USRE47618E1 - Acid dye mixture - Google Patents
Acid dye mixture Download PDFInfo
- Publication number
- USRE47618E1 USRE47618E1 US15/647,821 US201715647821A USRE47618E US RE47618 E1 USRE47618 E1 US RE47618E1 US 201715647821 A US201715647821 A US 201715647821A US RE47618 E USRE47618 E US RE47618E
- Authority
- US
- United States
- Prior art keywords
- dye
- formula
- dyes
- mixture
- dyeing
- 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.)
- Active, expires
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- 239000000203 mixture Substances 0.000 title claims abstract description 88
- 239000000980 acid dye Substances 0.000 title abstract description 8
- 239000000975 dye Substances 0.000 claims abstract description 208
- 238000004043 dyeing Methods 0.000 claims abstract description 37
- 238000000034 method Methods 0.000 claims abstract description 20
- 239000004952 Polyamide Substances 0.000 claims abstract description 14
- 239000002657 fibrous material Substances 0.000 claims abstract description 14
- 229920002647 polyamide Polymers 0.000 claims abstract description 14
- 238000007639 printing Methods 0.000 claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims description 11
- 150000001340 alkali metals Chemical class 0.000 claims description 11
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 11
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052700 potassium Chemical group 0.000 claims description 3
- 239000011591 potassium Chemical group 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Chemical group 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 11
- 229910052736 halogen Inorganic materials 0.000 description 9
- 150000002367 halogens Chemical group 0.000 description 9
- 159000000000 sodium salts Chemical class 0.000 description 8
- YJKWQSBFHRHPNI-TUWPXMLJSA-N CCOC1=CC=C(/N=N/C2=C(OC)C=C(/N=N/C3=CC=CC(CS(=O)(=O)O)=C3)C=C2)C=C1.[H]N(C(C)=O)C1=C(/N=N/C2=CC=CC(CS(=O)(=O)O)=C2)C=CC(/N=N/C2=CC=C(OCC(O)CC)C=C2)=C1 Chemical compound CCOC1=CC=C(/N=N/C2=C(OC)C=C(/N=N/C3=CC=CC(CS(=O)(=O)O)=C3)C=C2)C=C1.[H]N(C(C)=O)C1=C(/N=N/C2=CC=CC(CS(=O)(=O)O)=C2)C=CC(/N=N/C2=CC=C(OCC(O)CC)C=C2)=C1 YJKWQSBFHRHPNI-TUWPXMLJSA-N 0.000 description 6
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 6
- MEAGNDRFGLJMJL-CYYJNZCTSA-N [H]N(C(C)=O)C1=CC(C(F)(F)F)=C(/N=N/C2=C3C(O)=CC(S(=O)(=O)OC)=CC3=CC=C2N)C=C1 Chemical compound [H]N(C(C)=O)C1=CC(C(F)(F)F)=C(/N=N/C2=C3C(O)=CC(S(=O)(=O)OC)=CC3=CC=C2N)C=C1 MEAGNDRFGLJMJL-CYYJNZCTSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 0 COS(=O)(=O)C1=CC2=CC=C(N)C(/N=N/C3=CC=CC=C3)=C2C(O)=C1.[1*]C.[2*]C.[3*]C Chemical compound COS(=O)(=O)C1=CC2=CC=C(N)C(/N=N/C3=CC=CC=C3)=C2C(O)=C1.[1*]C.[2*]C.[3*]C 0.000 description 5
- AYUDZQODIRATIS-NZGZJTRLSA-N CC1=C(/N=N/C2=CC=C(NC3=C([N+](=O)[O-])C=C(CS(=O)(=O)O)C=C3)C=C2)C=CC(O)=C1.CC1=NN(C2=CC=CC=C2)C(N)=C1/N=N/C1=CC(Cl)=C(CS(=O)(=O)O)C=C1Cl.COC1=CC=C(/N=N/C2=C(OC)C=C(/N=N/C3=CC=CC(CS(=O)(=O)O)=C3)C=C2)C=C1.O=S(=O)(O)CC1=CC2=C(C=C1)NC(C1=CC=CC=C1)=C2/N=N/C1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1.[H]N(C1=CC=C(N=NC2=CC=C(O)C=C2C)C=C1)C1=C([N+](=O)[O-])C=C(CS(=O)(=O)O)C=C1.[H]N(COS(=O)(=O)CC)S(=O)(=O)C1=C(Cl)C=C(/N=N/C2=C(C)NC3=C2C=CC=C3)C(Cl)=C1 Chemical compound CC1=C(/N=N/C2=CC=C(NC3=C([N+](=O)[O-])C=C(CS(=O)(=O)O)C=C3)C=C2)C=CC(O)=C1.CC1=NN(C2=CC=CC=C2)C(N)=C1/N=N/C1=CC(Cl)=C(CS(=O)(=O)O)C=C1Cl.COC1=CC=C(/N=N/C2=C(OC)C=C(/N=N/C3=CC=CC(CS(=O)(=O)O)=C3)C=C2)C=C1.O=S(=O)(O)CC1=CC2=C(C=C1)NC(C1=CC=CC=C1)=C2/N=N/C1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1.[H]N(C1=CC=C(N=NC2=CC=C(O)C=C2C)C=C1)C1=C([N+](=O)[O-])C=C(CS(=O)(=O)O)C=C1.[H]N(COS(=O)(=O)CC)S(=O)(=O)C1=C(Cl)C=C(/N=N/C2=C(C)NC3=C2C=CC=C3)C(Cl)=C1 AYUDZQODIRATIS-NZGZJTRLSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- JEZFFXBEJXHEQZ-ORCUXHIYSA-N COS(=O)(=O)C1=CC2=CC=C(N)C(/N=N/C3=C(C(F)(F)F)C=C(Cl)C=C3)=C2C(O)=C1.COS(=O)(=O)C1=CC2=CC=C(N)C(/N=N/C3=C(C(F)(F)F)C=CC=C3)=C2C(O)=C1 Chemical compound COS(=O)(=O)C1=CC2=CC=C(N)C(/N=N/C3=C(C(F)(F)F)C=C(Cl)C=C3)=C2C(O)=C1.COS(=O)(=O)C1=CC2=CC=C(N)C(/N=N/C3=C(C(F)(F)F)C=CC=C3)=C2C(O)=C1 JEZFFXBEJXHEQZ-ORCUXHIYSA-N 0.000 description 3
