US2067926A - Vat dye composition and manufacture thereof - Google Patents
Vat dye composition and manufacture thereof Download PDFInfo
- Publication number
- US2067926A US2067926A US62867A US6286736A US2067926A US 2067926 A US2067926 A US 2067926A US 62867 A US62867 A US 62867A US 6286736 A US6286736 A US 6286736A US 2067926 A US2067926 A US 2067926A
- Authority
- US
- United States
- Prior art keywords
- vat
- acid
- dye
- vat dye
- parts
- 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
- 239000000984 vat dye Substances 0.000 title description 102
- 239000000203 mixture Substances 0.000 title description 75
- 238000004519 manufacturing process Methods 0.000 title description 11
- 239000006072 paste Substances 0.000 description 62
- 150000003839 salts Chemical class 0.000 description 50
- 239000002253 acid Substances 0.000 description 43
- 239000000975 dye Substances 0.000 description 43
- -1 hydrocarbon radical Chemical class 0.000 description 40
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 39
- 238000007639 printing Methods 0.000 description 39
- 238000004043 dyeing Methods 0.000 description 33
- 239000000843 powder Substances 0.000 description 33
- 125000005907 alkyl ester group Chemical group 0.000 description 32
- 125000004432 carbon atom Chemical group C* 0.000 description 26
- 238000000034 method Methods 0.000 description 26
- 239000007787 solid Substances 0.000 description 24
- 239000000463 material Substances 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000000835 fiber Substances 0.000 description 20
- 239000000126 substance Substances 0.000 description 20
- 238000002360 preparation method Methods 0.000 description 19
- 150000003254 radicals Chemical class 0.000 description 19
- 229940032330 sulfuric acid Drugs 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- 230000008569 process Effects 0.000 description 16
- 239000004215 Carbon black (E152) Substances 0.000 description 15
- 229930195733 hydrocarbon Natural products 0.000 description 15
- 229910052783 alkali metal Inorganic materials 0.000 description 14
- 239000000725 suspension Substances 0.000 description 14
- 238000001035 drying Methods 0.000 description 13
- 239000004753 textile Substances 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 12
- 239000002270 dispersing agent Substances 0.000 description 11
- 238000011282 treatment Methods 0.000 description 11
- 239000007900 aqueous suspension Substances 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 229930006000 Sucrose Natural products 0.000 description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 9
- 230000009471 action Effects 0.000 description 9
- 239000004744 fabric Substances 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 9
- 150000007519 polyprotic acids Polymers 0.000 description 9
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 8
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 8
- 229940097275 indigo Drugs 0.000 description 8
- 239000000049 pigment Substances 0.000 description 8
- 229960004793 sucrose Drugs 0.000 description 8
- 150000001340 alkali metals Chemical class 0.000 description 7
- 239000007859 condensation product Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 159000000000 sodium salts Chemical class 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 230000003165 hydrotropic effect Effects 0.000 description 6
- 150000007522 mineralic acids Chemical class 0.000 description 6
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 229920001353 Dextrin Polymers 0.000 description 5
- FFVDYKZYOFPENN-UHFFFAOYSA-N S(=O)(=O)(O)O.C(C(C)C)[Na] Chemical compound S(=O)(=O)(O)O.C(C(C)C)[Na] FFVDYKZYOFPENN-UHFFFAOYSA-N 0.000 description 5
- 235000013877 carbamide Nutrition 0.000 description 5
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 5
- 238000000227 grinding Methods 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 150000008051 alkyl sulfates Chemical class 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 150000001720 carbohydrates Chemical class 0.000 description 4
- 235000014633 carbohydrates Nutrition 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- FYGDTMLNYKFZSV-MRCIVHHJSA-N dextrin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)OC1O[C@@H]1[C@@H](CO)OC(O[C@@H]2[C@H](O[C@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-MRCIVHHJSA-N 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000001488 sodium phosphate Substances 0.000 description 4
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 4
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 4
- 235000019801 trisodium phosphate Nutrition 0.000 description 4
- UGCDBQWJXSAYIL-UHFFFAOYSA-N vat blue 6 Chemical compound O=C1C2=CC=CC=C2C(=O)C(C=C2Cl)=C1C1=C2NC2=C(C(=O)C=3C(=CC=CC=3)C3=O)C3=CC(Cl)=C2N1 UGCDBQWJXSAYIL-UHFFFAOYSA-N 0.000 description 4
- CRDNMYFJWFXOCH-YPKPFQOOSA-N (3z)-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-YPKPFQOOSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000011872 intimate mixture Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 150000003460 sulfonic acids Chemical class 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- VMXWZRNWXZSSCE-VXPUYCOJSA-N (2z)-6-ethoxy-2-(6-ethoxy-3-oxo-1-benzothiophen-2-ylidene)-1-benzothiophen-3-one Chemical compound S/1C2=CC(OCC)=CC=C2C(=O)C\1=C1/C(=O)C2=CC=C(OCC)C=C2S1 VMXWZRNWXZSSCE-VXPUYCOJSA-N 0.000 description 2
- KTOQRRDVVIDEAA-UHFFFAOYSA-N 2-methylpropane Chemical compound [CH2]C(C)C KTOQRRDVVIDEAA-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- IOQBLCBBFOOOOS-UHFFFAOYSA-N S(=O)(=O)(O)O.C(CCC)[Na] Chemical group S(=O)(=O)(O)O.C(CCC)[Na] IOQBLCBBFOOOOS-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- YOCIQNIEQYCORH-UHFFFAOYSA-M chembl2028361 Chemical compound [Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=CC2=C1N=NC1=CC=CC=C1 YOCIQNIEQYCORH-UHFFFAOYSA-M 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical class C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 235000012738 indigotine Nutrition 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 2
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluenecarboxylic acid Natural products CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 2
- ZIRHAFGGEBQZKX-UHFFFAOYSA-N pentyl hydrogen sulfate Chemical compound CCCCCOS(O)(=O)=O ZIRHAFGGEBQZKX-UHFFFAOYSA-N 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-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
- 238000001179 sorption measurement Methods 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 150000003470 sulfuric acid monoesters Chemical class 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 229940124024 weight reducing agent Drugs 0.000 description 2
- RNJIWICOCATEFH-WCWDXBQESA-N (2e)-2-(1-oxobenzo[e][1]benzothiol-2-ylidene)benzo[e][1]benzothiol-1-one Chemical compound C1=CC=CC2=C(C(C(=C3/C(C4=C5C=CC=CC5=CC=C4S3)=O)/S3)=O)C3=CC=C21 RNJIWICOCATEFH-WCWDXBQESA-N 0.000 description 1
- HUGACAUYNJDGTB-ISLYRVAYSA-N (2e)-5-chloro-2-(5-chloro-7-methyl-3-oxo-1-benzothiophen-2-ylidene)-7-methyl-1-benzothiophen-3-one Chemical compound S1C=2C(C)=CC(Cl)=CC=2C(=O)\C1=C(C1=O)/SC2=C1C=C(Cl)C=C2C HUGACAUYNJDGTB-ISLYRVAYSA-N 0.000 description 1
- NDDLLTAIKYHPOD-ISLYRVAYSA-N (2e)-6-chloro-2-(6-chloro-4-methyl-3-oxo-1-benzothiophen-2-ylidene)-4-methyl-1-benzothiophen-3-one Chemical compound S/1C2=CC(Cl)=CC(C)=C2C(=O)C\1=C1/SC(C=C(Cl)C=C2C)=C2C1=O NDDLLTAIKYHPOD-ISLYRVAYSA-N 0.000 description 1
- PQMFVUNERGGBPG-UHFFFAOYSA-N (6-bromopyridin-2-yl)hydrazine Chemical compound NNC1=CC=CC(Br)=N1 PQMFVUNERGGBPG-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical class C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- NYADWZIPPHHYTR-UHFFFAOYSA-N 2-benzyl-3-butylnaphthalene-1-sulfonic acid Chemical class C(CCC)C=1C(=C(C2=CC=CC=C2C1)S(=O)(=O)O)CC1=CC=CC=C1 NYADWZIPPHHYTR-UHFFFAOYSA-N 0.000 description 1
- XOBRDIKDYBKVKH-UHFFFAOYSA-N 2-cyclohexylnaphthalene-1-sulfonic acid Chemical class C1=CC2=CC=CC=C2C(S(=O)(=O)O)=C1C1CCCCC1 XOBRDIKDYBKVKH-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- XQGDNRFLRLSUFQ-UHFFFAOYSA-N 2H-pyranthren-1-one Chemical class 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 1
- FXJVNINSOKCNJP-UHFFFAOYSA-N 4-methylbenzenesulfinic acid Chemical compound CC1=CC=C(S(O)=O)C=C1 FXJVNINSOKCNJP-UHFFFAOYSA-N 0.000 description 1
- ZLHGTHCCYUEAIK-UHFFFAOYSA-N 5,7-dibromo-2-(5,7-dibromo-3-hydroxy-1H-indol-2-yl)indol-3-one Chemical compound [O-]c1c([nH]c2c(Br)cc(Br)cc12)C1=[NH+]c2c(cc(Br)cc2Br)C1=O ZLHGTHCCYUEAIK-UHFFFAOYSA-N 0.000 description 1
- MPVDXIMFBOLMNW-ISLYRVAYSA-N 7-hydroxy-8-[(E)-phenyldiazenyl]naphthalene-1,3-disulfonic acid Chemical compound OC1=CC=C2C=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C1\N=N\C1=CC=CC=C1 MPVDXIMFBOLMNW-ISLYRVAYSA-N 0.000 description 1
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- 239000005711 Benzoic acid Substances 0.000 description 1
- NPHBPWBHHFJTHW-UHFFFAOYSA-N C(C)[Na].S(O)(O)(=O)=O Chemical compound C(C)[Na].S(O)(O)(=O)=O NPHBPWBHHFJTHW-UHFFFAOYSA-N 0.000 description 1
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- DXVROYJVFZSLSN-UHFFFAOYSA-N S(=O)(=O)(O)O.C(CCCC)[Na] Chemical compound S(=O)(=O)(O)O.C(CCCC)[Na] DXVROYJVFZSLSN-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
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- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
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- 238000010306 acid treatment Methods 0.000 description 1
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- 125000003545 alkoxy group Chemical group 0.000 description 1
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- WQZGKKKJIJFFOK-DVKNGEFBSA-N alpha-D-glucose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-DVKNGEFBSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003254 anti-foaming effect Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- BEHLMOQXOSLGHN-UHFFFAOYSA-N benzenamine sulfate Chemical class OS(=O)(=O)NC1=CC=CC=C1 BEHLMOQXOSLGHN-UHFFFAOYSA-N 0.000 description 1
- JEHKKBHWRAXMCH-UHFFFAOYSA-N benzenesulfinic acid Chemical class O[S@@](=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-N 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 235000010338 boric acid Nutrition 0.000 description 1
- 125000005619 boric acid group Chemical class 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- RPOLJNCRBSMWRU-UHFFFAOYSA-N dipentoxy-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical class CCCCCOP(S)(=S)OCCCCC RPOLJNCRBSMWRU-UHFFFAOYSA-N 0.000 description 1
- 238000010018 discharge printing Methods 0.000 description 1
- JFVXEJADITYJHK-UHFFFAOYSA-L disodium 2-(3-hydroxy-5-sulfonato-1H-indol-2-yl)-3-oxoindole-5-sulfonate Chemical compound [Na+].[Na+].Oc1c([nH]c2ccc(cc12)S([O-])(=O)=O)C1=Nc2ccc(cc2C1=O)S([O-])(=O)=O JFVXEJADITYJHK-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229910000078 germane Inorganic materials 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000004312 hexamethylene tetramine Chemical class 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 235000019239 indanthrene blue RS Nutrition 0.000 description 1
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 1
