NL1004153C2 - Nieuwe fructaan-derivaten. - Google Patents
Nieuwe fructaan-derivaten. Download PDFInfo
- Publication number
- NL1004153C2 NL1004153C2 NL1004153A NL1004153A NL1004153C2 NL 1004153 C2 NL1004153 C2 NL 1004153C2 NL 1004153 A NL1004153 A NL 1004153A NL 1004153 A NL1004153 A NL 1004153A NL 1004153 C2 NL1004153 C2 NL 1004153C2
- Authority
- NL
- Netherlands
- Prior art keywords
- fructan
- group
- cationic
- derivatives
- derivative according
- Prior art date
Links
- 229920002670 Fructan Polymers 0.000 title claims abstract description 48
- -1 methyl carboxymethyl Chemical group 0.000 claims abstract description 40
- 125000002091 cationic group Chemical group 0.000 claims abstract description 37
- 229920001202 Inulin Polymers 0.000 claims abstract description 16
- JYJIGFIDKWBXDU-MNNPPOADSA-N inulin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@]1(OC[C@]2(OC[C@]3(OC[C@]4(OC[C@]5(OC[C@]6(OC[C@]7(OC[C@]8(OC[C@]9(OC[C@]%10(OC[C@]%11(OC[C@]%12(OC[C@]%13(OC[C@]%14(OC[C@]%15(OC[C@]%16(OC[C@]%17(OC[C@]%18(OC[C@]%19(OC[C@]%20(OC[C@]%21(OC[C@]%22(OC[C@]%23(OC[C@]%24(OC[C@]%25(OC[C@]%26(OC[C@]%27(OC[C@]%28(OC[C@]%29(OC[C@]%30(OC[C@]%31(OC[C@]%32(OC[C@]%33(OC[C@]%34(OC[C@]%35(OC[C@]%36(O[C@@H]%37[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O%37)O)[C@H]([C@H](O)[C@@H](CO)O%36)O)[C@H]([C@H](O)[C@@H](CO)O%35)O)[C@H]([C@H](O)[C@@H](CO)O%34)O)[C@H]([C@H](O)[C@@H](CO)O%33)O)[C@H]([C@H](O)[C@@H](CO)O%32)O)[C@H]([C@H](O)[C@@H](CO)O%31)O)[C@H]([C@H](O)[C@@H](CO)O%30)O)[C@H]([C@H](O)[C@@H](CO)O%29)O)[C@H]([C@H](O)[C@@H](CO)O%28)O)[C@H]([C@H](O)[C@@H](CO)O%27)O)[C@H]([C@H](O)[C@@H](CO)O%26)O)[C@H]([C@H](O)[C@@H](CO)O%25)O)[C@H]([C@H](O)[C@@H](CO)O%24)O)[C@H]([C@H](O)[C@@H](CO)O%23)O)[C@H]([C@H](O)[C@@H](CO)O%22)O)[C@H]([C@H](O)[C@@H](CO)O%21)O)[C@H]([C@H](O)[C@@H](CO)O%20)O)[C@H]([C@H](O)[C@@H](CO)O%19)O)[C@H]([C@H](O)[C@@H](CO)O%18)O)[C@H]([C@H](O)[C@@H](CO)O%17)O)[C@H]([C@H](O)[C@@H](CO)O%16)O)[C@H]([C@H](O)[C@@H](CO)O%15)O)[C@H]([C@H](O)[C@@H](CO)O%14)O)[C@H]([C@H](O)[C@@H](CO)O%13)O)[C@H]([C@H](O)[C@@H](CO)O%12)O)[C@H]([C@H](O)[C@@H](CO)O%11)O)[C@H]([C@H](O)[C@@H](CO)O%10)O)[C@H]([C@H](O)[C@@H](CO)O9)O)[C@H]([C@H](O)[C@@H](CO)O8)O)[C@H]([C@H](O)[C@@H](CO)O7)O)[C@H]([C@H](O)[C@@H](CO)O6)O)[C@H]([C@H](O)[C@@H](CO)O5)O)[C@H]([C@H](O)[C@@H](CO)O4)O)[C@H]([C@H](O)[C@@H](CO)O3)O)[C@H]([C@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 JYJIGFIDKWBXDU-MNNPPOADSA-N 0.000 claims abstract description 16
- 229940029339 inulin Drugs 0.000 claims abstract description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 6
- 230000008569 process Effects 0.000 claims abstract description 6
- 125000003277 amino group Chemical group 0.000 claims abstract description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 claims abstract description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract 6
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract 2
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 2
- 125000005277 alkyl imino group Chemical group 0.000 claims abstract 2
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 150000002772 monosaccharides Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- LTVDFSLWFKLJDQ-UHFFFAOYSA-N α-tocopherolquinone Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)(O)CCC1=C(C)C(=O)C(C)=C(C)C1=O LTVDFSLWFKLJDQ-UHFFFAOYSA-N 0.000 claims description 5
