ZA200201296B - Zwitterionic polyamines and a process for their production. - Google Patents
Zwitterionic polyamines and a process for their production. Download PDFInfo
- Publication number
- ZA200201296B ZA200201296B ZA200201296A ZA200201296A ZA200201296B ZA 200201296 B ZA200201296 B ZA 200201296B ZA 200201296 A ZA200201296 A ZA 200201296A ZA 200201296 A ZA200201296 A ZA 200201296A ZA 200201296 B ZA200201296 B ZA 200201296B
- Authority
- ZA
- South Africa
- Prior art keywords
- polyamine
- group
- formula
- zwitterionic
- chy
- Prior art date
Links
- 229920000768 polyamine Polymers 0.000 title claims abstract description 102
- 238000000034 method Methods 0.000 title claims abstract description 20
- 230000008569 process Effects 0.000 title claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 13
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 22
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 22
- 125000006850 spacer group Chemical group 0.000 claims abstract description 17
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 8
- 150000001340 alkali metals Chemical group 0.000 claims abstract description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 5
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- 239000007795 chemical reaction product Substances 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 238000005956 quaternization reaction Methods 0.000 claims description 10
- MRNZSTMRDWRNNR-UHFFFAOYSA-N bis(hexamethylene)triamine Chemical compound NCCCCCCNCCCCCCN MRNZSTMRDWRNNR-UHFFFAOYSA-N 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 8
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- 150000003512 tertiary amines Chemical group 0.000 claims description 6
- -1 hydroxypropyl group Chemical group 0.000 claims description 5
- XUSNPFGLKGCWGN-UHFFFAOYSA-N 3-[4-(3-aminopropyl)piperazin-1-yl]propan-1-amine Chemical compound NCCCN1CCN(CCCN)CC1 XUSNPFGLKGCWGN-UHFFFAOYSA-N 0.000 claims description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 4
- WOVJRSMTQMZAJS-UHFFFAOYSA-N n,n'-bis(3-aminopropyl)hexane-1,6-diamine Chemical compound NCCCNCCCCCCNCCCN WOVJRSMTQMZAJS-UHFFFAOYSA-N 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 claims description 2
- SMOXLGSFWOUPHC-UHFFFAOYSA-N C(=C)P(O)(O)O Chemical compound C(=C)P(O)(O)O SMOXLGSFWOUPHC-UHFFFAOYSA-N 0.000 claims description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- 229940050176 methyl chloride Drugs 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 claims description 2
- PAOXFRSJRCGJLV-UHFFFAOYSA-N 2-[4-(2-aminoethyl)piperazin-1-yl]ethanamine Chemical compound NCCN1CCN(CCN)CC1 PAOXFRSJRCGJLV-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- 229940116254 phosphonic acid Drugs 0.000 claims 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 125000000129 anionic group Chemical group 0.000 abstract description 14
- 239000003599 detergent Substances 0.000 abstract description 4
- 125000001302 tertiary amino group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 102100025991 Betaine-homocysteine S-methyltransferase 1 Human genes 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 101000933413 Homo sapiens Betaine-homocysteine S-methyltransferase 1 Proteins 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229960005419 nitrogen Drugs 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 5
- 239000004927 clay Substances 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
- 229940073608 benzyl chloride Drugs 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 238000007046 ethoxylation reaction Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- PFNFFQXMRSDOHW-UHFFFAOYSA-N spermine Chemical compound NCCCNCCCCNCCCN PFNFFQXMRSDOHW-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000019635 sulfation Effects 0.000 description 2
