WO1997047966A1 - OPTICAL SENSOR SYSTEM FOR pH DETERMINATION INDEPENDENTLY OF THE ION STRENGTH USING FLUORESCEIN BOUND TO A POLYMER VIA A URETHANE AND/OR UREA GROUP - Google Patents

OPTICAL SENSOR SYSTEM FOR pH DETERMINATION INDEPENDENTLY OF THE ION STRENGTH USING FLUORESCEIN BOUND TO A POLYMER VIA A URETHANE AND/OR UREA GROUP Download PDF

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Publication number
WO1997047966A1
WO1997047966A1 PCT/EP1997/003037 EP9703037W WO9747966A1 WO 1997047966 A1 WO1997047966 A1 WO 1997047966A1 EP 9703037 W EP9703037 W EP 9703037W WO 9747966 A1 WO9747966 A1 WO 9747966A1
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WO
WIPO (PCT)
Prior art keywords
optical sensor
polyurethane
weight
urea
thermoplastic
Prior art date
Application number
PCT/EP1997/003037
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English (en)
French (fr)
Inventor
Steven Mark Barnard
Dirk Beckelmann
Joseph Berger
Marizel Rouilly
Adrian Waldner
Original Assignee
Novartis 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 Novartis Ag filed Critical Novartis Ag
Priority to AU31753/97A priority Critical patent/AU3175397A/en
Priority to EP97927171A priority patent/EP0906566A1/en
Priority to JP10501204A priority patent/JP2000512754A/ja
Publication of WO1997047966A1 publication Critical patent/WO1997047966A1/en

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Classifications

    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01J—MEASUREMENT OF INTENSITY, VELOCITY, SPECTRAL CONTENT, POLARISATION, PHASE OR PULSE CHARACTERISTICS OF INFRARED, VISIBLE OR ULTRAVIOLET LIGHT; COLORIMETRY; RADIATION PYROMETRY
    • G01J3/00—Spectrometry; Spectrophotometry; Monochromators; Measuring colours
    • G01J3/28—Investigating the spectrum
    • G01J3/44—Raman spectrometry; Scattering spectrometry ; Fluorescence spectrometry
    • G01J3/4406—Fluorescence spectrometry
    • 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
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/84—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving inorganic compounds or pH