- 239000003112 inhibitor Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 229910052794 bromium Chemical group 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000005260 corrosion Methods 0.000 claims description 2
- 230000007797 corrosion Effects 0.000 claims description 2
- 239000000645 desinfectant Substances 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 3
- NARVIWMVBMUEOG-UHFFFAOYSA-N 2-Hydroxy-propylene Chemical group CC(O)=C NARVIWMVBMUEOG-UHFFFAOYSA-N 0.000 claims 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 2
- 150000002118 epoxides Chemical class 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 239000000853 adhesive Substances 0.000 claims 1
- 230000001070 adhesive effect Effects 0.000 claims 1
- 239000012670 alkaline solution Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000002537 cosmetic Substances 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 abstract description 5
- 125000001424 substituent group Chemical group 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- ZFTFOHBYVDOAMH-XNOIKFDKSA-N (2r,3s,4s,5r)-5-[[(2r,3s,4s,5r)-5-[[(2r,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-2-(hydroxymethyl)oxolan-2-yl]oxymethyl]-2-(hydroxymethyl)oxolane-2,3,4-triol Chemical class O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@@H]1[C@@H](O)[C@H](O)[C@](CO)(OC[C@@H]2[C@H]([C@H](O)[C@@](O)(CO)O2)O)O1 ZFTFOHBYVDOAMH-XNOIKFDKSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 9
- 238000006467 substitution reaction Methods 0.000 description 9
- 229920002472 Starch Polymers 0.000 description 7
- 235000019698 starch Nutrition 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000008186 active pharmaceutical agent Substances 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000008107 starch Substances 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 229920001282 polysaccharide Polymers 0.000 description 5
- 239000005017 polysaccharide Substances 0.000 description 5
- 241000723343 Cichorium Species 0.000 description 4
- 235000007542 Cichorium intybus Nutrition 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000001728 nano-filtration Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229920000881 Modified starch Polymers 0.000 description 3
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 235000019426 modified starch Nutrition 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical class C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- 229940106681 chloroacetic acid Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000005553 drilling Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 description 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 1
- JPFYIYQIGQYIMC-UHFFFAOYSA-N 1,4-bis(2-chloroethyl)piperazine Chemical compound ClCCN1CCN(CCCl)CC1 JPFYIYQIGQYIMC-UHFFFAOYSA-N 0.000 description 1
- OZDGMOYKSFPLSE-UHFFFAOYSA-N 2-Methylaziridine Chemical compound CC1CN1 OZDGMOYKSFPLSE-UHFFFAOYSA-N 0.000 description 1
- WJAXXWSZNSFVNG-UHFFFAOYSA-N 2-bromoethanamine;hydron;bromide Chemical compound [Br-].[NH3+]CCBr WJAXXWSZNSFVNG-UHFFFAOYSA-N 0.000 description 1
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 1
- GYXWNSDLDXGMGU-UHFFFAOYSA-N 2-chloro-n,n-dimethylpropan-1-amine Chemical compound CC(Cl)CN(C)C GYXWNSDLDXGMGU-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- NNZGNZHUGJAKKT-UHFFFAOYSA-M 3-bromopropyl(trimethyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCBr NNZGNZHUGJAKKT-UHFFFAOYSA-M 0.000 description 1
