US2004476A - Dyeing of textiles - Google Patents
Dyeing of textiles Download PDFInfo
- Publication number
- US2004476A US2004476A US568870A US56887031A US2004476A US 2004476 A US2004476 A US 2004476A US 568870 A US568870 A US 568870A US 56887031 A US56887031 A US 56887031A US 2004476 A US2004476 A US 2004476A
- Authority
- US
- United States
- Prior art keywords
- water
- dyed
- dyeing
- fastness
- formula
- 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 - Lifetime
Links
- 238000004043 dyeing Methods 0.000 title description 24
- 239000004753 textile Substances 0.000 title description 23
- 239000000463 material Substances 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 150000003839 salts Chemical class 0.000 description 16
- 238000000034 method Methods 0.000 description 14
- 229920000742 Cotton Polymers 0.000 description 12
- 238000009967 direct dyeing Methods 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 125000001931 aliphatic group Chemical group 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000004627 regenerated cellulose Substances 0.000 description 9
- -1 aliphatic amines Chemical class 0.000 description 8
- 150000007530 organic bases Chemical class 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- ITFGZZGYXVHOOU-UHFFFAOYSA-N n,n-dimethylmethanamine;methyl hydrogen sulfate Chemical compound C[NH+](C)C.COS([O-])(=O)=O ITFGZZGYXVHOOU-UHFFFAOYSA-N 0.000 description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 6
- 239000013589 supplement Substances 0.000 description 6
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 229920000768 polyamine Polymers 0.000 description 5
- NEAVWSTWAPWAPP-KTKRTIGZSA-N (z)-n-(2-aminoethyl)octadec-9-enamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)NCCN NEAVWSTWAPWAPP-KTKRTIGZSA-N 0.000 description 4
- 229920000297 Rayon Polymers 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- 239000010446 mirabilite Substances 0.000 description 4
- LHYQAEFVHIZFLR-UHFFFAOYSA-L 4-(4-diazonio-3-methoxyphenyl)-2-methoxybenzenediazonium;dichloride Chemical compound [Cl-].[Cl-].C1=C([N+]#N)C(OC)=CC(C=2C=C(OC)C([N+]#N)=CC=2)=C1 LHYQAEFVHIZFLR-UHFFFAOYSA-L 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 150000003868 ammonium compounds Chemical class 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- IPCSVZSSVZVIGE-UHFFFAOYSA-N n-hexadecanoic acid Natural products CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 229960002969 oleic acid Drugs 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- ZRQWXZLJRJZNJO-UHFFFAOYSA-M 2-pyridin-1-ium-1-ylethanol;chloride Chemical compound [Cl-].OCC[N+]1=CC=CC=C1 ZRQWXZLJRJZNJO-UHFFFAOYSA-M 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- 229920002955 Art silk Polymers 0.000 description 2
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 2
- 239000005639 Lauric acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 235000021313 oleic acid Nutrition 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- RYHIOFLTIJFRDZ-UHFFFAOYSA-M pyridin-1-ium-1-ylmethanol;chloride Chemical compound [Cl-].OC[N+]1=CC=CC=C1 RYHIOFLTIJFRDZ-UHFFFAOYSA-M 0.000 description 2
- 229940001593 sodium carbonate Drugs 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 description 2
- 238000009969 top dyeing Methods 0.000 description 2
- KCRWDYKXVMAHPD-UHFFFAOYSA-N (5-methyl-2-propan-2-ylcyclohexyl) N-[2-(diethylamino)ethyl]-N-(5-methyl-2-propan-2-ylcyclohexyl)oxycarbonylcarbamate Chemical compound C1(CC(C(CC1)C(C)C)OC(=O)N(C(=O)OC1CC(CCC1C(C)C)C)CCN(CC)CC)C KCRWDYKXVMAHPD-UHFFFAOYSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 description 1
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
- 240000008564 Boehmeria nivea Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000488484 Craugastor andi Species 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 240000002989 Euphorbia neriifolia Species 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- MRQIXHXHHPWVIL-ISLYRVAYSA-N Sudan I Chemical compound OC1=CC=C2C=CC=CC2=C1\N=N\C1=CC=CC=C1 MRQIXHXHHPWVIL-ISLYRVAYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- BPHHNXJPFPEJOF-UHFFFAOYSA-J chembl296966 Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC(S([O-])(=O)=O)=C(N)C2=C(O)C(N=NC3=CC=C(C=C3OC)C=3C=C(C(=CC=3)N=NC=3C(=C4C(N)=C(C=C(C4=CC=3)S([O-])(=O)=O)S([O-])(=O)=O)O)OC)=CC=C21 BPHHNXJPFPEJOF-UHFFFAOYSA-J 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- ALSTYHKOOCGGFT-UHFFFAOYSA-N cis-oleyl alcohol Natural products CCCCCCCCC=CCCCCCCCCO ALSTYHKOOCGGFT-UHFFFAOYSA-N 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
