CA1080225A - Process for improving the colour yield and fastness properties of dyeings produced with anionic dyes on cellulose fibre material and cationic fibre-reactive compounds - Google Patents
Process for improving the colour yield and fastness properties of dyeings produced with anionic dyes on cellulose fibre material and cationic fibre-reactive compoundsInfo
- Publication number
- CA1080225A CA1080225A CA280,493A CA280493A CA1080225A CA 1080225 A CA1080225 A CA 1080225A CA 280493 A CA280493 A CA 280493A CA 1080225 A CA1080225 A CA 1080225A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- lower alkyl
- process according
- lower alkoxy
- 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
- 238000000034 method Methods 0.000 title claims abstract description 46
- 150000001875 compounds Chemical class 0.000 title claims abstract description 33
- 238000004043 dyeing Methods 0.000 title claims abstract description 31
- 239000000463 material Substances 0.000 title claims abstract description 26
- 239000000975 dye Substances 0.000 title claims abstract description 18
- 125000000129 anionic group Chemical group 0.000 title claims abstract description 8
- 125000002091 cationic group Chemical group 0.000 title claims abstract description 8
- 229920003043 Cellulose fiber Polymers 0.000 title claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 229920002678 cellulose Polymers 0.000 claims abstract description 17
- 239000001913 cellulose Substances 0.000 claims abstract description 17
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- -1 phenoxy, phenylthio Chemical group 0.000 claims abstract description 8
- 150000001450 anions Chemical class 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 150000007524 organic acids Chemical class 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 150000001767 cationic compounds Chemical class 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
- 239000005977 Ethylene Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 4
- 125000001424 substituent group Chemical group 0.000 abstract description 3
- 125000001931 aliphatic group Chemical group 0.000 abstract description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
- 239000003795 chemical substances by application Substances 0.000 description 38
- 239000000243 solution Substances 0.000 description 35
- 239000004744 fabric Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 229920000742 Cotton Polymers 0.000 description 14
- 239000000982 direct dye Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000000985 reactive dye Substances 0.000 description 7
- 239000002985 plastic film Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 229920000297 Rayon Polymers 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000010025 steaming Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 241000083869 Polyommatus dorylas Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- YXZRCLVVNRLPTP-UHFFFAOYSA-J turquoise blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Cu+2].NC1=NC(Cl)=NC(NC=2C=C(NS(=O)(=O)C3=CC=4C(=C5NC=4NC=4[N-]C(=C6C=CC(=CC6=4)S([O-])(=O)=O)NC=4NC(=C6C=C(C=CC6=4)S([O-])(=O)=O)NC=4[N-]C(=C6C=CC(=CC6=4)S([O-])(=O)=O)N5)C=C3)C(=CC=2)S([O-])(=O)=O)=N1 YXZRCLVVNRLPTP-UHFFFAOYSA-J 0.000 description 2
- JKAPWXKZLYJQJJ-UHFFFAOYSA-N 2,4-dichloro-6-methoxy-1,3,5-triazine Chemical compound COC1=NC(Cl)=NC(Cl)=N1 JKAPWXKZLYJQJJ-UHFFFAOYSA-N 0.000 description 1
- PFMRZZXGXJJZHY-UHFFFAOYSA-N 2,4-dichloro-6-propan-2-yloxy-1,3,5-triazine Chemical compound CC(C)OC1=NC(Cl)=NC(Cl)=N1 PFMRZZXGXJJZHY-UHFFFAOYSA-N 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- MCLXKFUCPVGZEN-UHFFFAOYSA-N 4,6-dichloro-1,3,5-triazin-2-amine Chemical compound NC1=NC(Cl)=NC(Cl)=N1 MCLXKFUCPVGZEN-UHFFFAOYSA-N 0.000 description 1
- BPWSQBVQMDHRSQ-UHFFFAOYSA-N 4,6-difluoro-1,3,5-triazin-2-amine Chemical compound NC1=NC(F)=NC(F)=N1 BPWSQBVQMDHRSQ-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 240000000491 Corchorus aestuans Species 0.000 description 1
- 235000011777 Corchorus aestuans Nutrition 0.000 description 1
- 235000010862 Corchorus capsularis Nutrition 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 241001397173 Kali <angiosperm> Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- SAQSTQBVENFSKT-UHFFFAOYSA-M TCA-sodium Chemical compound [Na+].[O-]C(=O)C(Cl)(Cl)Cl SAQSTQBVENFSKT-UHFFFAOYSA-M 0.000 description 1
- 241000193803 Therea Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- FLNKWZNWHZDGRT-UHFFFAOYSA-N azane;dihydrochloride Chemical compound [NH4+].[NH4+].[Cl-].[Cl-] FLNKWZNWHZDGRT-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 244000144992 flock Species 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229940085991 phosphate ion Drugs 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
- C07D251/44—One nitrogen atom with halogen atoms attached to the two other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
- C07D251/46—One nitrogen atom with oxygen or sulfur atoms attached to the two other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/48—Two nitrogen atoms
- C07D251/50—Two nitrogen atoms with a halogen atom attached to the third ring carbon atom
-
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/655—Compounds containing ammonium groups
- D06P1/66—Compounds containing ammonium groups containing quaternary ammonium groups
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/02—After-treatment
- D06P5/04—After-treatment with organic compounds
- D06P5/06—After-treatment with organic compounds containing nitrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH767476A CH610702B (de) | 1976-06-16 | 1976-06-16 | Verfahren zur verbesserung von mit anionischen farbstoffen auf cellulosetextilmaterial erzeugten faerbungen. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1080225A true CA1080225A (en) | 1980-06-24 |
Family
ID=4328821
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA280,493A Expired CA1080225A (en) | 1976-06-16 | 1977-06-14 | Process for improving the colour yield and fastness properties of dyeings produced with anionic dyes on cellulose fibre material and cationic fibre-reactive compounds |
Country Status (11)
| Country | Link |
|---|---|
| US (3) | US4171955A (en:Method) |
| JP (2) | JPS52155285A (en:Method) |
| BE (1) | BE855699A (en:Method) |
| BR (1) | BR7703873A (en:Method) |
| CA (1) | CA1080225A (en:Method) |
| CH (1) | CH610702B (en:Method) |
| DE (2) | DE2726432A1 (en:Method) |
| ES (1) | ES459812A1 (en:Method) |
| FR (2) | FR2366405A1 (en:Method) |
| GB (2) | GB1545027A (en:Method) |
| NL (1) | NL7706656A (en:Method) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2626495A1 (de) * | 1976-06-12 | 1977-12-29 | Bayer Ag | Quartaere reaktivverbindungen |
| JPS5512826A (en) * | 1978-07-07 | 1980-01-29 | Toray Ind Inc | Production of cellulosic fiber having modified dyeability |
| JPS5576178A (en) | 1978-12-01 | 1980-06-09 | Toray Industries | Discharge style of cellulose fiber |
| DE2853881A1 (de) * | 1978-12-14 | 1980-07-03 | Bayer Ag | Quartaere reaktivverbindungen |
| DE2903133A1 (de) * | 1979-01-27 | 1980-08-07 | Bayer Ag | Quartaere reaktivverbindungen |
| DE2927520A1 (de) * | 1979-07-07 | 1981-01-15 | Bayer Ag | Basische halogentriazinylfarbstoffe sowie deren herstellung und verwendung zum faerben von cellulosehaltigen materialien |
| US4676803A (en) * | 1979-07-07 | 1987-06-30 | Bayer Aktiengesellschaft | Reactive azo dyestuffs, free from anionic groups and containing a basic group and halogenotriazinyl radical and useful for dyeing cellulose/polyester |
| US4380453A (en) * | 1980-02-06 | 1983-04-19 | Dixie Yarns, Inc. | Extraneous dye or colorant scavenging system in laundry |
| US4370443A (en) * | 1980-03-03 | 1983-01-25 | Sterling Drug Inc. | Novel polymeric compounds, processes and methods of use |
| US4314001A (en) * | 1980-03-03 | 1982-02-02 | Sterling Drug Inc. | Novel polymeric compounds, processes and methods of use |
| US4347352A (en) * | 1980-03-03 | 1982-08-31 | Sterling Drug Inc. | Novel polymeric compounds, processes and methods of use |
| US4374639A (en) * | 1980-04-03 | 1983-02-22 | Dixie Yarns, Inc. | System for preventing static electricity on laundered textile materials |
| DE3107265A1 (de) * | 1981-02-26 | 1982-09-09 | Bayer Ag, 5090 Leverkusen | Reaktivfarbstoffe, verfahren zu ihrer herstellung und ihre verwendung zum faerben oder bedrucken von fasermaterialien |
| DE3217835A1 (de) * | 1981-05-16 | 1982-12-02 | Sandoz-Patent-GmbH, 7850 Lörrach | Faerbereiprodukte und verfahren zum nachbehandeln von faerbungen |
| US4436524A (en) * | 1981-05-16 | 1984-03-13 | Sandoz Ltd. | After treating composition for direct or reactive dyeings on cellulose |
| ATE47168T1 (de) * | 1986-04-07 | 1989-10-15 | Ciba Geigy Ag | Verfahren zum endengleichen faerben von cellulosefasern. |
| US4886518A (en) * | 1987-10-01 | 1989-12-12 | Ciba-Geigy Corporation | Dyeing cellulose fibres without incurring ending with colorless pyrimidine, triazine, aromatic, furfuryl or quinolinyl compound |
| JPH0749631B2 (ja) * | 1990-10-09 | 1995-05-31 | 株式会社松井色素化学工業所 | 染色方法及び染色物 |
| US5501711A (en) * | 1994-10-26 | 1996-03-26 | Water & Oil Technologies, Inc. | Method for treatment of cellulose fabrics to improve their dyeability with reactive dyes |
| US6350872B1 (en) | 1998-10-28 | 2002-02-26 | The Virkler Company | Salt free dyeing of cellulosic fibers with anionic dyes |
| GB9910807D0 (en) * | 1999-05-10 | 1999-07-07 | Prometic Biosciences Limited | Novel detoxification agents and their use |
| EP1689929B1 (en) * | 2003-11-19 | 2012-02-15 | Huntsman Advanced Materials (Switzerland) GmbH | Method of increasing depth of shade |
| CN118908908A (zh) * | 2024-07-10 | 2024-11-08 | 深圳大学 | 一种化合物及其制备方法和应用 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2415554A (en) * | 1947-02-11 | Oh nh-cc | ||
| US3119822A (en) * | 1964-01-28 | N chi chj | ||
| US2725379A (en) * | 1955-11-29 | Triazeve pharmaceuticals | ||
| DE633691C (de) * | 1933-03-25 | 1936-08-04 | I G Farbenindustrie Akt Ges | Verfahren zur Verbesserung der Echtheitseigenschaften von Faerbungen mit substantiven Farbstoffen auf celulosehaltigen Materialien |
| DE1094699B (de) | 1957-07-12 | 1960-12-15 | Bayer Ag | Nachbehandlungsmittel fuer Faerbungen |
| US3122542A (en) * | 1959-05-06 | 1964-02-25 | Geigy Ag J R | Method for the preparation of 2, 4-diamino-6-fluoro-s-triazines |
| GB963811A (en) | 1959-11-04 | 1964-07-15 | Ici Ltd | Improvements in and relating to s-triazines and polymers thereof |
| DE1134964B (de) | 1960-03-05 | 1962-08-23 | Hoechst Ag | Verfahren zum Fixieren von Pigmenten auf Fasermaterial und Flaechengebilden |
| BE651967A (en:Method) * | 1963-01-11 | |||
| BE634515A (en:Method) * | 1962-07-19 | |||
| CH441351A (de) * | 1964-06-02 | 1967-08-15 | Geigy Ag J R | Verfahren zur Herstellung N2-substituierter 2,4,6-Triamino-1,3,5-triazine |
| CH459134A (de) * | 1964-11-13 | 1968-02-29 | Ciba Geigy | Verfahren zum optischen Aufhellen, Färben oder Bedrucken von Textilgut |
| US3632294A (en) * | 1968-11-12 | 1972-01-04 | Ciba Ltd | Quaternary nitrogen compound assisted reactive dyeing |
| US3679348A (en) * | 1969-10-14 | 1972-07-25 | Mitsui Toatsu Chemicals | Combined process for dyeing and finishing fabrics composed of cellulosic fibers |
-
1976
- 1976-06-16 CH CH767476A patent/CH610702B/xx not_active IP Right Cessation
-
1977
- 1977-06-09 US US05/805,069 patent/US4171955A/en not_active Expired - Lifetime
- 1977-06-09 US US05/805,208 patent/US4180664A/en not_active Expired - Lifetime
- 1977-06-11 DE DE19772726432 patent/DE2726432A1/de not_active Withdrawn
- 1977-06-11 DE DE19772726433 patent/DE2726433A1/de not_active Withdrawn
- 1977-06-14 CA CA280,493A patent/CA1080225A/en not_active Expired
- 1977-06-15 BR BR7703873A patent/BR7703873A/pt unknown
- 1977-06-15 GB GB25069/77A patent/GB1545027A/en not_active Expired
- 1977-06-15 GB GB25070/77A patent/GB1550716A/en not_active Expired
- 1977-06-15 JP JP7005977A patent/JPS52155285A/ja active Pending
- 1977-06-15 FR FR7718405A patent/FR2366405A1/fr active Granted
- 1977-06-15 JP JP7006077A patent/JPS52155286A/ja active Pending
- 1977-06-15 BE BE178451A patent/BE855699A/xx unknown
- 1977-06-15 FR FR7718404A patent/FR2366404A1/fr active Granted
- 1977-06-15 ES ES459812A patent/ES459812A1/es not_active Expired
- 1977-06-16 NL NL7706656A patent/NL7706656A/xx not_active Application Discontinuation
-
1979
- 1979-07-16 US US06/058,045 patent/US4246670A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR2366405B1 (en:Method) | 1979-06-01 |
| GB1550716A (en) | 1979-08-15 |
| BE855699A (fr) | 1977-12-15 |
| US4246670A (en) | 1981-01-27 |
| FR2366405A1 (fr) | 1978-04-28 |
| ES459812A1 (es) | 1978-07-16 |
| BR7703873A (pt) | 1978-04-25 |
| CH610702B (de) | |
| CH610702GA3 (en:Method) | 1979-05-15 |
| DE2726432A1 (de) | 1977-12-29 |
| US4180664A (en) | 1979-12-25 |
| FR2366404B1 (en:Method) | 1980-07-18 |
| JPS52155285A (en) | 1977-12-23 |
| DE2726433A1 (de) | 1977-12-29 |
| US4171955A (en) | 1979-10-23 |
| FR2366404A1 (fr) | 1978-04-28 |
| GB1545027A (en) | 1979-05-02 |
| JPS52155286A (en) | 1977-12-23 |
| NL7706656A (nl) | 1978-01-18 |
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