EP0662094A1 - Procede de production de films a l'alcool polyvinylique contenant des colorants et leur utilisation - Google Patents

Procede de production de films a l'alcool polyvinylique contenant des colorants et leur utilisation

Info

Publication number
EP0662094A1
EP0662094A1 EP94924739A EP94924739A EP0662094A1 EP 0662094 A1 EP0662094 A1 EP 0662094A1 EP 94924739 A EP94924739 A EP 94924739A EP 94924739 A EP94924739 A EP 94924739A EP 0662094 A1 EP0662094 A1 EP 0662094A1
Authority
EP
European Patent Office
Prior art keywords
polyvinyl alcohol
dye
containing polyvinyl
foils
film
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.)
Withdrawn
Application number
EP94924739A
Other languages
German (de)
English (en)
Inventor
Wolfgang Fischer
Sylvia Baum
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.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
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 Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of EP0662094A1 publication Critical patent/EP0662094A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N31/00—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods
    • G01N31/22—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods using chemical indicators
    • G01N31/221—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods using chemical indicators for investigating pH value
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment

Definitions

  • the invention relates to a process for the production of waterproof, dye-containing polyvinyl alcohol films and their use as a sensor membrane for determining the pH value.
  • Sensor membrane consists of a mechanically stable carrier element and a hydrophilic recording layer applied thereon, which contains an indicator dye in immobilized form.
  • the absorption layer consists of cellulose, gelatin, hydrogel, hydrophilic polyvinyl alcohols or mixtures of these substances. Reactive indicators are usually used as indicator dyes, i.e.
  • pH indicators that have a chemical function that enables chemical bonding to the absorption layer.
  • the invention has for its object to provide waterproof polyvinyl alcohol films for reversible pH measurement, which ensure rich colorations.
  • an uncrosslinked polyvinyl alcohol layer can be made waterproof not only by heating with acids or aldehydes, for example, but also by reacting it directly with reactive dye solutions.
  • the invention relates to a process for the production of waterproof, dye-containing polyvinyl alcohol films, which is characterized in that an uncrosslinked polyvinyl alcohol layer is reacted directly with a reactive dye solution.
  • Another object of the invention is the use of the polyvinyl alcohol film thus produced as a sensor membrane for the reversible optical display of the pH value of a sample.
  • a reactive dye solution By reacting an uncrosslinked polyvinyl alcohol film with a reactive dye solution and, in comparison, with a dye-free solution, it could be demonstrated that in the latter case no water resistance is achieved. It can be concluded from this that the water resistance developed is based directly on the reaction of the polyvinyl alcohol with the reactive dye. Since the number of free hydroxyl groups in the uncrosslinked polyvinyl alcohol is high, the process according to the invention results in a higher dye absorption and thus a rich color, which in turn allows more precise measurements. The covalently bound reactive dyes can no longer be washed out.
  • Typical chemical structures of reactive indicators are e.g.
  • the polyvinyl alcohol films obtained according to the invention are optically completely transparent and are therefore readily accessible to a photometric absorption measurement. In addition, they can be produced in large quantities at low cost. Due to the relatively thin film or indicator layer of approximately 0.1 to 20, preferably 1 to 10 ⁇ m, the film according to the invention has a very low buffer capacity, which it is used for the purpose of measuring unbuffered solution (for example when detecting acid rain) makes very suitable. The films have a fast response time because the protons can diffuse through the thin hydrophilic indicator layer much faster than through relatively thick layers.
  • the polyvinyl alcohol film according to the invention can of course also be applied to a solid support element e.g. made of hydrophobic, optically transparent material such as polyester of the phthalic acid ester type, polycarbonates, polyvinyl chlorides, polyamides, silicones, crosslinked polyacrylamides or polyvinyl alcohols.
  • a solid support element e.g. made of hydrophobic, optically transparent material such as polyester of the phthalic acid ester type, polycarbonates, polyvinyl chlorides, polyamides, silicones, crosslinked polyacrylamides or polyvinyl alcohols.
  • the waterproof, reactive dye-containing polyvinyl alcohol film is used as a sensor membrane for visual, photometric or reflectometric determination of the pH. It is also suitable for pH measurement in very weakly buffered solutions, e.g. of surface and rain water and for measuring physiological pH values.
  • Example 2 10% solution of polyvinyl alcohol applied with a coater in a film thickness of 10 ⁇ m. The layer is then dried at room temperature. This film is immersed in the coloring solution according to Example 2 for 45 minutes so that the polyvinyl alcohol film is completely covered with it. Then it is rinsed with water until it is evenly colored yellow and then dried.
  • Example 2
  • the film colored according to Example 1 is used for pH measurements in the range from pH 4 to 7, since it changes its color depending on the pH. If you dip pieces of the film (e.g. 2 ⁇ 10 cm) in buffer solutions, you get the following colors:

