CA1082832A - Composes a base de perinone, leur preparation et leur emploi comme colorants - Google Patents

Composes a base de perinone, leur preparation et leur emploi comme colorants

Info

Publication number: CA1082832A
Authority: CA; Canada
Prior art keywords: formula; lower alkyl; conh; substituted; carbon atoms
Prior art date: 1974-10-03
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

CA236,904A

Other languages

English (en)

Other versions

CA236904S (en

Inventor

Theodor Papenfuhs

Helmut Troster

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.)

Hoechst AG

Original Assignee

Hoechst AG

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.)

1974-10-03

Filing date

1975-10-02

Publication date

1980-07-29

1975-10-02 Application filed by Hoechst AG filed Critical Hoechst AG

1980-07-29 Application granted granted Critical

1980-07-29 Publication of CA1082832A publication Critical patent/CA1082832A/fr

Status Expired legal-status Critical Current

Links

DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical class C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 title claims description 3
239000000975 dye Substances 0.000 title description 6
238000004519 manufacturing process Methods 0.000 title 1
-1 perinone compound Chemical class 0.000 claims abstract description 23
239000000049 pigment Substances 0.000 claims abstract description 21
125000000217 alkyl group Chemical group 0.000 claims abstract description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 15
238000000034 method Methods 0.000 claims abstract description 13
230000008569 process Effects 0.000 claims abstract description 13
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims abstract description 11
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
239000001257 hydrogen Substances 0.000 claims abstract description 10
125000002947 alkylene group Chemical group 0.000 claims abstract description 9
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims abstract description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract description 3
150000001454 anthracenes Chemical class 0.000 claims abstract description 3
239000004922 lacquer Substances 0.000 claims description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
229920005989 resin Polymers 0.000 claims description 9
239000011347 resin Substances 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
239000003973 paint Substances 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
238000004043 dyeing Methods 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
229920000620 organic polymer Polymers 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 claims description 3
125000005236 alkanoylamino group Chemical group 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
229920002678 cellulose Polymers 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
150000002825 nitriles Chemical class 0.000 claims description 3
125000006501 nitrophenyl group Chemical group 0.000 claims description 3
229920003023 plastic Polymers 0.000 claims description 3
239000004033 plastic Substances 0.000 claims description 3
229920000728 polyester Polymers 0.000 claims description 3
229920000098 polyolefin Polymers 0.000 claims description 3
239000000243 solution Substances 0.000 claims description 3
238000009987 spinning Methods 0.000 claims description 3
239000004952 Polyamide Substances 0.000 claims description 2
229920002125 Sokalan® Polymers 0.000 claims description 2
HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 claims description 2
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
229920003086 cellulose ether Polymers 0.000 claims description 2
239000004584 polyacrylic acid Substances 0.000 claims description 2
229920002647 polyamide Polymers 0.000 claims description 2
239000004417 polycarbonate Substances 0.000 claims description 2
229920000642 polymer Polymers 0.000 claims description 2
229920002635 polyurethane Polymers 0.000 claims description 2
239000004814 polyurethane Substances 0.000 claims description 2
229960005419 nitrogen Drugs 0.000 claims 2
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
125000001589 carboacyl group Chemical group 0.000 claims 1
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims 1
229920000515 polycarbonate Polymers 0.000 claims 1
238000004040 coloring Methods 0.000 abstract description 2
239000000126 substance Substances 0.000 abstract 2
150000001875 compounds Chemical class 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 8
LSDUXZYXFUHHQP-UHFFFAOYSA-N (3,6-dihydroxynaphthalene-1-carbonyl) 3,6-dihydroxynaphthalene-1-carboxylate Chemical compound OC1=CC=C2C(C(=O)OC(=O)C=3C4=CC=C(C=C4C=C(O)C=3)O)=CC(O)=CC2=C1 LSDUXZYXFUHHQP-UHFFFAOYSA-N 0.000 description 7
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
239000002253 acid Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000002904 solvent Substances 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
230000008901 benefit Effects 0.000 description 3
230000000740 bleeding effect Effects 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000000976 ink Substances 0.000 description 3
229910052742 iron Inorganic materials 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000001052 yellow pigment Substances 0.000 description 3