- COHYTHOBJLSHDF-BUHFOSPRSA-N indigo dye Chemical compound N\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-BUHFOSPRSA-N 0.000 description 1
- 239000004179 indigotine Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- CRDNMYFJWFXOCH-UHFFFAOYSA-N isoindigotin Natural products N1C2=CC=CC=C2C(=O)C1=C1C2=CC=CC=C2NC1=O CRDNMYFJWFXOCH-UHFFFAOYSA-N 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 description 1
- 229960004011 methenamine Drugs 0.000 description 1
- QXLPXWSKPNOQLE-UHFFFAOYSA-N methylpentynol Chemical compound CCC(C)(O)C#C QXLPXWSKPNOQLE-UHFFFAOYSA-N 0.000 description 1
- 229960001156 mitoxantrone Drugs 0.000 description 1
- FITZJYAVATZPMJ-UHFFFAOYSA-N naphthalene-2,6-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(S(=O)(=O)O)=CC=C21 FITZJYAVATZPMJ-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000001053 orange pigment Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 101150093826 par1 gene Proteins 0.000 description 1
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 1
- 229940107390 pentasol Drugs 0.000 description 1
- 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 1
- 239000003208 petroleum Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229940081066 picolinic acid Drugs 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- IVNFTPCOZIGNAE-UHFFFAOYSA-N propan-2-yl hydrogen sulfate Chemical class CC(C)OS(O)(=O)=O IVNFTPCOZIGNAE-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000010019 resist printing Methods 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- WGSONYKPKUBDQH-UHFFFAOYSA-M sodium 2-methylpropyl sulfate Chemical compound S(=O)(=O)(OCC(C)C)[O-].[Na+] WGSONYKPKUBDQH-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- CEHCOJSZSZWUIG-UHFFFAOYSA-M sodium;propyl sulfate Chemical compound [Na+].CCCOS([O-])(=O)=O CEHCOJSZSZWUIG-UHFFFAOYSA-M 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 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 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0077—Preparations with possibly reduced vat, sulfur or indigo dyes
-
- 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
Definitions
- This invention relates to vat dye compositions and processes for their manufacture.
- vat dyes are solid substances which are insoluble in water. In order to render them useful in the dyeing of textile fibers, they are, ordinarily converted to a water soluble form, as
- vat a solution or dye bath containing the vat dye in the reduced form 1 (a so-called vat) is first prepared, the material to be dyed is worked, in this solution or bath whereby the fiber takes up the reduced compound of the dye, and the material is then subjected to oxidation and otherfinishing treatments to coni vert the vat dye from the reduced to the unreduced form and further complete the fixing of the dye and finishing of the material.
- a reducing agent such as sodium hydrosulfite and alkali.
- the dye is applied to the mater al to be dyed while in the unreduced formpit is then subjected to a reducingv treatment whereby the dye is converted to the soluble form in the presence of the fiber and is taken up by the fiber, and his then subjected to oxidation and/or other finishing treatments to fix ,the dye on the fiber and complete the finishing of the material.
- vat dyes In dyeing with vat dyes by the latter method, one, of two procedures is usually followed, it depending upon whether the material is to be dyed a uniform or so-called solid color, or is to be dyed in, accordance with a pattern or design in one or more colors. If the material is to be dyed a solid color, the so-called pigment padding or pad and jig process is ordinarily employed. If the material is to be dyed in accordance with a pattern or design, the so-called printing process is generally utilized.
- the pigment padding process of dyeing with vat dyes generally involves passing the textile material to be dyed through an aqueous suspension or so-called padding bath containingthe unreduced vat dyein finely divided-form suspended in a suitable suspension medium (such as water, which mayor may not also contain a gum or thickener and other substances such as an assistant, sodium sulfide, etc.), whereby the fiber mechanically picks up the particles of insoluble dye; subsequently working the textile material, having the particles of dye mechanically attached thereto, in-a reducing bath (jigging) whereby the dye isreduced to the soluble form andis taken (absorbed and/or adsorbed) by the fiber; and finally subjecting the material to oxidation and'finishing treatments to reconvert the dye to the insoluble form, fix it on the fiber,
- a suitable suspension medium such as water, which mayor may not also contain a gum or thickener and other substances such as an assistant, sodium sulfide, etc.
- vat dye printing pastes contain, in addition to the unreduced vat dye, substances which in themselves do not reduce the vat dye under the conditions of the printing operation but which in the subsequent operations react with the dye tojconvert it to the soluble form (such as sodium fcrmaldehydesulfoxylate and potassium carbonate), other substances or assistants which promote the reduction of thedye and/or absorption of the reducedcompound' by the fiber, and
- the vat dye in the printing paste is subjected to a preliminary reductionbefore applying the printing paste to the fabric.
- the fixing treatment usually comprises subjectingthe printed fabric to a short treatment with wet steam while ex eluding air (so-called steaming or ageing), whereby the vat dye is reduced (for example, by the action of the -sodium-iormaldehyde-sulfoxylate and potassium carbonate), or if prereduced its reduction'is .rendered more com,-
- vat dyes in the Ordinary unreduced, solid form are not only insoluble in water but they are not readily wetted by water, and even when ground with water for a considerable length of time do not disperse uniformly in the extremely finely divided form desired for use in dyeing by the pigment. padding and printing processes. They therefore usually come upon the market in the form of aqueous suspensions or so-called pastes which generally contain 10 to per cent. of the vat dye, a small amount of adispersing. agent such as Leukanol (a condensation On Y of a precipitate of the dye, as obtained for exam.- ple in its manufacture or by precipitation in the finely divided form from a vat or from a sulfuric acid or other solution.
- Leukanol a condensation On Y of a precipitate of the dye, as obtained for exam.- ple in its manufacture or by precipitation in the finely divided form from a vat or from a sulfuric acid or other solution.
- vat dye powders have. been produced by drying pastes of vat .dyes. In some cases dispersing agents havev been incorporated into the vat dye pastes prior to the drying.
- vat dye powders heretofore known to the art are of consequence in connection with their use in dyeing with a reduced bath or vat, owing tothe greater, period of time required for complete solution of -the vat dye in the course of preparation of the bath and its resulting increased cost of dyeing, they do not prevent the use of such powders in certain connections such as dyeing by the. reduced bath or vat process.
- the said objections areordinarily of so great importance as to render such powders of little value for use in the latterprocesses. Thisis due to the fact that, in
- the insoluble vat dye is ordinarily converted to the soluble-form in contact with the fiber to be dyed, and consequently uniformity of dispersion of the dye in-the padding liquor or printing paste is required to avoid unevenness of'shade and/or streaking, extremely fine subdivision 'of the in-
- the present invention is based upon the discovery that the readily soluble salts of the hereindescribed acid alkyl esters of polybasic inorganic acids possess a combination of properties which render them of particular value for the production and manufacture of vat dye preparations in the form of suspensions, pastes and powders, and especially for the manufacture of vat dye powders which can be used as initial material for the preparation of dye baths and pastes for dyeing textile fibers, in particular by printing and pad and jig processes.
- the soluble salts of the said reaction products of sulfuric acid or chlorsulfonic acid upon the aliphatic monohydric alcohols which contain 5 or less carbon atoms which products are considered to be acid alkyl sulfates corresponding with the formula ROSOaH (in which R. is a hydrocarbon radical containing not morethan 5 carbon atoms), as well as others of the hereindescribed soluble salts of acid alkyl esters of inorganic polybasic acids, have the faculty of rapidly entering into solution in water and other aqueous suspension media for vat dyes.
- the invention accordingly comprises the compositions havingthe-properties, ingredients and proportions of ingredients, exemplified in the compositions hereinafter disclosed, and the processes comprising steps and their relation exemplified in the processes hereinafter disclosed.
- the scope of the invention will be indicated in the appended patent claims.
- vat dye is mixed with one or more of the soluble salts of the acid alkyl esters of polybasic inorganic acids more fully identified hereinafter.
- the said preparation of the compositions of the present invention may be carried out in a number of ways, for example, by intimately grinding the salt of the acid alkyl ester in the solid form with a solid form of the vat dye.
- compositions of the present invention are preferably prepared by dissolving the said salt of the acid alkyl ester in an aqueous dispersion or suspension of the vat dye, which preferably contains a dispersing agent, with or with- 'out addition of fillers and/or other substances desired in'the final product, and drying the resulting mixture, preferably with agitation and preferably by evaporation to substantial dryness.
- the vat dye which preferably contains a dispersing agent
- fillers and/or other substances desired in'the final product preferably with agitation and preferably by evaporation to substantial dryness.
- lower alkyl hydrocarbon radical denotes an aliphatic hydrocarbon radical containing .a maximum of 5 carbon atoms.
- salts of the said acidalkylesters which contain a radical of sulfuric, boric, phosphoric or thiophosphoric acid, and especially of sulfuric or phosphoric acid, are of particular interest in connection with the present invention.
- These par- 1 tial esters (which are herein designated as acid alkyl esters) may be represented by the formula (Emir-Atom).
- R represents an aliphatic hydrocarbon radical which contains less than 6 carbon atoms
- A represents the residue of the inorganic acid (as for example the radical $02, the radical PO,
- n the number of hydrogen atoms
- the uncombined polybasic acid from which the ester is derivable which are replaceable by a metal (hereindesignated asrepl aceable hydrogen atoms), and :c is one or more but not greater than n-1.
- the parent polybasic inorganic acid has not been replaced.
