CA2269700A1 - Improved substrates and colorant stabilizers - Google Patents

Improved substrates and colorant stabilizers Download PDF

Info

Publication number: CA2269700A1
Authority: CA; Canada
Prior art keywords: cyclodextrin; porphine; composition; colorant; ink set
Prior art date: 1996-11-27
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.): Abandoned

Application number

CA002269700A

Other languages

English (en)

French (fr)

Inventor

Ronald S. Nohr

John G. Macdonald

Alison S. Bagwell

Kelly D. Branham

Bruce G. Stokes

Leonid A. Turkevich

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.)

Kimberly Clark Worldwide Inc

Original Assignee

Individual

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.)

1996-11-27

Filing date

1997-11-26

Publication date

1998-06-04

1996-11-27 Priority claimed from US08/757,222 external-priority patent/US5782963A/en

1997-01-23 Priority claimed from US08/788,863 external-priority patent/US6099628A/en

1997-04-15 Priority claimed from US08/843,410 external-priority patent/US5855655A/en

1997-07-31 Priority claimed from US08/903,911 external-priority patent/US5891229A/en

1997-11-26 Application filed by Individual filed Critical Individual

1998-06-04 Publication of CA2269700A1 publication Critical patent/CA2269700A1/en

Status Abandoned legal-status Critical Current

Links

239000003086 colorant Substances 0.000 title claims abstract description 193
239000003381 stabilizer Substances 0.000 title claims abstract description 64
239000000758 substrate Substances 0.000 title abstract description 69
230000000087 stabilizing effect Effects 0.000 claims abstract description 34
238000004519 manufacturing process Methods 0.000 claims abstract description 9
239000000203 mixture Substances 0.000 claims description 132
239000000976 ink Substances 0.000 claims description 121
-1 lanthanide salt Chemical class 0.000 claims description 119
229920000858 Cyclodextrin Polymers 0.000 claims description 96
229910052751 metal Inorganic materials 0.000 claims description 75
239000002184 metal Substances 0.000 claims description 75
239000000123 paper Substances 0.000 claims description 63
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 51
JZRYQZJSTWVBBD-UHFFFAOYSA-N pentaporphyrin i Chemical compound N1C(C=C2NC(=CC3=NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 JZRYQZJSTWVBBD-UHFFFAOYSA-N 0.000 claims description 48
239000011230 binding agent Substances 0.000 claims description 47
150000003839 salts Chemical class 0.000 claims description 47
238000000034 method Methods 0.000 claims description 44
229910052747 lanthanoid Inorganic materials 0.000 claims description 37
239000001267 polyvinylpyrrolidone Substances 0.000 claims description 32
229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 32
235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 32
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 29
239000000047 product Substances 0.000 claims description 29
150000002602 lanthanoids Chemical class 0.000 claims description 26
229920002451 polyvinyl alcohol Polymers 0.000 claims description 24
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 18
229910052742 iron Inorganic materials 0.000 claims description 18
229940097362 cyclodextrins Drugs 0.000 claims description 17
239000004372 Polyvinyl alcohol Substances 0.000 claims description 15
235000019422 polyvinyl alcohol Nutrition 0.000 claims description 15
WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
239000010949 copper Chemical group 0.000 claims description 11
229910052693 Europium Inorganic materials 0.000 claims description 10
229920002125 Sokalan® Polymers 0.000 claims description 10
229910052802 copper Chemical group 0.000 claims description 10
OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 claims description 10
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 10
239000002023 wood Substances 0.000 claims description 10
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 9
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 9
235000011187 glycerol Nutrition 0.000 claims description 9
150000000918 Europium Chemical class 0.000 claims description 8
239000004698 Polyethylene Substances 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 8
HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 claims description 8
239000001768 carboxy methyl cellulose Substances 0.000 claims description 8
229910017052 cobalt Inorganic materials 0.000 claims description 8
239000010941 cobalt Chemical group 0.000 claims description 8
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical group [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 8
229920000573 polyethylene Polymers 0.000 claims description 8
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239000003139 biocide Substances 0.000 claims description 7
229910021538 borax Inorganic materials 0.000 claims description 7
235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 7
230000007797 corrosion Effects 0.000 claims description 7
238000005260 corrosion Methods 0.000 claims description 7
239000003112 inhibitor Substances 0.000 claims description 7
229910052749 magnesium Inorganic materials 0.000 claims description 7
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159000000000 sodium salts Chemical class 0.000 claims description 7
239000004328 sodium tetraborate Substances 0.000 claims description 7
235000010339 sodium tetraborate Nutrition 0.000 claims description 7
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims description 6