- 238000005670 sulfation reaction Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical class NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- MLRVZFYXUZQSRU-UHFFFAOYSA-N 1-chlorohexane Chemical compound CCCCCCCl MLRVZFYXUZQSRU-UHFFFAOYSA-N 0.000 description 1
- CQWCZJWYHPCXRK-UHFFFAOYSA-N 1-n,2-n-bis(2-aminoethyl)propane-1,2-diamine Chemical compound NCCNC(C)CNCCN CQWCZJWYHPCXRK-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- ZJINVUVGTWOUJI-UHFFFAOYSA-N 2-n-(2-aminoethyl)propane-1,2-diamine Chemical compound NCC(C)NCCN ZJINVUVGTWOUJI-UHFFFAOYSA-N 0.000 description 1
- ZAXCZCOUDLENMH-UHFFFAOYSA-N 3,3,3-tetramine Chemical compound NCCCNCCCNCCCN ZAXCZCOUDLENMH-UHFFFAOYSA-N 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- UVLSCMIEPPWCHZ-UHFFFAOYSA-N 3-piperazin-1-ylpropan-1-amine Chemical compound NCCCN1CCNCC1 UVLSCMIEPPWCHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- VRPPEXGZBZBARW-UHFFFAOYSA-N N-(2-aminoethyl)butane-1,4-diamine Chemical compound NCCCCNCCN VRPPEXGZBZBARW-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- PZDZPPFYJBZKJD-UHFFFAOYSA-N [4-(aminomethylidene)cyclohexa-2,5-dien-1-ylidene]methanamine Chemical compound NC=C1C=CC(=CN)C=C1 PZDZPPFYJBZKJD-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000013011 aqueous formulation Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical class OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical group C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- QSINQXYQYVRZKG-UHFFFAOYSA-N n'-(2-aminoethyl)hexane-1,6-diamine Chemical compound NCCCCCCNCCN QSINQXYQYVRZKG-UHFFFAOYSA-N 0.000 description 1
- KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 description 1
- INAQHJUDGSEXDR-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-octylpropane-1,3-diamine Chemical compound CCCCCCCCN(CCCN)CCCN INAQHJUDGSEXDR-UHFFFAOYSA-N 0.000 description 1
- DYUCNAMTUNGLAB-UHFFFAOYSA-N n,n'-bis(2-aminoethyl)hexane-1,6-diamine Chemical compound NCCNCCCCCCNCCN DYUCNAMTUNGLAB-UHFFFAOYSA-N 0.000 description 1
- UQUPIHHYKUEXQD-UHFFFAOYSA-N n,n′-dimethyl-1,3-propanediamine Chemical compound CNCCCNC UQUPIHHYKUEXQD-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3796—Amphoteric polymers or zwitterionic polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0206—Polyalkylene(poly)amines
- C08G73/0213—Preparatory process
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0206—Polyalkylene(poly)amines
- C08G73/0213—Preparatory process
- C08G73/0226—Quaternisation of polyalkylene(poly)amines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0273—Polyamines containing heterocyclic moieties in the main chain
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3723—Polyamines or polyalkyleneimines
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14416599P | 1999-07-16 | 1999-07-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200201296B true ZA200201296B (en) | 2003-04-30 |
Family
ID=22507378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200201296A ZA200201296B (en) | 1999-07-16 | 2002-02-15 | Zwitterionic polyamines and a process for their production. |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP1198492B1 (es) |
| JP (1) | JP5174305B2 (es) |
| KR (1) | KR100675579B1 (es) |
| CN (1) | CN1158335C (es) |
| AT (1) | ATE251652T1 (es) |
| AU (1) | AU771572B2 (es) |
| BR (1) | BR0012490B1 (es) |
| CA (1) | CA2379036A1 (es) |
| DE (1) | DE60005839T2 (es) |
| ES (1) | ES2208388T3 (es) |
| MX (1) | MXPA02000446A (es) |
| WO (1) | WO2001005874A1 (es) |
| ZA (1) | ZA200201296B (es) |
Families Citing this family (66)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE407192T1 (de) * | 2000-02-23 | 2008-09-15 | Procter & Gamble | Waschmittelgranulate enthaltend zwitterionische polyamine |
