JPH0418060A - New aromatic diketodicarboxylic acid and production thereof - Google Patents
New aromatic diketodicarboxylic acid and production thereofInfo
- Publication number
- JPH0418060A JPH0418060A JP12178290A JP12178290A JPH0418060A JP H0418060 A JPH0418060 A JP H0418060A JP 12178290 A JP12178290 A JP 12178290A JP 12178290 A JP12178290 A JP 12178290A JP H0418060 A JPH0418060 A JP H0418060A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- diketodicarboxylic
- acid
- aromatic
- fluoran
- 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
- 239000002253 acid Substances 0.000 title claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 claims abstract description 7
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical class NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical class C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 abstract description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 12
- 239000000463 material Substances 0.000 abstract description 7
- 239000002994 raw material Substances 0.000 abstract description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 4
- 125000000468 ketone group Chemical group 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 238000004040 coloring Methods 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical class Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical class FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- -1 fluoran compound Chemical class 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical class [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- WAVOOWVINKGEHS-UHFFFAOYSA-N 3-(diethylamino)phenol Chemical compound CCN(CC)C1=CC=CC(O)=C1 WAVOOWVINKGEHS-UHFFFAOYSA-N 0.000 description 1
- YGLYYWZISFBCPU-UHFFFAOYSA-N 4-ethoxy-2-methyl-n-phenylaniline Chemical compound CC1=CC(OCC)=CC=C1NC1=CC=CC=C1 YGLYYWZISFBCPU-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Chemical class 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000203 mixture Substances 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
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XROWMBWRMNHXMF-UHFFFAOYSA-J titanium tetrafluoride Chemical class [F-].[F-].[F-].[F-].[Ti+4] XROWMBWRMNHXMF-UHFFFAOYSA-J 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
皮栗上皇机尻立国
本発明は、感熱記録紙や感圧記録紙等の発色性記録材料
に発色性染料として用いられるフルオラン化合物の製造
原料として有用な新規な芳香族ジケトジカルボン酸及び
その製造方法に関する。[Detailed Description of the Invention] The present invention is a novel aromatic compound useful as a raw material for producing fluoran compounds used as color-forming dyes in color-forming recording materials such as heat-sensitive recording paper and pressure-sensitive recording paper. This invention relates to a diketodicarboxylic acid and a method for producing the same.
従来■技歪
従来、例えば、特開昭６２−１６１７５０号公報に記載
されているように、感熱記録紙や感圧記録紙等の記録材
料として、発色性染料である種々のフルオラン化合物が
用いられており、また、種々のフルオラン化合物が提案
されている。Conventional Technique Distortion Conventionally, various fluoran compounds, which are color-forming dyes, have been used as recording materials such as heat-sensitive recording paper and pressure-sensitive recording paper, as described in, for example, Japanese Patent Application Laid-open No. 161750/1983. Various fluoran compounds have also been proposed.
例えば、上記公報には、３−Ｎ−ｎ−プロピルメチル（
又はエチル）アミノ−６−メチル−７−フェニルアミノ
フルオランが提案されている。これらフルオラン化合物
は、ｏ（４−Ｎ−ｎ−プロピルメチルアミノ （又はエ
チル）−２−ヒドロキシベンゾイル）安息香酸と４−エ
トキシ−２−メチルジフェニルアミンとの反応によって
得られる。For example, in the above publication, 3-N-n-propylmethyl (
or ethyl)amino-6-methyl-7-phenylaminofluorane has been proposed. These fluoran compounds are obtained by the reaction of o(4-N-n-propylmethylamino (or ethyl)-2-hydroxybenzoyl)benzoic acid and 4-ethoxy-2-methyldiphenylamine.
しかし、従来、知られているフルオラン化合物はこのよ
うに、殆どが分子中に単一のフルオラン構造を有するも
のである。However, most of the conventionally known fluoran compounds have a single fluoran structure in the molecule.
