US1900172A - Treatment oe textile and other materials - Google Patents
Treatment oe textile and other materials Download PDFInfo
- Publication number
- US1900172A US1900172A US1900172DA US1900172A US 1900172 A US1900172 A US 1900172A US 1900172D A US1900172D A US 1900172DA US 1900172 A US1900172 A US 1900172A
- Authority
- US
- United States
- Prior art keywords
- materials
- textile
- vat
- compounds
- anthraquinone
- 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
- 239000000463 material Substances 0.000 title description 110
- 239000004753 textile Substances 0.000 title description 66
- 150000001875 compounds Chemical class 0.000 description 114
- 238000004040 coloring Methods 0.000 description 64
- 229920002301 Cellulose acetate Polymers 0.000 description 54
- 229940081735 acetylcellulose Drugs 0.000 description 54
- 229920002678 cellulose Polymers 0.000 description 54
- 238000000034 method Methods 0.000 description 54
- 239000006185 dispersion Substances 0.000 description 46
- 239000001913 cellulose Substances 0.000 description 42
- 239000002253 acid Substances 0.000 description 34
- 239000002270 dispersing agent Substances 0.000 description 30
- RZVHIXYEVGDQDX-UHFFFAOYSA-N Anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 20
- -1 Anthraquinone acridones Chemical class 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 239000000084 colloidal system Substances 0.000 description 18
- 239000000975 dye Substances 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 18
- 230000001681 protective Effects 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000003513 alkali Substances 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 229920000742 Cotton Polymers 0.000 description 14
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 14
- 150000001447 alkali salts Chemical class 0.000 description 12
- 238000004043 dyeing Methods 0.000 description 12
- 230000003647 oxidation Effects 0.000 description 12
- 238000007254 oxidation reaction Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- 150000007513 acids Chemical class 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000008234 soft water Substances 0.000 description 10
- 241001062009 Indigofera Species 0.000 description 8
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000004744 fabric Substances 0.000 description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- 230000001264 neutralization Effects 0.000 description 8
- 239000006072 paste Substances 0.000 description 8
- 239000000344 soap Substances 0.000 description 8
- 239000002759 woven fabric Substances 0.000 description 8
- 229940097275 Indigo Drugs 0.000 description 6
- 210000002268 Wool Anatomy 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
- 229920003086 cellulose ether Polymers 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 150000007524 organic acids Chemical class 0.000 description 6
- 230000001603 reducing Effects 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 6
- 229920002955 Art silk Polymers 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- JXDYKVIHCLTXOP-UHFFFAOYSA-N Isatin Natural products C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 4
- 210000004940 Nucleus Anatomy 0.000 description 4
- WBHHMMIMDMUBKC-QJWNTBNXSA-N Ricinoleic acid Chemical class CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-QJWNTBNXSA-N 0.000 description 4
- JBUKJLNBQDQXLI-UHFFFAOYSA-N Sodium perborate Chemical compound [Na+].[Na+].O[B-]1(O)OO[B-](O)(O)OO1 JBUKJLNBQDQXLI-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 4
- 239000005864 Sulphur Substances 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000004056 anthraquinones Chemical class 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 150000003949 imides Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000003638 reducing agent Substances 0.000 description 4
- 229960001922 sodium perborate Drugs 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 239000001117 sulphuric acid Substances 0.000 description 4
- 235000011149 sulphuric acid Nutrition 0.000 description 4
- 239000002641 tar oil Substances 0.000 description 4
- 230000001131 transforming Effects 0.000 description 4
- CRDNMYFJWFXOCH-BUHFOSPRSA-N (3E)-3-(3-oxo-1H-indol-2-ylidene)-1H-indol-2-one Chemical class N\1C2=CC=CC=C2C(=O)C/1=C1/C2=CC=CC=C2NC1=O CRDNMYFJWFXOCH-BUHFOSPRSA-N 0.000 description 2
- PPKPKFIWDXDAGC-IHWYPQMZSA-N (Z)-1,2-dichloroprop-1-ene Chemical class C\C(Cl)=C\Cl PPKPKFIWDXDAGC-IHWYPQMZSA-N 0.000 description 2
- 150000004057 1,4-benzoquinones Chemical class 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-Naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- OVYHWGDANKJLIW-UHFFFAOYSA-M 2-N,2-N,8-N,8-N-tetraethyl-10-phenylphenazin-10-ium-2,8-diamine;chloride Chemical compound [Cl-].C12=CC(N(CC)CC)=CC=C2N=C2C=CC(N(CC)CC)=CC2=[N+]1C1=CC=CC=C1 OVYHWGDANKJLIW-UHFFFAOYSA-M 0.000 description 2
- VZMULMSIWMLZLC-UHFFFAOYSA-N 2-aminoanthra[9,1,2-cde]benzo[rst]pentaphene-5,10-dione Chemical compound C12=C3C4=CC=C2C2=CC=CC=C2C(=O)C1=CC=C3C1=CC=C2C(=O)C3=CC=C(N)C=C3C3=CC=C4C1=C32 VZMULMSIWMLZLC-UHFFFAOYSA-N 0.000 description 2
- XBNVWXKPFORCRI-UHFFFAOYSA-N 2H-naphtho[2,3-f]quinolin-1-one Chemical class C1=CC=CC2=CC3=C4C(=O)CC=NC4=CC=C3C=C21 XBNVWXKPFORCRI-UHFFFAOYSA-N 0.000 description 2
- WVRFSLWCFASCIS-UHFFFAOYSA-N 3-(3-ethylcyclopentyl)propanoic acid Chemical class CCC1CCC(CCC(O)=O)C1 WVRFSLWCFASCIS-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- 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 2
- HUKPVYBUJRAUAG-UHFFFAOYSA-N Benzanthrone Chemical class C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=CC=CC2=C1 HUKPVYBUJRAUAG-UHFFFAOYSA-N 0.000 description 2
- OTQLQCRWKBMVPJ-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)O.C(CCCCCCCCCCCCCCC)(=O)O Chemical class C1(=CC=CC=C1)S(=O)(=O)O.C(CCCCCCCCCCCCCCC)(=O)O OTQLQCRWKBMVPJ-UHFFFAOYSA-N 0.000 description 2
- KVAKZOJKMYTFFS-UHFFFAOYSA-N C12C(C3C(C=4C(C5=CC=CC=C5C(C14)=O)=O)O3)O2 Chemical class C12C(C3C(C=4C(C5=CC=CC=C5C(C14)=O)=O)O3)O2 KVAKZOJKMYTFFS-UHFFFAOYSA-N 0.000 description 2
- YRUALVKYPPTOHT-UHFFFAOYSA-N C12C(C3C(C=4C(C5=CC=CC=C5C(C14)=O)=O)S3)S2 Chemical class C12C(C3C(C=4C(C5=CC=CC=C5C(C14)=O)=O)S3)S2 YRUALVKYPPTOHT-UHFFFAOYSA-N 0.000 description 2
- XQGDNRFLRLSUFQ-UHFFFAOYSA-N C1=C(C2=C3C4=C56)C=CC3=CC5=C3C=CC=CC3=CC6=CC=C4C=C2C2=C1C(=O)CC=C2 Chemical compound C1=C(C2=C3C4=C56)C=CC3=CC5=C3C=CC=CC3=CC6=CC=C4C=C2C2=C1C(=O)CC=C2 XQGDNRFLRLSUFQ-UHFFFAOYSA-N 0.000 description 2
- XXKXNSUKCSFHCY-UHFFFAOYSA-N C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O.S1NC=CC=C1 Chemical class C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O.S1NC=CC=C1 XXKXNSUKCSFHCY-UHFFFAOYSA-N 0.000 description 2
