GB967894A - Improvements relating to water-insoluble dye salts of the phthalocyanine series and their use in inks - Google Patents
Improvements relating to water-insoluble dye salts of the phthalocyanine series and their use in inksInfo
- Publication number
- GB967894A GB967894A GB4242160A GB4242160A GB967894A GB 967894 A GB967894 A GB 967894A GB 4242160 A GB4242160 A GB 4242160A GB 4242160 A GB4242160 A GB 4242160A GB 967894 A GB967894 A GB 967894A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dodecyl
- formula
- alkyl
- carbon atoms
- reacted
- 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
- 150000003839 salts Chemical class 0.000 title abstract 6
- 239000000976 ink Substances 0.000 title 1
- 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 1
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- -1 hydrocarbon radical Chemical class 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 abstract 3
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 2
- QCENGKPIBJNODL-UHFFFAOYSA-N n'-dodecylethane-1,2-diamine Chemical group CCCCCCCCCCCCNCCN QCENGKPIBJNODL-UHFFFAOYSA-N 0.000 abstract 2
- ARQIMFKLXJMELG-UHFFFAOYSA-N 1-dodecyl-4,5-dihydroimidazol-2-amine Chemical compound CCCCCCCCCCCCN1CCN=C1N ARQIMFKLXJMELG-UHFFFAOYSA-N 0.000 abstract 1
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 abstract 1
- MTIMDGQILFWMJI-UHFFFAOYSA-N 2-methylsulfanyl-4,5-dihydro-1h-imidazole Chemical compound CSC1=NCCN1 MTIMDGQILFWMJI-UHFFFAOYSA-N 0.000 abstract 1
- DISXFZWKRTZTRI-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-2-amine Chemical class NC1=NCCN1 DISXFZWKRTZTRI-UHFFFAOYSA-N 0.000 abstract 1
- MSYFITFSZJKRQJ-UHFFFAOYSA-N 4,5-dihydroimidazol-1-amine Chemical class NN1CCN=C1 MSYFITFSZJKRQJ-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000005263 alkylenediamine group Chemical group 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 abstract 1
- 229960005082 etohexadiol Drugs 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 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 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000003840 hydrochlorides Chemical class 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- YZPMGCUOUVFLJC-UHFFFAOYSA-N n'-decylethane-1,2-diamine Chemical group CCCCCCCCCCNCCN YZPMGCUOUVFLJC-UHFFFAOYSA-N 0.000 abstract 1
- QIBKKTQVKFEWCH-UHFFFAOYSA-N n'-tetradecylethane-1,2-diamine Chemical compound CCCCCCCCCCCCCCNCCN QIBKKTQVKFEWCH-UHFFFAOYSA-N 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- 150000003568 thioethers Chemical class 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
- C09B47/24—Obtaining compounds having —COOH or —SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
- C09B47/26—Amide radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
Hydrochlorides and hydrobromides of iminoimidazolidines of the formula: <FORM:0967894/C1/1> wherein A is ethylene or 1:3-propylene, R1 is an alkyl group of 10 to 14 carbon atoms or an aralkyl group having an alkyl substituent of 4 to 12 carbon atoms and R2 is hydrogen or an alkyl, cycloalkyl, aralkyl or aryl group are made by reacting an alkylene diamine of the formula R1-NH-A-NH-R2 with cyanogen chloride or cyanogen bromide. In examples (1) N-dodecyl-, N-decyl- and N-tetradecyl-ethylene diamine are reacted with cyanogen chloride; (2) N-octyl-N1-propyl-, N-dodecyl -N1- isobutyl-, N-dodecyl-N1-cyclohexyl- and N-dodecyl-N1-benzylethylene diamine are reacted with cyanogen bromide; (3) a mixture of N-dodecyl-ethylene diamine and N:N1-bis-dodecyl-ethylene diamine is reacted with cyanogen chloride; and (4) N-decyl-, N-dodecyl-, N-tetradecyl-, N-octyl -N1- methyl-, N-dodecyl -N1- cyclohexyl-, N-dodecyl -N1-benzyl- and N-dodecyl -N1- methyl-1:3-propylene diamine are reacted with cyanogen bromide. Amino-imidazolines of the formula: <FORM:0967894/C1/2> wherein R1 and A have the meanings given above and R3 is an alkyl, cycloalkyl, aralkyl or aryl group, are made by reacting a thioether of the formula: <FORM:0967894/C1/3> wherein R1 and A have the meanings above and the hydrocarbon radical is preferably an alkyl radical of at most 4 carbon atoms, with a primary amine R3-NH2. In an example (5) dodecylamine and decylamine are reacted with 2-methylmercapto-imidazoline.ALSO:The invention comprises water-insoluble salts of the formula <FORM:0967894/C4-C5/1> wherein Pc is a metal or metal-free phthalocyanine radical which is unsubstituted or contains one halogen atom attached to one of its benzo radicals, A is alkylene bound at a : b - or a : g -carbon atoms to the two nitrogen atoms, of R1, R2 and R3 at least one R is an alkyl grou having 10 to 14 carbon atoms or an aralkyl group which contains an alkyl substituent having 4 to 12 carbon atoms and the remaining R's are hydrogen, alkyl, cycloalkyl, aralkyl or aryl radicals, at least one being hydrogen, and m and n are each 1 or 2 and their sum is 2 or 3. The salts are made by reacting a compound of the formula <FORM:0967894/C4-C5/2> where Pc, m and n are as above and Z is a hydrogen, alkali metal or ammonium ion, with a compound of the formula <FORM:0967894/C4-C5/3> where A, R1, R2 and R3 are as above or a salt of such a compound in the presence of an alkali. Examples are given. The dye salts may be used in ink for ball-point pens or stamp pads. In an example (6) a dye salt made from copper phthalocyanine - monosulphonamide - monosulphonic acid and 1-dodecyl-2-iminoimidazolidine is dissolved in octylene glycol and benzyl alcohol to give a ball-point pen ink.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH8166559A CH379032A (en) | 1959-12-10 | 1959-12-10 | Process for the production of water-insoluble colored salts of the phthalocyanine series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB967894A true GB967894A (en) | 1964-08-26 |
Family
ID=4539018
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4242160A Expired GB967894A (en) | 1959-12-10 | 1960-12-09 | Improvements relating to water-insoluble dye salts of the phthalocyanine series and their use in inks |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH379032A (en) |
| ES (1) | ES263129A1 (en) |
| GB (1) | GB967894A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2404069A1 (en) * | 1973-02-01 | 1974-08-08 | Sandoz Ag | PHTHALOCYANINE COMPOUNDS, THEIR PRODUCTION AND USE |
-
1959
- 1959-12-10 CH CH8166559A patent/CH379032A/en unknown
-
1960
- 1960-12-09 ES ES0263129A patent/ES263129A1/en not_active Expired
- 1960-12-09 GB GB4242160A patent/GB967894A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2404069A1 (en) * | 1973-02-01 | 1974-08-08 | Sandoz Ag | PHTHALOCYANINE COMPOUNDS, THEIR PRODUCTION AND USE |
Also Published As
| Publication number | Publication date |
|---|---|
| ES263129A1 (en) | 1961-06-01 |
| CH379032A (en) | 1964-06-30 |
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