EP1889049A2 - Thermochrome und thermofluoreszierende pigmente: intensivierung von farbe und fluoreszenz mit zusätzen - Google Patents
Thermochrome und thermofluoreszierende pigmente: intensivierung von farbe und fluoreszenz mit zusätzenInfo
- Publication number
- EP1889049A2 EP1889049A2 EP06770799A EP06770799A EP1889049A2 EP 1889049 A2 EP1889049 A2 EP 1889049A2 EP 06770799 A EP06770799 A EP 06770799A EP 06770799 A EP06770799 A EP 06770799A EP 1889049 A2 EP1889049 A2 EP 1889049A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- substituted
- unsubstituted
- radical
- thermochromic
- temperature
- 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- Withdrawn
Links
- 239000000654 additive Substances 0.000 title claims abstract description 18
- 239000000049 pigment Substances 0.000 title claims description 9
- 230000002708 enhancing effect Effects 0.000 title description 2
- -1 alkyl radical Chemical class 0.000 claims abstract description 105
- 230000007704 transition Effects 0.000 claims abstract description 46
- 239000000463 material Substances 0.000 claims abstract description 24
- 150000003384 small molecules Chemical class 0.000 claims abstract description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000005840 aryl radicals Chemical class 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 230000000996 additive effect Effects 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims abstract description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims abstract description 8
- 230000008859 change Effects 0.000 claims abstract description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims abstract description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 4
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229930192474 thiophene Natural products 0.000 claims abstract description 4
- 239000004305 biphenyl Substances 0.000 claims abstract description 3
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 3
- 230000002441 reversible effect Effects 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract 6
- 238000001816 cooling Methods 0.000 claims abstract 2
- 230000002427 irreversible effect Effects 0.000 claims abstract 2
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 6
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 229920002635 polyurethane Polymers 0.000 claims description 5
- 239000004814 polyurethane Substances 0.000 claims description 5
- 239000004952 Polyamide Substances 0.000 claims description 4
- 239000004698 Polyethylene Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 4
- 239000003921 oil Substances 0.000 claims description 4
- 229920002647 polyamide Polymers 0.000 claims description 4
- 229920000573 polyethylene Polymers 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- 239000004642 Polyimide Substances 0.000 claims description 3
- 150000001720 carbohydrates Chemical class 0.000 claims description 3
- 235000014633 carbohydrates Nutrition 0.000 claims description 3
- 229920001903 high density polyethylene Polymers 0.000 claims description 3
- 239000004700 high-density polyethylene Substances 0.000 claims description 3
- 229920001684 low density polyethylene Polymers 0.000 claims description 3
- 239000004702 low-density polyethylene Substances 0.000 claims description 3
- 229920000058 polyacrylate Polymers 0.000 claims description 3
- 229920000515 polycarbonate Polymers 0.000 claims description 3
- 239000004417 polycarbonate Substances 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 229920001721 polyimide Polymers 0.000 claims description 3
- 229920000098 polyolefin Polymers 0.000 claims description 3
- 229920001296 polysiloxane Polymers 0.000 claims description 3
- 229920001290 polyvinyl ester Polymers 0.000 claims description 3
- 229920001289 polyvinyl ether Polymers 0.000 claims description 3
- 229920001291 polyvinyl halide Polymers 0.000 claims description 3
- 229920005989 resin Polymers 0.000 claims description 3
- 239000011347 resin Substances 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 239000004743 Polypropylene Substances 0.000 claims description 2
- 229920002125 Sokalan® Polymers 0.000 claims description 2
- 229920001971 elastomer Polymers 0.000 claims description 2
- 239000000806 elastomer Substances 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 229920002492 poly(sulfone) Polymers 0.000 claims description 2
- 229920002401 polyacrylamide Polymers 0.000 claims description 2
