DE19622981A1 - Acid adducts of fatty acid polyhydroxyalkylamides - Google Patents
Acid adducts of fatty acid polyhydroxyalkylamidesInfo
- Publication number
- DE19622981A1 DE19622981A1 DE19622981A DE19622981A DE19622981A1 DE 19622981 A1 DE19622981 A1 DE 19622981A1 DE 19622981 A DE19622981 A DE 19622981A DE 19622981 A DE19622981 A DE 19622981A DE 19622981 A1 DE19622981 A1 DE 19622981A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- residue
- adduct
- adducts
- compositions
- 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.)
- Withdrawn
Links
- 239000002253 acid Substances 0.000 title claims abstract description 41
- 150000004665 fatty acids Chemical class 0.000 title claims abstract description 19
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 18
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 18
- 239000000194 fatty acid Substances 0.000 title claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 5
- 150000007524 organic acids Chemical class 0.000 claims abstract description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 3
- 239000002562 thickening agent Substances 0.000 claims abstract 3
- 239000002904 solvent Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 150000002334 glycols Chemical class 0.000 claims description 9
- 150000001298 alcohols Chemical class 0.000 claims description 6
- 150000007942 carboxylates Chemical class 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 5
- 125000000129 anionic group Chemical group 0.000 claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000002280 amphoteric surfactant Substances 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 239000002736 nonionic surfactant Substances 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 239000004088 foaming agent Substances 0.000 claims 2
- 125000003563 glycoside group Chemical group 0.000 claims 2
- -1 alkyl amide Chemical class 0.000 abstract description 13
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 150000002338 glycosides Chemical class 0.000 abstract description 3
- 239000004604 Blowing Agent Substances 0.000 abstract 1
- 238000007664 blowing Methods 0.000 abstract 1
- 229930182470 glycoside Natural products 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 150000001450 anions Chemical class 0.000 description 6
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 5
- 238000005187 foaming Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000002168 alkylating agent Substances 0.000 description 4
- 229940100198 alkylating agent Drugs 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- 150000002191 fatty alcohols Chemical class 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 239000004310 lactic acid Substances 0.000 description 4
- 235000014655 lactic acid Nutrition 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 238000005956 quaternization reaction Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical class CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002402 hexoses Chemical class 0.000 description 3
- ROBFUDYVXSDBQM-UHFFFAOYSA-N hydroxymalonic acid Chemical compound OC(=O)C(O)C(O)=O ROBFUDYVXSDBQM-UHFFFAOYSA-N 0.000 description 3
- 229940050176 methyl chloride Drugs 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000003892 C18 acyl group Chemical group 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
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000008051 alkyl sulfates Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000011260 aqueous acid Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 239000001630 malic acid Substances 0.000 description 2
- 235000011090 malic acid Nutrition 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 description 2
- 150000002772 monosaccharides Chemical class 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 235000021313 oleic acid Nutrition 0.000 description 2
- 150000002972 pentoses Chemical class 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- 150000004043 trisaccharides Chemical class 0.000 description 2
- SXFBQAMLJMDXOD-UHFFFAOYSA-N (+)-hydrogentartrate bitartrate salt Chemical compound OC(=O)C(O)C(O)C(O)=O.OC(=O)C(O)C(O)C(O)=O SXFBQAMLJMDXOD-UHFFFAOYSA-N 0.000 description 1
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 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
- RRBZUCWNYQUCTR-UHFFFAOYSA-N 2-(aminoazaniumyl)acetate Chemical class NNCC(O)=O RRBZUCWNYQUCTR-UHFFFAOYSA-N 0.000 description 1
- OORRCVPWRPVJEK-UHFFFAOYSA-N 2-oxidanylethanoic acid Chemical compound OCC(O)=O.OCC(O)=O OORRCVPWRPVJEK-UHFFFAOYSA-N 0.000 description 1
- KVZLHPXEUGJPAH-UHFFFAOYSA-N 2-oxidanylpropanoic acid Chemical compound CC(O)C(O)=O.CC(O)C(O)=O KVZLHPXEUGJPAH-UHFFFAOYSA-N 0.000 description 1
- DBTMGCOVALSLOR-UHFFFAOYSA-N 32-alpha-galactosyl-3-alpha-galactosyl-galactose Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(OC2C(C(CO)OC(O)C2O)O)OC(CO)C1O DBTMGCOVALSLOR-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N Alanine Chemical class CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-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
- 239000005711 Benzoic acid Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- WQZGKKKJIJFFOK-WHZQZERISA-N D-aldose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-WHZQZERISA-N 0.000 description 1
- RXVWSYJTUUKTEA-UHFFFAOYSA-N D-maltotriose Natural products OC1C(O)C(OC(C(O)CO)C(O)C(O)C=O)OC(CO)C1OC1C(O)C(O)C(O)C(CO)O1 RXVWSYJTUUKTEA-UHFFFAOYSA-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
- KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 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 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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 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
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000002947 alkylene group Chemical group 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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 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
- 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
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000002238 fumaric acids Chemical class 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 150000005165 hydroxybenzoic acids Chemical class 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- FYGDTMLNYKFZSV-UHFFFAOYSA-N mannotriose Natural products OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(OC2C(OC(O)C(O)C2O)CO)C(O)C1O FYGDTMLNYKFZSV-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
- FYGDTMLNYKFZSV-BYLHFPJWSA-N β-1,4-galactotrioside 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]2[C@@H](O[C@@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-BYLHFPJWSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/22—Amides or hydrazides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/416—Quaternary ammonium compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/42—Amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
-
- 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
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
- C11D17/003—Colloidal solutions, e.g. gels; Thixotropic solutions or pastes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
Abstract
Description
Die Erfindung betrifft stark schäumende Säure-Addukte von Fettsäurepolyhydroxyalkylamiden und ein Verfahren zu deren Herstellung. Die Erfindung betrifft ferner Kompositionen mit diesen Addukten und die Verwendung der Säure-Addukte und der Kompositionen.The invention relates to highly foaming acid adducts of Fatty acid polyhydroxyalkylamides and a process for their Manufacturing. The invention further relates to compositions with these adducts and the use of the acid adducts and the Compositions.