が”° しようと る１
本発明者らは、特に、近赤外領域での感熱記録材料とし
て有用である分子中に二つのフルオラン構造を有する新
規なフルオラン化合物を傅るべく鋭意研究した結果、そ
のようなフルオラン化合物を製造するための原料として
有用な芳香族ジケトジカルボン酸を見出して、本発明に
至ったものである。As a result of intensive research into a new fluoran compound having two fluoran structures in the molecule, which is particularly useful as a heat-sensitive recording material in the near-infrared region, the present inventors found that The present invention was achieved by discovering an aromatic diketodicarboxylic acid useful as a raw material for producing such fluoran compounds.
従って、本発明は、かかる新規な芳香族ジケトジカルボ
ン酸及びその製造方法を提供することを目的とする。Therefore, an object of the present invention is to provide such a novel aromatic diketodicarboxylic acid and a method for producing the same.
量 を”′するための
本発明による新規な芳香族ジケトジカルボン酸は、一般
式
（式中、Ｒ１及びＲＺは、それぞれ独立に炭素数１〜９
のアルキル基又は炭素数３〜６のシクロアルキル基を示
す。）
で表わされることを特徴とする。The novel aromatic diketodicarboxylic acid according to the present invention for reducing the amount of
represents an alkyl group or a cycloalkyl group having 3 to 6 carbon atoms. ).
上記一般弐において、Ｒ′及びＲ２は、それぞれ独立に
、例えば、メチル基、エチル基、プロピル基、ブチル基
、オクチル基等のアルキル基、シクロヘキシル基等のシ
クロアルキル基を示すが、特に、メチル基、エチル基、
ブチル基等の低級アルキル基やシクロヘキシル基が好ま
しい。In the above General 2, R' and R2 each independently represent, for example, an alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, an octyl group, or a cycloalkyl group such as a cyclohexyl group. group, ethyl group,
Lower alkyl groups such as butyl groups and cyclohexyl groups are preferred.
従って、本発明による芳香族ジケトジカルボン酸の好ま
しい一例として、例えば、Ｒ１及びＲ２が共にエチル基
である２、５−ビス（４”−Ｎ、Ｎ−ジエチルアミノ）
−２゛−ヒドロキシベンゾイル）テレフタル酸を挙げる
ことができる。Therefore, as a preferable example of the aromatic diketodicarboxylic acid according to the present invention, for example, 2,5-bis(4''-N,N-diethylamino) in which R1 and R2 are both ethyl groups.
-2'-Hydroxybenzoyl)terephthalic acid may be mentioned.
本発明によるかかる芳香族ジケトジカルボン酸は、一般
式
（式中、Ｒ１及びＲ２は、それぞれ独立に炭素数１〜９
のアルキル基又は炭素数３〜６のシクロアルキル基を示
す。）
で表わされるｍ−アミノフェノール誘導体と無水ピロメ
リット酸（二無水物）を反応させることによって得るこ
とができる。Such an aromatic diketodicarboxylic acid according to the present invention has the general formula (wherein R1 and R2 each independently have 1 to 9 carbon atoms.
represents an alkyl group or a cycloalkyl group having 3 to 6 carbon atoms. ) It can be obtained by reacting the m-aminophenol derivative represented by the following with pyromellitic anhydride (dianhydride).
例えば、上記ｍ−アミノフェノール誘導体として、既に
知られている化合物であるｍ−Ｎ、Ｎ−ジエチルアミノ
フェノールを用いて、無水ピロメリット酸（二無水物）
と反応させることによって、前記した２、５−ビス（４
’−Ｎ、Ｎ−ジエチルアミノ）−２”−ヒドロキシベン
ゾイル）テレフタル酸を得ることができる。For example, using m-N,N-diethylaminophenol, which is an already known compound, as the m-aminophenol derivative, pyromellitic anhydride (dianhydride)
By reacting with 2,5-bis(4
'-N,N-diethylamino)-2''-hydroxybenzoyl)terephthalic acid can be obtained.
