CA1039712A - Colorings - Google Patents
ColoringsInfo
- Publication number
- CA1039712A CA1039712A CA214,960A CA214960A CA1039712A CA 1039712 A CA1039712 A CA 1039712A CA 214960 A CA214960 A CA 214960A CA 1039712 A CA1039712 A CA 1039712A
- Authority
- CA
- Canada
- Prior art keywords
- coloring composition
- coloring
- polymer
- optically
- sulfonamido
- 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
- 238000004040 coloring Methods 0.000 title claims abstract description 45
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims abstract description 22
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 210000001035 gastrointestinal tract Anatomy 0.000 claims abstract description 11
- 235000002864 food coloring agent Nutrition 0.000 claims abstract description 10
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 5
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 5
- 229920000642 polymer Polymers 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 229940124530 sulfonamide Drugs 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 6
- 210000004877 mucosa Anatomy 0.000 claims description 5
- 150000008054 sulfonate salts Chemical class 0.000 claims description 5
- -1 polyethylene Polymers 0.000 claims description 4
- 239000012472 biological sample Substances 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 239000000523 sample Substances 0.000 claims description 2
- 150000003456 sulfonamides Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 5
- 229920006237 degradable polymer Polymers 0.000 claims 2
- 239000004698 Polyethylene Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 229920000573 polyethylene Polymers 0.000 claims 1
- 238000009877 rendering Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 4
- 238000010521 absorption reaction Methods 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 31
- 239000000047 product Substances 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 235000013305 food Nutrition 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000000975 dye Substances 0.000 description 11
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229920002125 Sokalan® Polymers 0.000 description 6
- 239000004584 polyacrylic acid Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- GRDXCFKBQWDAJH-UHFFFAOYSA-N 4-acetamidobenzenesulfonyl chloride Chemical compound CC(=O)NC1=CC=C(S(Cl)(=O)=O)C=C1 GRDXCFKBQWDAJH-UHFFFAOYSA-N 0.000 description 5
- 239000000576 food coloring agent Substances 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 235000010288 sodium nitrite Nutrition 0.000 description 5
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 5
- 230000001988 toxicity Effects 0.000 description 5
- 231100000419 toxicity Toxicity 0.000 description 5
- 125000003636 chemical group Chemical group 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- TYCNXOAPQGVAQU-UHFFFAOYSA-N 5-oxo-1-(4-sulfophenyl)-4h-pyrazole-3-carboxylic acid Chemical compound O=C1CC(C(=O)O)=NN1C1=CC=C(S(O)(=O)=O)C=C1 TYCNXOAPQGVAQU-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- OIQPTROHQCGFEF-UHFFFAOYSA-L chembl1371409 Chemical compound [Na+].[Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 OIQPTROHQCGFEF-UHFFFAOYSA-L 0.000 description 3
- 238000000502 dialysis Methods 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 2
- USWINTIHFQKJTR-UHFFFAOYSA-N 3-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(O)=CC2=C1 USWINTIHFQKJTR-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CWEKGCILYDRKNV-KPOOZVEVSA-L Orange B Chemical compound [Na+].[Na+].CCOC(=O)c1[nH]n(-c2ccc(cc2)S([O-])(=O)=O)c(=O)c1\N=N\c1ccc(c2ccccc12)S([O-])(=O)=O CWEKGCILYDRKNV-KPOOZVEVSA-L 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000005518 carboxamido group Chemical group 0.000 description 2