- YIPNYZZITPBREP-UHFFFAOYSA-N [H]N(C1=CC(NC(=O)CC)=CC=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O.[H]N(C1=CC(NC(C)=O)=CC=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O.[H]N(C1=CC(S(=O)(=O)NCCO)=C(C)C(C)=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O.[H]N(C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O)C1CCCCC1.[H]N(C1=CC=C(NC(C)=O)C=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O Chemical compound [H]N(C1=CC(NC(=O)CC)=CC=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O.[H]N(C1=CC(NC(C)=O)=CC=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O.[H]N(C1=CC(S(=O)(=O)NCCO)=C(C)C(C)=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O.[H]N(C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O)C1CCCCC1.[H]N(C1=CC=C(NC(C)=O)C=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O YIPNYZZITPBREP-UHFFFAOYSA-N 0.000 description 3
- LBBMIJJZFQCXOS-UHFFFAOYSA-N [H]N(C1=CC(NC(C)=O)=C(C)C=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O.[H]N(C1=CC=CC=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O Chemical compound [H]N(C1=CC(NC(C)=O)=C(C)C=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O.[H]N(C1=CC=CC=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O LBBMIJJZFQCXOS-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 2
- AANKTTULVRIHCK-NZGZJTRLSA-N CC1=C(/N=N/C2=CC=C(NC3=C([N+](=O)[O-])C=C(CS(=O)(=O)O)C=C3)C=C2)C=CC(O)=C1.CC1=NN(C2=CC=CC=C2)C(N)=C1/N=N/C1=CC(Cl)=C(CS(=O)(=O)O)C=C1Cl.COC1=CC=C(/N=N/C2=C(OC)C=C(/N=N/C3=CC=CC(CS(=O)(=O)O)=C3)C=C2)C=C1.O=S(=O)(O)CC1=CC2=C(C=C1)NC(C1=CC=CC=C1)=C2/N=N/C1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1.[H]N(C1=CC=C(N=NC2=CC=C(O)C=C2C)C=C1)C1=C([N+](=O)[O-])C=C(CS(=O)(=O)O)C=C1.[H]N(COS(=O)(=O)CC)SO(O)C1=C(Cl)C=C(/N=N/C2=C(\C)NC3=C2C=CC=C3)C(Cl)=C1 Chemical compound CC1=C(/N=N/C2=CC=C(NC3=C([N+](=O)[O-])C=C(CS(=O)(=O)O)C=C3)C=C2)C=CC(O)=C1.CC1=NN(C2=CC=CC=C2)C(N)=C1/N=N/C1=CC(Cl)=C(CS(=O)(=O)O)C=C1Cl.COC1=CC=C(/N=N/C2=C(OC)C=C(/N=N/C3=CC=CC(CS(=O)(=O)O)=C3)C=C2)C=C1.O=S(=O)(O)CC1=CC2=C(C=C1)NC(C1=CC=CC=C1)=C2/N=N/C1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1.[H]N(C1=CC=C(N=NC2=CC=C(O)C=C2C)C=C1)C1=C([N+](=O)[O-])C=C(CS(=O)(=O)O)C=C1.[H]N(COS(=O)(=O)CC)SO(O)C1=C(Cl)C=C(/N=N/C2=C(\C)NC3=C2C=CC=C3)C(Cl)=C1 AANKTTULVRIHCK-NZGZJTRLSA-N 0.000 description 2
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- 229920002302 Nylon 6,6 Polymers 0.000 description 2
- -1 benzoylamino, benzoylamino Chemical group 0.000 description 2
- 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 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
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- IBOYIDXBXZMYAX-XYRSVAKSSA-N CC1=NN(C2=CC=CC=C2)C(N)=C1/N=N/C1=CC(Cl)=C(CS(=O)(=O)O)C=C1Cl.COC1=CC=C(/N=N/C2=C(OC)C=C(/N=N/C3=CC=CC(CS(=O)(=O)O)=C3)C=C2)C=C1.O=S(=O)(O)CC1=CC2=C(C=C1)NC(C1=CC=CC=C1)=C2/N=N/C1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1.[H]N(COS(=O)(=O)CC)S(=O)(=O)C1=C(Cl)C=C(/N=N/C2=C(C)NC3=C2C=CC=C3)C(Cl)=C1 Chemical compound CC1=NN(C2=CC=CC=C2)C(N)=C1/N=N/C1=CC(Cl)=C(CS(=O)(=O)O)C=C1Cl.COC1=CC=C(/N=N/C2=C(OC)C=C(/N=N/C3=CC=CC(CS(=O)(=O)O)=C3)C=C2)C=C1.O=S(=O)(O)CC1=CC2=C(C=C1)NC(C1=CC=CC=C1)=C2/N=N/C1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1.[H]N(COS(=O)(=O)CC)S(=O)(=O)C1=C(Cl)C=C(/N=N/C2=C(C)NC3=C2C=CC=C3)C(Cl)=C1 IBOYIDXBXZMYAX-XYRSVAKSSA-N 0.000 description 1
- GWEJCYVUCZDOSR-OCOZRVBESA-N COS(=O)(=O)C1=CC2=CC=C(N)C(/N=N/C3=C(C(F)(F)F)C=C(Cl)C=C3)=C2C(O)=C1 Chemical compound COS(=O)(=O)C1=CC2=CC=C(N)C(/N=N/C3=C(C(F)(F)F)C=C(Cl)C=C3)=C2C(O)=C1 GWEJCYVUCZDOSR-OCOZRVBESA-N 0.000 description 1
- YTFNDKPFEJNYNP-FOPLQPDUSA-N COS(=O)(=O)C1=CC2=CC=C(N)C(/N=N/C3=C(S(=O)(=O)C4=CC=C(C)C=C4)C=CC(Cl)=C3)=C2C(O)=C1.COS(=O)(=O)C1=CC2=CC=C(N)C(/N=N/C3=C(S(=O)(=O)C4=CC=CC=C4)C=CC=C3)=C2C(O)=C1.COS(=O)(=O)C1=CC2=CC=C(N)C(/N=N/C3=C(S(=O)(=O)OC4=CC=CC=C4)C=CC=C3)=C2C(O)=C1 Chemical compound COS(=O)(=O)C1=CC2=CC=C(N)C(/N=N/C3=C(S(=O)(=O)C4=CC=C(C)C=C4)C=CC(Cl)=C3)=C2C(O)=C1.COS(=O)(=O)C1=CC2=CC=C(N)C(/N=N/C3=C(S(=O)(=O)C4=CC=CC=C4)C=CC=C3)=C2C(O)=C1.COS(=O)(=O)C1=CC2=CC=C(N)C(/N=N/C3=C(S(=O)(=O)OC4=CC=CC=C4)C=CC=C3)=C2C(O)=C1 YTFNDKPFEJNYNP-FOPLQPDUSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920001410 Microfiber Polymers 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- KKARQGQKEWVTTH-UHFFFAOYSA-N [H]N(C1=CC(NC(=O)CC)=CC=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O.[H]N(C1=CC(NC(C)=O)=C(C)C=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O.[H]N(C1=CC(S(=O)(=O)NCCO)=C(C)C(C)=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O.[H]N(C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O)C1CCCCC1.[H]N(C1=CC=CC=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O Chemical compound [H]N(C1=CC(NC(=O)CC)=CC=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O.[H]N(C1=CC(NC(C)=O)=C(C)C=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O.[H]N(C1=CC(S(=O)(=O)NCCO)=C(C)C(C)=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O.[H]N(C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O)C1CCCCC1.[H]N(C1=CC=CC=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O KKARQGQKEWVTTH-UHFFFAOYSA-N 0.000 description 1