- 229920001155 polypropylene Polymers 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000004001 thioalkyl group Chemical group 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 28
- 239000002131 composite material Substances 0.000 description 12
- 239000000178 monomer Substances 0.000 description 12
- 229920000123 polythiophene Polymers 0.000 description 12
- ARFJPHXJBIEWSZ-UHFFFAOYSA-N 3-octadecylthiophene Chemical compound CCCCCCCCCCCCCCCCCCC=1C=CSC=1 ARFJPHXJBIEWSZ-UHFFFAOYSA-N 0.000 description 11
- 239000000976 ink Substances 0.000 description 9
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- WSVDSBZMYJJMSB-UHFFFAOYSA-N octadecylbenzene Chemical compound CCCCCCCCCCCCCCCCCCC1=CC=CC=C1 WSVDSBZMYJJMSB-UHFFFAOYSA-N 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 235000013361 beverage Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 229940093476 ethylene glycol Drugs 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- ASWOZWYFBVLCMR-UHFFFAOYSA-N 1,4-dihexoxybenzene Chemical compound CCCCCCOC1=CC=C(OCCCCCC)C=C1 ASWOZWYFBVLCMR-UHFFFAOYSA-N 0.000 description 1
- WSULSMOGMLRGKU-UHFFFAOYSA-N 1-bromooctadecane Chemical compound CCCCCCCCCCCCCCCCCCBr WSULSMOGMLRGKU-UHFFFAOYSA-N 0.000 description 1
- BPNQMPWZDNUCPT-UHFFFAOYSA-N 2-octadecylthiophene Chemical compound CCCCCCCCCCCCCCCCCCC1=CC=CS1 BPNQMPWZDNUCPT-UHFFFAOYSA-N 0.000 description 1
- 229920003332 Epotuf® Polymers 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 229920006063 Lamide® Polymers 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
Definitions
- thermochromic indicator materials comprised of polythiophenes.
- Polythiophenes are known for their electrically conductive properties.
- One technique used to study polythiophenes is to analyze associated color changes when the temperature of the polythiophene is varied. Color changes provide insight into the electro-conductive properties of the polymer.
- the useful life of many products can become compromised if exposed to temperatures above a pre-determined temperature.
- Controlling the predetermined temperature, raising or lowering, is important for wide applicability for various applications.
- the present invention addresses this need.
- the invention comprises a temperature sensitive polymer that visually changes color at a proscribed temperature within the range of between about -30 to 150 0 C.
- the temperature of the color change (hereinafter referred to as the thermochromic transition) can be adjusted by synthetically modifying the thermochromic polymer.
- the thermochromic transition temperature can be further modified via the incorporation of various small molecule additives including the monomer from which the polymer was prepared and structurally related compounds.
- the thermochromic polymer/small molecule additive composites can be dispersed in commercial plastics (polyurethane, polystyrene, polyethylene, etc.) at low concentrations and retain the controlled reversibility.
- the temperature sensitive polymer /additive composites can also be used as a pigment for inks.
- the thermochromic polymers are generally of the structure:
- Ri-R ⁇ a hydrogen, substituted or unsubstituted alkyl radical, substituted or unsubstituted alkoxy radical, substituted or unsubstituted aryl radical, substituted or unsubstituted thioalkyl radical, substituted or unsubstituted trialkylsilyl radical, substituted or unsubstituted acyl radical, substituted or unsubstituted ester radical, substituted or unsubstituted amine radical, substituted or unsubstituted amide radical, substituted or unsubstituted heteroaryl or substituted or unsubstituted aryl radical
- n is between 1 and 1000
- m is between 0 and 1000
- 1 is between 1 and 1000.
- the invention is directed to a method of adding monomer, or other small molecules, to substituted polythiophenes to modify or enhance the thermochromic and thermoflourescent properties of the materials allowing one to determine the genuineness of an article.
- the monomer, or other small molecule comprised of a compound having the following structures: R-Ar-R' , R-X, or linear alkane
- X a halogen (F, Cl, Br, or I).
- thermochromic/thermoflourescent transition temperature centered at 65 0 C is light red/orange in color below the thermochromic/thermoflourescent transition temperature with very weak fluorescence and a bright yellow color with a strong emission of yellow/orange light.
