US2371101A - Polar quikontl sclphonamides as - Google Patents
Polar quikontl sclphonamides as Download PDFInfo
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- US2371101A US2371101A US2371101DA US2371101A US 2371101 A US2371101 A US 2371101A US 2371101D A US2371101D A US 2371101DA US 2371101 A US2371101 A US 2371101A
- Authority
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- United States
- Prior art keywords
- printing
- paste
- dye
- color
- beta
- Prior art date
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- Expired - Lifetime
Links
- 238000007639 printing Methods 0.000 description 100
- 239000000975 dye Substances 0.000 description 54
- -1 giycerine Chemical class 0.000 description 54
- 150000003254 radicals Chemical class 0.000 description 52
- 239000000843 powder Substances 0.000 description 38
- 239000002562 thickening agent Substances 0.000 description 32
- 239000000203 mixture Substances 0.000 description 28
- 238000000034 method Methods 0.000 description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 18
- 239000001257 hydrogen Substances 0.000 description 18
- 229910052739 hydrogen Inorganic materials 0.000 description 18
- 239000000984 vat dye Substances 0.000 description 16
- 230000032683 aging Effects 0.000 description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000004744 fabric Substances 0.000 description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 12
- 229920000742 Cotton Polymers 0.000 description 10
- 125000004103 aminoalkyl group Chemical group 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 8
- 239000007859 condensation product Substances 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- 239000000523 sample Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 229920000297 Rayon Polymers 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000002964 rayon Substances 0.000 description 6
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-Naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 4
- RZVHIXYEVGDQDX-UHFFFAOYSA-N Anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 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
- MTHSVFCYNBDYFN-UHFFFAOYSA-N Diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- FDDDEECHVMSUSB-UHFFFAOYSA-N Sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 125000004151 quinonyl group Chemical group 0.000 description 4
- 239000008149 soap solution Substances 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229960001663 sulfanilamide Drugs 0.000 description 4
- 150000003456 sulfonamides Chemical class 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- 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
- PIICEJLVQHRZGT-UHFFFAOYSA-N 1,2-ethanediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-Benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-Naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 2
- IAGVANYWTGRDOU-UHFFFAOYSA-N 1,4-dioxonaphthalene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C(S(=O)(=O)O)=CC(=O)C2=C1 IAGVANYWTGRDOU-UHFFFAOYSA-N 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- 206010000565 Acquired immunodeficiency syndrome Diseases 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N Diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- HJEINPVZRDJRBY-UHFFFAOYSA-N Disul Chemical compound OS(=O)(=O)OCCOC1=CC=C(Cl)C=C1Cl HJEINPVZRDJRBY-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- 235000019753 Finisher Diet Nutrition 0.000 description 2
- 229920002456 HOTAIR Polymers 0.000 description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N Melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 2
- GGCZERPQGJTIQP-UHFFFAOYSA-M Sodium 2-anthraquinonesulfonate Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)[O-])=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-M 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Tris Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 229960004418 Trolamine Drugs 0.000 description 2
- FKHNQSIOGWGQNY-UHFFFAOYSA-L [Na+].[Na+].[O-]S[O-] Chemical compound [Na+].[Na+].[O-]S[O-] FKHNQSIOGWGQNY-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- AFVAAKZXFPQYEJ-UHFFFAOYSA-N anthracene-9,10-dione;sodium Chemical compound [Na].C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 AFVAAKZXFPQYEJ-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 229910052803 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N diguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N ethanolamine Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 229920000591 gum Polymers 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000006011 modification reaction Methods 0.000 description 2
- HSXUHWZMNJHFRV-QIKYXUGXSA-L orange G Chemical compound [Na+].[Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1\N=N\C1=CC=CC=C1 HSXUHWZMNJHFRV-QIKYXUGXSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000001681 protective Effects 0.000 description 2
- 150000004059 quinone derivatives Chemical class 0.000 description 2
- 235000013533 rum Nutrition 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229940029612 triethanolamine Drugs 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/17—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/22—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using vat dyestuffs including indigo
Definitions
- This invention relates to a new type of dyeing and printing assistant, dyecomposltions containing these assistants and products printed therefrom.
- a dyepaste usually contains agents to prevent drying-out, settling and/or Dye powders, not being subject to,v these difficulties, do not require these agents.
- the dyepaste or dye powder must be admixed with suitable thickener, usually therefrom.
- the printing assistants usually operate more effectively when the printing-color pastels finally applied to the fabric.