- YFSWLSWBOPLQJT-UHFFFAOYSA-N [H]N(C1=CC(NC(C)=O)=CC=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O.[H]N(C1=CC=C(NC(C)=O)C=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O Chemical compound [H]N(C1=CC(NC(C)=O)=CC=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O.[H]N(C1=CC=C(NC(C)=O)C=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O YFSWLSWBOPLQJT-UHFFFAOYSA-N 0.000 description 1
- LNKXOVQYOBLQFV-UHFFFAOYSA-N [H]N(C1=CC(S(=O)(=O)NCCO)=C(C)C(C)=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O.[H]N(C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O)C1CCCCC1.[H]N(C1=CC=C(NC(C)=O)C=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O.[H]N(C1=CC=CC=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O Chemical compound [H]N(C1=CC(S(=O)(=O)NCCO)=C(C)C(C)=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O.[H]N(C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O)C1CCCCC1.[H]N(C1=CC=C(NC(C)=O)C=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O.[H]N(C1=CC=CC=C1)C1=CC(S(=O)(=O)OC)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O LNKXOVQYOBLQFV-UHFFFAOYSA-N 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 238000010014 continuous dyeing Methods 0.000 description 1
- 238000010016 exhaust dyeing Methods 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003658 microfiber Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 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 description 1
- 239000001048 orange dye Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000001043 yellow dye Substances 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
-
- 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
- D06P1/0096—Multicolour dyeing
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0055—Mixtures of two or more disazo dyes
-
- 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
- D06P1/02—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 azo dyes
- D06P1/04—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 azo dyes not containing metal
- D06P1/06—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 azo dyes not containing metal containing acid 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
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/021—Material containing basic nitrogen using acid dyes
-
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/06—Material containing basic nitrogen containing amide groups using acid dyes
-
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/14—Wool
- D06P3/16—Wool using acid dyes
-
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/241—Polyamides; Polyurethanes using acid dyes
Definitions
- the present invention relates to the field of acid dyes.
- Acid dyes are known and can be used for dyeing and printing of natural and synthetic polyamide fiber material.
- the present invention relates to a dye mixture comprising a dye of the formula (I)
- M is hydrogen, an alkali metal, an ammonium ion or the equivalent of an alkaline earth metal
- R 1 is hydrogen, (C 1 -C 8 )-alkyl, (C 1 -C 8 )-alkyl which is substituted by halogen, halogen, benzoylamino, benzoylamino, which is substituted in the phenyl ring by halogen, —SO 2 -phenyl, —SO 2 -phenyl, which is substituted in the phenyl ring by (C 1 -C 8 )-alkyl, —SO 2 —O-phenyl, 1-azacycloheptan-N-sulfonyl, or a group of the formula (III)
- R 4 is (C 1 -C 8 )-alkyl, (C 3 -C 8 )-cycloalkyl, phenyl or phenyl which is substituted by (C 1 -C 8 )-alkyl and R 5 is hydrogen or (C 1 -C 8 )-alkyl;
- R 2 is hydrogen, halogen, (C 1 -C 8 )-alkyl or a group of the formula (IV)
- R 6 is hydrogen, methyl or ethyl; and R 7 is (C 1 -C 6 )-alkyl, phenyl or —CO—O—(C 3 -C 8 )-cycloalkyl
- R 3 is hydrogen, halogen or (C 1 -C 8 )-alkyl
- M is hydrogen, an alkali metal, an ammonium ion or the equivalent of an alkaline earth metal
- formula (II) does not include a dye of formula (I) and
- mixtures comprising a dye of the formula (I) and a dye of the formula (II), wherein R 1 is trifluoromethyl and R 2 and R 3 are both hydrogen and a dye of the formula (II), wherein R 1 is a group of the formula (III) in which R 4 is cyclohexyl and R 5 is methyl and R 2 and R 3 are both hydrogen, are excluded and
- (C 1 -C 8 )-alkyl groups may be straight-chain or branched and are for example methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, tert.-butyl, pentyl, hexyl, heptyl or octyl.
