DE955538C - Verfahren zur Herstellung von Gemischen aus Alkaliphthalcoyaninen und metallfreien Phthalocyaninen - Google Patents
Verfahren zur Herstellung von Gemischen aus Alkaliphthalcoyaninen und metallfreien PhthalocyaninenInfo
- Publication number
- DE955538C DE955538C DEC5347A DEC0005347A DE955538C DE 955538 C DE955538 C DE 955538C DE C5347 A DEC5347 A DE C5347A DE C0005347 A DEC0005347 A DE C0005347A DE 955538 C DE955538 C DE 955538C
- Authority
- DE
- Germany
- Prior art keywords
- metal
- weight
- parts
- alkali
- alcohol
- 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.)
- Expired
Links
- 239000000203 mixture Substances 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 7
- 239000003513 alkali Substances 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 19
- 150000001340 alkali metals Chemical class 0.000 claims description 19
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 claims description 14
- 229920006391 phthalonitrile polymer Polymers 0.000 claims description 14
- 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 claims description 11
- 229910052708 sodium Inorganic materials 0.000 claims description 11
- 239000011734 sodium Substances 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 9
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound 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 description 21
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 10
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical group CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical class ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- -1 isooctyl Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Chemical group CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- 229940067107 phenylethyl alcohol Drugs 0.000 description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
- GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical compound CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 description 1
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- BCAUITQWDYLYKA-UHFFFAOYSA-N N-methylmethanamine quinoline Chemical compound CNC.C1=CC=C2C(=C1)C=CC=N2 BCAUITQWDYLYKA-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 238000006621 Wurtz reaction Methods 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 229930007927 cymene Natural products 0.000 description 1
- 150000004816 dichlorobenzenes Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-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
- 230000008092 positive effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- HIFJOEJCXUJQBO-UHFFFAOYSA-N sodium;cyclohexanolate Chemical compound [Na+].[O-]C1CCCCC1 HIFJOEJCXUJQBO-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229940012831 stearyl alcohol Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- 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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/30—Metal-free phthalocyanines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH708039X | 1951-02-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE955538C true DE955538C (de) | 1957-01-03 |
Family
ID=4530530
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC5347A Expired DE955538C (de) | 1951-02-06 | 1952-02-03 | Verfahren zur Herstellung von Gemischen aus Alkaliphthalcoyaninen und metallfreien Phthalocyaninen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US2699441A (enrdf_load_stackoverflow) |
| BE (1) | BE509000A (enrdf_load_stackoverflow) |
| CH (1) | CH292413A (enrdf_load_stackoverflow) |
| DE (1) | DE955538C (enrdf_load_stackoverflow) |
| FR (1) | FR1050179A (enrdf_load_stackoverflow) |
| GB (1) | GB708039A (enrdf_load_stackoverflow) |
| NL (1) | NL80561C (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1218639B (de) * | 1960-10-14 | 1966-06-08 | Geigy Ag J R | Verfahren zur Herstellung von Gemischen aus Alkaliphthalocyaninen und metallfreiem Phthalocyanin |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH579131A5 (enrdf_load_stackoverflow) * | 1972-12-28 | 1976-08-31 | Ciba Geigy Ag |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE733089C (de) * | 1936-11-08 | 1943-03-18 | Ig Farbenindustrie Ag | Verfahren zur Herstellung von metallhaltigen Phthalocyaninen |