- the alkyl ester salts employed in accordance with the present invention comprise the solublesalts of the herein-described acid alkyl esters; e. g., those resulting from the combination of the said acid alkyl esters with any suitable metal or base, including the organic bases, producing salts having good solubility and also preferably a finely crystalline or amorphous form in the solid For example, alkali metal, alkali earth state.
- metal, ammonium, etc. salts may be employed or the salts formed by the interaction of the-said acid alkyl esters with such organic bases as alkyl amines (particularly the hydroxy alkayl amines), pyridine, guanidine, urea or other salt-forming organic ammonium bases.
- alkyl ester salts employed in accordance with the present'invention may be prepared in any manner well known to the art; as for example by the treatment of the corresponding alcohol, in the presence or absence of a solvent or diluent, with a suitable inorganic reagent (such' as phosphorus chloride or oxychloride, concentrated sulfuric acid and/or chlorsulfonic acid,
- a suitable inorganic reagent such' as phosphorus chloride or oxychloride, concentrated sulfuric acid and/or chlorsulfonic acid
- boric acids diamyl dithiophosphoric acids
- alkali metal salts of the sulfuric acid mono esters of the various alcohols which contain not more than 5 carbon atoms, in-
- the salts of the monoalkyl sulfuric acids which contain from 3 to 5 carbon atoms in the alkyl group are of especial value in the production of vat dye composition in accordance with the present in vention.
- the alkyl group comprises an iso-alkyl radical (as for example, an isopropyl radical:
- CH- cmonz etc. are somewhat superior in their action tothose in which the alkyl group is a normal or straightchain radical, although they are somewhat more hygroscopic than those in which the alkyl group is anormal or straight-chain radical.
- the said sulfuric acid mono alkyl esters may be prepared in any manner well known to the of 'chlorsulfonic acidto form the sulfuric acid mono ester of the alcohol, the mixture then may be blown with air to remove hydrogen chloride formed, and subsequently stirred with water.
- salts of acid alkyl esters may also be employed in accordance with the present invention; as for example the salts of alkali metals or organic bases with the commercially available and cheap mixtures of alkyl sulfuric acids resulting from the sulfuric acid treatment of gaseous and lighter liquid unsaturated hydro carbons, such as mixtures produced in the recovery and removal of unsaturated hydrocarbons in the production and purification of gasoline in the so-called cracking process'of petroleum,
- the vat dye is preferably 'ent, anti-foaming, assisting, wetting, catalytic,
- enoly'zing, or other suitable action in the subse-v quent use of the compostions may also be incorporated into the compositions of thepresent intreated in the highly dispersed form.
- a suitable dispersing agent is preferably included in the dis-v persion or suspension so as to aid in preventing precipitation and-agglutination of the dye particles during the drying and to increase the fluidity and render easier the'incorporation of the monoalkyl sulfuric acid salt.
- dispersing agents which may be employed for this purpose there may be mentioned for example, the sulfonic acids of benzene, hydroxybenzen'es, naphthalene,
- hydroxynaphthalenes their nuclear alkyl, nu.-. clear aralkyl and hydrogenated derivatives, as,
- aldehyde condensation products thereof (as for example 2,6-naphthalenedisulfonic acid, 1.7-naphthalenedisulfonic acid, 2.8- naphthalenedisulfonic acid, isopropylnaplithalenesulfonic acids, dibutylnaphthalenesulfonic acids, amylna phthalcncsulfonic acids, butylbenzylnaphthalenesulfonic acids, cyclohexylnaphthalenesulfonic acids, methylene-di (betanapth'alenesu1- ionic acid), acetaledi (beta naphthalenesulfonic acid), benzal-di beta-naphthalenesulfonic acid),
- compositions may be in a A more satisfactory form for subsequent use, the
- the paste, with or without preliminary. evaporation may be admixed with a, suitable hydrateforming soluble salt-in an anhydrous condition and the admixture stirred to produce a dryproduct.
- the dry products may be disintegrated into a powder in any suitable manner,
- the amount-of salt of acid alkyl ester employed inthe'preparation of the compositions of the'present invention maybe varied over-a considerable range, depending in part upon the nature and concentration of the vat dye in the composition, the use to which the composition is to be put, and whether or notother diluents andother materials having a catalytic, assisting,
- wetting, enolyzing, dispersing, or other action are included in the composition.
- wetting, enolyzing, dispersing, or other action are included in the composition.
- an ideal vat dye composition in dry form is obtained by replacing all of the water in a vat dye paste with an equal amount of said alkyl estersalt, in which casethe' composition of the powder may be for example:
- protective colloids other substances included in the general class of so-called protective colloids also may be used; as well as other products which do not cause precipitation of suspended vat dye particles or otherwise produce specky printing pastes (as for example, urea, variousother highly soluble amides, etc).
- vat dye powder compositions of the present invention are to be employed in the preparation of vat dye printing pastes and it is desired to take advantage of the solubilizing action of the said alkyl ester salts, andespecially the monoalkyl sulfuric acid salts, in the preparation of the printing pastes and-their assisting action in the printing operation, a larger amount of said salts will ordinarily be employed than would be necessary merely for the preparation of a readily dispersible vat dye powder.
- the specific amount of of printing pastes with the aid of vat dye powders of the present invention that the printing pastes frequently show signs of prereduction, even in the absence of printing catalysts or reduction accelerators employed in the art, such as aoaasae celerators," hydrotropic and/or enoiyzing substances, in addition to .or in replacement of part of other diluents.
- hydrotropic substances are to be understood not only the substances specially enumerated by Neuberg and "Iamba chemische Zeitchrift, vol. 76, 1916, page 107 if., V 15 and Tamba, Biochemische Zeitchrift, vol. 145,
- salt of ethyl sulphonic acid potassium or soexamples of such substances the following may be mentioned: urea, substituted ureas, thiourea, hexamethylene tetramine, the potassium dium isovaleratathe alkali metal salts of the following acids: isobutyric acid, phenylacetic acid, benzoic acid, o-toluene-carboxylic acid,
- toluene-sulphonic acid the benzene sulphinic acids, 1.4-toluene sulphinic acid, naphthalene sulphonic acids, aniline sulphonic acids and substitution products thereof, naphthylamine sulfonic acids (as for example, l-amino-naphthae ,lene-3.6.8-trisulf0nic acid) picolinic acid, hydro aromatic carboxylic or suiphonic acids, and the a which It will be further noted that substances like. are not, strictly speaking, hydrotropic substances ,but which possess enolyzing propertiesarefincluded, as for example l-naphthalene sulphonic acid (sodium salt).
- vat dye powders prepared in accordance withthe particular advantage in 5 connection with vat dyes of the indigoid and thioindigoid series, inasmuch as they tend to minimize or prevent isomerization of V the reduced vat dye to theketo form.
- vat dye compositions of the present in- H vention are particularly valuable for dyeing and (unbleached celfabrics and the like) inasmuch as the dyeings and prints ob tained" with the aid of such compositions have exprinting so-called gray goods" ceedingly :high tinctorial value and excellent penetration,
- vat dyes of all types including those derived from anthraquinone, 'indophenois, various indigoid. thioindigoid and indirubin compounds, etc.; as ior example, indanthrones, pyranthrones, fia'vanthrones, dibenzanthrones, isodibenzanwt-lirones, perylene quinones, anthanthrones, di-
- Example 1 .400. parts of indigo paste (containing 20 per cent. of pure indigo as shown by indigotine titration and resulting from the pre-.
- the powder When employed for the preparation of an indigo vat with the aid of the usual reducingagents (for example, alkaline sodium hydrosulfite), the powder reduces very rapidly andproduces a clear vat which dyes cotton even, blue shades of high tinctorial value.
- the usual reducingagents for example, alkaline sodium hydrosulfite
- the powder reduces very rapidly andproduces a clear vat which dyes cotton even, blue shades of high tinctorial value.
- an equal amount of normal amyl sodium sulfate, (C5H1'1OSOsNa) or of any of the other salts of acid alkyl esters hereinbefore mentioned, and especially lower monoalkyl sulfuric acid soluble salts may be used.
- Example 2 To 100 parts of the chlorinated indanthrcne vat dye known as National Carbanthrene Blue 308 (Color Index No. 1114) in the formof an aqueous suspension or commercial paste'vcontaining 18 per cent of total dye solids,
- the product either in the form of paste or powder, gives uniform dyeings of high tinctorial value when employed to dye fabrics in accordance with standard practice, and especially by the pad andjig method. Instead of sec rial "is dissolved, and is then evaporated to'dryness, ground to a powder, and screened through a 60 mesh screen. The resulting product is a'violet colored powder Whichisfreadily dispersed upon; 1 adding to water and is especially suitable for dyeing. fibers by the pad andjjigfprocess.
- the powderlis' made intoqa printing paste containing the usual additional ingredients, and the resulting I paste is. employed to print a textilefabric which 10,
- the potassium salt of the acid sulfuric ester of dimethyl ethyl carbi'nolor readilysoluble salts, ,of any of the otheracid esters above disclosed may be" used;
- Example '4.-' 10(i"'p artsof National Carbam threne Violet 2R Paste (cf. Example 3) are mixed with 25 parts of cane sugar and 68 parts of iso- ,propyl sodium sulfate v on," V I germane) C a,
- Example 5 l parts" i the dye known as NationalVat Orange R (Color Index 1217) invtheform'of an aqueous paste containingaboutll" per cent of dye solids, are mixed withZ parts of Leukanol and 87 parts ofethyl' sodium, sulfate (C2Hs0SOaNa) until solution'of the latter is complete. The resulting suspension is evaporated to dryness, ground and screened. instead ofthe ethyl sodium sulfate other salts of thelower alkylsulfates may b'e employed.
- Vat Orange R powder -100 parts of a Vat Orange R powder are thus obtained, which, when employed in the preparation of a printing paste (for-example by mixing150 partsof the powder-with 200parts of British .gui'n, 140 partsof potassium carbonate, 80 parts of sodium formaldehyde sulfoxylate, 50 parts of glycerin, and 380parts of water). and utilized in the printing .of. cotton in accordance withthe usual procedure, produces prints which in heavy shades'are about 20m 25 per cent greater in strength than corresponding prints made without the alkylsodium sulfate.