Definitions

  • the invention relates to an optical sensor for pH determination independently of the ion strength which comprises a solid polyurethane, polyurea-urethane or polyurea composition containing pH-sensitive fluorescem bound via a urethane and/or urea group in the form of a membrane on a transparent support material
  • the invention also relates to an optical fluorescence method which permits high-accuracy pH determination independently of the ion strength of the measurement solution
  • the method is particularly suitable for determining the pH of physiological solutions, in particular for determining the pH of blood
  • WO 90/00572 describes a sensor for pH determination and partial pressure determination of CO z which comprises a polyurethane hydrogel in which up to 20 % of an azo dye has been copolymerized The azo dye changes its absorption spectrum as a function of the pH, so that pH determination can be carried out via an absorption measurement The effect of the ion strength on the measurement result is not described
  • EP-A-481 740 describes in general terms polyether-polyurethanes in combination with a covalently bound fluorescence dye for pH determination, but no mention is made anywhere of the extent of the effect of ion strength on the measured signal
  • WO 94/28786 describes, for example, a composition of polyurethane acrylate prepolymer and fluorescem acrylamide which is copolymerized on a glass fibre with the aid of a photoinitiator, giving a pH-sensitive sensor whose sensitivity range can be varied within narrow limits by the prepolymer fluorescem acrylamide ratio
  • the polymer compositions allow, for example, the hydrophilicity, hydrophobicity, polarity and/or dielectric constant of the matrix to be set very precisely, which, in combination with the fluorophore concentration range selected, results in measurement independent of ion strength in a certain pH range
  • the response times and conditioning times correspond to the short periods required for optical measurement systems, these parameters being essentially dependent on the membrane thickness
  • a response time of about 10 seconds can be achieved by means of the novel sensors
  • the invention relates to an optical sensor for pH determination independently of the ion strength in the physiological range, comprising
  • the geometrical form of the support material and thus of the sensor can vary greatly, it can be, for example, a fibre, cylinder, sphere, rectangular block or cube
  • Through-flow systems in which continuous measurements or successive measurements can be carried out are also possible
  • Planar sensors are preferred They can have an area of from 0 01 to about 50 cm 2 , advantageously from 0 02 to 10 cm 2
  • the measurement region of the sensor can have an area of less than 5 mm 2 , preferably less than or equal to 2 mm 2
  • the measurement region may be identical with a fully coated surface of the support material Coating of the support material on both sides, but in a locally separated manner, is advantageous
  • the sensor can comprise one or more locally separated membrane layers; in the latter case, parallel measurements with identical or different measurement samples can be carried out
  • the support material is transparent It can be, for example, an inorganic glass, quartz or a transparent thermoplastic or crossimked plastic, such as polycarbonate, polyester, polyamide, polyacrylate or polymethacrylate
  • the dnsocyanates are preferably selected from the group consisting of 1 ,6-b ⁇ s ⁇ socyanato- hexane, 5- ⁇ socyanato-3-( ⁇ socyanatomethyl)-1,1 ,3-t ⁇ methylcyclohexane, 1 ,3-b ⁇ s[5- ⁇ so- cyanato-1 ,3,3-tr ⁇ methylphenyl]-2,4-d ⁇ oxo-1 ,3-d ⁇ azet ⁇ d ⁇ ne, 3,6-b ⁇ s[9- ⁇ socyanatononyl]-4,5-d ⁇ - ( 1 -heptenyl)cyclohexene, b ⁇ s[4- ⁇ socyanatocyclohexyl]methane, trans-1 ,4-b ⁇ s ⁇ socyanato- cyclohexane, 1 ,3-b ⁇ s[ ⁇ socyanatomethyl]benzene, 1 ,3-b ⁇ s[1-
  • the dnsocyanate is particularly preferably b ⁇ s[4- ⁇ socyanatophenyl]methane (4,4'-MDI), 2,4- or 2,6-b ⁇ s ⁇ socyanatotoluene (TDI), 1 ,6-b ⁇ s ⁇ socyanatohexane (HDI), 5- ⁇ socyanato-3- ⁇ so- cyanatomethyl-1 ,1 3-tr ⁇ methylcyclohexane (IPDI) or b ⁇ s[4- ⁇ socyanatocyclohexyl]methane (MDI), or a mixture of these dnsocyanates
  • Examples of C 2 -C 12 alkylenediols are ethylene glycol, 1 ,3-propanediol, 1 ,4-butaned ⁇ ol, 1 ,5-pentaned ⁇ ol, 1 ,6-hexanediol, 1 ,7-heptaned
  • the diol, component d), in the thermoplastic, randomly segmented polyurethane, polyurea or polyurethane-urea is preferably ethylene glycol, butanediol or hexanediol.
  • C 2 -C 12 alkylenediamines are 1 ,2-ethylenediamine, 1,3-d ⁇ aminopropane, 1 ,4-diaminobutane, 1 ,5-diaminopentane, 1 ,6-diaminohexane, 1 ,7-diaminoheptane, 1 ,8-diaminooctane, 1 ,9-diaminononane, 1 ,10-diaminodecane, 1 ,11-diaminoundecane and 1 , 12-diaminododecane.
