CA1092099A - Colorants azoiques - Google Patents

Colorants azoiques

Info

Publication number: CA1092099A
Authority: CA; Canada
Prior art keywords: compound; bis; solution; naphthalenediol; mole
Prior art date: 1976-06-01
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

CA277,992A

Other languages

English (en)

Inventor

Louis J. Rossi

John A. Ford, Jr.

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.)

Eastman Kodak Co

Original Assignee

Eastman Kodak Co

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.)

1976-06-01

Filing date

1977-05-09

Publication date

1980-12-23

1977-05-09 Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co

1980-12-23 Application granted granted Critical

1980-12-23 Publication of CA1092099A publication Critical patent/CA1092099A/fr

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 30
239000000987 azo dye Substances 0.000 title description 6
150000001768 cations Chemical class 0.000 claims abstract description 9
229910006074 SO2NH2 Inorganic materials 0.000 claims abstract description 3
150000003254 radicals Chemical class 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
GHLMAFCUHISLTJ-UHFFFAOYSA-N C1=CC(OCC(=O)N)=CC=C1N=NC(C1=CC=CC=C11)=C(O)C(O)=C1N=NC1=CC=C(OCC(N)=O)C=C1 Chemical compound C1=CC(OCC(=O)N)=CC=C1N=NC(C1=CC=CC=C11)=C(O)C(O)=C1N=NC1=CC=C(OCC(N)=O)C=C1 GHLMAFCUHISLTJ-UHFFFAOYSA-N 0.000 claims description 2
PRJQPTUZDNSBAN-UHFFFAOYSA-N C1=CC(OCC)=CC=C1N=NC(C1=CC=CC=C11)=C(O)C(O)=C1N=NC1=CC=C(OCC)C=C1 Chemical compound C1=CC(OCC)=CC=C1N=NC(C1=CC=CC=C11)=C(O)C(O)=C1N=NC1=CC=C(OCC)C=C1 PRJQPTUZDNSBAN-UHFFFAOYSA-N 0.000 claims description 2
UHLGWJOVJPOZRZ-UHFFFAOYSA-N COC1=CC=CC=C1CN=NC(C1=CC=CC=C11)=C(O)C(O)=C1N=NCC1=CC=CC=C1OC Chemical compound COC1=CC=CC=C1CN=NC(C1=CC=CC=C11)=C(O)C(O)=C1N=NCC1=CC=CC=C1OC UHLGWJOVJPOZRZ-UHFFFAOYSA-N 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims 2
239000001257 hydrogen Substances 0.000 claims 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
JXDVXHLBUGSPAP-UHFFFAOYSA-N 1,4-bis[[4-[ethyl(2-hydroxyethyl)amino]phenyl]hydrazinylidene]naphthalene-2,3-dione Chemical compound C1=CC(N(CCO)CC)=CC=C1NN=C(C=1C2=CC=CC=1)C(=O)C(=O)C2=NNC1=CC=C(N(CC)CCO)C=C1 JXDVXHLBUGSPAP-UHFFFAOYSA-N 0.000 claims 1
RBEKIRBJGKSCJK-UHFFFAOYSA-N C1=CC(OC)=CC=C1CN=NC(C1=CC=C(C=C11)S(N)(=O)=O)=C(O)C(O)=C1N=NCC1=CC=C(OC)C=C1 Chemical compound C1=CC(OC)=CC=C1CN=NC(C1=CC=C(C=C11)S(N)(=O)=O)=C(O)C(O)=C1N=NCC1=CC=C(OC)C=C1 RBEKIRBJGKSCJK-UHFFFAOYSA-N 0.000 claims 1
CBWBLOXMEYCYOI-UHFFFAOYSA-N C1=CC(OC)=CC=C1CN=NC(C1=CC=CC=C11)=C(O)C(O)=C1N=NCC1=CC=C(OC)C=C1 Chemical compound C1=CC(OC)=CC=C1CN=NC(C1=CC=CC=C11)=C(O)C(O)=C1N=NCC1=CC=C(OC)C=C1 CBWBLOXMEYCYOI-UHFFFAOYSA-N 0.000 claims 1
KVXCIWSKGAWYLC-UHFFFAOYSA-N C1=CC(OCCC)=CC=C1N=NC(C1=CC=CC=C11)=C(O)C(O)=C1N=NC1=CC=C(OCCC)C=C1 Chemical compound C1=CC(OCCC)=CC=C1N=NC(C1=CC=CC=C11)=C(O)C(O)=C1N=NC1=CC=C(OCCC)C=C1 KVXCIWSKGAWYLC-UHFFFAOYSA-N 0.000 claims 1
HSMCGQHOYCEPJG-UHFFFAOYSA-N COC1=CC=C([N+]([O-])=O)C=C1CN=NC(C1=CC=CC=C11)=C(O)C(O)=C1N=NCC1=CC([N+]([O-])=O)=CC=C1OC Chemical compound COC1=CC=C([N+]([O-])=O)C=C1CN=NC(C1=CC=CC=C11)=C(O)C(O)=C1N=NCC1=CC([N+]([O-])=O)=CC=C1OC HSMCGQHOYCEPJG-UHFFFAOYSA-N 0.000 claims 1
WXEAMSXSAKKVCH-UHFFFAOYSA-M [Na+].C(C1=CC=C(C=C1)OC)N=NC1=C(C(=C(C2=CC(=CC=C12)S(=O)(=O)[O-])N=NCC1=CC=C(C=C1)OC)O)O Chemical compound [Na+].C(C1=CC=C(C=C1)OC)N=NC1=C(C(=C(C2=CC(=CC=C12)S(=O)(=O)[O-])N=NCC1=CC=C(C=C1)OC)O)O WXEAMSXSAKKVCH-UHFFFAOYSA-M 0.000 claims 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
150000002431 hydrogen Chemical group 0.000 claims 1
239000000975 dye Substances 0.000 abstract description 30
229910052751 metal Inorganic materials 0.000 abstract description 7
239000002184 metal Substances 0.000 abstract description 7
229910052725 zinc Inorganic materials 0.000 abstract description 5
229910052793 cadmium Inorganic materials 0.000 abstract description 3
229910052718 tin Inorganic materials 0.000 abstract description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract description 2
125000000896 monocarboxylic acid group Chemical group 0.000 abstract description 2
239000000243 solution Substances 0.000 description 50
239000000203 mixture Substances 0.000 description 27
239000000049 pigment Substances 0.000 description 26
239000007788 liquid Substances 0.000 description 25
239000007787 solid Substances 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