- the'ae printing-,color pastes are usually p epared by the fabric finishers just before they are to be 7 e, printlngscolor pastes, however compounded, are then applied to textile. paper or other fabric materials .for decorative or protective purposes.
- the printed pieces are dried, agedin a steam ager, treatedwith' anoxidizing agent, rinsed and finally dried.”
- - printed fabric usually in'processing textiles,- printed fabric alsogis soaped at or near the "boil with about a 0.1% soap solution and a ain rinsed before the final dryinsr p ration,
- Dye pastes may contain printing-aids as one of their components and tins-color. made therefrom obviously contain the'printing assistant. Where a printing assistant is not present in the dye paste,
- the printing assistant he I 'i'heiradditicnatthe prop rpoint inthemanumuieactuaidycpute.
- triethanol amine and] or polyhydric alcohols such as giycerine, glycol,diethylene glycol and the like.
- a printing aid is to be incorporated in a dye powder
- a solid printing aid is necessary.
- solids which have been used in the past include the hydrochlorides of alkylol amines; silver salt (sodium anthraquinone betasulphonate); anthraquinone and certain metal salts such as those of cobalt and iron.
- the assistants should be useful both with dye and dye powders and in addition should be readily available orcheaply and easily prepared. It is, therefore, the object of the present invention to pro:
- the objects of the present invention are accomplished by using as a printing assistant a quinonyl-suiphonamide having a terminal polar latter with diethanolamine.
- Such compounds may be represented by the general formula 1 ethylene diamine and the other alkyl'ene an amines, guanidine carbonate, biguanide, melaz mine and the like.
- N-diethanol sulphonamides of beta-'anthraquinone sulphonic acid may be prepared by reacting the Other useful prodnets are obtained for example by the condensation of. a 'quinone-sulphonyl chloride and urea,
- dye and printing paste compositions of the present invention are not limited to the use of any particular dyes or dye forms; they are especially suitable for use with vat-dyes in either n alkanol, aminoethyl, c y a 00 15' paste or powder form.
- Particularly good results densed carbanryl radical and 'a: may be 1 or 2.
- Typical of the sulphonamides containing additional polar groups suitable for use according to the present invention are the monoand which may be represented by the formulae:
- the assistants may be added to the printing-color pastes at any point. They may be incorporated may be obtained using the-vat-dyev powders of high autodispersibility set forth in Crossley et 8.1., United States Reissue Patent 21,402, reissued March 19', 1940.
- Crossley et 8.1. United States Reissue Patent 21,402, reissued March 19', 1940.
- Example 1 I Apaste was prepared by slurrying 2,000 parts p sio s- T y fiv ,.therefore, a general appliso of British gum (Stein Hall) in 5,000 parts of water and the mixture was heated with contin-' uous' stirring until the temperature reached about 185 1. Heating was continued for about 1% hours after which 450 parts of powdered sodium ditions. Their use is simple since they may be carbonate and 450 parts of powde ed Potassium employed as powders, as suspensions in water or are impractical to form.v
- a quinone-suiphonic acid with orby reacting.
- a quinone-sulphonyl chloride with a suit able I'br example the N-ethanol betaanthraquinone sulfonamide may be prepared by reacting beta-anthraquinone sulphonyl chloride tinued until the temperaturedecreased to beta-naphthoquinone.
- thoquinone in 0856 Q 5 the succeeding examples this paste is referred to thoquinone, a: in the generic formula is ordinarily one since the disulphonamides of naphthoquinone as thickener A.
- a Example 2 120 parts of 3-2 British gum (Stein Hall) and sulphonamide. To this was added 97.25 parts of aldehyde were F. .at' which time 1,200 parts or potassium carhonate which had been previously dissolved in 1,000 parts oi water was added to the cooked gum 1,560 parts or sodium sulphoxylate tormdissolved in 1,500 parts of water at a temperature of about 140 F. and added to the common mixture with stirring until the whole was thoroughly mixed. 360 parts of giycerine were added and after thorough stirring the whole was bulked to about 12,000 parts. in the succeeding examples this is referred to, as thick-;
- Example4 The procedure of Example 3 was repeated ex-.
- Example 5 The procedure of Example 3 was repeated except that the, condensation product obtained from alpha-anthraquinone-sulphonic acid and monoethanolaniine was used in place of the betaanthraquinone derivative. Prints obtained fromv the pastes containing the printing assistant were definitely superior to those obtained i'rom the paste which had no printing assistant present.