239000012965 benzophenone Substances 0.000 claims description 6
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 claims description 6
229910052725 zinc Inorganic materials 0.000 claims description 6
230000003115 biocidal effect Effects 0.000 claims description 5
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XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
229920002845 Poly(methacrylic acid) Chemical class 0.000 claims description 4
239000002131 composite material Substances 0.000 claims description 4
239000011521 glass Substances 0.000 claims description 4
239000004745 nonwoven fabric Substances 0.000 claims description 4
239000004753 textile Substances 0.000 claims description 4
239000002759 woven fabric Substances 0.000 claims description 4
239000008112 carboxymethyl-cellulose Substances 0.000 claims description 3
229920002401 polyacrylamide Polymers 0.000 claims description 3
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NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 claims description 3
229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 claims description 2
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 2
239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 2
229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 2
239000002202 Polyethylene glycol Substances 0.000 claims description 2
235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 2
239000001863 hydroxypropyl cellulose Substances 0.000 claims description 2
235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 2
229920001223 polyethylene glycol Polymers 0.000 claims description 2
229920002338 polyhydroxyethylmethacrylate Polymers 0.000 claims description 2
GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 claims 7
229910006069 SO3H Inorganic materials 0.000 claims 6
229940031576 hydroxypropylbetadex (0.58-0.68 ms) Drugs 0.000 claims 6
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 6
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims 2
229920000371 poly(diallyldimethylammonium chloride) polymer Polymers 0.000 claims 1
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
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SKDNDVDHYMEGNJ-VURMDHGXSA-N [(e)-2-bromo-2-nitroethenyl]benzene Chemical compound [O-][N+](=O)C(\Br)=C/C1=CC=CC=C1 SKDNDVDHYMEGNJ-VURMDHGXSA-N 0.000 description 14
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 14
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GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 12
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JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 10
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125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
238000003618 dip coating Methods 0.000 description 1
FTZLWXQKVFFWLY-UHFFFAOYSA-L disodium;2,5-dichloro-4-[3-methyl-5-oxo-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazol-1-yl]benzenesulfonate Chemical compound [Na+].[Na+].CC1=NN(C=2C(=CC(=C(Cl)C=2)S([O-])(=O)=O)Cl)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 FTZLWXQKVFFWLY-UHFFFAOYSA-L 0.000 description 1
FPVGTPBMTFTMRT-UHFFFAOYSA-L disodium;2-amino-5-[(4-sulfonatophenyl)diazenyl]benzenesulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-UHFFFAOYSA-L 0.000 description 1
238000009826 distribution Methods 0.000 description 1
KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
PPBYBJMAAYETEG-UHFFFAOYSA-N ethene;formaldehyde;urea Chemical compound C=C.O=C.NC(N)=O PPBYBJMAAYETEG-UHFFFAOYSA-N 0.000 description 1
DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 1
229920000840 ethylene tetrafluoroethylene copolymer Polymers 0.000 description 1
GAGGCOKRLXYWIV-UHFFFAOYSA-N europium(3+);trinitrate Chemical compound [Eu+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O GAGGCOKRLXYWIV-UHFFFAOYSA-N 0.000 description 1
230000005284 excitation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000001815 facial effect Effects 0.000 description 1
235000019233 fast yellow AB Nutrition 0.000 description 1
239000012467 final product Substances 0.000 description 1
GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
229920002313 fluoropolymer Polymers 0.000 description 1
DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 1
UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
238000007756 gravure coating Methods 0.000 description 1
239000010440 gypsum Substances 0.000 description 1
229910052602 gypsum Inorganic materials 0.000 description 1
RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
BQBUMJXDLQOOAJ-UHFFFAOYSA-N hexanedioic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.OC(=O)CCCCC(O)=O BQBUMJXDLQOOAJ-UHFFFAOYSA-N 0.000 description 1
KJZYNXUDTRRSPN-UHFFFAOYSA-N holmium atom Chemical compound [Ho] KJZYNXUDTRRSPN-UHFFFAOYSA-N 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
229960004657 indocyanine green Drugs 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
230000001678 irradiating effect Effects 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229910052746 lanthanum Inorganic materials 0.000 description 1
FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
239000004611 light stabiliser Substances 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
RPKCZJYDUKVMGF-UHFFFAOYSA-L lucifer yellow carbohydrazide dye Chemical compound [Li+].[Li+].[O-]S(=O)(=O)C1=CC(C(N(NC(=O)NN)C2=O)=O)=C3C2=CC(S([O-])(=O)=O)=CC3=C1N RPKCZJYDUKVMGF-UHFFFAOYSA-L 0.000 description 1
