WO1995003340A1 - Verfahren zur herstellung von farbstoffe enthaltenden polyvinylalkoholfolien und deren verwendung - Google Patents
Verfahren zur herstellung von farbstoffe enthaltenden polyvinylalkoholfolien und deren verwendung Download PDFInfo
- Publication number
- WO1995003340A1 WO1995003340A1 PCT/EP1994/002269 EP9402269W WO9503340A1 WO 1995003340 A1 WO1995003340 A1 WO 1995003340A1 EP 9402269 W EP9402269 W EP 9402269W WO 9503340 A1 WO9503340 A1 WO 9503340A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polyvinyl alcohol
- dye
- containing polyvinyl
- foils
- film
- Prior art date
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:
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Immunology (AREA)
- Molecular Biology (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Physics & Mathematics (AREA)
- Physics & Mathematics (AREA)
- Pathology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP7504904A JPH08502549A (ja) | 1993-07-26 | 1994-07-12 | 染料含有ポリビニルアルコールフィルムの製造及びその用途 |
EP94924739A EP0662094A1 (de) | 1993-07-26 | 1994-07-12 | Verfahren zur herstellung von farbstoffe enthaltenden polyvinylalkoholfolien und deren verwendung |
Applications Claiming Priority (2)
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 |
DEP4324991.4 | 1993-07-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1995003340A1 true WO1995003340A1 (de) | 1995-02-02 |
Family
ID=6493696
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1994/002269 WO1995003340A1 (de) | 1993-07-26 | 1994-07-12 | Verfahren zur herstellung von farbstoffe enthaltenden polyvinylalkoholfolien und deren verwendung |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP0662094A1 (de) |
JP (1) | JPH08502549A (de) |
DE (1) | DE4324991A1 (de) |
WO (1) | WO1995003340A1 (de) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0831391A2 (de) | 1996-08-23 | 1998-03-25 | Bosch-Siemens HausgerÀ¤te GmbH | System und Verfahren zur Anzeige alphanumerischer und/oder graphischer Zeichen |
GB2408330A (en) * | 2003-11-22 | 2005-05-25 | Advanced Gel Technology Ltd | Polymeric materials for assessing pH |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6544794B1 (en) * | 2000-05-12 | 2003-04-08 | Shiseido Company, Ltd. | Method for visual imaging of ion distribution in tissue |
US8242203B2 (en) | 2005-11-10 | 2012-08-14 | Eric Bakker | Covalently attached nile blue derivatives for optical sensors |
WO2007059449A2 (en) * | 2005-11-10 | 2007-05-24 | Beckman Coulter, Inc. | Covalently attached nile blue derivatives for optical sensors |
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 |
Citations (5)
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 |
JPS4952289A (de) * | 1972-09-16 | 1974-05-21 | ||
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 |
WO1993007483A1 (de) * | 1991-09-30 | 1993-04-15 | Merck Patent Gmbh | SENSORMEMBRAN ZUR ANZEIGE DES pH-WERTES EINER PROBE, IHRE HERSTELLUNG UND VERWENDUNG |
-
1993
- 1993-07-26 DE DE19934324991 patent/DE4324991A1/de not_active Withdrawn
-
1994
- 1994-07-12 WO PCT/EP1994/002269 patent/WO1995003340A1/de not_active Application Discontinuation
- 1994-07-12 JP JP7504904A patent/JPH08502549A/ja active Pending
- 1994-07-12 EP EP94924739A patent/EP0662094A1/de not_active Withdrawn
Patent Citations (5)
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 |
JPS4952289A (de) * | 1972-09-16 | 1974-05-21 | ||
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 |
WO1993007483A1 (de) * | 1991-09-30 | 1993-04-15 | Merck Patent Gmbh | SENSORMEMBRAN ZUR ANZEIGE DES pH-WERTES EINER PROBE, IHRE HERSTELLUNG UND VERWENDUNG |
Non-Patent Citations (4)
Title |
---|
DATABASE WPI Section Ch Week 7437, Derwent World Patents Index; Class A10, AN 74-65335 * |
DATABASE WPI Section Ch Week 8217, Derwent World Patents Index; Class A12, AN 82-34269 * |
DATABASE WPI Section Ch Week 8330, Derwent World Patents Index; Class A03, AN 83-720404 * |
Z. ZHUJUN ET AL.: "Poly(vinyl alcohol) as a substrate for indicator immobilization for fibre-optic chemical sensors.", ANALYTICAL CHEMISTRY, vol. 61, no. 3, 1 February 1989 (1989-02-01), COLUMBUS US, pages 202 - 205 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0831391A2 (de) | 1996-08-23 | 1998-03-25 | Bosch-Siemens HausgerÀ¤te GmbH | System und Verfahren zur Anzeige alphanumerischer und/oder graphischer Zeichen |
GB2408330A (en) * | 2003-11-22 | 2005-05-25 | Advanced Gel Technology Ltd | Polymeric materials for assessing pH |
GB2408330B (en) * | 2003-11-22 | 2008-12-03 | Advanced Gel Technology Ltd | Polymeric materials comprising pH indicators for use in wound dressings |
Also Published As
Publication number | Publication date |
---|---|
JPH08502549A (ja) | 1996-03-19 |
EP0662094A1 (de) | 1995-07-12 |
DE4324991A1 (de) | 1995-02-02 |
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