| CN1237162C (zh) * | 2000-02-23 | 2006-01-18 | 宝洁公司 | 具有增强泥土清除益处的液体衣用洗涤剂组合物 |
| WO2004020563A1 (en) * | 2002-08-30 | 2004-03-11 | The Procter & Gamble Company | Detergent compositions comprising hydrophobically modified polyamines |
| DE10356341A1 (de) * | 2003-11-28 | 2005-06-23 | Bayer Chemicals Ag | Alkoxylierte Polyalkylenimine mit anionischen Gruppen und ihre Verwendung |
| EP1732972A1 (en) | 2004-03-19 | 2006-12-20 | The Procter and Gamble Company | Process of sulfating select polymers |
| DE602005015532D1 (de) * | 2004-11-22 | 2009-09-03 | Procter & Gamble | Wasserlöslicher Beutel gefüllt mit einer Flüssigkeit |
| JP2008523225A (ja) | 2004-12-17 | 2008-07-03 | ザ プロクター アンド ギャンブル カンパニー | 改良された疎水性汚れ洗浄のための疎水変性ポリオール |
| EP1838825A1 (en) | 2004-12-17 | 2007-10-03 | The Procter and Gamble Company | Hydrophilically modified polyols for improved hydrophobic soil cleaning |
| EP3101110B1 (en) | 2006-01-23 | 2023-08-30 | The Procter & Gamble Company | Enzyme and fabric hueing agent containing compositions |
| JP2009523901A (ja) | 2006-01-23 | 2009-06-25 | ザ プロクター アンド ギャンブル カンパニー | 洗剤組成物 |
| BRPI0709024B1 (pt) | 2006-03-22 | 2017-02-14 | Procter & Gamble | composição líquida perolizada para tratamento e método para tratamento de um substrato |
| US7629158B2 (en) | 2006-06-16 | 2009-12-08 | The Procter & Gamble Company | Cleaning and/or treatment compositions |
| US8021436B2 (en) | 2007-09-27 | 2011-09-20 | The Procter & Gamble Company | Cleaning and/or treatment compositions comprising a xyloglucan conjugate |
| US9376648B2 (en) | 2008-04-07 | 2016-06-28 | The Procter & Gamble Company | Foam manipulation compositions containing fine particles |
| US8853457B2 (en) | 2010-01-04 | 2014-10-07 | Rhodia Operations | Polyamine and method for producing thereof |
| US8940284B2 (en) | 2010-04-01 | 2015-01-27 | The Procter & Gamble Company | Organosilicones |
| WO2011143321A1 (en) | 2010-05-12 | 2011-11-17 | The Procter & Gamble Company | Care polymers |
| WO2011163457A1 (en) | 2010-06-23 | 2011-12-29 | The Procter & Gamble Company | Product for pre-treatment and laundering of stained fabric |
| US8846596B2 (en) | 2011-02-16 | 2014-09-30 | The Procter & Gamble Company | Liquid cleaning compositions |
| US20120324655A1 (en) | 2011-06-23 | 2012-12-27 | Nalini Chawla | Product for pre-treatment and laundering of stained fabric |
| EP2875110B1 (en) | 2012-07-19 | 2016-08-17 | The Procter & Gamble Company | Cleaning compositions |
| JP6122114B2 (ja) | 2012-07-27 | 2017-04-26 | ザ プロクター アンド ギャンブル カンパニー | ポリシロキサンコポリマー |
| CA2888341A1 (en) | 2012-10-24 | 2014-05-01 | The Procter & Gamble Company | Anti foam compositions comprising aryl bearing polyorganosilicons |
| CA2888342A1 (en) | 2012-10-24 | 2014-05-01 | The Procter & Gamble Company | Anti foam compositions comprising partly phenyl bearing polyorganosilicons |
| BR112015028824A2 (pt) | 2013-05-24 | 2017-07-25 | Procter & Gamble | composição de tensoativo concentrada |
| BR112015028853A2 (pt) | 2013-05-24 | 2017-08-29 | Procter & Gamble | Composição detergente com ph baixo |
| WO2014190133A1 (en) | 2013-05-24 | 2014-11-27 | The Procter & Gamble Company | Low ph detergent composition comprising nonionic surfactants |
| JP6342508B2 (ja) | 2014-02-26 | 2018-06-13 | ザ プロクター アンド ギャンブル カンパニー | 消泡剤組成物 |
| US9574161B2 (en) | 2014-04-29 | 2017-02-21 | The Procter & Gamble Company | Fabric care compositions comprising polyurethane, polyurea and/or polyurethaneurea polymers |
| EP3152288A1 (en) | 2014-06-06 | 2017-04-12 | The Procter & Gamble Company | Detergent composition comprising polyalkyleneimine polymers |
| EP3186350B1 (en) | 2014-08-27 | 2019-10-09 | The Procter and Gamble Company | Detergent composition comprising a cationic polymer |
| US9771546B2 (en) | 2014-08-27 | 2017-09-26 | The Procter & Gamble Company | Detergent composition comprising a cationic copolymer containing (meth)acrylamide and diallyl dimethyl ammonium chloride |
