JP2011519420A5 - - Google Patents
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- JP2011519420A5 JP2011519420A5 JP2011504410A JP2011504410A JP2011519420A5 JP 2011519420 A5 JP2011519420 A5 JP 2011519420A5 JP 2011504410 A JP2011504410 A JP 2011504410A JP 2011504410 A JP2011504410 A JP 2011504410A JP 2011519420 A5 JP2011519420 A5 JP 2011519420A5
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- Japan
- Prior art keywords
- time
- spiropyran
- temperature indicator
- acid
- indicator according
- Prior art date
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- KGEKLUUHTZCSIP-HOSYDEDBSA-N [(1S,4S,6R)-1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl] acetate Chemical compound C1C[C@]2(C)[C@H](OC(=O)C)C[C@H]1C2(C)C KGEKLUUHTZCSIP-HOSYDEDBSA-N 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 4
- -1 citrate ester Chemical class 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 239000007787 solid Substances 0.000 claims 3
- HVYWMOMLDIMFJA-DPAQBDIFSA-N (3β)-Cholest-5-en-3-ol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 2
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 claims 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N Cetyl alcohol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N Imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N Methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 claims 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N Oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N Sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N Stearic acid Chemical group CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 238000004061 bleaching Methods 0.000 claims 2
- 229940115397 bornyl acetate Drugs 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 238000002845 discoloration Methods 0.000 claims 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine group Chemical group N1=CCC2=CC=CC=C12 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 2
- 229930007650 limonene Natural products 0.000 claims 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims 2
- 229920000570 polyether Polymers 0.000 claims 2
- 230000001012 protector Effects 0.000 claims 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 2
- ULDHMXUKGWMISQ-VIFPVBQESA-N (+)-(4S)-carvone Chemical compound CC(=C)[C@H]1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-VIFPVBQESA-N 0.000 claims 1
- XMGQYMWWDOXHJM-UHFFFAOYSA-N (+-)-(RS)-limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims 1
- ACAKHSFNARGOES-UHFFFAOYSA-N 4,7,7-trimethylbicyclo[2.2.1]heptan-3-ol Chemical compound C1CC2(C)C(O)CC1C2(C)C.C1CC2(C)C(O)CC1C2(C)C ACAKHSFNARGOES-UHFFFAOYSA-N 0.000 claims 1
- ZRSNZINYAWTAHE-UHFFFAOYSA-N 4-Anisaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 claims 1
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 claims 1
- RSWGJHLUYNHPMX-ONCXSQPRSA-N Abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 claims 1
- RSWGJHLUYNHPMX-HNBVOPMISA-N Abietic acid Natural products C([C@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-HNBVOPMISA-N 0.000 claims 1
- QFOHBWFCKVYLES-UHFFFAOYSA-N Butylparaben Chemical compound CCCCOC(=O)C1=CC=C(O)C=C1 QFOHBWFCKVYLES-UHFFFAOYSA-N 0.000 claims 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L Calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 claims 1
- 239000005973 Carvone Substances 0.000 claims 1
- 229940107161 Cholesterol Drugs 0.000 claims 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N Guaiacol Chemical group COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims 1
- OSWPMRLSEDHDFF-UHFFFAOYSA-N Methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 claims 1
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 claims 1
- NJTGANWAUPEOAX-UHFFFAOYSA-N MolPort-023-220-454 Chemical compound OCC(O)CO.OCC(O)CO NJTGANWAUPEOAX-UHFFFAOYSA-N 0.000 claims 1
- 235000021360 Myristic acid Nutrition 0.000 claims 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 claims 1
- 239000005642 Oleic acid Substances 0.000 claims 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 1
- 239000004698 Polyethylene (PE) Substances 0.000 claims 1
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- 239000004721 Polyphenylene oxide Substances 0.000 claims 1
- 229920001451 Polypropylene glycol Polymers 0.000 claims 1
- 235000021355 Stearic acid Nutrition 0.000 claims 1
- GLDOVTGHNKAZLK-UHFFFAOYSA-N Stearyl alcohol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims 1
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 claims 1
- NWGKJDSIEKMTRX-HSACVWGTSA-N [(2R)-2-[(2R,3R,4S)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] (E)-octadec-9-enoate Chemical compound CCCCCCCC\C=C\CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-HSACVWGTSA-N 0.000 claims 1