-1 alkoxy radical Chemical class 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
235000019441 ethanol Nutrition 0.000 description 11
239000000463 material Substances 0.000 description 11
238000000034 method Methods 0.000 description 11
239000011230 binding agent Substances 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
239000012141 concentrate Substances 0.000 description 8
229960004756 ethanol Drugs 0.000 description 8
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
238000003756 stirring Methods 0.000 description 8
CNPVJWYWYZMPDS-UHFFFAOYSA-N 2-methyldecane Chemical compound CCCCCCCCC(C)C CNPVJWYWYZMPDS-UHFFFAOYSA-N 0.000 description 7
JRNGUTKWMSBIBF-UHFFFAOYSA-N naphthalene-2,3-diol Chemical compound C1=CC=C2C=C(O)C(O)=CC2=C1 JRNGUTKWMSBIBF-UHFFFAOYSA-N 0.000 description 7
230000008569 process Effects 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
239000012954 diazonium Substances 0.000 description 6
150000001989 diazonium salts Chemical class 0.000 description 6
230000007935 neutral effect Effects 0.000 description 6
239000002245 particle Substances 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
239000011734 sodium Substances 0.000 description 6
239000011701 zinc Substances 0.000 description 6
239000002253 acid Substances 0.000 description 5
229920000180 alkyd Polymers 0.000 description 5
238000009835 boiling Methods 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000003086 colorant Substances 0.000 description 5
239000006185 dispersion Substances 0.000 description 5
229920005989 resin Polymers 0.000 description 5
239000011347 resin Substances 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
238000000498 ball milling Methods 0.000 description 4
239000000047 product Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
150000003839 salts Chemical group 0.000 description 4
235000010288 sodium nitrite Nutrition 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
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000013078 crystal Substances 0.000 description 3
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
239000012260 resinous material Substances 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
YBUUDXMIIVBOIC-UHFFFAOYSA-N (3-acetyloxy-6-chlorosulfonylnaphthalen-2-yl) acetate Chemical compound C1=C(S(Cl)(=O)=O)C=C2C=C(OC(C)=O)C(OC(=O)C)=CC2=C1 YBUUDXMIIVBOIC-UHFFFAOYSA-N 0.000 description 2
FUPAJKKAHDLPAZ-UHFFFAOYSA-N 1,2,3-triphenylguanidine Chemical compound C=1C=CC=CC=1NC(=NC=1C=CC=CC=1)NC1=CC=CC=C1 FUPAJKKAHDLPAZ-UHFFFAOYSA-N 0.000 description 2
HBEICTUAWWEORS-UHFFFAOYSA-N 6,7-dihydroxynaphthalene-2-sulfonamide Chemical compound C1=C(O)C(O)=CC2=CC(S(=O)(=O)N)=CC=C21 HBEICTUAWWEORS-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
244000068988 Glycine max Species 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
CLRSZXHOSMKUIB-UHFFFAOYSA-M benzenediazonium chloride Chemical compound [Cl-].N#[N+]C1=CC=CC=C1 CLRSZXHOSMKUIB-UHFFFAOYSA-M 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000008878 coupling Effects 0.000 description 2
238000010168 coupling process Methods 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
238000007865 diluting Methods 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
230000001747 exhibiting effect Effects 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000000227 grinding Methods 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
229920001568 phenolic resin Polymers 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000000344 soap Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
230000003595 spectral effect Effects 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 1
KPAPHODVWOVUJL-UHFFFAOYSA-N 1-benzofuran;1h-indene Chemical compound C1=CC=C2CC=CC2=C1.C1=CC=C2OC=CC2=C1 KPAPHODVWOVUJL-UHFFFAOYSA-N 0.000 description 1
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical group C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
QRJZGVVKGFIGLI-UHFFFAOYSA-N 2-phenylguanidine Chemical compound NC(=N)NC1=CC=CC=C1 QRJZGVVKGFIGLI-UHFFFAOYSA-N 0.000 description 1
LFKVCVGVGODJQN-UHFFFAOYSA-M 4-[ethyl(2-hydroxyethyl)amino]benzenediazonium;chloride Chemical compound [Cl-].OCCN(CC)C1=CC=C([N+]#N)C=C1 LFKVCVGVGODJQN-UHFFFAOYSA-M 0.000 description 1
NKFIBMOQAPEKNZ-UHFFFAOYSA-N 5-amino-1h-indole-2-carboxylic acid Chemical compound NC1=CC=C2NC(C(O)=O)=CC2=C1 NKFIBMOQAPEKNZ-UHFFFAOYSA-N 0.000 description 1