- 210000002421 cell wall Anatomy 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 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 2
- 235000013987 orange B Nutrition 0.000 description 2
- 229920000620 organic polymer Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 2
- 229940068984 polyvinyl alcohol Drugs 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- ZPWQALCOMQRMRK-UHFFFAOYSA-M sodium;6-hydroxynaphthalene-2-sulfonate Chemical compound [Na+].C1=C(S([O-])(=O)=O)C=CC2=CC(O)=CC=C21 ZPWQALCOMQRMRK-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
- 235000012756 tartrazine Nutrition 0.000 description 2
- UJMBCXLDXJUMFB-GLCFPVLVSA-K tartrazine Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-GLCFPVLVSA-K 0.000 description 2
- 239000004149 tartrazine Substances 0.000 description 2
- 229960000943 tartrazine Drugs 0.000 description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- QLIBJPGWWSHWBF-UHFFFAOYSA-N 2-aminoethyl methacrylate Chemical compound CC(=C)C(=O)OCCN QLIBJPGWWSHWBF-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
- OMCFQVVRMGXXAF-UHFFFAOYSA-N 4-acetamidonaphthalene-1-sulfonyl chloride Chemical compound C1=CC=C2C(NC(=O)C)=CC=C(S(Cl)(=O)=O)C2=C1 OMCFQVVRMGXXAF-UHFFFAOYSA-N 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- RZSYLLSAWYUBPE-UHFFFAOYSA-L Fast green FCF Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC(O)=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 RZSYLLSAWYUBPE-UHFFFAOYSA-L 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- 238000006923 Schmidt rearrangement reaction Methods 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 235000012735 amaranth Nutrition 0.000 description 1
- 239000004178 amaranth Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- ONTQJDKFANPPKK-UHFFFAOYSA-L chembl3185981 Chemical compound [Na+].[Na+].CC1=CC(C)=C(S([O-])(=O)=O)C=C1N=NC1=CC(S([O-])(=O)=O)=C(C=CC=C2)C2=C1O ONTQJDKFANPPKK-UHFFFAOYSA-L 0.000 description 1
- HLVXFWDLRHCZEI-UHFFFAOYSA-N chromotropic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 HLVXFWDLRHCZEI-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 229940051147 fd&c yellow no. 6 Drugs 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 231100000206 health hazard Toxicity 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
- 229940107698 malachite green Drugs 0.000 description 1
- FDZZZRQASAIRJF-UHFFFAOYSA-M malachite green Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 FDZZZRQASAIRJF-UHFFFAOYSA-M 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- 239000001048 orange dye Substances 0.000 description 1
- 239000007968 orange flavor Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 235000021067 refined food Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical group [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 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
- 239000000984 vat dye Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/40—Colouring or decolouring of foods
- A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners
- A23L5/47—Addition of dyes or pigments, e.g. in combination with optical brighteners using synthetic organic dyes or pigments not covered by groups A23L5/43 - A23L5/46
-
- 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
- Y10S534/00—Organic compounds -- part of the class 532-570 series
- Y10S534/03—Polymeric azo compounds or azo compounds containing polymeric moieties
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US420545A US3920855A (en) | 1973-11-30 | 1973-11-30 | Food containing non-toxic food coloring compositions and a process therefor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1039712A true CA1039712A (en) | 1978-10-03 |
Family
