SK32094A3 - Method of preparing of alkylpolyglucosides - Google Patents

Method of preparing of alkylpolyglucosides Download PDF

Info

Publication number: SK32094A3
Authority: SK; Slovakia
Prior art keywords: catalyst; acid; glucose; alkyl; alcohol
Prior art date: 1993-03-19

Application number

SK320-94A

Other languages

English (en)

Slovak (sk)

Inventor

Borsotti Giampietroara No

Tullio Pellizzon

Original Assignee

Eniricerche Spa

Enichem Spa

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1993-03-19

Filing date

1994-03-17

Publication date

1994-11-09

1994-03-17 Application filed by Eniricerche Spa, Enichem Spa filed Critical Eniricerche Spa

1994-11-09 Publication of SK32094A3 publication Critical patent/SK32094A3/sk

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)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Crystallography & Structural Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Saccharide Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)
Silicon Polymers (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Detergent Compositions (AREA)
Light Receiving Elements (AREA)
Apparatus For Radiation Diagnosis (AREA)

SK320-94A 1993-03-19 1994-03-17 Method of preparing of alkylpolyglucosides SK32094A3 (en)

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 (de)
EP (1)	EP0619318B1 (de)
JP (1)	JPH06298787A (de)
AT (1)	ATE142634T1 (de)
CA (1)	CA2119414A1 (de)
CZ (1)	CZ289126B6 (de)
DE (1)	DE69400496T2 (de)
DK (1)	DK0619318T3 (de)
ES (1)	ES2094022T3 (de)
GR (1)	GR3021835T3 (de)
IT (1)	IT1272109B (de)
SK (1)	SK32094A3 (de)

Families Citing this family (67)

* Cited by examiner, † Cited by third party
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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
US6531435B1 (en)	2000-11-28	2003-03-11	Kimberly-Clark Worldwide, Inc.	Compositions 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
US6656913B1 (en)	2000-11-28	2003-12-02	Kimberly-Clark Worldwide, Inc.	Inhibition of exoprotein production from gram positive bacteria
US6599521B1 (en)	2000-11-28	2003-07-29	Kimberly-Clark Worldwide, Inc.	Absorbent articles for the 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
US7026354B2 (en) *	2001-10-02	2006-04-11	Kimberly-Clark Worldwide, Inc.	Aromatic compositions for the inhibition of exoprotein production from gram positive bacteria
US8084046B2 (en) *	2001-10-02	2011-12-27	Kimberly-Clark Worldwide, Inc.	Inhibition of exoprotein production in absorbent articles using isoprenoids
US6596290B2 (en)	2001-10-02	2003-07-22	Kimberly-Clark Worldwide, Inc.	Inhibition of exoprotein production in non-absorbent articles using isoprenoid compositions
US7022333B2 (en) *	2001-10-02	2006-04-04	Kimberly-Clark Worldwide, Inc.	Inhibition of exoprotein production in non-absorbent articles uisng aromatic compositions
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1993
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1994
- 1994-03-11 CZ CZ1994565A patent/CZ289126B6/cs not_active IP Right Cessation
- 1994-03-15 ES ES94200660T patent/ES2094022T3/es not_active Expired - Lifetime
- 1994-03-15 DE DE69400496T patent/DE69400496T2/de not_active Expired - Fee Related
- 1994-03-15 EP EP94200660A patent/EP0619318B1/de not_active Expired - Lifetime
- 1994-03-15 DK DK94200660.2T patent/DK0619318T3/da active
- 1994-03-15 AT AT94200660T patent/ATE142634T1/de not_active IP Right Cessation
- 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
EP0619318B1 (de)	1996-09-11
GR3021835T3 (en)	1997-02-28
US5527892A (en)	1996-06-18
IT1272109B (it)	1997-06-11
DE69400496D1 (de)	1996-10-17
ATE142634T1 (de)	1996-09-15
DK0619318T3 (da)	1996-12-30
EP0619318A1 (de)	1994-10-12
JPH06298787A (ja)	1994-10-25
ES2094022T3 (es)	1997-01-01
ITMI930518A0 (it)	1993-03-19
ITMI930518A1 (it)	1994-09-19
CZ56594A3 (en)	1994-10-19
CA2119414A1 (en)	1994-09-20
DE69400496T2 (de)	1997-03-27
CZ289126B6 (cs)	2001-11-14

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