JPS63152668A - Production of trisazo pigment - Google Patents
Production of trisazo pigmentInfo
- Publication number
- JPS63152668A JPS63152668A JP29327887A JP29327887A JPS63152668A JP S63152668 A JPS63152668 A JP S63152668A JP 29327887 A JP29327887 A JP 29327887A JP 29327887 A JP29327887 A JP 29327887A JP S63152668 A JPS63152668 A JP S63152668A
- Authority
- JP
- Japan
- Prior art keywords
- ring
- substituted product
- group
- therefrom
- substituents
- 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
- 239000000049 pigment Substances 0.000 title claims abstract description 19
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 238000005859 coupling reaction Methods 0.000 claims abstract description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 125000001424 substituent group Chemical group 0.000 claims abstract description 11
- 150000001412 amines Chemical class 0.000 claims abstract description 9
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims abstract description 6
- 125000001041 indolyl group Chemical group 0.000 claims abstract description 6
- 230000008878 coupling Effects 0.000 claims abstract description 5
- 238000010168 coupling process Methods 0.000 claims abstract description 5
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000002148 esters Chemical class 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 3
- 239000002904 solvent Substances 0.000 abstract description 11
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- -1 ethylamine) Chemical class 0.000 abstract description 3
- 125000000129 anionic group Chemical group 0.000 abstract description 2
- 125000000524 functional group Chemical group 0.000 abstract description 2
- 239000007822 coupling agent Substances 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- 238000011403 purification operation Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 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
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- OYWRDHBGMCXGFY-UHFFFAOYSA-N 1,2,3-triazinane Chemical compound C1CNNNC1 OYWRDHBGMCXGFY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IVMKBBDVVDYGPS-UHFFFAOYSA-N 1,4-dipropylpiperazine Chemical compound CCCN1CCN(CCC)CC1 IVMKBBDVVDYGPS-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- NZVZVGPYTICZBZ-UHFFFAOYSA-N 1-benzylpiperidine Chemical compound C=1C=CC=CC=1CN1CCCCC1 NZVZVGPYTICZBZ-UHFFFAOYSA-N 0.000 description 1
- WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 description 1
- LQWJONARYDIOSE-UHFFFAOYSA-N 1-pentylpiperidine Chemical compound CCCCCN1CCCCC1 LQWJONARYDIOSE-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 description 1
- GHKSKVKCKMGRDU-UHFFFAOYSA-N 2-(3-aminopropylamino)ethanol Chemical compound NCCCNCCO GHKSKVKCKMGRDU-UHFFFAOYSA-N 0.000 description 1
- RILLZYSZSDGYGV-UHFFFAOYSA-N 2-(propan-2-ylamino)ethanol Chemical compound CC(C)NCCO RILLZYSZSDGYGV-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- VHYUNSUGCNKWSO-UHFFFAOYSA-N 3-propan-2-yloxypropan-1-amine Chemical compound CC(C)OCCCN VHYUNSUGCNKWSO-UHFFFAOYSA-N 0.000 description 1
- GVWBJJLCTWNTRU-UHFFFAOYSA-N 4-benzylmorpholine Chemical compound C=1C=CC=CC=1CN1CCOCC1 GVWBJJLCTWNTRU-UHFFFAOYSA-N 0.000 description 1
- LMRKVKPRHROQRR-UHFFFAOYSA-N 4-butylmorpholine Chemical compound CCCCN1CCOCC1 LMRKVKPRHROQRR-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 229940043276 diisopropanolamine Drugs 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- PMHXGHYANBXRSZ-UHFFFAOYSA-N n,n-dimethyl-2-morpholin-4-ylethanamine Chemical compound CN(C)CCN1CCOCC1 PMHXGHYANBXRSZ-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003334 secondary amides Chemical class 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Indole Compounds (AREA)
Abstract
Description
【発明の詳細な説明】 本発明はトリスアゾ顔料の製造法に関する。[Detailed description of the invention] The present invention relates to a method for producing trisazo pigments.
従来のトリスアゾ顔料の製造法は一般にヘキサゾニウム
塩とカップリング化合物とを酢酸すトリウム水溶液など
の無機アルカリ性化合物の水溶液の存在下でカップリン
グ反応させた後。The conventional method for producing trisazo pigments generally involves a coupling reaction between a hexazonium salt and a coupling compound in the presence of an aqueous solution of an inorganic alkaline compound such as an aqueous solution of sodium acetate.