Addukte von tertiären Fettaminen mit Säuren oder mit Alkylierungsmitteln wie Alkylhalogeniden, Alkylsulfaten oder Alkylenoxiden in Gegenwart einer wäßrigen Säure stellen wirksame und vielseitig verwendbare kationische Tenside dar.Adducts of tertiary fatty amines with acids or with Alkylating agents such as alkyl halides, alkyl sulfates or Make alkylene oxides in the presence of an aqueous acid effective and versatile cationic surfactants.
In DE-A-42 38 207 und DE-A-42 38 211 werden Addukte von Fettsäurepolyhydroxyalkylamiden (als Aminverbindung) mit Alkylierungsmitteln beschrieben. Die Herstellung dieser quaternären Ammoniumsalze erfolgt durch Quaternisierung (Alkylierung) von einem Fettsäurepolyhydroxyalkylamid mit einem Alkylierungsmittel wie Methylchlorid, Dimethylsulfat, Dimethylphosphat oder Ethylenoxid und/oder Propylenoxid in Gegenwart einer wäßrigen Säure. Wie in DE-A-42 38 207 ausgeführt wird, weisen diese Addukte eine hohe Kaltwasserdispergierbarkeit und ausgezeichnete antistatische und netzende Eigenschaften auf.In DE-A-42 38 207 and DE-A-42 38 211 adducts of Fatty acid polyhydroxyalkylamides (as an amine compound) with Alkylating agents described. The making of this quaternary ammonium salts are made by quaternization (Alkylation) of a fatty acid polyhydroxyalkylamide with an alkylating agent such as methyl chloride, dimethyl sulfate, Dimethyl phosphate or ethylene oxide and / or propylene oxide in Presence of an aqueous acid. As in DE-A-42 38 207 is carried out, these adducts have a high Cold water dispersibility and excellent antistatic and wetting properties.
Es wurde nun überraschenderweise gefunden, daß Addukte aus einem Fettsäurepolyhydroxyalkylamid in Form eines tertiären Amins und einer Säure (anstelle eines Alkylierungsmittels) ein hohes Schaumvermögen aufweisen. Die erfindungsgemäßen Säure-Addukte entsprechen der nachstehenden Formel (1)It has now surprisingly been found that adducts consist of a fatty acid polyhydroxyalkylamide in the form of a tertiary Amine and an acid (instead of an alkylating agent) have a high foaming power. The invention Acid adducts correspond to formula (1) below
worin
Z ein reduzierter Glycosidrest oder
Oligoglycosidrest mit 2 bis 6 Glycose-Einheiten,
x eine ganze Zahl von 2 bis 4,
R¹ ein C₁ bis C₄-Alkyl oder C₂ bis C₄-Hydroxyalkyl,
R² ein C₁ bis C₄-Alkyl oder C₂ bis C₄-Hydroxyalkyl,
CO-R ein aliphatischer Acylrest mit 6 bis
22 Kohlenstoffatomen und
A⁻ ein Anionrest einer anorganischen oder organischen
Säure ist.wherein
Z is a reduced glycoside residue or oligoglycoside residue with 2 to 6 glycose units,
x is an integer from 2 to 4,
R¹ is a C₁ to C₄ alkyl or C₂ to C₄ hydroxyalkyl,
R² is a C₁ to C₄-alkyl or C₂ to C₄-hydroxyalkyl,
CO-R is an aliphatic acyl radical with 6 to 22 carbon atoms and
A⁻ is an anionic residue of an inorganic or organic acid.
Bevorzugte Säure-Addukte sind solche wobei
Z ein reduzierter Glycosidrest oder Oligoglycosidrest mit
2 oder 3 Glycose-Einheiten (das ist ein Di- oder
Triglycosidrest),
x 3,
R¹ und R² (gleich oder verschieden) Methyl oder Ethyl und
CO-R ein Fettacylrest mit 8 bis 18 Kohlenstoffatomen ist.Preferred acid adducts are those wherein
Z is a reduced glycoside residue or oligoglycoside residue with 2 or 3 glycose units (this is a di- or triglycoside residue),
x 3,
R¹ and R² (same or different) methyl or ethyl and
CO-R is a fatty acyl radical having 8 to 18 carbon atoms.