- AOKQIFBTPPGXDD-UHFFFAOYSA-N CNN1C=CC(C2=C1C=CC1=CC3=CC=CC=C3C=C12)=O Chemical compound CNN1C=CC(C2=C1C=CC1=CC3=CC=CC=C3C=C12)=O AOKQIFBTPPGXDD-UHFFFAOYSA-N 0.000 description 2
- HKQOBOMRSSHSTC-UHFFFAOYSA-N Cellulose acetate Chemical compound OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O.CC(=O)OCC1OC(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(COC(C)=O)O1.CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 HKQOBOMRSSHSTC-UHFFFAOYSA-N 0.000 description 2
- 229940108066 Coal Tar Drugs 0.000 description 2
- BZORFPDSXLZWJF-UHFFFAOYSA-N Dimethyl-4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 2
- 239000001828 Gelatine Substances 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- RSAZYXZUJROYKR-UHFFFAOYSA-N Indophenol Chemical compound C1=CC(O)=CC=C1N=C1C=CC(=O)C=C1 RSAZYXZUJROYKR-UHFFFAOYSA-N 0.000 description 2
- 206010022114 Injury Diseases 0.000 description 2
- BSIHWSXXPBAGTC-UHFFFAOYSA-N Isoviolanthrone Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C(C4=C56)=CC=C5C5=CC=CC=C5C(=O)C6=CC=C4C4=C3C2=C1C=C4 BSIHWSXXPBAGTC-UHFFFAOYSA-N 0.000 description 2
- WBHHMMIMDMUBKC-GKUQOKNUSA-N Ricinoleic acid Natural products CCCCCC[C@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-GKUQOKNUSA-N 0.000 description 2
- GTCMMVUVJTYUCM-LMHGUCDMSA-N S(=O)(=O)(O)C1=C(C2=CC=CC=C2C=C1)CCCCCC[C@H](CC=C/CCCCCCCC(=O)O)O Chemical compound S(=O)(=O)(O)C1=C(C2=CC=CC=C2C=C1)CCCCCC[C@H](CC=C/CCCCCCCC(=O)O)O GTCMMVUVJTYUCM-LMHGUCDMSA-N 0.000 description 2
- KIEOKOFEPABQKJ-UHFFFAOYSA-N Sodium dichromate Chemical compound [Na+].[Na+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KIEOKOFEPABQKJ-UHFFFAOYSA-N 0.000 description 2
- JVBXVOWTABLYPX-UHFFFAOYSA-L Sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 2
- JOUDBUYBGJYFFP-FOCLMDBBSA-N Thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 2
- 241001584775 Tunga penetrans Species 0.000 description 2
- JXUKQCUPTNLTCS-UHFFFAOYSA-N Vat Green 1 Chemical compound C1=CC=C[C]2C(=O)C(C3=C45)=CC=C4C(C4=C67)=CC=C7C(=O)[C]7C=CC=CC7=C6C=C(OC)C4=C5C(OC)=CC3=C21 JXUKQCUPTNLTCS-UHFFFAOYSA-N 0.000 description 2
- YKSGNOMLAIJTLT-UHFFFAOYSA-N Violanthrone Chemical compound C12=C3C4=CC=C2C2=CC=CC=C2C(=O)C1=CC=C3C1=CC=C2C(=O)C3=CC=CC=C3C3=CC=C4C1=C32 YKSGNOMLAIJTLT-UHFFFAOYSA-N 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 230000002378 acidificating Effects 0.000 description 2
- 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 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- BEQBQOAWTXSRIB-UHFFFAOYSA-N anthracene-9,10-dione;1,3-thiazole Chemical class C1=CSC=N1.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 BEQBQOAWTXSRIB-UHFFFAOYSA-N 0.000 description 2
- HEIBZOUCLKDVHK-UHFFFAOYSA-N anthracene-9,10-dione;2H-oxazine Chemical class N1OC=CC=C1.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 HEIBZOUCLKDVHK-UHFFFAOYSA-N 0.000 description 2
- VNGZQMYDWYDBDQ-UHFFFAOYSA-N anthracene-9,10-dione;9H-carbazole Chemical class C1=CC=C2C3=CC=CC=C3NC2=C1.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 VNGZQMYDWYDBDQ-UHFFFAOYSA-N 0.000 description 2
- DZHDFIWOPAVEOZ-UHFFFAOYSA-N anthracene-9,10-dione;quinoline Chemical class N1=CC=CC2=CC=CC=C21.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 DZHDFIWOPAVEOZ-UHFFFAOYSA-N 0.000 description 2
- GGZQGKZALYVJBJ-UHFFFAOYSA-N anthracene-9,10-dione;thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 GGZQGKZALYVJBJ-UHFFFAOYSA-N 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 229940095076 benzaldehyde Drugs 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-M butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 2
- 150000001716 carbazoles Chemical class 0.000 description 2
- 150000001717 carbocyclic compounds Chemical class 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 230000001808 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- CBYZIWCZNMOEAV-UHFFFAOYSA-N formaldehyde;naphthalene Chemical compound O=C.C1=CC=CC2=CC=CC=C21 CBYZIWCZNMOEAV-UHFFFAOYSA-N 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 230000002140 halogenating Effects 0.000 description 2
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 2
- 150000002440 hydroxy compounds Chemical class 0.000 description 2
- 229920005610 lignin Polymers 0.000 description 2
- 239000003077 lignite Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M methanoate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 235000013379 molasses Nutrition 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 150000002791 naphthoquinones Chemical class 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000004893 oxazines Chemical class 0.000 description 2
- 230000001590 oxidative Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- PNIJRIIGBGFYHF-UHFFFAOYSA-N perborate(2-) Chemical compound O[B-]1(O)OO[B-](O)(O)OO1 PNIJRIIGBGFYHF-UHFFFAOYSA-N 0.000 description 2
- IYYMDGDZPDXTGT-UHFFFAOYSA-N perylene-1,2-dione Chemical class C1=CC(C2=C3C(=CC(C2=O)=O)C=CC=C32)=C3C2=CC=CC3=C1 IYYMDGDZPDXTGT-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229960003656 ricinoleic acid Drugs 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 230000002522 swelling Effects 0.000 description 2
- HOPRIFATEWRIEO-XGZFOCIOSA-J tetrasodium;(3E)-5-amino-3-[[4-[4-[(2Z)-2-(8-amino-1-oxo-3,6-disulfonatonaphthalen-2-ylidene)hydrazinyl]phenyl]phenyl]hydrazinylidene]-4-oxonaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].O=C\1C2=C(N)C=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C/1=N/NC(C=C1)=CC=C1C(C=C1)=CC=C1N\N=C1/C(S([O-])(=O)=O)=CC(C=C(C=C2N)S([O-])(=O)=O)=C2C1=O HOPRIFATEWRIEO-XGZFOCIOSA-J 0.000 description 2
- 150000004897 thiazines Chemical class 0.000 description 2
- 150000003557 thiazoles Chemical class 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 150000007964 xanthones Chemical class 0.000 description 2
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
- D06P1/22—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 vat dyestuffs including indigo
- D06P1/24—Anthraquinone dyes or anthracene nucleus containing vat 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
- D06P1/22—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 vat dyestuffs including indigo
- D06P1/28—Esters of vat dyestuffs
-
- 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
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/921—Cellulose ester or ether
Definitions
- This invention relates to the colouration by dyeing, printing, stencilling or otherwise of textile or other materials.