ODPOAESBSUKMHD-UHFFFAOYSA-L 6,7-dihydrodipyrido[1,2-b:1',2'-e]pyrazine-5,8-diium;dibromide Chemical compound [Br-].[Br-].C1=CC=[N+]2CC[N+]3=CC=CC=C3C2=C1 ODPOAESBSUKMHD-UHFFFAOYSA-L 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
NRZVMOKAFOFUAV-UHFFFAOYSA-K CC(C)[Ti+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O Chemical compound CC(C)[Ti+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O NRZVMOKAFOFUAV-UHFFFAOYSA-K 0.000 description 1
239000004709 Chlorinated polyethylene Substances 0.000 description 1
241000518994 Conta Species 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
239000005630 Diquat Substances 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
240000006240 Linum usitatissimum Species 0.000 description 1
235000004431 Linum usitatissimum Nutrition 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
102100038803 Somatotropin Human genes 0.000 description 1
108050007673 Somatotropin Proteins 0.000 description 1
241000394605 Viola striata Species 0.000 description 1
POXOMYJKCQPECE-UHFFFAOYSA-M [Cl-].[Zn].C(C)N(CCO)C1=CC=C(C=C1)[N+]#N Chemical compound [Cl-].[Zn].C(C)N(CCO)C1=CC=C(C=C1)[N+]#N POXOMYJKCQPECE-UHFFFAOYSA-M 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
150000004996 alkyl benzenes Chemical class 0.000 description 1
SOGAXMICEFXMKE-UHFFFAOYSA-N alpha-Methyl-n-butyl acrylate Natural products CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
229940063655 aluminum stearate Drugs 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
159000000032 aromatic acids Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
239000001055 blue pigment Substances 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
239000012043 crude product Substances 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
235000004426 flaxseed Nutrition 0.000 description 1
235000010985 glycerol esters of wood rosin Nutrition 0.000 description 1
DXTIKTAIYCJTII-UHFFFAOYSA-N guanidine acetate Chemical compound CC([O-])=O.NC([NH3+])=N DXTIKTAIYCJTII-UHFFFAOYSA-N 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
KETWBQOXTBGBBN-UHFFFAOYSA-N hex-1-enylbenzene Chemical compound CCCCC=CC1=CC=CC=C1 KETWBQOXTBGBBN-UHFFFAOYSA-N 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
AMRRGZHLRCWPGV-UHFFFAOYSA-N lithium;2-(2-methylprop-2-enoyloxy)ethanesulfonic acid Chemical compound [Li].CC(=C)C(=O)OCCS(O)(=O)=O AMRRGZHLRCWPGV-UHFFFAOYSA-N 0.000 description 1
RLQOUIUVEQXDPW-UHFFFAOYSA-M lithium;2-methylprop-2-enoate Chemical compound [Li+].CC(=C)C([O-])=O RLQOUIUVEQXDPW-UHFFFAOYSA-M 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
OFUAIAKLWWIPTC-UHFFFAOYSA-L magnesium;naphthalene-2-carboxylate Chemical compound [Mg+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 OFUAIAKLWWIPTC-UHFFFAOYSA-L 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Substances 0.000 description 1
SGGOJYZMTYGPCH-UHFFFAOYSA-L manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 SGGOJYZMTYGPCH-UHFFFAOYSA-L 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
230000009965 odorless effect Effects 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
229940059574 pentaerithrityl Drugs 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
239000005011 phenolic resin Substances 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
102220231274 rs782159081 Human genes 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
OGZCXDDEDCFNEF-UHFFFAOYSA-M sodium;6,7-diacetyloxynaphthalene-2-sulfonate Chemical compound [Na+].C1=C(S([O-])(=O)=O)C=C2C=C(OC(C)=O)C(OC(=O)C)=CC2=C1 OGZCXDDEDCFNEF-UHFFFAOYSA-M 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
235000015096 spirit Nutrition 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229910052712 strontium Inorganic materials 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000011135 tin Substances 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
229940029284 trichlorofluoromethane Drugs 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
ODNJVAVDJKOYFK-GRVYQHKQSA-L zinc;(9z,12z)-octadeca-9,12-dienoate Chemical compound [Zn+2].CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O.CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O ODNJVAVDJKOYFK-GRVYQHKQSA-L 0.000 description 1
MXODCLTZTIFYDV-UHFFFAOYSA-L zinc;1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylate Chemical compound [Zn+2].C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C([O-])=O.C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C([O-])=O MXODCLTZTIFYDV-UHFFFAOYSA-L 0.000 description 1

