BE612605A

BE612605A -

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Publication number: BE612605A
Authority: BE; Belgium
Prior art keywords: acid; dyes; amino; acid chloride; water
Prior art date

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English (en)

French (fr)

Publication of BE612605A publication Critical patent/BE612605A/fr

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239000000975 dye Substances 0.000 claims description 34
239000002253 acid Substances 0.000 claims description 23
239000011780 sodium chloride Substances 0.000 claims description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
238000000034 method Methods 0.000 claims description 13
-1 ( 3-amino-phenyl) -4-amino-anthraquinone sulfonic acid Chemical compound 0.000 claims description 12
239000000985 reactive dye Substances 0.000 claims description 11
150000001875 compounds Chemical class 0.000 claims description 10
150000003839 salts Chemical group 0.000 claims description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 8
239000004753 textile Substances 0.000 claims description 8
238000005917 acylation reaction Methods 0.000 claims description 7
150000004056 anthraquinones Chemical class 0.000 claims description 6
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 6
239000003086 colorant Substances 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000000542 sulfonic acid group Chemical group 0.000 claims description 5
HFBMWMNUJJDEQZ-UHFFFAOYSA-N Acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 claims description 4
CXJAFLQWMOMYOW-UHFFFAOYSA-N 3-chlorofuran-2,5-dione Chemical compound ClC1=CC(=O)OC1=O CXJAFLQWMOMYOW-UHFFFAOYSA-N 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 claims description 3
INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 claims description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
229920002678 cellulose Polymers 0.000 claims description 2
239000001913 cellulose Substances 0.000 claims description 2
CERQOIWHTDAKMF-UHFFFAOYSA-N methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
VWQXLMJSFGLQIT-UHFFFAOYSA-N prop-2-enoyl bromide Chemical compound BrC(=O)C=C VWQXLMJSFGLQIT-UHFFFAOYSA-N 0.000 claims description 2
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 claims description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical group OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
PVRIJONPGONPNG-UHFFFAOYSA-M ClC(C(=O)Cl)=C.[Cl-] Chemical compound ClC(C(=O)Cl)=C.[Cl-] PVRIJONPGONPNG-UHFFFAOYSA-M 0.000 claims 1
229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 29
239000003795 chemical substances by application Substances 0.000 description 15
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 8
239000000203 mixture Substances 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
AKEJUJNQAAGONA-UHFFFAOYSA-N Sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 6
WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
229920000742 Cotton Polymers 0.000 description 5
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
238000004043 dyeing Methods 0.000 description 5
238000003756 stirring Methods 0.000 description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
239000000243 solution Substances 0.000 description 4
238000006277 sulfonation reaction Methods 0.000 description 4
229910006069 SO3H Inorganic materials 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
239000004744 fabric Substances 0.000 description 3
SECXISVLQFMRJM-UHFFFAOYSA-N n-methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
239000001103 potassium chloride Substances 0.000 description 3
235000011164 potassium chloride Nutrition 0.000 description 3
239000000047 product Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
WNLRTRBMVRJNCN-UHFFFAOYSA-N Adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
238000007792 addition Methods 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
230000000875 corresponding Effects 0.000 description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
WTEVQBCEXWBHNA-YFHOEESVSA-N neral Chemical compound CC(C)=CCC\C(C)=C/C=O WTEVQBCEXWBHNA-YFHOEESVSA-N 0.000 description 2
230000001264 neutralization Effects 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000004627 regenerated cellulose Substances 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
XBGXIWFUHLXTTR-UHFFFAOYSA-N 1-amino-4-bromo-9,10-dioxo-2H-anthracene-1-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)(S(O)(=O)=O)CC=C2Br XBGXIWFUHLXTTR-UHFFFAOYSA-N 0.000 description 1
XOTUAMWIFRDGMZ-UHFFFAOYSA-N 2-chloroprop-2-enoyl chloride Chemical compound ClC(=C)C(Cl)=O XOTUAMWIFRDGMZ-UHFFFAOYSA-N 0.000 description 1
229920002456 HOTAIR Polymers 0.000 description 1
NAQMVNRVTILPCV-UHFFFAOYSA-N Hexamethylenediamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
HNPPKZRZKDKXDO-UHFFFAOYSA-N N,N-dimethylformamide;propan-2-one Chemical compound CC(C)=O.CN(C)C=O HNPPKZRZKDKXDO-UHFFFAOYSA-N 0.000 description 1
DIQREOXZEGJZFH-UHFFFAOYSA-N NC1=C(C(=C(C=2C(C3=CC=CC=C3C(C12)=O)=O)S(=O)(=O)O)S(=O)(=O)O)S(=O)(=O)O Chemical compound NC1=C(C(=C(C=2C(C3=CC=CC=C3C(C12)=O)=O)S(=O)(=O)O)S(=O)(=O)O)S(=O)(=O)O DIQREOXZEGJZFH-UHFFFAOYSA-N 0.000 description 1
YSAVLUVRTMYHEW-UHFFFAOYSA-N NC1=C(C=C(C=2C(C3=CC=CC=C3C(C1=2)=O)=O)N)C1=CC=CC=C1 Chemical compound NC1=C(C=C(C=2C(C3=CC=CC=C3C(C1=2)=O)=O)N)C1=CC=CC=C1 YSAVLUVRTMYHEW-UHFFFAOYSA-N 0.000 description 1
XWBXRNDCXIULOL-UHFFFAOYSA-N NC=1C=C(C=CC1)C1=CC=C(C=2C(C3=CC=CC=C3C(C12)=O)=O)N Chemical compound NC=1C=C(C=CC1)C1=CC=C(C=2C(C3=CC=CC=C3C(C12)=O)=O)N XWBXRNDCXIULOL-UHFFFAOYSA-N 0.000 description 1
229920002292 Nylon 6 Polymers 0.000 description 1
GEYOCULIXLDCMW-UHFFFAOYSA-N O-Phenylenediamine Chemical class NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
210000002268 Wool Anatomy 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
WTEVQBCEXWBHNA-JXMROGBWSA-N citral A Natural products CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000004386 diacrylate group Chemical group 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000001747 exhibiting Effects 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000002657 fibrous material Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000010985 leather Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
NPYPAHLBTDXSSS-UHFFFAOYSA-N potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
FKNQFGJONOIPTF-UHFFFAOYSA-N sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
230000003381 solubilizing Effects 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
239000000725 suspension Substances 0.000 description 1
UPKAWFACSJWKND-ZXFFUEEESA-J tetrasodium;(6E)-4-amino-6-[[4-[4-[(2Z)-2-(8-amino-1-oxo-5,7-disulfonatonaphthalen-2-ylidene)hydrazinyl]-3-methoxyphenyl]-2-methoxyphenyl]hydrazinylidene]-5-oxonaphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C\1=CC2=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C(N)=C2C(=O)C/1=N/NC(C(OC)=C1)=CC=C1C1=CC=C(N\N=C\2C(C3=C(N)C(=CC(=C3C=C/2)S([O-])(=O)=O)S([O-])(=O)=O)=O)C(OC)=C1 UPKAWFACSJWKND-ZXFFUEEESA-J 0.000 description 1
SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
238000009834 vaporization Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000003021 water soluble solvent Substances 0.000 description 1
239000002759 woven fabric Substances 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1