- Vat colouring matters have long been employed on a very extensive scale for the colouration of cellulosic materials.
- the colouring matters have been applied to the sand materials in the form of alkali salts of their reduction products, the so-called leuco compounds, and the colourations obtained have been highly valued on account of them resistance to the agencies to which textlle materials are commonly subjected.
- the appllcation of these vat colouring matters to other textile materials has in the past met wlth very serious difficulties owing either to the comparatively small afiinity of the materials for the alkali salts of the leuco compounds, or to their being easily injured by the alkaline conditions existing in the dye vats.
- the application of the vat colouring matters to WOOl and silk, for instance, has in thepast been principally confined to the use of a few colouring matters which can be vatted in the presence'of small quantities of alkali.
- the colouration of textile or other materials made of or containing cellulose acetate or other organic derivatives of cellulose is effected by processes comprising the application of free leuco compounds of vat colouring matters.
- Vat colouring matters may thus be applied to the material in the absence of alkali, for example under neutral or acid conditions, a very great advantage in the treatment of cellulose ester materials.
- the afiinities in relation to any particular fibre, of the leuco compounds of vat dyestuffs uncombined with alkalies in general differ considerably from those of the compounds of leuco bodies with alkalies.
- the invention renders possible the production of colourations, for example colourations on materials comprising two or more types of fibre, which are difiicult or impossible of attainment by hitherto known methods.
- Free leuco compounds of the vat colouring matters may be applied to the textile or other materials in any convenient manner, for example in the form of solutions, e. g. in organic solvents. They are however most satisfactorily and conveniently applied in the form of aqueous dispersions or suspensions, and this method of application constitutes a very important feature of the present invention. Contrary to expectation, it has been found that the solutions, dispersions, or other preparations containing the free leuco compounds are remarkably stable in the presence of air. Cellulose ester or ether materials show an exceptionally good affinity for the free leuco compounds, often greater than the aflinity of the same materials for the alkali salts of the leuco compounds.
- the free leuco compounds of the indigoid colouring matters have such remarkably good aflinity for cellulose ester materials under neutral or acid conditions that it is even possible to rinse the materials before oxidizing the leuco compound, and colourations of excellent fastness to rubbing are thereupon obtained.
- the dyeing operation can be effected under non-alkaline conditions, all danger of saponification of the cellulose ester may be avoided.
- a further valuable feature of the invention resides in the fact that the range of conditions for optimum dyeing is in general much wider than with alkaline vats.
- Vat dyestuff is to be understood as comprising not only those colouring matters commonly employed for application to textile materials. from alkaline vats, but any other colouring matters capable of yielding by reduction compounds which may be converted by oxidation into the original colouring matters. The following are given as instances of such colouring matters or classes of colouring matters 1. Indi 0 and allied colouring matters.
- N .N'-dimethyl indigo and halogenated indigoes for example N .N'-dimethyl indigo and halogenated indigoes, e. g. Ciba blue 2B (Colour Index 1184
- Halogenated indirubines e. g. Ciba heliotrope B (Colour Index 1205).
- Indigoid dyes obtainable by condensing isatins or thioisatins with u-oxynaphthalenes or woxy-anthracenes or derivatives thereof and if desired subsequently halogenating, e. g. Alizarin indigo 3R (Colour Index 1200) and Helindone blue 3GN (Colour Index 1203).
- Anthrapyridones e. g. 4-methylaminoanthrapyridone.
- Anthraquinone-mercaptans including their derivatives substituted in the nucleus and/or the mercapto groups.
- Benzanthrones and dibenzanthrones e. g. Violanthrone (Colour Index 1099); Iso-violanthrone (Colour Index 1103) Amino-violanthrone (Colour Index 1102); Dimgthoxy-dibenzanthrone (Colour Index 1101 (g) Pyranthrone and its derivatives.
- Anthraquinone acridones e. g. anthraquinone 1 (NI-I) -2 (CO) -naphthacridone (Colour Index 1162).
- Dianthraquinonylamines and derivatives e. g. acidylamino derivatives.
- Anthraquinone disulphides (g) Anthraquinone xanthones. (1-) Anthraquinone thioxanthones. (a) Anthraquinone carbazoles.
- Dyestuffs obtainable by alkali fusion of imides and substituted imides of naphthalene peridicarboxylic acids and the dyestuffs obtainable by condensing naphthalene 1: 1: 5 S-tetraearboxylic acids with monoor diamines.
- Sulphur dyestufi's including not only those colouring matters commonly applied from sulphide baths but also those sulphur colouring matters commonly applied to cellulosic materials from hydrosulphite or other vats, for example the colouring matters obtained by sulphurizing indophenols derived from. carbazol (see Colour Index Nos. 969, 970, 971, etc.)
- Dispersions or suspensions of free leuco compounds of colouring matters may be obtained by any convenient means, whether mechanical or otherwise.
- the free leuco compounds themselves may be directly converted into aqueous dispersions by mechanical treatment or by treatment with dispersing agents and/or protective colloids.
- the leuco compounds may be liberated or formed in the presence of dispersing agents and/or protective colloids, and in this manner dispersions or suspensions directly applicable for dyeing may be produced.
- vat colouring matters may be vatted with the aid of alkali and bydrosulphite or other reducing agents in the known manner and acidified with a suitable organic or inorganic acid in presence of protective colloids and/or dispersing agents.
- the protective colloids or dispersing agents themselves may be converted by the acidification into other and even more suitable forms.
- the dispersing agents and protective colloids should be as stable as possible under the conditions in which the dispersions or supensions are to be stored or applied.
- dispersing agents or protective colloids the following may be in stanced:-
- Sulphoaromatic fatty acid compounds e. g. sulphobenzene palmitic acid compounds (see United States Patent No. 1,694,413).
- Sulphoaromatic ricinoleic acid compounds e. g. sulphonaphthalenericinoleic acid
- Naphthenic acids or other carbocyclic compounds containing salt-forming groups or salts of such acids or compounds see United States Patent No. 1,618,414.
- Sulphonated oil compounds e. g. sul-- phonated castor oil.
- Sulphonic acid compounds of mineral oils, tar oils, brown coal tar oils, and the like, and their products of condensation with alcohols are examples of Sulphonic acid compounds of mineral oils, tar oils, brown coal tar oils, and the like, and their products of condensation with alcohols.
- Carbohydrates including gums.
- Aqueous dispersions or suspensions of the free leuco compounds may be acid, neutral or even slightly alkaline. For example they may have hydrogen ion concentrations corresponding to pH values lying between 3 and 9, for instance between 4 and 8.
- the colouration of cellulose acetate and other organic substitution derivatives of cellulose may be accomplished in a highly satisfactory manner with aqueous suspensions or dispersions containing sufficient acetic, formic, or other organic acid to render them slightly acid to litmus.
- the dispersions of the free leuco compounds may be prepared in the dyebaths themselves, 'or in the form of more or less concentrated liquid, paste, solid, or powdered or other preparations which may be used for the preparation of dyebaths.
- Such preparations may be obtained for instance by removal of water by evaporation or otherwise from less concentrated dispersions, or by acidifying concentrated solutions of alkali salts of leuco compounds of vat colouring matters in the presence of dispersing agents and/or protective colloids, or by simple grinding of the leuco compounds with dispersing agents and/or protective colloids with or without water.
- the preparations preferably contain water and may receive additions of agents, e. g.
- reducing agents or acids adapted to in crease their stability in the presence of air.