ID=23666908
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA214,960A Expired CA1039712A (en) | 1973-11-30 | 1974-11-29 | Colorings |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3920855A (enExample) |
| JP (1) | JPS5743576B2 (enExample) |
| BE (1) | BE822789A (enExample) |
| BR (1) | BR7410026A (enExample) |
| CA (1) | CA1039712A (enExample) |
| CH (1) | CH609216A5 (enExample) |
| DE (1) | DE2456356A1 (enExample) |
| FR (1) | FR2253067B1 (enExample) |
| GB (1) | GB1485846A (enExample) |
| IL (1) | IL46125A (enExample) |
| IT (1) | IT1059696B (enExample) |
| NL (1) | NL7415503A (enExample) |
| ZA (1) | ZA747496B (enExample) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4113505A (en) * | 1974-04-15 | 1978-09-12 | Dynapol | Zoned coloration |
| US4167422A (en) * | 1974-08-30 | 1979-09-11 | Dynapol | Laked high molecular weight dyes |
| US4275002A (en) * | 1974-11-04 | 1981-06-23 | Dynapol | Process for preparing polymeric colorants having a poly(vinylamine) backbone |
| US4178422A (en) * | 1975-12-08 | 1979-12-11 | Dynapol | Ethylsulfonate-alkylamine copolymers as colorant backbones |
| US4382800A (en) * | 1975-12-08 | 1983-05-10 | Dynapol | Free amine-containing polymeric dyes |
| US4096134A (en) * | 1975-12-08 | 1978-06-20 | Dynapol | Ethylsulfonate-alkylamine copolymers as colorant backbones |
| US4051138A (en) * | 1975-12-08 | 1977-09-27 | Dynapol | Water-soluble amine-linked polymeric colorants |
| US4339237A (en) * | 1975-12-08 | 1982-07-13 | Dynapol | Free amine-containing polymeric dyes |
| ZA775619B (en) * | 1976-09-27 | 1978-08-30 | Dynapol Corp | High purity polymeric water-soluble colorants and their production |
| US4189380A (en) * | 1976-11-18 | 1980-02-19 | Dynapol | Salt addition in ultrafiltration purification of solutions of polymeric colorants |
| US4225432A (en) * | 1976-11-18 | 1980-09-30 | Dynapol | Efficiency of ultrafiltration purification of solutions of polymeric colorants by inorganic base addition |
| US4169203A (en) * | 1976-11-18 | 1979-09-25 | Dynapol | Water-soluble polymeric colorants containing anionic water-solubilizing groups |
| US4250327A (en) * | 1976-12-08 | 1981-02-10 | Dynapol | Polymeric yellow colorant |
| US4196294A (en) * | 1976-12-17 | 1980-04-01 | Dynapol | Orange anthrapyridine monomeric colorants and colorant precursors |
| US4316918A (en) * | 1976-12-17 | 1982-02-23 | Dynapol | Products including edibles colored with polymeric red colors |
| US4182885A (en) * | 1976-12-17 | 1980-01-08 | Dynapol | Red colors |
| US4206240A (en) * | 1976-12-17 | 1980-06-03 | Dynapol | Polymeric aminoanthrapyridine orange colors |
| US4182612A (en) * | 1977-01-31 | 1980-01-08 | The Gillette Company | Method for dyeing human hair with cationic polymeric dyes |
| US4233328A (en) * | 1978-10-04 | 1980-11-11 | Dynapol | Edible materials colored with polymeric yellow colorant |
| US4298595A (en) * | 1978-12-20 | 1981-11-03 | Dynapol | Pharmaceutical preparations containing a polymeric agent for releasing 5-aminosalicylic acid or its salts into the gastrointestinal tract |
| US4393175A (en) * | 1981-09-09 | 1983-07-12 | Dynapol | Process for the continuous diazotization of water-soluble polymeric amines |
| US4397997A (en) * | 1981-11-04 | 1983-08-09 | Dynapol | Ultraturbulent coupling of polymeric diazonium salts |
| CH655125A5 (de) * | 1983-09-21 | 1986-03-27 | Ciba Geigy Ag | Verfahren zur herstellung von azofarbstoffpraeparaten. |
| US4554181A (en) * | 1984-05-07 | 1985-11-19 | The Mead Corporation | Ink jet recording sheet having a bicomponent cationic recording surface |
| JPS61102491A (ja) * | 1984-10-24 | 1986-05-21 | 東ソー株式会社 | 着色材およびその製造法 |
| US5549933A (en) * | 1991-03-15 | 1996-08-27 | Creative Toy Corporation | Process for painting snow |
