WO1987003367A1 - Integrateur temps-temperature a base leuco photoactivable - Google Patents
Integrateur temps-temperature a base leuco photoactivable Download PDFInfo
- Publication number
- WO1987003367A1 WO1987003367A1 PCT/US1986/002301 US8602301W WO8703367A1 WO 1987003367 A1 WO1987003367 A1 WO 1987003367A1 US 8602301 W US8602301 W US 8602301W WO 8703367 A1 WO8703367 A1 WO 8703367A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- indicator
- temperature
- leuco
- time
- reflectivity
- Prior art date
Links
- 239000000203 mixture Substances 0.000 claims abstract description 29
- 239000002253 acid Substances 0.000 claims abstract description 10
- 238000002310 reflectometry Methods 0.000 claims description 20
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 15
- 230000008859 change Effects 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- 229920002689 polyvinyl acetate Polymers 0.000 claims description 11
- 239000011118 polyvinyl acetate Substances 0.000 claims description 11
- FDZZZRQASAIRJF-UHFFFAOYSA-M malachite green Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 FDZZZRQASAIRJF-UHFFFAOYSA-M 0.000 claims description 9
- 229940107698 malachite green Drugs 0.000 claims description 9
- 230000005855 radiation Effects 0.000 claims description 9
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 8
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 5
- YFDSDPIBEUFTMI-UHFFFAOYSA-N tribromoethanol Chemical compound OCC(Br)(Br)Br YFDSDPIBEUFTMI-UHFFFAOYSA-N 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 2
- 239000001003 triarylmethane dye Substances 0.000 claims description 2
- 230000004913 activation Effects 0.000 abstract description 15
- 239000000463 material Substances 0.000 abstract description 7
- 238000012544 monitoring process Methods 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000011159 matrix material Substances 0.000 abstract 1
- 230000001443 photoexcitation Effects 0.000 abstract 1
- 230000000750 progressive effect Effects 0.000 abstract 1
- 230000002186 photoactivation Effects 0.000 description 19
- 238000000576 coating method Methods 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000011248 coating agent Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- 239000000975 dye Substances 0.000 description 8
- 239000000499 gel Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000008569 process Effects 0.000 description 5
- 238000005057 refrigeration Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- ZGKDNJHGCZXEGY-UHFFFAOYSA-N 2-nitrosobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1N=O ZGKDNJHGCZXEGY-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical group OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052785 arsenic Inorganic materials 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 150000001559 benzoic acids Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920006267 polyester film Polymers 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- GESUXCLRERRNSQ-UHFFFAOYSA-N 1-benzhydrylnaphthalene Chemical compound C1=CC=CC=C1C(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 GESUXCLRERRNSQ-UHFFFAOYSA-N 0.000 description 1
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- 0 CC(*C(*)*1)*C1I Chemical compound CC(*C(*)*1)*C1I 0.000 description 1
- 206010073306 Exposure to radiation Diseases 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- -1 NfC^-C^al yl Chemical class 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 229960001506 brilliant green Drugs 0.000 description 1
- HXCILVUBKWANLN-UHFFFAOYSA-N brilliant green cation Chemical compound C1=CC(N(CC)CC)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](CC)CC)C=C1 HXCILVUBKWANLN-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000979 synthetic dye Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01K—MEASURING TEMPERATURE; MEASURING QUANTITY OF HEAT; THERMALLY-SENSITIVE ELEMENTS NOT OTHERWISE PROVIDED FOR
- G01K3/00—Thermometers giving results other than momentary value of temperature
- G01K3/02—Thermometers giving results other than momentary value of temperature giving means values; giving integrated values
- G01K3/04—Thermometers giving results other than momentary value of temperature giving means values; giving integrated values in respect of time
-
- 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
- G01N31/229—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 time/temperature history
Definitions
- This invention relates to a time-temperature indicator and, more particularly, to an indicator that is inactive until it is activated by actinic radiation.
- U.S. Patent 3,768,976, issued October 30, 1973, to Hu et al. has disclosed a temperature-time integrating indicator that is based on temperature-dependent oxygen diffusion into a package that includes an aqueous solution of a redox dye. The dye is dark in the reduced state and becomes colorless when it is oxidized.