Zu CO-R und Z sei im einzelnen noch folgendes gesagt: Der aliphatische Acylrest CO-R, der vorzugsweise der genannte Fettacylrest ist, kann gesättigt oder ungesättigt (vorzugsweise ein- bis dreifach ungesättigt) sein. Als Beispiele seien die Acylreste von Capryl-, Caprin-, Laurin-, Palmitin-, Stearin- und Ölsäure genannt sowie Cocosacyl, Talgacyl, vorzugsweise gehärtetes Talgacyl, und dergleichen. Der Fettsäurerest stellt häufig eine Mischung von zwei oder mehreren Acylgruppen dar, zum Beispiel C₁₂ und C₁₄-Acyl (C12/14), C₁₆ und C₁₈-Acyl (C16/18) oder C₁₂ bis C₁₈-Acyl. Der lineare Rest Z stammt, wie oben bereits erwähnt, vorzugsweise von Zuckeralkoholen, abgeleitet aus Mono-, Di- oder Trisacchariden. Als Monosaccharide sind Pentosen und Hexosen bevorzugt. Beispiele für Monosaccharide sind Glucose, Galaktose, Mannose und Talose als Hexosen und Arabinose, Ribose und Xylose als Pentosen. Beispiele für Di- und Trisaccharide (Polysaccharide) sind Lactose, Maltose, Maltotriose und dergleichen. Besonders bevorzugte Polyhydroxyalkylreste stammen von reduzierten Hexosen, insbesondere von Glucose (Sorbitylrest). Der besonders bevorzugte Rest Z entspricht also der nachstehenden FormelThe following may be said in detail about CO-R and Z: The aliphatic acyl radical CO-R, which is preferably the fatty acyl radical mentioned, can be saturated or unsaturated (preferably mono- to tri-unsaturated). Examples include the acyl residues of caprylic, capric, lauric, palmitic, stearic and oleic acid, and cocosacyl, tallow acyl, preferably hardened tallow acyl, and the like. The fatty acid residue is often a mixture of two or more acyl groups, for example C₁₂ and C₁₄ acyl (C 12/14 ), C₁₆ and C₁₈ acyl (C 16/18 ) or C₁₂ to C₁₈ acyl. As already mentioned above, the linear radical Z is preferably derived from sugar alcohols derived from mono-, di- or trisaccharides. Pentoses and hexoses are preferred as monosaccharides. Examples of monosaccharides are glucose, galactose, mannose and talose as hexoses and arabinose, ribose and xylose as pentoses. Examples of di- and trisaccharides (polysaccharides) are lactose, maltose, maltotriose and the like. Particularly preferred polyhydroxyalkyl radicals come from reduced hexoses, in particular from glucose (sorbityl radical). The particularly preferred radical Z thus corresponds to the formula below
Das Anion A⁻ der erfindungsgemäßen Addukte stammt im allgemeinen von einer Mineralsäure oder von einer (aliphatischen oder aromatischen) Carbonsäure. Bevorzugte anorganische Säuren sind Halogenwasserstoffsäuren wie HCl oder HBr, Kohlensäure, Phosphorsäure, Salpetersäure oder Schwefelsäure. Im Falle einer Carbonsäure ist das Anion ein Carboxylat. Bevorzugte Carbonsäuren sind C₁ bis C₃-Monocarbonsäuren wie Ameisensäure, Essigsäure oder Propionsäure; C₁₂ bis C₁₈-Monocarbonsäure wie Dodecansäure, Palmitinsäure, Stearinsäure oder Ölsäure; Dicarbonsäuren der Formel HOOC-(CH₂)n-COOH, worin n 0 oder eine ganze Zahl von 1 bis 8 ist, wie Oxal-, Malon-, Bernstein-, Glutar- oder Adipinsäure und die ungesättigten Dicarbonsäuren, Fumar- und Maleinsäure; Monohydroxy-monocarbonsäuren wie Glykolsäure (Hydroxy-essigsäure) oder Milchsäure (α-Hydroxy-propionsäure); Monohydroxy-dicarbonsäuren wie Tartronsäure (Monohydroxy-malonsäure) oder Äpfelsäure (Monohydroxy-bernsteinsäure); Dihydroxy-dicarbonsäuren wie Weinsäure (Dihydroxy-bernsteinsäure); Monohydroxy-tricarbonsäuren wie Citronensäure (Hydroxy-tricarballylsäure); Hydroxy-benzoesäuren wie Salicylsäure oder Gallussäure; und aromatische Dicarbonsäuren (Phthalsäuren) wie o-Phthalsäure oder p-Phthalsäure. Von den genannten organischen Säuren als Salzbildner sind die C1 bis C3-Monocarbonsäuren, die Milchsäure und die Fruchtsäuren besonders bevorzugt.The anion A⁻ of the adducts according to the invention generally comes from a mineral acid or from an (aliphatic or aromatic) carboxylic acid. Preferred inorganic acids are hydrohalic acids such as HCl or HBr, carbonic acid, phosphoric acid, nitric acid or sulfuric acid. In the case of a carboxylic acid, the anion is a carboxylate. Preferred carboxylic acids are C₁ to C₃ monocarboxylic acids such as formic acid, acetic acid or propionic acid; C₁₂ to C₁₈ monocarboxylic acid such as dodecanoic acid, palmitic acid, stearic acid or oleic acid; Dicarboxylic acids of the formula HOOC- (CH₂) n -COOH, where n is 0 or an integer from 1 to 8, such as oxalic, malonic, succinic, glutaric or adipic acid and the unsaturated dicarboxylic acids, fumaric and maleic acids; Monohydroxy-monocarboxylic acids such as glycolic acid (hydroxy-acetic acid) or lactic acid (α-hydroxy-propionic acid); Monohydroxy-dicarboxylic acids such as tartronic acid (monohydroxy-malonic acid) or malic acid (monohydroxy-succinic acid); Dihydroxy-dicarboxylic acids such as tartaric acid (dihydroxy-succinic acid); Monohydroxy-tricarboxylic acids such as citric acid (hydroxy-tricarballylic acid); Hydroxy-benzoic acids such as salicylic acid or gallic acid; and aromatic dicarboxylic acids (phthalic acids) such as o-phthalic acid or p-phthalic acid. Of the organic acids mentioned as salt formers, the C1 to C3 monocarboxylic acids, lactic acid and fruit acids are particularly preferred.