| US5362812A (en) * | 1993-04-23 | 1994-11-08 | Minnesota Mining And Manufacturing Company | Reactive polymeric dyes |
| US5490994A (en) * | 1994-07-27 | 1996-02-13 | Kraft Foods, Inc. | Method of stabilizing the color of the disodium salt of 5,5'-indigotin disulfonic acid |
| BRPI0714338B1 (pt) * | 2006-07-18 | 2017-05-16 | Ciba Holding Inc | corantes poliméricos para cabelos, composição e método de tingimento de fibras contendo queratina |
| GB2440219A (en) * | 2007-06-29 | 2008-01-23 | Ciba Sc Holding Ag | Polymeric dye having cationic dyestuff linked to polymeric backbone |
| US8337569B2 (en) * | 2009-07-15 | 2012-12-25 | Basf Se | Polymeric hair dyes |
| CN103665934B (zh) * | 2013-11-19 | 2015-12-30 | 大连理工大学 | 一种聚乙烯胺-co-丙烯腈型自交联染料，其制备方法及应用 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2640733A (en) * | 1950-03-30 | 1953-06-02 | Westinghouse Air Brake Co | Fluid pressure brake apparatus |
| NL196245A (enExample) * | 1954-10-15 | 1900-01-01 | ||
| US3137671A (en) * | 1958-03-18 | 1964-06-16 | Ciba Ltd | Process for the production of colored polyurethane plastics |
| US3304297A (en) * | 1959-02-12 | 1967-02-14 | Ciba Ltd | Dyestuffs consisting of organic dyestuffs bound to polyhydroxylated organic polymers |
| US3108846A (en) * | 1960-01-18 | 1963-10-29 | Asahi Dyestuffs Mfg Company Lt | Dyeing process |
| US3096322A (en) * | 1960-03-14 | 1963-07-02 | Eastman Kodak Co | Aminobenzenesulfonamide azo dyes for acrylic fibers |
| NL300513A (enExample) * | 1963-05-06 | |||
| DE1256623B (de) * | 1963-08-20 | 1967-12-21 | Hoechst Ag | Verfahren zur Erzeugung von nassechten Faerbungen und Drucken auf Cellulosefasern |
| US3277075A (en) * | 1963-10-21 | 1966-10-04 | Gen Aniline & Film Corp | Dyestuffs containing hydroxyethyl-sulfonylmethyl groups |
| NL6706274A (enExample) * | 1966-05-24 | 1967-11-27 | ||
| US3507850A (en) * | 1966-05-25 | 1970-04-21 | Du Pont | Polymeric fugitive azo dyes derived from methacrylate alkyl ester,methacrylic acid and a dye monomer containing sulfonic acid groups and a methacryloyl group |
| GB1270141A (en) * | 1968-04-17 | 1972-04-12 | Ici Ltd | Coloration process |
| GB1270254A (en) * | 1968-04-17 | 1972-04-12 | Ici Ltd | New dyestuffs |
-
1973
- 1973-11-30 US US420545A patent/US3920855A/en not_active Expired - Lifetime
-
1974
- 1974-11-19 GB GB50124/74A patent/GB1485846A/en not_active Expired
- 1974-11-25 ZA ZA00747496A patent/ZA747496B/xx unknown
- 1974-11-26 IL IL46125A patent/IL46125A/en unknown
- 1974-11-28 NL NL7415503A patent/NL7415503A/xx active Search and Examination
- 1974-11-28 FR FR7439003A patent/FR2253067B1/fr not_active Expired
- 1974-11-28 DE DE19742456356 patent/DE2456356A1/de not_active Withdrawn
- 1974-11-29 BE BE151019A patent/BE822789A/xx not_active IP Right Cessation
- 1974-11-29 IT IT54312/74A patent/IT1059696B/it active
- 1974-11-29 JP JP49137614A patent/JPS5743576B2/ja not_active Expired
- 1974-11-29 CH CH1588474A patent/CH609216A5/xx not_active IP Right Cessation
- 1974-11-29 BR BR10026/74A patent/BR7410026A/pt unknown
- 1974-11-29 CA CA214,960A patent/CA1039712A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT1059696B (it) | 1982-06-21 |
| ZA747496B (en) | 1975-12-31 |
| IL46125A0 (en) | 1975-02-10 |
| FR2253067B1 (enExample) | 1978-09-22 |
| US3920855A (en) | 1975-11-18 |
| NL7415503A (nl) | 1975-06-03 |
| FR2253067A1 (enExample) | 1975-06-27 |
| BR7410026A (pt) | 1976-05-25 |
| AU7562474A (en) | 1976-05-27 |
| DE2456356A1 (de) | 1975-06-05 |
| GB1485846A (en) | 1977-09-14 |
| CH609216A5 (enExample) | 1979-02-28 |
| JPS5743576B2 (enExample) | 1982-09-16 |
| JPS5094173A (enExample) | 1975-07-26 |
| IL46125A (en) | 1977-11-30 |
| BE822789A (fr) | 1975-03-14 |
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