目的物を析出させるというものである。しかしこのよう
な方法では無機アルカリ性水溶液を用いるため、カップ
リング反応に用いる溶媒（例えばＮ、Ｎ−ジメチルホル
ムアミド、ジメチルスルホキシド等）の溶解力が低下し
、目的のトリスアゾ顔料と同時に不純物（副反応物）が
反応系から析出する結果、その後の精製操作（例えば溶
媒による洗浄或いは再結晶）が不可欠であった。また同
様な理由からカップリング反応に用いられる溶媒は前述
のようなＮ、Ｎ−ジメチルホルムアミド等の水と相溶性
を有するものに限られ、従って回収、再使用することは
きわめて困廻であった。更に従来の方法はカップリング
反応に長時間を要した。The purpose is to precipitate the target substance. However, since this method uses an inorganic alkaline aqueous solution, the solubility of the solvent used in the coupling reaction (e.g. N,N-dimethylformamide, dimethyl sulfoxide, etc.) decreases, and impurities (side reactants) are removed at the same time as the target trisazo pigment. ) precipitates from the reaction system, and as a result, subsequent purification operations (for example, washing with a solvent or recrystallization) are essential. Furthermore, for the same reason, the solvents used in the coupling reaction are limited to those that are compatible with water, such as the aforementioned N,N-dimethylformamide, and therefore it is extremely difficult to recover and reuse them. . Furthermore, the conventional method required a long time for the coupling reaction.
以上の欠点を改良するため、本発明者らは種々の検討を
行なった結果、アルカリ剤として有機アミンを用いてカ
ップリング反応を行なう事により、高純度のトリスアゾ
顔料を効率よく得られることを見出し、本発明を完成し
た。In order to improve the above drawbacks, the present inventors conducted various studies and found that a highly pure trisazo pigment can be efficiently obtained by carrying out a coupling reaction using an organic amine as an alkaline agent. , completed the invention.
即ち本発明の目的は精製操作を行なわずに高純度のトリ
スアゾ化合物を製造することである。That is, an object of the present invention is to produce a highly pure trisazo compound without performing any purification operation.
また本発明の目的は精製操作が不要のため、コストの低
いトリスアゾ顔料を製造することである。更に本発明の
目的は有機アミンを用いることにより広範囲に溶媒の選
択が可能となり、従って必要により溶媒の回収、再使用
が非常に容易になるトリスアゾ顔料を製造することであ
る。Another object of the present invention is to produce a trisazo pigment at low cost since no purification operation is required. A further object of the present invention is to produce trisazo pigments which, by using organic amines, allow a wide selection of solvents and therefore make it very easy to recover and reuse the solvents if necessary.
本発明のトリスアゾ顔料の製造法はへキサゾニウム塩と
一般式
％式％（２）
（ここで又はベンゼン環又はその置換体、ナフタレン環
又はその置換体、インドール環又はその置換体、カルバ
ゾール環又はその置換体、及びベンゾフラン環又はその
置換体よりなる群から選ばれたいずれか１種であり、Ａ
ｒｃはベンゼン環又はその置換体、ナフタレン環又はそ
の置換体、インドール環又はその置換体、カルバゾール
環又はその置換体、及びジベンゾフラン環又はその置換
体よりなる群から選ばれたいずれか１種であり、Ａｒ、
及びＡｒ、は各々ベンゼン環又はその置換体、及びナフ
タレン環又はその置換体よりなる群から選ばれたいずれ
か１種であり、Ｒ工及びＲ３ハ各々水素、低級アルキル
基、及びフェニル基又はその置換体よりなる群から選ば
れたいずれか１種であり、またＲ２は低級アルキル基、
及びカルボキシル基又はそのエステルよりなる群から選
ばれたいずれか１種である。）で示されるカップリング
化合物とを有機アミンの存在下で反応させることを特徴
とするものである。The method for producing the trisazo pigment of the present invention is to use a hexazonium salt and the general formula % (2) (here or a benzene ring or a substituted product thereof, a naphthalene ring or a substituted product thereof, an indole ring or a substituted product thereof, a carbazole ring or a substituted product thereof). Any one selected from the group consisting of a substituted product, a benzofuran ring, or a substituted product thereof, and A
rc is any one selected from the group consisting of a benzene ring or a substituted product thereof, a naphthalene ring or a substituted product thereof, an indole ring or a substituted product thereof, a carbazole ring or a substituted product thereof, and a dibenzofuran ring or a substituted product thereof; ,Ar,
and Ar are each one selected from the group consisting of a benzene ring or a substituent thereof, and a naphthalene ring or a substituent thereof, and R and R each represent hydrogen, a lower alkyl group, a phenyl group, or Any one selected from the group consisting of substituents, and R2 is a lower alkyl group,
and a carboxyl group or an ester thereof. ) in the presence of an organic amine.