- These preparations comprise an important feature of the present invention, which further includes preparations which contain dispersing agents, particularly those referred to above, and/or protective colloids, together with any compounds, e. g. the alkali salts of and/or dispersing agents, and after adjusting the acidity if necessary for the purpose in view.
- solutions or dispersions of free leuco compounds maybe applied to textile or other materials in any convenientmanner, for ex- ,ample by dyeing, padding printing, stencilling or the like.
- Aqueous dispersions or suspensions are preferably employed under neutral or acid conditions. If desired or requisite they may receive additions of thickening agents, for example when they are to be applied by padding or printing.
- Solutions or suspensions of free leuco compounds used ac cording to the invention appear to be in gen eral mu:h more stable than the alkaline vats hitherto employed and in consequence manipulation of the materials is in manycases much facilitated. For example it is even possible to dye fabrics on winch machines or in open width on jigger machines, where in both cases there is a considerable passage of air through the material.
- the free leuco compounds of vat dyestuffs may be applied in conjunction with swelling agents for the materials to be colcured,
- the oxidation of the leuco compounds on the materials may be effected by any suitable means, for example by simple air oxidation, treatment with bichromate and acid, treatment with bleaching powder, or treatment with soap and sodium perborate, and very satisfactory results have been obtained by oxidation in a bath containing soap and hydrogen peroxide, particularly as regards evenness of shade and little tendency of the resulting dyeings to rub.
- the new process of colouration is applicable to any materials consisting of or containing cellulose esters or ethers and is particular- 1y valuable in the colouration of su h textile and other materials as are liable to injury by alkali, for example materials made of or containing cellulose esters, for example filaments, yarns, fabrics, ribbons and films made of these esters, e. g. cellulose acetate, formate, propionate. or butyrate, or the products obtained by the treatment of alkalized cellulose with esterifying agents, for instance the product known as immunized cotton obtained with p-toluene sulpho chloride.
- the invention is also applicable to the colouration of other organic substitution derivatives of cellulose for example cellulose ethers, e. g.
- colourat-ions may for instance be produced on organic derivatives of cellulose in accordance with the invention by means of the free leuco compounds of indigoid and thioindigoid colouring matters and colouring matters containing a single ant-hraquinone nucleus, for example of the following series :anthraquinone acridones, oxazines, dioxides, thiazines, disulphides, xanthones, thioxanthones, carbazoles, and thiazoles.
- anthraquinone acridones oxazines, dioxides, thiazines, disulphides, xanthones, thioxanthones, carbazoles, and thiazoles.
- Cellulosic materials for example cotton, linen, or the regenerated celulose type of artificial silk show in general little or no affinity for the free leuco compounds of vat colouring matters applied in accordance with the present invention.
- the new process therefore renders possible the production of valuable cross-dyed effects on certain mixed materials.
- fabrics composed of cellulose acetate and cotton, or natural silk and cotton, or cel'ulose acetate and a regenerated cellnlosic type of artificial silk may be dyed with a dispersion of the free leuco compound of a vat colouring matter.
- the cellulosic portion oi the material may be coloured prior to the cellulose. acetate part; for example the cellulosic portion may be dyed with a vat dyestufl in the presence of alkali salts of arcmatic hydroxy compounds as described in U. S. Patent No. 1,716,720 so as to leave unstained the ce lulose acetate and the latter then dyed with a vat dyestufi' in the form of a dispersion of its free leuco compound.
- Example I 200 grams of the brominated indigo known as Ciba blue G powder (Colour Index No. 1185) are pasted with 2.5 litres of the solution of sodium salt of sulphonaphthalene ricinoleic acid prepared according to Example A of U. S. Patent No. 1.69%,413, and 4:0 to litres of Water at C. added with stirring. 200 grams of caustic soda are now added, and 350 grams of sodium hydrosulphite sprinkled in with good stirring, and stirring continned for 5-10 minutes or till reduction is complete, after which the liquor is filtered into a dyebath containing 500 litres of soft water at 50 C. to which 50 grams of hydrosulphite have previously been added.
- the dyebath is now rendered slightly acid to litmus by careful addition of approximately 3 litres of 10% acetic acid, whereby the tree leuco compound is obtained as a very satisfactory dispersion.
- 10 kilograms of cellulose acetate yarn in bank form are now entered, and the temperature raised to 7580 C. in 1 1/ hour and held thereabouts for k to our.
- the goods are now lifted, rinsed in soft water, hydro-extracted, and hung up to oxidize, after which they are given a light soaping in a 1 gram per litre soap bath to which perborate may advantageously be added, rinsed, and dried or otherwise treated as req- Lusite.
- Example 2 200 grams of the vat dyestufi known as Caledon jade green (Colour Index No. 1101) are pasted with 2.5 litres of a highly sulpho 1 nated castor oil stable to dilute organic acids,
- Example 1 suitably diluted, and vatted with 200 grams of caustic soda and 350 grams hydrosulphite as in Example 1.
- the clear solution is now added to the dyebath previously set with hydrosulphite, acidified, and 10 kilos of cellulose acetate yarn in hank form entered and processed exact y as detailed in that example. After oxidation, and soaping, the goods which are now dyed a bright green, shade, are rinsed and dried or otherwise treated as requisite.
- cellulose acetate yarns may be coloured in red shades by means of Caledon red BN (Colour Index 1162), or in yellow shades by means of 2':5'-dichloro- 1 Q-anthraquinone thioxanthone.
- Example 5 200 grams of the indophenol dyestuff prepared by oxidation of p-aminodimethylaniline and alphanaphthol (Colour Index No. 831) are pasted with 1 litre of sulphite cellulose liquor, or an equivalent quantity of a suitable product of transformation, and 40 to 50 litres of water at 60 C. are added with stirring. 200 grams of caustic soda are now added and 300 grams hydrosulphite sprinkled in with stirring, and stirring continued till vatting is complete, after which the liquor is filtered into a suitable dyebath containing 500 litres of soft water at 50 C. previously set with 50 grams of hydrosulphite.
- the dyebath is now acidified by careful addition of approximately 3 litres of 10% acetic acid, and 10 kilograms of cellulose acetate woven fabric entered, after which the temperature is raised to 7 5 to 80 C. in hour and held thereabouts for hour.
- the goods are now lifted, rinsed, hydroextracted, and allowed to oxidize in the air, or in a bath containing 1 gram per litre soap and 2 grams per litre sodium perborate till the colour is fully developed, after which they are lifted, rinsed, and dried or otherwise treated as requisite.
- the goods are now lifted, rinsed, soaped lightly, washed off well, and dried or otherwise treated as requisite. dyed in full shades of pink.
- Process for the coloration of textile and other materials containing cellulose acetate comprising applying thereto a composition comprising a free leuco compound of a vat dyestuff and a dispersing agent.
- Process for the coloration of textile and other materials containing cellulose acetate comprising applying thereto a composition comprising a free leuco compound of an indigoid Vat dyestufi' and a dispersing agent.
- Process for the coloration of textile and other materials containing cellulose acetate comprising applying thereto a composition comprising a free leuco compound of an anthraquinone vat dyestufl' containing only one anthraquinone residue and a dispersing agent.
- Process for the coloration of textile and other materials containing cellulose acetate comprising applying thereto a preparation made by vatting a vat dyestufi in alkaline medium and adding in the presence of a dispersing agent at least sufiicient acid to separate free leuco compound of the dyestufi.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Description
Patented Mar. 7, 1933 UNITED STATES PATENT OFFICE GEORGE HOLLAND ELLIS, HENRY CHARLES OIIPIN, AND RALPH CHARLES STOREY, OI
BPONDON, NEAR DERBY, ENGLAND, ASSIGNORS TO CELANESE CORPORATION 01' AMERICA, A CORPORATION OF DELAWARE TREATMENT OI TEXTILE AND OTHER MATERIALS No Drawing. Application filed June 7, 1930, Serial No. 459,828, and in Great Britain July 4, 1929.
