CA2152544C - Compositions a changement de couleur pour surligneurs - Google Patents

Compositions a changement de couleur pour surligneurs Download PDF

Info

Publication number: CA2152544C
Authority: CA; Canada
Prior art keywords: coloring composition; overcolor; undercolor; weight; dye
Prior art date: 1994-10-03
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 - Fee Related

Application number

CA 2152544

Other languages

English (en)

Other versions

CA2152544A1 (fr

Inventor

Richard E. Miller

Cheryl P. Krieger

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Binney and Smith Inc

Original Assignee

Binney and Smith Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1994-10-03

Filing date

1995-06-23

Publication date

2000-02-01

1994-10-03 Priority claimed from US08/317,139 external-priority patent/US5492558A/en

1995-06-23 Application filed by Binney and Smith Inc filed Critical Binney and Smith Inc

1996-04-04 Publication of CA2152544A1 publication Critical patent/CA2152544A1/fr

2000-02-01 Application granted granted Critical

2000-02-01 Publication of CA2152544C publication Critical patent/CA2152544C/fr

2015-06-23 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 311
238000004040 coloring Methods 0.000 claims abstract description 273
239000003638 chemical reducing agent Substances 0.000 claims abstract description 69
239000004094 surface-active agent Substances 0.000 claims abstract description 52
239000000975 dye Substances 0.000 claims description 104
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 51
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
239000003755 preservative agent Substances 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 17
239000002274 desiccant Substances 0.000 claims description 12
239000003906 humectant Substances 0.000 claims description 11
230000002335 preservative effect Effects 0.000 claims description 9
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 8
XKTMIJODWOEBKO-UHFFFAOYSA-M Guinee green B Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C=CC=CC=2)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 XKTMIJODWOEBKO-UHFFFAOYSA-M 0.000 claims description 6
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
NJIRSTSECXKPCO-UHFFFAOYSA-M 3-[n-methyl-4-[2-(1,3,3-trimethylindol-1-ium-2-yl)ethenyl]anilino]propanenitrile;chloride Chemical compound [Cl-].C1=CC(N(CCC#N)C)=CC=C1\C=C\C1=[N+](C)C2=CC=CC=C2C1(C)C NJIRSTSECXKPCO-UHFFFAOYSA-M 0.000 claims description 5
MCPLVIGCWWTHFH-UHFFFAOYSA-L methyl blue Chemical compound [Na+].[Na+].C1=CC(S(=O)(=O)[O-])=CC=C1NC1=CC=C(C(=C2C=CC(C=C2)=[NH+]C=2C=CC(=CC=2)S([O-])(=O)=O)C=2C=CC(NC=3C=CC(=CC=3)S([O-])(=O)=O)=CC=2)C=C1 MCPLVIGCWWTHFH-UHFFFAOYSA-L 0.000 claims description 5
RZUBARUFLYGOGC-MTHOTQAESA-L acid fuchsin Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=C(N)C(C)=CC(C(=C\2C=C(C(=[NH2+])C=C/2)S([O-])(=O)=O)\C=2C=C(C(N)=CC=2)S([O-])(=O)=O)=C1 RZUBARUFLYGOGC-MTHOTQAESA-L 0.000 claims description 4
239000000987 azo dye Substances 0.000 claims description 4
KXXXUIKPSVVSAW-UHFFFAOYSA-K pyranine Chemical compound [Na+].[Na+].[Na+].C1=C2C(O)=CC(S([O-])(=O)=O)=C(C=C3)C2=C2C3=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1 KXXXUIKPSVVSAW-UHFFFAOYSA-K 0.000 claims description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
235000010265 sodium sulphite Nutrition 0.000 claims description 4
AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 claims description 3
239000001018 xanthene dye Substances 0.000 claims description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 2
239000005708 Sodium hypochlorite Substances 0.000 claims description 2
239000000908 ammonium hydroxide Substances 0.000 claims description 2
229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 2
229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 2
230000000694 effects Effects 0.000 abstract description 6
239000000976 ink Substances 0.000 description 69
239000003550 marker Substances 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
239000000463 material Substances 0.000 description 14