  • C 3 -C 12 alkylenetriols examples include glycerol, the various positional isomers of butanetriol, pentanetriol, hexanetriol, heptanetriol, octanetriol, nonanetriol, decanetriol, undecanetriol and dodecanetriol.
  • the amino or hydroxyl group of the fluorescein dye f) and the terminal isocyanate component a) are bonded in a urea or urethane group.
  • Component b) in the thermoplastic, randomly segmented polyurethane, polyurea or polyurethane-urea is preferably 70-85 % by weight of polyethylene glycol having a molecular weight of 600-2,000 daltons.
  • Component f) in the thermoplastic, randomly segmented polyurethane, polyurea or polyurethane-urea is preferably 0.1-1 % of a fluorescein dye which is amino- or hydroxyl- functionalized via a bridging group.
  • thermoplastic, randomly segmented polyurethane, polyurea or polyurethane-urea preferably has a molecular weight of from 10,000 to 30,000 daltons.
  • thermoplastic, randomly segmented polyurethane, polyurea or polyurethane-urea preferably includes a fluorescein of the formula (la) or (lb)
  • F ⁇ is a bridging group and is linear or branched C 1 -C 2 oalkylene, C 3 -C 2 oalkenylene, C 3 -C 20 alkynylene or CH 2 -(O-(CHR 2 ) r -CH 2 -CH 2 )n
  • R 2 is C 1 -C 4 alkyl
  • X is OH or NH 2
  • r is 0 or 1
  • n is a number from 1 to 20
  • Another preferred fluorescein is 4-am ⁇ nofluoresce ⁇ n.
  • linear or branched C r C 2 oalkyl radicals are methyl, ethyl, and the various positional isomers of propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, Tndecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and eicosyl
  • linear or branched C 3 -C 20 alkenyl radicals are the various positional isomers of propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, t ⁇ decenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl and eicosenyl.
  • linear or branched C 3 -C 2 oalkynyl radicals are the various positional isomers of propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl, decynyl, undecynyl, dodecynyl, tndecynyl, tetradecynyl, pentadecynyl, hexadecynyl, heptadecynyl, octadecynyl, nonadecynyl and eicosynyl
  • the thickness of the polymer layer B) is preferably from 0.1 to 500 ⁇ m, particularly preferably 1 to 100 ⁇ m
  • These layers can be produced in a manner known per se, for example by dissolving the composition in an organic solvent, then casting the solution to give a film, and finally removing the solvent
  • Suitable solvents are alcohols, ethers, esters, acid amides and ketones Relatively volatile solvents, in particular tetrahydrofuran, are particularly suitable
  • thermoplastic processing Besides these methods in which the composition is firstly dissolved then shaped, and the solvent is then evaporated again, hot shaping processes are also possible, since the composition is a thermoplastic material. Suitable processes are extrusion, injection moulding, compression moulding or blow moulding, as known from thermoplastic processing
  • the layer can be transparent or slightly opaque It is preferably transparent
  • the support materials can be treated in advance with adhesion promoters
  • plasma treatment of the support material in order to generate functional groups on the surface is also possible
  • the surface can also be provided with copolyme ⁇ zable groups in order to achieve particularly high adhesion
  • adhesion promoters for glasses are tnethoxyglycidyloxysilane, 3-az ⁇ dopropylt ⁇ ethoxy- silane and 3-am ⁇ nopropyltr ⁇ ethoxys ⁇ lane
  • the surfaces treated in this way can be modified further, for example by means of 0-(N-succm ⁇ m ⁇ dyl)-6-(4'-az ⁇ do-2'-n ⁇ trophenylam ⁇ no)- hexanoate It has been found particularly advantageous to treat the surfaces with silanes of ethylenically unsaturated carboxylic acid esters, for example 3-t ⁇ methoxys ⁇ lylpropyl methacrylate
  • the polymers can be prepared by methods known per se
  • the reactants can be reacted with one another as such, i e without addition of a solvent or diluent, for example in the melt
  • a solvent or diluent or a mixture of solvents is usually advantageous
  • solvents or diluents which may be mentioned are esters, such as ethyl acetate, ethers, such as diethyl ether, dipropyl ether, dnsopropyl ether, dibutyl ether, tert-butyl methyl ether, tetrahydrofuran or dioxan, ketones, such as acetone, methyl ethyl ketone or methyl isobutyl ketone, amides, such as N,N-d ⁇ - methylformamide, N,N-d ⁇ ethylformam ⁇ de, N,N-d ⁇ methylacetam ⁇ de, N-methylpyrrolidone or hexamethylphospho ⁇ c tnamide,
  • the amine- or hydroxyl-functional fluoresceins of the formula (la) or (lb) covalently bonded to the isocyanate group can be prepared by processes known per se; the starting materials are either commercial products or can be prepared by analogous processes
  • the polymer-bound fluorescem dyes have strong absorption and fluorescence In principle, both properties can be used for pH measurement