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LRFIFBMQILCQBA-UHFFFAOYSA-N diethyl(hexadecyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[NH+](CC)CC LRFIFBMQILCQBA-UHFFFAOYSA-N 0.000 description 1
- LARMRMCFZNGNNX-UHFFFAOYSA-L disodium 7-anilino-3-[[4-[(2,4-dimethyl-6-sulfonatophenyl)diazenyl]-2-methoxy-5-methylphenyl]diazenyl]-4-hydroxynaphthalene-2-sulfonate Chemical compound [Na+].[Na+].COc1cc(N=Nc2c(C)cc(C)cc2S([O-])(=O)=O)c(C)cc1N=Nc1c(O)c2ccc(Nc3ccccc3)cc2cc1S([O-])(=O)=O LARMRMCFZNGNNX-UHFFFAOYSA-L 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- SOIFEMDRPRPHQJ-UHFFFAOYSA-N ethyl N-[3-(dimethylamino)phenyl]-N-hexadecylcarbamate Chemical compound CN(C=1C=C(C=CC1)N(C(=O)OCC)CCCCCCCCCCCCCCCC)C SOIFEMDRPRPHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- CNXZLZNEIYFZGU-UHFFFAOYSA-N n-(4-amino-2,5-diethoxyphenyl)benzamide Chemical compound C1=C(N)C(OCC)=CC(NC(=O)C=2C=CC=CC=2)=C1OCC CNXZLZNEIYFZGU-UHFFFAOYSA-N 0.000 description 1
- GVIGJCUYKKEYAL-UHFFFAOYSA-N n-(4-aminophenyl)octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NC1=CC=C(N)C=C1 GVIGJCUYKKEYAL-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([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
- 125000000913 palmityl 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])C([H])([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
- 235000012736 patent blue V Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- OARRHUQTFTUEOS-UHFFFAOYSA-N safranin Chemical compound [Cl-].C=12C=C(N)C(C)=CC2=NC2=CC(C)=C(N)C=C2[N+]=1C1=CC=CC=C1 OARRHUQTFTUEOS-UHFFFAOYSA-N 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- UAWGEYZZCKAPHY-XBFRWELRSA-N sodium;5-[(4-ethoxyphenyl)diazenyl]-2-[(e)-2-[4-[(4-ethoxyphenyl)diazenyl]-2-sulfophenyl]ethenyl]benzenesulfonic acid Chemical compound [Na+].C1=CC(OCC)=CC=C1N=NC(C=C1S(O)(=O)=O)=CC=C1\C=C\C1=CC=C(N=NC=2C=CC(OCC)=CC=2)C=C1S(O)(=O)=O UAWGEYZZCKAPHY-XBFRWELRSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([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
- 239000000126 substance Substances 0.000 description 1
- 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 1
- 235000012756 tartrazine Nutrition 0.000 description 1
- 229960000943 tartrazine Drugs 0.000 description 1
- 239000004149 tartrazine Substances 0.000 description 1
- HHADJUZGKVNYLU-UHFFFAOYSA-M trimethyl(2-octadecanoyloxyethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC(=O)OCC[N+](C)(C)C HHADJUZGKVNYLU-UHFFFAOYSA-M 0.000 description 1
- FKVXIGHJGBQFIH-UHFFFAOYSA-K trisodium 5-amino-3-[[4-[4-[(7-amino-1-hydroxy-3-sulfonatonaphthalen-2-yl)diazenyl]phenyl]phenyl]diazenyl]-4-hydroxynaphthalene-2,7-disulfonate Chemical compound C1=CC(=CC=C1C2=CC=C(C=C2)N=NC3=C(C=C4C=CC(=CC4=C3[O-])N)S(=O)(=O)O)N=NC5=C(C6=C(C=C(C=C6C=C5S(=O)(=O)O)S(=O)(=O)[O-])N)[O-].[Na+].[Na+].[Na+] FKVXIGHJGBQFIH-UHFFFAOYSA-K 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 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
- 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
- D06P1/64—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 using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/645—Aliphatic, araliphatic or cycloaliphatic compounds containing amino 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
- 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
- D06P1/64—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 using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/649—Compounds containing carbonamide, thiocarbonamide or guanyl groups
- D06P1/6495—Compounds containing carbonamide -RCON= (R=H or hydrocarbons)
- D06P1/6497—Amides of di- or polyamines; Acylated polyamines
-
- 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
-
- 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
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/03—Organic sulfoxy compound containing
- Y10S516/05—Organic amine, amide, or n-base containing
-
- 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
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/916—Natural fiber dyeing
- Y10S8/918—Cellulose textile
Definitions
- the fastness to water and to wet ironing, of dyeings obtained with such dyestuffs, and in many cases the fastness to top dyeing with such dyestuffs is quite generally improved by an after-treatment with water-soluble salts of organic bases which are characterized by their containing, on the one part, at least one basic nitrogen-containing residue x, and, on the other part, at least one aliphatic residue R consisting of ,at least 10 carbon atoms.