本発明を更に詳しく説明すると、トリアミノ化合物を通
常の如く、塩酸中、亜硝酸ナトリウムの水溶液でジアゾ
化し、更にそれを例えばフッ化ホウ素酸塩として分離す
る。このようにして得られたヘキサゾニウム塩と前記一
般式（１）、（２）又は（３）のカンプリング化合物と
を適当な溶媒に溶解した後、これに−１０″〜３０℃の
温度で有機アミンを滴下することにより行なわれる。To further explain the invention, the triamino compound is conventionally diazotized with an aqueous solution of sodium nitrite in hydrochloric acid and then isolated as, for example, the fluoroborate salt. After dissolving the hexazonium salt thus obtained and the camping compound of the general formula (1), (2) or (3) in a suitable solvent, an organic This is done by adding the amine dropwise.
このカップリング反応は５分から３時間で完結する。This coupling reaction is completed in 5 minutes to 3 hours.
またこのカップリング反応はカップリング成分と有機ア
ミンとを適当な溶媒に溶解した後、前記温度でヘキサゾ
ニウム塩の溶液を滴下しても同様に行なうことができる
。The coupling reaction can also be similarly carried out by dissolving the coupling component and the organic amine in a suitable solvent and then adding a solution of the hexazonium salt dropwise at the above temperature.
このようにして得られるトリスアゾ顔料は精製操作を行
なわなくても純度の高いものであり、充分実用に供する
ことができる。The trisazo pigment thus obtained has a high purity even without any purification operation, and can be fully used for practical purposes.
本発明で用いられる溶媒としてはＮ、Ｎ−ジメチルホル
ムアミド、ジメチルスルホキシド。Solvents used in the present invention include N,N-dimethylformamide and dimethylsulfoxide.
テトラヒドロフラン、ジオキサン、アセトニトリル、二
硫化炭素、アセトン、メチルエチルケトン、ベンゼン、
トルエン、キシレン、クロルベンゼン、ニトロベンゼン
、ベンジルアルコール、アニソール、ジフェニルエーテ
ル、四塩化炭素、クロロホルム、ジクロルエタン、メタ
ノール、エタノール、エチレングリコール、ブタノール
、メチルセロソルブ、エチルセロソルブ、プルピルエー
テル等の通常の溶媒が挙げられる。Tetrahydrofuran, dioxane, acetonitrile, carbon disulfide, acetone, methyl ethyl ketone, benzene,
Common solvents include toluene, xylene, chlorobenzene, nitrobenzene, benzyl alcohol, anisole, diphenyl ether, carbon tetrachloride, chloroform, dichloroethane, methanol, ethanol, ethylene glycol, butanol, methyl cellosolve, ethyl cellosolve, propyl ether, etc. .
また有機アミンとしてはエチルアミン、プロピルアミン
、ブチルアミン、ジメチルアミン、ジエチルアミン、ジ
ブチルアミン、トリエチルアミン、トリブチルアミン、
シクロヘキシルアミン、エチレンジアミン、１，２−ジ
アミノプロパン、１，３−ジアミノプロパン、とドロキ
シエチルアミノエチルアミン、ヒドロキシエチルアミノ
プロピルアミン、３−７ミノプロパノール、インプロパ
ツールアミン、Ｎ−メチルエタノールアミン、２−アミ
ノ−２−エチル−１゜３−プロパンジオール、ジイソプ
ロパツールアミン、トリイソプロパツールアミン、ジェ
タノールアミン、トリエタノールアミン、Ｎ−メチルジ
ェタノールアミン、Ｎ−エチルジェタノールアミン、Ｎ
−ブチルジェタノールアミン、ジグリコールアミン、２
−（イソプロピルアミノ）エタノール、３−イソプロポ
キシプロビルアミン、モルホリン、Ｎ−メチルモルホリ
ン、Ｎ−ブチルモルホリン、Ｎ−ベンジルモルホリン。Examples of organic amines include ethylamine, propylamine, butylamine, dimethylamine, diethylamine, dibutylamine, triethylamine, tributylamine,
Cyclohexylamine, ethylenediamine, 1,2-diaminopropane, 1,3-diaminopropane, and droxyethylaminoethylamine, hydroxyethylaminopropylamine, 3-7minopropanol, impropaturamine, N-methylethanolamine, 2 -Amino-2-ethyl-1゜3-propanediol, diisopropanolamine, triisopropanolamine, jetanolamine, triethanolamine, N-methyljetanolamine, N-ethyljetanolamine, N
-butyljethanolamine, diglycolamine, 2
-(isopropylamino)ethanol, 3-isopropoxypropylamine, morpholine, N-methylmorpholine, N-butylmorpholine, N-benzylmorpholine.