- Preferred are (C 1 -C 4 )-alkyl groups, like methyl, ethyl, n-propyl and n-butyl.
- (C 3 -C 8 )-cycloalkyl is preferably cyclohexyl.
- Halogen is preferred fluorine, chlorine and bromine. Accordingly, a (C 1 -C 8 )-alkyl group, which is substituted by halogen is preferably substituted by fluorine, chlorine or bromine. An especially preferred (C 1 -C 8 )-alkyl group, which is substituted by halogen, is trifluoromethyl.
- Halogen standing for R 2 or R 3 is preferably fluorine, chlorine and bromine and especially preferred chlorine.
- a substituted phenyl group standing for R 4 is preferred substituted by methyl.
- M is preferably hydrogen, sodium or potassium.
- Preferred dyes of the formula (II) are the dyes of the formulae (IIa) to (IIp)
- a preferred dye mixture comprises a dye of the formula (I) and a dye of the formula (IIa) or a dye of the formula (IIm).
- Another preferred dye mixture consists of a dye of the formula (I) and a dye of the formula (IIa) or a dye of the formula (IIm).
- Still another preferred dye mixture comprises a dye of the formula (I) and at least two dyes of the formula (II), one of which is a dye of the formula (IIb).
- Still another preferred dye mixture comprises a dye of the formula (I) and a dye of the formula (IIa) and a dye of the formula (IIb) or (IIm).
- the dye mixtures according to the present invention contain the dye of the formula (I) preferably in amounts of 5 to 95% by weight and the dye or the dyes of the formula (II) preferably in amounts of 95 to 5% by weight.
- the dye mixtures according to the present invention contain the dye of the formula (I) especially preferably in amounts of 40 to 80% by weight and the dye or the dyes of the formula (II) especially preferably in amounts of 60 to 20% by weight.
- the present invention also relates to dye mixtures which comprise 90 to 99.99% by weight of a dye mixture comprising a dye of the formula (I) and at least one dye of the formula (II) and 10 to 0.01% by weight of one or more shading agents.
- Shading agents are dyes which can be used to modify the shade of the inventive dye mixtures in order to adjust it to a certain shade standard.
- Preferred shading agents are acid dyes of yellow, orange or blue color or other dyes of yellow, orange or blue color which can be used together with the inventive dye mixture.
- Especially preferred shading agents are the yellow, orange and blue dyes mentioned below.
- the present invention also relates to a process for the manufacturing of the dye mixture of the present invention, which comprises mechanical mixing of the dye of the formula (I) and the dye or the dyes of the formula (II) in the required amounts.
- the dyes of the formulae (I) and (II) are known and can be purchased at the market place or produced in line with methods known to those skilled in the art.
- the dye mixtures of the present invention are suitable for dyeing and printing of natural or synthetic polyamide fiber material by the application methods numerously described in the art for acid dyes. Therefore, the present invention also relates to a process for dyeing and printing of natural or synthetic polyamide fiber material in which a dye mixture according to the present invention is used.
- a preferred natural polyamide fiber material is wool, whereas preferred synthetic polyamide fiber materials are nylon materials, like nylon-6 and nylon-6.6.
- the inventive dye mixtures are especially suitable for combination dyeing by the trichromatic technique. According to this method, the inventive red-dyeing mixtures are used together or in mixture with suitable blue-dyeing dyes or dye mixtures and suitable yellow- or orange-dyeing dyes or dye mixtures.
- the present invention also relates to a process for trichromatic dyeing and printing of natural or synthetic polyamide fiber material in which a dye mixture according to the present invention is used, together with at least one blue-dyeing dye or dye mixture and at least one yellow- or orange-dyeing dye or dye mixture.
- Preferred blue-dyeing dyes are the dyes of the formula (IIIa)
- R 8 is methyl or ethyl and M is defined as given above.
- Preferred dyes of the formula (IIIa) are the dyes of the formulae (IIIb) and (IIIc)
- Preferred yellow- or orange-dyeing dyes are the dyes of the formulae (IVa) to (IVh)
- a preferred yellow- or orange-dyeing mixture a mixture comprising a dye of the formula (IVa) and a dye of the formula (IVi)
- the mixture comprising a dye of the formula (IVa) and a dye of the formula (IVi) contain the dye of the formula (IVa) preferably in amounts of 5 to 95% by weight and the dye of the formula (IVi) preferably in amounts of 95 to 5% by weight. Especially preferred are 40 to 60% by weight of a dye of the formula (IVa) and 60 to 40% by weight of a dye of the formula (IVi).
- the inventive dye mixture shows improved on-tone build-up in combination with a blue-dyeing dye and/or a yellow- or orange dyeing dye or dye mixture thereof.
- the present invention shows improved light fastness due to on-tone fading.
- a dye mixture comprising a dye of the formula (I) and a dye of the formula (IIa)
- 60 parts of the dye of the formula (I) in form of its sodium salt and 40 parts of the dye of the formula (IIa) in form of its sodium salt are mixed homogeneously to give 100 parts of the dye mixture which hereafter is called mixture A.
- mixture B To prepare a dye mixture comprising a dye of the formula (I) and a dye of the formula (IIm), 25 parts of the dye of the formula (I) in form of its sodium salt and 75 parts of the dye of the formula (IIm) in form of its sodium salt are mixed homogeneously to give 100 parts of the dye mixture which hereafter is called mixture B.