  • the invention furthermore relates to a method for the reversible, optical determination of the pH of an aqueous sample independently of the ion strength by the fluorescence method, in which an optical sensor comprising
  • the method can be carried out by, after calibration with samples of known pH, measuring the fluorescence intensity in contact with a measurement solution of unknown composition, and determining the pH for the measured fluorescence intensity directly from the calibration
  • the sensors are brought into contact with the calibration solutions or with the measurement samples This can be done by hand (for example by pipetting) or by means of a suitable automatic through-flow system, with the sensors permanently installed in a flow cell
  • suitable automatic through-flow system with the sensors permanently installed in a flow cell
  • Light sources which can be used for the fluorescence excitation are UV lamps (for example mercury vapour lamps and halogen lamps), lasers, diode lasers and light diodes It may be expedient to use filters to filter out light having the wavelength at which the fluorescent dye has an absorption maximum
  • the fluorescent light emitted by the sensors can be collected, for example using a lens system, and then directed to a detector, for example a secondary electron multiplier or a photodiode
  • the lens system can be arranged in such a way that the fluorescence radiation is measured through the transparent support, over the edges of the support or via the analyte sample
  • the radiation is advantageously directed in a manner known per se via a dichroic mirror
  • the fluorescence from the sensors is preferably measured during contact with the calibration or sample solutions
  • the measurement can be carried out under photostationary conditions with continuous exposure, or, if required, with time resolution This can be achieved, for example, by means of a time-limited laser pulse or by modulation of the intensity of the light source
  • the measurement solution preferably has a pH of from 6 7 to 7.8
  • the measurement solution can include salts of inorganic or organic acids Examples are salts of citric acid, tactic acid, acetic acid, phosphoric acid, hydrochloric acid or sulphuric
  • the ion strength of the measurement solution is preferably from 0 05 to 5 mol/l, particularly preferably from 0 05 to 1 mol/l
  • the ion strength is preferably built up essentially by 1 1 or 1 2 salts
  • Examples of 1 1 salts are LiCI, NaCl, KCI and NH 4 CI
  • Examples of 1 2 salts are CaCI 2 , MgCI 2 and K 2 S0 4 , as desc ⁇ bed, for example, in G Kortum, Lehrbuch der Eiektrochemie [Textbook of Electrochemistry], 4th Edition, Verlag Chemie 1966, page 156
  • the measurement solution preferably comprises or consists of a body fluid It particularly preferably comprises or consists of blood
  • the method can be carried out as an individual measurement or continuously
  • the invention likewise relates to the use of an optical sensor desc ⁇ bed above for optical pH determination of an aqueous measurement solution independently of the ion strength by the fluorescence method
  • Example A3 The compound from Example A3 is dissolved in MeOH, and 2 mol eq. of SnCI 2 H 2 0 are added, whereupon a gas is immediately evolved. The deep-red solution is stirred at RT for 5 hours, and aqueous ammonia is then added, whereupon a red solid precipitates. This is filtered off and dried in a high vacuum, m.p. > 270°C.
  • thermoplastic, randomly segmented polvurethanes which are soluble in organic solvents
  • PTHF polytetrahydrofuran
  • M n 1000 g/mol
  • PEG polyethylene glycol
  • BDO butanediol
  • DABCO diazabicyclooctane
  • Example C1 The procedure is as in Example C1 using the corresponding polymers for Examples B6 and
  • the sensors are installed in a flow cell
  • the calibration or sample solutions are metered in by means of pumps and passed through the cell
  • the measurement arrangement is thermostatted
  • the light from a halogen lamp (white light, excitation wavelength 480 nm) is passed through an excitation filter, reflected at a dichroic mirror and bundled onto the planar sensors by means of lenses
  • the fluorescent light (at 520 nm) emitted by the sensors is collected by the same lens system and passed through an emission filter and the dichroic mirror to a photodiode
  • the fluorescence from the sensors is recorded during exposure by means of the calibration or sample solutions
  • the pH can be determined directly from the measurement value
  • Table 1 shows the pH dependence of the ion strength of the electrolyte in the pH range from 6 7 to 8 0 obtained owing to the different membrane compositions
  • the numerical values relate to the difference in the pK a values measured once at an ion strength of 0 1 mol/l and once at an ion strength of 0 3 mol/l