- ZAPMTSHEXFEPSD-UHFFFAOYSA-N 4-(2-chloroethyl)morpholine Chemical compound ClCCN1CCOCC1 ZAPMTSHEXFEPSD-UHFFFAOYSA-N 0.000 description 1
- MYGXGCCFTPKWIH-UHFFFAOYSA-N 4-chloro-1-methylpiperidine Chemical compound CN1CCC(Cl)CC1 MYGXGCCFTPKWIH-UHFFFAOYSA-N 0.000 description 1
- DYUZZXXUVYQTQX-UHFFFAOYSA-N 4-chlorobut-2-en-1-amine Chemical class NCC=CCCl DYUZZXXUVYQTQX-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical group OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 244000115658 Dahlia pinnata Species 0.000 description 1
- 235000012040 Dahlia pinnata Nutrition 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 240000008892 Helianthus tuberosus Species 0.000 description 1
- 235000003230 Helianthus tuberosus Nutrition 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910001919 chlorite Inorganic materials 0.000 description 1
- 229910052619 chlorite group Inorganic materials 0.000 description 1
- XIVLWOXCLOIZSW-UHFFFAOYSA-M chloromethyl-(2-hydroxypropyl)-dimethylazanium;chloride Chemical compound [Cl-].CC(O)C[N+](C)(C)CCl XIVLWOXCLOIZSW-UHFFFAOYSA-M 0.000 description 1
- QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000000909 electrodialysis Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000002979 fabric softener Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- BJHIKXHVCXFQLS-UYFOZJQFSA-N fructose group Chemical group OCC(=O)[C@@H](O)[C@H](O)[C@H](O)CO BJHIKXHVCXFQLS-UYFOZJQFSA-N 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000000879 imine group Chemical group 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical group O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000005374 membrane filtration Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000005555 metalworking Methods 0.000 description 1
- 239000010813 municipal solid waste Substances 0.000 description 1
- MPAMXJNEIAPUEL-UHFFFAOYSA-N n-ethenyl-n-methylethenamine Chemical group C=CN(C)C=C MPAMXJNEIAPUEL-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- 229960003330 pentetic acid Drugs 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0051—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Fructofuranans, e.g. beta-2,6-D-fructofuranan, i.e. levan; Derivatives thereof
- C08B37/0054—Inulin, i.e. beta-2,1-D-fructofuranan; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0051—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Fructofuranans, e.g. beta-2,6-D-fructofuranan, i.e. levan; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Organic Chemistry (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Moulding By Coating Moulds (AREA)
- Reinforced Plastic Materials (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL1004153A NL1004153C2 (nl) | 1996-09-30 | 1996-09-30 | Nieuwe fructaan-derivaten. |
| NZ334805A NZ334805A (en) | 1996-09-30 | 1997-09-30 | Fructan derivatives |
| US09/269,028 US20020082399A1 (en) | 1996-09-30 | 1997-09-30 | Fructan derivatives |
| PCT/NL1997/000543 WO1998014482A1 (en) | 1996-09-30 | 1997-09-30 | Fructan derivatives |
| PT97942300T PT918800E (pt) | 1996-09-30 | 1997-09-30 | Derivados de fructano |
| JP51639698A JP4181221B2 (ja) | 1996-09-30 | 1997-09-30 | フルクタン誘導体 |
| DK97942300T DK0918800T3 (da) | 1996-09-30 | 1997-09-30 | Fructanderivater |
| DE69709873T DE69709873T2 (de) | 1996-09-30 | 1997-09-30 | Fruktanderivate |
| AU44025/97A AU719739B2 (en) | 1996-09-30 | 1997-09-30 | Fructan derivatives |