This invention relates to the colouration by dyeing, printing, stencilling or otherwise of textile or other materials.
Vat colouring matters have long been employed on a very extensive scale for the colouration of cellulosic materials. The colouring matters have been applied to the sand materials in the form of alkali salts of their reduction products, the so-called leuco compounds, and the colourations obtained have been highly valued on account of them resistance to the agencies to which textlle materials are commonly subjected. The appllcation of these vat colouring matters to other textile materials has in the past met wlth very serious difficulties owing either to the comparatively small afiinity of the materials for the alkali salts of the leuco compounds, or to their being easily injured by the alkaline conditions existing in the dye vats. The application of the vat colouring matters to WOOl and silk, for instance, has in thepast been principally confined to the use of a few colouring matters which can be vatted in the presence'of small quantities of alkali.
The very remarkable discovery has been made that the free leuco compounds of vat colouring matters have good affinity for and can be directly applied to very many textile and other materials to produce valuable colourations thereon.
According to the present invention therefore, the colouration of textile or other materials made of or containing cellulose acetate or other organic derivatives of cellulose is effected by processes comprising the application of free leuco compounds of vat colouring matters. Vat colouring matters may thus be applied to the material in the absence of alkali, for example under neutral or acid conditions, a very great advantage in the treatment of cellulose ester materials. Moreover the afiinities in relation to any particular fibre, of the leuco compounds of vat dyestuffs uncombined with alkalies in general differ considerably from those of the compounds of leuco bodies with alkalies. In consequence the invention renders possible the production of colourations, for example colourations on materials comprising two or more types of fibre, which are difiicult or impossible of attainment by hitherto known methods.
Free leuco compounds of the vat colouring matters may be applied to the textile or other materials in any convenient manner, for example in the form of solutions, e. g. in organic solvents. They are however most satisfactorily and conveniently applied in the form of aqueous dispersions or suspensions, and this method of application constitutes a very important feature of the present invention. Contrary to expectation, it has been found that the solutions, dispersions, or other preparations containing the free leuco compounds are remarkably stable in the presence of air. Cellulose ester or ether materials show an exceptionally good affinity for the free leuco compounds, often greater than the aflinity of the same materials for the alkali salts of the leuco compounds. For instance the free leuco compounds of the indigoid colouring matters have such remarkably good aflinity for cellulose ester materials under neutral or acid conditions that it is even possible to rinse the materials before oxidizing the leuco compound, and colourations of excellent fastness to rubbing are thereupon obtained. In addition, as the dyeing operation can be effected under non-alkaline conditions, all danger of saponification of the cellulose ester may be avoided. A further valuable feature of the invention resides in the fact that the range of conditions for optimum dyeing is in general much wider than with alkaline vats. Thus, not only does the invention enable colouring to be effected under much less closely controlled conditions, but it much facilitates the application of mixtures of dye- Vat dyestuffs of any desired kind may be employed for application according to the process of the present invention, and the term Vat dyestuff is to be understood as comprising not only those colouring matters commonly employed for application to textile materials. from alkaline vats, but any other colouring matters capable of yielding by reduction compounds which may be converted by oxidation into the original colouring matters. The following are given as instances of such colouring matters or classes of colouring matters 1. Indi 0 and allied colouring matters.
(a) In igo and its derivatives, for example N .N'-dimethyl indigo and halogenated indigoes, e. g. Ciba blue 2B (Colour Index 1184 (b) Halogenated indirubines, e. g. Ciba heliotrope B (Colour Index 1205).
(c) Thioindigo and its derivatives, for instance halogenated thioindigoid dyes, e. g Ciba Bordeaux B (Colour Index 1208).
(d) Dinaphthindigoid dyes, e. g. Ciba green G (Colour Index 1198).
(e) Indigoid dyes obtainable by condensing isatins or thioisatins with u-oxynaphthalenes or woxy-anthracenes or derivatives thereof and if desired subsequently halogenating, e. g. Alizarin indigo 3R (Colour Index 1200) and Helindone blue 3GN (Colour Index 1203).
2. Anthraquinone colouring matters.
(a) Simple amino-derivatives, e. g. l-hydroxyl-amino-anthraquinone; 1: 5-diamino- 4 8-dihydroxy-anthraquinone; l-methylamino-anthraquinone; 1 4 dianilide-anthraquinone.
(b) Anthraquinone-quinolines, e. g. 1:2- dihydroxy-anthraquinone-quinoline (Colour Index 1066).
(c) Acylamino anthraquinones, e. g. l-acetylamino-anthraquinone; 1 t-dipropionylaminoanthraquinone 1 :5 dibenzoylaminoanthraquinone (Colour Index 1132); succinyl-alphaamino anthraquinone (Colour Index 1139) 1: 5-dibenzoylamino-4 8-dihydrox -anthraquinone (Colour Index 1134).
(d Anthrapyridones, e. g. 4-methylaminoanthrapyridone.
(e) Anthraquinone-mercaptans including their derivatives substituted in the nucleus and/or the mercapto groups.
(f) Benzanthrones and dibenzanthrones, e. g. Violanthrone (Colour Index 1099); Iso-violanthrone (Colour Index 1103) Amino-violanthrone (Colour Index 1102); Dimgthoxy-dibenzanthrone (Colour Index 1101 (g) Pyranthrone and its derivatives.
(h) Anthraflavone (Colour Index 1095).
(i) Anthraquinone acridones, e. g. anthraquinone 1 (NI-I) -2 (CO) -naphthacridone (Colour Index 1162).
(j) Dianthraquinonyls and acidylamino derivatives.
Dianthraquinonylamines and derivatives, e. g. acidylamino derivatives.
(Z) Anthraquinone azines and hydroazines, e. g. dianthraquinone-dihydroazines and their halogenated derivatives such as 1 2.1 2'-dianthraquinone azine (Colour Index 1106) and its dichlor derivatives (Colour Index 1113).
(m) Anthraquinone oxazines. (n) Anthraquinone dioxides.
0) Anthraquinone thiazines.
p) Anthraquinone disulphides. (g) Anthraquinone xanthones. (1-) Anthraquinone thioxanthones. (a) Anthraquinone carbazoles.
t Anthraquinone thiazoles.
3. Derivatives of benzoquinone and naphthoquinones, e. g. those mentioned in United States patent applications S. Nos. 379,874 and 379,87 5 both filed 20th July, 1929.
4. Indophenols and their derivatives, e. g. halogen derivatives.
5. Perylene quinones and their amino, halogen and other derivatives.
6. Dyestuffs obtainable by alkali fusion of imides and substituted imides of naphthalene peridicarboxylic acids and the dyestuffs obtainable by condensing naphthalene 1: 1: 5 S-tetraearboxylic acids with monoor diamines.
7. Sulphur dyestufi's including not only those colouring matters commonly applied from sulphide baths but also those sulphur colouring matters commonly applied to cellulosic materials from hydrosulphite or other vats, for example the colouring matters obtained by sulphurizing indophenols derived from. carbazol (see Colour Index Nos. 969, 970, 971, etc.)
