CA2095879A1 - Carbohydrate derived surfactants and their precursors - Google Patents
Carbohydrate derived surfactants and their precursorsInfo
- Publication number
- CA2095879A1 CA2095879A1 CA002095879A CA2095879A CA2095879A1 CA 2095879 A1 CA2095879 A1 CA 2095879A1 CA 002095879 A CA002095879 A CA 002095879A CA 2095879 A CA2095879 A CA 2095879A CA 2095879 A1 CA2095879 A1 CA 2095879A1
- Authority
- CA
- Canada
- Prior art keywords
- general formula
- dialkylglycamine
- compound
- carbon atoms
- monosaccharide
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 239000004094 surface-active agent Substances 0.000 title abstract description 9
- 239000002243 precursor Substances 0.000 title description 2
- 150000001720 carbohydrates Chemical class 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 150000002772 monosaccharides Chemical class 0.000 claims abstract 3
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims abstract 2
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 claims abstract 2
- 125000001931 aliphatic group Chemical group 0.000 claims abstract 2
- 229960003237 betaine Drugs 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 239000012670 alkaline solution Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 230000000737 periodic effect Effects 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 abstract description 3
- 229910021653 sulphate ion Inorganic materials 0.000 abstract description 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 2
- 150000001340 alkali metals Chemical class 0.000 abstract description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 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 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 4
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 4
- 229940089960 chloroacetate Drugs 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- HSRJKNPTNIJEKV-UHFFFAOYSA-N Guaifenesin Chemical compound COC1=CC=CC=C1OCC(O)CO HSRJKNPTNIJEKV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- DGRPGFHRMFKIAV-UHFFFAOYSA-N 1,3,2-dioxaphospholan-2-ium 2-oxide Chemical compound O=[P+]1OCCO1 DGRPGFHRMFKIAV-UHFFFAOYSA-N 0.000 description 1
- YYTSGNJTASLUOY-UHFFFAOYSA-N 1-chloropropan-2-ol Chemical compound CC(O)CCl YYTSGNJTASLUOY-UHFFFAOYSA-N 0.000 description 1
- CLHYKAZPWIRRRD-UHFFFAOYSA-N 1-hydroxypropane-1-sulfonic acid Chemical compound CCC(O)S(O)(=O)=O CLHYKAZPWIRRRD-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- HSXUNHYXJWDLDK-UHFFFAOYSA-N 2-hydroxypropane-1-sulfonic acid Chemical compound CC(O)CS(O)(=O)=O HSXUNHYXJWDLDK-UHFFFAOYSA-N 0.000 description 1
- VLRGXXKFHVJQOL-UHFFFAOYSA-N 3-chloropentane-2,4-dione Chemical compound CC(=O)C(Cl)C(C)=O VLRGXXKFHVJQOL-UHFFFAOYSA-N 0.000 description 1
- SDOFMBGMRVAJNF-UHFFFAOYSA-N 6-aminohexane-1,2,3,4,5-pentol Chemical compound NCC(O)C(O)C(O)C(O)CO SDOFMBGMRVAJNF-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 101100116570 Caenorhabditis elegans cup-2 gene Proteins 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000905957 Channa melasoma Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RFSUNEUAIZKAJO-VRPWFDPXSA-N D-Fructose Natural products OC[C@H]1OC(O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-VRPWFDPXSA-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
- 101100116572 Drosophila melanogaster Der-1 gene Proteins 0.000 description 1
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 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 1
- 239000004471 Glycine Substances 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 241000252067 Megalops atlanticus Species 0.000 description 1
- 241000357437 Mola Species 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- 101150030413 Timp gene Proteins 0.000 description 1
- YGDMSOQVGXYMBY-UHFFFAOYSA-N [ClH](C)(=O)O Chemical compound [ClH](C)(=O)O YGDMSOQVGXYMBY-UHFFFAOYSA-N 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 238000004380 ashing Methods 0.000 description 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 1
- 210000001217 buttock Anatomy 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- MKXZASYAUGDDCJ-QNNIAVNKSA-N deudextromethorphan Chemical compound C([C@@H]12)CCC[C@]11CCN(C([2H])([2H])[2H])[C@H]2CC2=CC=C(OC([2H])([2H])[2H])C=C21 MKXZASYAUGDDCJ-QNNIAVNKSA-N 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002402 hexoses Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 125000006357 methylene carbonyl group Chemical group [H]C([H])([*:1])C([*:2])=O 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 101150050071 proY gene Proteins 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- LUIGSJYSMIUMPK-UHFFFAOYSA-N propane-1-sulfonoperoxoic acid Chemical compound CCCS(=O)(=O)OO LUIGSJYSMIUMPK-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- -1 thR monosaccharide Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C291/00—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