ジメチルアミノエチルモルホリン、ピペリジン、Ｎ−エ
チルピペリジン、Ｎ−アミルピペリジン、Ｎ−ベンジル
ピペリジン、ピペラジン、Ｎ−メチルピペラジン、Ｎ、
Ｎ’−ジメチルピペラジン、Ｎ−エチルピペラジン、
Ｎ、 Ｎ’−ジプロピルピペラジン、Ｎ−（２−アミノ
エチル）ピペラジン、ｌ、２．４−トリメチルピペラジ
ン、Ｎ、Ｎ’−ジェタノールピペラジン、ヘキサヒドロ
トリアジン、Ｎ、Ｎ’、Ｎ’−トリメチルへキサヒドロ
トリアジン、トリエチレンテトラミン、１，７−ジアミ
ツー４−アザヘプタン、１゜４−ジアザ−ビシクロ［２
，２，２］オクタン。Dimethylaminoethylmorpholine, piperidine, N-ethylpiperidine, N-amylpiperidine, N-benzylpiperidine, piperazine, N-methylpiperazine, N,
N'-dimethylpiperazine, N-ethylpiperazine,
N,N'-dipropylpiperazine, N-(2-aminoethyl)piperazine, l,2,4-trimethylpiperazine, N,N'-getanolpiperazine, hexahydrotriazine, N,N',N'-trimethyl Hexahydrotriazine, triethylenetetramine, 1,7-diamitu-4-azaheptane, 1゜4-diaza-bicyclo[2
,2,2]octane.
１．８−ジアザービシプロ（５，４，０３ウンデセン−
７などが挙げられる。1.8-Diazabicipro(5,4,03 undecene-
7 etc.
またへキサゾニウム塩は目的とするトリスアゾ顔料によ
って選択されるが、次のような化合物が例示される。Further, the hexazonium salt is selected depending on the intended trisazo pigment, and the following compounds are exemplified.
Ｎ−（−＠−Ｎ、”）、・３ｒ
ここでＸはアニオン官能基を示す、 ＼本発明方法に
よって得られるトリスアゾ顔料は米国特許第３，８９８
．０１３４号、同第４，０５２，２１０号明細書、及び
特開昭４８−７０５３８号公報で提案されるような電子
写真感光体に有利に応用される。N-(-@-N,"), 3r where X represents an anionic functional group, the trisazo pigment obtained by the method of the present invention is described in U.S. Pat. No. 3,898
．． It is advantageously applied to electrophotographic photoreceptors such as those proposed in Japanese Patent Application Laid-Open No. 48-70538, Japanese Patent Application Laid-Open No. 48-70538.
このような目的化合物を例示すれば次の通りである。Examples of such target compounds are as follows.
以下に実施例を示す。Examples are shown below.
実施例１（トリスアゾ顔料化合物Ｎ１１１の製造）４．
４’、４’−トリアミノフェニルアミン８゜７ｇを濃塩
酸１５０ｍＱ及び水１３０ｍＡから＋ＥＩ１１製した希
塩酸に加え、室温で約３０分間よく攪拌する。Example 1 (Production of trisazo pigment compound N111)4.
8.7 g of 4',4'-triaminophenylamine is added to dilute hydrochloric acid prepared from +EI11 from 150 mQ of concentrated hydrochloric acid and 130 mA of water, and stirred well at room temperature for about 30 minutes.
次に得られた混合物を約ｏ℃に冷却し、亜硝酸ナトリウ
ム７．７ｇを水３０ｍＱに溶解した溶液を、＝３〜２℃
の温度で約２０分間に亘って滴下する。The resulting mixture was then cooled to about 0°C, and a solution of 7.7 g of sodium nitrite dissolved in 30 mQ of water was added to the mixture at 3-2°C.
The mixture was added dropwise over a period of about 20 minutes at a temperature of .
