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
  • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
  • C09B23/14—Styryl dyes
  • C09B23/145—Styryl dyes the ethylene chain carrying an heterocyclic residue, e.g. heterocycle-CH=CH-C6H5
• • 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
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
  • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
  • C07D311/78—Ring systems having three or more relevant rings
  • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
  • C07D311/82—Xanthenes
  • C07D311/84—Xanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
  • C07D311/86—Oxygen atoms, e.g. xanthones
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
  • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
  • C07D311/78—Ring systems having three or more relevant rings
  • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
  • C07D311/82—Xanthenes
  • C07D311/90—Xanthenes with hydrocarbon radicals, substituted by amino radicals, directly attached in position 9
• • 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
  • C09B11/28—Pyronines ; Xanthon, thioxanthon, selenoxanthan, telluroxanthon 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
  • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
  • C09B23/10—The polymethine chain containing an even number of >CH- groups
• • 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
  • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
  • C09B23/10—The polymethine chain containing an even number of >CH- groups
  • C09B23/107—The polymethine chain containing an even number of >CH- groups four >CH- groups
• • 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
  • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
  • Y10T428/00—Stock material or miscellaneous articles
  • Y10T428/25—Web or sheet containing structurally defined element or component and including a second component containing structurally defined particles

Definitions

• each R represents either a hydrogen atom or a lower alkyl group having from one to five carbon atoms and wherein n is an integer from 1 to 3.
• the present invention relates to initially colorless chromogenic, color precursor compounds having particular utility in the field of carbonless copying.
• the compounds of the present invention may be utilized, for example, in the production of self-marking impact papers of the transfer or manifolding type wherein a first marking ingredient is carried on one sheet of paper for reaction with a second marking ingredient normally carried on a mating sheet of paper.
• the invention relates to a family of chromogenic 9-(4- aminophenyl polymethine)-9-xanthenol color precursor compounds having the following structural formula:
• each R represents either a hydrogen atom or a lower alkyl group having from one to five carbon atoms and wherein n is an integer from 1 to 3.
• the top sheet of paper upon which the impact or pressure is immediately applied, ordinarily has its back surface coated with microscopic capsules containing one of the reactive ingredients which produces a mark.
• a receiver sheet, placed in contact with such back face of the top sheet has its front surface coated with a material having a component reactive with the contents of the capsules so that when capsules are ruptured upon impact by stylus or machine key, the initially colorless or substantially colorless contents of the ruptured capsules react with a coreactant therefor on the receiver sheet and a mark forms on the receiver sheet corresponding to the mark impressed by the stylus or machine key.
• impact transfer papers are designated by the terms CB, CFB and CF, which stand respectively for coated back, coated front and back" and coated front.”
• the CB sheet is usually the top sheet and the one on which the impact impression is directly made;
• the CFB sheets are the intermediate sheets, each of which have a mark formed on the front surface thereof and each of which also transmits the contents of ruptured capsules from its back surface to the front of the next succeeding sheet;
• the CF sheet is the last sheet and is only coated on its front surface to have an image formed thereon.
• the CF sheet is not 2 normally coated on its back surface as no further transfer is desired.
• carbonless impact transfer paper The most common variety of carbonless impact transfer paper, and the type with which the compounds of the present invention are preferably utilized, is the type illustrated, for example, in Green (U.S. Pat. No. 2,712,507) and Macaulay (U.S. Pat. No. 3,016,308) wherein microscopic capsules containing a liquid fill comprising a solution of an initially colorless chemically reactivecolor forming dye precursor are coated on the back surface of the sheet, and a dry coating of a co-reactant chemical for the dye precursor is coated on the front surface of a receiving sheet.
• Green U.S. Pat. No. 2,712,507
• Macaulay U.S. Pat. No. 3,016,308
• color precursors disclosed in the patents referred to above are capable of undergoing an acidbase type reaction with an acidic material.
• Other previously known color precursors are the spiro-dipyran compounds disclosed in the patent to I-Iarbort, US. Pat. No. 3,293,060 with specific reference being made to the disclosure of the US. Pat. No. 3,293,060 extending from column 11, line 32 through column 12, line 21.
• the color precursors disclosed in the patents listed above are initially generally colorless and capable of becoming highly colored when brought into contact with an acidic layer such as an acid-leached bentonitetype clay or an acid-reacting polymeric material, or the like.
• the color precursor materials disclosed above are dissolved in a solvent and the solution is encapsulated in accordance with the procedures and processes described and disclosed by Macaulay (US. Pat. No. 3,016,308) and by Green (US. Pat. No. 3,712,507) as mentioned above.
• Other processes for encapsulating color precursors are disclosed in US.
• Solvents known to be useful in connection with dissolving color precursors include chlorinated biphenyls, vegetable oils (castor oil, coconut oil, cotton seed oil, etc.), esters (dibutyl adipate, dibutyl phthalate, butyl benzyl adipate, benzyl octyl adipate, tricresyl phosphate, trioctyl phosphate, etc.), petroleum derivatives (petroleum spirits, kerosene, mineral oils, etc.), aromatic solvents (benzene, toluene, etc.), silicone oils, or combinations of the foregoing. Particularly useful are the alkylated naphthalene solvents disclosed in US. Pat. No. 3,805,463 to Konishi et a].
• the color precursors are conventionally contained in pressure rupturable microcapsules which are included in the back coatings of the sheets of carbonless copying manifolded sets.