OHSVLFRHMCKCQY-UHFFFAOYSA-N lutetium atom Chemical compound [Lu] OHSVLFRHMCKCQY-UHFFFAOYSA-N 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229940002712 malachite green oxalate Drugs 0.000 description 1
NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
YYGBVRCTHASBKD-UHFFFAOYSA-M methylene green Chemical compound [Cl-].C1=CC(N(C)C)=C([N+]([O-])=O)C2=[S+]C3=CC(N(C)C)=CC=C3N=C21 YYGBVRCTHASBKD-UHFFFAOYSA-M 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000000178 monomer Substances 0.000 description 1
CNXZLZNEIYFZGU-UHFFFAOYSA-N n-(4-amino-2,5-diethoxyphenyl)benzamide Chemical compound C1=C(N)C(OCC)=CC(NC(=O)C=2C=CC=CC=2)=C1OCC CNXZLZNEIYFZGU-UHFFFAOYSA-N 0.000 description 1
QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
229920003986 novolac Polymers 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
239000011368 organic material Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000011236 particulate material Substances 0.000 description 1
239000013618 particulate matter Substances 0.000 description 1
239000001814 pectin Substances 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
230000035515 penetration Effects 0.000 description 1
239000005011 phenolic resin Substances 0.000 description 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
125000001639 phenylmethylene group Chemical group [H]C(=*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
230000000886 photobiology Effects 0.000 description 1
238000006303 photolysis reaction Methods 0.000 description 1
239000001007 phthalocyanine dye Substances 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000002985 plastic film Substances 0.000 description 1
229920006255 plastic film Polymers 0.000 description 1
229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
229920000090 poly(aryl ether) Polymers 0.000 description 1
229920001084 poly(chloroprene) Polymers 0.000 description 1
229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
229920002239 polyacrylonitrile Polymers 0.000 description 1
229920001748 polybutylene Polymers 0.000 description 1
229920000120 polyethyl acrylate Polymers 0.000 description 1
229920000139 polyethylene terephthalate Polymers 0.000 description 1
239000005020 polyethylene terephthalate Substances 0.000 description 1
229920001721 polyimide Polymers 0.000 description 1
229920000306 polymethylpentene Polymers 0.000 description 1
239000011116 polymethylpentene Substances 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
229920001955 polyphenylene ether Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920001343 polytetrafluoroethylene Polymers 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229920002620 polyvinyl fluoride Polymers 0.000 description 1
239000011148 porous material Substances 0.000 description 1
VQMWBBYLQSCNPO-UHFFFAOYSA-N promethium atom Chemical compound [Pm] VQMWBBYLQSCNPO-UHFFFAOYSA-N 0.000 description 1
239000003223 protective agent Substances 0.000 description 1
238000006862 quantum yield reaction Methods 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000012552 review Methods 0.000 description 1
238000007761 roller coating Methods 0.000 description 1
KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
229910052706 scandium Inorganic materials 0.000 description 1
SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000012216 screening Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229940047670 sodium acrylate Drugs 0.000 description 1
238000005063 solubilization Methods 0.000 description 1
230000007928 solubilization Effects 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
229920003048 styrene butadiene rubber Polymers 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
238000010345 tape casting Methods 0.000 description 1
GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
QTTDXDAWQMDLOF-UHFFFAOYSA-J tetrasodium 3-[[4-[[4-[(6-amino-1-hydroxy-3-sulfonatonaphthalen-2-yl)diazenyl]-6-sulfonatonaphthalen-1-yl]diazenyl]naphthalen-1-yl]diazenyl]naphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].Nc1ccc2c(O)c(N=Nc3ccc(N=Nc4ccc(N=Nc5cc(c6cccc(c6c5)S([O-])(=O)=O)S([O-])(=O)=O)c5ccccc45)c4ccc(cc34)S([O-])(=O)=O)c(cc2c1)S([O-])(=O)=O QTTDXDAWQMDLOF-UHFFFAOYSA-J 0.000 description 1
239000004634 thermosetting polymer Substances 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
239000001016 thiazine dye Substances 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
125000005039 triarylmethyl group Chemical group 0.000 description 1
AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
LLWJPGAKXJBKKA-UHFFFAOYSA-N victoria blue B Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)=C(C=C1)C2=CC=CC=C2C1=[NH+]C1=CC=CC=C1 LLWJPGAKXJBKKA-UHFFFAOYSA-N 0.000 description 1
ROVRRJSRRSGUOL-UHFFFAOYSA-N victoria blue bo Chemical compound [Cl-].C12=CC=CC=C2C(NCC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)=C1C=CC(=[N+](CC)CC)C=C1 ROVRRJSRRSGUOL-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920003169 water-soluble polymer Polymers 0.000 description 1
239000001018 xanthene dye Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
238000004383 yellowing Methods 0.000 description 1
NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
239000010457 zeolite Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
CMFRFQODFZBKTI-UHFFFAOYSA-L zinc;4-benzamido-2,5-diethoxybenzenediazonium;tetrachloride Chemical compound [Cl-].[Cl-].Cl[Zn]Cl.CCOC1=CC([N+]#N)=C(OCC)C=C1NC(=O)C1=CC=CC=C1.CCOC1=CC([N+]#N)=C(OCC)C=C1NC(=O)C1=CC=CC=C1 CMFRFQODFZBKTI-UHFFFAOYSA-L 0.000 description 1
OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1

