EP0056157A1 - Utilisation de composés 7-hydroxy-coumarine pour l'imprégnation du papier - Google Patents

Utilisation de composés 7-hydroxy-coumarine pour l'imprégnation du papier Download PDF

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Publication number
EP0056157A1
EP0056157A1 EP81110811A EP81110811A EP0056157A1 EP 0056157 A1 EP0056157 A1 EP 0056157A1 EP 81110811 A EP81110811 A EP 81110811A EP 81110811 A EP81110811 A EP 81110811A EP 0056157 A1 EP0056157 A1 EP 0056157A1
Authority
EP
European Patent Office
Prior art keywords
phenyl
alkyl
hydroxy
coumarin compounds
chlorine
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.)
Granted
Application number
EP81110811A
Other languages
German (de)
English (en)
Other versions
EP0056157B1 (fr
Inventor
Horst Dr. Harnisch
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP0056157A1 publication Critical patent/EP0056157A1/fr
Application granted granted Critical
Publication of EP0056157B1 publication Critical patent/EP0056157B1/fr
Expired legal-status Critical Current

Links

Classifications

    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D21H21/30—Luminescent or fluorescent substances, e.g. for optical bleaching
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D21H21/28—Colorants ; Pigments or opacifying agents
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D21H21/40—Agents facilitating proof of genuineness or preventing fraudulent alteration, e.g. for security paper
    • D21H21/44—Latent security elements, i.e. detectable or becoming apparent only by use of special verification or tampering devices or methods
    • D21H21/46—Elements suited for chemical verification or impeding chemical tampering, e.g. by use of eradicators
    • 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
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/914—Transfer or decalcomania
    • Y10S428/915—Fraud or tamper detecting
    • 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
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/916—Fraud or tamper detecting

Definitions

  • German Offenlegungsschrift 27 47 349 emphasizes the superiority of pyranine for impregnating counterfeit-proof papers over previously used indicators.
  • compounds of the formula I can advantageously be used to impregnate such papers, despite the absence of sulfonic acid groups which make water soluble. They show a superior yellow effect when exposed to alkaline ink extinguishers . or red coloring, which is characterized by high color strength and durability.
  • Heterocyclic radicals A can, for example, the oxazole, benzoxazole, thiazole, benzthiazole, imidazole, benzimidazole, furan, benzo [b] furan, thiophene, benzo [b] thiophene, pyridine, quinoline, Pyrimidine, quinazolone, quinoxaline, 1,2,4-benzthiadiazine-1,1-dioxide, 1,3,4-oxadiazole, 1,3,4-thiadiazole, 1,2,3-triazole 1-, 1,2,3-triazole-2-, 1,2,4-triazole-1 or benzo-s-triazole series belong to the benzanellated heterocycles listed, a further benzo ring may also be fused.
  • Preferred heterocyclic radicals A are those of the benzothiazole, benzoxazole, benzimidazole, quinazol-4-one, benz [b] furan, benz [b] thiophene, 5-phenyl-1,3,4-oxadiazole, 5-phenyl-1,3,4-thiadiazole or pyridine series.
  • Suitable functionally modified carboxyl groups are in particular C 1 - to C 4 -alkyl esters, carbonamides, carbopiperidide, carbopyrrolidide, carbomorpholide, carbothiomorpholide, carbopiperazide and the nitrile group, optionally substituted by 1 - 2 C 1 - to C 4 -alkyl radicals.
  • an aqueous mineral acid such as hydrochloric acid or sulfur acid
  • the 7-hydroxy-coumarin compounds of the formula I are advantageously in the form of an aqueous suspension or dispersion with an active ingredient content of 0.01 to 0.5, preferably 0.05 to 0.2 percent by weight in the pH range below 6, in particular from 5 to 1.
  • a very fine distribution can advantageously be achieved by adding 1-10 percent by weight of an acid-resistant, preferably nonionic, dispersant, such as, for example, a polyether made from oleyl alcohol and 20-50 mol ethylene oxide.
  • a paper glue is advantageously produced from the dispersion obtained by adding a conventional sizing agent, such as oxidized starch (5-15% by weight), and a paper is impregnated with it in such a way that the concentration is about 0.05 to 0.2 g of reagent per m is 2 .
  • a white paper is obtained which, when treated with an ink eraser or other alkaline reagent, gives a strong, very stable yellow or red color.
  • 0.1 g compound of the formula prepared by condensation of benzoxazol-2-yl-ethyl acetate and resorcylaldehyde in boiling ethanol with piperidine acetate as catalyst, are finely dispersed in 100 ml of water with the addition of 0.005 g of a dispersant (polyether from oleyl alcohol and 50 mol of ethylene oxide), and 10 g of oxidized starch are added and adjusted to pH 2 with hydrochloric acid.
  • a paper is impregnated with the dispersion obtained in such a way that the concentration is about 0.1 g reagent / m 2 .
  • a white paper is obtained which, when treated with an ink eraser, gives a strong, yellow-green, very stable color.

