JPH0129398B2 - - Google Patents
Info
- Publication number
- JPH0129398B2 JPH0129398B2 JP59131535A JP13153584A JPH0129398B2 JP H0129398 B2 JPH0129398 B2 JP H0129398B2 JP 59131535 A JP59131535 A JP 59131535A JP 13153584 A JP13153584 A JP 13153584A JP H0129398 B2 JPH0129398 B2 JP H0129398B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- temperature
- phosphate
- fatty acid
- compounds
- 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.)
- Expired
Links
- 239000000203 mixture Substances 0.000 claims description 59
- -1 aromatic carboxylic acids Chemical class 0.000 claims description 47
- 230000002441 reversible effect Effects 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 19
- 238000002844 melting Methods 0.000 claims description 15
- 230000008018 melting Effects 0.000 claims description 15
- 229910052751 metal Chemical class 0.000 claims description 14
- 239000002184 metal Chemical class 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 239000003094 microcapsule Substances 0.000 claims description 6
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 230000001747 exhibiting effect Effects 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical class [H]O* 0.000 claims description 4
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 claims description 4
- 150000002894 organic compounds Chemical class 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 3
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- VCZVPMCCBMEIIG-UHFFFAOYSA-N docosyl butanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCOC(=O)CCC VCZVPMCCBMEIIG-UHFFFAOYSA-N 0.000 claims description 3
- NJVKAQGGBANCKG-UHFFFAOYSA-N hexadecyl butyrate Chemical compound CCCCCCCCCCCCCCCCOC(=O)CCC NJVKAQGGBANCKG-UHFFFAOYSA-N 0.000 claims description 3
- VTTIDPAZLXIGNF-UHFFFAOYSA-N octadecyl butanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC VTTIDPAZLXIGNF-UHFFFAOYSA-N 0.000 claims description 3
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims 1
- 239000002253 acid Substances 0.000 description 34
- 229910019142 PO4 Inorganic materials 0.000 description 30
- 239000010452 phosphate Substances 0.000 description 30
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 27
- 239000000463 material Substances 0.000 description 16
- 238000002845 discoloration Methods 0.000 description 12
- 238000000034 method Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 4
- 238000004806 packaging method and process Methods 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 235000013824 polyphenols Nutrition 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- BZOHZRICIZZXBZ-UHFFFAOYSA-N 2-methylbutyl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(C)CC BZOHZRICIZZXBZ-UHFFFAOYSA-N 0.000 description 3
- YQUVCSBJEUQKSH-UHFFFAOYSA-N 3,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000011133 lead Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- 239000011733 molybdenum Substances 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000011135 tin Substances 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 230000001052 transient effect Effects 0.000 description 3
- 229910052720 vanadium Inorganic materials 0.000 description 3
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 2
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
- XRXMNWGCKISMOH-UHFFFAOYSA-N 2-bromobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Br XRXMNWGCKISMOH-UHFFFAOYSA-N 0.000 description 2
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 2
- XDZMPRGFOOFSBL-UHFFFAOYSA-N 2-ethoxybenzoic acid Chemical compound CCOC1=CC=CC=C1C(O)=O XDZMPRGFOOFSBL-UHFFFAOYSA-N 0.000 description 2