Das Anion A⁻ ist also vorzugsweise ein Halogenid, Carbonat, Phosphat, Nitrat, Sulfat oder Carboxylat, wobei Carboxylat besonders bevorzugt ist. Ausgehend von den genannten Säuren seien zur weiteren Erläuterung einige Beispiele für A⁻ angeführt: Halogenide wie Cl⁻, Br⁻; Sulfate wie (SO₄2-)1/2; Phosphate wie (PO₄3-)1/3; und Carboxylate wie CH₃COO⁻, C₁₁H₂₃COO⁻, CH₃-CH(OH)-COO⁻ (Anion der Milchsäure), ⁻OOC-CH(OH)-CH₂-COOH (Anion der Apfelsäure), C₆H₅-COO⁻ (Anion der Benzoesäure).The anion A⁻ is therefore preferably a halide, carbonate, phosphate, nitrate, sulfate or carboxylate, carboxylate being particularly preferred. Starting from the acids mentioned, some examples of A⁻ are given for further explanation: halides such as Cl⁻, Br⁻; Sulfates such as (SO₄ 2- ) 1/2 ; Phosphates such as (PO₄ 3- ) 1/3 ; and carboxylates such as CH₃COO⁻, C₁₁H₂₃COO⁻, CH₃-CH (OH) -COO⁻ (anion of lactic acid), ⁻OOC-CH (OH) -CH₂-COOH (anion of malic acid), C₆H₅-COO⁻ (anion of benzoic acid) .
Das erfindungsgemäße Verfahren zur Herstellung der Ammoniumsalze der Formel (1) ist dadurch gekennzeichnet, daß man ein Fettsäurepolyhydroxyalkylamid der nachstehenden Formel (2)The inventive method for producing the Ammonium salts of the formula (1) are characterized in that a fatty acid polyhydroxyalkylamide of the following Formula (2)
worin Z, x, R¹, R² und CO-R die angegebenen Bedeutungen
haben,
mit einer Säure der nachstehenden Formel (3)wherein Z, x, R¹, R² and CO-R have the meanings given,
with an acid of formula (3) below
HA (3)HA (3)
worin A die genannte Bedeutung hat,
zum Säure-Addukt der Formel (1) umsetzt.where A has the meaning given,
converted to the acid adduct of formula (1).
Bei der erfindungsgemäßen Umsetzung kann man die Reaktionskomponenten Polyhydroxyalkylamid und Säure innerhalb weiter Molverhältnisse einsetzen. So werden im allgemeinen 0,5 bis 1,5 mol Säure pro mol Fettsäurepolyhydroxyalkylamid, vorzugsweise 0,8 bis 1,2 mol und insbesondere 1 mol Säure pro mol Fettsäurepolyhydroxyalkylamid, eingesetzt. Die Temperatur der bei Atmosphärendruck ablaufenden Umsetzung liegt im allgemeinen bei 10 bis 120°C und vorzugsweise bei 25 bis 100°C. Die erfindungsgemäße Quaternisierung erfolgt durch Zusammenmischen der Reaktionskomponenten Säure und Polyhydroxyalkylamid. Sie kann in Substanz, das heißt in Abwesenheit von Lösungsmitteln, oder in Gegenwart von Lösungsmitteln, gegebenenfalls in Kombination mit anderen Tensiden, durchgeführt werden, wobei die Reaktion in Lösung bevorzugt ist. Geeignete Lösungsmittel sind Wasser; niedere Alkohole, vorzugsweise C₁ bis C₃-Alkanole wie Methanol, Ethanol, Propanol oder Isopropanol; niedere Glykole wie Ethylenglykol oder Propylenglykol; Oxalkylenglykole mit 2 bis 6 Ethylenoxid- und/oder Propylenoxid-Einheiten wie Diethylenglykol, Dipropylenglykol, Triethylenglykol, Pentaethylenglykol; Mono- oder Di-C₁ bis C₄-alkylether von niederen Glykolen oder Oxalkylenglykolen; und Fettalkoholalkoxylate, vorzugsweise Fettalkoholethoxylate mit 8 bis 18 Kohlenstoffatomen im Fettalkylrest und mit 2 bis 12 Ethylenoxid-Einheiten; sowie Mischungen davon. Von den genannten Lösungsmitteln sind Wasser, C₁ bis C₃-Alkanole, niedere Glykole und Mischungen davon bevorzugt. Die Menge an Lösungsmittel kann in weiten Grenzen variieren. Im allgemeinen werden 5 bis 80 Gew.-% Lösungsmittel eingesetzt, vorzugsweise 10 bis 70 Gew.-%, Gewichtsprozente bezogen auf die Mischung aus Fettsäurepolyhydroxyalkylamid und Lösungsmittel. Es ist bevorzugt, die genannte Mischung vorzulegen und die salzbildende Säure kontinuierlich oder portionsweise in die Mischung einzurühren. Die anorganische oder organische Säure kann als solche eingesetzt werden, vorzugsweise wird sie in Form einer Lösung in Wasser und/oder niederen Alkoholen eingesetzt. Nach Zugabe der Säureverbindung kann das Reaktionsgemisch zur Nachreaktion noch weitergerührt werden. Den Quaternisierungsverlauf kann man durch titrimetrische Bestimmung des basischen Stickstoffgehaltes im Reaktionsgemisch (Abnahme von Fettsäurepolyhydroxyalkylamid) verfolgen. Die Quaternisierung ist im allgemeinen nach 0,1 bis 2 Stunden beendet. Die angestrebte Salzbildung verläuft quantitativ und führt zur Bildung von Verbindungen der angegebenen Formel (1), die im Falle des Einsatzes von Lösungsmitteln in Form einer Lösung erhalten werden. Sofern erwünscht können die Säure-Addukte als solche gewonnen werden, zum Beispiel durch Entfernen des Lösungsmittels oder Isolierung aus dem Reaktionsgemisch.In the implementation