- Such products correspond for example to the general formula wherein at stands for the residue of an organic base, 0 means a bridge consisting of an oxygen atom, and R stands for an aliphatic residue consisting of at least 10 carbon atoms.
- Such compounds are for example the mixed ethers from cetylalcohol and N-hydroxymethylpyridinium chloride of the formula oi-n-onr-o-cnnn I no or: at tin the stearic acid dimethyl or diethylaminoethanolester hydrochloride of the formula H (;JH
- no on the hydrochloride of the diethylaminoethyloctodecyl carbonate of the formula 11 can n-om-cm-o-o-o onnu I the stearyl ester of the addition product of the glycerinemono-chlorhydrine or of the and-glycerinedichlorhydrine to pyridine of the formulas.
- the stearoyl or the palmitoyl residue may be replaced by the residues of other acids such as oleicacid, capric acid, lauric acid, myristic acid or ricinoleic acid.
- the alcoholic residue such as the residue of the cetyl alcohol, may be replaced by the alcoholic residues which correspond to the above named acids, such as oleic alcohol etc.
- partially acylated polyamines are for example such which derive from diamines containing OH-groups, for example the hydrochloride of oleoyl-p-hydroxy- 'y-diethylamino-propyl-amide of the formula (cf. Patent 1,805,355, Example 1) and the ammonium compounds thereof, such as I 1 1 Ocm-n-cr'a-on-cm-rm-o o-c a CK 6,11.
- Such acylated polyamines may further be produced by .partially acylating compounds, such as diethyl'enetriamine, triethylenetetramine, NHzCH2-CH2NH-CH2CH2 NHa, NH2-CHrCHzNH-CH2CH2NH- CH2-CH2NH2, etc., and other similar compounds, and their .alkylation or varalkylation products, or the ammonium compounds thereof.
- .partially acylating compounds such as diethyl'enetriamine, triethylenetetramine, NHzCH2-CH2NH-CH2CH2 NHa, NH2-CHrCHzNH-CH2CH2NH- CH2-CH2NH2, etc.
- the improvement in the fastness to water is not limited to direct dyeings, but it is to ,be observed also in the case or dyeings which are subsequently developed, for instance by after-treatment with formaldehyde, or by diazotization and coupling on the fibre.
- the invention opens the door for the use'of direct dyestufls for dyeing hat bands, umbrella silks, batique goods, half-wool goods or half-' silk goods which must be dyed by the two-bath process, namely first with the direct dyestufl' and then as a top dyeing with an acid dyestufl in an acid bath, and also to other applications of such dyestuffs, the improvement constituting a considerable industrial advance.
- this expression comprising'textiles from natural cellulose, such as cotton, ramie, linen, iute etc., or from regenerated cellulose, such as so-called viscose silk or cuprammonium silk, be improved by this invention, but similar effects can be produced on other materials, such as-paper or wood. More or less pronounced eifects can also be obtained on other textiles or other materials, such as wool and acetate silk, even ifthey have been dyed with dyestufls other than direct dyeing dyestuffs, for example acid dyestufls.
- the aftertreatment of the dyed material may occur during any of the operations which follow dyeing, for example, in the finishing operation, the watersoluble salts of the bases containing the above mentioned residues 2: and B being added to the appropriate treatment bath.