- alkyl esters whichcontain-an iso-radic'al (as for It may be; noted that the soluble salts of acid example, the isopropyl radical, the isobutyl radical, etc.) are preferably employed in connection with'yat dyes of the f thioindigoid series when the latter are to .be employed for the preparation of printing. pastes, in view of" their superior action inthe printing process. i
- potatssium Z-carboxy-bnzophenone- Gil 4"-sulfonate acts as an assistant or adjuvant
- Example 7 100 parts of the vat" dye known as National Vat Pink FF (6.6'-dichl0r'-4;.4-dimethyl thioindigo) in the form of an aqueous j paste or suspension containing 15 per cent of dye solids, there are added 2 parts of Leukanol, 64
- Example 9 To 100 parts of National Carbanthrene Blue GCD Double. Paste (Color Index .1113) containing 16.5 per cent of dye solids and 1 per cent of Leukanol, there are added 50 parts of isobutyl sodium sulfate and 32.5 parts of urea, and the mixture isstirred until the latter are dissolved. The resulting suspension is evaporated to dryness, ground and screened. A very readily dispersible vat powder is obtained which is suitable for printing as well as dyeing.
- compositions of the present invention it is not necessary to employ a previously prepared dyestufi paste but the filter cakes and other separated forms of the dye may be employed; as for example, the press cakes resulting from the filtration of aqueous suspenas illustrated by the following example;
- Example 11-2 parts of the sodium salt of anthraquinone-Z-sulfonio acid are dissolved in 2031 parts of water, with the aid of heat if necessary, 100 parts of dextrine are added, and
- vat dyes disclosed may be replaced by any other vat dye; as for example: a
- fcor dance with the present invention by admixing a suitable hydrate forming soluble salt in an anhydrous condition with the paste, whereby a dry product is formed by formation of a hydrate of said salt.
- a suitable hydrate forming soluble salt in an anhydrous condition with the paste, whereby a dry product is formed by formation of a hydrate of said salt.
- trisodium phosphate, sodium sulfate, sodium acetate or other suitable hydrate-forming soluble salts may beadmixed in an anhydrous condition (in the anhydrous form or a partially dehydrated'form) by stirring with a vat dye composition of the present invention in the form of a paste, preferably in the form of a partially
- the resulting dry mixture maybe ground and screened to form a powder.
- Example 12 3-300 parts of indigo paste (containing 20 per cent of pure indigo, as shown by indigotin titration), are stirred with 2 parts of dry Leukanol until a thin fluid paste is obtained; parts of normal butyl sodium sulfate are then added, the mixture is stirred until solution of the alkyl sulfate is complete, and the resulting mixture is evaporated with stirring until a thick paste containing about 19 to 20 per cent of water is formed. 15 parts of anhydrous trisodium phosphate are then added and the mass is intimately mixed until a dry product is obtained. There is thus produced 100 parts of the dry composition containing 60 per cent of indigo. Upon grinding the product and screening through a screen of fine mesh, a fine dry powder is obtained. which disperses very readily and may be used for all dyeing purposes.
- the mixture is stirred to dissolve the sol- "uble material, and then evaporated with stirring until a paste containing approximately 16 per cent of'water is produced. "The resulting paste is intimately'mixed withl2 parts of anhydrous. trisodium phosphate whereby a dry product is obtained, which, when ground and screened, results in a bright orange powder having advantageous properties similar to, those of the prodnot of Example 6.
- vat dye compositions of the present invention containing 'soluble salts of acid alkyl esters may also be utilizedas components of discharge and resist printing preparations as well as of the dyeing and printing compositions above described.
- This application is a division of my application Serial No. 673,031, filed May 26, 1933, for Art of dyeing and coloring, and is in part a continuation of my application Serial No. 673,030, filed 1 . May 26, 1933, for Vat dye composition.
- a vat dye composition comprising a vat dye and a soluble salt of an alkylsulfuric acid corresponding with the formulaROSOfl-Lin which R represents a hydrocarbon radical containing less than 6 carbon atoms.
- a vat dye composition comprising a vat dye and a soluble salt of an alkyl sulfuric acid corresponding with the formula ROSOsH, in which g R represents a hydrocarbon radical containing less than 6 carbon atoms, said composition being in the form of powder which dispersesreadily when added to water-. 7 I a 3.
- Avat dye composition in solid form for use in coloring, dyeing andtextile printing which comprises a vat dye, a dispersing agent, and a soluble salt of an alkyl sulfuric acidcorrespondthe NH4 radical.
- a vat dye composition in the dry solid form comprising a vat dye'and an alkali metal salt of an alkyl sulfuric acid containing 3 to 5 carbon atoms in the alkyl group, said salt corresponding with the formula ROSOaM, in which R repre'' sents a saturated hydrpcarbonradical containing from 3 to 5 carbon atoms, and M represents an alkali metal.
- a vat dye composition in solid form adapted for use in textile printing which comprises a vat dye, an alkali metal salt of analkyl sulfuricacid containing less than 6 carbon atoms, said salt corresponding with the formula RQSOaM, in
- R represents an open-chain hydrocarbon radical containing less than 6 carbon atoms and M represents an alkali metal, and a material selected from the class of carbohydrates, printing catalysts, assistants, 'hydrotropic substances,-.
- a 'vat dye composition in, solid form'for use in textile printing whichv comprise's'avat dye and the sodium salt of an alkyl sulfuric acid containing less than 6 carbon atoms in the'alkyl group, said salt corresponding with the formula ROSOaNa, in which R represents an alkyl radical containing less than 6 carbon atoms, such as is obtainable by drying an aqueous mixture comprising the vat dye and the sodium salt of the alkyl sulfuric acid.
- a vat dye composition in solid form adapted for use in textile printing which comprises a vat dye selected from the group of anthraquinone, indigoid and thioindigoid vat dyes, and the sodium salt of an alkyl sulfuric acid containing 3 to 5 carbon atoms in the alkyl group, said salt corresponding with the formula ROSOaNa, in which R represents a saturated hydrocarbon radical containing 3 to 5 carbon atoms.
- a vat dye composition in dry solid form which comprises an intimate mixture of a vat dye, an aldehyde condensation product of an aromatic sulfonic acid, a carbohydrate and a highly soluble salt of a monoalkyl sulfuric acid containing less than 6 carbon atoms.
- a vat dye composition in dry solid form which comprises an intimate mixture of a vat dye, a formaldehyde condensation product of a naphthalene sulfonic acid, a carbohydrate, and sodium isobutyl sulfate.
- a method of making a vat dye composition which comprises incorporating a, soluble salt of an alkyl sulfuric acid corresponding with the formula ROSOsH, in which R represents a hydrocarbon radical containing less than 6 carbon atoms, into an aqueous suspension comprising a vat .dye and a dispersing agent, and drying the mass.
- a method of making a vat dye composition which comprises incorporating a soluble salt of an alkyl sulfuric acid having the formula ROSOaM, .in which R represents an open-chain hydrocarbon radical containing less than 6 carbon atoms and M represents an alkali metal, into an aqueous suspension comprising a vatdye and an aldehyde condensation product of a naphthalene sulfonic acid as a dispersing agent, and drying the mass. 4
- a vat dye composition in the form of an aqueous paste comprising a vat dye, an aldehyde condensationv product of a naphthalene sulfonic acid as a dispersing agent, and a soluble salt of 1 an alkyl sulfuric acid containing less than 6 carbon atoms in the alkyl group, saidsalt corresponding with the formula ROSOaM, in which R represents an open-chain hydrocarbon radical containing less than 6 carbon atoms, and M represents an alkali metal.
- a vat dye composition in the form of an aqueous paste comprising a vat dye, a formaldehyde condensation product of a naphthalene sulfonic acid and an-alkali metal salt of an alkyl sulfuric acid containing3 to 5 carbon atoms in the alkyl group, said salt corresponding with the formula ROSOsM, in which R represents a sat-. urated hydrocarbon radical, containing from 3 to 5 carbon atoms, and M represents an alkali metal.
- a vat dye composition in the form of an aqueous paste comprising a vat dye, a dispersing agent, and a soluble salt'of an acid alkyl ester consisting on the one hand of a radical of an inorganic polybasic acid in which at least one of the replaceable hydrogen atoms is present and on the other hand 'of one or more lower alkyl hydrocarbon radicals directly linked to the inorganic radical; 17.
- a vatdye composition comprising a vat dye and a soluble salt of an acid alkyl ester consisting on the one hand of a radical of an inorganic polybasic acid in which at least one of the replaceable hydrogen atoms is present and on the other hand of one or more lower alkyl hydrocarbon radicals directly linked to the inorganic radical.
- a vat dye composition in the dry solidform comprising a vat dye and an alkali metal salt of an acid alkyl ester consisting on the one hand of a radical of an inorganic polybasic acid in which at least one of the replaceable hydrogen atoms is present and-on the other hand of one or more lower alkyl hydrocarbon radicals directly 1g linked to the inorganic radical.
- a vat dye composition in dry solid form 19.
- Amethod of making a vat dye composition which comprises incorporating a soluble salt of an acid alkyl ester into an aqueous suspension comprising a vat dye and a dispersing agent, and drying the mass, said acid alkyl ester consisting on the one hand of a radical of an inorganic polybasic acid in which at least one of the replaceable hydrogen atoms is present and on the other hand of one or more lower 'alkyl hydrocarbon radicals :directly linked to the inorganic radical.
Description
Patented Jan. 19, 1937 VAT DYE COMPOSITION AND MANU-s FACTURE THEREOF Jean G. Kern, East Aurora, N. Y, assignor to National Aniline & Chemical Company, Inc., New York, N. Y., a corporation of New York UNITED STATES No Drawing. Original application May 26, 1933,
Serial No. 673,031.
Divided and this application February 7, I936, Seral No. 62,867
b 20 Claims. This invention relates to vat dye compositions and processes for their manufacture.
'Fhe' dyeing of textile fibers with'vat dyes in t :volves absorptionor adsorption by the fiber of the dye in a soluble form followed by a fixing treatment, to render insoluble the dye taken up by the fiber, and other finishing operations for removing undesired residual material. It is well I known that vat dyes are solid substances which are insoluble in water. In order to render them useful in the dyeing of textile fibers, they are, ordinarily converted to a water soluble form, as
for example, by treatment with a reducing agent, such as sodium hydrosulfite and alkali. b Two general methods are ordinarilyemployed in practice for dyeing fibers with vatdyes. In accordance with one method, a solution or dye bath containing the vat dye in the reduced form 1 (a so-called vat) is first prepared, the material to be dyed is worked, in this solution or bath whereby the fiber takes up the reduced compound of the dye, and the material is then subjected to oxidation and otherfinishing treatments to coni vert the vat dye from the reduced to the unreduced form and further complete the fixing of the dye and finishing of the material. In accordance with another method, the dye is applied to the mater al to be dyed while in the unreduced formpit is then subjected to a reducingv treatment whereby the dye is converted to the soluble form in the presence of the fiber and is taken up by the fiber, and his then subjected to oxidation and/or other finishing treatments to fix ,the dye on the fiber and complete the finishing of the material.