Dispersions or suspensions of free leuco compounds of colouring matters may be obtained by any convenient means, whether mechanical or otherwise. For example the free leuco compounds themselves may be directly converted into aqueous dispersions by mechanical treatment or by treatment with dispersing agents and/or protective colloids. Alternatively the leuco compounds may be liberated or formed in the presence of dispersing agents and/or protective colloids, and in this manner dispersions or suspensions directly applicable for dyeing may be produced. For example vat colouring matters may be vatted with the aid of alkali and bydrosulphite or other reducing agents in the known manner and acidified with a suitable organic or inorganic acid in presence of protective colloids and/or dispersing agents. Moreover, the protective colloids or dispersing agents themselves may be converted by the acidification into other and even more suitable forms. The dispersing agents and protective colloids should be as stable as possible under the conditions in which the dispersions or supensions are to be stored or applied. As examples of dispersing agents or protective colloids the following may be in stanced:-
Sulphoaromatic fatty acid compounds, e. g. sulphobenzene palmitic acid compounds (see United States Patent No. 1,694,413).
Sulphoaromatic ricinoleic acid compounds, e. g. sulphonaphthalenericinoleic acid, (see United States patent application S. No. 134,138 filed 7th September, 1926) Naphthenic acids or other carbocyclic compounds containing salt-forming groups or salts of such acids or compounds (see United States Patent No. 1,618,414).
Sulphonated oil compounds, e. g. sul-- phonated castor oil.
.Furfural-naphthalene sulphonic acid compounds (see United States patent application S. No. 390,423 filed 4th September, 1929).
Resino-naphthalene sulphonic acid compounds (see United States patent application S. No. 390,424 filed 4th September, 1929).
Formaldehyde naphthalene sulphonic acld compounds.
Alkyl-, cycloalkyl-, and aralkyl-naphthalene sulphonic acids.
Sulphite cellulose waste liquor or 1ts constituents or products of transformation, e. g. lignin sulphonic acid compounds.
Sulphonic acid compounds of mineral oils, tar oils, brown coal tar oils, and the like, and their products of condensation with alcohols.
Sulphonic acid compounds of distillation residues of benzaldehyde.
Molasses.
Carbohydrates including gums.
Glue and gclatine.
Aqueous dispersions or suspensions of the free leuco compounds may be acid, neutral or even slightly alkaline. For examplethey may have hydrogen ion concentrations corresponding to pH values lying between 3 and 9, for instance between 4 and 8. In general, the colouration of cellulose acetate and other organic substitution derivatives of cellulose may be accomplished in a highly satisfactory manner with aqueous suspensions or dispersions containing sufficient acetic, formic, or other organic acid to render them slightly acid to litmus.
' The dispersions of the free leuco compounds may be prepared in the dyebaths themselves, 'or in the form of more or less concentrated liquid, paste, solid, or powdered or other preparations which may be used for the preparation of dyebaths. Such preparations may be obtained for instance by removal of water by evaporation or otherwise from less concentrated dispersions, or by acidifying concentrated solutions of alkali salts of leuco compounds of vat colouring matters in the presence of dispersing agents and/or protective colloids, or by simple grinding of the leuco compounds with dispersing agents and/or protective colloids with or without water. The preparations preferably contain water and may receive additions of agents, e. g. reducing agents or acids, adapted to in crease their stability in the presence of air. These preparations comprise an important feature of the present invention, which further includes preparations which contain dispersing agents, particularly those referred to above, and/or protective colloids, together with any compounds, e. g. the alkali salts of and/or dispersing agents, and after adjusting the acidity if necessary for the purpose in view.
The solutions or dispersions of free leuco compounds maybe applied to textile or other materials in any convenientmanner, for ex- ,ample by dyeing, padding printing, stencilling or the like. Aqueous dispersions or suspensions are preferably employed under neutral or acid conditions. If desired or requisite they may receive additions of thickening agents, for example when they are to be applied by padding or printing. Solutions or suspensions of free leuco compounds used ac cording to the invention appear to be in gen eral mu:h more stable than the alkaline vats hitherto employed and in consequence manipulation of the materials is in manycases much facilitated. For example it is even possible to dye fabrics on winch machines or in open width on jigger machines, where in both cases there is a considerable passage of air through the material.
If desired the free leuco compounds of vat dyestuffs may be applied in conjunction with swelling agents for the materials to be colcured,
The oxidation of the leuco compounds on the materials may be effected by any suitable means, for example by simple air oxidation, treatment with bichromate and acid, treatment with bleaching powder, or treatment with soap and sodium perborate, and very satisfactory results have been obtained by oxidation in a bath containing soap and hydrogen peroxide, particularly as regards evenness of shade and little tendency of the resulting dyeings to rub.
The new process of colouration is applicable to any materials consisting of or containing cellulose esters or ethers and is particular- 1y valuable in the colouration of su h textile and other materials as are liable to injury by alkali, for example materials made of or containing cellulose esters, for example filaments, yarns, fabrics, ribbons and films made of these esters, e. g. cellulose acetate, formate, propionate. or butyrate, or the products obtained by the treatment of alkalized cellulose with esterifying agents, for instance the product known as immunized cotton obtained with p-toluene sulpho chloride. The invention is also applicable to the colouration of other organic substitution derivatives of cellulose for example cellulose ethers, e. g. methyl, ethyl, or benzyl cellulose, or the condensation products of cellulose and glycols or other polyhydric alcohols. Particularly satisfactory colourat-ions may for instance be produced on organic derivatives of cellulose in accordance with the invention by means of the free leuco compounds of indigoid and thioindigoid colouring matters and colouring matters containing a single ant-hraquinone nucleus, for example of the following series :anthraquinone acridones, oxazines, dioxides, thiazines, disulphides, xanthones, thioxanthones, carbazoles, and thiazoles. The importance of the invention will be appreciated in View of the low affinity or lack of affinity exhibited by cellulose acetate or other organic derivatives of cellulose for the alkali compounds of leuco anthraquinone vat dyestuffs.
Mixed materials containing two or more kinds of textile fibres may be dyed by the process of the invention, the various fibres being coloured in solid or contrasting shades according to their relative afiinities for the colouring matter or matters; thus solid shades can be obtained on mixtures of cellulose acetate with wool or natural silk.
Cellulosic materials, for example cotton, linen, or the regenerated celulose type of artificial silk show in general little or no affinity for the free leuco compounds of vat colouring matters applied in accordance with the present invention. The new process therefore renders possible the production of valuable cross-dyed effects on certain mixed materials. for example on fabrics composed of cellulose acetate and cotton, or natural silk and cotton, or cel'ulose acetate and a regenerated cellnlosic type of artificial silk. For example the cellulose acetate in such a mixed material may be dyed with a dispersion of the free leuco compound of a vat colouring matter. for example an indigoid or thioindigoid colouring matter or a colouring matter containing a single anthraquinone nucleus, so as to leave uncolourcd the cotton or regenerated celulose. The latter may then, if desired. be dyed with suitable colouring matters .herci'or. Alternatively the cellulosic portion oi the material may be coloured prior to the cellulose. acetate part; for example the cellulosic portion may be dyed with a vat dyestufl in the presence of alkali salts of arcmatic hydroxy compounds as described in U. S. Patent No. 1,716,720 so as to leave unstained the ce lulose acetate and the latter then dyed with a vat dyestufi' in the form of a dispersion of its free leuco compound.