- Example 7 A sample of. wet presscake ot Vat Orange R (C. Ir-1217) was dispersedwith a sodium salt of disul hophthylmethane. Alter adjusting the ure with water to contain 13% realcolor, lo parts of the mass was with 0.5 part of N-ethanol beta-anthraquinonesulphonr amide. To thiswas added 89.5 parts of thickener B. A second paste was pron red by mixing together 10 parts of the Vet Orange R and 90 parts of thickener B. This was the control sample. Both pastes were printed on samples oi rayon and cotton. The printed pieces were dried in a hot airoven, aged ina steam'ager, oxidised.
- Example 9 The procedure of Example 7 was repeated except that N-ethanol alpha-anthraquinone-sulphonamide was used. Again, improved printing was obtained when used.
- Emniple 10 the condensation product of beta-naphthoquinone sulphonic acid and ethanolamine as a. printing assistant. -As in Example 7, noticeably brighter and clearer prints were obtained when the condensation product was present in the printin Paste.
- Example 7 The procedure of Example 7 was repeated exactly' except that N-(beta-aminoethyi) beta-anthraquinonesulphonamide was used as the printing assistant. ,Prints obtained from the paste containing the printingassistant were definitely brighter and stronger than the prints obtained from the paste with water only. Example 1i.
- Example T was repeated exthe printing assistant was The procedure of Example I was followed using able when ageings were made under practical mill conditions..
- Example 13 procedure .0! Example? waslfoilowed except that the condensation product of betaanthraquinone-sulphonic acid and melamine was 'used as the printing assistant. , The prints dbtained from the Dastein which the printing assistant was used were stronger and brighter than the prints obtained ing thickener only.
- iz'rum lcu Iv actl except that printing thickener A was used 7 in place or printing thickener B. Prints'made from the paste'eontaining'the printing assistant and thickener A were definitely superior' to those prints made from the paste containin no print-- ing'" assistant.
- v Example-'16 from the paste contain- V The procedure oilixample'l was repeated ex- (c. 1.-.11-1a prepared swam States Reissue Patentlio. 21,402 and containing approximately 1 part of real dye were blended with 0.3 port of N-ethanol beta-anthraquinonesuiphonamide. Tothismixturewasaddedmpartsofthickener B, and the whole was thoroughlymixed. A second 5 parts of the Vat Yellow (30 powder were mixed with 90 parts of thickener B.
- a color composition comprising a vat dye and a quinone sulphonamide derivative having the general formula metric) in which represents apquinonyl radical selectedfrom the group consisting of the alphaand betaanthraquinonyl and beta-naphthaquinonyl radicals; R1 represents a radical selected from the group consisting oi hydrogen and the alkyl'ol, aminoalkyl, carbamyl and condensed carbamyl rfiicals, Rs'represents a radical-selected from the group consisting of the alhlol and amino selected from the group consisting of 1 and 2.
- a dye powder composition comprising a vat dye and a powdered quinone sulphonamide derivative having the general formula tiles in which Q represents a quinonyl radical-selected from the group consisting of the alphaand'beta v anthraquinonyl and beta-naphthaquinonyl radicals, R1 represents a radical selected from the group consisting of hydrogen 'and the alhlol chm I i ⁇ B- .r
- alkyl radicals and :r is a small whole number in which Qrepresents a quinonyl radical w from thegroup consisting of the alphaand betaanthraquinonyl and heta-naphthaquinonyl radicals, R1 represents a radical selected from the group consisting of hydrogen and the alhlol,
- R represents a radical selected from the group consisting of the alhlol and amino lalkyi radicals and: is a small whole number selected from the group consistingof i and 2.
- a color composition according-toclaim 1 in represents the beta-naphthoquinonyl i a thickener and a quinone derivative having the general formula in which Q represents a quinonyl radicalselected from the group of the alphaand betaanthraquinonyl and beta-naphthaquinonyl radicals, R1 represents a radical selected from the roup consisting of hydrogen and the alkylol, amino alkyl, carbamyl and condensed carbamyl radicals, Rs represents a radical'selected from the group of the alkyibl and amino alkyl radicals and a: is'a small whole number selected from the group consisting of 1 and 2.