- LEHHQPHLKGGRJW-UHFFFAOYSA-N 2-methylhexyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(C)CCCC LEHHQPHLKGGRJW-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- YBPFWNXHTBDOQJ-UHFFFAOYSA-N 3,5,5-trimethylhexyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCC(C)CC(C)(C)C YBPFWNXHTBDOQJ-UHFFFAOYSA-N 0.000 description 2
- TZPXVFBTQVLCLG-UHFFFAOYSA-N 3-methylbutyl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCCC(C)C TZPXVFBTQVLCLG-UHFFFAOYSA-N 0.000 description 2
- KDVYCTOWXSLNNI-UHFFFAOYSA-N 4-t-Butylbenzoic acid Chemical compound CC(C)(C)C1=CC=C(C(O)=O)C=C1 KDVYCTOWXSLNNI-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 238000012695 Interfacial polymerization Methods 0.000 description 2
- 239000005639 Lauric acid Substances 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- 238000005354 coacervation Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- KBPUBCVJHFXPOC-UHFFFAOYSA-N ethyl 3,4-dihydroxybenzoate Chemical compound CCOC(=O)C1=CC=C(O)C(O)=C1 KBPUBCVJHFXPOC-UHFFFAOYSA-N 0.000 description 2
- VFPFQHQNJCMNBZ-UHFFFAOYSA-N ethyl gallate Chemical compound CCOC(=O)C1=CC(O)=C(O)C(O)=C1 VFPFQHQNJCMNBZ-UHFFFAOYSA-N 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 description 2
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 229940074391 gallic acid Drugs 0.000 description 2
- 235000004515 gallic acid Nutrition 0.000 description 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229940107698 malachite green Drugs 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- FBSFWRHWHYMIOG-UHFFFAOYSA-N methyl 3,4,5-trihydroxybenzoate Chemical compound COC(=O)C1=CC(O)=C(O)C(O)=C1 FBSFWRHWHYMIOG-UHFFFAOYSA-N 0.000 description 2
- CUFLZUDASVUNOE-UHFFFAOYSA-N methyl 3,4-dihydroxybenzoate Chemical compound COC(=O)C1=CC=C(O)C(O)=C1 CUFLZUDASVUNOE-UHFFFAOYSA-N 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 2
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- OMJRVNYAQYMXFR-UHFFFAOYSA-N octan-2-yl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(C)CCCCCC OMJRVNYAQYMXFR-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 229920006267 polyester film Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 229940043267 rhodamine b Drugs 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 235000010413 sodium alginate Nutrition 0.000 description 2
- 239000000661 sodium alginate Substances 0.000 description 2
- 229940005550 sodium alginate Drugs 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- VUFLYQCAPHNLBQ-UHFFFAOYSA-N (2,3-dimethylphenyl) phenyl hydrogen phosphate Chemical compound CC1=CC=CC(OP(O)(=O)OC=2C=CC=CC=2)=C1C VUFLYQCAPHNLBQ-UHFFFAOYSA-N 0.000 description 1
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- 229940005605 valeric acid Drugs 0.000 description 1
- WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 description 1
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000002699 waste material 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
- G01K11/00—Measuring temperature based upon physical or chemical changes not covered by groups G01K3/00, G01K5/00, G01K7/00 or G01K9/00
- G01K11/12—Measuring temperature based upon physical or chemical changes not covered by groups G01K3/00, G01K5/00, G01K7/00 or G01K9/00 using changes in colour, translucency or reflectance
- G01K11/16—Measuring temperature based upon physical or chemical changes not covered by groups G01K3/00, G01K5/00, G01K7/00 or G01K9/00 using changes in colour, translucency or reflectance of organic materials