239000003086 colorant Substances 0.000 description 13
PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
235000019441 ethanol Nutrition 0.000 description 9
-1 and of these Substances 0.000 description 6
239000003963 antioxidant agent Substances 0.000 description 6
239000008367 deionised water Substances 0.000 description 6
229910021641 deionized water Inorganic materials 0.000 description 6
SEACYXSIPDVVMV-UHFFFAOYSA-L eosin Y Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 SEACYXSIPDVVMV-UHFFFAOYSA-L 0.000 description 6
235000011187 glycerol Nutrition 0.000 description 6
239000000758 substrate Substances 0.000 description 6
230000003078 antioxidant effect Effects 0.000 description 5
230000008901 benefit Effects 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
238000005562 fading Methods 0.000 description 5
238000001035 drying Methods 0.000 description 4
230000008030 elimination Effects 0.000 description 4
238000003379 elimination reaction Methods 0.000 description 4
239000000835 fiber Substances 0.000 description 4
238000009472 formulation Methods 0.000 description 4
GVKCHTBDSMQENH-UHFFFAOYSA-L phloxine B Chemical compound [Na+].[Na+].[O-]C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 GVKCHTBDSMQENH-UHFFFAOYSA-L 0.000 description 4
239000000126 substance Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
244000025254 Cannabis sativa Species 0.000 description 3
244000260524 Chrysanthemum balsamita Species 0.000 description 3
235000005633 Chrysanthemum balsamita Nutrition 0.000 description 3
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
SEVNKWFHTNVOLD-UHFFFAOYSA-L copper;3-(4-ethylcyclohexyl)propanoate;3-(3-ethylcyclopentyl)propanoate Chemical compound [Cu+2].CCC1CCC(CCC([O-])=O)C1.CCC1CCC(CCC([O-])=O)CC1 SEVNKWFHTNVOLD-UHFFFAOYSA-L 0.000 description 3
235000013305 food Nutrition 0.000 description 3
ZTBANYZVKCGOKD-UHFFFAOYSA-M n-(2-chloroethyl)-n-methyl-4-[2-(1,3,3-trimethylindol-1-ium-2-yl)ethenyl]aniline;chloride Chemical compound [Cl-].C1=CC(N(CCCl)C)=CC=C1C=CC1=[N+](C)C2=CC=CC=C2C1(C)C ZTBANYZVKCGOKD-UHFFFAOYSA-M 0.000 description 3
BFHKYHMIVDBCPC-UHFFFAOYSA-N 1,3,5,7-tetrahydro-[1,3]oxazolo[3,4-c][1,3]oxazol-7a-ylmethanol Chemical compound C1OCN2COCC21CO BFHKYHMIVDBCPC-UHFFFAOYSA-N 0.000 description 2
DHVLDKHFGIVEIP-UHFFFAOYSA-N 2-bromo-2-(bromomethyl)pentanedinitrile Chemical compound BrCC(Br)(C#N)CCC#N DHVLDKHFGIVEIP-UHFFFAOYSA-N 0.000 description 2
SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
239000004677 Nylon Substances 0.000 description 2
239000004952 Polyamide Substances 0.000 description 2
239000004743 Polypropylene Substances 0.000 description 2
229920003081 Povidone K 30 Polymers 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
239000000654 additive Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
239000003945 anionic surfactant Substances 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
239000003398 denaturant Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
IINNWAYUJNWZRM-UHFFFAOYSA-L erythrosin B Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 IINNWAYUJNWZRM-UHFFFAOYSA-L 0.000 description 2
229940011411 erythrosine Drugs 0.000 description 2
235000012732 erythrosine Nutrition 0.000 description 2
239000004174 erythrosine Substances 0.000 description 2
239000012530 fluid Substances 0.000 description 2
239000000417 fungicide Substances 0.000 description 2
230000005484 gravity Effects 0.000 description 2
SXQCTESRRZBPHJ-UHFFFAOYSA-M lissamine rhodamine Chemical compound [Na+].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S([O-])(=O)=O)C=C1S([O-])(=O)=O SXQCTESRRZBPHJ-UHFFFAOYSA-M 0.000 description 2
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 2
229920001778 nylon Polymers 0.000 description 2
239000003973 paint Substances 0.000 description 2
239000004033 plastic Substances 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
229920002647 polyamide Polymers 0.000 description 2
229920000728 polyester Polymers 0.000 description 2
229920001155 polypropylene Polymers 0.000 description 2