| ES97942300T ES2169424T3 (es) | 1996-09-30 | 1997-09-30 | Derivados de fructano. |
| EP97942300A EP0918800B1 (de) | 1996-09-30 | 1997-09-30 | Fruktanderivate |
| CA002269540A CA2269540C (en) | 1996-09-30 | 1997-09-30 | Fructan derivatives |
| AT97942300T ATE211490T1 (de) | 1996-09-30 | 1997-09-30 | Fruktanderivate |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL1004153 | 1996-09-30 | ||
| NL1004153A NL1004153C2 (nl) | 1996-09-30 | 1996-09-30 | Nieuwe fructaan-derivaten. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL1004153C2 true NL1004153C2 (nl) | 1998-03-31 |
Family
ID=19763589
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL1004153A NL1004153C2 (nl) | 1996-09-30 | 1996-09-30 | Nieuwe fructaan-derivaten. |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20020082399A1 (de) |
| EP (1) | EP0918800B1 (de) |
| JP (1) | JP4181221B2 (de) |
| AT (1) | ATE211490T1 (de) |
| AU (1) | AU719739B2 (de) |
| CA (1) | CA2269540C (de) |
| DE (1) | DE69709873T2 (de) |
| DK (1) | DK0918800T3 (de) |
| ES (1) | ES2169424T3 (de) |
| NL (1) | NL1004153C2 (de) |
| NZ (1) | NZ334805A (de) |
| PT (1) | PT918800E (de) |
| WO (1) | WO1998014482A1 (de) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2795954B1 (fr) * | 1999-07-09 | 2001-09-07 | Oreal | Composition cosmetique comprenant au moins un fructane cationique et au moins un polymere coiffant |
| FR2795953A1 (fr) * | 1999-07-09 | 2001-01-12 | Oreal | Compositions cosmetiques contenant un fructane cationique et un agent conditionneur et leurs utilisations |
| FR2795951B1 (fr) * | 1999-07-09 | 2001-09-07 | Oreal | Compositions cosmetiques contenant un fructane cationique et un agent protecteur des matieres keratiniques et leurs utilisations |
| EP1174118A1 (de) * | 2000-06-28 | 2002-01-23 | Cognis France S.A. | Verwendung von Inulinen und Inulinderivaten |
| FR2819403B1 (fr) | 2001-01-12 | 2004-10-15 | Oreal | Compositions cosmetiques contenant un fructane, un polysaccharide et un agent benefique et leurs utilisations |
| FR2819404B1 (fr) | 2001-01-12 | 2004-11-05 | Oreal | Compositions cosmetiques contenant un fructane et un polymere cationique et leurs utilisations |
| ES2379799T3 (es) * | 2004-08-31 | 2012-05-03 | Hercules Incorporated | Procedimiento para preparar poligalactomanano catiónico de bajo peso molecular con olor reducido |
| WO2006055877A2 (en) * | 2004-11-19 | 2006-05-26 | Rhodia Inc. | Derivatized polysaccharide polymer |
| FR2935266A1 (fr) * | 2008-08-27 | 2010-03-05 | Oreal | Utilisation d'un liquide ionique a base de sucre dans le domaine capillaire. |
| US9012376B2 (en) * | 2011-03-14 | 2015-04-21 | Halliburton Energy Services, Inc. | Inulin as corrosion inhibitor |
| US20140302101A1 (en) * | 2013-04-05 | 2014-10-09 | John Carson | Natural hairstyle holding product containing levan as a film-former |
| FR3010308B1 (fr) | 2013-09-12 | 2016-11-25 | Oreal | Procede de traitement des fibres keratiniques avec un compose d'acide pyridine dicarboxylique |
| ES2919555T3 (es) * | 2016-09-12 | 2022-07-27 | Oreal | Procedimiento de tratamiento de las materias queratínicas a partir de polisacárido aminado y oxidado |
| EP3315593B1 (de) * | 2016-10-31 | 2020-01-01 | Coöperatie Koninklijke Cosun U.A. | Waschmittelzusammensetzung mit einem kationischen derivat eines polysaccharids |