Landscapes

Developing Agents For Electrophotography (AREA)

CA277,992A 1976-06-01 1977-05-09 Colorants azoiques Expired CA1092099A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US69166776A	1976-06-01	1976-06-01
US691,667		1976-06-01

Publications (1)

Publication Number	Publication Date
CA1092099A true CA1092099A (fr)	1980-12-23

Family

ID=24777469

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA277,992A Expired CA1092099A (fr)	1976-06-01	1977-05-09	Colorants azoiques

Country Status (1)

Country	Link
CA (1)	CA1092099A (fr)

1977
- 1977-05-09 CA CA277,992A patent/CA1092099A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-12-23	MKEX	Expiry

Publication	Publication Date	Title
US4293492A (en)	1981-10-06	Disazo compounds derived from 3,6-bis(styryl)-9-ethylcarbazole
US4145299A (en)	1979-03-20	Electrographic liquid developers containing azo dye marking particles derived from 2,3-naphthalenediol or derivatives thereof
EP0117522A2 (fr)	1984-09-05	Pigments azoiques ayant un noyau de silice, leur procédé de fabrication et leur utilisation dans un toner pour électrophotographie
US3994872A (en)	1976-11-30	Tertiary-alkylamine salts of metal complex dyestuffs
JP3055673B2 (ja)	2000-06-26	画像記録用着色組成物
US4301227A (en)	1981-11-17	Electrophotographic liquid developer
US3933664A (en)	1976-01-20	Organic photoconductive toner materials
US4322529A (en)	1982-03-30	Tertiary-alkylamine salts of azine dyestuffs
US4247459A (en)	1981-01-27	Azo dye derivatives of 2,3-naphthalenediols
CA1092099A (fr)	1980-12-23	Colorants azoiques
US3653936A (en)	1972-04-04	Pigment preparations
US4051052A (en)	1977-09-27	Liquid developer
KR910006738B1 (ko)	1991-09-02	마젠타계 칼라 토너 조성물
US3781208A (en)	1973-12-25	Liquid developers containing azo dyes
GB1571439A (en)	1980-07-16	Benzene-azo-naphthalene pigments and electrographic developers containing them
US3574182A (en)	1971-04-06	Calcium salt of 6-bromo-1-(1'-sulfo-2'-naphthylazo)-2-naphthol
US3218311A (en)	1965-11-16	Water-insoluble disazo dyes
US4426327A (en)	1984-01-17	3,6-Disazo-9-ethyl carbazole compounds
JP3122770B2 (ja)	2001-01-09	画像記録用着色組成物
US3770638A (en)	1973-11-06	Liquid developers containing metal salts of acid dyes
KR100592171B1 (ko)	2006-06-23	화상기록용 착색조성물 및 화상기록제
EP0150319B1 (fr)	1987-07-01	Matériau d'enregistrement photographique en couleurs comprenant un libérateur de colorants bleu-verts, image en couleur obtenue an moyen de ces colorants ainsi que les colorants en soi
JP2885329B2 (ja)	1999-04-19	画像記録用着色組成物及び熱転写画像記録材
EP0490253B1 (fr)	1996-03-06	Toner magenta, pour le développement d'images électrostatiques
JP2554280B2 (ja)	1996-11-13	有機金属錯塩化合物