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Biochemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Immunology (AREA)
  • Pathology (AREA)
  • Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
  • Treatments Of Macromolecular Shaped Articles (AREA)

Abstract

L'invention concerne un procédé de production de films à l'alcool polyvinylique hydrofuges contenant des colorants et leur utilisation comme membrane de détection pour l'affichage optique réversible du pH d'un échantillon. La production s'effectue par réaction d'une couche d'alcool polyvinylique non réticulée avec une solution colorante réactive.
EP94924739A 1993-07-26 1994-07-12 Procede de production de films a l'alcool polyvinylique contenant des colorants et leur utilisation Withdrawn EP0662094A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19934324991 DE4324991A1 (de) 1993-07-26 1993-07-26 Verfahren zur Herstellung von Farbstoffe enthaltenden Polyvinylalkoholfolien und deren Verwendung
DE4324991 1993-07-26
PCT/EP1994/002269 WO1995003340A1 (fr) 1993-07-26 1994-07-12 Procede de production de films a l'alcool polyvinylique contenant des colorants et leur utilisation

Publications (1)

Publication Number Publication Date
EP0662094A1 true EP0662094A1 (fr) 1995-07-12

Family

ID=6493696

Family Applications (1)

Application Number Title Priority Date Filing Date
EP94924739A Withdrawn EP0662094A1 (fr) 1993-07-26 1994-07-12 Procede de production de films a l'alcool polyvinylique contenant des colorants et leur utilisation

Country Status (4)

Country Link
EP (1) EP0662094A1 (fr)
JP (1) JPH08502549A (fr)
DE (1) DE4324991A1 (fr)
WO (1) WO1995003340A1 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19634164A1 (de) 1996-08-23 1998-02-26 Bosch Siemens Hausgeraete System und Verfahren zur Anzeige alphanumerischer und/oder graphischer Zeichen
US6544794B1 (en) * 2000-05-12 2003-04-08 Shiseido Company, Ltd. Method for visual imaging of ion distribution in tissue
GB2408330B (en) * 2003-11-22 2008-12-03 Advanced Gel Technology Ltd Polymeric materials comprising pH indicators for use in wound dressings
US8242203B2 (en) 2005-11-10 2012-08-14 Eric Bakker Covalently attached nile blue derivatives for optical sensors
WO2007059449A2 (fr) * 2005-11-10 2007-05-24 Beckman Coulter, Inc. Derives de bleu de nil lies par covalence pour des sondes optiques
AT515010B1 (de) 2013-11-06 2018-03-15 Joanneum Res Forschungsgmbh Testeinrichtung zum Detektieren der An- oder Abwesenheit eines Analyten in einer flüssigen Probe sowie Verfahren zur Herstellung derselben
US9581551B2 (en) 2014-07-31 2017-02-28 Research & Business Foundation Sungkyunkwan University Color-change sensor using film for detecting harmful material
KR101590111B1 (ko) * 2014-07-31 2016-02-01 성균관대학교산학협력단 유해물질 검지용 필름형 색 변환 센서

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3544484A (en) * 1967-12-18 1970-12-01 American Standard Inc Optical ph indicator comprising aromatic aminoazo dye and inert polymer containing carbonyl radicals
JPS4943720B2 (fr) * 1972-09-16 1974-11-22
JPS5748905A (en) * 1980-09-05 1982-03-20 Kanebo Ltd Film type pack capable of discriminating peeling time by color change
JPS58103584A (ja) * 1981-12-15 1983-06-20 Ricoh Co Ltd 可逆性熱発色性組成物
DE59209350D1 (de) * 1991-09-30 1998-07-02 Merck Patent Gmbh SENSORMEMBRAN ZUR ANZEIGE DES pH-WERTES EINER PROBE, IHRE HERSTELLUNG UND VERWENDUNG

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9503340A1 *

Also Published As

Publication number Publication date
WO1995003340A1 (fr) 1995-02-02
JPH08502549A (ja) 1996-03-19
DE4324991A1 (de) 1995-02-02

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