The following examples show the best Way ligown to us of carrying the invention into 0. 'ect:
Example I 200 grams of the brominated indigo known as Ciba blue G powder (Colour Index No. 1185) are pasted with 2.5 litres of the solution of sodium salt of sulphonaphthalene ricinoleic acid prepared according to Example A of U. S. Patent No. 1.69%,413, and 4:0 to litres of Water at C. added with stirring. 200 grams of caustic soda are now added, and 350 grams of sodium hydrosulphite sprinkled in with good stirring, and stirring continned for 5-10 minutes or till reduction is complete, after which the liquor is filtered into a dyebath containing 500 litres of soft water at 50 C. to which 50 grams of hydrosulphite have previously been added. The dyebath is now rendered slightly acid to litmus by careful addition of approximately 3 litres of 10% acetic acid, whereby the tree leuco compound is obtained as a very satisfactory dispersion. 10 kilograms of cellulose acetate yarn in bank form are now entered, and the temperature raised to 7580 C. in 1 1/ hour and held thereabouts for k to our.
The goods are now lifted, rinsed in soft water, hydro-extracted, and hung up to oxidize, after which they are given a light soaping in a 1 gram per litre soap bath to which perborate may advantageously be added, rinsed, and dried or otherwise treated as req- Lusite.
Example 2 200 grams of the vat dyestufi known as Caledon jade green (Colour Index No. 1101) are pasted with 2.5 litres of a highly sulpho 1 nated castor oil stable to dilute organic acids,
suitably diluted, and vatted with 200 grams of caustic soda and 350 grams hydrosulphite as in Example 1. The clear solution is now added to the dyebath previously set with hydrosulphite, acidified, and 10 kilos of cellulose acetate yarn in hank form entered and processed exact y as detailed in that example. After oxidation, and soaping, the goods which are now dyed a bright green, shade, are rinsed and dried or otherwise treated as requisite.
In the same manner cellulose acetate yarns may be coloured in red shades by means of Caledon red BN (Colour Index 1162), or in yellow shades by means of 2':5'-dichloro- 1 Q-anthraquinone thioxanthone.
Example 5 200 grams of the indophenol dyestuff prepared by oxidation of p-aminodimethylaniline and alphanaphthol (Colour Index No. 831) are pasted with 1 litre of sulphite cellulose liquor, or an equivalent quantity of a suitable product of transformation, and 40 to 50 litres of water at 60 C. are added with stirring. 200 grams of caustic soda are now added and 300 grams hydrosulphite sprinkled in with stirring, and stirring continued till vatting is complete, after which the liquor is filtered into a suitable dyebath containing 500 litres of soft water at 50 C. previously set with 50 grams of hydrosulphite. The dyebath is now acidified by careful addition of approximately 3 litres of 10% acetic acid, and 10 kilograms of cellulose acetate woven fabric entered, after which the temperature is raised to 7 5 to 80 C. in hour and held thereabouts for hour. The goods are now lifted, rinsed, hydroextracted, and allowed to oxidize in the air, or in a bath containing 1 gram per litre soap and 2 grams per litre sodium perborate till the colour is fully developed, after which they are lifted, rinsed, and dried or otherwise treated as requisite.
I Ewample 4 1 kilogram of a well ground 20% aqueous paste of the leuco compound of 1 benzoylaminol-oxy-anthraquinone is added to a solution of 150 grams of gelatine dissolved in 10 litres of water rendered faintly acidic with acetic acid. The whole is warmed to 80 C. and stirred to ensure eflicient dispersion, and then diluted in a suitable machine to 300 litres with warm soft water. 10 kilos of a woven fabric consisting of equal parts of wool and cellulose acetate previously well wetted out, are now entered, and dyeing carried out hour to 7580 C. and hour at 75 C. or thereabouts. The goods are now lifted, rinsed, and oxidized by treating for 5 minutes at 60 C. in a 300 litre bath containing 50 grams bichromate of soda, and 250 ccs. 10% sulphuric acid.
The goods are now lifted, rinsed, soaped lightly, washed off well, and dried or otherwise treated as requisite. dyed in full shades of pink.
Ewample 5 To dye 10 kilos of a woven fabric consisting of equal parts of cotton and cellulose acetate, the cotton green and the cellulose ace- The whole is heated to 95 C. with stirring,
and stirred till a good dispersion is achieved.
The whole is now diluted suitably with hotsoft water and added through a filter cloth to a dyebath containing 300 litres of soft water from which dissolved oxygen has been Both fibres are Example 6 Cellulose acetate woven fabric previously dyed with a violet dyestuif dischargeable with formosul, for example the dyestufi' obtained by coupling diazotized 3: 5-dinitro-2- amino-anisole with alphanaphthylamine, is
. requisite.
' printed with a printing paste prepared as follows Grams Gum arabic 1: 1 560 Ciba pink B 30 'Sodium sulpho-naphthalenericinoleate prepared as in U. S. Patent No.
1,694,413 50 Caustic so 30 Water 140 Hydrosulphite 40 The above are heated till vatted, cooled, and
a liquor consisting of a mixtue of Grams Formic acid 40% 90 Formosul 60 added slowly with good stirring. The
amount of liquor added should be Just sufficient to neutralize or render the paste only faintly acid. I After printing the goods are dried, passed through a rapid ager or other suitable steaming device, and then oxidized at 60C. for 5 minutes in a bath containing 2.5 grams per litre chrome and 5 grams per litre sulphuric acid. The goods are now rinsed, soaped well, washed off, and dried or otherwise treated as requisite.
What we claim and desire Letters Patent-is:-
' 1. Process for the coloration of textile and other materials containing organic derivatives of cellulose comprising applying thereto free leuco compounds of vat dyestuffs.
' 2. Process for the coloration of textile and other materials containing organic derivatives of cellulose comprising applying thereto free leuco compounds of vat dyestuffs in the form of aqueous dispersions.
3. Process for the coloration of textile and other materials containing organic derivatives of cellulose comprising applying thereto free leuco compounds of vat dyestuffs in the form of aqueous dispersions having a pH value between 3 and 9.
4. Process for the coloration of textile and other materials containing organic derivatives of cellulose comprisin appl ing thereto free leuco compounds 0 vat yestufis in to secure by the form of aqueous dispersions having a slightly acid reaction.
' agent.
6. Process for the coloration of textile and other materials containing cellulose acetate comprising applying thereto free leuco compounds of vat dyestuffs.
7. Process for the coloration of textile and other materials containing celluloseacetate comprising applying thereto free leuco compounds of vat dyestufis in the form of aque- I ous dispersions.
8. Process for the coloration of textile and other materials containing cellulose acetate comprising applying thereto free leuco compounds of vat dyestufi's in the form of aqueous dispersions having a pH value between 3 and 9.
9. Process for the coloration of textile and other materials containing cellulose acetate comprising applying thereto free leuco compounds of vat dyestufi's in the form of aqueous dispersions having a slightly acid reaction.
10. Process for the coloration of textile and other materials containing cellulose acetate comprising applying thereto a composition comprising a free leuco compound of a vat dyestuff and a dispersing agent.
11. Process for the coloration of textile and other materials containing organic derivatives of cellulose comprising applying thereto free leuco compounds of indigoid vat dyestuds.
12. Process for the coloration of textile and other materials containing cellulose acetate comprising applying thereto free leuco compounds of indigoid vat dyestuffs.
13. Process for the coloration of textile and other materials containing cellulose acetate comprising applying thereto a composition comprising a free leuco compound of an indigoid Vat dyestufi' and a dispersing agent.
14. Process for the coloration of textile and other materials containing organic derivatives of cellulose comprising applying thereto .free leuco compounds of anthraquinone vat dyestufl's.
15. Process for the coloration of textile and other materials containing cellulose acetate comprising applying thereto free leuco compounds of anthraquinone vat dyestuffs.