- C07C291/02—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds
- C07C291/04—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds containing amino-oxide bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/02—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of hydrogen atoms by amino groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/12—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of acyclic carbon skeletons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/13—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/14—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton containing amino groups bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Saccharide Compounds (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB929210094A GB9210094D0 (en) | 1992-05-11 | 1992-05-11 | Carbohydrate-derived surfactants |
| GB9210094.0 | 1992-05-11 | ||
| GB929210133A GB9210133D0 (en) | 1992-05-11 | 1992-05-11 | Carbohydrate-derived surfactants |
| GB9210133.6 | 1992-05-11 | ||
| GB9304273.7 | 1993-03-03 | ||
| GB939304273A GB9304273D0 (en) | 1993-03-03 | 1993-03-03 | Carbohydrate derived surfactants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2095879A1 true CA2095879A1 (en) | 1993-11-12 |
Family
ID=27266175
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002095879A Abandoned CA2095879A1 (en) | 1992-05-11 | 1993-05-10 | Carbohydrate derived surfactants and their precursors |
Country Status (22)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2713638A1 (fr) * | 1993-12-14 | 1995-06-16 | Vegatec Sarl | Nouveaux tensioactifs glycosidiques et zwitterioniques, leurs procédés de synthèse et leurs études physico-chimiques. |
| BR9708718A (pt) * | 1996-04-18 | 1999-08-03 | Procter & Gamble | Sínteses de aminas substituídas |
| US6281176B1 (en) | 1999-12-03 | 2001-08-28 | Albemarle Corporation | Process for producing betaine/amine oxide mixtures |
| US20060100127A1 (en) * | 2004-11-11 | 2006-05-11 | Meier Ingrid K | N,N-dialkylpolyhydroxyalkylamines |
| CN100496692C (zh) * | 2007-06-21 | 2009-06-10 | 北京服装学院 | 糖基季胺盐型阳离子表面活性剂、制法及应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2016962A (en) * | 1932-09-27 | 1935-10-08 | Du Pont | Process for producing glucamines and related products |
| US2016963A (en) * | 1932-09-27 | 1935-10-08 | Du Pont | Product comprising glucamines and related substances |
| US2016956A (en) * | 1932-11-04 | 1935-10-08 | Du Pont | Amino derivatives and process of preparing them |
| US2060851A (en) * | 1935-09-13 | 1936-11-17 | Du Pont | Chemical compounds |
| BE425071A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1936-12-14 | |||
| DE2063423A1 (en) * | 1970-12-23 | 1972-09-21 | Rewo Chemische Fabrik GmbH, 6497 Stemau | Betaine - contg surfactant mixtures - prepd from tert amines and halocarboxylic or halosulphonic acids or sultones |
| DE3915121A1 (de) * | 1989-05-09 | 1990-11-15 | Huels Chemische Werke Ag | Neue n-alkylglykaminoverbindungen sowie ein verfahren zur herstellung und ihre verwendung |
| US5099065A (en) * | 1990-02-27 | 1992-03-24 | Kao Corporation | Betaine compound and detergent composition |
-
1993
- 1993-05-10 ES ES93107555T patent/ES2102549T3/es not_active Expired - Lifetime
- 1993-05-10 AT AT93107555T patent/ATE151069T1/de not_active IP Right Cessation
- 1993-05-10 IN IN464DE1993 patent/IN186296B/en unknown
- 1993-05-10 DK DK93107555.0T patent/DK0569904T3/da active
- 1993-05-10 DE DE69309341T patent/DE69309341T2/de not_active Expired - Fee Related
- 1993-05-10 HU HU9301355A patent/HU219982B/hu not_active IP Right Cessation
- 1993-05-10 MX MX9302729A patent/MX9302729A/es not_active IP Right Cessation
- 1993-05-10 EP EP93107555A patent/EP0569904B1/en not_active Expired - Lifetime
- 1993-05-10 CA CA002095879A patent/CA2095879A1/en not_active Abandoned
- 1993-05-11 CN CN93107067A patent/CN1086739A/zh active Pending
- 1993-05-11 SK SK455-93A patent/SK45593A3/sk unknown
- 1993-05-11 PL PL93298895A patent/PL172930B1/pl unknown
- 1993-05-11 PH PH46170A patent/PH30986A/en unknown
- 1993-05-11 NO NO93931716A patent/NO931716L/no unknown
- 1993-05-11 JP JP10950893A patent/JP3347393B2/ja not_active Expired - Fee Related
- 1993-05-11 NZ NZ247601A patent/NZ247601A/en not_active IP Right Cessation
- 1993-05-11 CZ CZ93857A patent/CZ85793A3/cs unknown
- 1993-05-11 GB GB9309668A patent/GB2266889B/en not_active Expired - Fee Related
- 1993-05-11 AU AU38524/93A patent/AU657219B2/en not_active Ceased
- 1993-05-11 MY MYPI93000866A patent/MY109032A/en unknown
-
1994
- 1994-11-16 US US08/340,801 patent/US5523478A/en not_active Expired - Fee Related
-
1996
- 1996-07-12 US US08/679,152 patent/US5710332A/en not_active Expired - Fee Related
-
1997
- 1997-04-22 GR GR970400926T patent/GR3023261T3/el unknown
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