| DE747046C (de) * | 1932-11-16 | 1944-09-06 | Ici Ltd | Verfahren zur Herstellung von Farbstoffen |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2214454A (en) * | 1936-12-11 | 1940-09-10 | Ici Ltd | Manufacture of finely divided phthalocyanine pigments |
| US2485168A (en) * | 1948-04-01 | 1949-10-18 | Du Pont | Manufacture of metal-free phthalocyanine |
-
0
- BE BE509000D patent/BE509000A/xx unknown
- NL NL80561D patent/NL80561C/xx active
-
1951
- 1951-02-06 CH CH292413D patent/CH292413A/de unknown
-
1952
- 1952-02-03 DE DEC5347A patent/DE955538C/de not_active Expired
- 1952-02-04 FR FR1050179D patent/FR1050179A/fr not_active Expired
- 1952-02-04 US US269902A patent/US2699441A/en not_active Expired - Lifetime
- 1952-02-05 GB GB3068/52A patent/GB708039A/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE747046C (de) * | 1932-11-16 | 1944-09-06 | Ici Ltd | Verfahren zur Herstellung von Farbstoffen |
| DE733089C (de) * | 1936-11-08 | 1943-03-18 | Ig Farbenindustrie Ag | Verfahren zur Herstellung von metallhaltigen Phthalocyaninen |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1218639B (de) * | 1960-10-14 | 1966-06-08 | Geigy Ag J R | Verfahren zur Herstellung von Gemischen aus Alkaliphthalocyaninen und metallfreiem Phthalocyanin |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1050179A (fr) | 1954-01-05 |
| BE509000A (enrdf_load_stackoverflow) | |
| US2699441A (en) | 1955-01-11 |
| NL80561C (enrdf_load_stackoverflow) | |
| CH292413A (de) | 1953-08-15 |
| GB708039A (en) | 1954-04-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0496306A1 (de) | Verfahren zur Herstellung von 3-Amino-9,13b-dihydro-1H-dibenz-[c,f]imidazol[1,5-a]azepin-hydrochlorid | |
| DE955538C (de) | Verfahren zur Herstellung von Gemischen aus Alkaliphthalcoyaninen und metallfreien Phthalocyaninen | |
| DE2524748C3 (de) | Verfahren zur Herstellung von 1 ^-Diaminoanthrachinon^-dinitril | |
| DE929805C (de) | Verfahren zur Herstellung von Nickel- oder Kobalttetra-aza-porphinen bzw. ihren alkyl- und cycloalkylsubstituierten Derivaten | |
| DE933047C (de) | Verfahren zur Herstellung von Alkaliphthalocyaninen | |
| DE1135471B (de) | Verfahren zur Herstellung von 3-Chlorchinoxalinderivaten | |
| DE908288C (de) | Verfahren zur Herstellung von Tetra-aza-porphinfarbstoffen | |
| DE1644509A1 (de) | Verfahren zur Herstellung von 1-Amino-2-hydroxyalkoxy-4-hydroxyanthrachinonen | |
| DE2555736C2 (de) | Verfahren zur Herstellung von Halogennitrobenzolen | |
| DE2450883C3 (de) | Verfahren zur Herstellung von 1-substituierten Anthrachinonen | |
| DE855710C (de) | Verfahren zur Herstellung von neuen komplexen Kobaltverbindungen | |
| DE679985C (de) | Verfahren zur Herstellung von Schwefelfarbstoffen | |
| EP0356851B1 (de) | Verfahren zur Herstellung von Lösungen von 1:2-Chromkomplex-Azofarbstoffen | |
| DE890109C (de) | Verfahren zur Herstellung von Aminophthalocyaninen | |
| DE1218639B (de) | Verfahren zur Herstellung von Gemischen aus Alkaliphthalocyaninen und metallfreiem Phthalocyanin | |
| DE567755C (de) | Verfahren zur Darstellung von Anthrachinonderivaten | |
| DE1114964B (de) | Verfahren zur Herstellung von wasserloeslichen Farbstoffen | |
| DE2756409A1 (de) | Verfahren zur gleichzeitigen herstellung von 1,3-disubstituierten harnstoffen und 1,2-diolen | |
| EP0146007A1 (de) | Verfahren zur Herstellung von 5-Oxethylsulfonyl-2-amino-phenol(-ethern) | |
| DE748918C (de) | Verfahren zur Herstellung von stickstoffhaltigen Naphthalinderivaten | |
| DE512821C (de) | Verfahren zur Herstellung von 1, 1-Dianthrachinonyl-2, 2-diurethan, seinen Derivaten und gegebenenfalls Kondensationsprodukten | |
| DE551028C (de) | Verfahren zur Herstellung von reinem Anthracen | |
| DE205881C (enrdf_load_stackoverflow) | ||
| DE1213553B (de) | Verfahren zur Herstellung von wasserunloeslichen Azofarbstoffen | |
| DE595024C (de) | Verfahren zur Herstellung von Kondensationsprodukten des Fluoranthens |