- a photo- activatable time-temperature indicator comprises a mix ⁇ ture of:
- the mixture is dispersed in a medium and coated, onto a substrate.
- the present invention provides a method of measuring an incremental time-temperature exposure, which comprises the steps:
- time-temperature indicator refers to a composition that responds in a measurable and predic ⁇ table way to the integrated effect of time and tempera ⁇ ture.
- the activation of the time-temperature indicators of this invention is by photogeneration of an "acid,”
- Figure 1 depicts the time dependence of reflectivity at 632 nm of an activated indicator label
- Fig. 2 depicts the time dependence of the rate of change of reflectivity on indicator coating thickness and photoactivation.
- a time-temperature indicator is a useful tool for those who are concerned with the freshness of perishable products.
- the indicator must comprise a composition
- Some disadvantages or concerns include ,- (i) possibility of activation by ambient light exposure,
- a suitable time-temperature indicator can be based on color development of a leuco base.
- Leuco bases are the colorless (i.e., white) forms, and can be considered to be the precursors, of dyes such as diphenylmethane _ and triarylmethane dyes. (Detailed information concerning these dyes - preparation, properties, etc. - appears in K. Venkataraman, The Chemistry of Synthetic Dyes, Vol. II, Academic Press, N.Y., 1952, pp 705 ff.)
- triarylmethane leuco 0 bases (I) are generally preferred:
- Each R is independently H, (C 1 -C 2 )alkyl, hydroxyalkyl, sulfonated alkyl, or a substituted phenyl group.
- Each R' is independently H,C 1 -alkyl, or a sulfite group.
- Each R" is independently H or C ⁇ -alkyl.
- 1-R5 are independently H,(C 1 -C 4 )alkyl, halogen, amine, NfC ⁇ -C ⁇ al yl, carboxylic acid, sulfite, hydroxyl, or a substituted phenyl group.
- Ar may also be replaced by naphthalene or substituted naphthalenes, in which case the leuco base is a diphenylnaphthylmethane leuco.
- a He-Ne laser which emits at 632 run, is a convenient light source for monitoring the reflectivity of the indicators of the present invention.
- the preferred leuco bases are those that provide final colors green, blue, or violet. Speci ⁇ fically, malachite green leuco (II), brilliant green leuco (III), and crystal violet leuco (IV) are particularly preferred.
- HY is an acid.
- the rate at which color develops depends on the temperature; i.e., the color development is an indication of time-temperature exposure.
- the photoactivation process generates a carbinol or carbinol equivalent that then reacts with the photoacid to start the development of color.
- the dye being formed by the (time-temperature dependent) action of photoacid on the leuco base.
- a number of chemical compounds are known to gene ⁇ rate acids upon excitation with actinic radiation.
- photoacids are o-nitrobenzaldehydes and substituted o-nitrobenzaldehydes; trihaloalcohols (X 3 ROH, where X is a halogen and R is an alkyl having at least 2 carbon atoms) ; and compounds of the form ⁇ n (I,S) (P,Sb,As)F m , where n is 2 or 3 and m is 4 for P and 6 for Sb or As.
- X 3 ROH trihaloalcohols
- the photoacid generator either not respond to ambient light exposure or that the indicator be protected from such exposure (e.g., by incorporating an opaque cover sheet or by keeping the indicator in the dark).