16. Process for the coloration of textile and other materials containing organic derivatives of cellulose comprising applying thereto free leuco compounds of anthraquinone vat dyestufi's containing only one anthraquinone residue.
17. Process for the coloration of textile and other materials containing cellulose acetate momma comprising ap lying thereto free leuco compounds of ant raqulnone vat dyestufi's containing only one antraquinone residue.
18. Process for the coloration of textile and other materials containing cellulose acetate comprising applying thereto a composition comprising a free leuco compound of an anthraquinone vat dyestufl' containing only one anthraquinone residue and a dispersing agent.
19. Process for the coloration of textile and other materials containing cellulose acetate comprising applyin thereto free leuco compounds of aminoant raquinones.
20. Process for the coloration of textile and other materials containing organic derivatives of cellulose comprising applying thereto a. preparation made by vatting a vat dyestufi' in alkaline medium and adding in the presence of a dispersing agent at least sulficient acid to separate free leuco compound of the dyestufi.
21. Process for the coloration of textile and other materials containing cellulose acetate comprising applying thereto a preparation made by vatting a vat dyestufi in alkaline medium and adding in the presence of a dispersing agent at least sufiicient acid to separate free leuco compound of the dyestufi.
22. Process for the coloration of textile and other materials containing or anic derivatives of cellulose and animal fi res comprising applying thereto free leuco compounds of vat dyestufis.
23. Process for the coloration of textile and other materials containing cellulose acetate and animal fibres comprising applying thereto free leuco compounds of vat dyestufis.
In testimony whereof we have hereunto subscribed our names.
.. GEORGE HOLLAND ELLIS. HENRY CHARLES OLPIN. RALPH CHARLES STOREY.
, CERTIFICATE OF CORRECTION.
Patent No. 1,900,172. March 7, 1933.
GEORGE HOLLAND ELLIS, ET AL.
It is hereby certified that error appears in the printed specification of the above numbered patent requiring correction as follows: Page 1, line 55, after "materials" insert the words "made of or containing cellulose acetate or other organic derivatives of cellulose"; and that the saidv Letters Patent should be read with this correction therein that the same may conform to the record of the case in the Patent Office.
Signed and sealed this 9th day of May, A. D. 1933.
M. J. Moore.
(Seal) Acting Gommisioner of Patents.
Publications (1)
Publication Number | Publication Date |
---|---|
US1900172A true US1900172A (en) | 1933-03-07 |
Family
ID=3425010
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US1900172D Expired - Lifetime US1900172A (en) | Treatment oe textile and other materials |
Country Status (1)
Country | Link |
---|---|
US (1) | US1900172A (en) |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2476287A (en) * | 1944-06-03 | 1949-07-19 | Celanese Corp | Method for producing watersoluble leuco vat dyestuff |
US2524093A (en) * | 1948-04-20 | 1950-10-03 | Celanese Corp | Union dyeing of mixed fabrics of cellulose ester and animal fibers with alkaline reduced vat dye solutions containing swelling agents |
US2590213A (en) * | 1949-07-23 | 1952-03-25 | George N Sandor | Process of preparing concentrated vat acids |
US2627449A (en) * | 1951-03-14 | 1953-02-03 | Luttringhaus Hans | Dyeing of polyester fibers with acid leuco vat dyes |
US2670263A (en) * | 1951-03-21 | 1954-02-23 | Gen Dyestuff Corp | Composition and process for dyeing polyethylene terephthalate fibers |
US2681845A (en) * | 1951-01-15 | 1954-06-22 | Gen Dyestuff Corp | Acid vat dyeing of animal fibers |
US2695832A (en) * | 1951-08-24 | 1954-11-30 | Gen Aniline & Film Corp | Dyeing of acrylic fibers with vat dyestuffs |
US2774647A (en) * | 1952-05-17 | 1956-12-18 | American Cyanamid Co | Dyeing of polyesters with vat dyes |
US2774649A (en) * | 1952-05-17 | 1956-12-18 | American Cyanamid Co | Dyeing of cellulose carboxylic acid esters with vat dyes |
US2798788A (en) * | 1952-06-21 | 1957-07-09 | Celanese Corp | Vat dyeing of cellulose ethers and esters |
-
0
- US US1900172D patent/US1900172A/en not_active Expired - Lifetime
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2476287A (en) * | 1944-06-03 | 1949-07-19 | Celanese Corp | Method for producing watersoluble leuco vat dyestuff |
US2524093A (en) * | 1948-04-20 | 1950-10-03 | Celanese Corp | Union dyeing of mixed fabrics of cellulose ester and animal fibers with alkaline reduced vat dye solutions containing swelling agents |
US2590213A (en) * | 1949-07-23 | 1952-03-25 | George N Sandor | Process of preparing concentrated vat acids |
US2681845A (en) * | 1951-01-15 | 1954-06-22 | Gen Dyestuff Corp | Acid vat dyeing of animal fibers |
US2627449A (en) * | 1951-03-14 | 1953-02-03 | Luttringhaus Hans | Dyeing of polyester fibers with acid leuco vat dyes |
US2670263A (en) * | 1951-03-21 | 1954-02-23 | Gen Dyestuff Corp | Composition and process for dyeing polyethylene terephthalate fibers |
US2695832A (en) * | 1951-08-24 | 1954-11-30 | Gen Aniline & Film Corp | Dyeing of acrylic fibers with vat dyestuffs |
US2774647A (en) * | 1952-05-17 | 1956-12-18 | American Cyanamid Co | Dyeing of polyesters with vat dyes |
US2774649A (en) * | 1952-05-17 | 1956-12-18 | American Cyanamid Co | Dyeing of cellulose carboxylic acid esters with vat dyes |
US2798788A (en) * | 1952-06-21 | 1957-07-09 | Celanese Corp | Vat dyeing of cellulose ethers and esters |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US1900172A (en) | Treatment oe textile and other materials | |
US2428835A (en) | Dyeing of fabrics comprising cellulose acetate with an alcohol-thiocyanate swelling mixture | |
US2107526A (en) | Treatment of textile and other materials | |
US2182964A (en) | Coloration of textile and other materials | |
US1968856A (en) | Treatment of textile materials | |
US1968819A (en) | Dyeing of textile materials | |
US2950949A (en) | Process for dyeing and printing shaped structures of hydrophobic organic high polymers containing ester groups | |
US2619403A (en) | Emulsified volatile hydrocarbon liquids as printing paste thickeners | |
US2428836A (en) | Printing of cellulose acetate | |
US2798788A (en) | Vat dyeing of cellulose ethers and esters | |
US2072858A (en) | Production of colorations on materials | |
US2270756A (en) | Coloring composition | |
US3056643A (en) | Vat dyeing of polypropylene | |
US2681845A (en) | Acid vat dyeing of animal fibers | |
US1816766A (en) | Process of dyeing and printing cellulose esters | |
US1690481A (en) | Dyeing, printing, or stenciling of acetyl cellulose or products made therewith | |
US1716720A (en) | Treatment of yarns and fabrics | |
US1900168A (en) | Camille dreyfus | |
US2627449A (en) | Dyeing of polyester fibers with acid leuco vat dyes | |
GB341408A (en) | Colouration of textile and other materials | |
US1694413A (en) | Treatment of cellulose acetate | |
US2524073A (en) | Dyeing cellulose esters and ethers with alkaline aqueous solutions of leuco vat dyes containing diacetone alcohol | |
GB355363A (en) | Colouration of textile and other materials | |
US1978786A (en) | Coloration of textile materials | |
US1575958A (en) | Process of dyeing and printing of textile goods and other materials adapted to be impregnated |