethylhexyloxy)-4,5-diphenylthiophthalonitrile (yield: 80 %) was obtained.
元素分析 Ｃ５ａＨ４ＪｚＯ□Ｓ２
実測値（％） ７１．６９ ７．３６ ４．６９
１０．５３ＨＭＲ（ＣＤＣｌ２）δ： ７．１７（ｓ
、１ＯＮ）、 ４．０４（ｄ、４Ｈ）。Elemental analysis C5aH4JzO□S2 Actual value (%) 71.69 7.36 4.69
10.53HMR(CDCl2)δ: 7.17(s
, 1ON), 4.04(d, 4H).
１、９７〜０．６６ （ｍ、 １８）１） 、 ０．
９７ （ｔ、 ６Ｈ） 。1,97-0.66 (m, 18)1), 0.
97 (t, 6H).
０、８７ （ｔ、 ６Ｈ）
ＩＲ（ｎｅａｔ） ｃｍ−’ ： ２２３０実施例−
４
に叶１２．３部、チオフェノール２４．２部、水５３部
よりなる混合物に３．６−ジ（Ｉｓｏ−アミルオキシ）
−４，５−ジクロルフタロニトリル３６．８部とアセト
ン４００部よりなる溶液を５０℃以下で滴下した。その
後５５〜６０℃で２時間加熱攪拌した０反応液を濃縮し
、トルエンにより抽出を行い、濃縮後カラムクロマトグ
ラフィーにより精製し、３．６−ジ（ｉｓｏ−アルミオ
キシ）−４，５−ジフェニルチオフタロニトリル４９．
３部（収率９５％）を得た。0,87 (t, 6H) IR (neat) cm-': 2230 Example-
4. Add 3.6-di(Iso-amyloxy) to a mixture consisting of 12.3 parts of nifoli, 24.2 parts of thiophenol, and 53 parts of water.
A solution consisting of 36.8 parts of -4,5-dichlorophthalonitrile and 400 parts of acetone was added dropwise at 50°C or lower. Thereafter, the reaction solution was heated and stirred at 55 to 60°C for 2 hours, concentrated, extracted with toluene, and purified by column chromatography after concentration. Thiophthalonitrile 49.
Three parts (95% yield) were obtained.
元素分析 Ｃ５゜Ｈ３２Ｎ２０□Ｓ２実測値（％）６
９．７１ ６．１９ ５．３９ １２．４２ＨＭＲ（Ｃ
ＤＣＩｇ）δ： ７．１８（ｓ、１０１−１）、
４．１２（ｔ、４Ｈ）。Elemental analysis C5゜H32N20□S2 actual value (%) 6
9.71 6.19 5.39 12.42HMR(C
DCIg) δ: 7.18 (s, 101-1),
4.12 (t, 4H).
２．２０〜１．１７（ｍ、６Ｈ）、 ０．８６（ｄ、
１２）１）実施例５〜１３
各実施例において、一般式（ＩＩ）
ｎＩ？
ｕｌ（
中のＲが表−１に示される化合物と、一般式％式％（）
中のＲｏが表−１に示される化合物より、一般式（Ｉ）
Ｒ
のＲおよびＲｏがそれぞれ表−１に示される化合物を合
成した。使用した塩基の種類、反応の条件及び収率を表
−１に記す。2.20-1.17 (m, 6H), 0.86 (d,
12) 1) Examples 5 to 13 In each example, general formula (II) nI? From a compound in which R in ul ( is shown in Table 1) and a compound in which Ro in the general formula % formula % ( The compound shown in was synthesized.The type of base used, reaction conditions, and yield are listed in Table 1.
ＩＲ（にＢｒ）ａｍ−’： ２２３０上記使用物質の
割合は、フタロニトリル１モルに対し、Ｒ’ＳＨおよび
塩基ともに２．２モルで実施例１〜４と同じである。溶
媒はフタロニトリル１モル当り、アセトン、水の場合は
それぞれ５Ｉ２゜５００ｍβ、アミド類の場合は５β使
用した。IR(Br)am-': 2230 The ratio of the above substances used is the same as in Examples 1 to 4, with both R'SH and the base being 2.2 mol per 1 mol of phthalonitrile. The solvent used was 5I2°500 mβ for acetone and water, and 5β for amides, per mole of phthalonitrile.