- a dye mixture comprising a dye of the formula (I), a dye of the formula (IIa) and a dye of the formula (IIb)
- 50 parts of the dye of the formula (I) in form of its sodium salt 40 parts of the dye of the formula (IIa) in form of its sodium salt and 10 parts of the dye of the formula (IIb) in form of its sodium salt are mixed homogeneously to give 100 parts of the dye mixture which hereafter is called mixture C.
- a nylon-6,6 material (Helanca fabric) are dyed in 200 parts of an aqueous solution containing 2 g/l ammonium acetate and having a pH-value of 5 which has been adjusted with acetic acid.
- the dyes that are used are 0.10% of the red dyeing mixture A according to Example 1, 0.15% of a orange dyeing dyestuff mixture comprising equimolar amounts of the dye of the formula (IVa) and the dye of the formula (IVi) and 0.12% of the blue-dyeing dye of the formula (IIIb), the amounts given being based on the weight of the Helanca fabric. All dyes were used in form of their sodium salts.
- the dyeing time at a temperature of 60 to 90° C. is 30 to 90 minutes. After that, the dyed nylon-6,6 fabric is removed from the liquor, rinsed and dried as usual. This gives a piece of fabric completely levelly dyed in a brown shade having no material-related streaks whatever and high light fastness properties.
- Example 4 is repeated with the difference that the dyes and dye mixtures, respectively, and the amounts given in the following table were used. All dyeings obtained were completely level and with high light fastness properties.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The present invention refers to a red-dyeing acid dye mixture comprising a dye of the formula (I)
and at least one dye of the formula (II)
a process for its manufacturing and a process for dyeing and printing of natural or synthetic polyamide fiber material in which it used.
Description
This application claims benefit under 35 U.S.C. 119(e) to Ser. No. 60/650,475, filed Feb. 7, 2005.
The present invention relates to the field of acid dyes. Acid dyes are known and can be used for dyeing and printing of natural and synthetic polyamide fiber material.
The documents U.S. Pat. No. 4,537,598, U.S. Pat. No. 5,090,964, U.S. Pat. No. 5,131,919 and U.S. Pat. No. 6,443,998 describe mixtures of red-dyeing acid dyes, which can also be used for dyeing and printing of polyamide fiber and which are suitable for combination dyeing by the trichromatic technique.
However, the known dyes and dyestuff mixtures, respectively, have some disadvantages as regards applicability in the dyehouse as well as regards fastness properties of the dyed material.
It is an object of the present invention to provide improved red-dyeing mixtures of acid dyes which are suitable for dyeing or printing of natural or synthetic polyamide fiber material from an aqueous bath and show good exhaustion especially in combination with other dyes, in particular from short liquors and have very good levelling and fastness properties especially light fastness properties.
The present invention relates to a dye mixture comprising a dye of the formula (I)
wherein M is hydrogen, an alkali metal, an ammonium ion or the equivalent of an alkaline earth metal,
and at least one dye of the formula (II)
wherein
R1 is hydrogen, (C1-C8)-alkyl, (C1-C8)-alkyl which is substituted by halogen, halogen, benzoylamino, benzoylamino, which is substituted in the phenyl ring by halogen, —SO2-phenyl, —SO2-phenyl, which is substituted in the phenyl ring by (C1-C8)-alkyl, —SO2—O-phenyl, 1-azacycloheptan-N-sulfonyl, or a group of the formula (III)
in which R4 is (C1-C8)-alkyl, (C3-C8)-cycloalkyl, phenyl or phenyl which is substituted by (C1-C8)-alkyl and R5 is hydrogen or (C1-C8)-alkyl;
R2 is hydrogen, halogen, (C1-C8)-alkyl or a group of the formula (IV)
wherein R6 is hydrogen, methyl or ethyl; and R7 is (C1-C6)-alkyl, phenyl or —CO—O—(C3-C8)-cycloalkyl
R3 is hydrogen, halogen or (C1-C8)-alkyl;
M is hydrogen, an alkali metal, an ammonium ion or the equivalent of an alkaline earth metal,
whereas formula (II) does not include a dye of formula (I) and
whereas mixtures comprising a dye of the formula (I) and a dye of the formula (II), wherein R1 is trifluoromethyl and R2 and R3 are both hydrogen and a dye of the formula (II), wherein R1 is a group of the formula (III) in which R4 is cyclohexyl and R5 is methyl and R2 and R3 are both hydrogen, are excluded and
whereas mixtures consisting of the dye of the formula (I) and a dye of the formula (II), wherein R1 is trifluoromethyl and R2 and R3 are both hydrogen, are excluded.
(C1-C8)-alkyl groups may be straight-chain or branched and are for example methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, tert.-butyl, pentyl, hexyl, heptyl or octyl. Preferred are (C1-C4)-alkyl groups, like methyl, ethyl, n-propyl and n-butyl.
(C3-C8)-cycloalkyl is preferably cyclohexyl.
Halogen is preferred fluorine, chlorine and bromine. Accordingly, a (C1-C8)-alkyl group, which is substituted by halogen is preferably substituted by fluorine, chlorine or bromine. An especially preferred (C1-C8)-alkyl group, which is substituted by halogen, is trifluoromethyl.
Halogen standing for R2 or R3 is preferably fluorine, chlorine and bromine and especially preferred chlorine.
A substituted phenyl group standing for R4 is preferred substituted by methyl.
M is preferably hydrogen, sodium or potassium.
Preferred dyes of the formula (II) are the dyes of the formulae (IIa) to (IIp)
wherein M is defined as given above.
A preferred dye mixture comprises a dye of the formula (I) and a dye of the formula (IIa) or a dye of the formula (IIm).