In dyeing with vat dyes by the latter method, one, of two procedures is usually followed, it depending upon whether the material is to be dyed a uniform or so-called solid color, or is to be dyed in, accordance with a pattern or design in one or more colors. If the material is to be dyed a solid color, the so-called pigment padding or pad and jig process is ordinarily employed. If the material is to be dyed in accordance with a pattern or design, the so-called printing process is generally utilized.
The pigment padding process of dyeing with vat dyes generally involves passing the textile material to be dyed through an aqueous suspension or so-called padding bath containingthe unreduced vat dyein finely divided-form suspended in a suitable suspension medium (such as water, which mayor may not also contain a gum or thickener and other substances such as an assistant, sodium sulfide, etc.), whereby the fiber mechanically picks up the particles of insoluble dye; subsequently working the textile material, having the particles of dye mechanically attached thereto, in-a reducing bath (jigging) whereby the dye isreduced to the soluble form andis taken (absorbed and/or adsorbed) by the fiber; and finally subjecting the material to oxidation and'finishing treatments to reconvert the dye to the insoluble form, fix it on the fiber,
and further complete the finishing ofthe material.
The printing process of dyeing textile fabrics generally involves applying a so-called printing paste to the fabric in the form of a design (for example, by means of a screen, a stencil or an engraved roll), and then subjecting the printed fabric to further treatment to fixthe dye. In general, vat dye printing pastes contain, in addition to the unreduced vat dye, substances which in themselves do not reduce the vat dye under the conditions of the printing operation but which in the subsequent operations react with the dye tojconvert it to the soluble form (such as sodium fcrmaldehydesulfoxylate and potassium carbonate), other substances or assistants which promote the reduction of thedye and/or absorption of the reducedcompound' by the fiber, and
suitable gums or thickeners. In some cases, as in printing with diificultly reducible vat dyes, the vat dye in the printing paste is subjected to a preliminary reductionbefore applying the printing paste to the fabric. The fixing treatment usually comprises subjectingthe printed fabric to a short treatment with wet steam while ex eluding air (so-called steaming or ageing), whereby the vat dye is reduced (for example, by the action of the -sodium-iormaldehyde-sulfoxylate and potassium carbonate), or if prereduced its reduction'is .rendered more com,-
plete, and the reduced .dye is taken up by the fiber; and then subjecting the printed fabric to oxidizing, washing and other finishing treatments.
The vat dyes in the Ordinary unreduced, solid form are not only insoluble in water but they are not readily wetted by water, and even when ground with water for a considerable length of time do not disperse uniformly in the extremely finely divided form desired for use in dyeing by the pigment. padding and printing processes. They therefore usually come upon the market in the form of aqueous suspensions or so-called pastes which generally contain 10 to per cent. of the vat dye, a small amount of adispersing. agent such as Leukanol (a condensation On Y of a precipitate of the dye, as obtained for exam.- ple in its manufacture or by precipitation in the finely divided form from a vat or from a sulfuric acid or other solution.
-- Vat dye pastes as ordinarily prepared,however,
have a number of disadvantages from the standpoint of economy. For example they contain a" preponderating quantity of material which .has
- no dyeing action (mainly water) which addsconsiderably to the cost of transportationand handling of the active dye material; care must be exercised in the transportation of the pastes in order to avoid loss of the material by leakage of the container; precautions must'be taken in' winter to prevent freezing; care must be exercised in the storage of'the paste tojavoid drying? out and formation "of an insoluble crust which does notredisperse and which frequently appears as specksin the paste causing imperfections'in the resulting dyeings and prints; and upon standing the pastes frequently settle andrequire thorough agitation to produce uiform dispersion, which is time-, and labor-consuming- Various attempts heretofore have been made to provide vat dyes in the dry or powder'form which will wet and disperse to a sufficient'extent to be useful for the dyeings of textile fibers by all processes. Thus, vat dye powders have. been produced by drying pastes of vat .dyes. In some cases dispersing agents havev been incorporated into the vat dye pastes prior to the drying. While the'resultingpowders frequently have improved wetting and dispersing qualities I as compared with powders produced by grinding dry vat dye stuffs, when converted into a paste byfs'lurrying with water and/or when incorporated in a printing paste,-they do .not produce" a dispersion of the vat dye which possesses the" suitability for dyeing comparable with that of the ordinary commercial vat dye pastes. The principal'difiiculty with such powders appears tojbe the failure of-the vat dye, upon being added to water or a printing paste, to revert to its'original degree of fineness and uniformity of dispersion, which failure is apparently brought "about, in part'at least,
by changes inthe physical condition of the vat dye'during the drying. a
While the foregoing objections to the vat dye powders heretofore known to the art are of consequence in connection with their use in dyeing with a reduced bath or vat, owing tothe greater, period of time required for complete solution of -the vat dye in the course of preparation of the bath and its resulting increased cost of dyeing, they do not prevent the use of such powders in certain connections such as dyeing by the. reduced bath or vat process. In connection with the dyeing of textile material, by the pigment padding and. printing processes, however, the said objections areordinarily of so great importance as to render such powders of little value for use in the latterprocesses. Thisis due to the fact that, in
\ both the pigment padding and printing processes,
the insoluble vat dye is ordinarily converted to the soluble-form in contact with the fiber to be dyed, and consequently uniformity of dispersion of the dye in-the padding liquor or printing paste is required to avoid unevenness of'shade and/or streaking, extremely fine subdivision 'of the in- The present invention is based upon the discovery that the readily soluble salts of the hereindescribed acid alkyl esters of polybasic inorganic acids possess a combination of properties which render them of particular value for the production and manufacture of vat dye preparations in the form of suspensions, pastes and powders, and especially for the manufacture of vat dye powders which can be used as initial material for the preparation of dye baths and pastes for dyeing textile fibers, in particular by printing and pad and jig processes. Thus, the soluble salts of the said reaction products of sulfuric acid or chlorsulfonic acid upon the aliphatic monohydric alcohols which contain 5 or less carbon atoms, which products are considered to be acid alkyl sulfates corresponding with the formula ROSOaH (in which R. is a hydrocarbon radical containing not morethan 5 carbon atoms), as well as others of the hereindescribed soluble salts of acid alkyl esters of inorganic polybasic acids, have the faculty of rapidly entering into solution in water and other aqueous suspension media for vat dyes. They furthermore have little or no tendency to foam and lather,'which is in contradistinction to the foaming and lathering action of the sulfuric acid esters of alcohols of high molecular weight (e. g.,'lauryl'sulfate). In addition they act as dyeing assistants, e. g;, in the absorption or adsorption of the. reduced compounds of the vat dyes by the fiber, and in the penetration of woven fabric by'the reduced compounds of the vat dyes during the 'developing'steaming or ageing operations.
The invention accordingly comprises the compositions havingthe-properties, ingredients and proportions of ingredients, exemplified in the compositions hereinafter disclosed, and the processes comprising steps and their relation exemplified in the processes hereinafter disclosed. The scope of the invention will be indicated in the appended patent claims.
In the preparation of a vat dye composition of the present invention, a vat dye is mixed with one or more of the soluble salts of the acid alkyl esters of polybasic inorganic acids more fully identified hereinafter. The said preparation of the compositions of the present invention may be carried out in a number of ways, for example, by intimately grinding the salt of the acid alkyl ester in the solid form with a solid form of the vat dye. The compositions of the present invention are preferably prepared by dissolving the said salt of the acid alkyl ester in an aqueous dispersion or suspension of the vat dye, which preferably contains a dispersing agent, with or with- 'out addition of fillers and/or other substances desired in'the final product, and drying the resulting mixture, preferably with agitation and preferably by evaporation to substantial dryness. I have found, by removing water, as by evaporation to substantial dryness, from an aqueous. disperson or suspension of a vatdye containing one or more of the soluble salts of thesaid acid alkyl esters, that the final product has the appearance of a solid dispersed suspension. In those cases where a very large amount of the salt of the acid alkyl ester is employed, a part of said salt may crystallize during the evaporation, but the crystals are so finely divided and evenly distributed throughout the whole composition, that the product appears to be substantially homogeneous.
action products resulting from the interaction of an aliphatic monohydric alcohol containing or less carbon atoms with a polybasic inorganic acid or suitable derivative thereof and which are considered to be partial esters of polybasic inorganic acids consisting, on the one hand, of a radical of an inorganic polybasic acid in which at least one of the replaceable hydrogen atoms ispresent and,
the expression lower alkyl hydrocarbon radical denotes an aliphatic hydrocarbon radical containing .a maximum of 5 carbon atoms. The
. salts of the said acidalkylesterswhich contain a radical of sulfuric, boric, phosphoric or thiophosphoric acid, and especially of sulfuric or phosphoric acid, are of particular interest in connection with the present invention. These par- 1 tial esters (which are herein designated as acid alkyl esters) may be represented by the formula (Emir-Atom).
in which R represents an aliphatic hydrocarbon radical which contains less than 6 carbon atoms,
A represents the residue of the inorganic acid (as for example the radical $02, the radical PO,
theradical B, ,etc.),
n represents the number of hydrogen atoms, in
the uncombined polybasic acid from which the ester is derivable, which are replaceable by a metal (hereindesignated asrepl aceable hydrogen atoms), and :c is one or more but not greater than n-1.
the parent polybasic inorganic acid has not been replaced.
It is to be noted in the case of acid alkyl esters which are derivatives of polybasic acids containing 3 or more replaceable hydrogen atoms in. which more than one of said hydrogen atoms have been replaced by organic radicals, the said organic radicals (represented by R in the above formula) may be the same or different. i The alkyl ester salts employed in accordance with the present invention comprise the solublesalts of the herein-described acid alkyl esters; e. g., those resulting from the combination of the said acid alkyl esters with any suitable metal or base, including the organic bases, producing salts having good solubility and also preferably a finely crystalline or amorphous form in the solid For example, alkali metal, alkali earth state. metal, ammonium, etc. salts may be employed or the salts formed by the interaction of the-said acid alkyl esters with such organic bases as alkyl amines (particularly the hydroxy alkayl amines), pyridine, guanidine, urea or other salt-forming organic ammonium bases.