- Addition of octadecylthiophene lowers the transition temperature to 52 0 C, darkens the low temperature color to red/purple but does not significantly alter the low temperature fluorescence. Upon heating the composite changes color to yellow with a very strong yellow/orange emission.
- Fig. 1 are plots of Polymer A DSC versus heat flow:
- Fig. 2 are photographs of poly(3-(oligoethylene oxide)-4-methylthiophene with Poly(ethyleneglycol) dimethyl ether.
- thermochromic transitions For regiorandom polymers longer substituents such as n- hexadecyl have lower temperature thermochromic transitions (81 0 C) than shorter chain substituents such as n-octyl (130 0 C).
- the regioregular polymers have higher thermochromic transitions than the regiorandom polymers but the same inverse correlation with chainlength is observed.
- the n-hexadecyl and n-octyl have thermochromic transition centered around 125 and 175 0 C.
- the thermochromic transition temperatures are dependent upon the molecular weight of the polymer. Lower molecular weight polymers have lower thermochromic transition temperatures while higher molecular weight polymers have higher thermochromic transition temperatures.
- thermochromic transition and the color of the thermochromic material can be further modified by the incorporation of various small molecule additives.
- the best small molecule additives are structurally related to the monomer, such as 3-alkylthiophene, from which the polymer was prepared.
- the invention includes the use of polythiophene/small molecule additive composite as a neat mixture or admixed with paints including polyurethanes, polysiloxanes, polyacrylates, and other related polymer-based paints and coatings with about 0.5 % polythiophene/small molecule additive composite with retention of the thermochromic behavior.
- thermochromic polymer-based pigments can be incorporated via injection molding or extrusion into many commercially important plastics such as poly (ethylene terephthalate) (PET), polysytrene, polyethylene (HDPE and LDPE), other polyolefins, polydienes, polycarbonates, poly acrylics, poly acrylic acids, poly aery lamides, polymethacrylics, polyvinyl ethers, polyvinyl halides, poly(vinyl nitrile)s poly vinyl esters, polyesters, polysulfones, poly sulfonamides, poly amides, polyimines, polyimides, carbohydrates, and polymer mixtures and copolymers.
- PET ethylene terephthalate
- HDPE and LDPE high density polyethylene
- other polyolefins polydienes
- polycarbonates poly acrylics, poly acrylic acids, poly aery lamides, polymethacrylics, polyvinyl ethers, polyvinyl halides, poly
- polythiophene/small molecule additive composite exhibiting controlled thermochromic transitions are dispersed in commercially available printable ink formulations, e.g. oil with resins, pigment extenders and other additives, to form thermal indicator ink systems.
- the polythiophenes are present in the thermal indicator ink in an amount of 1.0-25% by weight based on the total weight of the thermal indicator ink, preferably 7.0 to 14% weight.
- the ink can be printed using conventional methods such as ink-jet and letter press.
- Examples of ink formulations that polythiophene can be dispersed in can include combinations of resins such as cellulose, nitrocellulose with co-binders including polyamides, polyester amides, alkyd, epoxy acrylates, amine acrylates, polyurethanes, and polyvinyl butyral (UNI-REZ, UNI-JET, BECKOSOL,
- suitable oils such as napthenic petroleum oils and vegetable oils, e.g. soy bean oil
- suitable pigment extenders and additives that can include organic acids and esters of organic acids such as malic acid and organic solvents such as 1,5-pentanediol, diethylene glycol, along with other alcohols and related compounds (VERTEC, SYLFAT, UNI-KYD, and ICM, DY-SOLVE lines of additives.).
- the thermal indicator ink is printed on at least a portion of a suitable substrate, e.g. a portion of paper, plastic, or ceramic food/beverage containers, a portion of packaging materials for foods and goods, labels, a portion of labels, stickers, etc., using conventional printing methods.
- a suitable substrate e.g. a portion of paper, plastic, or ceramic food/beverage containers, a portion of packaging materials for foods and goods, labels, a portion of labels, stickers, etc.
- the polythiophenes dispersed in the ink system can be in particulate form and have diameters in the range of between about 0.01 - 0.1 microns thereby rendering the system suitable for fine printing.
