JPS647108B2 - - Google Patents

Info

Publication number: JPS647108B2
Authority: JP; Japan
Prior art keywords: copper phthalocyanine; parts; type; phthalocyanine; point
Prior art date: 1981-03-13
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.): Expired

Application number

JP3527881A

Other languages

English (en)

Japanese (ja)

Other versions

JPS57149358A (en

Inventor

Masayoshi Takahashi

So Ishihara

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

DIC Corp

Original Assignee

Dainippon Ink and Chemicals Co Ltd

Priority date (The priority date 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 date listed.)

1981-03-13

Filing date

1981-03-13

Publication date

1989-02-07

1981-03-13 Application filed by Dainippon Ink and Chemicals Co Ltd filed Critical Dainippon Ink and Chemicals Co Ltd

1981-03-13 Priority to JP3527881A priority Critical patent/JPS57149358A/ja

1982-09-14 Publication of JPS57149358A publication Critical patent/JPS57149358A/ja

1989-02-07 Publication of JPS647108B2 publication Critical patent/JPS647108B2/ja

Status Granted legal-status Critical Current

Links

RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 claims description 56
239000000049 pigment Substances 0.000 claims description 23
239000013078 crystal Substances 0.000 claims description 22
239000003607 modifier Substances 0.000 claims description 15
239000002904 solvent Substances 0.000 claims description 12
IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical group 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 claims description 9
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 8
239000004202 carbamide Substances 0.000 claims description 8
150000002894 organic compounds Chemical class 0.000 claims description 8
238000003756 stirring Methods 0.000 claims description 7
150000004996 alkyl benzenes Chemical class 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
238000009835 boiling Methods 0.000 claims description 3
239000007809 chemical reaction catalyst Substances 0.000 claims description 3
239000005749 Copper compound Substances 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical group 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
150000001880 copper compounds Chemical class 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
230000002194 synthesizing effect Effects 0.000 claims description 2
238000000034 method Methods 0.000 description 25
238000006243 chemical reaction Methods 0.000 description 13
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 12
150000001875 compounds Chemical class 0.000 description 11
239000003973 paint Substances 0.000 description 11
238000002441 X-ray diffraction Methods 0.000 description 8
238000001228 spectrum Methods 0.000 description 8
238000004438 BET method Methods 0.000 description 7
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 7
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 7
239000011521 glass Substances 0.000 description 6
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 6
APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 5
235000018660 ammonium molybdate Nutrition 0.000 description 5
239000011609 ammonium molybdate Substances 0.000 description 5
229940010552 ammonium molybdate Drugs 0.000 description 5
239000000976 ink Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
238000004040 coloring Methods 0.000 description 4
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
150000004982 aromatic amines Chemical class 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
238000006482 condensation reaction Methods 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
230000001747 exhibiting effect Effects 0.000 description 3
239000000203 mixture Substances 0.000 description 3
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 3
239000002994 raw material Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000002966 varnish Substances 0.000 description 3
VGVZNHQJMQJYJO-UHFFFAOYSA-N 1-methyl-2,3-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC(C)=C1C(C)C VGVZNHQJMQJYJO-UHFFFAOYSA-N 0.000 description 2
CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 2
CUIFMTWQFFCFCH-UHFFFAOYSA-N 2-ethylhexylbenzene Chemical compound CCCCC(CC)CC1=CC=CC=C1 CUIFMTWQFFCFCH-UHFFFAOYSA-N 0.000 description 2
JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 2
239000005750 Copper hydroxide Substances 0.000 description 2
229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 description 2
229920000180 alkyd Polymers 0.000 description 2
239000011324 bead Substances 0.000 description 2
150000001879 copper Chemical class 0.000 description 2
229910001956 copper hydroxide Inorganic materials 0.000 description 2
229910000365 copper sulfate Inorganic materials 0.000 description 2
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
229960003280 cupric chloride Drugs 0.000 description 2
229940045803 cuprous chloride Drugs 0.000 description 2
239000012467 final product Substances 0.000 description 2
238000000227 grinding Methods 0.000 description 2
RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
230000008707 rearrangement Effects 0.000 description 2
230000001105 regulatory effect Effects 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
GVTLFGJNTIRUEG-ZHACJKMWSA-N (e)-n-(3-methoxyphenyl)-3-phenylprop-2-enamide Chemical compound COC1=CC=CC(NC(=O)\C=C\C=2C=CC=CC=2)=C1 GVTLFGJNTIRUEG-ZHACJKMWSA-N 0.000 description 1
GDEQPEBFOWYWSA-UHFFFAOYSA-N 1,2-dimethyl-3-propan-2-ylbenzene Chemical group CC(C)C1=CC=CC(C)=C1C GDEQPEBFOWYWSA-UHFFFAOYSA-N 0.000 description 1
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
DYSRXWYRUJCNFI-UHFFFAOYSA-N 2,4-dibromoaniline Chemical compound NC1=CC=C(Br)C=C1Br DYSRXWYRUJCNFI-UHFFFAOYSA-N 0.000 description 1
KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 description 1
DTNSDCJFTHMDAK-UHFFFAOYSA-N 2-cyanobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C#N DTNSDCJFTHMDAK-UHFFFAOYSA-N 0.000 description 1
PIUUDKDOAUICQP-UHFFFAOYSA-N 2-methylpentan-2-ylbenzene Chemical compound CCCC(C)(C)C1=CC=CC=C1 PIUUDKDOAUICQP-UHFFFAOYSA-N 0.000 description 1
RVNUUWJGSOHMRR-UHFFFAOYSA-N 3,5-dibromoaniline Chemical compound NC1=CC(Br)=CC(Br)=C1 RVNUUWJGSOHMRR-UHFFFAOYSA-N 0.000 description 1
UQRLKWGPEVNVHT-UHFFFAOYSA-N 3,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC(Cl)=C1 UQRLKWGPEVNVHT-UHFFFAOYSA-N 0.000 description 1
WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
239000005751 Copper oxide Substances 0.000 description 1
235000003363 Cornus mas Nutrition 0.000 description 1
240000006766 Cornus mas Species 0.000 description 1
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
239000001055 blue pigment Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910000431 copper oxide Inorganic materials 0.000 description 1
BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 1
229960004643 cupric oxide Drugs 0.000 description 1
KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 1
229940112669 cuprous oxide Drugs 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000010586 diagram Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
239000010842 industrial wastewater Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229910000476 molybdenum oxide Inorganic materials 0.000 description 1
PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
NAYYNDKKHOIIOD-UHFFFAOYSA-N phthalamide Chemical compound NC(=O)C1=CC=CC=C1C(N)=O NAYYNDKKHOIIOD-UHFFFAOYSA-N 0.000 description 1
230000019612 pigmentation Effects 0.000 description 1
230000008092 positive effect Effects 0.000 description 1
238000010298 pulverizing process Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
235000002639 sodium chloride Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
235000010215 titanium dioxide Nutrition 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Nitrogen Condensed Heterocyclic Rings (AREA)

JP3527881A 1981-03-13 1981-03-13 Production of epsilon type copper phthalocyanine Granted JPS57149358A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP3527881A JPS57149358A (en)	1981-03-13	1981-03-13	Production of epsilon type copper phthalocyanine

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP3527881A JPS57149358A (en)	1981-03-13	1981-03-13	Production of epsilon type copper phthalocyanine

Publications (2)

Publication Number	Publication Date
JPS57149358A JPS57149358A (en)	1982-09-14
JPS647108B2 true JPS647108B2 (zh)	1989-02-07

Family

ID=12437309

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP3527881A Granted JPS57149358A (en)	1981-03-13	1981-03-13	Production of epsilon type copper phthalocyanine

Country Status (1)