前記一般式で表わされるｍ−アミノフェノール誘導体と
無水ピロメリット酸（二無水物）との反応は、通常、無
水ピロメリット酸とこれに対してほぼ２倍モル量のｍ−
アミノフェノール誘導体とをトルエン、キシレン、メシ
チレン、メチルイソブチルケトン、アセトン、酢酸エチ
ル、ジエチルエーテル、テトラヒドロフラン、ジイソプ
ロピルエーテル、ジフェニルエーテル、ジクロロエタン
、クロロベンゼン、ジクロロベンゼン等の有機溶剤中で
撹拌下に、好ましくは還流温度に加熱することによって
行なわれる。The reaction between the m-aminophenol derivative represented by the above general formula and pyromellitic anhydride (dianhydride) is usually carried out using pyromellitic anhydride and approximately twice the molar amount of m-pyromellitic anhydride.
The aminophenol derivative is mixed with an organic solvent such as toluene, xylene, mesitylene, methyl isobutyl ketone, acetone, ethyl acetate, diethyl ether, tetrahydrofuran, diisopropyl ether, diphenyl ether, dichloroethane, chlorobenzene, dichlorobenzene, etc. under stirring, preferably at reflux temperature. This is done by heating.
反応には、必要に応して、無水塩化亜鉛、四基′化チタ
ン、塩化アルミニウム、三フッ化ホウ素等のようなルイ
ス酸や、硫酸、リン酸等の鉱酸を触媒として用いてもよ
い。このような触媒は、通常、無水ピロメリット酸１モ
ルに対して１〜１０モル、好ましくは２〜８モルの範囲
で用いられる。Lewis acids such as anhydrous zinc chloride, titanium tetrafluoride, aluminum chloride, boron trifluoride, and mineral acids such as sulfuric acid and phosphoric acid may be used as catalysts in the reaction, if necessary. . Such a catalyst is usually used in an amount of 1 to 10 mol, preferably 2 to 8 mol, per 1 mol of pyromellitic anhydride.
反応は、通常、常圧又は加圧下に温度３０〜１６０℃、
好ましくは４０〜１２０℃で４〜２４時間、好ましくは
８〜２０時間にわたって行なわれる。The reaction is usually carried out at a temperature of 30 to 160°C under normal pressure or increased pressure.
It is preferably carried out at 40 to 120°C for 4 to 24 hours, preferably for 8 to 20 hours.
反応終了後、溶剤を減圧下に留去し、得られた固体を濾
過し、洗浄すれば、本発明による芳香族ジケトジカルボ
ン酸を得ることができる。After the reaction is completed, the solvent is distilled off under reduced pressure, and the resulting solid is filtered and washed to obtain the aromatic diketodicarboxylic acid according to the present invention.
光尻夏着来
本発明による芳香族ジケトジカルボン酸は、感圧記録材
料及び感熱記録材料として用いられるフルオラン化合物
の製造原料として有用であり、特に、本発明による芳香
族ジケトジカルボン酸は、分子内に対称的に二組のケト
ン基とカルボキシル基とを有するために、分子内に二つ
のフルオラン構造を有するフルオラン化合物を製造する
ための原料として有用である。The aromatic diketodicarboxylic acid according to the present invention is useful as a raw material for producing fluoran compounds used as pressure-sensitive recording materials and heat-sensitive recording materials. In particular, the aromatic diketodicarboxylic acid according to the present invention is Since it has two sets of ketone groups and carboxyl groups symmetrically in its molecule, it is useful as a raw material for producing a fluoran compound having two fluoran structures in its molecule.
実施班
以下に実施例を挙げて本発明を説明するが、本発明はこ
れら実施例により何ら限定されるものではない。EXAMPLES The present invention will be explained below with reference to Examples, but the present invention is not limited to these Examples in any way.