本発明は式（Ｉ）で表わされるような、置換基として選
択的に３．６位にアルコキシ基を、 ４．５位にアリー
ルチオ基な有した新規なフタロニトリル系化合物および
その有利な製造方法を提供する。The present invention provides a novel phthalonitrile compound having an alkoxy group at the 3.6-position and an arylthio group at the 4.5-position as a substituent, as represented by formula (I), and an advantageous method for producing the same. I will provide a.
これらのフタロニトリル系化合物から合成されるフタロ
シアニン化合物の薄膜は、高反射率を有しており、本発
明のフタロニトリル系化合物は色材の中間体として非常
に価値が高い。Thin films of phthalocyanine compounds synthesized from these phthalonitrile compounds have high reflectance, and the phthalonitrile compounds of the present invention are extremely valuable as intermediates for coloring materials.
特許出願人 三井東圧化学株式会社 山本化成株式会社Patent applicant: Mitsui Toatsu Chemical Co., Ltd. Yamamoto Kasei Co., Ltd.
Claims (1)
し、Ｒ’は未置換又は置換アリール基を表わす。〕で表
わされるフタロニトリル系化合物。 ２、一般式（II） ▲数式、化学式、表等があります▼（II） 〔式（II）中、Ｒは直鎖又は分岐のアルキル基を表わす
。〕で表わされる３，６−ジアルコキシ−４，５−ジク
ロロフタロニトリルと一般式（III） Ｒ’ＳＨ（III） 〔式（III）中、Ｒ’は未置換又は置換アリール基を表
わす。〕で表わされる化合物とを塩基の存在下で反応さ
せることを特徴とする請求項１に記載のフタロニトリル
系化合物の製造方法。[Claims] 1. General formula (I) ▲ Includes mathematical formulas, chemical formulas, tables, etc. ▼ (I) [In formula (I), R represents a linear or branched alkyl group, and R' is unsubstituted. Or represents a substituted aryl group. ] A phthalonitrile compound represented by 2. General formula (II) ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ (II) [In formula (II), R represents a linear or branched alkyl group. 3,6-dialkoxy-4,5-dichlorophthalonitrile represented by the general formula (III) R'SH (III) [In the formula (III), R' represents an unsubstituted or substituted aryl group. 2. The method for producing a phthalonitrile compound according to claim 1, wherein the phthalonitrile compound is reacted with a compound represented by the following formula in the presence of a base.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP368489A JPH07103093B2 (en) | 1989-01-12 | 1989-01-12 | Phthalonitrile-based compound and method for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP368489A JPH07103093B2 (en) | 1989-01-12 | 1989-01-12 | Phthalonitrile-based compound and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02184665A true JPH02184665A (en) | 1990-07-19 |
| JPH07103093B2 JPH07103093B2 (en) | 1995-11-08 |
Family
ID=11564229
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP368489A Expired - Lifetime JPH07103093B2 (en) | 1989-01-12 | 1989-01-12 | Phthalonitrile-based compound and method for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07103093B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001042368A1 (en) * | 1999-12-08 | 2001-06-14 | Gentian As | Substituted phthalocyanines and their precursors |
| JP2007169343A (en) * | 2005-12-19 | 2007-07-05 | Nippon Shokubai Co Ltd | Phthalocyanine compound, method for producing the same and application of the same |
-
1989
- 1989-01-12 JP JP368489A patent/JPH07103093B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001042368A1 (en) * | 1999-12-08 | 2001-06-14 | Gentian As | Substituted phthalocyanines and their precursors |
| JP2007169343A (en) * | 2005-12-19 | 2007-07-05 | Nippon Shokubai Co Ltd | Phthalocyanine compound, method for producing the same and application of the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH07103093B2 (en) | 1995-11-08 |
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