- the thermal indicator material is applied to an article, e.g., a portion of paper, plastic or ceramic food/beverage containers, as a coating on an area of the article, or the entire article, which will be visible during the expected use of the article.
- the coating can be applied by any technique known in the art, such as by brush, roller, spraying, etc. Accordingly, the coatings typically have a thickness of 0.1 to 1000 microns.
- the thermal indicator material can also be absorbed on a surface or both absorbed and adsorbed on a surface.
- Suitable carrier mediums to be admixed with the polythiophene/small molecule additive composite exhibiting controlled reversible thermochromic transitions can include polyurethanes; elastomers including polysiloxanes and polydienes; polyacrylates, poly (ethylene terephthalate)s (PET), polysytrenes, polyolefins including polyethylenes (HDPE and LDPE) and polypropylene, polycarbonates, polyacrylics, poly aery lie acids, polyacrylamides, polymethacrylics, polyvinyl ethers, polyvinyl halides, polyvinyl nitrile)s polyvinyl esters, polyesters, polysofones, poly sulfonamides, polyamides, polyimines, polyimides, and carbohydrates.
- polyurethanes elastomers including polysiloxanes and polydienes
- polyacrylates poly (ethylene terephthalate)s (PET), polysytrenes, polyo
- addition of monomer (3-octadecylthiophene) to polymer results in a significant lowering of the thermochromic transition temperature, deepening of the color, and enhancement of the flourescence properties of poly(3-alkylthiophene)s.
- the addition of other small molecules such as octadecylbenzene have a similar effect.
- a sample of poly(3-octadecylthiophene) is light red in color at room temperature.
- thermochromic/thermoflourescent transition occurs at 65 C.
- thermochromic/thermoflourescent transition is lowered to 50 C.
- the high temperature color is yellow in both cases.
- monomer decreases the transition temperature by approximately 15 C.
- the flourescence is modified.
- thermochromic transition temperature a significant lowering of the thermochromic transition temperature and deepening of color.
- 3-octadecylthiophene to poly(3-octadecylthioophene) (2: 1 monomer:polymer by weight
- the color is changed from red/yellow to a deep purple at room temperature.
- thermochromic/thermoflourescent transition occurs at 50 C.
- thermochromic/thermoflourescent transition is lowered to 35 C.
- the high temperature color is yellow in both cases.
- the addition of monomer decreases the transition temperature by approximately 15 C.
- the change in thermochromic transition is related to the change in melting transition as measured by Differential Scanning Calorimetry (DSC), as seen in Figure 1.
- DSC Differential Scanning Calorimetry
- oligo(ethyleneglycol)dimethyl ether with Mn 250 to poly(3-oligoethylene oxide)-4-methylthiophene)s significantly lowers the thermochromic temperature.
- the thermochromic transition of the pure polymer occurs at 65 0 C.