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
- B41M5/305—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers with reversible electron-donor electron-acceptor compositions
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S252/00—Compositions
- Y10S252/962—Temperature or thermal history
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2984—Microcapsule with fluid core [includes liposome]
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Color Printing (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59131535A JPS619488A (ja) | 1984-06-26 | 1984-06-26 | 可逆性感熱示温組成物 |
| DE3545813A DE3545813C2 (de) | 1984-06-26 | 1985-12-23 | Reversible Temperaturanzeigezusammensetzung |
| US06/812,572 US4732810A (en) | 1984-06-26 | 1985-12-23 | Reversible temperature-indicating composition |
| GB08531817A GB2184450A (en) | 1984-06-26 | 1985-12-24 | Reversible temperature-indicating compositions |
| FR8519140A FR2592158B1 (fr) | 1984-06-26 | 1985-12-24 | Composition indiquant la temperature de maniere reversible. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59131535A JPS619488A (ja) | 1984-06-26 | 1984-06-26 | 可逆性感熱示温組成物 |
| FR8519140A FR2592158B1 (fr) | 1984-06-26 | 1985-12-24 | Composition indiquant la temperature de maniere reversible. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS619488A JPS619488A (ja) | 1986-01-17 |
| JPH0129398B2 true JPH0129398B2 (US06373033-20020416-M00071.png) | 1989-06-09 |
Family
ID=37872284
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59131535A Granted JPS619488A (ja) | 1984-06-26 | 1984-06-26 | 可逆性感熱示温組成物 |
Country Status (5)
Cited By (15)
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|---|---|---|---|---|
| JP2002012787A (ja) * | 2000-04-28 | 2002-01-15 | Pilot Ink Co Ltd | 可逆熱変色性マイクロカプセル顔料 |
| JP2006206622A (ja) * | 2005-01-25 | 2006-08-10 | Pilot Ink Co Ltd | 可逆熱変色性組成物及びそれを内包した可逆熱変色性マイクロカプセル顔料 |
| EP1820662A2 (en) | 2006-01-27 | 2007-08-22 | The Pilot Ink Co., Ltd. | Friction body, writing instrument and writing instrument set |
| WO2008047805A1 (fr) | 2006-10-17 | 2008-04-24 | The Pilot Ink Co., Ltd. | Instrument d'écriture et ensemble d'instruments d'écriture |
| EP1939259A2 (en) | 2006-11-29 | 2008-07-02 | The Pilot Ink Co., Ltd. | Friction body, writing instrument and writing instrument set |
| WO2011021610A1 (ja) | 2009-08-18 | 2011-02-24 | パイロットインキ株式会社 | 可逆熱変色性水性インキ組成物及びそれを用いた筆記具、筆記具セット |
| JP2011156832A (ja) * | 2010-02-04 | 2011-08-18 | Pilot Ink Co Ltd | 摩擦具及びそれを備えた筆記具 |
| JP2018001696A (ja) * | 2016-07-07 | 2018-01-11 | 平岡織染株式会社 | 可撓性調光シート |
| JP2018008473A (ja) * | 2016-07-15 | 2018-01-18 | 平岡織染株式会社 | 可撓性調光シート |
| WO2018116767A1 (ja) | 2016-12-19 | 2018-06-28 | 株式会社パイロットコーポレーション | 摩擦体並びに筆記具及び筆記セット |
| WO2019082722A1 (ja) | 2017-10-23 | 2019-05-02 | 株式会社パイロットコーポレーション | 可逆熱変色性水性インキ組成物、およびそれを用いた筆記具 |
| WO2021200474A1 (ja) | 2020-03-31 | 2021-10-07 | 株式会社パイロットコーポレーション | 熱変色性筆記具 |
| WO2022065229A1 (ja) | 2020-09-28 | 2022-03-31 | パイロットインキ株式会社 | 可逆熱変色性組成物およびそれを内包してなる可逆熱変色性マイクロカプセル顔料 |
| WO2022065228A1 (ja) | 2020-09-28 | 2022-03-31 | パイロットインキ株式会社 | 可逆熱変色性組成物およびそれを内包してなる可逆熱変色性マイクロカプセル顔料 |
| WO2022255079A1 (ja) | 2021-05-31 | 2022-12-08 | 株式会社パイロットコーポレーション | 筆記具用インキ組成物及び筆記具用インキ組成物を収容してなる筆記具 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4895827A (en) * | 1987-12-04 | 1990-01-23 | Appleton Papers Inc. | Thermally-responsive record material |
| US4820683A (en) * | 1987-12-04 | 1989-04-11 | Appleton Papers Inc. | Thermally-responsive record material |
| JPH02126126A (ja) * | 1988-11-02 | 1990-05-15 | Stanley Electric Co Ltd | 温度分布調査方法 |