Another preferred dye mixture consists of a dye of the formula (I) and a dye of the formula (IIa) or a dye of the formula (IIm).
Still another preferred dye mixture comprises a dye of the formula (I) and at least two dyes of the formula (II), one of which is a dye of the formula (IIb).
Still another preferred dye mixture comprises a dye of the formula (I) and a dye of the formula (IIa) and a dye of the formula (IIb) or (IIm).
The dye mixtures according to the present invention contain the dye of the formula (I) preferably in amounts of 5 to 95% by weight and the dye or the dyes of the formula (II) preferably in amounts of 95 to 5% by weight. The dye mixtures according to the present invention contain the dye of the formula (I) especially preferably in amounts of 40 to 80% by weight and the dye or the dyes of the formula (II) especially preferably in amounts of 60 to 20% by weight.
The present invention also relates to dye mixtures which comprise 90 to 99.99% by weight of a dye mixture comprising a dye of the formula (I) and at least one dye of the formula (II) and 10 to 0.01% by weight of one or more shading agents.
Shading agents are dyes which can be used to modify the shade of the inventive dye mixtures in order to adjust it to a certain shade standard.
Preferred shading agents are acid dyes of yellow, orange or blue color or other dyes of yellow, orange or blue color which can be used together with the inventive dye mixture.
Especially preferred shading agents are the yellow, orange and blue dyes mentioned below.
The present invention also relates to a process for the manufacturing of the dye mixture of the present invention, which comprises mechanical mixing of the dye of the formula (I) and the dye or the dyes of the formula (II) in the required amounts. The dyes of the formulae (I) and (II) are known and can be purchased at the market place or produced in line with methods known to those skilled in the art.
The dye mixtures of the present invention are suitable for dyeing and printing of natural or synthetic polyamide fiber material by the application methods numerously described in the art for acid dyes. Therefore, the present invention also relates to a process for dyeing and printing of natural or synthetic polyamide fiber material in which a dye mixture according to the present invention is used.
A preferred natural polyamide fiber material is wool, whereas preferred synthetic polyamide fiber materials are nylon materials, like nylon-6 and nylon-6.6.
The inventive dye mixtures are especially suitable for combination dyeing by the trichromatic technique. According to this method, the inventive red-dyeing mixtures are used together or in mixture with suitable blue-dyeing dyes or dye mixtures and suitable yellow- or orange-dyeing dyes or dye mixtures.
Therefore, the present invention also relates to a process for trichromatic dyeing and printing of natural or synthetic polyamide fiber material in which a dye mixture according to the present invention is used, together with at least one blue-dyeing dye or dye mixture and at least one yellow- or orange-dyeing dye or dye mixture.
Preferred blue-dyeing dyes are the dyes of the formula (IIIa)
wherein R8 is methyl or ethyl and M is defined as given above.
Preferred dyes of the formula (IIIa) are the dyes of the formulae (IIIb) and (IIIc)
Other preferred blue-dyeing dyes are the dyes of the formulae (IIId) to (IIIh)
wherein M is defined as given above and mixtures of two or more dyes of the formulae (IIIa) to (IIIh).
Preferred yellow- or orange-dyeing dyes are the dyes of the formulae (IVa) to (IVh)
wherein M is defined as given above and mixtures of two or more dyes of the formulae (IVa) to (IVh).
A preferred yellow- or orange-dyeing mixture a mixture comprising a dye of the formula (IVa) and a dye of the formula (IVi)
wherein M is defined as given above.
The mixture comprising a dye of the formula (IVa) and a dye of the formula (IVi) contain the dye of the formula (IVa) preferably in amounts of 5 to 95% by weight and the dye of the formula (IVi) preferably in amounts of 95 to 5% by weight. Especially preferred are 40 to 60% by weight of a dye of the formula (IVa) and 60 to 40% by weight of a dye of the formula (IVi).
Using usual exhaust or continuous dyeing and printing techniques, which are known to a person skilled in the art, the inventive dye mixture shows improved on-tone build-up in combination with a blue-dyeing dye and/or a yellow- or orange dyeing dye or dye mixture thereof.
On critical fiber material, e.g. high-delustered, pre-heatsetted micro-fibers, the present invention shows improved light fastness due to on-tone fading.
To prepare a dye mixture comprising a dye of the formula (I) and a dye of the formula (IIa), 60 parts of the dye of the formula (I) in form of its sodium salt and 40 parts of the dye of the formula (IIa) in form of its sodium salt are mixed homogeneously to give 100 parts of the dye mixture which hereafter is called mixture A.
To prepare a dye mixture comprising a dye of the formula (I) and a dye of the formula (IIm), 25 parts of the dye of the formula (I) in form of its sodium salt and 75 parts of the dye of the formula (IIm) in form of its sodium salt are mixed homogeneously to give 100 parts of the dye mixture which hereafter is called mixture B.
To prepare a dye mixture comprising a dye of the formula (I), a dye of the formula (IIa) and a dye of the formula (IIb), 50 parts of the dye of the formula (I) in form of its sodium salt, 40 parts of the dye of the formula (IIa) in form of its sodium salt and 10 parts of the dye of the formula (IIb) in form of its sodium salt are mixed homogeneously to give 100 parts of the dye mixture which hereafter is called mixture C.
10 parts of a nylon-6,6 material (Helanca fabric) are dyed in 200 parts of an aqueous solution containing 2 g/l ammonium acetate and having a pH-value of 5 which has been adjusted with acetic acid. The dyes that are used are 0.10% of the red dyeing mixture A according to Example 1, 0.15% of a orange dyeing dyestuff mixture comprising equimolar amounts of the dye of the formula (IVa) and the dye of the formula (IVi) and 0.12% of the blue-dyeing dye of the formula (IIIb), the amounts given being based on the weight of the Helanca fabric. All dyes were used in form of their sodium salts.