- LWZFANDGMFTDAV-BURFUSLBSA-N [(2R)-2-[(2R,3R,4S)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O LWZFANDGMFTDAV-BURFUSLBSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 230000004913 activation Effects 0.000 claims 1
- 230000032683 aging Effects 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 125000005233 alkylalcohol group Chemical group 0.000 claims 1
- NDKYEUQMPZIGFN-UHFFFAOYSA-N butyl dodecanoate Chemical group CCCCCCCCCCCC(=O)OCCCC NDKYEUQMPZIGFN-UHFFFAOYSA-N 0.000 claims 1
- 229940067596 butylparaben Drugs 0.000 claims 1
- 239000008116 calcium stearate Substances 0.000 claims 1
- 235000013539 calcium stearate Nutrition 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 229930007075 carvone Natural products 0.000 claims 1
- 229960000541 cetyl alcohol Drugs 0.000 claims 1
- 235000012000 cholesterol Nutrition 0.000 claims 1
- RJECHNNFRHZQKU-RMUVNZEASA-N cholesteryl oleate Chemical compound C([C@@H]12)C[C@]3(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)C1 RJECHNNFRHZQKU-RMUVNZEASA-N 0.000 claims 1
- 238000004040 coloring Methods 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 150000003997 cyclic ketones Chemical class 0.000 claims 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 claims 1
- 150000002009 diols Chemical class 0.000 claims 1
- 239000000194 fatty acid Substances 0.000 claims 1
- 150000004665 fatty acids Chemical class 0.000 claims 1
- 229940087305 limonene Drugs 0.000 claims 1
- 235000001510 limonene Nutrition 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 235000019359 magnesium stearate Nutrition 0.000 claims 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 claims 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 claims 1
- 229960002216 methylparaben Drugs 0.000 claims 1
- 239000003607 modifier Substances 0.000 claims 1
- 229920001610 polycaprolactone Polymers 0.000 claims 1
- 239000004632 polycaprolactone Substances 0.000 claims 1
- 229920000573 polyethylene Polymers 0.000 claims 1
- 229920001223 polyethylene glycol Polymers 0.000 claims 1
- 229920000151 polyglycol Polymers 0.000 claims 1
- 239000010695 polyglycol Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 229940035044 sorbitan monolaurate Drugs 0.000 claims 1
- 239000001593 sorbitan monooleate Substances 0.000 claims 1
- 235000011069 sorbitan monooleate Nutrition 0.000 claims 1
- 229940035049 sorbitan monooleate Drugs 0.000 claims 1
- 239000000600 sorbitol Substances 0.000 claims 1
- 239000008117 stearic acid Substances 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
Claims (13)
CH3−(CH2)n−COOC1〜C18アルキル(n=10〜18)、オレイン酸コレステロール、クエン酸エステル、p−ヒドロキシベンゾエート、酢酸ボルニルから選択されるエステル、またはジカルボン酸C1〜C18アルキル−O−OC−(CH2)m−COOC1〜C18アルキル(m=2〜20)から選択されるエステル、または糖アルコールから選択されるエステルから選択されるか;あるいは前記調整剤は、
C6−C20アルキルアルコールから選択されるか、または
環状アルコールから選択されるか、または
ポリアルコールから選択されるか、または
ポリエーテルから選択されるか、または
脂肪酸から選択されるか、または
カルボン酸の塩から選択されるか、または
ジテルペン酸から選択されるか、または
尿素もしくはイミダゾールかから選択されるか、または
環状ケトンから選択されるか、または
2,6−ジ−t−ブチル−4−メトキシフェノールもしくは4−ヒドロキシ−3−メトキシベンズアルデヒドから選択されるか、または
クロマン−6−オールから選択されるか、または
4−イソプロペニル−1−メチルシクロヘキセン(R−リモネン)から選択されるか、または
ナフタレン、フェナントレンから選択されるか、または
ドデシル硫酸ナトリウムから選択されるか、または
ヒドロキシナフトエ酸のZn錯体から選択されるか、または
第2インドレニン単位のスピロピランに対する付加物から選択されるか、または
2つの異なるスピロピランの混合固体から選択される、時間・温度指示薬。 A time-temperature indicator, wherein the indicator is formed of a protector that prevents new photo-induced coloration of the indicator, spiropyran, and a spiropyran mixed solid having an amorphous, crystalline or mixed amorphous-crystalline structure A regulator that can be used,
CH 3 — (CH 2 ) n —COOC 1 -C 18 alkyl (n = 10-18), cholesterol oleate, citrate ester, p-hydroxybenzoate, ester selected from bornyl acetate, or dicarboxylic acid C 1- C 18 alkyl -O-OC- (CH 2) m -COOC 1 ~C 18 alkyl ester selected from (m = 2 to 20) or is selected from esters selected from sugar alcohols; or the adjustment The agent
Selected from C 6 -C 20 alkyl alcohols, selected from cyclic alcohols, selected from polyalcohols, selected from polyethers, selected from fatty acids, or carvone Selected from salts of acids, selected from diterpenic acid, selected from urea or imidazole, or selected from cyclic ketones, or 2,6-di-t-butyl-4 - it is selected from methoxy phenol or 4-hydroxy-3 is selected from methoxy benzaldehyde, or chroman-6-O-or-le or we selected, or 4-isopropenyl-1-methyl-cyclohexene (R- limonene) Or selected from naphthalene, phenanthrene, or sodium dodecyl sulfate Selected from lithium, selected from Zn complexes of hydroxynaphthoic acid, selected from adducts of second indolenine units to spiropyran, or selected from mixed solids of two different spiropyrans, Time / temperature indicator.