- Ant dye composition comprising a dye, a thickener and a quinone sulphonamide derivative having the general formula in which 9 represents a quinonyl radical selected from the group consisting of the alphaand betaanthraquinonyl and beta-naphthaquinonyl radicals, R1 represents a radical selected from the group consisting of hydrogen and the alkylol, amino alkyl, carbamyl and condensed carbamyl radicals, R2 represents a radical selected from the.
- roup consisting of the alkylol and amino alkyl radicals and a: is a small whole number selected from the group consisting of 1 and 2.
- a printing paste composition comprising a highly-dispersed vat dye, a thickener and a quinone sulphonamide derivative having the general formula in which Q represents a quinonyl radical selected from the group consisting of the alphaand betaanthraquinonyl and beta-naphthaquinonyl radicals, R1 represents a radical selected from the group consisting of hydrogen and the alkylol,
- R2 represents a radical selected from the group consisting of the alkylol'and amino alkyl radicals and a: is a small whole,'number selected from the group consisting of 1 and 2, obtainable by compounding a colloidized vat dye powder of high autodispersibility and the quinone sulphonamide derivative with the thickener.
- a method of printing with cat colors which comprises printing a fabric with a printing paste composition comprising a vat dye, a thickener and 'a' quinone sulphonamide derivative having the general formula from thegroup consistingof the alphaand beta anthraquinonyl and beta-naphthaquinonyl radi cals, R1 represents a radical selected from the 51 A color composition according to claim 1 in which Q represents an anthraquinonyl group.
- a 6, 'A printing pastecompcsition comprising a 78' groupconsistingof hydrogen and the alkylol, amino alk'yl, carbamyl and condensed carbamyl radicals. It; represents a radical selected from the group consisting of the alkylol and amino 'alkyl radicals and a: is a small whole number selectedirom the group consisting of 1 and 2.
- Q represents a quinonyl radical selected in which Q represents a quinonyl radical selected from the roup consisting of the alphaand betaanthraquinonyl' and beta-naphthaquinonyl radi cals
- R1 represents a radical selected'from the roup consisting of hydrogen and the alkylol.
- Ra represents a radical selected from the group consisting of the alkylol and amino alkyi radicals and .1: is a small whole number selected from the group consisting of 1 and 2.
Description
ma ems omen STATE roma aUmom suu'nonamoss as i ram-mm AIDS ennui Kienle are Chester Albert Amick, Brook, N. 1., assignors to American anamid Company, New York, N. Y., a corpo tionoflilaine- No 1mm. Application Julyl, 1e43,
* Serial-No.4,131
10 Claim.
This invention'relates to a new type of dyeing and printing assistant, dyecomposltions containing these assistants and products printed therefrom.
Use of printing-color pastes containing dyes,
(Cl. 8-" factlire of the paste is not only 'tion they are thus generally more uniformly dispersed throughout a printing-color paste made particularly-in printing operations using vat dyes. is'sumciently well-knownso that the procedure v become almost standardized. The actual color 'source may be. either a dye paste or a dye powder;
Iniddltion to the real color, a dyepaste usually contains agents to prevent drying-out, settling and/or Dye powders, not being subject to,v these difficulties, do not require these agents.
but they contain 88ents or are so proces'sedas to promote dispcrsibility.
.In either case, the dyepaste or dye powder must be admixed with suitable thickener, usually therefrom. As a result, the printing assistants usually operate more effectively when the printing-color pastels finally applied to the fabric.
It is only relatively recently that dye powders suitable for use in making up printing-color pastes have been available. Most of the printing aids previously used in dye pastes, being either liquid in form or extremely hydroscopic, can not be used with dye powders, the latter being necessarily a sum dispersion, to forms printing-color paste a which is, suitable for application. In the case of vatdyes, it is also to add a reducing agent-and usually an alkali. Becausethecolor yield from printing-color pastes often decreases rapidly as the paste ages after being made up,
the'ae printing-,color pastes are usually p epared by the fabric finishers just before they are to be 7 e, printlngscolor pastes, however compounded, are then applied to textile. paper or other fabric materials .for decorative or protective purposes. The printed pieces are dried, agedin a steam ager, treatedwith' anoxidizing agent, rinsed and finally dried." Usually in'processing textiles,- printed fabric alsogis soaped at or near the "boil with about a 0.1% soap solution and a ain rinsed before the final dryinsr p ration,
In making up and applying printing-.color'pastes it has been found that a material suitable for use as a printing assistant is of advantage in obtainin: maximum color yield. .lhe exact way in which these act to produee'an improved color yield in printing is not entirely understood. It is with these printing aids or assistants that the present invention is particularly concerned.