The said alkyl ester salts employed in accordance with the present'invention may be prepared in any manner well known to the art; as for example by the treatment of the corresponding alcohol, in the presence or absence of a solvent or diluent, with a suitable inorganic reagent (such' as phosphorus chloride or oxychloride, concentrated sulfuric acid and/or chlorsulfonic acid,
etc), and neutralization of the resulting acid alkyl ester withan inorganic or organic base i which forms a readily soluble salt with said acid acid or chlorsulfonic acid may contain varying amounts of sulfonic acids which are sometimes produced due to secondary reactions; the presencegef such sulfonic acids, however, does not impair the usefulness of the monoalkyl sulfuric acids in accordance with the present invention.
and. boric acids; diamyl dithiophosphoric acids;
etc.
Of special interest in connection with the present invention are the alkali metal salts of the sulfuric acid mono esters of the various alcohols which contain not more than 5 carbon atoms, in-
cludingthosewhich contain single or multiple bonds, straight chains and branched chains. Thus, there may be particularly mentioned, by way of illustration, the sodium or potassium salts ofthe following: ethyl sulfuric acid; normal and isopropyl sulfuric acids; the monosulfuric acid ester of methyl ethyl carbinol; normal, iso-, and tertiary-butyl sulfuric acids; the mono sulfuric acid esters of pentasol, of'secondary butyl carbinol, and of methyl-n-propyl carbinol; pentene-2- sulfuric acid; normal amyl sulfuric acid; tertiary amyl sulfuric acid; amylene sulfuric acid; etc. The salts of the monoalkyl sulfuric acids which contain from 3 to 5 carbon atoms in the alkyl group are of especial value in the production of vat dye composition in accordance with the present in vention. Those in which the alkyl group comprises an iso-alkyl radical (as for example, an isopropyl radical:
I CH:
CH- CH: an isobutyl radical:
CH- cmonz etc.) are somewhat superior in their action tothose in which the alkyl group is a normal or straightchain radical, although they are somewhat more hygroscopic than those in which the alkyl group is anormal or straight-chain radical.
The said sulfuric acid mono alkyl esters may be prepared in any manner well known to the of 'chlorsulfonic acidto form the sulfuric acid mono ester of the alcohol, the mixture then may be blown with air to remove hydrogen chloride formed, and subsequently stirred with water.
Mixtures of said salts of acid alkyl esters may also be employed in accordance with the present invention; as for example the salts of alkali metals or organic bases with the commercially available and cheap mixtures of alkyl sulfuric acids resulting from the sulfuric acid treatment of gaseous and lighter liquid unsaturated hydro carbons, such as mixtures produced in the recovery and removal of unsaturated hydrocarbons in the production and purification of gasoline in the so-called cracking process'of petroleum,
distillation.
Inasmuch as the quality and dispersibility of the resulting dye composition is dependent to a considerable extent upon the original degree of dispersion of the dyein the dispersion or suspension before drying, the vat dye is preferably 'ent, anti-foaming, assisting, wetting, catalytic,
enoly'zing, or other suitable action in the subse-v quent use of the compostions may also be incorporated into the compositions of thepresent intreated in the highly dispersed form. A suitable dispersing agent is preferably included in the dis-v persion or suspension so as to aid in preventing precipitation and-agglutination of the dye particles during the drying and to increase the fluidity and render easier the'incorporation of the monoalkyl sulfuric acid salt. Among the dispersing agents which may be employed for this purpose there may be mentioned for example, the sulfonic acids of benzene, hydroxybenzen'es, naphthalene,
hydroxynaphthalenes, their nuclear alkyl, nu.-. clear aralkyl and hydrogenated derivatives, as,
well as aldehyde condensation products thereof (as for example 2,6-naphthalenedisulfonic acid, 1.7-naphthalenedisulfonic acid, 2.8- naphthalenedisulfonic acid, isopropylnaplithalenesulfonic acids, dibutylnaphthalenesulfonic acids, amylna phthalcncsulfonic acids, butylbenzylnaphthalenesulfonic acids, cyclohexylnaphthalenesulfonic acids, methylene-di (betanapth'alenesu1- ionic acid), acetaledi (beta naphthalenesulfonic acid), benzal-di beta-naphthalenesulfonic acid),
methylene di (diisopropylnaphthalenesulfonic acid), etc.); sulfite cellulose waste liquors and,- their mildly oxidized. products and evaporated residues; sulfonated resins; abietene; abietine and abietane sulfonic'acids; and the like, as well as mixtures'of two or more of such substances.
Ifdesired, additional substances having dilu vention,,preferably while the latter are in the form of aqueous suspensions.
In order that the compositions may be in a A more satisfactory form for subsequent use, the
mixture of vvat dye inaqueous dispersion and salt.
scales or grains which may be used as such; or;
the paste, with or without preliminary. evaporation may be admixed with a, suitable hydrateforming soluble salt-in an anhydrous condition and the admixture stirred to produce a dryproduct. If desired, the dry products may be disintegrated into a powder in any suitable manner,
as for example by grinding in a ball mill, and;
subsequently screened.
' The amount-of salt of acid alkyl ester employed inthe'preparation of the compositions of the'present invention maybe varied over-a considerable range, depending in part upon the nature and concentration of the vat dye in the composition, the use to which the composition is to be put, and whether or notother diluents andother materials having a catalytic, assisting,
wetting, enolyzing, dispersing, or other action are included in the composition. For example,
an ideal vat dye composition in dry form is obtained by replacing all of the water in a vat dye paste with an equal amount of said alkyl estersalt, in which casethe' composition of the powder may be for example:
' Per cent Vat dyelactualjdye solids) 10-20 Dispersing agent (e. g. Leukanol) 1- 2 Salt of the acid alkyl ester; 89-78 While a powder composition having such a large content of the alkyl ester salt is an extremely advantageous product, in that it is applicable for the preparation of vat dyes of all classes in the powdered form which, when slurried with water, yield pastes which in many the preparation of a paste useful as a pigment (as for example for the coloring of paper and the like), only a sufficient amount of alkyl ester are quite suitable, such as sucrose (ordinary cane or beet sugar), .cerelose (or corn sugar), etc. Dextrines, glue, gelatin, gum arabic, or
other substances included in the general class of so-called protective colloids also may be used; as well as other products which do not cause precipitation of suspended vat dye particles or otherwise produce specky printing pastes (as for example, urea, variousother highly soluble amides, etc). i I
When the vat dye powder compositions of the present invention are to be employed in the preparation of vat dye printing pastes and it is desired to take advantage of the solubilizing action of the said alkyl ester salts, andespecially the monoalkyl sulfuric acid salts, in the preparation of the printing pastes and-their assisting action in the printing operation, a larger amount of said salts will ordinarily be employed than would be necessary merely for the preparation of a readily dispersible vat dye powder. As has been pointed out hereinbefore, the specific amount of of printing pastes with the aid of vat dye powders of the present invention, that the printing pastes frequently show signs of prereduction, even in the absence of printing catalysts or reduction accelerators employed in the art, such as aoaasae celerators," hydrotropic and/or enoiyzing substances, in addition to .or in replacement of part of other diluents.
It is to be noted that under the term hydrotropic substances are to be understood not only the substances specially enumerated by Neuberg and "Iamba chemische Zeitchrift, vol. 76, 1916, page 107 if., V 15 and Tamba, Biochemische Zeitchrift, vol. 145,
(compare Carl Neuberg, H
1924, page 415; Carl Neuberg, Sitzungsberichte der Koengl. Preussischen Akademie der Wissenschaf ten, 1916, page 1034), but all of those substances, which comply with the definition of the word hydrotropic as given by Neuberg. -As
, salt of ethyl sulphonic acid, potassium or soexamples of such substances the following may be mentioned: urea, substituted ureas, thiourea, hexamethylene tetramine, the potassium dium isovaleratathe alkali metal salts of the following acids: isobutyric acid, phenylacetic acid, benzoic acid, o-toluene-carboxylic acid,
salicylic acid, the benzene sulphonic acids, p-
toluene-sulphonic acid, the benzene sulphinic acids, 1.4-toluene sulphinic acid, naphthalene sulphonic acids, aniline sulphonic acids and substitution products thereof, naphthylamine sulfonic acids (as for example, l-amino-naphthae ,lene-3.6.8-trisulf0nic acid) picolinic acid, hydro aromatic carboxylic or suiphonic acids, and the a which It will be further noted that substances like. are not, strictly speaking, hydrotropic substances ,but which possess enolyzing propertiesarefincluded, as for example l-naphthalene sulphonic acid (sodium salt). I r
' present invention is of The presence of enolyzing substances in vat dye powders prepared ,in accordance withthe particular advantage in 5 connection with vat dyes of the indigoid and thioindigoid series, inasmuch as they tend to minimize or prevent isomerization of V the reduced vat dye to theketo form. v It may be noted, in connection with the use oflthe vat dye pastes andpowders of thepresent invention in dyeing and printing, that thevat dye pastes and powders of the present invention may be substituted in ordinary dye baths,
padding liquors and printinepastes in place of, the usual vat dye pastesfion the basis of the weight of the dye in the pasteor powder) without otherwise changing the proportions and ingredients of said compositions.
The vat dye compositions of the present in- H vention are particularly valuable for dyeing and (unbleached celfabrics and the like) inasmuch as the dyeings and prints ob tained" with the aid of such compositions have exprinting so-called gray goods" ceedingly :high tinctorial value and excellent penetration,
particularly when. compared with dyeings and prints made in the absence of the acid alkyl esters, and their salts, employed in accordance with the presentinvention.
The invention may be employed in connection with vat dyes of all types including those derived from anthraquinone, 'indophenois, various indigoid. thioindigoid and indirubin compounds, etc.; as ior example, indanthrones, pyranthrones, fia'vanthrones, dibenzanthrones, isodibenzanwt-lirones, perylene quinones, anthanthrones, di-
benzpyrene,
quinones, anth'rimido-carbazols,
naphthacridones, indigo, thioindigo, indirubin,
etc., including derivatives thereof, such as their halogen, nitro, sulfur and/or alkoxy derivatives.
The invention will be further described in coninection with the following specific examples (in which the parts are by weight), which are given to illustrate the invention. It will be realized,
however, that the invention is not limited thereto but thatchanges may be made in the materials treated and their proportions, manipulative steps,
1 and other conditions without departing from the scope of the appended patentclaims.
Example 1 .400. parts of indigo paste (containing 20 per cent. of pure indigo as shown by indigotine titration and resulting from the pre-.
a per cent'of indigo which, when added to water,
dispersesreadilyr When employed for the preparation of an indigo vat with the aid of the usual reducingagents (for example, alkaline sodium hydrosulfite), the powder reduces very rapidly andproduces a clear vat which dyes cotton even, blue shades of high tinctorial value. Instead of the normal butyi sodium sulfate, an equal amount of normal amyl sodium sulfate, (C5H1'1OSOsNa) or of any of the other salts of acid alkyl esters hereinbefore mentioned, and especially lower monoalkyl sulfuric acid soluble salts may be used.