| US9951297B2 (en) | 2014-08-27 | 2018-04-24 | The Procter & Gamble Company | Detergent composition compromising a cationic polymer containing a vinyl formamide nonionic structural unit |
| JP6400837B2 (ja) | 2014-08-27 | 2018-10-03 | ザ プロクター アンド ギャンブル カンパニー | 布地の処理方法 |
| EP3191570B1 (en) | 2014-09-08 | 2019-05-15 | The Procter and Gamble Company | Detergent compositions containing a branched surfactant |
| ES2939553T3 (es) | 2014-09-08 | 2023-04-24 | Procter & Gamble | Composiciones detergentes que contienen un tensioactivo ramificado |
| US10280237B2 (en) * | 2014-09-15 | 2019-05-07 | Basf Se | Salts of etheramines and polymeric acid |
| US9850452B2 (en) | 2014-09-25 | 2017-12-26 | The Procter & Gamble Company | Fabric care compositions containing a polyetheramine |
| US9506019B2 (en) | 2015-01-28 | 2016-11-29 | The Procter & Gamble Company | Silicone nanoemulsion comprising alkylene glycol alkyl ether |
| US9994800B2 (en) | 2015-03-26 | 2018-06-12 | The Procter & Gamble Company | Fabric care compositions comprising organosiloxane polymers with an amine-containing end cap |
| US10053651B2 (en) | 2015-05-22 | 2018-08-21 | The Procter & Gamble Company | Method of making surfactant compositions and detergent compositions |
| US10059909B2 (en) | 2015-05-22 | 2018-08-28 | The Procter & Gamble Company | Surfactant and detergent compositions containing ethoxylated glycerine |
| EP3307129A1 (en) | 2015-06-11 | 2018-04-18 | The Procter and Gamble Company | Device and methods for applying compositions to surfaces |
| EP3411425A1 (en) | 2016-02-02 | 2018-12-12 | The Procter and Gamble Company | Antifoam molecules and compositions |
| US9896648B2 (en) | 2016-03-02 | 2018-02-20 | The Procter & Gamble Company | Ethoxylated diols and compositions containing ethoxylated diols |
| US9856440B2 (en) | 2016-03-02 | 2018-01-02 | The Procter & Gamble Company | Compositions containing anionic surfactant and a solvent comprising butanediol |
| US9840684B2 (en) | 2016-03-02 | 2017-12-12 | The Procter & Gamble Company | Compositions containing alkyl sulfates and/or alkoxylated alkyl sulfates and a solvent comprising a diol |
| US9790454B2 (en) | 2016-03-02 | 2017-10-17 | The Procter & Gamble Company | Compositions containing alkyl sulfates and/or alkoxylated alkyl sulfates and a solvent comprising a diol |
| CA3018136A1 (en) | 2016-04-08 | 2017-10-12 | Basf Se | Copolymers comprising polyalkylene oxide groups and quaternary nitrogen atoms |
| US20180201875A1 (en) | 2017-01-13 | 2018-07-19 | The Procter & Gamble Company | Compositions comprising branched sulfonated surfactants |
| US20180216029A1 (en) | 2017-01-27 | 2018-08-02 | The Procter & Gamble Company | Concentrated surfactant composition |
| US20180216031A1 (en) | 2017-01-27 | 2018-08-02 | The Procter & Gamble Company | Concentrated surfactant composition |
| US20180216030A1 (en) | 2017-01-27 | 2018-08-02 | The Procter & Gamble Company | Concentrated surfactant composition |
| US10731107B2 (en) | 2017-06-30 | 2020-08-04 | The Procter & Gamble Company | Detergent compositions comprising AES surfactant having alkyl chain lengths of fourteen total carbons |
| US10836981B2 (en) | 2017-11-10 | 2020-11-17 | The Procter & Gamble Company | Anti-foam compositions comprising an organopolysiloxane with adjacent hydrolysable groups |
| US11130451B2 (en) | 2019-03-13 | 2021-09-28 | Guillermo Viniegra | Tailgate integrated toolbox |
| WO2020264077A1 (en) | 2019-06-28 | 2020-12-30 | The Procter & Gamble Company | Cleaning composition |
| WO2021067983A1 (en) | 2019-09-30 | 2021-04-08 | The Procter & Gamble Company | Fabric care compositions that include a copolymer and related methods |