of the invention Reaction components polyhydroxyalkylamide and acid use within wide molar ratios. So be generally 0.5 to 1.5 moles of acid per mole Fatty acid polyhydroxyalkylamide, preferably 0.8 to 1.2 mol and in particular 1 mol acid per mol Fatty acid polyhydroxyalkylamide used. The temperature the reaction taking place at atmospheric pressure lies in generally at 10 to 120 ° C and preferably at 25 to 100 ° C. The quaternization according to the invention is carried out by Mixing the reaction components acid and Polyhydroxyalkylamide. It can be in substance, that is in Absence of solvents, or in the presence of Solvents, optionally in combination with others Surfactants are carried out, the reaction in solution is preferred. Suitable solvents are water; lower Alcohols, preferably C₁ to C₃ alkanols such as methanol, Ethanol, propanol or isopropanol; lower glycols like Ethylene glycol or propylene glycol; With oxalkylene glycols 2 to 6 ethylene oxide and / or propylene oxide units such as Diethylene glycol, dipropylene glycol, triethylene glycol, Pentaethylene glycol; Mono- or di-C₁ to C₄ alkyl ethers of lower glycols or oxalkylene glycols; and Fatty alcohol alkoxylates, preferably fatty alcohol ethoxylates with 8 to 18 carbon atoms in the fatty alkyl radical and with 2 to 12 ethylene oxide units; as well as mixtures thereof. From the solvents mentioned are water, C₁ to C₃ alkanols, lower glycols and mixtures thereof prefers. The amount of solvent can vary widely vary. Generally 5 to 80 wt .-% Solvent used, preferably 10 to 70 wt .-%, Percentages by weight based on the mixture of Fatty acid polyhydroxyalkylamide and solvent. It is preferred to present the mixture mentioned and the salt-forming acid continuously or in portions into the Stir in the mixture. The inorganic or organic acid can be used as such, it is preferably used in Form of a solution in water and / or lower alcohols used. After adding the acid compound that can Reaction mixture for post-reaction are still stirred. The course of the quaternization can be determined by titrimetric Determination of the basic nitrogen content in the Reaction mixture (decrease of fatty acid polyhydroxyalkylamide) follow. The quaternization is generally after Ended 0.1 to 2 hours. The desired salt formation runs quantitatively and leads to the formation of connections of the given formula (1), which is used in the case of Solvents can be obtained in the form of a solution. Provided if desired, the acid adducts can be obtained as such , for example by removing the solvent or Isolation from the reaction mixture.
Die erfindungsgemäßen Kompositionen sind gekennzeichnet durch einen Gehalt von mindestens 5 Gew.-%, vorzugsweise 10 bis 70 Gew.-%, bezogen auf die Komposition, von mindestens einem Säure-Addukt der Formel (1). Bevorzugte Kompositionen bestehen im wesentlichen ausThe compositions according to the invention are characterized by a content of at least 5% by weight, preferably 10 to 70 wt .-%, based on the composition of at least one acid adduct of the formula (1). Preferred Compositions consist essentially of
- a) 10 bis 70 Gew.-%, vorzugsweise 15 bis 50 Gew.-%, von mindestens einem Säure-Addukt der Formel (1) als Wirkstoff unda) 10 to 70 wt .-%, preferably 15 to 50 wt .-%, of at least one acid adduct of the formula (1) as Active ingredient and
- b) 30 bis 90 Gew.-%, vorzugsweise 50 bis 85 Gew.-%, von einem Lösungsmittel, bestehend im wesentlichen aus Wasser, niederen Alkoholen, niederen Glykolen oder einer Mischung davon, Gewichtsprozente bezogen auf die Komposition.b) 30 to 90 wt .-%, preferably 50 to 85 wt .-%, of a solvent consisting essentially of Water, lower alcohols, lower glycols or one Mixture of these, percentages by weight based on the Composition.
Weitere bevorzugte Kompositionen bestehen im wesentlichen ausOther preferred compositions essentially exist out
- a′) 10 bis 70 Gew.-%, vorzugsweise 15 bis 50 Gew.-%, von mindestens einem Säure-Addukt der Formel (1) unda ') 10 to 70 wt .-%, preferably 15 to 50 wt .-%, of at least one acid adduct of the formula (1) and
- b′) 30 bis 90 Gew.-%, vorzugsweise 50 bis 85 Gew.%, von mindestens einem anderen kationischen und/oder anionischen und/oder nicht ionischen und/oder amphoteren Tensid, Gewichtsprozente bezogen auf die Komposition.b ') 30 to 90 wt .-%, preferably 50 to 85 wt.%, of at least one other cationic and / or anionic and / or non-ionic and / or amphoteric Surfactant, percentages by weight based on the composition.
