WO1995014519A1 - Verfahren zur herstellung wasserfreier, rieselfähiger zuckertensidpulver - Google Patents
Verfahren zur herstellung wasserfreier, rieselfähiger zuckertensidpulver Download PDFInfo
- Publication number
- WO1995014519A1 WO1995014519A1 PCT/EP1994/003855 EP9403855W WO9514519A1 WO 1995014519 A1 WO1995014519 A1 WO 1995014519A1 EP 9403855 W EP9403855 W EP 9403855W WO 9514519 A1 WO9514519 A1 WO 9514519A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- carbon atoms
- radical
- sugar
- formula
- Prior art date
Links
- 235000000346 sugar Nutrition 0.000 title claims abstract description 44
- 239000000843 powder Substances 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 43
- 238000002360 preparation method Methods 0.000 claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 11
- 239000000344 soap Substances 0.000 claims abstract description 5
- 239000004094 surface-active agent Substances 0.000 claims description 42
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 28
- 239000000194 fatty acid Substances 0.000 claims description 28
- 229930195729 fatty acid Natural products 0.000 claims description 28
- -1 alkenyl sulfates Chemical class 0.000 claims description 26
- 150000004665 fatty acids Chemical class 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 238000001035 drying Methods 0.000 claims description 19
- 239000003945 anionic surfactant Substances 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000000969 carrier Substances 0.000 claims description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000003513 alkali Substances 0.000 claims description 9
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 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 claims description 4
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- 229910052910 alkali metal silicate Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052915 alkaline earth metal silicate Inorganic materials 0.000 claims 1
- 239000000356 contaminant Substances 0.000 claims 1
- 229930182470 glycoside Natural products 0.000 claims 1
- 150000002338 glycosides Chemical class 0.000 claims 1
- 239000000606 toothpaste Substances 0.000 abstract description 9
- 239000013543 active substance Substances 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 25
- 239000000203 mixture Substances 0.000 description 14
- 235000002639 sodium chloride Nutrition 0.000 description 13
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 13
- 238000000227 grinding Methods 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- 150000002191 fatty alcohols Chemical class 0.000 description 7
- 235000019353 potassium silicate Nutrition 0.000 description 7
- 244000060011 Cocos nucifera Species 0.000 description 6
- 235000013162 Cocos nucifera Nutrition 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 239000002736 nonionic surfactant Substances 0.000 description 6
- 229920000151 polyglycol Polymers 0.000 description 6
- 239000010695 polyglycol Substances 0.000 description 6
- 150000004760 silicates Chemical class 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- 206010013911 Dysgeusia Diseases 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229940096386 coconut alcohol Drugs 0.000 description 4
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 229930182478 glucoside Natural products 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 4
- 239000003760 tallow Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 4
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 3
- 229940055577 oleyl alcohol Drugs 0.000 description 3
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 3
- 238000006384 oligomerization reaction Methods 0.000 description 3
- 150000003138 primary alcohols Chemical class 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 230000019635 sulfation Effects 0.000 description 3
- 238000005670 sulfation reaction Methods 0.000 description 3
- CFOQKXQWGLAKSK-KTKRTIGZSA-N (13Z)-docosen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCCO CFOQKXQWGLAKSK-KTKRTIGZSA-N 0.000 description 2
- FTLYMKDSHNWQKD-UHFFFAOYSA-N (2,4,5-trichlorophenyl)boronic acid Chemical class OB(O)C1=CC(Cl)=C(Cl)C=C1Cl FTLYMKDSHNWQKD-UHFFFAOYSA-N 0.000 description 2
- DJYWKXYRGAMLRE-QXMHVHEDSA-N (z)-icos-9-en-1-ol Chemical compound CCCCCCCCCC\C=C/CCCCCCCCO DJYWKXYRGAMLRE-QXMHVHEDSA-N 0.000 description 2
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 2
- CFOQKXQWGLAKSK-UHFFFAOYSA-N 13-docosen-1-ol Natural products CCCCCCCCC=CCCCCCCCCCCCCO CFOQKXQWGLAKSK-UHFFFAOYSA-N 0.000 description 2
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- ZFMSMUAANRJZFM-UHFFFAOYSA-N Estragole Chemical compound COC1=CC=C(CC=C)C=C1 ZFMSMUAANRJZFM-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- 239000005639 Lauric acid Substances 0.000 description 2
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000004280 Sodium formate Substances 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 239000000551 dentifrice Substances 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- 229960000735 docosanol Drugs 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- UWKAYLJWKGQEPM-LBPRGKRZSA-N linalyl acetate Chemical compound CC(C)=CCC[C@](C)(C=C)OC(C)=O UWKAYLJWKGQEPM-LBPRGKRZSA-N 0.000 description 2
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 2
- 239000000391 magnesium silicate Substances 0.000 description 2
- 229910052919 magnesium silicate Inorganic materials 0.000 description 2
- 235000019792 magnesium silicate Nutrition 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229940043348 myristyl alcohol Drugs 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
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- 239000002245 particle Substances 0.000 description 2
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- 235000021317 phosphate Nutrition 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
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- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 2
- 235000019254 sodium formate Nutrition 0.000 description 2
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- 229910000162 sodium phosphate Inorganic materials 0.000 description 2
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 2
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- RRBZUCWNYQUCTR-UHFFFAOYSA-N 2-(aminoazaniumyl)acetate Chemical class NNCC(O)=O RRBZUCWNYQUCTR-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D1/00—Evaporating
- B01D1/16—Evaporating by spraying
- B01D1/18—Evaporating by spraying to obtain dry solids
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D11/00—Special methods for preparing compositions containing mixtures of detergents
- C11D11/0082—Special methods for preparing compositions containing mixtures of detergents one or more of the detergent ingredients being in a liquefied state, e.g. slurry, paste or melt, and the process resulting in solid detergent particles such as granules, powders or beads
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/42—Amides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
- A61K8/604—Alkylpolyglycosides; Derivatives thereof, e.g. esters
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/20—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/017—Mixtures of compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
- C11D1/525—Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain two or more hydroxy groups per alkyl group, e.g. R3 being a reducing sugar rest
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/662—Carbohydrates or derivatives
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/835—Mixtures of non-ionic with cationic compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/86—Mixtures of anionic, cationic, and non-ionic compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
- C11D1/146—Sulfuric acid esters
Definitions
- the invention relates to a process for the preparation of water-free, free-flowing sugar surfactant powder, in which alkyl and / or alkenyl oligoglycosides and / or fatty acid N-alkyl polyhydroxyalkylamides are treated at 100 to 225 ° C. with superheated steam and the use of the substances for the production of surface-active agents.
- Alkyl and / or alkenyl oligoglycosides and preferably alkyl oligoglucosides are nonionic surfactants based on renewable raw materials, which are becoming increasingly important for the production of surface-active agents owing to their excellent application properties and their particular eco-toxicological compatibility.
- a market segment for which the two sugar surfactants appear to be particularly suitable is the area of oral and dental care products.
- the international patent application WO 91/02046 proposes pulverulent preparations which contain silicas and alkyl oligoglucosides and are suitable for the production of toothpastes.
- the international patent application WO 91/02513 discloses anti-fouling toothpastes which contain an antimicrobial biguanide, aluminum oxide trihydrate as a polishing agent and as a surfactant component, for example alkyl oligoglucoside.
- Oral and dentifrices which contain mixtures of alkyl ether sulfates and alkyl oligoglucosides are also known from German patent application DE-A1 4101505 (Henkel).
- Japanese patent application JP 1 / 068.312 proposes toothpastes with good foaming properties, which contain calcium hydrogen phosphate, glycerol, carboxymethyl cellulose and decyl glucoside.
- alkyl oligoglucosides Due to the production process, alkyl oligoglucosides contain about 1 to 2% by weight of free fatty alcohol, which usually cannot be removed by distillation. However, this low content leads to an unacceptable taste impairment in toothpastes. 2. Both alkyl oligoglucosides and fatty acid N-alkyl glucamides from the peroxide bleach can contain about 0.5% by weight of formic acid or formate. Although this content is completely harmless from a physiological point of view, it also has a significant influence on the taste of the products.
- the sugar surfactants must be used in anhydrous or at least heavily dewatered form, preferably as a powder.
- alkyl oligoglucosides nor fatty acid N-alkylglucate-ide can be obtained water-free by conventional industrial processes, since the sensitive sugar residues become one under the conditions of spray drying or in a thin-film evaporator in which the heat is transferred via the hot metal wall significant portion carbonize.
- sugar surfactant powder which is dried by conventional methods, Especially if they contain anionic surfactants, for example of the alkyl sulfate type, as additional constituents, are not sufficiently soluble in cold water and have an insufficiently low bulk density.
- the complex object of the invention was therefore to provide a process for the production of sugar surfactants in solid, anhydrous form which is free from the disadvantages described.
- the invention relates to a process for the preparation of anhydrous, free-flowing sugar surfactant powder, in which aqueous preparations containing
- anhydrous sugar tert-powders obtainable by the process according to the invention - containing sugar surfactants and optionally anionic surfactants - not only have a surprisingly good flowability and color quality, but are also particularly easily water-soluble. Proportions of free fatty alcohols, formic acid or their salts, which the taste and can adversely affect the olfactory properties of the product, are either practically completely removed together with the water or at least their concentration is reduced to such an extent that they are no longer perceived as annoying for application reasons. This is the first time that a drying process for sugar tertiary sides as well as for mixtures of sugar surfactants and anionic surfactants is available, in which the heat transfer does not take place through contact with a hot metal wall.
- the invention includes the knowledge that the use of special silicate carriers is particularly advantageous when it comes to lowering the drying temperature to such an extent that neither char products nor caking occur and yet a non-sticky, dry, free-flowing powder is obtained.
- the sugar surfactant powders obtainable by the process according to the invention are furthermore distinguished by significantly improved odor and taste properties.
- alkyl and / or alkyl oligoglycosides follow the formula (I)
- R 1 is an alkyl and / or alkenyl radical having 6 to 22 carbon atoms
- G is a sugar radical having 5 or 6 Carbon atoms
- p represents a number in the range from 1 to 10.
- the alkyl and / or alkenyl oligoglycosides can be derived from aldoses or ketoses with 5 or 6 carbon atoms, preferably glucose.
- the preferred alkyl and / or alkenyl oligoglycosides are thus alkyl and / or alkenyl oligoglucosides.
- the alkyl or alkenyl radical R 1 can be derived from primary alcohols having 6 to 11, preferably 8 to 10, carbon atoms. Typical examples are butanol, capro alcohol, caprylic alcohol, capric alcohol and undecyl alcohol and their Technical mixtures, such as those obtained in the hydrogenation of technical fatty acid methyl esters or in the course of the hydrogenation of aldehydes from Roelen's oxo synthesis.
- the alkyl or alkenyl radical R 1 can also be derived from primary alcohols having 12 to 22, preferably 12 to 14, carbon atoms. Typical examples are lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, and their technical mixtures, which can be obtained as described above. Alkyl oligoglucosides based on hardened C ⁇ _2 / 14 coconut alcohol with a DP of 1 to 3 are preferred.
- R- ⁇ CO for an aliphatic acyl radical with 6 to 22 carbon atoms
- R3 for hydrogen, an alkyl or hydroxyalkyl radical with 1 to 4 carbon atoms
- [Z] for a linear or branched polyhydroxyalkyl radical with 3 to 12 carbon atoms and 3 to 10 hydroxyl groups stands.
- the fatty acid N-alkyl polyhydroxyalkylamides are known substances which can usually be obtained by reductive amination of a reducing sugar with ammonia, an alkylamine or an alkanolamine and subsequent acylation with a fatty acid, a fatty acid alkyl ester or a fatty acid chloride.
- a reducing sugar with ammonia
- an alkylamine or an alkanolamine and subsequent acylation with a fatty acid, a fatty acid alkyl ester or a fatty acid chloride.
- US Pat. Nos. US 1985424, US 2016962 and US 2703798 and international patent application WO 92/0698 An overview of this topic by H. Kelkenberg can be found in Tens. Surf.Det. J25, 8 (1988).
- the fatty acid N-alkylpolyhydroxyalkylamides are preferably derived from reducing sugars with 5 or 6 carbon atoms, in particular from glucose.
- the preferred fatty acid N-alkyl polyhydroxyalkylamides are therefore fatty acid re-N-alkylglucamides, as represented by the formula (III):
- Glucamides of the formula (III) in which R3 is hydrogen or an amine group and R 2 CO is the acyl radical of caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmoleic acid are preferably used as the fatty acid N-alkylpolyhydroxyalkylamides , Stearic acid, isostearic acid, oleic acid, elaidic acid, petroseline acid, linoleic acid, linolenic acid, arachidic acid, gadoleic acid, behenic acid or erucic acid or their technical mixtures.
- fatty acid N-alkyl glucamides of the formula (III) which are obtained by reductive amination of glucose with methylamine and subsequent acylation with lauric acid or C 2/14 coconut fatty acid or a corresponding derivative.
- the polyhydroxyalkylamides can also be derived from maltose and palatinose.
- aqueous preparations are dried which, in addition to sugar surfactants, additionally contain anionic surfactants.
- anionic surfactants Typical examples of this are alkylbenzenesulfonates, alkanesulfonates, olefinsulfonates, alkylethersulfonates, glycerol ether sulfonates, o-methyl ester sulfonates, sulfofatty acids, alkyl and / or alkenyl sulfates, fatty alcohol ether sulfates, glycerol ether sulfates, mono-ether ether sulfates, fatty acid ether amide sulfates, hydroxymethyl ether sulfates, ether) sulfates, mono- and dialkylsulfosuccinates, mono- and dialkylsulfosuccinamates, sulfotetriglycerides, amide soaps, amide soaps,
- aqueous preparations are dried which, in addition to the sugar tensides, contain alkyl and / or alkenyl sulfates as anionic surfactants.
- alkyl and / or alkenyl sulfates are to be understood as meaning the sulfation products of primary alcohols which follow the formula (XV)
- R ⁇ for a linear or branched, aliphatic alkyl and / or alkenyl radical having 6 to 22, preferably 12 to 18 carbon atoms and X for an alkyl and / or Alkaline earth metal, ammonium, alkylammonium, alkanolammonium or glucammonium.
- alkyl sulfates that can be used for the purposes of the invention are the sulfation products of capron alcohol, caprylic alcohol, capric alcohol, 2-ethylhexyl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, palm oleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elayl alcohol, elaalyl alcohol , Arachyl alcohol, gadoleyl alcohol, behenyl alcohol and erucyl alcohol as well as their technical mixtures, which are obtained by high pressure hydrogenation of technical methyl ester fractions or aldehydes from the Roelen oxo synthesis.
- the sulfation products can preferably be used in the form of their alkali metal salts, and in particular their sodium salts.
- R 4 stands for an alkyl radical with 12 to 18 carbon atoms and X for sodium, with the proviso that the ratio of alkyl radicals with 16 to 18 on the one hand and 12 to 14 carbon atoms on the other hand is 50: 50 to 90: 10 parts by weight .
- Aqueous preparations which may contain the sugar surfactants mentioned and, in addition, anionic surfactants are to be understood as solutions or pastes which have a solids content of 5 to 70, preferably 40 to 60% by weight.
- formic acid or formate it has proven to be particularly advantageous to use the preparations at a pH of 6 to 11, preferably 6.5 to 9.
- citric acid is suitable for pH adjustment.
- Typical examples are the two products from Henkel KGaA, Düsseldorf / FRG "sodium water glass N50 / 55 (module 2.0)” and “sodium water glass N37 / 40 (module 3.45)” as well as the magnesium silicate Optigel ( R ) SH, Südchemie AG, Kunststoff / FRG.
- the alkali and / or alkaline earth silicates can be used in amounts of 0.1 to 50, preferably 15 to 30% by weight, based on the solids content in the resulting powders.
- the alkali silicates are preferred as carriers, but they can easily be combined with other materials, e.g. inorganic or organic salts are mixed.
- Typical examples of inorganic salts are alkali and / or alkaline earth oxides, sulfates, carbonates, bicarbonates, phosphates, pyrophosphates, silicates and halides.
- the use of sodium sulfate, sodium carbonate, calcium carbonate, sodium phosphate, calcium pyrophosphate, sodium chloride, layer silicates, zeolites, hydrotalcites and magnesium oxide is particularly preferred.
- Aerosils are built from amorphous, spherical particles that have a diameter of 10 to 20 nm and an inner surface of 100 to 400 m 2 '?. exhibit. Aerosils have SiOH groups on their surface, which are linked to one another via relatively weak hydrogen bonds, which leads to the formation of scaffolds. Aerosils are, for example, sales products from Degussa, Hanau / FRG. For more information on their structure, see Soap-oils-fat waxes, 9 ⁇ , 849 (1968).
- organic salts are alkali and / or alkaline earth soaps, in particular sodium acetate, magnesium stearate and calcium stearate.
- Polysaccharides such as, for example, native and / or chemically modified, acid-degraded (maize) starch are suitable as further organic carriers. The latter is advantageous with a view to increasing the gelatinization temperature of the powder.
- the proportion of said co-carriers in the total amount of the carrier material can be 1 to 25, preferably 5 to 15% by weight.
- the aqueous preparations of the nonionic surfactants are treated together with the salts and optionally carrier substances with the exclusion of atmospheric oxygen in the presence of superheated steam.
- the principle of this new technical process was described by the applicant in her German tentanmel-fertilize DE-Al 4030688, DE-Al 4204035, DE-Al 4204090, DE-Al 4206050, DE-Al 4206495 and DE-Al 4206521.
- the method is based on the principle that, by condensing the superheated steam on the cooler feed and releasing the heat of condensation to the material to be dried, the aqueous drop spontaneously heats up to the boiling point of the water under working conditions, ie at normal pressure to temperatures of about 100 ° C, takes place. This boiling temperature is maintained as the minimum temperature during the entire residence time in the droplet. Steam-volatile impurities, such as fatty alcohols or formic acid, which cannot be removed by distillation under normal conditions or only under drastic conditions and with great technical effort, are quickly, completely and gently removed with the water phase.
- the aqueous preparations are sprayed together with superheated steam at a temperature in the range from 150 to 225 ° C. into a closed system, the condensate water with the impurities dissolved therein is separated off and the dried and cleaned valuable substances ejected.
- the closed system works with a water vapor circuit flow, from which the evaporated water portion of the feed material is extracted, while the amount of energy given off is returned to the circuit flow. While in conventional processes, working at higher temperatures always involves the risk of partial Charring of the material to be cleaned is connected, the absence of atmospheric oxygen makes working temperatures of in particular 150 to 225 and preferably 170 to 200 ° C. readily possible. After the dissolved impurities have been separated off, the partial steam stream which is drawn off can advantageously be supplied as process steam for other use.
- sugar surfactant powders with particularly advantageous free-flowing properties can be obtained by treating ("powdering") the dried valuable materials with suitable finely divided solids in order to reliably rule out any residual tack that may still be present.
- solids that come into consideration here are either substances which have already been mentioned as suitable carriers in the steam treatment or which are used in any case in surface-active agents. Typical examples are salts, such as, for example, silicates, sodium chloride, sodium sulfate, sodium phosphate, sodium pyrophosphate, calcium stearate and in particular silica with a high internal surface area (aerosils).
- the solids for powdering are usually used in an amount of 0.1 to 5, preferably 0.5 to 1% by weight, based on the sugar surfactant powder.
- the powdering can be done subsequently.
- the powdering preferably takes place in the spray tower, thereby ensuring a uniform powder discharge and baking of the Tower wall is reliably avoided.
- the powder is applied to the top of the drying tower.
- the carrier material for powdering.
- the amount of the powdering agent preferably makes up about 30% of the total amount of carrier, which in a very favorable case is about 30% by weight, based on the resulting dried material. Powdering is particularly advantageous if the sugar surfactant content in the powders is above 50% by weight. Voluminous agglomerates can form during powdering, but they quickly disintegrate on cooling and mechanical movement.
- auxiliaries and additives that are required for later assembly can be added to the sugar surfactant powders afterwards.
- these constituents, together with the sugar surfactants, to steam treatment with sufficient thermal stability can be added to the sugar surfactant powders afterwards.
- nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, polyol fatty acid sorbates, sugar esters, sugar esters. If the nonionic surfactants are polyglycol ether chains, they can have a conventional, but preferably a narrow homolog distribution.
- cationic surfactants are quaternary ammonium compounds and quaternized difatty acid trialkanolamine amines.
- amphoteric or zwitterionic surfactants are alkylbetaines, alkylamidobetaines, aminopropionates, aminoglycinates, imidaz ⁇ liniumbetaines and sulfobetaines.
- aroma components for example peppermint oil, spearmint oil, anise oil, star anise oil, caraway oil, eucalyptus oil, fennel oil, cinnamon oil, clove oil, geranium oil, sage oil, allspice oil, thyme oil, marjoram oil, are further auxiliaries and additives.
- Other suitable flavors are eg methyl acetate, vanillin, ionone, linalyl acetate, rhodinol and piperiton.
- Suitable sweeteners are either natural sugars such as suerose, maltose, lactose and fructose or synthetic sweeteners such as saccharin sodium salt, sodium cyclamate or aspartame.
- humectants such as e.g. Sorbitol or glycerin, consistency regulators, deodorising agents, agents against mouth and tooth diseases, water-soluble fluorine compounds such as Sodium fluoride or sodium monofluorophosphate and grinding or polishing agents.
- auxiliaries and additives are not critical per se and depends on the type of agent that is ultimately to be assembled.
- the proportion will usually be 5 to 70 and preferably 10 to 50% by weight, based on the sugar surfactant powder.
- the sugar surfactant powders obtainable by the process according to the invention contain less than 10, preferably less than 5 and in particular less than 1% by weight of water. They have excellent flow properties, do not stick, are readily water-soluble and are distinguished by excellent smell and taste properties. Another object of the invention therefore relates to their use for the production of surface-active, preferably cosmetic agents such as toothpastes or syndet soaps, in which they are present in amounts of 0.5 to 50, preferably 1 to 10% by weight, based on the means - can be included.
- Ci2 / 14- coconut -atty acid-N-methylglucamide (50% by weight solids).
- the residence time in the drying apparatus was about 10 seconds.
- the impurities entrained by the water vapor could be separated from the condensed water after the condensation in a two-phase separation or by micro- or ultrafiltration.
- the test results are summarized in Table 2 (percentages as% by weight).
- [X] concentration of X (based on the end product)
- Tl sodium sulfate
- T2 hydrophilized SiO 2 (Aerosil ( R ) R 972)
- T3 methyl cellulose (culminal ( R ))
- T7 magnesium silicate (Optigel ( R ) SH)
- a mixture of 70% by weight of Plantaren ( R ) APG 1200 CS UP and 30% by weight of sodium water glass N55 was dewatered in a rotary evaporator.