YFOOEYJGMMJJLS-UHFFFAOYSA-N 1,8-diaminonaphthalene Chemical compound C1=CC(N)=C2C(N)=CC=CC2=C1 YFOOEYJGMMJJLS-UHFFFAOYSA-N 0.000 description 2
JAHADAZIDZMHOP-UHFFFAOYSA-N 4-amino-3-nitrobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1[N+]([O-])=O JAHADAZIDZMHOP-UHFFFAOYSA-N 0.000 description 2
239000001856 Ethyl cellulose Substances 0.000 description 2
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
229920001249 ethyl cellulose Polymers 0.000 description 2
235000019325 ethyl cellulose Nutrition 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
238000000227 grinding Methods 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
238000002955 isolation Methods 0.000 description 2
229960004592 isopropanol Drugs 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
229920002239 polyacrylonitrile Polymers 0.000 description 2
239000004800 polyvinyl chloride Substances 0.000 description 2
229920000915 polyvinyl chloride Polymers 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
230000009467 reduction Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
HEMGYNNCNNODNX-UHFFFAOYSA-N 3,4-diaminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1N HEMGYNNCNNODNX-UHFFFAOYSA-N 0.000 description 1
FXZPUKNSGZAWOJ-UHFFFAOYSA-N 3,6-dihydroxynaphthalene-1-carboxylic acid Chemical compound OC1=CC=C2C(C(=O)O)=CC(O)=CC2=C1 FXZPUKNSGZAWOJ-UHFFFAOYSA-N 0.000 description 1
WLERLTJBHCKOEF-UHFFFAOYSA-N 3,6-disulfonaphthalene-1-carboxylic acid Chemical compound OS(=O)(=O)C1=CC=C2C(C(=O)O)=CC(S(O)(=O)=O)=CC2=C1 WLERLTJBHCKOEF-UHFFFAOYSA-N 0.000 description 1
BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
KSSJBGNOJJETTC-UHFFFAOYSA-N COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC Chemical compound COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC KSSJBGNOJJETTC-UHFFFAOYSA-N 0.000 description 1
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 1
229920000877 Melamine resin Polymers 0.000 description 1
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
101150050192 PIGM gene Proteins 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
125000004442 acylamino group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229920000180 alkyd Polymers 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229920003180 amino resin Polymers 0.000 description 1
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
150000004984 aromatic diamines Chemical class 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
ANUAIBBBDSEVKN-UHFFFAOYSA-N benzene-1,2,4,5-tetramine Chemical compound NC1=CC(N)=C(N)C=C1N ANUAIBBBDSEVKN-UHFFFAOYSA-N 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000005018 casein Substances 0.000 description 1
BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
235000021240 caseins Nutrition 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
229920001727 cellulose butyrate Polymers 0.000 description 1
OIQPTROHQCGFEF-UHFFFAOYSA-L chembl1371409 Chemical compound [Na+].[Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 OIQPTROHQCGFEF-UHFFFAOYSA-L 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000009826 distribution Methods 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000004898 kneading Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000013508 migration Methods 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
HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 description 1
239000000025 natural resin Substances 0.000 description 1
NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
239000011368 organic material Substances 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
150000003097 polyterpenes Chemical class 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000001054 red pigment Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
COEZWFYORILMOM-UHFFFAOYSA-N sodium 4-[(2,4-dihydroxyphenyl)diazenyl]benzenesulfonic acid Chemical compound [Na+].OC1=CC(O)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 COEZWFYORILMOM-UHFFFAOYSA-N 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
229940117958 vinyl acetate Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3437—Six-membered rings condensed with carbocyclic rings
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/32—1.3 azoles of the anthracene series
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/12—Perinones, i.e. naphthoylene-aryl-imidazoles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Paints Or Removers (AREA)
Indole Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Coloring (AREA)
Compositions Of Macromolecular Compounds (AREA)

CA236,904A 1974-10-03 1975-10-02 Composes a base de perinone, leur preparation et leur emploi comme colorants Expired CA1082832A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEP2447228.4		1974-10-03
DE19742447228 DE2447228A1 (de)	1974-10-03	1974-10-03	Perinon-verbindungen, verfahren zu deren herstellung und ihre verwendung als farbmittel

Publications (1)

Publication Number	Publication Date
CA1082832A true CA1082832A (fr)	1980-07-29

Family

ID=5927449

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA236,904A Expired CA1082832A (fr)	1974-10-03	1975-10-02	Composes a base de perinone, leur preparation et leur emploi comme colorants

Country Status (7)