その後、同温度で約１時間攪拌し、微量の未反応物を濾
別し、濾液に４２％硼弗化水素酸水溶液６０ｍ１２を加
え、析出する沈澱を濾取し水洗した後、乾燥して１５．
３ ｇのへキサゾニウム塩を得た。Thereafter, the mixture was stirred at the same temperature for about 1 hour, a trace amount of unreacted material was filtered off, 60 mL of 42% borohydrofluoric acid aqueous solution was added to the filtrate, and the precipitate was collected by filtration, washed with water, and dried for 15 minutes. ．．
3 g of hexazonium salt was obtained.
次にカップリング成分として２−ヒドロキシ−３−デフ
１−工酸アニリド８．７ ｇ （０，０３３ｍｏｌ）、
有機アミンとしてトリエタノールアミン８．１ ｇ（０
，０６＋＋＋ｏｌ）を、Ｎ、Ｎ−ジメチルホルムアミド
９００ｍ１ｌに溶解した。この溶液を５℃に冷却し、先
のへキサゾニウム塩５．９ ｇ （０，０１ｍｏｌ）を
Ｎ。Next, 8.7 g (0,033 mol) of 2-hydroxy-3-def-1-technic acid anilide as a coupling component,
Triethanolamine 8.1 g (0
,06+++ol) was dissolved in 900ml of N,N-dimethylformamide. This solution was cooled to 5°C, and 5.9 g (0.01 mol) of the above hexazonium salt was added with N.
Ｎ−ジメチルホルムアミド５０ｒｒｌに溶解した溶液を
５〜ｌＯ℃の温度で約３０分間に亘って滴下した後、室
温で更に４時間攪拌した。その後、生成した沈澱を濾取
し、１００℃、２ｍｍ）Ｉｇの減圧下に乾燥して化合物
＆１のトリスアゾ顔料８．５ｇ（収率７５％）を得た。A solution dissolved in 50 rrl of N-dimethylformamide was added dropwise at a temperature of 5 to 10° C. over about 30 minutes, and the mixture was further stirred at room temperature for 4 hours. Thereafter, the generated precipitate was collected by filtration and dried at 100° C. under a reduced pressure of 2 mm) Ig to obtain 8.5 g (yield: 75%) of the trisazo pigment of compound &1.
赤外線スペクトル（ＫＢｒ錠剤法）
１６８０ （！１−’（第２アミドの吸収）元素分析（
Ｃ，。ｌ（、、Ｎ工。０６として）計算値 実測値
Ｃ（％） ７４．４５ ７４．６１Ｈ（％）
４，３５ ４．０８Ｎ（％） １
２．５８ １２．４０比較例
トリエタノールアミンの代りに酢酸ナトリウム３．３ｇ
を水８０＋ａ１２に溶解したアルカリ水溶液を用いた他
は実施例１と同じ方法でトリスアゾ顔料を製造した。Infrared spectrum (KBr tablet method) 1680 (!1-' (secondary amide absorption) elemental analysis (
C. l (,, N engineering.06) Calculated value Actual value C (%) 74.45 74.61H (%)
4,35 4.08N (%) 1
2.58 12.40 Comparative Example 3.3 g of sodium acetate instead of triethanolamine
A trisazo pigment was produced in the same manner as in Example 1, except that an aqueous alkaline solution prepared by dissolving 80+a12 of water was used.
元素分析
計算値 実測値
Ｃ（％） ７４．４５ ７２．４９Ｈ（％）
４，３５ ３゜９９Ｎ（％） １
２．５８ １１゜３４この結果から本発明方法によ
れば比較例の方法よりも高純度のトリスアゾ顔料が得ら
れ、従って精製操作を必要としないことが判る。Elemental analysis calculated value Actual value C (%) 74.45 72.49H (%)
4,35 3°99N (%) 1
2.58 11°34 From these results, it can be seen that according to the method of the present invention, a trisazo pigment of higher purity than the method of the comparative example can be obtained, and therefore no purification operation is required.
実施例２〜９
表−１に示す素材及び条件を用いた他は実施例１と同じ
方法で同表に示す目的化合物を製造した。得られたトリ
スアゾ顔料はいずれも高純度で、精製操作を必要としな
いものであった。Examples 2 to 9 The target compounds shown in Table 1 were produced in the same manner as in Example 1, except that the materials and conditions shown in Table 1 were used. The obtained trisazo pigments were all highly pure and did not require any purification operation.
Claims (1)
、化学式、表等があります▼ 又は（３） ▲数式、化学式、表等があります▼ （ここでＸはベンゼン環又はその置換体、ナフタレン環
又はその置換体、インドール環又はその置換体、カルバ
ゾール環又はその置換体、及びベンゾフラン環又はその
置換体よりなる群から選ばれたいずれか１種であり、Ａ
ｒ＿１はベンゼン環又はその置換体、ナフタレン環又は
その置換体、インドール環又はその置換体、カルバゾー
ル環又はその置換体、及びジベンゾフラン環又はその置
換体よりなる群から選ばれたいずれか１種であり、Ａｒ
＿２及びＡｒ＿３は各々ベンゼン環又はその置換体、及
びナフタレン環又はその置換体よりなる群から選ばれた
いずれか１種であり、Ｒ＿１及びＲ＿３は各々水素、低
級アルキル基、及びフェニル基又はその置換体よりなる
群から選ばれたいずれか１種であり、またＲ＿２は低級
アルキル基、及びカルボキシル基又はそのエステルより
なる群から選ばれたいずれか１種である。） で示されるカップリング化合物とを有機アミンの存在下
で反応させることを特徴とするトリスアゾ顔料の製造方
法。[Claims] 1. Hexazonium salt and general formula (1) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (2) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or (3) ▲ ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (Here, X is selected from the group consisting of a benzene ring or its substituents, a naphthalene ring or its substituents, an indole ring or its substituents, a carbazole ring or its substituents, and a benzofuran ring or its substituents. Any one type, A
r_1 is any one selected from the group consisting of a benzene ring or a substituted product thereof, a naphthalene ring or a substituted product thereof, an indole ring or a substituted product thereof, a carbazole ring or a substituted product thereof, and a dibenzofuran ring or a substituted product thereof; , Ar
_2 and Ar_3 are each one selected from the group consisting of a benzene ring or a substituted product thereof, and a naphthalene ring or a substituted product thereof, and R_1 and R_3 are each hydrogen, a lower alkyl group, a phenyl group, or a substituted product thereof. R_2 is any one selected from the group consisting of a lower alkyl group, a carboxyl group, or an ester thereof. ) A method for producing a trisazo pigment, which comprises reacting a coupling compound represented by the following formula in the presence of an organic amine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29327887A JPS63152668A (en) | 1987-11-20 | 1987-11-20 | Production of trisazo pigment |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29327887A JPS63152668A (en) | 1987-11-20 | 1987-11-20 | Production of trisazo pigment |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6478578A Division JPS54155227A (en) | 1978-05-30 | 1978-05-30 | Preparation of dis-or trisazo pigment |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63152668A true JPS63152668A (en) | 1988-06-25 |
Family
ID=17792758
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP29327887A Pending JPS63152668A (en) | 1987-11-20 | 1987-11-20 | Production of trisazo pigment |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63152668A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008517756A (en) * | 2004-10-29 | 2008-05-29 | オスムーズ | Nebulizer comprising means for pressurizing liquid to be sprayed |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4865228A (en) * | 1971-12-13 | 1973-09-08 | ||
| JPS4981439A (en) * | 1972-11-16 | 1974-08-06 | ||
| JPS5064318A (en) * | 1973-10-09 | 1975-05-31 | ||
| JPS5139728A (en) * | 1974-07-23 | 1976-04-02 | Ciba Geigy | JISUAZOGANRYONOSEIZOHOHO |
| JPS5160222A (en) * | 1974-09-26 | 1976-05-26 | Ciba Geigy | Jisuazoganryono seizohoho |
| JPS5182315A (en) * | 1974-12-06 | 1976-07-19 | Bayer Ag | HORIAZOSENRYONOSEIZOHO |
-
1987
- 1987-11-20 JP JP29327887A patent/JPS63152668A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4865228A (en) * | 1971-12-13 | 1973-09-08 | ||
| JPS4981439A (en) * | 1972-11-16 | 1974-08-06 | ||
| JPS5064318A (en) * | 1973-10-09 | 1975-05-31 | ||
| JPS5139728A (en) * | 1974-07-23 | 1976-04-02 | Ciba Geigy | JISUAZOGANRYONOSEIZOHOHO |
| JPS5160222A (en) * | 1974-09-26 | 1976-05-26 | Ciba Geigy | Jisuazoganryono seizohoho |
| JPS5182315A (en) * | 1974-12-06 | 1976-07-19 | Bayer Ag | HORIAZOSENRYONOSEIZOHO |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008517756A (en) * | 2004-10-29 | 2008-05-29 | オスムーズ | Nebulizer comprising means for pressurizing liquid to be sprayed |
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