GB1082918A - Quaternary leucoauramine compounds - Google Patents
Quaternary leucoauramine compoundsInfo
- Publication number
- GB1082918A GB1082918A GB26287/66A GB2628766A GB1082918A GB 1082918 A GB1082918 A GB 1082918A GB 26287/66 A GB26287/66 A GB 26287/66A GB 2628766 A GB2628766 A GB 2628766A GB 1082918 A GB1082918 A GB 1082918A
- Authority
- GB
- United Kingdom
- Prior art keywords
- atom
- formula
- compounds
- alkyl
- heterocyclic
- 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
- 150000001875 compounds Chemical class 0.000 title abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 125000000623 heterocyclic group Chemical group 0.000 abstract 5
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 239000002243 precursor Substances 0.000 abstract 2
- 150000003512 tertiary amines Chemical class 0.000 abstract 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 abstract 1
- QPLPYHIOJBFZNG-UHFFFAOYSA-N 6-[(6-amino-1,4-dimethylcyclohexa-2,4-dien-1-yl)-(1-methylpiperazin-2-yl)methyl]-3,6-dimethylcyclohexa-2,4-dien-1-amine Chemical compound CC1(C(C=C(C=C1)C)N)C(C1N(CCNC1)C)C1(C(C=C(C=C1)C)N)C QPLPYHIOJBFZNG-UHFFFAOYSA-N 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000000732 arylene group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 229910000278 bentonite Inorganic materials 0.000 abstract 1
- 239000000440 bentonite Substances 0.000 abstract 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 abstract 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 1
- 229940073608 benzyl chloride Drugs 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 239000003086 colorant Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- UBNCABDIHVVYRP-UHFFFAOYSA-N dimethylamino(diphenyl)methanol Chemical compound C=1C=CC=CC=1C(O)(N(C)C)C1=CC=CC=C1 UBNCABDIHVVYRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
- B41M5/132—Chemical colour-forming components; Additives or binders therefor
- B41M5/136—Organic colour formers, e.g. leuco dyes
-
- 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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/02—Diaryl- or thriarylmethane dyes derived from diarylmethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention comprises quaternary leucoauramine compounds of formula <FORM:1082918/C4-C5/1> wherein R is an alkyl group <FORM:1082918/C4-C5/2> is a heterocyclic nucleus containing 5 or 6 members, R1 is alkyl, cycloalkyl or aralkyl, R2 is alkyl and A- is an anion; or of formula <FORM:1082918/C4-C5/3> wherein <FORM:1082918/C4-C5/4> is a heterocyclic nucleus containing 5 or 6 members, n is 1-18, R3 is alkyl or R2 and R3 are linked to form with the N+ atom a heterocyclic group; or of formula <FORM:1082918/C4-C5/5> wherein X is H, alkyl, aryl, alkaryl or aralkyl; or of formula <FORM:1082918/C4-C5/6> wherein Y is arylene; or of formula <FORM:1082918/C4-C5/7> wherein Z is a heterocyclic nucleus containing 5 or 6 ring members linked to the indicated N atom through a ring C atom. The compounds are prepared by quaternizing a tertiary amine corresponding to one of the above formulae. The tertiary amines are prepared by condensing a 4,41 - bis (dialkylamino) - benzhydrol with an appropriate secondary amine. The compounds are used in the production of impact-sensitive copy sheets (see Divisions D1-D2). In examples 4,41-bis (dimethylamino)-benzhydrol is refluxed in MeOH with N-methyl-piperazine to yield bis (p-dimethyl-amino-phenyl) - N1 - methyl - piperazinyl - methane which is quaternized with dimethyl or diethyl sulphate or benzyl chloride.ALSO:Lencoausamine compounds of formula <FORM:1082918/D1-D2/1> wherein R is an alkyl group and the N atom is substituted by a group containing a quarternary N atom or is part of a heterocyclic ring containing a quaternary N atom (see Division C4-5) are used as colour precursors in impact-sensitive copy sheets. The compounds are water-soluble and may be applied to paper as a coating in the internal phase of an aqueous wax emulsion (water-in-oil type). The precursors develop blue colours on contact with acid substances such as niccinic acid or bentonite.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46394265A | 1965-06-14 | 1965-06-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1082918A true GB1082918A (en) | 1967-09-13 |
Family
ID=23841895
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB26287/66A Expired GB1082918A (en) | 1965-06-14 | 1966-06-13 | Quaternary leucoauramine compounds |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3467658A (en) |
| GB (1) | GB1082918A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3874884A (en) * | 1971-10-27 | 1975-04-01 | Lamson Industries Ltd | Coating compositions |
| DE2414201C3 (en) * | 1973-03-26 | 1978-04-06 | Canon K.K., Tokio | Current sensitive recording material |
| US5458793A (en) * | 1993-05-13 | 1995-10-17 | The Lubrizol Corporation | Compositions useful as additives for lubricants and liquid fuels |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3375279A (en) * | 1961-02-20 | 1968-03-26 | Air Reduction | Dialkynyl amines |
-
1965
- 1965-06-14 US US463942A patent/US3467658A/en not_active Expired - Lifetime
-
1966
- 1966-06-13 GB GB26287/66A patent/GB1082918A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3467658A (en) | 1969-09-16 |
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