Diese Kompositionen können als solche, das heißt frei von Lösungsmitteln, oder in Form einer Lösung vorliegen, wobei das Lösungsmittel Wasser, niedere Alkohole, niedere Glykole oder eine Mischung davon ist. Die Lösungen enthalten im allgemeinen 10 bis 70 Gew.-%, vorzugsweise 15 bis 50 Gew.-%, der Summe der Komponenten a′) und b′). Geeignete andere kationische Tenside sind zum Beispiel die üblichen quartären Ammoniumverbindungen mit vier Alkylresten am Stickstoffatom und quartäre Carbonsäureethanolaminester-Salze (Esterquats). Geeignete anionische Tenside sind zum Beispiel Alkylbenzolsulfonate, Alkansulfonate, Olefinsulfonate, Alkylethersulfonate, Glycerinethersulfonate, Alkylsulfate, Fettalkoholethersulfate, Glycerinethersulfate, Fettsäureamid(ether)sulfate, Sulfosuccinate, Sarcosinate und Tauride. Geeignete nichtionische Tenside sind zum Beispiel Fettsäurepolyhydroxyalkylamide, Fettalkoholpolyglycolether, Alkylphenolpolyglycolether, Fettsäurepolyglycolester, Fettsäureamidpolyglycolether, Fettaminpolyglycolether, alkoxylierte Triglyceride, Sorbitanester und Alkylpolyglycoside. Geeignete amphotere oder zwitterionische Tenside sind zum Beispiel Alkylbetaine, Alkylamidobetaine, Aminopropionate, Aminoglycinate, Imidazoliniumbetaine und Sulfobetaine.These compositions as such, that is, free from Solvents, or in the form of a solution, wherein the solvent water, lower alcohols, lower glycols or a mixture of them. The solutions included in the generally 10 to 70% by weight, preferably 15 to 50% by weight, the sum of the components a ′) and b ′). Other suitable For example, cationic surfactants are the usual quaternaries Ammonium compounds with four alkyl radicals on the nitrogen atom and quaternary carboxylic acid ethanolamine ester salts (esterquats). Suitable anionic surfactants are, for example Alkylbenzenesulfonates, alkanesulfonates, olefinsulfonates, Alkyl ether sulfonates, glycerol ether sulfonates, alkyl sulfates, Fatty alcohol ether sulfates, glycerol ether sulfates, Fatty acid amide (ether) sulfates, sulfosuccinates, sarcosinates and Tauride. Suitable nonionic surfactants are, for example Fatty acid polyhydroxyalkylamides, fatty alcohol polyglycol ethers, Alkylphenol polyglycol ether, fatty acid polyglycol ester, Fatty acid amide polyglycol ether, fatty amine polyglycol ether, alkoxylated triglycerides, sorbitan esters and Alkyl polyglycosides. Suitable amphoteric or zwitterionic Surfactants are, for example, alkyl betaines, alkyl amido betaines, Aminopropionates, aminoglycinates, imidazolinium betaines and Sulfobetaines.
Die erfindungsgemäßen Kompositionen werden durch Zusammenmischen der angegebenen Komponenten bei etwa 15 bis 100°C hergestellt oder werden bereits im Rahmen der Herstellung von Säure-Addukten der Formel (1) erhalten, worauf gegebenenfalls weitere Tenside hinzugefügt werden können.The compositions according to the invention are made by Mix together the specified components at about 15 to 100 ° C or are already in the scope of Obtaining preparation of acid adducts of the formula (1), whereupon further surfactants may be added can.
Die erfindungsgemäßen Salzverbindungen der Formel (1) und ihre Kompositionen weisen ein unerwartet hohes Schaumvermögen auf und stellen deshalb ein hervorragendes Schaummittel dar. Aufgrund ihrer weiteren Eigenschaften wie gute Hautverträglichkeit und hohe Verdickbarkeit werden sie ferner vorteilhaft als Wasch- und Kosmetiktenside, vorzugsweise als Haar- und Körperpflegemittel, verwendet.The salt compounds of formula (1) and her compositions are unexpectedly high Foaming power and are therefore excellent Foam agent. Because of their other properties such they become good skin tolerance and high thickenability also advantageous as a detergent and cosmetic surfactant, preferably as hair and body care products, used.
Die Erfindung wird nun an Beispielen und Vergleichsbeispielen noch näher erläutert.The invention will now be illustrated by examples and Comparative examples explained in more detail.
Herstellung von Fettsäurepolyhydroxyalkylamid
C12/14-Dimethylaminopropyl-Glucamid (DMAP-GA):
304,5 g einer 41gew.%igen wäßrigen Lösung eines technischen
N-(3-Dimethylamino)-propylglucamins (im folgenden DMAP-G)
mit einem DMAP-G-Gehalt von 96 Gew.-%, bezogen auf
Festsubstanz (das sind 0,45 mol DMAP-G), werden mit Hilfe
einer üblichen Strippapparatur entwässert. Dazu wird die
Lösung auf etwa 100°C erhitzt und zunächst bei Normaldruck
bis zu einem Restwassergehalt von etwa 5 Gew.-% entwässert.