239000000047 product Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
230000003245 working effect Effects 0.000 description 2
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
VUWCWMOCWKCZTA-UHFFFAOYSA-N 1,2-thiazol-4-one Chemical class O=C1CSN=C1 VUWCWMOCWKCZTA-UHFFFAOYSA-N 0.000 description 1
MHOFGBJTSNWTDT-UHFFFAOYSA-M 2-[n-ethyl-4-[(6-methoxy-3-methyl-1,3-benzothiazol-3-ium-2-yl)diazenyl]anilino]ethanol;methyl sulfate Chemical compound COS([O-])(=O)=O.C1=CC(N(CCO)CC)=CC=C1N=NC1=[N+](C)C2=CC=C(OC)C=C2S1 MHOFGBJTSNWTDT-UHFFFAOYSA-M 0.000 description 1
WXLPKTIAUMCNDX-UHFFFAOYSA-N 2h-pyran-3-ol Chemical compound OC1=CC=COC1 WXLPKTIAUMCNDX-UHFFFAOYSA-N 0.000 description 1
OALHHIHQOFIMEF-UHFFFAOYSA-N 3',6'-dihydroxy-2',4',5',7'-tetraiodo-3h-spiro[2-benzofuran-1,9'-xanthene]-3-one Chemical class O1C(=O)C2=CC=CC=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 OALHHIHQOFIMEF-UHFFFAOYSA-N 0.000 description 1
229940099451 3-iodo-2-propynylbutylcarbamate Drugs 0.000 description 1
WYVVKGNFXHOCQV-UHFFFAOYSA-N 3-iodoprop-2-yn-1-yl butylcarbamate Chemical compound CCCCNC(=O)OCC#CI WYVVKGNFXHOCQV-UHFFFAOYSA-N 0.000 description 1
IHZXTIBMKNSJCJ-UHFFFAOYSA-N 3-{[(4-{[4-(dimethylamino)phenyl](4-{ethyl[(3-sulfophenyl)methyl]amino}phenyl)methylidene}cyclohexa-2,5-dien-1-ylidene)(ethyl)azaniumyl]methyl}benzene-1-sulfonate Chemical compound C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S(O)(=O)=O)=C1 IHZXTIBMKNSJCJ-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
241000233866 Fungi Species 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
229920000297 Rayon Polymers 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000002411 adverse Effects 0.000 description 1
239000003899 bactericide agent Substances 0.000 description 1
239000003139 biocide Substances 0.000 description 1
238000004061 bleaching Methods 0.000 description 1
239000007844 bleaching agent Substances 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
229940056316 d&c red no. 28 Drugs 0.000 description 1
239000011928 denatured alcohol Substances 0.000 description 1
SOROIESOUPGGFO-UHFFFAOYSA-N diazolidinylurea Chemical compound OCNC(=O)N(CO)C1N(CO)C(=O)N(CO)C1=O SOROIESOUPGGFO-UHFFFAOYSA-N 0.000 description 1
RAGZEDHHTPQLAI-UHFFFAOYSA-L disodium;2',4',5',7'-tetraiodo-3-oxospiro[2-benzofuran-1,9'-xanthene]-3',6'-diolate Chemical compound [Na+].[Na+].O1C(=O)C2=CC=CC=C2C21C1=CC(I)=C([O-])C(I)=C1OC1=C(I)C([O-])=C(I)C=C21 RAGZEDHHTPQLAI-UHFFFAOYSA-L 0.000 description 1
NRZDMKVYRRMFRR-UHFFFAOYSA-L disodium;4-[3-(diethylamino)-6-diethylazaniumylidenexanthen-9-yl]benzene-1,3-dicarboxylate;chloride Chemical compound [Na+].[Na+].[Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(C([O-])=O)C=C1C([O-])=O NRZDMKVYRRMFRR-UHFFFAOYSA-L 0.000 description 1
UKHVLWKBNNSRRR-ODZAUARKSA-M dowicil 200 Chemical compound [Cl-].C1N(C2)CN3CN2C[N+]1(C\C=C/Cl)C3 UKHVLWKBNNSRRR-ODZAUARKSA-M 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
229940057841 eosine yellowish Drugs 0.000 description 1
PASCYLAFGHJSHW-UHFFFAOYSA-N ethyl 2-[(4-methoxyphenyl)methyl]-3-(methylamino)propanoate Chemical compound CCOC(=O)C(CNC)CC1=CC=C(OC)C=C1 PASCYLAFGHJSHW-UHFFFAOYSA-N 0.000 description 1
125000005909 ethyl alcohol group Chemical group 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
229940051250 hexylene glycol Drugs 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
238000000034 method Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
JPMIIZHYYWMHDT-UHFFFAOYSA-N octhilinone Chemical compound CCCCCCCCN1SC=CC1=O JPMIIZHYYWMHDT-UHFFFAOYSA-N 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000035515 penetration Effects 0.000 description 1
229920002401 polyacrylamide Polymers 0.000 description 1
229920002239 polyacrylonitrile Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
UKHVLWKBNNSRRR-TYYBGVCCSA-M quaternium-15 Chemical compound [Cl-].C1N(C2)CN3CN2C[N+]1(C/C=C/Cl)C3 UKHVLWKBNNSRRR-TYYBGVCCSA-M 0.000 description 1
239000001044 red dye Substances 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
238000009877 rendering Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1