Although printing aids are desimble in the 'printing-eolorpastes, the exact point at which they areadded may Dye pastes may contain printing-aids as one of their components and tins-color. made therefrom obviously contain the'printing assistant. Where a printing assistant is not present in the dye paste,
.itmaybeaddedatthetimeofmakingupthe It is preferable however, that the printing assistant he I 'i'heiradditicnatthe prop rpoint inthemanumuieactuaidycpute.
limited to the use of dry solids. Nevertheless, .it is desirable that printing assistants be incorpov rated in the powders-at the time of manufacture A for the same reasons which apply in the caseof dye pastes. e I V Dye pastes containing various liquid printing assistants have been made. Among theliquid materials used are the alkylolamines', for example,"
triethanol amine; and] or polyhydric alcohols such as giycerine, glycol,diethylene glycol and the like.
Various derivatives therefrom also have been tried. Iiil a printing aid is to be incorporated in a dye powder, a solid printing aid is necessary. Examples of such solids which have been used in the past include the hydrochlorides of alkylol amines; silver salt (sodium anthraquinone betasulphonate); anthraquinone and certain metal salts such as those of cobalt and iron.
Unfortunately, most of these printing aids previously used are not as satisfactory as may he desired. Many of them will not in all cases produce 7 the'intensiflcation of color for which they were intended. Others, such as the polyhydric alcohols, cause deterioration of .the printing-color pastes so that marked variations in the strength of prints therefrom are observable even after the printing-color paste has been allowed to stand for only a relatively short time. Many of them are satisfactory with somecolors but have an adverse eifect on others, even-to the extent of visibly altering the shade. None of them are suitable without. 1 modification for use both in paste and powder .compositions.
There remains, therefore, a demand for suitable printing "assistant which will produce. a satis-- factory eolor intensification and will not cause deterioration of the dyeing or printing composition on standing. Preferably the assistants should be useful both with dye and dye powders and in addition should be readily available orcheaply and easily prepared. It is, therefore, the object of the present invention to pro:
easier, but in addivide a new type of printing assistant which posisolated,
sesses these desirable Prop rties.
In general the objects of the present invention are accomplished by using as a printing assistant a quinonyl-suiphonamide having a terminal polar latter with diethanolamine.
group.. Such compounds may be represented by the general formula 1 ethylene diamine and the other alkyl'ene an amines, guanidine carbonate, biguanide, melaz mine and the like. a
'in which Q represents the residue of a quinone such as alpha or beta anthraquinone and betanaphthoquinone; R1 and R2 represent hydrogen with-ethanol amine. This compound gives an excellent printing assistant. Similarly, the N-diethanol sulphonamides of beta-'anthraquinone sulphonic acid may be prepared by reacting the Other useful prodnets are obtained for example by the condensation of. a 'quinone-sulphonyl chloride and urea,
While the dye and printing paste compositions of the present invention are not limited to the use of any particular dyes or dye forms; they are especially suitable for use with vat-dyes in either n alkanol, aminoethyl, c y a 00 15' paste or powder form. Particularly good results densed carbanryl radical and 'a: may be 1 or 2.- Typical of the sulphonamides containing additional polar groups suitable for use according to the present invention are the monoand which may be represented by the formulae:
So far as the present invention is concerned the assistants may be added to the printing-color pastes at any point. They may be incorporated may be obtained using the-vat-dyev powders of high autodispersibility set forth in Crossley et 8.1., United States Reissue Patent 21,402, reissued March 19', 1940. By combining the color matedi-N-ethanol,beta-anthraquinonylsulphonamides go rials or that atent into printingaste'compositions containing the printing assistants of the present "invention, the full. advantages of both may be gained with a resultant simplicity in use and excellence of shade and sharpness of color.
The invention will be more fully-set forth in connection with the following examples which are intended to be illustrative and not by way of limitation. All parts are by weight unless other- .wisenoted.