Die Lösung wird nun zur weiteren Entwässerung auf 130°C
erhitzt und bei dieser Temperatur gehalten, wobei
schrittweise ein Vakuum von bis zu 25 mbar angelegt wird. Es
wird bis zu einem Restwassergehalt von 0,2 Gew.-%
entwässert. Zur so erhaltenen Schmelze werden bei 130°C
unter Rühren 104,1 g (0,473 mol) C12/14-Fettsäuremethylester
(Molmasse 220 g/mol, nach Verseifungszahl) gegeben. Die
Mischung hat eine Temperatur von 120°C. Nun werden noch
6,1 g Natriummethylat (30gew.%ig in Methanol, 7,5 Mol-%,
bezogen auf DMAP-G) innerhalb von 3 Minuten zugetropft und
die Reaktionsmischung bei etwa 100°C gehalten. Das durch
die Reaktion entstehende Methanol wird zunächst im System
belassen. Nach etwa 20 Minuten liegt eine klare
Reaktionslösung vor. Nun wird ein Vakuum von 60 mbar
angelegt und eine Temperatur von circa 95°C eingestellt,
wobei die Reaktionsmischung etwa 80 Minuten unter
Abdestillation des Methanols weiterreagiert. Die so
erhaltene Lösung enthält circa 90 Gew.-% C12/14-DMAP-GA,
bezogen auf den Feststoffanteil.
Production of fatty acid polyhydroxyalkylamide C 12/14 dimethylaminopropyl glucamide (DMAP-GA):
304.5 g of a 41% by weight aqueous solution of a technical N- (3-dimethylamino) propylglucamine (hereinafter DMAP-G) with a DMAP-G content of 96% by weight, based on the solid substance (that is 0 , 45 mol DMAP-G) are dewatered using a conventional stripping apparatus. For this purpose, the solution is heated to about 100 ° C. and first dewatered at normal pressure to a residual water content of about 5% by weight. The solution is then heated to 130 ° C. for further dewatering and kept at this temperature, a vacuum of up to 25 mbar being gradually applied. It is dewatered up to a residual water content of 0.2% by weight. 104.1 g (0.473 mol) of C 12/14 fatty acid methyl ester (molar mass 220 g / mol, based on the saponification number) are added to the melt thus obtained at 130 ° C. with stirring. The mixture has a temperature of 120 ° C. 6.1 g of sodium methylate (30% by weight in methanol, 7.5 mol%, based on DMAP-G) are then added dropwise within 3 minutes and the reaction mixture is kept at about 100.degree. The methanol resulting from the reaction is initially left in the system. After about 20 minutes there is a clear reaction solution. A vacuum of 60 mbar is now applied and a temperature of approximately 95 ° C. is set, the reaction mixture continuing to react for about 80 minutes while the methanol is distilled off. The solution thus obtained contains approximately 90% by weight of C 12/14 DMAP-GA, based on the solids content.
Herstellung von C12/14-DMAP-GA-Hydrochlorid (Addukt 1):Production of C 12/14 DMAP GA hydrochloride (adduct 1):
Zu einer 50gew.%igen wäßrigen Lösung von C12/14-DMAP-GA wird unter Rühren bei 70°C innerhalb 20 Minuten eine äquimolare Menge konzentrierter Salzsäure zugetropft; anschließend läßt man die das erfindungsgemäße Produkt enthaltende Lösung - bei Bedarf ist eine Isolierung des Säure-Addukts selbstverständlich möglich - unter fortgesetztem Rühren erkalten.. To a 50% aqueous solution of C 12/14 -DMAP-GA is added dropwise with stirring at 70 ° C over 20 minutes an equimolar amount of concentrated hydrochloric acid; the solution containing the product according to the invention is then allowed to cool, with isolation of the acid adduct being possible, of course, with continued stirring.
Herstellung von C12/14-DMAP-GA-Milchsäure-Addukt (Addukt 2):Preparation of C 12/14 DMAP-GA Lactic Acid Adduct (Adduct 2):
Das erfindungsgemäße Lactat (Addukt 2) wird hergestellt, indem man analog Beispiel 1 anstelle von Salzsäure eine wäßrige Milchsäurelösung zutropft; gegebenenfalls ist das gelöste Produkt durch Abdestillation des Wassers natürlich auch in Substanz zu erhalten.The lactate according to the invention (adduct 2) is produced by analogously to Example 1 instead of hydrochloric acid added dropwise aqueous lactic acid solution; if applicable, that is dissolved product by distilling off the water naturally also get in substance.