Landscapes

Inks, Pencil-Leads, Or Crayons (AREA)

CA 2152544 1994-10-03 1995-06-23 Compositions a changement de couleur pour surligneurs Expired - Fee Related CA2152544C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US08/317,139		1994-10-03
US08/317,139 US5492558A (en)	1992-07-31	1994-10-03	Color changing compositions for highlighters

Publications (2)

Publication Number	Publication Date
CA2152544A1 CA2152544A1 (fr)	1996-04-04
CA2152544C true CA2152544C (fr)	2000-02-01

Family

ID=23232286

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2152544 Expired - Fee Related CA2152544C (fr)	1994-10-03	1995-06-23	Compositions a changement de couleur pour surligneurs

Country Status (1)

Country	Link
CA (1)	CA2152544C (fr)

1995
- 1995-06-23 CA CA 2152544 patent/CA2152544C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2152544A1 (fr)	1996-04-04

Legal Events

Date	Code	Title	Description
1996-11-28	EEER	Examination request
2001-06-26	MKLA	Lapsed

Publication	Publication Date	Title
US5492558A (en)	1996-02-20	Color changing compositions for highlighters
US5326388A (en)	1994-07-05	Color changing compositions
US5478382A (en)	1995-12-26	Color changing compositions for use on non-porous surfaces
US5489331A (en)	1996-02-06	Color changing compositions using acids
US5486228A (en)	1996-01-23	Washable color changing compositions
US5498282A (en)	1996-03-12	Color changing pan paint compositions
US5352282A (en)	1994-10-04	Color changing compositions
US5503665A (en)	1996-04-02	Latent image compositions
US5131776A (en)	1992-07-21	Aqueous permanent coloring composition for a marker
EP0960172B1 (fr)	2006-04-12	Composition colorante lavable utile dans des marqueurs effa ables a sec
CA2292613C (fr)	2007-09-11	Composition colorante
US7455725B2 (en)	2008-11-25	Washable marker ink composition
US5698614A (en)	1997-12-16	Fluorescent ink composition for use in marking pens
CA2152544C (fr)	2000-02-01	Compositions a changement de couleur pour surligneurs
CA2152653C (fr)	1999-12-21	Compositions a changement de couleur pour utilisation sur des surfaces non poreuses
CA2152652C (fr)	2000-01-18	Substances de production d'images latentes
CA2152545C (fr)	2000-02-01	Compositions a changement de couleur comportant un acide
JPH07118588A (ja)	1995-05-09	スキンマーク用インキ
US5534587A (en)	1996-07-09	Color-changeable marking composition
US20040065226A1 (en)	2004-04-08	Coloured liquid composition for editing pen
CA2152546A1 (fr)	1996-01-06	Systeme colorant electrochromatique
JPH04248862A (ja)	1992-09-04	水性耐性着色組成物
JP2006257378A (ja)	2006-09-28	筆記具
JP3225422B2 (ja)	2001-11-05	水性インキ
JPH11310743A (ja)	1999-11-09	油性ボールペン用インキ