• the acidic coatings are generally utilized as front coatings with the color precursor material in a solvent therefor being transferred from an adjacent back coating to the acidic layer front coating upon rupture of the capsules which contain the color precursor material.
• the present invention is directed to a family of normally substantially colorless chromogenic 9-(4- aminophenyl polymethine)-9-xanthenol color precursor compounds having a structural formula as set forth above. These compounds are initially substantially colorless; however, when brought into contact with a solid Lewis acid electron acceptor material such as the acidleached bentonite-type clay disclosed in the application of Baxter, Ser. No. 125,075, they may be converted into a highly colored form.
• Various other solid acidic materials which are generally capable of converting these compounds into their highly colored form are disclosed in U.S. Pat. No. 3,622,364, US. Pat. No. 3,330,722, US. Pat. No. 3,389,007 and US. Pat. No. 3,293,060 referred to above.
• n 1 may be prepared by reacting one mol of a p-amino benzaldehyde compound with 9-methyl-9- xanthenol in the presence of HCl and thereafter neutralizing the reaction product with a base in accordance with the following formula:
• the resultant ethereal solution was dried with Na SO and the ether was evaporated using a steam bath to present 16.0 grams (approximately 0.075 mole) of a deep yellow, gummy, partially crystalline product which was 9-methyl-9-xanthenol.
• duPont de Nemours which is a polyvinyl alcohol with 87 to 89% hydrolysis and a viscosity of 35 to 45 cps in a 4% aqueous solution at 20C) were placed in a semi-micro Waring blender and then solutions A and B were mixed together at room temperature and the resultant solution was added to the Elvanol solution in the blender.
• the blender was activated and high shear agitation was continued for about 2 minutes until an emulsion having a dispersed phase particle size of about 2 to 10 microns was obtained.
• the aqueous solution containing the Elvanol polyvinyl alcohol formed the continuous phase and the solution containing the R- l 00 solvent, the 9-(4-dimethyl-aminophenyl polymethine)-9-xanthenol and terephthaloyl chloride formed the dispersed phase.
• the emulsion was then transferred to a suitable container such as a beaker and was stirred with a variable speed mechanical stirrer t 300 to 500 7 rpm while an aqueous solution containing L86 gms of diethylene triamine, 1.20 gms of sodium carbonate and ml of water was added.
• microcapsules containing the 9-(4-dimethylaminophenyl polymethine)-9-xanthenol compound was then brought into contact with an acid-leached clay coating on the surface of another sheet of paper and when an impression was made on the reverse side of the sheet coated with microcapsules a corresponding blue colored reproduction of such impression appeared on the acid-leached clay coating 'within approximately 30 seconds.
• Example IV EXAMPLE IV
• the procedures and quantities of materials were identical with Example 111, except that in this instance, dibutyl phthalate was utilized as the solvent for the dispersed phase rather than R-lOO.
• the results were identical with those obtained in Example 111.
• the compounds of the present invention are useful generally in the production and generation of colored marks and it is not critical to the present invention that the same be utilized in a copying system or in a microencapsulated form.
• a 9-(4-aminophenyl polymethine)-9-xanthenol compound having the following structural formula:
• each R represents either a hydrogen atom or a lower alkyl group having from one to five carbon atoms and wherein n is an integer from 1 to 3.
• a method for preparing a xanthenol compound as set forth in claim 1 comprising reacting one molar equivalent of a p-aminobenzaldehyde compound with one molar equivalent of 9-methyl-9-xanthenol.
• a method for preparing a xanthenol compound as set forth in claim 1 comprising reacting one molar equivalent of a 3-(p-aminophenyl) propenal compound with one molar equivalent of 9-methyl9-xanthenol.
• a method for preparing a xanthenol compound as set forth in claim 1 comprising reacting one molar equivalent of a S-(p-aminophenyl) pentadienal compound with one molar equivalent of 9-methyl-9-xanthenol.
• a pressure-sensitive recording system comprising a layer of microcapsules containing a substantially colorless color precursor compound and a layer of an electron-acceptor material, the improvement which comprises utilizing, as said color precursor compound, a xanthenol compound as set forth in claim 1.
• a pressure-sensitive recording system comprising a layer of microcapsules containing a substantially colorless color precursor compound and a layer of an electron-acceptor material, the improvement which comprises utilizing, as said color precursor compound, a xanthenol compound as set forth in claim 2.
• a pressure-sensitive recording system comprising a'layer containing a substantially colorless color precursor compound and a layer of an electron-acceptor material, the improvement which comprises utilizing, as said color precursor compound, a xanthenol compound as set forth in claim 1.
• a pressure-sensitive recording system comprising a layer containing a substantially colorless color precursor compound and a layer of an electron-acceptor material, the improvement which comprises utilizing, as said color precursor compound, a xanthenol compound as set forth in claim 2.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Color Printing (AREA)
• Pyrane Compounds (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Priority Applications (10)

Applications Claiming Priority (1)

Publications (1)

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Family Applications (1)

Country Status (9)

Cited By (4)

Citations (5)

Family Cites Families (1)

• 1974
  • 1974-11-21 US US525988A patent/US3930108A/en not_active Expired - Lifetime
• 1975
  • 1975-10-24 ZA ZA00756701A patent/ZA756701B/xx unknown
  • 1975-11-11 DE DE19752550486 patent/DE2550486A1/de active Pending
  • 1975-11-13 AU AU86572/75A patent/AU8657275A/en not_active Expired
  • 1975-11-20 FR FR7535462A patent/FR2291976A1/fr active Granted
  • 1975-11-20 IT IT52313/75A patent/IT1052342B/it active
  • 1975-11-20 NL NL7513595A patent/NL7513595A/xx not_active Application Discontinuation
  • 1975-11-20 JP JP50139684A patent/JPS5174026A/ja active Pending
  • 1975-11-20 BE BE162031A patent/BE835764A/xx unknown
• 1976
  • 1976-12-10 JP JP14861376A patent/JPS5292618A/ja active Pending

Patent Citations (5)

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