- Example 1 100 kilos of cotton yarn are dyed with 2 kilos of Cotton yellow CH (Schultz 1923,
- kilos of viscose tricot are dyed in the usual manner at boiling temperature with 0.2 kilo of Chlorantine red 8BN (Schultz 1923,
- Example 3 Cotton piece goods which have been dyed as usual with 2 per cent. ofDirect sky blue green shade (Schultz 1923, No. 424) are after-treated in a fresh bath with a solution of 1 per cent. (calculated on the weight of the goods) of the -oleic acid ester of the hydroxy-ethylpyridinium chloride and dried, the operation being as indicated in Example 2.
- the dyed material is fas towards water.
- Example 4 50 kilos of cotton yarn are dyed with 1.5 kilos of Direct Saframine RW (Color Index Supplement 1928, P e 39) 1000 litres of water,
- Example 5 Bleached cotton material is dyed in a neutral rinsed and dried.
- Example 6 A mixed fabric of viscose artificial silk and cotton is dyed in the usual manner in a bath containing Glauber's salt with 2.5 per cent. of Rigan blue (3- (Melliands Textil-Berichte 1930, page 642) for one hour at 70-80 C. andis then after-treated in a further bath with 1 per cent. of the acetate of oleoyl-p-hydroxy-y-diethylamino-propylam'lde (cf. specification 1,805,355, Example 1), as
- Example 7 100 kilos of viscose thread are dyed for one hour at 80 C. with 6 kilos of Melantherine BH (Color Index No. 401), 1 kilo of crystallized sodium car-- bonate and 40 kilos of crystallized sodium sulfate.
- Example 8 10 kilos ofhalf-silk ribbon (cotton and silk) are dyed with 0.25 kilo of Chlorantine fast brown BBL (Color Index Supplement, pa e 31), 0.150 kilo of Chlorantine fast blue 8GL (Color Index Supplement, page 31) 0.100 kilo of Diamine fast orange R (Color Index, page 349) 0.2 kilo of marseilles soap and 4 kilos of crystallized sodium sulfate in 400 litres of water atapproximately boiling point for one hour.
- Example 4 After thorough rinsing the goods are after-treated as described in Example 4 in a liquor which contains 0.06 kilo of the acetate of mono-oleoyl-diethyl-ethylenediamine (cf. specification 1,534,525, Example 9) in 200 litres of 4 water. In this case also there isan essential improvement in the fastness to water.
- Example 9 In half-wool the cotton is dyed as usual with 3 per cent. of Chlorantine fast blue GLN (Color Index Supplement, page 31), then rinsed and Example 10 nan-won material is first dyed in an acid bath in the usual manner with l per cent. of Tartrazine (Color Index No. 640). It is then well rinsed, and
- the cotton is dyed at 55 C. with 3 per cent. of Direct sky blue green shade (Color Index No. 518) with or without addition of a reserving agent,
- the half-wool material which has thus been dyed in a two-color effect is rinsed and then water.
- Direct Safranine B (Color Index, page 351) is discharged in the known manner by means of sodium sulfoxylate, and then passed through the aforesaid trimethylammonium-methylsulfate solution, the velvet may be allowed to remain overnight in luke warm water without fear that the color will run.
- a likeresult is obtained if the treatment with the trimethylanunonium methylsulfate of monooleoylethylenediamine is interposed between the dyeing and printing operations.
- Chlorantine fast blue RL (Color Index, page 345) 670 grams of water 300 grams of solid British gum 20 grams of sodium phosphate 7 1000 grams
- the material is steamed twice in a quick steamer or for half an hour in a vessel at ordinary pressure. It is then passed through a bath containing per litre 0.3 gram of oleoylaminoethyl-diethylmethylammoniumsulfomethylate (of. Patent 1,737,458, Example 2), rinsed and dried. There is obtained a blue print of good fastness to water.
- acylated diamines used in the foregoing example are replaced by others, such as the trimethylammonium-methyl sulfate of monostearoyl metaphenylenediamine (of. German Patent 559,500); the addition product of dimethyl sulfate and ortho-, meta or para-dimethylaminophenylcarbamic acid hexadecyl or octodecyl ester; the hydrochloride of diethylaminoethylimino-dicarboxylic acid dimenthyl ester (cf. Patent 1,527,868, Example 4) or the corresponding addition product with dimethyl sulfate; and the .like.
- others such as the trimethylammonium-methyl sulfate of monostearoyl metaphenylenediamine (of. German Patent 559,500); the addition product of dimethyl sulfate and ortho-, meta or para-dimethylaminophenylcarbamic acid hexadec
- Example 13 Silk paper is dyed by the immersion process by padding with a dyestufi solution containing 10 grams of Direct Sairanine B (Golor Index, page 351) per litre. It is then treated, either after drying or without drying, in a bath containing 1 gram of ole-oylaminoethyl-diethylmethylammoniumsulfomethylate (of. Patent 1,737,458, Example 2) per litre. The material is thus dyed a red shade which is fast to water. If instead of Direct $afranine B there is used in the process of this example Kiton blue A (Color Index Supplement, page 44) there is obtained a blue dyeing fast to water.
- Kiton blue A Color Index Supplement
- Example 14 Loaded silk piece goods are dyed for hour at C. with 215 per cent of Alizarin Fast blue BB (Color Index Supplement, page 26) and 4 per cent of acetic acid. They are then rinsed in cold water and after-treated for 20 minutes at ill-45 C. with l per cent of the trimethylammoniummethylsulfate of mono-oleoylethylenediamine. The blue dyeing is rendered essentially faster towards water by the after-treatment.
- Alizarin Fast blue BB Color Index Supplement, page 26
- a process for improving the fastness of dyeings produced onmaterials by means of watersoluble dyestuffs which consists in subjecting the dyed material to an after-treatment with watersoluble salts of organic bases which bases are characterized by containing at least one basic nitrogen-containing residue and an aliphatic residue consisting ofat least 10 carbon atoms.
- a process for improving. the fastness of dyeings produed on textile materials by means of water-soluble dyestuifs which consists in subjecting the dyed material to an after-treatment with water-soluble salts of organic bases'which bases are characterized by containing at least one basic nitrogen-containing residue and an aliphatic residue consisting of at least 10 carbon atoms.
- a process for improving the fastness of dyeings produced on textile materials by means of water-soluble dyestuffs which consists in subjecting the textile material dyed with direct dyeing dyestufis to an after-treatment with watersoluble salts of organic bases which bases are characterized by containing at least one basic nitrogen-containing residue and'an aliphatic residue consisting of at least 10 carbon atoms.
- a process for improving the fastness of dyeings produced on textile materials by means oi? water-soluble. dyestuffs which consists in subjecting the textile material dyed with direct dyeing dyestuiis to an after-treatment with waterso-luble salts of organic bases which bases are characterized by containing at least one basic nitrogen-containing residue and an aliphatic residue consisting of at least 12 carbon atoms,
- water-soluble direct dyeing dyestuffs which consists in subjecting the cellulosic textile material dyed with direct dyeing dyestuffs to an after-treatment with water-soluble salts of organic bases which bases are characterized by containing at least one 6.
- a process for improving the iastness o! dyeings produced on cellulosic textile materials selected from the group consisting oi native and regenerated cellulose by means of water-soluble dyestuffs which consists in subjecting the cellulosic textile materials dyed with direct dyeing dyestufis to an after-treatment with a watersoluble salt of the formula 8.
- a process for improving the fastness of dyeings produced on cellulosic textile materials' selected from the group consisting of native and regenerated cellulose by means of water-soluble dyestuffs which consists in subjecting the cellulosic textile materials dyed with direct dyeing dyestuffs to an after-treatment with a water-soluble salt of the general formula in which 2: stands for the residue of an organic base, constitutes a bridge consisting of an oxygen atom, and R stands for an aliphatic residue containing at least 12 carbon atoms.