| DE4020740A1 (de) * | 1990-05-29 | 1991-12-05 | Merck Patent Gmbh | Verfahren zur herstellung mikroverkapselter fluessigkristalle |
| JP3751028B2 (ja) * | 1992-02-28 | 2006-03-01 | 三菱製紙株式会社 | 蓄熱材用マイクロカプセル |
| JP3134108B2 (ja) * | 1992-10-26 | 2001-02-13 | パイロットインキ株式会社 | 熱変色性遮光性組成物及びこれを用いた積層体及び前記積層体を用いた内部隠顕立体物 |
| US5441418A (en) * | 1993-05-20 | 1995-08-15 | Binney & Smith Inc. | Thermochromic drawing device |
| CA2138897C (en) * | 1993-12-24 | 1998-04-21 | Akio Nakashima | Thermochromic color-memory composition |
| US5514635A (en) * | 1993-12-29 | 1996-05-07 | Optum Corporation | Thermal writing surface and method for making the same |
| US5868821A (en) * | 1996-01-31 | 1999-02-09 | Richo Company, Ltd. | Thermally reversible color forming composition and thermally reversible recording medium using the thermally reversible color forming composition |
| US5919404A (en) * | 1997-04-23 | 1999-07-06 | The Pilot Ink Co., Ltd. | Reversible thermochromic compositions |
| JP3917269B2 (ja) * | 1997-10-07 | 2007-05-23 | パイロットインキ株式会社 | 可逆熱変色性組成物 |
| CA2253160A1 (en) | 1997-10-31 | 1999-04-30 | The Pilot Ink Co., Ltd. | Color-change materials |
| US6294502B1 (en) | 1998-05-22 | 2001-09-25 | Bayer Aktiengesellschaft | Thermally-responsive record material |
| US6753047B1 (en) | 1999-06-10 | 2004-06-22 | Ppg Industries Ohio, Inc. | Electrodes for liquid crystal cells |
| CA2318700A1 (en) | 1999-09-17 | 2001-03-17 | Katsuyuki Fujita | Thermochromic microencapsulated pigments |
| CA2324637A1 (en) | 1999-10-29 | 2001-04-29 | Nobuaki Matsunami | Solid having reversibly invisible/visible thermochromic construction enclosed therein |
| JP4303396B2 (ja) * | 2000-04-13 | 2009-07-29 | パイロットインキ株式会社 | 可逆熱変色性紫外線硬化型インキ及びそれを用いた可逆熱変色性積層体 |
| US6554447B1 (en) | 2000-04-14 | 2003-04-29 | S. C. Johnson & Son, Inc. | Candle product decorated with heat-shrinkable film and related method |
| JP2002129055A (ja) * | 2000-10-31 | 2002-05-09 | Pilot Ink Co Ltd | 可逆熱変色性マイクロカプセル顔料 |
| JP2002234119A (ja) | 2000-12-04 | 2002-08-20 | Pilot Ink Co Ltd | 可逆熱変色遮光性−透光性積層体 |
| JP2002234260A (ja) | 2000-12-04 | 2002-08-20 | Pilot Ink Co Ltd | 可逆熱変色透光性積層体 |
| EP1221500A1 (en) * | 2001-01-04 | 2002-07-10 | The Pilot Ink Co., Ltd. | Thermochromic acrylic synthetic fiber, its processed article, and process for producing thermochromic acrylic synthetic fiber |
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| DE10110019C1 (de) * | 2001-03-01 | 2002-07-25 | Spelsberg Guenther Gmbh Co Kg | Gehäuse mit Temperaturwarnung |
| JP2002369978A (ja) | 2001-04-13 | 2002-12-24 | Pilot Ink Co Ltd | 水変色性印刷物及びそれを用いた水変色性玩具 |
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| US7278369B2 (en) * | 2002-02-06 | 2007-10-09 | The University Of Akron | Temperature indicator using thermochromic materials |
| WO2004003498A2 (en) * | 2002-06-28 | 2004-01-08 | The Board Of Governors For Higher Education State Of Rhode Island And Providence Plantations | Thermochromic indicator materials with controlled reversibility |
| US7011425B2 (en) * | 2003-08-01 | 2006-03-14 | S.C. Johnson & Son, Inc. | Luminary product |
| US20050104035A1 (en) * | 2003-11-13 | 2005-05-19 | Christopher Eaddy | Intelligent label for informing consumers of product quality criteria |
| US20050177215A1 (en) * | 2004-02-11 | 2005-08-11 | Rosenberg Steven L. | Method and device for lower extremity cryo-thermo therapy |
| US7513682B2 (en) * | 2004-05-11 | 2009-04-07 | Hewlett-Packard Development Company, L.P. | Temperature monitoring system |