The dyeing time at a temperature of 60 to 90° C. is 30 to 90 minutes. After that, the dyed nylon-6,6 fabric is removed from the liquor, rinsed and dried as usual. This gives a piece of fabric completely levelly dyed in a brown shade having no material-related streaks whatever and high light fastness properties.
Example 4 is repeated with the difference that the dyes and dye mixtures, respectively, and the amounts given in the following table were used. All dyeings obtained were completely level and with high light fastness properties.
| Example | Dyes used | Shade |
| 5 | 0.035% of an equimolar mixture of the dyes | light grey |
| of formulae (IVa) and (IVi) | ||
| 0.023% of Mixture A | ||
| 0.063% of the dye of the formula (IIIb) | ||
| 6 | 0.060% of an equimolar mixture of the dyes | olive |
| of formulae (IVa) and (IVi) | ||
| 0.005% of Mixture A | ||
| 0.075% of the dye of the formula (IIIb) | ||
| 7 | 0.021% of an equimolar mixture of the dyes | brown |
| of formulae (IVa) and (IVi) | ||
| 0.027% of Mixture A | ||
| 0.020% of the dye of the formula (IIIb) | ||
| 8 | 0.035% of an equimolar mixture of the dyes | light grey |
| of formulae (IVa) and (IVi) | ||
| 0.023% of Mixture B | ||
| 0.063% of the dye of the formula (IIIb) | ||
| 9 | 0.021% of an equimolar mixture of the dyes | brown |
| of formulae (IVa) and (IVi) | ||
| 0.027% of Mixture B | ||
| 0.020% of the dye of the formula (IIIb) | ||
| 10 | 0.035% of an equimolar mixture of the dyes | light grey |
| of formulae (IVa) and (IVi) | ||
| 0.023% of Mixture C | ||
| 0.063% of the dye of the formula (IIIb) | ||
| 11 | 0.021% of an equimolar mixture of the dyes | brown |
| of formulae (IVa) and (IVi) | ||
| 0.027% of Mixture C | ||
| 0.020% of the dye of the formula (IIIb) | ||
Claims (24)
1. A dye mixture comprising a dye of the formula (I)
wherein M is hydrogen, an alkali metal, an ammonium ion or the equivalent of an alkaline earth metal,
and at least one dye of the formula (IIa) or (IIb)
M is defined above,
and at least one dye of the formula (IIIc), (IIId), (IIIe) or (IIIg)
wherein
M is defined above.
2. The dye mixture according to claim 1 , wherein M is hydrogen, sodium or potassium.
3. A process for the manufacturing of the dye mixture according to claim 1 , which comprises mechanical mixing of the dye of the formula (I) and the dye or the dyes of the formula (IIa) or (IIb) and at a dye of the formula (IIIc), (IIId), (IIIe) or (IIIg).
4. A process for dyeing and printing of natural or synthetic polyamide fiber material which comprises applying said dye mixture according to claim 1 to said material.
5. A process for trichromatic dyeing and printing of natural or synthetic polyamide fiber material which comprises applying to said material said dye mixture according to claim 1 together with at least one blue-dyeing dye or dye mixture and at least one yellow- or orange-dyeing dye or dye mixture.
6. The process according to claim 5 , wherein a dye selected from the group consisting of the dyes of formulae (IVa) to (IVh)
wherein M is hydrogen, an alkali metal, an ammonium ion or the equivalent of an alkaline earth metal,
or mixtures of two or more dyes of the formulae (IVa) to (IVh) are used as yellow- or orange dyeing dye.
7. The process according to claim 6 , wherein a mixture of a dye of the formula (IVa) and a dye of the formula (IVi)
wherein M is hydrogen, an alkali metal, an ammonium ion or the equivalent of an alkaline earth metal,
is used as yellow or orange dyeing dye.
8. The dye mixture as claimed in claim 1 , which further comprises at least one dye selected from the group consisting of the dyes of formulae (IVa) to (IVh)
wherein M is hydrogen, an alkali metal, an ammonium ion or the equivalent of an alkaline earth metal.
9. The dye mixture as claimed in claim 8 , wherein at least one dye of the formula (IVb), (IVd), (IVe) or (IVf) is used and at least one of the dyes of the formula (IIId), (IIIe) or (IIIg) is used.
10. The dye mixture according to claim 1 , consisting of the dye of the formula (I),
the dye of the formulas (IIa) or (IIb) or the dye of formula (IIa) and (IIb) and
at least one dye of the formula (IIIc), (IIId), (IIIe) or (IIIg) and
optionally comprises at least one dye selected from the group consisting of the dyes of formulae (IVa) to (IVh)
wherein M is hydrogen, an alkali metal, an ammonium ion or the equivalent of an alkaline earth metal.
11. A dye mixture comprising a dye of the formula (I)
wherein M is hydrogen, an alkali metal, an ammonium ion or the equivalent of an alkaline earth metal,
and at least one dye of the formula (IIa) or (IIb)
M is defined above,
and at least one dye of the formula (IVb), (IVd), (IVe) or (IVf)
wherein M is defined above.
12. The dye mixture as claimed in claim 11, which further comprises at least one dye selected from the group consisting of the dyes of formulae (IIIb) to (IIIh)
wherein M is hydrogen, an alkali metal, an ammonium ion or the equivalent of an alkaline earth metal.
13. The dye mixture as claimed in claim 12, wherein a dye of the formula (IIIc), (IIId)., (IIIe) or (IIIg) is used.
14. The dye mixture according to claim 11 , wherein M is hydrogen, sodium or potassium.
15. A process for the manufacturing of the dye mixture according to claim 11 , which comprises mechanical mixing of the dye of the formula (I) and the dye or the dyes of the formula (IIa) or (IIb) and at least one dye of the formula (IVb), (IVd), (IVe) or (IVf).