Example 2.To 100 parts of the chlorinated indanthrcne vat dye known as National Carbanthrene Blue 308 (Color Index No. 1114) in the formof an aqueous suspension or commercial paste'vcontaining 18 per cent of total dye solids,
, there are'added with stirring 2 parts of Leukanol (or 6 parts of a 30 per cent solution of Leukanol) 50 parts of cane sugar, and25 parts of dextrine. The suspension is stirred until homogeneous, and then 5 parts of secondary butyl sodium sulfate are added and the mixture is stirred until solution of the alkyl sulfate is complete. The resulting mass, either as such or after evaporation, may be used as a paste; or it maybe evaporated to dryness, ground and screened, as in Example 1, to
produce a powder that is readily dispersed when added to water. The product, either in the form of paste or powder, gives uniform dyeings of high tinctorial value when employed to dye fabrics in accordance with standard practice, and especially by the pad andjig method. Instead of sec rial "is dissolved, and is then evaporated to'dryness, ground to a powder, and screened through a 60 mesh screen. The resulting product is a'violet colored powder Whichisfreadily dispersed upon; 1 adding to water and is especially suitable for dyeing. fibers by the pad andjjigfprocess. When the powderlis' made intoqa printing paste containing the usual additional ingredients, and the resulting I paste is. employed to print a textilefabric which 10,
is then dried, aged, developed and soaped in accordance with 'the standard procedure, abright violet, mum 'penetrated,f and,levelprint is'prov duced. Instead of the ln orm al-butyl sodium sulfate, the potassium salt of the acid sulfuric ester of dimethyl ethyl carbi'nolor readilysoluble salts, ,of any of the otheracid esters above disclosed may be" used;
Example '4.-' 10(i"'p artsof National Carbam threne Violet 2R Paste (cf. Example 3) are mixed with 25 parts of cane sugar and 68 parts of iso- ,propyl sodium sulfate v on," V I germane) C a,
and the mixture is stirrediiuntiljthe latter are dissolved. The resulting suspension is. thenfevapo rated to dryness, groundand'screenedy 100 parts of a violet powder is obtain whichpis' suitable for dyeing by all-known methods. It is especially;useful formaking'pastes tofbe used in dyeing by the-printing process.
Example 5. l parts" i the dye known as NationalVat Orange R (Color Index 1217) invtheform'of an aqueous paste containingaboutll" per cent of dye solids, are mixed withZ parts of Leukanol and 87 parts ofethyl' sodium, sulfate (C2Hs0SOaNa) until solution'of the latter is complete. The resulting suspension is evaporated to dryness, ground and screened. instead ofthe ethyl sodium sulfate other salts of thelower alkylsulfates may b'e employed. -100 parts of a Vat Orange R powder are thus obtained, which, when employed in the preparation of a printing paste (for-example by mixing150 partsof the powder-with 200parts of British .gui'n, 140 partsof potassium carbonate, 80 parts of sodium formaldehyde sulfoxylate, 50 parts of glycerin, and 380parts of water). and utilized in the printing .of. cotton in accordance withthe usual procedure, produces prints which in heavy shades'are about 20m 25 per cent greater in strength than corresponding prints made without the alkylsodium sulfate. I i-addition, the presence of the monoalkyl sulfuric acid salt results 'in'a' much greater brilliancy of.-shade andmore complete penetration of the, material, so that in many instances there are no back sides-and the fastness to crocking is-much enhanced.
-- alkyl esters whichcontain-an iso-radic'al (as for It may be; noted that the soluble salts of acid example, the isopropyl radical, the isobutyl radical, etc.) are preferably employed in connection with'yat dyes of the f thioindigoid series when the latter are to .be employed for the preparation of printing. pastes, in view of" their superior action inthe printing process. i
-E zcdmple 6.-'[-'I 'o 100 partsfl of .National Vat Orange RPaste (employed in Example 5), there are added 2 parts of Leukanol,;4 parts Tof the potassium salt of 2-carboxy benzophenone-le sulfonic a'cid 50 parts isobutyl-sodium sulfate,
and 33 parts of dextrine. The resulting mixture isstirred until all soluble matter'is dissolved, and the resultingsuspension is evaporated to dryness,
thioindigoid vat.
ground and screened. A bright orange pigment is obtained which disperses readily in vat printing pastes. When printed on textile fabrics of all kinds, it yieldsa very brilliant orange of increased strength over prints made fro'mtheioriginalVat'Oran'ge R Paste in the ordinary method. The potatssium Z-carboxy-bnzophenone- Gil 4"-sulfonate acts as an assistant or adjuvant,
as more fully disclosed and claimed in, my application Serial'No. 723.332, filed May 1,.1934.
, Example 7.-To 100 parts of the vat" dye known as National Vat Pink FF (6.6'-dichl0r'-4;.4-dimethyl thioindigo) in the form of an aqueous j paste or suspension containing 15 per cent of dye solids, there are added 2 parts of Leukanol, 64
parts of isobutyl sodium sulfate and i8 parts of cane sugar. The. mixture is stirred until the-soluble material is all dissolved, and is" then evaporated to dryness, ground and screened. 'A highly colored pink pigment is obtained which is readily dispersed in water or in sodium sulfate are added The mixture is stirred until all the soluble matter is completely dissolved, and is then evaporated to dryness,,ground and screened. 100 parts of a. blue powder are obtained which is of especial value for the preparation of printing pastes. The cane sugar employedin this example may be replaced by dextrine, gum'arabic, glue or other so-called protective colloids, alone'or with the addition of any of the substances above referred to as hydrotropic'or enolyzingsubstances.
Example 9.To 100 parts of National Carbanthrene Blue GCD Double. Paste (Color Index .1113) containing 16.5 per cent of dye solids and 1 per cent of Leukanol, there are added 50 parts of isobutyl sodium sulfate and 32.5 parts of urea, and the mixture isstirred until the latter are dissolved. The resulting suspension is evaporated to dryness, ground and screened. A very readily dispersible vat powder is obtained which is suitable for printing as well as dyeing.
' Example 10.-To 100 parts of'National Carbanthrene Fl-avine GC (cf. U. S. P. 993,992) in v the form of a commercial paste containing about 23 per cent of dye solids and about 2 per cent of Leukanol, there'are added 24 parts of sucrose,
55 parts of the sodium salt of the monosulfuric acid ester of secondary butyl carbinol CnHs v /CHCHIOSO8NB CH;
and 1 part of the disodium salt of 2.6-dihydroxyanthraquinone. .The mixture is stirred until all soluble matter is dissolved and the resulting suspension is evaporated to dryness, ground and screened. 100 parts ofa brilliant yellow powder is obtained which is suitable for dyeing and printing.
In the preparation of the compositions of the present invention, it is not necessary to employ a previously prepared dyestufi paste but the filter cakes and other separated forms of the dye may be employed; as for example, the press cakes resulting from the filtration of aqueous suspenas illustrated by the following example;
Example 11.-2 parts of the sodium salt of anthraquinone-Z-sulfonio acid are dissolved in 2031 parts of water, with the aid of heat if necessary, 100 parts of dextrine are added, and
the mixture is stirred until a smooth paste is obtained; 110 parts of National Vat Orange R (in the form of a press cake containing 21 per cent of dye solids) and 15 parts of Leukanol solution (30 per cent) are then added. The mixture is stirred until a well-dispersed thin fluid suspension is obtained. Then '74 parts of isobutyl sodium sulfate are added, and stirring is continued'until the latter is dissolved. The resulting mass is evaporated with'stirring until a thick paste "is obtained and is then dried, ground and screened as in the foregoing examples. 200
National Carbanthrene R d Violet RNX 1 i National Carbanthrene Brilliant parts of a brilliant orange powder is thus obtained having similar properties to those of the product of Example 6.
In the above examples other readily soluble salts of the hereindescribed acid alkyl esters, and especially other salts of alkyl sulfuric acids which are included within the i formula RCSOsH (in which R is a hydrocarbon radical containing a maximum of '5 carbon atoms), may be employed instead of all or a part of. the monalkyl sulfuric acid salts thereindisclosed. The vat dyes disclosed may be replaced by any other vat dye; as for example: a
National Carbanthrenelellow G--- Color IndexNo. National Carbanthrene G o l d e n 1 Orange G Color Index No. National ,Carbanthrene G old e n Orange 2R Color Indet No. National Carbanthrene Blue Green .FFB Color Index No. National Carbanthrene Violet 2R--- Color Index No. National Carbanthrene Dark Blue i olor Index No. 1099 Color Index No. 1161 Color Index No. 1101 Green supra National Vat Red Violet RH (Cf. U. S. P. 916,029) National Vat Scarlet G Color Index No. 1228 National Vat Brown G (di aphthyltliioindigoL; ational Vat Violet R Color Index No. 1222 National Brilliant Indigo B- Color Index No. 1190 National Brilliant Indigo 4B Color Index No. 1184 National Brilliant Indi 4G Color Index No. 1189 National Carbanthrene ed BN- Color Index No. 112 National Carbanthrene Brown A Color Index No. 110} National Carbanthrene Green B Color Ind ex bio. 11 2 National Carbanthrene Olive-Bani Color Incex 1N0. 1100 1 National Vat Yellow G ;Color Inoex No. 1196 National Carbanthrene Red AFF Color Inr ex No. 1133 National Carbanthrene Blue RS Color Index No. 1106 National VatPink BG Color Index No. 1210 National Vat Yellow R g Color Index No. 1170 National Carbanthrene Blue 3G-- Color Index No. 1109 Furthermore, mixtures of two or more vat dyes may be employedwhen it is desired to obtain compound shades, such as scarlets, browns, navy blues, and blacks.
- evaporated r'nixture.
fcor dance with the present invention by admixing a suitable hydrate forming soluble salt in an anhydrous condition with the paste, whereby a dry product is formed by formation of a hydrate of said salt. Thus, as will be further illustrated by the following specific examples, trisodium phosphate, sodium sulfate, sodium acetate or other suitable hydrate-forming soluble salts (having regard for the nature and intended use of the product) may beadmixed in an anhydrous condition (in the anhydrous form or a partially dehydrated'form) by stirring with a vat dye composition of the present invention in the form of a paste, preferably in the form of a partially The resulting dry mixture maybe ground and screened to form a powder. This latter procedure has the advantage of saving time and labor as compared with the evaporation procedure of drying. Furthermore, the danger of decomposition of the products by lengthy "denser (less bulky) and dusts less, and consequently is cheaped to ship on a volume basis and more convenient to use.