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| US7465693B2 (en) * | 2006-09-13 | 2008-12-16 | Flint Trading, Inc. | Thermochromatic temperature marking for outdoor surfaces |
| WO2008037076A1 (en) * | 2006-09-27 | 2008-04-03 | Luvgear Inc. | Device and method for identifying a change in a predetermined condition |
| US20080145940A1 (en) * | 2006-12-18 | 2008-06-19 | 3M Innovative Properties Company | Chemical indicator test strip |
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| FR2923906B1 (fr) * | 2007-11-19 | 2010-01-22 | Fagorbrandt Sas | Accessoire de conservation d'aliments destine a etre introduit dans une enceinte d'un appareil de congelation constitue d'un materiau thermochromique. |
| US20090153837A1 (en) * | 2007-12-17 | 2009-06-18 | Bwt Property, Inc. | Optical power monitor based on thermo-chromic material |
| US8986915B2 (en) | 2009-02-16 | 2015-03-24 | Toshiba Tec Kabushiki Kaisha | Toner, method for producing the same, cartridge storing the same, process cartridge, and image forming apparatus |
| CN101807018B (zh) * | 2009-02-16 | 2013-10-16 | 东芝泰格有限公司 | 显影剂及其制造方法 |
| US20100304142A1 (en) * | 2009-05-27 | 2010-12-02 | Toshiba Tec Kabushiki Kaisha | Color erasable recording material and method for producing the same |
| US9145514B2 (en) * | 2010-03-31 | 2015-09-29 | Nichiyu Giken Kogyo Co., Ltd. | Temperature management indicator and structure having the same attached |
| DE102011006362A1 (de) * | 2011-03-29 | 2012-10-04 | Evonik Goldschmidt Gmbh | Isopentylester zur Verwendung in kosmetischen, dermatologischen oder pharmazeutischen Kompositionen |
| US8709973B2 (en) | 2011-12-31 | 2014-04-29 | Sanford, L.P. | Irreversible thermochromic ink compositions |
| US8664156B2 (en) | 2011-12-31 | 2014-03-04 | Sanford, L.P. | Irreversible thermochromic ink compositions |
| US8652996B2 (en) | 2011-12-31 | 2014-02-18 | Sanford, L.P. | Irreversible thermochromic pigment capsules |
| FR2986324A1 (fr) * | 2012-01-30 | 2013-08-02 | Gem Innov | Indicateur de respect d'une plage de temperature |
| US8865621B2 (en) | 2012-08-06 | 2014-10-21 | Sanford, L.P. | Irreversible color changing ink compositions |
| WO2017038292A1 (ja) * | 2015-09-03 | 2017-03-09 | 株式会社日立製作所 | 温度履歴表示体 |
| JP6533833B2 (ja) * | 2015-10-21 | 2019-06-19 | 株式会社日立製作所 | 温度検知体 |
| DE202016004825U1 (de) | 2016-08-05 | 2017-11-07 | Stabilo International Gmbh | Löschbare Tinte und ihre Verwendung |
| DE102016214617B4 (de) | 2016-08-05 | 2022-06-23 | Stabilo International Gmbh | Löschbare Tinte, deren Verwendung und Tintenpatrone die mit der löschbaren Tinte befült ist |
| DE202016005058U1 (de) | 2016-08-17 | 2017-11-19 | Stabilo International Gmbh | Löschbare Tinte und ihre Verwendung |
| WO2019178083A1 (en) * | 2018-03-14 | 2019-09-19 | Temptime Corporation | Descending and ascending temperature indicators utilizing deep eutectics |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US3079351A (en) * | 1958-11-26 | 1963-02-26 | Moore Business Forms Inc | Copying materials and emulsions |
| GB1053905A (US06373033-20020416-M00071.png) * | 1964-05-11 | |||
| ES390653A1 (es) * | 1970-04-28 | 1974-03-16 | Fuji Photo Film Co Ltd | Procedimiento para la produccion de microcapsulas conte- niendo liquido aceitoso. |
| US4028118A (en) * | 1972-05-30 | 1977-06-07 | Pilot Ink Co., Ltd. | Thermochromic materials |
| GB1405701A (en) * | 1973-09-13 | 1975-09-10 | Pilot Ink Co Ltd | Thermochromic materials |
| US4197346A (en) * | 1978-10-10 | 1980-04-08 | Appleton Papers Inc. | Self-contained pressure-sensitive record material and process of preparation |