ｍ−Ｎ、Ｎ−ジエチルアミンフェノール１８ｇと無水ピ
ロメリットＭ（二無水物）１２ｇをトルエン３５０ｇに
加え、撹拌下に１８時間、加熱還流した。この後、得ら
れた反応混合物を冷却し、ロータリー・エバポレータに
てトルエンを留去し、乾固した。18 g of m-N,N-diethylaminephenol and 12 g of anhydrous pyromellit M (dianhydride) were added to 350 g of toluene, and the mixture was heated under reflux for 18 hours with stirring. Thereafter, the resulting reaction mixture was cooled, and toluene was distilled off using a rotary evaporator to dryness.
得られた乾固物をジエチルエーテル１００ｍ１に加えて
、スラリーとし、洗浄した後、濾過して、固体２６．２
ｇを得た。この固体を洗浄メタノールが無色になるま
で、スラリー洗浄を繰返して、２゜５−ビス（４”Ｎ、
Ｎ−ジエチルアミノ）−２゛−ヒドロキシヘンジイル）
テレフタル酸２．３ｇ（収１７．７％）を薄茶色結晶と
して得た。ＨＬＣ純度は９９％以上であった。The obtained dried product was added to 100 ml of diethyl ether to make a slurry, washed, and filtered to obtain a solid of 26.2 ml.
I got g. This solid was washed with 2°5-bis(4”N,
N-diethylamino)-2'-hydroxyhendiyl)
2.3 g (yield: 17.7%) of terephthalic acid was obtained as light brown crystals. HLC purity was greater than 99%.
融点 ３０７℃（分解）
元素分析値
ＣＨＮ
実測値 ６４．００ ５．８９ ５．８５理論値 ６５
．５７ ５．８３ ５．１０質量分析
分子量 ５４９
プロトン核磁気共鳴スペクトル
第１図に示す。帰属は以下のとおりである。Melting point 307℃ (decomposition) Elemental analysis value CHN Actual value 64.00 5.89 5.85 Theoretical value 65
．． 57 5.83 5.10 Mass Spectrometry Molecular Weight 549 Proton Nuclear Magnetic Resonance Spectrum Shown in FIG. The attribution is as follows.
赤外線吸収スペクトル（ｃ「す
３４００： ０Ｈ
２３００−３６００： ＯＨ（ＣＯＯＨ）１７１０：
Ｃ・Ｏ（ＣＯＯＨ）
１６３０： Ｃ・０Infrared absorption spectrum (c 3400: 0H 2300-3600: OH (COOH) 1710:
C・O (COOH) 1630: C・0
第１図は、本発明による２、５−ビス（４’ −Ｎ、
Ｎ−ジエチルアミノ）−２゛−ヒドロキシヘンジイル）
テレフタル酸のプロトン核磁気共鳴スペクトルを示す。
特許出願人 三井石油化学工業株式会社代理人 弁理士
牧 野 逸 部FIG. 1 shows 2,5-bis(4'-N,
N-diethylamino)-2'-hydroxyhendiyl)
The proton nuclear magnetic resonance spectrum of terephthalic acid is shown. Patent applicant Mitsui Petrochemical Industries Co., Ltd. Agent Patent attorney Itsube Makino
Claims (3)
〜９のアルキル基又は炭素数３〜６のシクロアルキル基
を示す。） で表わされることを特徴とする芳香族ジケトジカルボン
酸。(1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R^1 and R^2 each independently have a carbon number of 1
-9 alkyl group or C3-6 cycloalkyl group. ) An aromatic diketodicarboxylic acid represented by:
−２′−ヒドロキシベンゾイル）テレフタル酸。(2) 2,5-bis(4'-N,N-diethylamino)
-2'-hydroxybenzoyl)terephthalic acid.