Classifications

- 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
- B41M5/50—Recording sheets characterised by the coating used to improve ink, dye or pigment receptivity, e.g. for ink-jet or thermal dye transfer recording
- B41M5/52—Macromolecular coatings
- B41M5/5236—Macromolecular coatings characterised by the use of natural gums, of proteins, e.g. gelatins, or of macromolecular carbohydrates, e.g. cellulose
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/40—Ink-sets specially adapted for multi-colour inkjet printing
- 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
- B41M5/0023—Digital printing methods characterised by the inks used
- 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
- B41M5/50—Recording sheets characterised by the coating used to improve ink, dye or pigment receptivity, e.g. for ink-jet or thermal dye transfer recording
- B41M5/52—Macromolecular coatings
- 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
- B41M5/50—Recording sheets characterised by the coating used to improve ink, dye or pigment receptivity, e.g. for ink-jet or thermal dye transfer recording
- B41M5/52—Macromolecular coatings
- B41M5/5227—Macromolecular coatings characterised by organic non-macromolecular additives, e.g. UV-absorbers, plasticisers, surfactants
- 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
- B41M5/50—Recording sheets characterised by the coating used to improve ink, dye or pigment receptivity, e.g. for ink-jet or thermal dye transfer recording
- B41M5/52—Macromolecular coatings
- B41M5/5254—Macromolecular coatings characterised by the use of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers

Landscapes

Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Wood Science & Technology (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Inks, Pencil-Leads, Or Crayons (AREA)
Ink Jet Recording Methods And Recording Media Thereof (AREA)

CA002269700A 1996-11-27 1997-11-26 Improved substrates and colorant stabilizers Abandoned CA2269700A1 (en)

Applications Claiming Priority (13)

Application Number	Priority Date	Filing Date	Title
US08/757,222 US5782963A (en)	1996-03-29	1996-11-27	Colorant stabilizers
US08/788,863 US6099628A (en)	1996-03-29	1997-01-23	Colorant stabilizers
US08/843,410 US5855655A (en)	1996-03-29	1997-04-15	Colorant stabilizers
US08/903,911 US5891229A (en)	1996-03-29	1997-07-31	Colorant stabilizers
US5578597P	1997-08-15	1997-08-15
US6264397P	1997-10-22	1997-10-22
US08/903,911		1997-10-22
US60/055,785		1997-10-22
US08/843,410		1997-10-22
US08/788,863		1997-10-22
US08/757,222		1997-10-22
US60/062,643		1997-10-22
PCT/US1997/021700 WO1998023695A2 (en)	1996-11-27	1997-11-26	Improved substrates and colorant stabilizers

Publications (1)

Publication Number	Publication Date
CA2269700A1 true CA2269700A1 (en)	1998-06-04

Family

ID=27556728

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002269700A Abandoned CA2269700A1 (en)	1996-11-27	1997-11-26	Improved substrates and colorant stabilizers

Country Status (8)