| US4301054A (en) * | 1979-06-04 | 1981-11-17 | Thermal Imagery, Inc. | Thermographic cholesteric coating compositions |
| JPS5790085A (en) * | 1980-11-27 | 1982-06-04 | Pilot Ink Co Ltd | Thermochromic material |
| JPS57167380A (en) * | 1981-04-08 | 1982-10-15 | Pilot Ink Co Ltd | Thermochromic material |
| JPS59120492A (ja) * | 1982-12-27 | 1984-07-12 | Pilot Ink Co Ltd | 可逆性感熱記録材料 |
| EP0138741B1 (en) * | 1983-09-05 | 1990-11-07 | Matsumoto Kosan Kabushiki Kaisha | Temperature-indicating sheet |
| JPS60242094A (ja) * | 1984-05-17 | 1985-12-02 | Fuji Photo Film Co Ltd | 感熱記録材料 |
-
1984
- 1984-06-26 JP JP59131535A patent/JPS619488A/ja active Granted
-
1985
- 1985-12-23 US US06/812,572 patent/US4732810A/en not_active Expired - Lifetime
- 1985-12-23 DE DE3545813A patent/DE3545813C2/de not_active Expired - Lifetime
- 1985-12-24 FR FR8519140A patent/FR2592158B1/fr not_active Expired - Lifetime
- 1985-12-24 GB GB08531817A patent/GB2184450A/en active Granted
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002012787A (ja) * | 2000-04-28 | 2002-01-15 | Pilot Ink Co Ltd | 可逆熱変色性マイクロカプセル顔料 |
| JP2006206622A (ja) * | 2005-01-25 | 2006-08-10 | Pilot Ink Co Ltd | 可逆熱変色性組成物及びそれを内包した可逆熱変色性マイクロカプセル顔料 |
| EP1820662A2 (en) | 2006-01-27 | 2007-08-22 | The Pilot Ink Co., Ltd. | Friction body, writing instrument and writing instrument set |
| EP3521054A1 (en) | 2006-01-27 | 2019-08-07 | The Pilot Ink Co., Ltd. | Friction body, writing instrument and writing instrument set |
| EP3059095A1 (en) | 2006-10-17 | 2016-08-24 | The Pilot Ink Co., Ltd. | Writing instrument and writing instrument set |
| WO2008047805A1 (fr) | 2006-10-17 | 2008-04-24 | The Pilot Ink Co., Ltd. | Instrument d'écriture et ensemble d'instruments d'écriture |
| EP1939259A2 (en) | 2006-11-29 | 2008-07-02 | The Pilot Ink Co., Ltd. | Friction body, writing instrument and writing instrument set |
| US8845799B2 (en) | 2009-08-18 | 2014-09-30 | The Pilot Ink Co., Ltd. | Reversibly thermochromic aqueous ink composition, and writing instrument and writing instrument set each utilizing same |
| WO2011021610A1 (ja) | 2009-08-18 | 2011-02-24 | パイロットインキ株式会社 | 可逆熱変色性水性インキ組成物及びそれを用いた筆記具、筆記具セット |
| JP2011156832A (ja) * | 2010-02-04 | 2011-08-18 | Pilot Ink Co Ltd | 摩擦具及びそれを備えた筆記具 |
| JP2018001696A (ja) * | 2016-07-07 | 2018-01-11 | 平岡織染株式会社 | 可撓性調光シート |
| JP2018008473A (ja) * | 2016-07-15 | 2018-01-18 | 平岡織染株式会社 | 可撓性調光シート |
| WO2018116767A1 (ja) | 2016-12-19 | 2018-06-28 | 株式会社パイロットコーポレーション | 摩擦体並びに筆記具及び筆記セット |
| WO2019082722A1 (ja) | 2017-10-23 | 2019-05-02 | 株式会社パイロットコーポレーション | 可逆熱変色性水性インキ組成物、およびそれを用いた筆記具 |
| US11267978B2 (en) | 2017-10-23 | 2022-03-08 | Kabushiki Kaisha Pilot Corporation | Reversibly thermochromic aqueous ink composition and writing instrument using the same |
| WO2021200474A1 (ja) | 2020-03-31 | 2021-10-07 | 株式会社パイロットコーポレーション | 熱変色性筆記具 |
| WO2022065229A1 (ja) | 2020-09-28 | 2022-03-31 | パイロットインキ株式会社 | 可逆熱変色性組成物およびそれを内包してなる可逆熱変色性マイクロカプセル顔料 |
| WO2022065228A1 (ja) | 2020-09-28 | 2022-03-31 | パイロットインキ株式会社 | 可逆熱変色性組成物およびそれを内包してなる可逆熱変色性マイクロカプセル顔料 |
| WO2022255079A1 (ja) | 2021-05-31 | 2022-12-08 | 株式会社パイロットコーポレーション | 筆記具用インキ組成物及び筆記具用インキ組成物を収容してなる筆記具 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8531817D0 (en) | 1986-02-05 |
| DE3545813C2 (de) | 1994-02-24 |
| GB2184450B (US06373033-20020416-M00071.png) | 1989-10-18 |
| FR2592158B1 (fr) | 1992-07-31 |
| GB2184450A (en) | 1987-06-24 |
| JPS619488A (ja) | 1986-01-17 |
| US4732810A (en) | 1988-03-22 |
| DE3545813A1 (de) | 1987-06-25 |
| FR2592158A1 (fr) | 1987-06-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |