SK32094A3 - Method of preparing of alkylpolyglucosides - Google Patents
Method of preparing of alkylpolyglucosides Download PDFInfo
- Publication number
- SK32094A3 SK32094A3 SK320-94A SK32094A SK32094A3 SK 32094 A3 SK32094 A3 SK 32094A3 SK 32094 A SK32094 A SK 32094A SK 32094 A3 SK32094 A3 SK 32094A3
- Authority
- SK
- Slovakia
- Prior art keywords
- catalyst
- acid
- glucose
- alkyl
- alcohol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 40
- 239000003054 catalyst Substances 0.000 claims abstract description 45
- 238000006243 chemical reaction Methods 0.000 claims abstract description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 34
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- -1 aryl sulfonic acid Chemical compound 0.000 claims abstract description 15
- 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 claims description 36
- 239000008103 glucose Substances 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 23
- 150000002772 monosaccharides Chemical class 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 7
- 229930182478 glucoside Natural products 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 6
- YHGKEORTCHVBQH-UHFFFAOYSA-N 2,4,6-tri(propan-2-yl)benzenesulfonic acid Chemical compound CC(C)C1=CC(C(C)C)=C(S(O)(=O)=O)C(C(C)C)=C1 YHGKEORTCHVBQH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- UIFIXPPGHGXDRG-UHFFFAOYSA-N 2,2,6,6-tetra(propan-2-yl)cyclohexane-1-sulfonic acid Chemical compound CC(C)C1(C(C)C)CCCC(C(C)C)(C(C)C)C1S(O)(=O)=O UIFIXPPGHGXDRG-UHFFFAOYSA-N 0.000 claims description 3
- SNUPPHSJKPQPDV-UHFFFAOYSA-N 2,4,6-tris(2-methylpropyl)benzenesulfonic acid Chemical compound CC(C)CC1=CC(CC(C)C)=C(S(O)(=O)=O)C(CC(C)C)=C1 SNUPPHSJKPQPDV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- OMSKDKWDCKLUDG-UHFFFAOYSA-N 2,6-dimethyl-3,5-di(propan-2-yl)heptane-4-sulfonic acid Chemical compound CC(C)C(C(C)C)C(S(O)(=O)=O)C(C(C)C)C(C)C OMSKDKWDCKLUDG-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000002402 hexoses Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 125000002346 iodo group Chemical group I* 0.000 claims description 2
- 150000002972 pentoses Chemical class 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 12
- 239000006227 byproduct Substances 0.000 abstract description 3
- 239000004094 surface-active agent Substances 0.000 abstract description 3
- 229930182470 glycoside Natural products 0.000 abstract 1
- 150000002338 glycosides Chemical class 0.000 abstract 1
- 230000003407 synthetizing effect Effects 0.000 abstract 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 34
- 229960001031 glucose Drugs 0.000 description 34
- 150000001298 alcohols Chemical class 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 7
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000005755 formation reaction Methods 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 229920002472 Starch Polymers 0.000 description 4
- 150000001720 carbohydrates Chemical class 0.000 description 4
- 235000014633 carbohydrates Nutrition 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 150000003460 sulfonic acids Chemical class 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 3
- 229920001282 polysaccharide Polymers 0.000 description 3
- 239000005017 polysaccharide Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000008052 alkyl sulfonates Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229940077731 carbohydrate nutrients Drugs 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- 150000000180 1,2-diols Chemical class 0.000 description 1
- 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 1
- HXPRELFGIZAIDS-UHFFFAOYSA-N 2,2,6,6-tetraethylcyclohexane-1-sulfonic acid Chemical compound CCC1(CC)CCCC(CC)(CC)C1S(O)(=O)=O HXPRELFGIZAIDS-UHFFFAOYSA-N 0.000 description 1
- MCRGETXDQPIYLC-UHFFFAOYSA-N 2,4,6-triethoxybenzenesulfonic acid Chemical compound CCOC1=CC(OCC)=C(S(O)(=O)=O)C(OCC)=C1 MCRGETXDQPIYLC-UHFFFAOYSA-N 0.000 description 1
- IHGWXBWYZUMHLR-UHFFFAOYSA-N 2,4,6-triethylbenzenesulfonic acid Chemical compound CCC1=CC(CC)=C(S(O)(=O)=O)C(CC)=C1 IHGWXBWYZUMHLR-UHFFFAOYSA-N 0.000 description 1
- LXFQSRIDYRFTJW-UHFFFAOYSA-N 2,4,6-trimethylbenzenesulfonic acid Chemical compound CC1=CC(C)=C(S(O)(=O)=O)C(C)=C1 LXFQSRIDYRFTJW-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- YZTJKOLMWJNVFH-UHFFFAOYSA-N 2-sulfobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1S(O)(=O)=O YZTJKOLMWJNVFH-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 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 1
- 239000004435 Oxo alcohol Substances 0.000 description 1
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- CJMZLCRLBNZJQR-UHFFFAOYSA-N ethyl 2-amino-4-(4-fluorophenyl)thiophene-3-carboxylate Chemical compound CCOC(=O)C1=C(N)SC=C1C1=CC=C(F)C=C1 CJMZLCRLBNZJQR-UHFFFAOYSA-N 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229940043348 myristyl alcohol Drugs 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000003420 transacetalization reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Saccharide Compounds (AREA)
- Silicon Polymers (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Apparatus For Radiation Diagnosis (AREA)
- Light Receiving Elements (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI930518A IT1272109B (it) | 1993-03-19 | 1993-03-19 | Processo per la preparazione di apg |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK32094A3 true SK32094A3 (en) | 1994-11-09 |
Family
ID=11365397
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK320-94A SK32094A3 (en) | 1993-03-19 | 1994-03-17 | Method of preparing of alkylpolyglucosides |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5527892A (it) |
| EP (1) | EP0619318B1 (it) |
| JP (1) | JPH06298787A (it) |
| AT (1) | ATE142634T1 (it) |
| CA (1) | CA2119414A1 (it) |
| CZ (1) | CZ289126B6 (it) |
| DE (1) | DE69400496T2 (it) |
| DK (1) | DK0619318T3 (it) |
| ES (1) | ES2094022T3 (it) |
| GR (1) | GR3021835T3 (it) |
| IT (1) | IT1272109B (it) |
| SK (1) | SK32094A3 (it) |
Families Citing this family (66)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4431852A1 (de) * | 1994-09-07 | 1996-03-14 | Huels Chemische Werke Ag | Verfahren zur Bleichung von Alkylpolyglycosiden |
| JPH0931089A (ja) * | 1995-07-20 | 1997-02-04 | T Hasegawa Co Ltd | グルコシド類の製法 |
| DE19710112A1 (de) * | 1997-03-12 | 1998-09-17 | Henkel Kgaa | Verfahren zur kontinuierlichen Herstellung von Alkyl- und/oder Alkenyloligoglykosiden |
| IT1295934B1 (it) * | 1997-10-30 | 1999-05-28 | Condea Augusta Spa | Procedimento migliorato per la sintesi di alchilpoliglucosidi |
| DE10041577A1 (de) * | 2000-08-24 | 2002-03-14 | Inst Technologie Der Kohlenhyd | Verfahren zur Herstellung von Alkylglycosiden, insbesondere Alkylfructosiden |
| US6599521B1 (en) | 2000-11-28 | 2003-07-29 | Kimberly-Clark Worldwide, Inc. | Absorbent articles for the inhibition of exoprotein production from Gram positive bacteria |
| US6676957B1 (en) | 2000-11-28 | 2004-01-13 | Kimberly-Clark Worldwide, Inc. | Non-absorbent substrates for the inhibition of exoprotein production from gram positive bacteria |
| US6531435B1 (en) | 2000-11-28 | 2003-03-11 | Kimberly-Clark Worldwide, Inc. | Compositions for the inhibition of exoprotein production from Gram positive bacteria |
| US6656913B1 (en) * | 2000-11-28 | 2003-12-02 | Kimberly-Clark Worldwide, Inc. | Inhibition of exoprotein production from gram positive bacteria |
| KR20030016819A (ko) * | 2001-08-22 | 2003-03-03 | 한국산노프코 주식회사 | 반응성을 향상시킨 글루코즈 적하방식을 통한알킬폴리글루코자이드의 제조방법 |
| US6534548B1 (en) | 2001-10-02 | 2003-03-18 | Kimberly-Clark Worldwide, Inc. | Isoprenoid compositions for the inhibition of exoprotein production from gram positive bacteria |
| US6596290B2 (en) | 2001-10-02 | 2003-07-22 | Kimberly-Clark Worldwide, Inc. | Inhibition of exoprotein production in non-absorbent articles using isoprenoid compositions |
| US8084046B2 (en) * | 2001-10-02 | 2011-12-27 | Kimberly-Clark Worldwide, Inc. | Inhibition of exoprotein production in absorbent articles using isoprenoids |
| US7026354B2 (en) | 2001-10-02 | 2006-04-11 | Kimberly-Clark Worldwide, Inc. | Aromatic compositions for the inhibition of exoprotein production from gram positive bacteria |
| US7022333B2 (en) * | 2001-10-02 | 2006-04-04 | Kimberly-Clark Worldwide, Inc. | Inhibition of exoprotein production in non-absorbent articles uisng aromatic compositions |
| TWI264121B (en) | 2001-11-30 | 2006-10-11 | Semiconductor Energy Lab | A display device, a method of manufacturing a semiconductor device, and a method of manufacturing a display device |
| US7004928B2 (en) | 2002-02-08 | 2006-02-28 | Rosedale Medical, Inc. | Autonomous, ambulatory analyte monitor or drug delivery device |
| US20060067990A1 (en) * | 2004-09-30 | 2006-03-30 | Kimberly-Clark Worldwide, Inc. | Absorbent articles for inhibiting the production of exoproteins |
| US20060067991A1 (en) * | 2004-09-30 | 2006-03-30 | Kimberly-Clark Worldwide, Inc. | Non-absorbent articles for inhibiting the production of exoproteins |
| US7619008B2 (en) * | 2004-11-12 | 2009-11-17 | Kimberly-Clark Worldwide, Inc. | Xylitol for treatment of vaginal infections |
| US20060106117A1 (en) * | 2004-11-12 | 2006-05-18 | Kimberly-Clark Worldwide, Inc. | Compound and method for prevention and/or treatment of vaginal infections |
| US20060223765A1 (en) * | 2005-03-30 | 2006-10-05 | Kimberly-Clark Worldwide, Inc. | Method for inhibiting and/or treating vaginal infection |
| US20060281187A1 (en) | 2005-06-13 | 2006-12-14 | Rosedale Medical, Inc. | Analyte detection devices and methods with hematocrit/volume correction and feedback control |
| US7786176B2 (en) | 2005-07-29 | 2010-08-31 | Kimberly-Clark Worldwide, Inc. | Vaginal treatment composition containing xylitol |
| US20070048345A1 (en) * | 2005-08-31 | 2007-03-01 | Kimberly-Clark Worldwide, Inc. | Antimicrobial composition |
| US20070048344A1 (en) * | 2005-08-31 | 2007-03-01 | Ali Yahiaoui | Antimicrobial composition |
| US20070048358A1 (en) * | 2005-08-31 | 2007-03-01 | Schorr Phillip A | Antimicrobial substrates |
| US20070048356A1 (en) * | 2005-08-31 | 2007-03-01 | Schorr Phillip A | Antimicrobial treatment of nonwoven materials for infection control |
| CA2624117C (en) | 2005-09-30 | 2014-06-17 | Intuity Medical, Inc. | Fully integrated wearable or handheld monitor |
| US8187697B2 (en) * | 2007-04-30 | 2012-05-29 | Kimberly-Clark Worldwide, Inc. | Cooling product |
| US9657257B2 (en) * | 2007-05-10 | 2017-05-23 | Kimberly-Clark Worldwide, Inc. | Colorant neutralizer |
| US20080276379A1 (en) * | 2007-05-10 | 2008-11-13 | Macdonald John Gavin | Methods for discharging colorants |
| US7879744B2 (en) | 2007-08-30 | 2011-02-01 | Kimberly-Clark Worldwide, Inc. | Stabilized decolorizing composition |
| US20090062764A1 (en) * | 2007-08-30 | 2009-03-05 | Kimberly-Clark Worldwide, Inc. | Zoned application of decolorizing composition for use in absorbent articles |
| US8569221B2 (en) * | 2007-08-30 | 2013-10-29 | Kimberly-Clark Worldwide, Inc. | Stain-discharging and removing system |
| US8535617B2 (en) * | 2007-11-30 | 2013-09-17 | Kimberly-Clark Worldwide, Inc. | Blood cell barrier for a lateral flow device |
| US8563017B2 (en) * | 2008-05-15 | 2013-10-22 | Kimberly-Clark Worldwide, Inc. | Disinfectant wet wipe |
| ES2907152T3 (es) | 2008-06-06 | 2022-04-22 | Intuity Medical Inc | Medidor de glucosa en sangre y método de funcionamiento |
| JP5642066B2 (ja) | 2008-06-06 | 2014-12-17 | インテュイティ メディカル インコーポレイテッド | 体液の試料内に含まれている検体の存在または濃度を決定する検定を行う方法および装置 |
| US8691301B2 (en) * | 2008-06-30 | 2014-04-08 | Kimberly-Clark Worldwide, Inc. | Surfactant gas pressurized liquid composition and method and package for delivering |
| DE102009029194A1 (de) | 2009-09-04 | 2011-04-07 | Kimberly-Clark Worldwide, Inc., Neenah | Abtrennung gefärbter Stoffe aus wasserhaltigen Flüssigkeiten |
| WO2011065981A1 (en) | 2009-11-30 | 2011-06-03 | Intuity Medical, Inc. | Calibration material delivery devices and methods |
| WO2011162823A1 (en) | 2010-06-25 | 2011-12-29 | Intuity Medical, Inc. | Analyte monitoring methods and systems |
| WO2013040174A1 (en) | 2011-09-13 | 2013-03-21 | Lubrizol Advanced Materials, Inc. | Surfactant responsive emulsion polymerized micro-gels |
| KR101963693B1 (ko) | 2011-09-13 | 2019-03-29 | 루브리졸 어드밴스드 머티어리얼스, 인코포레이티드 | 계면활성제 반응성 마이크로-겔 |
| KR101974993B1 (ko) | 2011-09-13 | 2019-05-03 | 루브리졸 어드밴스드 머티어리얼스, 인코포레이티드 | 계면활성제 반응성 분산 중합된 마이크로-겔 |
| US9161869B2 (en) | 2012-03-30 | 2015-10-20 | Kimberly-Clark Worldwide, Inc. | Absorbent articles with decolorizing agents |
| BR112015014442A2 (pt) | 2012-12-20 | 2017-07-11 | Lubrizol Advanced Mat Inc | método para reduzir irritação cutânea induzida por uma composição contendo tensoativo |
| BR112015014494A2 (pt) | 2012-12-20 | 2017-07-11 | Lubrizol Advanced Mat Inc | método para reduzir irritação da pele induzido por uma composição contendo tensoativo, e, composição |
| KR20150126894A (ko) | 2013-03-08 | 2015-11-13 | 루브리졸 어드밴스드 머티어리얼스, 인코포레이티드 | 비이온성의 양친매성 폴리머의 사용을 통한 클렌징 조성물의 개선된 발포 성능 |
| US20160015622A1 (en) | 2013-03-08 | 2016-01-21 | Lubrizol Advanced Materials Inc. | Surfactant Activated Microgel Polymers And Methods To Mitigate The Loss Of Silicone Deposition From Keratinous Substrates |
| US10729386B2 (en) | 2013-06-21 | 2020-08-04 | Intuity Medical, Inc. | Analyte monitoring system with audible feedback |
| US9237975B2 (en) | 2013-09-27 | 2016-01-19 | Kimberly-Clark Worldwide, Inc. | Absorbent article with side barriers and decolorizing agents |
| CN103613620B (zh) * | 2013-11-13 | 2016-06-08 | 广州大学 | 木薯淀粉制备十二烷基糖苷的方法 |
| AR098786A1 (es) | 2013-12-17 | 2016-06-15 | Lubrizol Advanced Mat Inc | Microgeles polimerizados en emulsión que responden a tensioactivos |
| BR112016014650A2 (pt) | 2013-12-23 | 2017-08-08 | Lubrizol Advanced Mat Inc | Composição anticaspa, e, método para melhorar a estabilidade da fase de uma composição de xampu anticaspa |
| EP3233943A1 (en) | 2014-12-17 | 2017-10-25 | Lubrizol Advanced Materials, Inc. | Surfactant responsive emulsion polymerized micro-gels |
| JP2017538732A (ja) | 2014-12-18 | 2017-12-28 | ルブリゾル アドバンスド マテリアルズ， インコーポレイテッド | フケ防止用ヘアケア組成物のための両親媒性懸濁安定剤 |
| BR112018012808A2 (pt) | 2015-12-23 | 2018-12-04 | Lubrizol Advanced Mat Inc | polímero de emulsão, e, composição. |
| BR112018012759A2 (pt) | 2015-12-23 | 2018-12-04 | Lubrizol Advanced Mat Inc | polímero de ase, e, composição aquosa contendo tensoativo. |
| EP3266859A1 (en) * | 2016-07-05 | 2018-01-10 | Basf Se | Composition suitable as degreasing agent for removing greasy and/or oil type deposits |
| JP7328893B2 (ja) | 2016-12-19 | 2023-08-17 | ルブリゾル アドバンスド マテリアルズ， インコーポレイテッド | 界面活性剤応答性乳化重合マイクロゲル |
| US11584903B2 (en) | 2017-10-05 | 2023-02-21 | Lubrizol Advanced Materials, Inc. | Structured unit dose cleansing product |
| EP3937900B1 (en) | 2019-03-14 | 2023-08-02 | Lubrizol Advanced Materials, Inc. | Enhanced silicon deposition compositions and method therefore |
| CN110305532A (zh) * | 2019-07-22 | 2019-10-08 | 浙江海印数码科技有限公司 | 一种数码印花用高浓度酸性墨水及其制备方法 |
| JP2023539093A (ja) | 2020-08-20 | 2023-09-13 | ザ ルブリゾル コーポレイション | 有機熱伝達システム、方法、及び流体 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4223129A (en) * | 1978-09-01 | 1980-09-16 | A. E. Staley Manufacturing Company | Continuous process for making alkyl aldosides from starch or other carbohydrates |
| US4393203B2 (en) * | 1982-04-26 | 1997-07-01 | Procter & Gamble | Process of preparing alkylpolysaccharides |
| US4713447A (en) * | 1983-06-30 | 1987-12-15 | The Procter & Gamble Company | Process for preparing alkyl glycosides |
| DE3468217D1 (en) * | 1983-06-15 | 1988-02-04 | Procter & Gamble | Improved process for preparing alkyl glycosides |
| EP0132046B1 (en) * | 1983-06-15 | 1988-04-20 | The Procter & Gamble Company | Improved process for preparing alkyl glycosides |
| US4950743A (en) * | 1987-07-29 | 1990-08-21 | Henkel Kommanditgesellschaft Auf Aktien | Process for preparation of alkylglycosides |
| US5003057A (en) * | 1988-12-23 | 1991-03-26 | Henkel Kommanditgesellschaft Auf Aktien | Process for production of glycosides |
| US5037992A (en) * | 1989-12-18 | 1991-08-06 | The Procter & Gamble Company | Process for sulfating unsaturated alcohols |
| US5266690A (en) * | 1991-12-19 | 1993-11-30 | Henkel Corporation | Preparation of alkylpolyglycosides |
| IT1255754B (it) * | 1992-05-15 | 1995-11-15 | Enichem Augusta Ind | Processo per la preparazione di alchilpoliglucosidi |
-
1993
- 1993-03-19 IT ITMI930518A patent/IT1272109B/it active IP Right Grant
-
1994
- 1994-03-11 CZ CZ1994565A patent/CZ289126B6/cs not_active IP Right Cessation
- 1994-03-15 AT AT94200660T patent/ATE142634T1/de not_active IP Right Cessation
- 1994-03-15 DE DE69400496T patent/DE69400496T2/de not_active Expired - Fee Related
- 1994-03-15 ES ES94200660T patent/ES2094022T3/es not_active Expired - Lifetime
- 1994-03-15 DK DK94200660.2T patent/DK0619318T3/da active
- 1994-03-15 EP EP94200660A patent/EP0619318B1/en not_active Expired - Lifetime
- 1994-03-16 US US08/213,702 patent/US5527892A/en not_active Expired - Lifetime
- 1994-03-17 SK SK320-94A patent/SK32094A3/sk unknown
- 1994-03-18 JP JP6074043A patent/JPH06298787A/ja not_active Withdrawn
- 1994-03-18 CA CA002119414A patent/CA2119414A1/en not_active Abandoned
-
1996
- 1996-11-29 GR GR960403232T patent/GR3021835T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE69400496D1 (de) | 1996-10-17 |
| DK0619318T3 (da) | 1996-12-30 |
| CZ289126B6 (cs) | 2001-11-14 |
| CA2119414A1 (en) | 1994-09-20 |
| ES2094022T3 (es) | 1997-01-01 |
| GR3021835T3 (en) | 1997-02-28 |
| ITMI930518A0 (it) | 1993-03-19 |
| ITMI930518A1 (it) | 1994-09-19 |
| CZ56594A3 (en) | 1994-10-19 |
| EP0619318B1 (en) | 1996-09-11 |
| EP0619318A1 (en) | 1994-10-12 |
| ATE142634T1 (de) | 1996-09-15 |
| IT1272109B (it) | 1997-06-11 |
| US5527892A (en) | 1996-06-18 |
| DE69400496T2 (de) | 1997-03-27 |
| JPH06298787A (ja) | 1994-10-25 |
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