US2828342A - N-(alkylhalophenyl) derivatives of leucauramine - Google Patents
N-(alkylhalophenyl) derivatives of leucauramine Download PDFInfo
- Publication number
- US2828342A US2828342A US558194A US55819456A US2828342A US 2828342 A US2828342 A US 2828342A US 558194 A US558194 A US 558194A US 55819456 A US55819456 A US 55819456A US 2828342 A US2828342 A US 2828342A
- Authority
- US
- United States
- Prior art keywords
- methyl
- leucauramine
- derivatives
- chloro
- bromo
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000001448 anilines Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- MAUMSNABMVEOGP-UHFFFAOYSA-N (methyl-$l^{2}-azanyl)methane Chemical compound C[N]C MAUMSNABMVEOGP-UHFFFAOYSA-N 0.000 description 1
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 1
- -1 2-methyl,4-bromophenyl Chemical group 0.000 description 1
- FBEHFRAORPEGFH-UHFFFAOYSA-N Allyxycarb Chemical compound CNC(=O)OC1=CC(C)=C(N(CC=C)CC=C)C(C)=C1 FBEHFRAORPEGFH-UHFFFAOYSA-N 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- 239000005083 Zinc sulfide Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910000286 fullers earth Inorganic materials 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- QTWZICCBKBYHDM-UHFFFAOYSA-N leucomethylene blue Chemical compound C1=C(N(C)C)C=C2SC3=CC(N(C)C)=CC=C3NC2=C1 QTWZICCBKBYHDM-UHFFFAOYSA-N 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- XWEDAOHUHOHFPJ-UHFFFAOYSA-N n-bromo-n-methylaniline Chemical compound CN(Br)C1=CC=CC=C1 XWEDAOHUHOHFPJ-UHFFFAOYSA-N 0.000 description 1
- 239000012254 powdered material Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S101/00—Printing
- Y10S101/29—Printing involving a color-forming phenomenon
Definitions
- alkylhalo derivatives of N-phenyl leucauramine are much more suitable for the manifold systems mentioned than the unsubstituted known N-phenyl leucauramine, because they are less volatile, they have increased solubility in oil, and they are much more stable compounds in the leuco form when subjected to the atmosphere and'light.
- the leucauramine derivatives also. are useful .in, solid powdered formas one of two solid .powdered materials 5 placed by an alkylhalo substituted phenyl group.
- One process of--making the novel compounds consists of the steps ofqicondensing molar equivalents of Michlers hydrolan'd aiselected alkylhalo derivative of aniline in hot ethyhalcohol; concentrating the reaction mixture 'as far as necessary to cause precipitation on cooling; filtering;.puri fying the crude materialby heating a benzene solution of'it .with fullerswearth and activated charcoal; and then precipitatingout the reaction product by'the addition of petroleum ether.
- the general equaftion'for this reactionis as' follows:
- the novel derivatives of this invention may be con- 50 sidered as derivativesof leucauramine in that one of the hydrogen atoms attached tothe (1) N has been replaced by an alkylhalo substituted phenyl group.
- methylchloro and methylbromo derivatives mentioned in the first paragraph of the specification may be made by using a methylchloro or methylbromo aniline with the methyl and chloro or bromo substitue'nts'in the desired positions, in the same procedure just outlined with respect to the preparation of N-(2-methyl,5-chlorophenyl) leucaurarnine, the molecular proportions being the same.
- a typical N-(methylbromophenyl)leucauramine is prepared as follows:
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Saccharide Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL212407D NL212407A (xx) | 1956-01-10 | ||
| BE552981D BE552981A (xx) | 1956-01-10 | ||
| US558194A US2828342A (en) | 1956-01-10 | 1956-01-10 | N-(alkylhalophenyl) derivatives of leucauramine |
| GB39596/56A GB804087A (en) | 1956-01-10 | 1956-12-31 | Derivatives of leucauramine |
| FR1168390D FR1168390A (fr) | 1956-01-10 | 1957-01-09 | Dérivés n-(alkylhalophényle) de la leucauramine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US558194A US2828342A (en) | 1956-01-10 | 1956-01-10 | N-(alkylhalophenyl) derivatives of leucauramine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2828342A true US2828342A (en) | 1958-03-25 |
Family
ID=24228555
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US558194A Expired - Lifetime US2828342A (en) | 1956-01-10 | 1956-01-10 | N-(alkylhalophenyl) derivatives of leucauramine |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2828342A (xx) |
| BE (1) | BE552981A (xx) |
| FR (1) | FR1168390A (xx) |
| GB (1) | GB804087A (xx) |
| NL (1) | NL212407A (xx) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2981733A (en) * | 1958-05-12 | 1961-04-25 | Allied Chem | N-bis(p-dialkylaminophenyl)methyl derivatives of nitrogen-containing saturated heterocyclic compounds |
| US2983756A (en) * | 1958-05-13 | 1961-05-09 | Allied Chem | Aliphatic amino derivatives of bis (p-dialkylaminophenyl) methane |
| US3995088A (en) * | 1974-02-01 | 1976-11-30 | Ciba-Geigy Corporation | Coated pressure-sensitive recording material |
| US4927802A (en) * | 1988-12-09 | 1990-05-22 | Ppg Industries, Inc. | Pressure-sensitive multi-part record unit |
| US5194390A (en) * | 1988-07-05 | 1993-03-16 | Miles Inc. | Composition for the assay of albumin |
| EP0587184A2 (en) * | 1992-09-10 | 1994-03-16 | New Oji Paper Co., Ltd. | Pressure sensitive recording materials |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1202921B (de) * | 1958-05-12 | 1965-10-14 | Allied Chem | Verfahren zur Herstellung von N-Bis-(p-dialkylaminoaryl)-methylderivaten gesaettigter heterocyclischer Stickstoffverbindungen |
-
0
- NL NL212407D patent/NL212407A/xx unknown
- BE BE552981D patent/BE552981A/xx unknown
-
1956
- 1956-01-10 US US558194A patent/US2828342A/en not_active Expired - Lifetime
- 1956-12-31 GB GB39596/56A patent/GB804087A/en not_active Expired
-
1957
- 1957-01-09 FR FR1168390D patent/FR1168390A/fr not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2981733A (en) * | 1958-05-12 | 1961-04-25 | Allied Chem | N-bis(p-dialkylaminophenyl)methyl derivatives of nitrogen-containing saturated heterocyclic compounds |
| US2983756A (en) * | 1958-05-13 | 1961-05-09 | Allied Chem | Aliphatic amino derivatives of bis (p-dialkylaminophenyl) methane |
| US3995088A (en) * | 1974-02-01 | 1976-11-30 | Ciba-Geigy Corporation | Coated pressure-sensitive recording material |
| US5194390A (en) * | 1988-07-05 | 1993-03-16 | Miles Inc. | Composition for the assay of albumin |
| US4927802A (en) * | 1988-12-09 | 1990-05-22 | Ppg Industries, Inc. | Pressure-sensitive multi-part record unit |
| EP0587184A2 (en) * | 1992-09-10 | 1994-03-16 | New Oji Paper Co., Ltd. | Pressure sensitive recording materials |
| EP0587184A3 (en) * | 1992-09-10 | 1995-08-02 | Kanzaki Paper Mfg Co Ltd | Materials for pressure sensitive recording. |
Also Published As
| Publication number | Publication date |
|---|---|
| NL212407A (xx) | |
| FR1168390A (fr) | 1958-12-08 |
| GB804087A (en) | 1958-11-05 |
| BE552981A (xx) |
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