〜９のアルキル基又は炭素数３〜６のシクロアルキル基
を示す。） で表わされるｍ−アミノフェノール誘導体と無水ピロメ
リット酸を反応させることを特徴とする一般式 ▲数式、化学式、表等があります▼ （式中、Ｒ＾１及びＲ＾２は、前記と同じである。）で
表わされる芳香族ジケトジカルボン酸の製造方法。(3) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R^1 and R^2 each independently have a carbon number of 1
-9 alkyl group or C3-6 cycloalkyl group. ) A general formula characterized by reacting an m-aminophenol derivative represented by pyromellitic anhydride ▲ There are mathematical formulas, chemical formulas, tables, etc. A method for producing an aromatic diketodicarboxylic acid represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12178290A JPH0418060A (en) | 1990-05-11 | 1990-05-11 | New aromatic diketodicarboxylic acid and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12178290A JPH0418060A (en) | 1990-05-11 | 1990-05-11 | New aromatic diketodicarboxylic acid and production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0418060A true JPH0418060A (en) | 1992-01-22 |
Family
ID=14819758
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12178290A Pending JPH0418060A (en) | 1990-05-11 | 1990-05-11 | New aromatic diketodicarboxylic acid and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0418060A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6352254B1 (en) | 1994-05-20 | 2002-03-05 | Fujitsu Limited | Paper sheet manipulating apparatus and paper sheet transaction apparatus |
-
1990
- 1990-05-11 JP JP12178290A patent/JPH0418060A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6352254B1 (en) | 1994-05-20 | 2002-03-05 | Fujitsu Limited | Paper sheet manipulating apparatus and paper sheet transaction apparatus |
| US6357598B1 (en) | 1994-05-20 | 2002-03-19 | Fujitsu Limited | Paper sheet manipulating apparatus and paper sheet transaction apparatus |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0413384B2 (en) | ||
| JPH0418060A (en) | New aromatic diketodicarboxylic acid and production thereof | |
| JP3030472B2 (en) | New fluoran compounds | |
| JP3030473B2 (en) | Method for producing novel fluoran compound | |
| Tabba et al. | Michael-Michael aldol reaction of chalcones with cyanoacetylurea and cyanoacetylpiperidine | |
| JPH069889A (en) | Fluoran compound and its production | |
| KR100208814B1 (en) | Alpha tocopherol 4-aminobenzoic acid ester compounds and preparation thereof | |
| EP0404134B1 (en) | Organosilicon compounds and method for their preparation | |
| Chen et al. | Synthesis of ferrocenoylphenylureas and the crystal structure of FcCONHCONHC6H5 | |
| JP2574711B2 (en) | Method for producing trimethine dye | |
| JP3009245B2 (en) | N-substituted maleimide and method for producing the same | |
| JPH01129068A (en) | High-purity anthraquinone pigment for near-infrared filter | |
| JP3578281B2 (en) | Diphenoquinone compounds | |
| JP2003048873A (en) | Method of producing 4-phthalonitrile derivative | |
| EP0338385B1 (en) | Process for the preparation of n,n'-bis-(2-hydroxy-ethyl)-piperazine | |
| CN113045491A (en) | Preparation method of Lunvatinib and intermediate | |
| Bajji et al. | Synthesis of indeno [2, 1‐b][1, 4] benzothiazine derivatives from 2‐bromoinden‐1‐ones | |
| JPS588388B2 (en) | Jibenza Middle Ino Seizouhouhou | |
| JPH0745263B2 (en) | Laser optical recording medium using anthraquinone-based long wavelength absorbing dye | |
| JPS62273264A (en) | Production of fluoran compound | |
| SU627129A1 (en) | 4-chlorine-5,7-dinitrobenzofurazane as intermidiate product in synthesis of 4-substituted 5,7-dinitrobenzofurazane | |
| JPH03145438A (en) | Selective synthesis of bisphenol compound having ketone skeleton directly bonded to phenol nucleus | |
| JPS63264539A (en) | 2,2',6,6'-tetrahydroxy-1,1'-binaphthyls | |
| JPH01165581A (en) | Production of tetrabasic acid anhydride | |
| EP0853077A1 (en) | Process for producing alkyl 3-amino-4-substituted benzoates |