| JP7381746B2 (ja) * | 2019-12-20 | 2023-11-15 | ザ プロクター アンド ギャンブル カンパニー | 粒子状布地ケア組成物 |
| EP4349950A2 (en) | 2020-05-14 | 2024-04-10 | The Procter & Gamble Company | Fabric care composition |
| CN115397888A (zh) | 2020-05-29 | 2022-11-25 | 巴斯夫欧洲公司 | 用于改进衣物洗涤剂去污力的两性改性低聚丙烯亚胺乙氧基化物 |
| CN116057159A (zh) * | 2020-09-28 | 2023-05-02 | 巴斯夫欧洲公司 | 洗衣用抗泛灰组合物 |
| WO2023094275A1 (en) | 2021-11-29 | 2023-06-01 | Basf Se | Amphoterically-modified trialkylene tetramine ethoxylates for improved stain removal of laundry detergents |
| CN115232277B (zh) * | 2022-08-11 | 2023-09-22 | 山东一诺威新材料有限公司 | 仿乳胶聚氨酯软质泡沫用特种聚醚多元醇及其制备方法 |
| US20240060016A1 (en) | 2022-08-12 | 2024-02-22 | The Procter & Gamble Company | Low-Water Compositions |
| US20240060015A1 (en) | 2022-08-12 | 2024-02-22 | The Procter & Gamble Company | Solid dissolvable compositions |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5869874A (ja) * | 1981-10-23 | 1983-04-26 | Takeo Saegusa | 双性イオン化化合物 |
| EP0111976B1 (en) * | 1982-12-23 | 1990-04-11 | THE PROCTER & GAMBLE COMPANY | Zwitterionic compounds having clay soil removal/anti-redeposition properties useful in detergent compositions |
| DE3446921A1 (de) * | 1984-12-21 | 1986-07-03 | Bayer Ag, 5090 Leverkusen | Neue alkoxylierte aminopolyether, verfahren zu ihrer herstellung und sie enthaltende kohle-wasser-aufschlaemmungen |
| US5049680A (en) * | 1990-05-03 | 1991-09-17 | Lce Partnership | Novel cationic lactam polymers and 1-(3-alkyl amino propyl)pyrrolidone-2 intermediates therefor |
| US5747440A (en) * | 1996-01-30 | 1998-05-05 | Procter & Gamble Company | Laundry detergents comprising heavy metal ion chelants |
| JP3148255B2 (ja) * | 1996-05-03 | 2001-03-19 | ザ、プロクター、エンド、ギャンブル、カンパニー | 綿防汚重合体 |
| DE19647060A1 (de) * | 1996-11-14 | 1998-05-20 | Huels Chemische Werke Ag | Verwendung von anionischen Geminitensiden in Formulierungen für Wasch-, Reinigungs- und Körperpflegemittel |
| AU728370B2 (en) * | 1996-12-20 | 2001-01-11 | Procter & Gamble Company, The | Dishwashing detergent compositions containing organic diamines |
-
2000
- 2000-07-05 AT AT00951335T patent/ATE251652T1/de not_active IP Right Cessation
- 2000-07-05 CN CNB008104107A patent/CN1158335C/zh not_active Expired - Fee Related
- 2000-07-05 DE DE60005839T patent/DE60005839T2/de not_active Expired - Lifetime
- 2000-07-05 WO PCT/EP2000/006296 patent/WO2001005874A1/en active IP Right Grant
- 2000-07-05 AU AU64315/00A patent/AU771572B2/en not_active Ceased
- 2000-07-05 EP EP00951335A patent/EP1198492B1/en not_active Expired - Lifetime
- 2000-07-05 MX MXPA02000446A patent/MXPA02000446A/es active IP Right Grant
- 2000-07-05 BR BRPI0012490-7A patent/BR0012490B1/pt not_active IP Right Cessation
- 2000-07-05 KR KR1020027000997A patent/KR100675579B1/ko not_active IP Right Cessation
- 2000-07-05 CA CA002379036A patent/CA2379036A1/en not_active Abandoned
- 2000-07-05 ES ES00951335T patent/ES2208388T3/es not_active Expired - Lifetime
- 2000-07-05 JP JP2001511525A patent/JP5174305B2/ja not_active Expired - Fee Related
-
2002
- 2002-02-15 ZA ZA200201296A patent/ZA200201296B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE60005839D1 (de) | 2003-11-13 |
| BR0012490A (pt) | 2002-04-02 |
| ATE251652T1 (de) | 2003-10-15 |
| JP2003505551A (ja) | 2003-02-12 |
| CN1158335C (zh) | 2004-07-21 |
| AU6431500A (en) | 2001-02-05 |
| BR0012490B1 (pt) | 2010-06-15 |
| EP1198492B1 (en) | 2003-10-08 |
| ES2208388T3 (es) | 2004-06-16 |
| WO2001005874A1 (en) | 2001-01-25 |
| KR100675579B1 (ko) | 2007-02-01 |
| DE60005839T2 (de) | 2004-05-06 |
| CN1361805A (zh) | 2002-07-31 |
| EP1198492A1 (en) | 2002-04-24 |
| KR20020016912A (ko) | 2002-03-06 |
| MXPA02000446A (es) | 2002-07-02 |
| CA2379036A1 (en) | 2001-01-25 |
| AU771572B2 (en) | 2004-03-25 |
| JP5174305B2 (ja) | 2013-04-03 |
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