- the photoactivation step must be reproducible. That can be accomplished conveniently and easily by, for example, using a reproducible light source or monitoring the photoactivation exposure.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Measuring Temperature Or Quantity Of Heat (AREA)
- Investigating Or Analyzing Materials Using Thermal Means (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Photometry And Measurement Of Optical Pulse Characteristics (AREA)
Abstract
Un indicateur intégrateur de temps-température photoactivé se fonde sur un système à base leuco. Une base leuco blanche (''inactive'') insensible à la chaleur (ou un mélange de base leuco de ce type) est mélangée, de préférence dans une matrice polymère, à une substance produisant un acide lorsqu'elle est exposée à la lumière. La photoexcitation, de préférence par lumière ultraviolette ou une longueur d'ondes proche de l'ultraviolet, provoque la formation d'un produit chromogène (''actif'') sensible à la chaleur. A la suite de cette étape d'activation, un développement progressif de couleur se produit à une cadence augmentant avec la température. L'indicateur est utile pour contrôler la fraîcheur de denrées périssables, notamment celles stockées à une température inférieure à la température ambiante.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80375085A | 1985-12-02 | 1985-12-02 | |
| US803,750 | 1985-12-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1987003367A1 true WO1987003367A1 (fr) | 1987-06-04 |
Family
ID=25187342
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1986/002301 WO1987003367A1 (fr) | 1985-12-02 | 1986-10-28 | Integrateur temps-temperature a base leuco photoactivable |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JP2557362B2 (fr) |
| WO (1) | WO1987003367A1 (fr) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2260813A (en) * | 1991-10-26 | 1993-04-28 | Raymond * Williams Terry | Cryogenic labels to detect an exposure to sub zero temperatures for a predetermined period of time |
| WO1994012858A1 (fr) * | 1990-03-16 | 1994-06-09 | Jp Laboratories, Inc. | Semiconducteur utilise dans le controle de valeurs integrales de temps et de temperature de stockage de produits perissables |
| WO2006021953A2 (fr) | 2004-08-24 | 2006-03-02 | Skyrad Ltd. | Dispositif indiquant des produits sensibles a la temperature |
| US7294379B2 (en) | 2002-03-07 | 2007-11-13 | Avery Dennison Corporation | Color changing device for time indicating label and methods of making and using the same |
| US11398167B2 (en) | 2016-07-11 | 2022-07-26 | Intray Ltd. | Time temperature indicator label |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR66066E (fr) * | 1956-05-03 | |||
| GB880859A (en) * | 1959-06-25 | 1961-10-25 | Ncr Co | Method for indicating temperature variations in a refrigerating apparatus |
| EP0117390A2 (fr) * | 1983-02-25 | 1984-09-05 | Lifelines Technology, Inc. | Procédé de surveillance de l'exposé incrémental à l'environnement des produits, subissant des changements de qualité progressifs suite aux stimulations extérieures |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3445232A (en) * | 1965-10-21 | 1969-05-20 | Horizons Research Inc | Photography |
-
1986
- 1986-10-28 JP JP61506173A patent/JP2557362B2/ja not_active Expired - Fee Related
- 1986-10-28 WO PCT/US1986/002301 patent/WO1987003367A1/fr unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR66066E (fr) * | 1956-05-03 | |||
| GB880859A (en) * | 1959-06-25 | 1961-10-25 | Ncr Co | Method for indicating temperature variations in a refrigerating apparatus |
| EP0117390A2 (fr) * | 1983-02-25 | 1984-09-05 | Lifelines Technology, Inc. | Procédé de surveillance de l'exposé incrémental à l'environnement des produits, subissant des changements de qualité progressifs suite aux stimulations extérieures |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994012858A1 (fr) * | 1990-03-16 | 1994-06-09 | Jp Laboratories, Inc. | Semiconducteur utilise dans le controle de valeurs integrales de temps et de temperature de stockage de produits perissables |
| GB2260813A (en) * | 1991-10-26 | 1993-04-28 | Raymond * Williams Terry | Cryogenic labels to detect an exposure to sub zero temperatures for a predetermined period of time |
| US7294379B2 (en) | 2002-03-07 | 2007-11-13 | Avery Dennison Corporation | Color changing device for time indicating label and methods of making and using the same |
| WO2006021953A2 (fr) | 2004-08-24 | 2006-03-02 | Skyrad Ltd. | Dispositif indiquant des produits sensibles a la temperature |
| US8183045B2 (en) | 2004-08-24 | 2012-05-22 | Skyrad, Ltd. | Indicating device for temperature sensitive products |
| US11398167B2 (en) | 2016-07-11 | 2022-07-26 | Intray Ltd. | Time temperature indicator label |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2557362B2 (ja) | 1996-11-27 |
| JPS63502772A (ja) | 1988-10-13 |
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