Example 12.-300 parts of indigo paste (containing 20 per cent of pure indigo, as shown by indigotin titration), are stirred with 2 parts of dry Leukanol until a thin fluid paste is obtained; parts of normal butyl sodium sulfate are then added, the mixture is stirred until solution of the alkyl sulfate is complete, and the resulting mixture is evaporated with stirring until a thick paste containing about 19 to 20 per cent of water is formed. 15 parts of anhydrous trisodium phosphate are then added and the mass is intimately mixed until a dry product is obtained. There is thus produced 100 parts of the dry composition containing 60 per cent of indigo. Upon grinding the product and screening through a screen of fine mesh, a fine dry powder is obtained. which disperses very readily and may be used for all dyeing purposes.
Example 13i-To 100 parts of the pyranthrone vat ,dyestuff known as National Carbanthrene Golden Orange 2 RT Paste (Color Index 1097), containinglO percent of dye solids in the form of an aqueous suspension and 1 per cent of Leukanol, there are added parts of cane sugar and 50 parts of isobutyl sodium sulfate. The mixture is evaporated with stirring until a paste containing 18 to 20 per cent of water is obtained. 15 parts of anhydrous trisodium phosphate are sodium sulfate, 1 part of the sodium salt of anthraquinone-Z-sulfonic acid, and 10 partspf cane sugar. The mixture is stirred to dissolve the sol- "uble material, and then evaporated with stirring until a paste containing approximately 16 per cent of'water is produced. "The resulting paste is intimately'mixed withl2 parts of anhydrous. trisodium phosphate whereby a dry product is obtained, which, when ground and screened, results in a bright orange powder having advantageous properties similar to, those of the prodnot of Example 6.
then added and themixture is stirred until a dry a mass is produced. Upon grinding and screen- 'wmie the invention has been described par ticularly with relation to the preparation of compositions which are especially suitable for the dyeing and printing of textile fabrics, it is to be understood that the invention is 'notlimited thereto but that the readily dispersible powders,
of the present invention are also of especial utility in the preparation of aqueous suspensions of the dyestufi forum in the pigment form for the dyeing of paper, the tinting of fibers and other material, and .the like;
It is further to be noted that the vat dye compositions of the present invention containing 'soluble salts of acid alkyl esters may also be utilizedas components of discharge and resist printing preparations as well as of the dyeing and printing compositions above described. v This application is a division of my application Serial No. 673,031, filed May 26, 1933, for Art of dyeing and coloring, and is in part a continuation of my application Serial No. 673,030, filed 1 .May 26, 1933, for Vat dye composition.
I claim:
l. A vat dye composition comprising a vat dye and a soluble salt of an alkylsulfuric acid corresponding with the formulaROSOfl-Lin which R represents a hydrocarbon radical containing less than 6 carbon atoms. 3
' 2. A vat dye composition comprising a vat dye and a soluble salt of an alkyl sulfuric acid corresponding with the formula ROSOsH, in which g R represents a hydrocarbon radical containing less than 6 carbon atoms, said composition being in the form of powder which dispersesreadily when added to water-. 7 I a 3. Avat dye composition in solid form for use in coloring, dyeing andtextile printing which comprises a vat dye, a dispersing agent, and a soluble salt of an alkyl sulfuric acidcorrespondthe NH4 radical.
5. A vat dye composition in the dry solid form comprising a vat dye'and an alkali metal salt of an alkyl sulfuric acid containing 3 to 5 carbon atoms in the alkyl group, said salt corresponding with the formula ROSOaM, in which R repre'' sents a saturated hydrpcarbonradical containing from 3 to 5 carbon atoms, and M represents an alkali metal. i
' 6. A vat dye composition in solid form adapted for use in textile printing which comprises a vat dye, an alkali metal salt of analkyl sulfuricacid containing less than 6 carbon atoms, said salt corresponding with the formula RQSOaM, in
which R represents an open-chain hydrocarbon radical containing less than 6 carbon atoms and M represents an alkali metal, and a material selected from the class of carbohydrates, printing catalysts, assistants, 'hydrotropic substances,-. and
enolyzing substances. k I 7. A 'vat dye composition in, solid form'for use in textile printingwhichv comprise's'avat dye and the sodium salt of an alkyl sulfuric acid containing less than 6 carbon atoms in the'alkyl group, said salt corresponding with the formula ROSOaNa, in which R represents an alkyl radical containing less than 6 carbon atoms, such as is obtainable by drying an aqueous mixture comprising the vat dye and the sodium salt of the alkyl sulfuric acid.
8. A vat dye composition in solid form adapted for use in textile printing which comprises a vat dye selected from the group of anthraquinone, indigoid and thioindigoid vat dyes, and the sodium salt of an alkyl sulfuric acid containing 3 to 5 carbon atoms in the alkyl group, said salt corresponding with the formula ROSOaNa, in which R represents a saturated hydrocarbon radical containing 3 to 5 carbon atoms.
9. A vat dye composition in dry solid form. which comprises an intimate mixture of a vat dye, an aldehyde condensation product of an aromatic sulfonic acid, a carbohydrate and a highly soluble salt of a monoalkyl sulfuric acid containing less than 6 carbon atoms.
10. A vat dye composition in dry solid form, which comprises an intimate mixture of a vat dye, a formaldehyde condensation product of a naphthalene sulfonic acid, a carbohydrate, and sodium isobutyl sulfate.
11. A method of making a vat dye composition which comprises incorporating a, soluble salt of an alkyl sulfuric acid corresponding with the formula ROSOsH, in which R represents a hydrocarbon radical containing less than 6 carbon atoms, into an aqueous suspension comprising a vat .dye and a dispersing agent, and drying the mass.
12. A method of making a vat dye composition which comprises incorporating a soluble salt of an alkyl sulfuric acid having the formula ROSOaM, .in which R represents an open-chain hydrocarbon radical containing less than 6 carbon atoms and M represents an alkali metal, into an aqueous suspension comprising a vatdye and an aldehyde condensation product of a naphthalene sulfonic acid as a dispersing agent, and drying the mass. 4
13. A method of making a vat dye composition,
which comprises incorporating an alkali metal salt of a monoalkyl sulfuric acid containing 2 to 5 carbon atoms into an aqueous mixture comprising a vat dye, a formaldehyde condensation product'of a naphthalene sulfonic acid, and a carbohydrate, and drying the mass.
14. A vat dye composition in the form of an aqueous paste comprising a vat dye, an aldehyde condensationv product of a naphthalene sulfonic acid as a dispersing agent, and a soluble salt of 1 an alkyl sulfuric acid containing less than 6 carbon atoms in the alkyl group, saidsalt corresponding with the formula ROSOaM, in which R represents an open-chain hydrocarbon radical containing less than 6 carbon atoms, and M represents an alkali metal.
15. A vat dye composition in the form of an aqueous paste comprising a vat dye, a formaldehyde condensation product of a naphthalene sulfonic acid and an-alkali metal salt of an alkyl sulfuric acid containing3 to 5 carbon atoms in the alkyl group, said salt corresponding with the formula ROSOsM, in which R represents a sat-. urated hydrocarbon radical, containing from 3 to 5 carbon atoms, and M represents an alkali metal.
16. A vat dye composition in the form of an aqueous paste comprising a vat dye, a dispersing agent, and a soluble salt'of an acid alkyl ester consisting on the one hand of a radical of an inorganic polybasic acid in which at least one of the replaceable hydrogen atoms is present and on the other hand 'of one or more lower alkyl hydrocarbon radicals directly linked to the inorganic radical; 17. A vatdye composition comprising a vat dye and a soluble salt of an acid alkyl ester consisting on the one hand of a radical of an inorganic polybasic acid in which at least one of the replaceable hydrogen atoms is present and on the other hand of one or more lower alkyl hydrocarbon radicals directly linked to the inorganic radical.
3 18. A vat dye composition in the dry solidform comprising a vat dye and an alkali metal salt of an acid alkyl ester consisting on the one hand of a radical of an inorganic polybasic acid in which at least one of the replaceable hydrogen atoms is present and-on the other hand of one or more lower alkyl hydrocarbon radicals directly 1g linked to the inorganic radical.
19. A vat dye composition in dry solid form.
which comprises an intimate mixture of a vat dye, an aldehyde condensation product of an arcmatic sulfonic acid and a highly soluble salt of an "acid alkyl ester consisting on the one hand of a radical of an inorganic polybasic acid in which at least one of the replaceable hydrogen atomsis present and on the other hand of one or more lower alkyl hydrocarbon radicals directly linked to the inorganic radical. g
20; Amethod of making a vat dye composition which comprises incorporating a soluble salt of an acid alkyl ester into an aqueous suspension comprising a vat dye and a dispersing agent, and drying the mass, said acid alkyl ester consisting on the one hand of a radical of an inorganic polybasic acid in which at least one of the replaceable hydrogen atoms is present and on the other hand of one or more lower 'alkyl hydrocarbon radicals :directly linked to the inorganic radical.
JEAN G. KERN.
Priority Applications (1)
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US62867A US2067926A (en) | 1933-05-26 | 1936-02-07 | Vat dye composition and manufacture thereof |
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US673031A US2145193A (en) | 1933-05-26 | 1933-05-26 | Vat dye composition |
US62867A US2067926A (en) | 1933-05-26 | 1936-02-07 | Vat dye composition and manufacture thereof |
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US62867A Expired - Lifetime US2067926A (en) | 1933-05-26 | 1936-02-07 | Vat dye composition and manufacture thereof |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2487197A (en) * | 1944-03-11 | 1949-11-08 | Du Pont | Process for dyeing textile fibers with vat dyes |
US2518153A (en) * | 1948-01-07 | 1950-08-08 | Du Pont | Dyeing of cellulose esters with reduced vat dyes in alcoholic solution |
US3156520A (en) * | 1963-04-01 | 1964-11-10 | American Can Co | Dyestuffs and alkali metal salts of wood sugar acids and lignin sulfonates |
-
1936
- 1936-02-07 US US62867A patent/US2067926A/en not_active Expired - Lifetime
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2487197A (en) * | 1944-03-11 | 1949-11-08 | Du Pont | Process for dyeing textile fibers with vat dyes |
US2518153A (en) * | 1948-01-07 | 1950-08-08 | Du Pont | Dyeing of cellulose esters with reduced vat dyes in alcoholic solution |
US3156520A (en) * | 1963-04-01 | 1964-11-10 | American Can Co | Dyestuffs and alkali metal salts of wood sugar acids and lignin sulfonates |
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