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Physics & Mathematics (AREA)
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  • General Physics & Mathematics (AREA)
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  • Inorganic Chemistry (AREA)
  • Food Science & Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
PCT/EP1997/003037 1996-06-12 1997-06-11 OPTICAL SENSOR SYSTEM FOR pH DETERMINATION INDEPENDENTLY OF THE ION STRENGTH USING FLUORESCEIN BOUND TO A POLYMER VIA A URETHANE AND/OR UREA GROUP WO1997047966A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
AU31753/97A AU3175397A (en) 1996-06-12 1997-06-11 Optical sensor system for ph determination independently of the ion strength using fluorescein bound to a polymer via urethane and/or urea group
EP97927171A EP0906566A1 (en) 1996-06-12 1997-06-11 OPTICAL SENSOR SYSTEM FOR pH DETERMINATION INDEPENDENTLY OF THE ION STRENGTH USING FLUORESCEIN BOUND TO A POLYMER VIA A URETHANE AND/OR UREA GROUP
JP10501204A JP2000512754A (ja) 1996-06-12 1997-06-11 ウレタンおよび／または尿素基を介してポリマーに結合したフルオレッセインを使用したイオン強度に無関係なｐＨ測定のための光学センサー系

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH147596 1996-06-12
CH1475/96 1996-06-12

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WO1997047966A1 true WO1997047966A1 (en) 1997-12-18

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EP (1) EP0906566A1 (ja)
JP (1) JP2000512754A (ja)
AU (1) AU3175397A (ja)
WO (1) WO1997047966A1 (ja)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10239204B3 (de) * 2002-08-21 2004-06-09 Frank Dipl.-Ing. Zahn Ionenstärke-Sensor
EP1565505A2 (en) * 2002-11-08 2005-08-24 Leatech, LLC Pressure sensitive material
WO2006007209A2 (en) * 2004-06-25 2006-01-19 Leatech, Llc Pressure and temperature sensitive material
ITMO20110327A1 (it) * 2011-12-19 2013-06-20 Rand Srl Una membrana di rilevamento per rilevare parametri di un fluido oragnico durante lo scorrimento in un circuito extracorporeo
DE102019124795A1 (de) * 2019-09-16 2021-03-18 Abberior GmbH Optischer pH-Sensor

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1990000572A1 (en) * 1988-07-11 1990-01-25 Nellcor Incorporated Hydrogel dye film sensing elements and their preparation
WO1994028786A1 (en) * 1993-06-10 1994-12-22 Optical Sensors Incorporated OPTICAL SENSORS FOR MEASURING pH IN FLUIDS
WO1995030148A1 (en) * 1994-05-02 1995-11-09 Ciba-Geigy Ag OPTICAL SENSOR SYSTEM FOR DETERMINING pH VALUES AND IONIC STRENGTHS
WO1997015832A1 (en) * 1995-10-23 1997-05-01 Novartis Ag Optical sensor system for the determination of ph values independently of ionic strength

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1990000572A1 (en) * 1988-07-11 1990-01-25 Nellcor Incorporated Hydrogel dye film sensing elements and their preparation
WO1994028786A1 (en) * 1993-06-10 1994-12-22 Optical Sensors Incorporated OPTICAL SENSORS FOR MEASURING pH IN FLUIDS
WO1995030148A1 (en) * 1994-05-02 1995-11-09 Ciba-Geigy Ag OPTICAL SENSOR SYSTEM FOR DETERMINING pH VALUES AND IONIC STRENGTHS
WO1997015832A1 (en) * 1995-10-23 1997-05-01 Novartis Ag Optical sensor system for the determination of ph values independently of ionic strength

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10239204B3 (de) * 2002-08-21 2004-06-09 Frank Dipl.-Ing. Zahn Ionenstärke-Sensor
EP1565505A2 (en) * 2002-11-08 2005-08-24 Leatech, LLC Pressure sensitive material
US7176272B2 (en) * 2002-11-08 2007-02-13 Leatech, Llc Pressure sensitive material
EP1565505A4 (en) * 2002-11-08 2008-04-09 Leatech Llc PRESSURE-SENSITIVE MATERIAL
WO2006007209A2 (en) * 2004-06-25 2006-01-19 Leatech, Llc Pressure and temperature sensitive material
WO2006007209A3 (en) * 2004-06-25 2008-12-04 Leatech Llc Pressure and temperature sensitive material
ITMO20110327A1 (it) * 2011-12-19 2013-06-20 Rand Srl Una membrana di rilevamento per rilevare parametri di un fluido oragnico durante lo scorrimento in un circuito extracorporeo
WO2013093792A1 (en) * 2011-12-19 2013-06-27 Rand S.R.L. A sensing membrane for sensing parameters of an organic fluid during its flowing in an extracorporeal circuit
DE102019124795A1 (de) * 2019-09-16 2021-03-18 Abberior GmbH Optischer pH-Sensor

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EP0906566A1 (en) 1999-04-07
JP2000512754A (ja) 2000-09-26
AU3175397A (en) 1998-01-07

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