Country	Link
JP (1)	JPS5163823A (fr)
BR (1)	BR7506450A (fr)
CA (1)	CA1082832A (fr)
DE (1)	DE2447228A1 (fr)
FR (1)	FR2286864A1 (fr)
GB (1)	GB1522683A (fr)
IT (1)	IT1043040B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH650523A5 (de) *	1979-10-25	1985-07-31	Sandoz Ag	Phthaloperinon-farbstoffe.
FR2620713B1 (fr) *	1987-09-23	1992-04-17	Sandoz Sa	Procede de teinture dans la masse des polyamides synthetiques
US7018430B2 (en) *	2001-07-26	2006-03-28	Ciba Specialty Chemicals Corporation	Method of mass-coloring synthetic materials

1974
- 1974-10-03 DE DE19742447228 patent/DE2447228A1/de not_active Withdrawn
1975
- 1975-10-01 IT IT2785675A patent/IT1043040B/it active
- 1975-10-02 JP JP11830975A patent/JPS5163823A/ja active Pending
- 1975-10-02 CA CA236,904A patent/CA1082832A/fr not_active Expired
- 1975-10-03 BR BR7506450A patent/BR7506450A/pt unknown
- 1975-10-03 GB GB4066575A patent/GB1522683A/en not_active Expired
- 1975-10-03 FR FR7530316A patent/FR2286864A1/fr active Granted

Also Published As

Publication number	Publication date
DE2447228A1 (de)	1976-04-22
FR2286864B1 (fr)	1980-08-14
JPS5163823A (ja)	1976-06-02
BR7506450A (pt)	1976-08-10
GB1522683A (en)	1978-08-23
IT1043040B (it)	1980-02-20
FR2286864A1 (fr)	1976-04-30

Legal Events

Date	Code	Title	Description
1997-07-29	MKEX	Expiry

Publication	Publication Date	Title
US3646033A (en)	1972-02-29	Derivatives of isoindoline
US3875200A (en)	1975-04-01	New bis-2-azomethine pigments, process for their manufacture and their use
US4044036A (en)	1977-08-23	Metal complexes of bis-azomethines from hydroxy-aldehydes and alkylene diamines
US4097450A (en)	1978-06-27	Perinone compounds as colorants for polyolefins
CA1082832A (fr)	1980-07-29	Composes a base de perinone, leur preparation et leur emploi comme colorants
US3022298A (en)	1962-02-20	Dioxazine dyestuffs
US4666526A (en)	1987-05-19	Azine pigments, processes for their preparation, and their use
USRE27575E (en)	1973-02-06	Water-insoluble benzimidazolone containing monoazo dyestuffs
US3819632A (en)	1974-06-25	Naphthoylene-benzimidazole and naphthaloperinone
JPS62220562A (ja)	1987-09-28	アゾ化合物のアミン塩の新規顔料、その製造方法、及びその使用による高分子有機材料の着色方法
CA1083590A (fr)	1980-08-12	Preparation et emploi comme colorants de composes disazoiques de methine, insolubles dans l'eau
EP0934363B1 (fr)	2001-12-05	Procede destine a colorer une matiere organique de poids moleculaire eleve et pigments polycycliques
US4564680A (en)	1986-01-14	Isoindolazines
CA1061348A (fr)	1979-08-28	Complexe metallique a base d'iminoisoindolinone
US3939194A (en)	1976-02-17	Bis-2-azomethine pigments, process for their manufacture and their use
US3892750A (en)	1975-07-01	New azomethine pigments and processes for their manufacture
US3923793A (en)	1975-12-02	Hydroxynaphtholdehide monoazomethine amine dyestuffs
US5527922A (en)	1996-06-18	Pyrrolo[3,4-c]pyrroles containing cyanimino groups
US3242179A (en)	1966-03-22	Perimidone-g,y-dicareoxylic imides, their production and use as pigment dyes
US3842084A (en)	1974-10-15	Bis-(dimethyl-meta-sulfonamidophenyl)-imides of perylenes
DE2451049A1 (de)	1976-04-29	Perinon-verbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbmittel
US3923774A (en)	1975-12-02	Quinazolone containing phenyl-azo-pyridine compounds
CA1052803A (fr)	1979-04-17	Composes de methine diazoique insolubles dans l'eau
CA1089869A (fr)	1980-11-18	Obtention et emploi comme colorants de composes a base de diazomethine contenant des metaux
CA1064481A (fr)	1979-10-16	Pigments disazo, procede pour leur fabrication et leur utilisation