In the succeeding examp1es,-test prints were cotton print-cloth. Ageing of the prints was carried out in a steam ager which was constructed in such a manner that controlled temperatures could'be used. The temperature range normally used was 100-l05 C. Those ageings referred to the thickener; into the dye pastes or 40 as plant or hot ageings were carried out in the ders or may be blended directly into the printingcolor paste. However, as pointed out above, it is preferable that they be incorporated in the dye paste or powder during manufacture.
temperature range of about 106-110 C.- In the case of the cotton prints ageing periods of 3 minutes, 5 minutes or both were used. 0n rayon, ageing periods of 5 and 10 minutes or both were The use of this new class 0! printing assistants used. The shortest period which gives a satisfacpossesses a number of important advantages. These compounds are dry solids, which may be readily powdered and blended in dye powders but are also soluble or dispersible in dye paste suscation in both dye pastes and dye powders. They do not cause deterioration of printing-color pastes on standing. They encourage the production of excellent color yields even under hot ageing contory ag'eing is preferable.
Example 1 I Apaste was prepared by slurrying 2,000 parts p sio s- T y fiv ,.therefore, a general appliso of British gum (Stein Hall) in 5,000 parts of water and the mixture was heated with contin-' uous' stirring until the temperature reached about 185 1. Heating was continued for about 1% hours after which 450 parts of powdered sodium ditions. Their useis simple since they may be carbonate and 450 parts of powde ed Potassium employed as powders, as suspensions in water or are impractical to form.v
Compounds such as those used according to the present invention are readily prepared by-con- 7o dcnsing a quinone-suiphonic acid with orby reacting. a quinone-sulphonyl chloride with a suit able I'br example, the N-ethanol betaanthraquinone sulfonamide may be prepared by reacting beta-anthraquinone sulphonyl chloride tinued until the temperaturedecreased to beta-naphthoquinone.
carbonate were added and the mixture stirred until the carbonates dissolved] Heating was discontinued but stirring continued until the temperature reached approximately F. at which time 700 parts of sodium suiphoxylate formaldehyde were dissolved therein, 600 parts of glycerine. were-added and the paste bulked to about 10,000 parts with water. Stirring was continued until the paste cooled to room temperature. In
y' A in 0856 Q 5 the succeeding examples this paste is referred to thoquinone, a: in the generic formula is ordinarily one since the disulphonamides of naphthoquinone as thickener A. a Example 2 120 parts of 3-2 British gum (Stein Hall) and sulphonamide. To this was added 97.25 parts of aldehyde were F. .at' which time 1,200 parts or potassium carhonate which had been previously dissolved in 1,000 parts oi water was added to the cooked gum 1,560 parts or sodium sulphoxylate tormdissolved in 1,500 parts of water at a temperature of about 140 F. and added to the common mixture with stirring until the whole was thoroughly mixed. 360 parts of giycerine were added and after thorough stirring the whole was bulked to about 12,000 parts. in the succeeding examples this is referred to, as thick-;
ener B.
- Example 3 2.5 grams of dispersible Golden Orange (3- powder (C. I.- 1096), prepared according to United States Reissue Patent No. 21,402 and containing approximately 0.5 part of real color, were blended with 0. 25 part of N-ethanol beta-anthraquinonethickener'B, and the whole thoroughly mixed to produce a printing-color paste, A duplicate sam ple of the above was prepared except that no printing assistant was added and the amount of thickener B was 97.5 parts. Both pastes were printed on samples of cotton. The printed pieces were dried in a hot air oven, aged, oxidized,- soaped at the boil for five minutes with a 0.1%
soap solution, rinsed and finally iron dry. Definitely better prints were obtained from the pas containing the printing assistant.
Example4 The procedure of Example 3 was repeated ex-.
actly except that the Golden Orange G .was replaced by Dark Blue B0 powder (C. I.-1099). Prints obtained from the pastes containing the printing assistant were definitely stronger and 1 superior to the prints that were made from the paste which contained no assistant.
Example 5 The procedure of Example 3 was repeated except that the, condensation product obtained from alpha-anthraquinone-sulphonic acid and monoethanolaniine was used in place of the betaanthraquinone derivative. Prints obtained fromv the pastes containing the printing assistant were definitely superior to those obtained i'rom the paste which had no printing assistant present.
Egggmple 6 The procedure of"" fiample 5 was repeated except that the Dark Blue powder or Example 4 was Prints obtained from the paste in which the printing as t was present were definitely superior to the color value of the. prints obtained from the paste in which no printing assistant was used.