Landscapes

  • Paper (AREA)
  • Plural Heterocyclic Compounds (AREA)
EP81110811A 1981-01-08 1981-12-29 Utilisation de composés 7-hydroxy-coumarine pour l'imprégnation du papier Expired EP0056157B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19813100295 DE3100295A1 (de) 1981-01-08 1981-01-08 Verwendung von 7-hydroxy-cumarin-verbindungen zum impraegnieren von papier
DE3100295 1981-01-08

Publications (2)

Publication Number Publication Date
EP0056157A1 true EP0056157A1 (fr) 1982-07-21
EP0056157B1 EP0056157B1 (fr) 1985-05-29

Family

ID=6122292

Family Applications (1)

Application Number Title Priority Date Filing Date
EP81110811A Expired EP0056157B1 (fr) 1981-01-08 1981-12-29 Utilisation de composés 7-hydroxy-coumarine pour l'imprégnation du papier

Country Status (3)

Country Link
US (1) US4411946A (fr)
EP (1) EP0056157B1 (fr)
DE (2) DE3100295A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2647820A1 (fr) * 1989-06-01 1990-12-07 Aussedat Rey Papier de securite infalsifiable et composition aqueuse ou organique utile, notamment pour rendre un papier infalsifiable

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2943074B1 (fr) * 2009-03-13 2011-05-20 Arjowiggins Security Substrat marquable au laser et procede de fabrication associe

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2410702A1 (fr) * 1977-12-05 1979-06-29 Tullis Russell Co Ltd Papier de securite renfermant un indicateur de produit effaceur
EP0027529A1 (fr) * 1979-09-15 1981-04-29 BASF Aktiengesellschaft Dérivés de la coumarine et leur utilisation pour la teinture de fibres synthétiques ou de matières plastiques

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2673186A (en) * 1948-01-15 1954-03-23 Procter & Gamble Alkaline detergent composition
US3886083A (en) * 1974-05-09 1975-05-27 American Bank Note Co Safety inks and documents
FR2365656A1 (fr) * 1976-05-25 1978-04-21 Arjomari Prioux Papier de securite

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2410702A1 (fr) * 1977-12-05 1979-06-29 Tullis Russell Co Ltd Papier de securite renfermant un indicateur de produit effaceur
EP0027529A1 (fr) * 1979-09-15 1981-04-29 BASF Aktiengesellschaft Dérivés de la coumarine et leur utilisation pour la teinture de fibres synthétiques ou de matières plastiques

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2647820A1 (fr) * 1989-06-01 1990-12-07 Aussedat Rey Papier de securite infalsifiable et composition aqueuse ou organique utile, notamment pour rendre un papier infalsifiable

Also Published As

Publication number Publication date
DE3100295A1 (de) 1982-08-05
US4411946A (en) 1983-10-25
DE3170783D1 (en) 1985-07-04
EP0056157B1 (fr) 1985-05-29

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