Country	Link
JP (1)	JPS57149358A (zh)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4785091A (en) *	1986-10-31	1988-11-15	Sumitomo Chemical Company, Limited	Process for producing copper phthalocyanine pigment
JPH0763416B2 (ja) *	1991-03-25	1995-07-12	タカラベルモント株式会社	洗髪装置におけるシャンプーボールの洗浄装置
JPH04128144U (ja) *	1991-05-09	1992-11-24	大阪機工株式会社	工作機械における切削油の噴射装置
US5393339A (en) *	1994-05-11	1995-02-28	Miles Inc.	Preparation of phthalocyanine pigments
JP2002121420A (ja) *	2000-08-07	2002-04-23	Dainippon Ink & Chem Inc	銅フタロシアニン顔料及びその製造方法
KR20020077947A (ko) *	2001-04-03	2002-10-18	삼협자원개발 주식회사	구리 프탈로시아닌 합성용 용매의 제조방법
JP2007100008A (ja) *	2005-10-07	2007-04-19	Toyo Ink Mfg Co Ltd	ε型フタロシアニン顔料の製造方法
JP5205715B2 (ja) *	2006-06-16	2013-06-05	東洋インキＳｃホールディングス株式会社	ε型銅フタロシアニン顔料、その製造方法およびそれを用いた着色組成物
ES2390187T3 (es)	2007-02-19	2012-11-07	Basf Se	Método para la producción de pigmento rojo 149
CN105482490B (zh) *	2015-12-07	2017-03-22	江苏双乐化工颜料有限公司	一种ε型酞菁蓝的制备方法和用途

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2742066A1 (de) *	1976-09-21	1978-03-23	Ciba Geigy Ag	Kupferphthalocyanin-pigmentzusammensetzungen und verfahren zu deren herstellung

1981
- 1981-03-13 JP JP3527881A patent/JPS57149358A/ja active Granted

Also Published As

Publication number	Publication date
JPS57149358A (en)	1982-09-14

Publication	Publication Date	Title
JPS647108B2 (zh)	1989-02-07
US5318623A (en)	1994-06-07	Process for producing metal phthalocyanine pigment
JPS646234B2 (zh)	1989-02-02
US4810297A (en)	1989-03-07	Process for producing dimethylaminomethyl copper phthalocyanine and/or its derivatives
JPH0730265B2 (ja)	1995-04-05	結晶型の変換方法
JPS63207858A (ja)	1988-08-29	銅フタロシアニン顔料の製造方法
JPS6248769A (ja)	1987-03-03	銅フタロシアニンの製造方法
JP2782809B2 (ja)	1998-08-06	オキシチタニウムフタロシアニンの製造方法
KR0153296B1 (ko)	1998-11-02	선명한 구리프탈로시아닌 안료의 제조방법
JPH0116272B2 (zh)	1989-03-23
JPH011766A (ja)	1989-01-06	銅フタロシアニン顔料の製造方法
JP2517292B2 (ja)	1996-07-24	銅フタロシアニン顔料の製造方法
JPS5949259B2 (ja)	1984-12-01	鮮明な銅フタロシアニン顔料の製造法
JP2782782B2 (ja)	1998-08-06	オキシチタニウムフタロシアニンの製造法
EP1036824A2 (en)	2000-09-20	Metal phthalocyanine derivative and its use
JPS6253022B2 (zh)	1987-11-09
JP2812027B2 (ja)	1998-10-15	銅フタロシアニン顔料の製造法
JPS5842219B2 (ja)	1983-09-17	鮮明な銅フタロシアニン顔料の製造法
JP3852035B2 (ja)	2006-11-29	ポリクロル銅フタロシアニン顔料組成物及びその製造方法
JPH0336065B2 (zh)	1991-05-30
US7745617B2 (en)	2010-06-29	Metallophthalocyanine mixed crystal and phthalocyanine pigment containing the same
JP2547002B2 (ja)	1996-10-23	銅フタロシアニン顔料の製造法
JP3496276B2 (ja)	2004-02-09	銅フタロシアニンの製造法
JPS63113076A (ja)	1988-05-18	銅フタロシアニン顔料の製造方法
JPS58183757A (ja)	1983-10-27	新規無金属フタロシアニン結晶多形およびその製造法