16. A process for dyeing and printing of natural or synthetic polyamide fiber material which comprises applying said dye mixture according to claim 11 to said material.
17. A dye mixture consisting of a dye of the formula (I)
wherein M is hydrogen, an alkali metal, an ammonium ion or the equivalent of an alkaline earth metal,
and at least one dye of the formula (IIa) or (IIb)
M is defined above,
and only one dye selected from the group consisting of the dyes of formulae (IIIb) to (IIIh)
and optionally at least one dye selected from the group consisting of the dyes of formulae (IVa) to (IVh)
wherein M is defined above.
18. The dye mixture as claimed in claim 17 , wherein the dye of the formula dye of the formula (IIIc), (IIId), (IIIe) or (IIIg) is used.
19. The dye mixture as claimed in claim 17 , wherein the dye of the formula dye of the formula (IVb), (IVd), (IVe) or (IVf) is used.
20. A process for dyeing and printing of natural or synthetic polyamide fiber material which comprises applying said dye mixture according to claim 17 to said material.
21. A dye mixture consisting of a dye of the formula (I)
wherein M is hydrogen, an alkali metal, an ammonium ion or the equivalent of an alkaline earth metal,
and at least one dye of the formula (IIa)
M is defined above,
and only one dye selected from the group consisting of the dyes of formulae (IIIb) to (IIIh)
and optionally at least one dye selected from the group consisting of the dyes of formulae (IVa) to (IVh)
wherein M is defined above.
22. The dye mixture as claimed in claim 21, wherein the dye of the formula (IIIc), (IIId), (IIIe) or (IIIg) is used.
23. The dye mixture as claimed in claim 21, wherein the dye of the formula (IVb), (IVd), (IVe) or (IVf) is used.
24. A process for dyeing and printing of natural or synthetic polyamide fiber material which comprises applying said dye mixture according to claim 21 to said material.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15/647,821 USRE47618E1 (en) | 2005-02-07 | 2017-07-12 | Acid dye mixture |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65047505P | 2005-02-07 | 2005-02-07 | |
| US11/347,923 US8323358B2 (en) | 2005-02-07 | 2006-02-06 | Acid dye mixture |
| US15/647,821 USRE47618E1 (en) | 2005-02-07 | 2017-07-12 | Acid dye mixture |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US11/347,923 Reissue US8323358B2 (en) | 2005-02-07 | 2006-02-06 | Acid dye mixture |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| USRE47618E1 true USRE47618E1 (en) | 2019-09-24 |
Family
ID=36178003
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US11/347,923 Ceased US8323358B2 (en) | 2005-02-07 | 2006-02-06 | Acid dye mixture |
| US15/647,821 Active 2029-02-28 USRE47618E1 (en) | 2005-02-07 | 2017-07-12 | Acid dye mixture |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US11/347,923 Ceased US8323358B2 (en) | 2005-02-07 | 2006-02-06 | Acid dye mixture |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8323358B2 (en) |
| EP (1) | EP1848779A1 (en) |
| JP (1) | JP2008530261A (en) |
| KR (1) | KR101319074B1 (en) |
| CN (1) | CN101090948A (en) |
| CA (1) | CA2586610C (en) |
| TW (1) | TW200636014A (en) |
| WO (1) | WO2006082207A1 (en) |
| ZA (1) | ZA200703507B (en) |
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| US7527195B2 (en) * | 2005-04-11 | 2009-05-05 | Bill Me Later, Inc. | Method and system for risk management in a transaction |
| US20060229974A1 (en) * | 2005-04-11 | 2006-10-12 | I4 Licensing Llc | Method of extending credit to at least one consumer and method of processing a transaction between a consumer and a merchant |
| EP2251383A1 (en) * | 2009-05-14 | 2010-11-17 | Clariant International Ltd. | Organic compounds |
| CN107345081A (en) * | 2017-07-24 | 2017-11-14 | 北京泛博清洁技术研究院有限公司 | Fur recyclable dyeing phloxine compound and its synthesis and application process |
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| US6443998B1 (en) | 2000-04-14 | 2002-09-03 | Shaw Industries, Inc. | Trichromatic fiber dyeing processes and compositions thereof |
-
2006
- 2006-02-01 JP JP2007553603A patent/JP2008530261A/en not_active Withdrawn
- 2006-02-01 WO PCT/EP2006/050601 patent/WO2006082207A1/en active Application Filing
- 2006-02-01 CN CNA2006800016107A patent/CN101090948A/en active Pending
- 2006-02-01 EP EP06707962A patent/EP1848779A1/en not_active Withdrawn
- 2006-02-01 CA CA2586610A patent/CA2586610C/en not_active Expired - Fee Related
- 2006-02-01 KR KR1020077017181A patent/KR101319074B1/en not_active Expired - Fee Related
- 2006-02-03 TW TW095103785A patent/TW200636014A/en unknown
- 2006-02-06 US US11/347,923 patent/US8323358B2/en not_active Ceased
-
2007
- 2007-05-02 ZA ZA200703507A patent/ZA200703507B/en unknown
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2017
- 2017-07-12 US US15/647,821 patent/USRE47618E1/en active Active
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Also Published As
| Publication number | Publication date |
|---|---|
| CN101090948A (en) | 2007-12-19 |
| WO2006082207A1 (en) | 2006-08-10 |
| US8323358B2 (en) | 2012-12-04 |
| TW200636014A (en) | 2006-10-16 |
| CA2586610C (en) | 2013-06-25 |
| US20060174426A1 (en) | 2006-08-10 |
| ZA200703507B (en) | 2008-05-28 |
| EP1848779A1 (en) | 2007-10-31 |
| CA2586610A1 (en) | 2006-08-10 |
| KR101319074B1 (en) | 2013-10-17 |
| JP2008530261A (en) | 2008-08-07 |
| KR20070100764A (en) | 2007-10-11 |
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