- oligo(ethylene glycol)dimethyl ether the transition temperature is lowered to 5 0 C, as seen in Figure 2.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Measuring Temperature Or Quantity Of Heat (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68460305P | 2005-05-25 | 2005-05-25 | |
| PCT/US2006/019676 WO2006127569A2 (en) | 2005-05-25 | 2006-05-22 | Thermochromic and thermoflourescent pigments: enhancing color and flourescence with additives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1889049A2 true EP1889049A2 (de) | 2008-02-20 |
Family
ID=37452679
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP06770799A Withdrawn EP1889049A2 (de) | 2005-05-25 | 2006-05-22 | Thermochrome und thermofluoreszierende pigmente: intensivierung von farbe und fluoreszenz mit zusätzen |
Country Status (2)
| Country | Link |
|---|---|
| EP (1) | EP1889049A2 (de) |
| WO (1) | WO2006127569A2 (de) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG176983A1 (en) | 2009-07-08 | 2012-02-28 | Dermira Canada Inc | Tofa analogs useful in treating dermatological disorders or conditions |
| CN103575421B (zh) * | 2012-08-09 | 2016-05-04 | 中山市云创知识产权服务有限公司 | 发光二极管芯片的温度测量方法及使用的热敏高分子材料 |
| EP2843128A1 (de) * | 2013-09-03 | 2015-03-04 | Teijin Aramid B.V. | Synthetische Faser geeignet erfasst zu werden |
| US10184840B2 (en) | 2015-01-07 | 2019-01-22 | The Boeing Company | Portable device for quantifying thermochromatic coating signatures |
| US10352777B2 (en) * | 2015-01-07 | 2019-07-16 | The Boeing Company | Systems and methods for monitoring temperatures of batteries |
| CN105111415B (zh) * | 2015-09-15 | 2017-05-03 | 天津理工大学 | 一种侧链含萘基团的聚噻吩衍生物及其制备方法和应用 |
| EP3470195B1 (de) | 2017-10-12 | 2026-04-29 | The Procter & Gamble Company | Blasgeformter artikel mit visuellen effekten, vorformling, verfahren |
| US11046473B2 (en) | 2018-07-17 | 2021-06-29 | The Procter And Gamble Company | Blow molded article with visual effects |
| US11724847B2 (en) | 2018-10-19 | 2023-08-15 | The Procter & Gamble Company | Blow molded article with debossing |
| EP3953130B1 (de) | 2019-04-11 | 2024-08-14 | The Procter & Gamble Company | Blasgeformter artikel mit visuellen effekten |
| WO2021142194A1 (en) | 2020-01-08 | 2021-07-15 | The Procter & Gamble Company | Blow molded multilayer article with color gradient |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6706218B2 (en) * | 2000-01-11 | 2004-03-16 | The Board Of Governors For Higher Education, State Of Rhode Island And Providence Plantations | Thermochromic polymers for rapid visual assessment of temperature |
-
2006
- 2006-05-22 EP EP06770799A patent/EP1889049A2/de not_active Withdrawn
- 2006-05-22 WO PCT/US2006/019676 patent/WO2006127569A2/en not_active Ceased
Non-Patent Citations (1)
| Title |
|---|
| See references of WO2006127569A3 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006127569A2 (en) | 2006-11-30 |
| WO2006127569A3 (en) | 2007-11-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7943063B2 (en) | Thermochromic indicator materials with controlled reversibility | |
| CA2434754C (en) | Thermochromic polymers for rapid visual assessment of temperature | |
| JP5470947B2 (ja) | 温度時間経歴表示体およびそれを用いた表示方法 | |
| WO2006127569A2 (en) | Thermochromic and thermoflourescent pigments: enhancing color and flourescence with additives | |
| JP5129397B2 (ja) | 温度管理インジケータ及びそれが付された構造物 | |
| Ciardelli et al. | Dye-containing polymers: methods for preparation of mechanochromic materials | |
| JP2010520945A (ja) | インクジェット可能な重合性液晶混合物 | |
| CN102015818A (zh) | 低温不可逆热变色组合物 | |
| Bao et al. | Reversible thermochromic switching of fluorescent poly (vinylidene fluoride) composite containing bis (benzoxazolyl) stilbene dye | |
| US7833438B2 (en) | Thermofluorescent pigments for security and safety applications | |
| KR920022219A (ko) | 가시정보기록매체 | |
| Sadoh et al. | Thermochromic Polymeric Films for Applications in Active Intelligent Packaging—An Overview. Micromachines 2021, 12, 1193 | |
| Owezsahedov et al. | POSSIBILITIES OF OBTAINING TERMOHROMIC PIGMENTS FOR TERMOCHROMIC PAINTS | |
| Liu et al. | Mechanofluorochromic Polymer Composites | |
| AU2002332413A1 (en) | Thermochromic polymers for rapid visual assessment of temperature |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| 17P | Request for examination filed |
Effective date: 20071127 |
|
| AK | Designated contracting states |
Kind code of ref document: A2 Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI SK TR |
|
| AX | Request for extension of the european patent |
Extension state: AL BA HR MK YU |
|
| DAX | Request for extension of the european patent (deleted) | ||
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
| 18D | Application deemed to be withdrawn |
Effective date: 20091201 |