' Example 7 .A sample of. wet presscake ot Vat Orange R (C. Ir-1217) was dispersedwith a sodium salt of disul hophthylmethane. Alter adjusting the ure with water to contain 13% realcolor, lo parts of the mass was with 0.5 part of N-ethanol beta-anthraquinonesulphonr amide. To thiswas added 89.5 parts of thickener B. A second paste was pron red by mixing together 10 parts of the Vet Orange R and 90 parts of thickener B. This was the control sample. Both pastes were printed on samples oi rayon and cotton. The printed pieces were dried in a hot airoven, aged ina steam'ager, oxidised.
rinsed, soaped at the boil, (or live in a 70 printing assistaii Example 9 The procedure of Example 7 was repeated except that N-ethanol alpha-anthraquinone-sulphonamide was used. Again, improved printing was obtained when used.
Emniple 10 the condensation product of beta-naphthoquinone sulphonic acid and ethanolamine as a. printing assistant. -As in Example 7, noticeably brighter and clearer prints were obtained when the condensation product was present in the printin Paste.
' Ezample'1i The procedure of Example 7 was repeated exactly' except that N-(beta-aminoethyi) beta-anthraquinonesulphonamide was used as the printing assistant. ,Prints obtained from the paste containing the printingassistant were definitely brighter and stronger than the prints obtained from the paste with water only. Example 1i.
actly except that the reaction product of betaanthraquiiione-sulphonic acid and urea was used in place of the N-ethano1 beta-anthraquinonesulphcnamide. The color values of the prints which were obtained from the-paste in' which the t was present were definit ly superior than the color values of the prints ob.- tained rrom the pastein which no Printing as- Y sistant was used. This was particularly notice- The procedure of Example Twas repeated exthe printing assistant was The procedure of Example I was followed using able when ageings were made under practical mill conditions..
-' Example 13 procedure .0! Example? waslfoilowed except that the condensation product of betaanthraquinone-sulphonic acid and melamine was 'used as the printing assistant. ,The prints dbtained from the Dastein which the printing assistant was used were stronger and brighter than the prints obtained ing thickener only.
iz'rum lcu Iv actl except that printing thickener A was used 7 in place or printing thickener B. Prints'made from the paste'eontaining'the printing assistant and thickener A were definitely superior' to those prints made from the paste containin no print-- ing'" assistant. v Example-'16 from the paste contain- V The procedure oilixample'l was repeated ex- (c. 1.-.11-1a prepared swam States Reissue Patentlio. 21,402 and containing approximately 1 part of real dye were blended with 0.3 port of N-ethanol beta-anthraquinonesuiphonamide. Tothismixturewasaddedmpartsofthickener B, and the whole was thoroughlymixed. A second 5 parts of the Vat Yellow (30 powder were mixed with 90 parts of thickener B.
This was used as a control sample. Both pastes were printed on samples of rayon and cotton and finished in the usual manner. Prints obtained from the paste in which the printing assistant was present were definitely superior in color value to thoseobtained from the pastes in which no printing assistant was used.
We claim: o
1. A color composition comprising a vat dye and a quinone sulphonamide derivative having the general formula metric) in which represents apquinonyl radical selectedfrom the group consisting of the alphaand betaanthraquinonyl and beta-naphthaquinonyl radicals; R1 represents a radical selected from the group consisting oi hydrogen and the alkyl'ol, aminoalkyl, carbamyl and condensed carbamyl rfiicals, Rs'represents a radical-selected from the group consisting of the alhlol and amino selected from the group consisting of 1 and 2.
2. A dye powder composition comprising a vat dye and a powdered quinone sulphonamide derivative having the general formula tiles in which Q represents a quinonyl radical-selected from the group consisting of the alphaand'beta v anthraquinonyl and beta-naphthaquinonyl radicals, R1 represents a radical selected from the group consisting of hydrogen 'and the alhlol chm I i \B- .r
alkyl radicals and :r is a small whole number in which Qrepresents a quinonyl radical w from thegroup consisting of the alphaand betaanthraquinonyl and heta-naphthaquinonyl radicals, R1 represents a radical selected from the group consisting of hydrogen and the alhlol,
amino alhl, carhamyl and condensed carbamyl radicals, R: represents a radical selected from the group consisting of the alhlol and amino lalkyi radicals and: is a small whole number selected from the group consistingof i and 2.
4. A color composition according-toclaim 1 in represents the beta-naphthoquinonyl i a thickener and a quinone derivative having the general formula in which Q represents a quinonyl radicalselected from the group of the alphaand betaanthraquinonyl and beta-naphthaquinonyl radicals, R1 represents a radical selected from the roup consisting of hydrogen and the alkylol, amino alkyl, carbamyl and condensed carbamyl radicals, Rs represents a radical'selected from the group of the alkyibl and amino alkyl radicals and a: is'a small whole number selected from the group consisting of 1 and 2.