a)スピロピランとナフタレン、
b)スピロピランとセチルアルコール、
c)スピロピランとドデシル硫酸ナトリウム、
d)スピロピランとヒドロキシナフトエ酸のZn錯体、
e)スピロピランと第2インドレニン単位のスピロピランへの付加物、
f)2つの異なるスピロピラン
から選択される混合固体を含む、請求項1記載の時間・温度指示薬。 Less than,
a) Spiropyran and naphthalene,
b) spiropyran and cetyl alcohol,
c) Spiropyran and sodium dodecyl sulfate,
d) Zn complex of spiropyran and hydroxynaphthoic acid,
e) adducts of spiropyran and second indolenine units to spiropyran,
2. The time / temperature indicator of claim 1 comprising a mixed solid selected from two different spiropyrans.
a)スピロピランおよび調整剤を含む請求項1から10までのいずれか1項に記載の時間・温度指示薬を基材上に印刷する工程、
b)UV光での照射による前記指示薬の活性化、特に光誘起着色をする工程、
c)前記指示薬の新たな光誘起着色を防止するプロテクターを適用する工程、および
d)時間もしくは温度誘起変色の程度、および変色の程度を考慮して製品の品質を決定する工程を含む、方法。 A method for determining the quality of an aging sensitive and temperature sensitive product comprising the following steps:
a) printing the time / temperature indicator according to any one of claims 1 to 10 on a substrate, comprising spiropyran and a regulator;
b) activation of the indicator by irradiation with UV light, in particular photo-induced coloring,
c) applying a protector that prevents new light-induced coloration of the indicator; and d) determining the quality of the product taking into account the degree of time or temperature-induced discoloration and the degree of discoloration.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP08154635.0 | 2008-04-16 | ||
EP08154635 | 2008-04-16 | ||
PCT/EP2009/053948 WO2009127529A1 (en) | 2008-04-16 | 2009-04-02 | Optimized time temperature indicator |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2011519420A JP2011519420A (en) | 2011-07-07 |
JP2011519420A5 true JP2011519420A5 (en) | 2012-01-19 |
JP5453393B2 JP5453393B2 (en) | 2014-03-26 |
Family
ID=39717538
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2011504410A Expired - Fee Related JP5453393B2 (en) | 2008-04-16 | 2009-04-02 | Optimized time / temperature indicator |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP2269056A1 (en) |
JP (1) | JP5453393B2 (en) |
CN (1) | CN102007404A (en) |
IL (1) | IL208160A0 (en) |
WO (1) | WO2009127529A1 (en) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20110139059A1 (en) * | 2008-05-21 | 2011-06-16 | Basf Se | Time temperature indicator comprising indolenin based spiropyrans containing a n-acetylamido or n-acetylester side chain |
ES2376559B1 (en) | 2011-04-11 | 2013-01-24 | Universidad Pública de Navarra | DEVICE FOR MONITORING TIME AND TEMPERATURE CONDITIONS. |
NO20110589A1 (en) | 2011-04-15 | 2012-05-21 | Keep It Tech As | Time-temperature indicator system |
NO20110590A1 (en) | 2011-04-15 | 2012-04-02 | Keep It Tech As | Time-temperature indicator system, method of its manufacture and combination comprising said time-temperature indicator system. |
CN105891410A (en) * | 2016-04-14 | 2016-08-24 | 梧州市产品质量检验所 | Detection method of abietic acid in rosin |
CN106568528B (en) * | 2016-10-31 | 2019-12-27 | 深圳九星印刷包装集团有限公司 | Water loss sensitive time indicator |
DE102017003171A1 (en) * | 2017-03-31 | 2018-10-04 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | TIEFTEMPERATUR-INDIKATORMISCHUNG, DEVICE AND METHOD FOR MONITORING A TEMPERATURE TRANSITION AT DEEP TEMPERATURES |
CN110375878A (en) * | 2019-06-14 | 2019-10-25 | 中国科学院大学 | A kind of irreversible thermochromism indicator solution, the temperature monitor containing it and application |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0796678B2 (en) * | 1989-05-22 | 1995-10-18 | サカタインクス株式会社 | Shading material |
JP2962035B2 (en) * | 1992-04-03 | 1999-10-12 | 松下電器産業株式会社 | Photochromic composition and optical recording medium using the same |
JP3505401B2 (en) * | 1998-09-16 | 2004-03-08 | 株式会社東芝 | Method for preparing erasable image forming material |
EP1711809A2 (en) * | 2004-02-02 | 2006-10-18 | Freshpoint Holdings Sa | Time-temperature indicator based on valence isomerizations |
US8076058B2 (en) * | 2004-09-30 | 2011-12-13 | Hewlett-Packard Development Company, L.P. | Color forming compositions and associated methods |
US7538070B2 (en) * | 2005-06-07 | 2009-05-26 | Xerox Corporation | Thermochromic recording medium |
-
2009
- 2009-04-02 JP JP2011504410A patent/JP5453393B2/en not_active Expired - Fee Related
- 2009-04-02 WO PCT/EP2009/053948 patent/WO2009127529A1/en active Application Filing
- 2009-04-02 CN CN2009801134829A patent/CN102007404A/en active Pending
- 2009-04-02 EP EP09732219A patent/EP2269056A1/en not_active Withdrawn
-
2010
- 2010-09-15 IL IL208160A patent/IL208160A0/en unknown
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