GB806175A - Production of dyestuffs of the phthalocyanine series - Google Patents
Production of dyestuffs of the phthalocyanine seriesInfo
- Publication number
- GB806175A GB806175A GB20665/56A GB2066556A GB806175A GB 806175 A GB806175 A GB 806175A GB 20665/56 A GB20665/56 A GB 20665/56A GB 2066556 A GB2066556 A GB 2066556A GB 806175 A GB806175 A GB 806175A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phthalocyanine
- copper
- reacted
- ethyl
- quaternary ammonium
- 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
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class 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 title abstract 3
- -1 phthalocyanine radical Chemical class 0.000 abstract 5
- 238000006243 chemical reaction Methods 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- 229930040373 Paraformaldehyde Natural products 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000010949 copper Substances 0.000 abstract 2
- 229910052802 copper Inorganic materials 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 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 abstract 2
- 229920002866 paraformaldehyde Polymers 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 abstract 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 abstract 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical group NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 2
- CNLHIRFQKMVKPX-UHFFFAOYSA-N 1,1-diethylthiourea Chemical compound CCN(CC)C(N)=S CNLHIRFQKMVKPX-UHFFFAOYSA-N 0.000 abstract 1
- JUIKUQOUMZUFQT-UHFFFAOYSA-N 2-bromoacetamide Chemical compound NC(=O)CBr JUIKUQOUMZUFQT-UHFFFAOYSA-N 0.000 abstract 1
- FDWNCOLDJCZPNR-UHFFFAOYSA-N 2-chloro-n-(chloromethyl)acetamide Chemical compound ClCNC(=O)CCl FDWNCOLDJCZPNR-UHFFFAOYSA-N 0.000 abstract 1
- TXNSZCSYBXHETP-UHFFFAOYSA-N 2-chloro-n-(hydroxymethyl)acetamide Chemical compound OCNC(=O)CCl TXNSZCSYBXHETP-UHFFFAOYSA-N 0.000 abstract 1
- HOZLOOPIXHWKCI-UHFFFAOYSA-N 2-chloro-n-methylacetamide Chemical compound CNC(=O)CCl HOZLOOPIXHWKCI-UHFFFAOYSA-N 0.000 abstract 1
- LIFLLGAGRGBWPO-UHFFFAOYSA-N CC[S+]=C(C)N Chemical compound CC[S+]=C(C)N LIFLLGAGRGBWPO-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- SGMOYEJCXITCTH-UHFFFAOYSA-N N,N-bis(ethylamino)acetamide Chemical compound C(C)NN(C(C)=O)NCC SGMOYEJCXITCTH-UHFFFAOYSA-N 0.000 abstract 1
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 abstract 1
- KQJQICVXLJTWQD-UHFFFAOYSA-N N-Methylthiourea Chemical group CNC(N)=S KQJQICVXLJTWQD-UHFFFAOYSA-N 0.000 abstract 1
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 abstract 1
- MNOILHPDHOHILI-UHFFFAOYSA-N Tetramethylthiourea Chemical compound CN(C)C(=S)N(C)C MNOILHPDHOHILI-UHFFFAOYSA-N 0.000 abstract 1
- LYVWMIHLNQLWAC-UHFFFAOYSA-N [Cl].[Cu] Chemical compound [Cl].[Cu] LYVWMIHLNQLWAC-UHFFFAOYSA-N 0.000 abstract 1
- JIYAUZMNUQFTOM-UHFFFAOYSA-N acetamidomethyl acetate Chemical compound CC(=O)NCOC(C)=O JIYAUZMNUQFTOM-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 229940027999 antiseptic and disinfectant aluminium agent Drugs 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- 229910017052 cobalt Inorganic materials 0.000 abstract 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- RDKCQRPSDOJYJM-UHFFFAOYSA-N n-(butoxymethyl)-2-chloroacetamide Chemical compound CCCCOCNC(=O)CCl RDKCQRPSDOJYJM-UHFFFAOYSA-N 0.000 abstract 1
- GYLDXXLJMRTVSS-UHFFFAOYSA-N n-butylacetamide Chemical compound CCCCNC(C)=O GYLDXXLJMRTVSS-UHFFFAOYSA-N 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 150000003016 phosphoric acids Chemical class 0.000 abstract 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
- C09B47/12—Obtaining compounds having alkyl radicals, or alkyl radicals substituted by hetero atoms, bound to the phthalocyanine skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention comprises acylaminomethylphthalocyanines of the formula <FORM:0806175/IV (c)/1> wherein Pc is a phthalocyanine radical, R1 and R2 are hydrogen atoms or alkyl groups, Z is hydrogen or halogen, alkoxy, dialkylamino, or alkylthio, and n is a number from 2 to 8, and also the corresponding bodies where Z is replaced by a quaternary ammonium, tertiary sulphonium, or isothiouronium group. The invention also comprises a process of preparing these bodies by reacing a phthalocyanine in a liquid or molten medium of an anhydrous acid or an anhydrous aluminium halide with a compound of the formula <FORM:0806175/IV (c)/2> in which A is hydroxy, alkoxy, acyloxy, or halogen, or with a mixture of a compound of the formula <FORM:0806175/IV (c)/3> and of monomeric or polymeric formaldehyde or dichlordimethyl ether. The reaction product may be hydrolysed to give the aminomethylphthalocyanines or converted into a quaternary ammonium, tertiary sulphonium or isothiouronium compound. Acids specified are sulphuric, phosphoric, aluminium chloride, and agents which split off water such as oleum, sulphur trioxide, acetic anhydride, phosphorus pentoxide, or meta- or poly-phosphoric acids may also be added. In examples: (1) copper, cobalt, iron, or nickel, or metal-free phthalocyanine or monochlor copper phthalocyanine is reacted with chloracetamide and paraformaldehyde, followed by hydrolysis of the copper product and conversion of some of the products to quaternary ammonium or isothiouronium compounds by reaction with pyridine, N,N-di-methylcyclohexylamine, tetramethylthiourea, tributylamine, N-methyl-, ethyl-, propyl-, or N,N-diethyl-thiourea; (2) copper phthalocyanine is reacted with paraformaldehyde and N-methyl-chloracetamide, a -chlorpropionic acid amide, bromacetamide, N-methylacetamide, N-ethyl or butyl acetamide, N,N-diethylaminoacetamide, or S-ethyl-thioacetamide, followed in some cases by further conversion as under (1); (3) copper phthalocyanine is reacted with N - hydroxymethylchloracetamide, N - chlormethylchloracetamide, N - butoxymethylchloracetamide, N - acetoxymethylacetamide, followed again by some conversions as under (1).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE806175X | 1955-07-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB806175A true GB806175A (en) | 1958-12-23 |
Family
ID=6722549
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB20665/56A Expired GB806175A (en) | 1955-07-13 | 1956-07-04 | Production of dyestuffs of the phthalocyanine series |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB806175A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3400161A1 (en) * | 1983-01-13 | 1984-07-19 | Sandoz-Patent-GmbH, 7850 Lörrach | Phthalocyanine compounds, their preparation and use |
| US5250111A (en) * | 1991-04-11 | 1993-10-05 | Ciba-Geigy Corporation | Pigment compositions |
-
1956
- 1956-07-04 GB GB20665/56A patent/GB806175A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3400161A1 (en) * | 1983-01-13 | 1984-07-19 | Sandoz-Patent-GmbH, 7850 Lörrach | Phthalocyanine compounds, their preparation and use |
| US5250111A (en) * | 1991-04-11 | 1993-10-05 | Ciba-Geigy Corporation | Pigment compositions |
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