"1. Ant dye composition comprising a dye, a thickener and a quinone sulphonamide derivative having the general formula in which 9 represents a quinonyl radical selected from the group consisting of the alphaand betaanthraquinonyl and beta-naphthaquinonyl radicals, R1 represents a radical selected from the group consisting of hydrogen and the alkylol, amino alkyl, carbamyl and condensed carbamyl radicals, R2 represents a radical selected from the.
roup consisting of the alkylol and amino alkyl radicals and a: is a small whole number selected from the group consisting of 1 and 2.
8. A printing paste composition comprisinga highly-dispersed vat dye, a thickener and a quinone sulphonamide derivative having the general formula in which Q represents a quinonyl radical selected from the group consisting of the alphaand betaanthraquinonyl and beta-naphthaquinonyl radicals, R1 represents a radical selected from the group consisting of hydrogen and the alkylol,
amino alkyl, carbamyl and condensed carbamyl radicals,- R2 represents a radical selected from the group consisting of the alkylol'and amino alkyl radicals and a: is a small whole,'number selected from the group consisting of 1 and 2, obtainable by compounding a colloidized vat dye powder of high autodispersibility and the quinone sulphonamide derivative with the thickener.
9. A method of printing with cat colors which comprises printing a fabric with a printing paste composition comprising a vat dye, a thickener and 'a' quinone sulphonamide derivative having the general formula from thegroup consistingof the alphaand beta anthraquinonyl and beta-naphthaquinonyl radi cals, R1 represents a radical selected from the 51 A color composition according to claim 1 in which Q represents an anthraquinonyl group.
a 6, 'A printing pastecompcsition comprising a 78' groupconsistingof hydrogen and the alkylol, amino alk'yl, carbamyl and condensed carbamyl radicals. It; represents a radical selected from the group consisting of the alkylol and amino 'alkyl radicals and a: is a small whole number selectedirom the group consisting of 1 and 2.
man article or manufacture-comprising a in"which Q represents a quinonyl radical selected in which Q represents a quinonyl radical selected from the roup consisting of the alphaand betaanthraquinonyl' and beta-naphthaquinonyl radi cals, R1 represents a radical selected'from the roup consisting of hydrogen and the alkylol. amino alkyl, carbamyl and condensed carbamyl radicals, Ra represents a radical selected from the group consisting of the alkylol and amino alkyi radicals and .1: is a small whole number selected from the group consisting of 1 and 2.
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2938914A (en) * | 1957-09-25 | 1960-05-31 | American Cyanamid Co | Alkyl trialkylammonium salts as disperse dyes for acrylic fibers |
US3627791A (en) * | 1968-11-21 | 1971-12-14 | Richardson Merrell Inc | Bis(aminoalkylsulfamoyl) anthraquinones |
US3983248A (en) * | 1968-11-21 | 1976-09-28 | Richardson-Merrell Inc. | Bis(aminoalkylsulfamoyl)anthraquinone antiviral agents |
US20040072653A1 (en) * | 2002-10-09 | 2004-04-15 | Depco, Inc. | Therapeutic color changing putty and method of therapeutic exercise using same |
WO2009016083A1 (en) * | 2007-08-02 | 2009-02-05 | Basf Se | Degradation accelerator for polymers and polymer article comprising it |
-
0
- US US2371101D patent/US2371101A/en not_active Expired - Lifetime
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2938914A (en) * | 1957-09-25 | 1960-05-31 | American Cyanamid Co | Alkyl trialkylammonium salts as disperse dyes for acrylic fibers |
US3627791A (en) * | 1968-11-21 | 1971-12-14 | Richardson Merrell Inc | Bis(aminoalkylsulfamoyl) anthraquinones |
US3983248A (en) * | 1968-11-21 | 1976-09-28 | Richardson-Merrell Inc. | Bis(aminoalkylsulfamoyl)anthraquinone antiviral agents |
US20040072653A1 (en) * | 2002-10-09 | 2004-04-15 | Depco, Inc. | Therapeutic color changing putty and method of therapeutic exercise using same |
WO2009016083A1 (en) * | 2007-08-02 | 2009-02-05 | Basf Se | Degradation accelerator for polymers and polymer article comprising it |
US20100222454A1 (en) * | 2007-08-02 | 2010-09-02 | Ciba Corporation | Degradation accelerator for polymers and polymer article comprising it |
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