| PL3536384T3 (pl) * | 2018-03-06 | 2023-06-12 | Coöperatie Koninklijke Cosun U.A. | Kompozycja kosmetyczna zawierająca kationową inulina i anionowy środek powierzchniowo czynny |
| EP3829305A1 (de) | 2018-07-31 | 2021-06-09 | Bayer Aktiengesellschaft | Verwendung einer kationischen polysaccharidverbindung als ein fungizid, pestizid, algizid, trocknungsmittel und zur verlängerung der haltbarkeit von obst und gemüse |
| EP4227392B1 (de) * | 2022-02-11 | 2024-04-03 | The Procter & Gamble Company | Flüssige handspülmittelzusammensetzung |
| WO2023227708A1 (en) | 2022-05-25 | 2023-11-30 | Bayer Aktiengesellschaft | Biobased larvicides |
| CN117285913A (zh) * | 2022-06-20 | 2023-12-26 | 中国石油化工股份有限公司 | 一种强吸附型粘土稳定剂的制备方法 |
| WO2024018077A1 (en) | 2022-07-22 | 2024-01-25 | Coöperatie Koninklijke Cosun U.A. | Cationic inulin |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0556688A1 (de) * | 1992-02-21 | 1993-08-25 | Wolff Walsrode Aktiengesellschaft | Verfahren zur Herstellung von Ammoniumgruppen enthaltenden Polymeren |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU5410196A (en) * | 1995-04-27 | 1996-11-18 | Cooperatie Suiker Unie U.A. | Inulin derivatives |
-
1996
- 1996-09-30 NL NL1004153A patent/NL1004153C2/nl not_active IP Right Cessation
-
1997
- 1997-09-30 CA CA002269540A patent/CA2269540C/en not_active Expired - Lifetime
- 1997-09-30 ES ES97942300T patent/ES2169424T3/es not_active Expired - Lifetime
- 1997-09-30 US US09/269,028 patent/US20020082399A1/en not_active Abandoned
- 1997-09-30 AU AU44025/97A patent/AU719739B2/en not_active Expired
- 1997-09-30 DK DK97942300T patent/DK0918800T3/da active
- 1997-09-30 DE DE69709873T patent/DE69709873T2/de not_active Expired - Lifetime
- 1997-09-30 NZ NZ334805A patent/NZ334805A/en not_active IP Right Cessation
- 1997-09-30 EP EP97942300A patent/EP0918800B1/de not_active Expired - Lifetime
- 1997-09-30 JP JP51639698A patent/JP4181221B2/ja not_active Expired - Lifetime
- 1997-09-30 PT PT97942300T patent/PT918800E/pt unknown
- 1997-09-30 AT AT97942300T patent/ATE211490T1/de not_active IP Right Cessation
- 1997-09-30 WO PCT/NL1997/000543 patent/WO1998014482A1/en not_active Ceased
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0556688A1 (de) * | 1992-02-21 | 1993-08-25 | Wolff Walsrode Aktiengesellschaft | Verfahren zur Herstellung von Ammoniumgruppen enthaltenden Polymeren |
Non-Patent Citations (1)
| Title |
|---|
| M.E. CARR: "Preparation of cartionic starch containing quaternary ammonium substituents by reactive twin-screw extrusion processing", JOURNAL OF APPLIED POLYMER SCIENCE, vol. 54, 1994, USA, pages 1855 - 1861, XP000512037 * |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE211490T1 (de) | 2002-01-15 |
| DE69709873T2 (de) | 2002-08-22 |
| CA2269540C (en) | 2006-09-19 |
| JP4181221B2 (ja) | 2008-11-12 |
| WO1998014482A1 (en) | 1998-04-09 |
| DK0918800T3 (da) | 2002-03-25 |
| NZ334805A (en) | 2001-04-27 |
| DE69709873D1 (de) | 2002-02-28 |
| JP2001505594A (ja) | 2001-04-24 |
| AU719739B2 (en) | 2000-05-18 |
| EP0918800B1 (de) | 2002-01-02 |
| PT918800E (pt) | 2002-05-31 |
| EP0918800A1 (de) | 1999-06-02 |
| US20020082399A1 (en) | 2002-06-27 |
| CA2269540A1 (en) | 1998-04-09 |
| AU4402597A (en) | 1998-04-24 |
| ES2169424T3 (es) | 2002-07-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PD2B | A search report has been drawn up | ||
| MK | Patent expired because of reaching the maximum lifetime of a patent |
Effective date: 20160929 |