- the examples and comparative examples show that mixtures of sugar surfactants and anionic surfactants in superheated steam drying lead to products with a water solubility which is improved synergistically compared to the starting materials and advantageously high bulk densities of 400 to 550 g / l. Compared to conventional drying processes, powders with improved water solubility and color are finally obtained. Free-flowing and sticky products.
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Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP7514826A JPH09505621A (ja) | 1993-11-24 | 1994-11-22 | 無水かつ流動性の糖テンシド粉末の製造方法 |
EP95902081A EP0730484A1 (de) | 1993-11-24 | 1994-11-22 | Verfahren zur herstellung wasserfreier, rieselfähiger zuckertensidpulver |
KR1019960702663A KR960705608A (ko) | 1993-11-24 | 1994-11-22 | 무수, 자유 유동 당 계면 활성제 분말의 제조 방법(process for producing anhydrous pourable sugar tenside powders) |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP4340015.9 | 1993-11-24 | ||
DE4340015A DE4340015C2 (de) | 1993-11-24 | 1993-11-24 | Verfahren zur Herstellung wasserfreier, rieselfähiger Zuckertensidpulver und deren Verwendung |
DEP4431157.5 | 1994-09-01 | ||
DE4431157 | 1994-09-01 |
Publications (1)
Publication Number | Publication Date |
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WO1995014519A1 true WO1995014519A1 (de) | 1995-06-01 |
Family
ID=25931484
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/EP1994/003855 WO1995014519A1 (de) | 1993-11-24 | 1994-11-22 | Verfahren zur herstellung wasserfreier, rieselfähiger zuckertensidpulver |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0730484A1 (de) |
JP (1) | JPH09505621A (de) |
KR (1) | KR960705608A (de) |
CN (1) | CN1135724A (de) |
WO (1) | WO1995014519A1 (de) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1997003165A1 (de) * | 1995-07-10 | 1997-01-30 | Henkel Kommanditgesellschaft Auf Aktien | Verfahren zur herstellung von zuckertensidgranulaten |
DE19534371C1 (de) * | 1995-09-15 | 1997-02-20 | Henkel Kgaa | Verfahren zur Herstellung wasser- und staubfreier Zuckertensidgranulate |
WO1997010049A1 (de) * | 1995-09-11 | 1997-03-20 | Henkel Kommanditgesellschaft Auf Aktien | O/w-emulgatoren |
EP0780464A3 (de) * | 1995-12-21 | 1998-12-02 | Henkel Kommanditgesellschaft auf Aktien | Verfahren zur Herstellung hellfarbiger, niedrigviskoser Tensidkonzentrate |
WO2001046375A1 (de) * | 1999-12-17 | 2001-06-28 | Henkel Kommanditgesellschaft Auf Aktien | Verfahren zur herstellung von zuckertensidgranulaten |
US6340665B1 (en) | 1997-03-12 | 2002-01-22 | Henkel Kommanditgesellschaft Auf Aktien | Method for producing neutral sugar surfactant granulates |
US6846796B2 (en) | 2000-04-15 | 2005-01-25 | Cognis Deutschland Gmbh & Co. Kg | Method for producing non-ionic tenside granulates |
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DE4030688A1 (de) * | 1990-09-28 | 1992-04-02 | Henkel Kgaa | Verfahren zur spruehtrocknung von wertstoffen und wertstoffgemischen unter verwendung von ueberhitztem wasserdampf |
WO1993015813A1 (de) * | 1992-02-12 | 1993-08-19 | Henkel Kommanditgesellschaft Auf Aktien | Verfahren zur herstellung von granulaten, die als netz-, wasch- und/oder reinigungsmittel geeignet sind |