- a process 'for improving the fastness oi dyeings produced on cellulosic textile materials selected from the group consisting of native and regenerated cellulose by means of water-soluble dyestuffs which consists in subjecting the cellulosic textile materials dyed with direct dyeing dyestufis to an after-treatment with a water-soluble salt of the formula HANS KAEGI. CHARLES GRAENACI-IER.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH2004476X | 1930-10-16 | ||
GB33189/30A GB366918A (en) | 1930-10-16 | 1930-11-04 | Improvements in the dyeing of textiles |
Publications (1)
Publication Number | Publication Date |
---|---|
US2004476A true US2004476A (en) | 1935-06-11 |
Family
ID=32471171
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US568870A Expired - Lifetime US2004476A (en) | 1930-10-16 | 1931-10-14 | Dyeing of textiles |
Country Status (6)
Country | Link |
---|---|
US (1) | US2004476A (en(2012)) |
BE (1) | BE390553A (en(2012)) |
DE (1) | DE582101C (en(2012)) |
FR (1) | FR725637A (en(2012)) |
GB (1) | GB366918A (en(2012)) |
NL (1) | NL30888C (en(2012)) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2449926A (en) * | 1941-08-29 | 1948-09-21 | Emulsol Corp | Esters of alcohol nontertiary amines |
US2481692A (en) * | 1944-04-12 | 1949-09-13 | Rayonier Inc | Cotton treated with a cation active amine |
US2861863A (en) * | 1952-12-19 | 1958-11-25 | Basf Ag | Improvement of fastness of cellulosic fibers with a polymerization product of basic vinyl compounds |
US2950217A (en) * | 1956-11-13 | 1960-08-23 | Du Pont | Impregnation process |
DE2121013A1 (de) * | 1971-04-29 | 1972-11-23 | Bayer Ag, 5090 Leverkusen | Quaternäre Ammoniumverbindungen |
US4001285A (en) * | 1971-07-27 | 1977-01-04 | Sandoz Ltd. | Amidopolyaminesulfonates |
US4247295A (en) * | 1979-05-14 | 1981-01-27 | Estampados Estil, S.A. | Discharge printing of textiles dyed with indigo blue |
US4436521A (en) | 1979-10-18 | 1984-03-13 | Sandoz Ltd. | Process for producing dyed and anti-shrink treated wool |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE763183C (de) * | 1937-07-03 | 1952-11-17 | Ig Farbenindustrie Ag | Verfahren zur Verbesserung der Echtheitseigenschaften von Direktfaerbungen |
DE751174C (de) * | 1937-07-03 | 1952-08-28 | Ig Farbenindustrie Ag | Verfahren zur Verbesserung der Echtheitseigenschaften von Direktfaerbungen |
DE958379C (de) * | 1943-04-09 | 1957-02-21 | Cassella Farbwerke Mainkur Ag | Verfahren zur Verbesserung der Echtheitseigenschaften von Faerbungen mit substantiven Farbstoffen auf Cellulosefasern |
US4424061A (en) * | 1981-02-27 | 1984-01-03 | Dainippon Pharmaceutical Co., Ltd. | Color fastness of dyed cotton textiles to chlorinated water and process for improving the color fastness of dyed cotton textiles to chlorinated water |
US4728337A (en) * | 1985-11-08 | 1988-03-01 | Ciba-Geigy Corporation | Assistant combination and use thereof as wool textile finishing agent |
US4721512A (en) * | 1985-11-25 | 1988-01-26 | Ciba-Geigy Corporation | Process for aftertreating dyed cellulosic material |
-
1930
- 1930-10-19 DE DE1930G0007830 patent/DE582101C/de not_active Expired
- 1930-11-04 GB GB33189/30A patent/GB366918A/en not_active Expired
-
1931
- 1931-10-13 NL NL58764A patent/NL30888C/xx active
- 1931-10-14 US US568870A patent/US2004476A/en not_active Expired - Lifetime
- 1931-10-16 FR FR725637D patent/FR725637A/fr not_active Expired
-
1932
- 1932-08-20 BE BE390553D patent/BE390553A/xx unknown
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2449926A (en) * | 1941-08-29 | 1948-09-21 | Emulsol Corp | Esters of alcohol nontertiary amines |
US2481692A (en) * | 1944-04-12 | 1949-09-13 | Rayonier Inc | Cotton treated with a cation active amine |
US2861863A (en) * | 1952-12-19 | 1958-11-25 | Basf Ag | Improvement of fastness of cellulosic fibers with a polymerization product of basic vinyl compounds |
US2950217A (en) * | 1956-11-13 | 1960-08-23 | Du Pont | Impregnation process |
DE2121013A1 (de) * | 1971-04-29 | 1972-11-23 | Bayer Ag, 5090 Leverkusen | Quaternäre Ammoniumverbindungen |
US3873583A (en) * | 1971-04-29 | 1975-03-25 | Bayer Ag | Quaternary ammonium compounds |
US4001285A (en) * | 1971-07-27 | 1977-01-04 | Sandoz Ltd. | Amidopolyaminesulfonates |
US4247295A (en) * | 1979-05-14 | 1981-01-27 | Estampados Estil, S.A. | Discharge printing of textiles dyed with indigo blue |
US4436521A (en) | 1979-10-18 | 1984-03-13 | Sandoz Ltd. | Process for producing dyed and anti-shrink treated wool |
Also Published As
Publication number | Publication date |
---|---|
DE582101C (de) | 1933-08-10 |
FR725637A (fr) | 1932-05-14 |
GB366918A (en) | 1932-02-04 |
NL30888C (en(2012)) | 1932-09-15 |
BE390553A (en(2012)) | 1932-09-20 |
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