Country	Link
EP (1)	EP0941293A2 (de)
JP (1)	JP2002511893A (de)
KR (1)	KR20000069137A (de)
AU (1)	AU5589698A (de)
CA (1)	CA2269700A1 (de)
PL (1)	PL336328A1 (de)
SK (1)	SK67499A3 (de)
WO (1)	WO1998023695A2 (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6399769B1 (en)	1998-01-20	2002-06-04	Kimberly-Clark Worldwide, Inc.	Method of making sulfanatophenyl substituted porphines
SK1542000A3 (en) *	1998-06-03	2001-11-06	Kimberly Clark Co	Neonanoplasts produced by microemulsion technology and inks for ink jet printing
KR20010052837A (ko) *	1998-06-15	2001-06-25	로날드 디. 맥크레이	뒤틀림방지 층이 있는 잉크 제트 인쇄성 기질
EP1144512B1 (de) *	1999-01-19	2003-04-23	Kimberly-Clark Worldwide, Inc.	Farbstoffe, farbstoffstabilisatoren, tintenzusammensetzungen und verfahren zu deren herstellung
KR100498807B1 (ko) *	2001-12-04	2005-07-01	대한민국	휘발된 청색잉크 복원제 및 이의 제조방법
JP2005162770A (ja) *	2003-11-28	2005-06-23	Canon Inc	水性インク
WO2008112993A1 (en) *	2007-03-15	2008-09-18	Ventana Medical Systems, Inc.	Stabilized hematoxylin
US9683102B2 (en) *	2014-05-05	2017-06-20	Frontier Scientific, Inc.	Photo-stable and thermally-stable dye compounds for selective blue light filtered optic

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS55113036A (en) *	1979-02-24	1980-09-01	Ricoh Co Ltd	Photosensitive and thermosensitive copying material
JPH08230313A (ja) *	1994-12-12	1996-09-10	Arkwright Inc	インクジェット媒体用ポリマーマトリックスコーティング
ES2175168T3 (es) *	1995-11-28	2002-11-16	Kimberly Clark Co	Compuestos de colorantes estabilizados por la luz.

1997
- 1997-11-26 PL PL97336328A patent/PL336328A1/xx unknown
- 1997-11-26 JP JP52484398A patent/JP2002511893A/ja active Pending
- 1997-11-26 AU AU55896/98A patent/AU5589698A/en not_active Abandoned
- 1997-11-26 KR KR1019997004634A patent/KR20000069137A/ko not_active Withdrawn
- 1997-11-26 CA CA002269700A patent/CA2269700A1/en not_active Abandoned
- 1997-11-26 WO PCT/US1997/021700 patent/WO1998023695A2/en not_active Ceased
- 1997-11-26 EP EP97952235A patent/EP0941293A2/de not_active Withdrawn
- 1997-11-26 SK SK674-99A patent/SK67499A3/sk unknown

Also Published As

Publication number	Publication date
WO1998023695A3 (en)	1998-10-01
WO1998023695A2 (en)	1998-06-04
KR20000069137A (ko)	2000-11-25
AU5589698A (en)	1998-06-22
PL336328A1 (en)	2000-06-19
JP2002511893A (ja)	2002-04-16
EP0941293A2 (de)	1999-09-15
SK67499A3 (en)	2000-07-11

Legal Events

Date	Code	Title	Description
2002-09-16	EEER	Examination request
2004-11-26	FZDE	Dead

Publication	Publication Date	Title
EP0854896B1 (de)	2002-04-03	Lichtstabilisierte fabstoffzusammensetzungen
US6168654B1 (en)	2001-01-02	Colorant stabilizers
US6168655B1 (en)	2001-01-02	Colorant stabilizers
US7030176B2 (en)	2006-04-18	Recording medium with nanoparticles and methods of making the same
US5782963A (en)	1998-07-21	Colorant stabilizers
US6503559B1 (en)	2003-01-07	Neonanoplasts and microemulsion technology for inks and ink jet printing
CA2269700A1 (en)	1998-06-04	Improved substrates and colorant stabilizers
EP1134087B1 (de)	2007-07-25	Bebilderungsverfahren und damit hergestelltes bebildertes Material
US6099628A (en)	2000-08-08	Colorant stabilizers
WO2000004104A1 (en)	2000-01-27	Improved ink jet ink compositions
MXPA00001223A (en)	2001-03-05	Neonanoplasts and microemulsion technology for inks and ink jet printing
MXPA00012458A (en)	2001-11-21	Ink-jet printable substrate with anticurl layer