WO1994009109A1 (de) * | 1992-10-12 | 1994-04-28 | Henkel Kommanditgesellschaft Auf Aktien | Wertstoffe und wertstoffgemische für netz-, wasch- und/oder reinigungsmittel in neuer zubereitungsform |
-
1994
- 1994-11-22 EP EP95902081A patent/EP0730484A1/de not_active Withdrawn
- 1994-11-22 CN CN94194235A patent/CN1135724A/zh active Pending
- 1994-11-22 KR KR1019960702663A patent/KR960705608A/ko not_active Application Discontinuation
- 1994-11-22 JP JP7514826A patent/JPH09505621A/ja active Pending
- 1994-11-22 WO PCT/EP1994/003855 patent/WO1995014519A1/de not_active Application Discontinuation
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DE4030688A1 (de) * | 1990-09-28 | 1992-04-02 | Henkel Kgaa | Verfahren zur spruehtrocknung von wertstoffen und wertstoffgemischen unter verwendung von ueberhitztem wasserdampf |
WO1992005849A1 (de) * | 1990-09-28 | 1992-04-16 | Henkel Kommanditgesellschaft Auf Aktien | Verfahren zur sprühtrocknung von wertstoffen und wertstoffgemiscehen unter verwendung von überhitztem wasserdampf |
WO1993015813A1 (de) * | 1992-02-12 | 1993-08-19 | Henkel Kommanditgesellschaft Auf Aktien | Verfahren zur herstellung von granulaten, die als netz-, wasch- und/oder reinigungsmittel geeignet sind |
WO1994009109A1 (de) * | 1992-10-12 | 1994-04-28 | Henkel Kommanditgesellschaft Auf Aktien | Wertstoffe und wertstoffgemische für netz-, wasch- und/oder reinigungsmittel in neuer zubereitungsform |
Cited By (12)
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WO1997003165A1 (de) * | 1995-07-10 | 1997-01-30 | Henkel Kommanditgesellschaft Auf Aktien | Verfahren zur herstellung von zuckertensidgranulaten |
US6030937A (en) * | 1995-07-10 | 2000-02-29 | Henkel Kommanditgesellschaft Auf Aktien | Method of preparing saccharose surfactant granulates |
WO1997010049A1 (de) * | 1995-09-11 | 1997-03-20 | Henkel Kommanditgesellschaft Auf Aktien | O/w-emulgatoren |
AU704033B2 (en) * | 1995-09-11 | 1999-04-15 | Cognis Deutschland Gmbh & Co. Kg | Oil-water emulsifiers |
CN1092995C (zh) * | 1995-09-11 | 2002-10-23 | 汉克尔股份两合公司 | 水包油乳化剂 |
DE19534371C1 (de) * | 1995-09-15 | 1997-02-20 | Henkel Kgaa | Verfahren zur Herstellung wasser- und staubfreier Zuckertensidgranulate |
EP0780464A3 (de) * | 1995-12-21 | 1998-12-02 | Henkel Kommanditgesellschaft auf Aktien | Verfahren zur Herstellung hellfarbiger, niedrigviskoser Tensidkonzentrate |
US6340665B1 (en) | 1997-03-12 | 2002-01-22 | Henkel Kommanditgesellschaft Auf Aktien | Method for producing neutral sugar surfactant granulates |
WO2001046375A1 (de) * | 1999-12-17 | 2001-06-28 | Henkel Kommanditgesellschaft Auf Aktien | Verfahren zur herstellung von zuckertensidgranulaten |
DE19961333A1 (de) * | 1999-12-17 | 2001-07-05 | Henkel Kgaa | Verfahren zur Herstellung von Zuckertensidgranulaten |
DE19961333B4 (de) * | 1999-12-17 | 2006-12-14 | Henkel Kgaa | Verfahren zur Herstellung von Zuckertensidgranulaten |
US6846796B2 (en) | 2000-04-15 | 2005-01-25 | Cognis Deutschland Gmbh & Co. Kg | Method for producing non-ionic tenside granulates |
Also Published As
Publication number | Publication date |
---|---|
JPH09505621A (ja) | 1997-06-03 |
KR960705608A (ko) | 1996-11-08 |
CN1135724A (zh) | 1996-11-13 |
EP0730484A1 (de) | 1996-09-11 |
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