Die erfindungsgemäßen Lösungen von Addukt 1 und Addukt 2 werden mit einer Lösung des entsprechenden N-methylierten Quats (mit Chlorid als Gegenion) - dessen Herstellung erfolgt durch Umsetzung von C12/14-DMAP-GA mit Methylchlorid analog DE-A-42 38 207 - verglichen, das ist C12/14-DMAP-GA-Methylchlorid-Quat (Addukt 3):The solutions of adduct 1 and adduct 2 according to the invention are mixed with a solution of the corresponding N-methylated quat (with chloride as counterion) - the preparation of which is carried out by reacting C 12/14 -DMAP-GA with methyl chloride analogously to DE-A-42 38 207 - compared, this is C 12/14 DMAP GA methyl chloride quat (adduct 3):
Die überraschenden Eigenschaften des Hydrochlorids (Addukt 1) und des Lactats (Addukt 2) gegenüber dem Methylchlorid-Quat (Addukt 3) zeigen sich beispielsweise beim Schäumvermögen der Einzeltenside. So weist die nach Ross-Miles (Temperatur 37°C, Wasserhärte 15° dH, Zeit: sofort/5 Minuten) bestimmte Schaumhöhe in Millimetern bereits bei einer kritischen Konzentration von 0,03% WAS (wirkungsaktive Substanz) über einen pH-Bereich von 4 bis 9 signifikante Unterschiede auf, wie die nachstehende Zusammenfassung zeigt (die Messung von Addukt 2 wird nur bei pH 7 durchgeführt).The surprising properties of hydrochloride (Adduct 1) and the lactate (adduct 2) compared to the Methyl chloride quat (adduct 3) is shown, for example the foaming power of the individual surfactants. So it proves Ross-Miles (temperature 37 ° C, water hardness 15 ° dH, Time: immediately / 5 minutes) certain foam height in millimeters even at a critical concentration of 0.03% WAS (active substance) over a pH range of 4 to 9 significant differences on how the below Summary shows (the measurement of adduct 2 is only at pH 7 carried out).
Bemerkenswert ist auch die unterschiedliche Verdickbarkeit in Kombination mit Ethersulfat (als Einzeltensid lassen sich alle drei Produkte nicht verdicken!) unter neutralen Bedingungen (pH 7). Untersucht wurden Mischungen mit ®Genapol LRO (® = eingetragenes Warenzeichen von Hoechst), einem durch Oxalkylierung eines C12/14-Fettalkohols mit 2 Moläquivalenten Ethylenoxid und anschließende Sulfierung hergestelltem Natriumethersulfat (Ethersulfat : Prüfprodukt = 7 : 3) bei 15% WAS (Meßgröße mPa·s):Also noteworthy is the different thickenability in combination with ether sulfate (all three products cannot be thickened as a single surfactant!) Under neutral conditions (pH 7). Mixtures with ®Genapol LRO (® = registered trademark of Hoechst), a sodium ether sulfate (ether sulfate: test product = 7: 3) prepared by oxalkylation of a C 12/14 fatty alcohol with 2 molar equivalents of ethylene oxide and subsequent sulfonation were examined at 15% WAS (measured variable mPas):
Daß sich das Lactat (Addukt 2) ohne Elektrolyt-Zusatz stark verdicken läßt, ist absolut außergewöhnlich und für verschiedene Spezialanwendungen von großem Interesse.That the lactate (adduct 2) is strong without the addition of electrolyte thicken is absolutely exceptional and for various special applications of great interest.
Claims (13)
Z ein reduzierter Glycosidrest oder Oligoglycosidrest mit 2 bis 6 Glycose-Ein heiten,
x eine ganze Zahl von 2 bis 4,
R¹ ein C₁ bis C₄-Alkyl oder C₂ bis C₄-Hydroxyalkyl,
R² ein C₁ bis C₄-Alkyl oder C₂ bis C₄-Hydroxyalkyl,
CO-R ein aliphatischer Acylrest mit 6 bis 22 Kohlenstoffatomen und
A⁻ ein Anionrest einer anorganischen oder organischen Säure ist.1. Acid adducts of fatty acid polyhydroxyalkylamides of the following formula (1) wherein
Z is a reduced glycoside residue or oligoglycoside residue with 2 to 6 glycose units,
x is an integer from 2 to 4,
R¹ is a C₁ to C₄ alkyl or C₂ to C₄ hydroxyalkyl,
R² is a C₁ to C₄-alkyl or C₂ to C₄-hydroxyalkyl,
CO-R is an aliphatic acyl radical with 6 to 22 carbon atoms and
A⁻ is an anionic residue of an inorganic or organic acid.
Z ein reduzierter Glycosidrest oder ein Oligoglycosidrest mit 2 oder 3 Glycose-Einheiten,
x 3,
R¹ und R² Methyl oder Ethyl und
CO-R ein Fettacylrest mit 8 bis 18 Kohlenstoffatomen ist.2. Acid adducts according to claim 1, characterized in that
Z is a reduced glycoside residue or an oligoglycoside residue with 2 or 3 glycose units,
x 3,
R¹ and R² are methyl or ethyl and
CO-R is a fatty acyl radical having 8 to 18 carbon atoms.
mit einer Säure der nachstehenden Formel (3)HA (3)worin A die genannte Bedeutung hat,
zum Säure-Addukt der Formel (1) umsetzt.6. A process for the preparation of acid adducts according to claim 1, characterized in that a fatty acid polyhydroxyalkylamide of the following formula (2) wherein Z, x, R¹, R² and CO-R have the meanings given,
with an acid of the following formula (3) HA (3) in which A has the meaning given,
converted to the acid adduct of formula (1).
- a) 10 bis 70 Gew.-% von dem Säure-Addukt und
- b) 30 bis 90 Gew.-% von einem Lösungsmittel, wobei das Lösungsmittel im wesentlichen aus Wasser, niederen Alkoholen, niederen Glykolen oder einer Mischung davon gebildet ist, Gewichtsprozente bezogen auf die Komposition.
- a) 10 to 70 wt .-% of the acid adduct and
- b) 30 to 90% by weight of a solvent, the solvent being essentially formed from water, lower alcohols, lower glycols or a mixture thereof, percentages by weight based on the composition.
- a′) 10 bis 70 Gew.-% von dem Säure-Addukt und
- b′) 30 bis 90 Gew.-% von mindestens einem anderen kationischen und/oder anionischen und/oder nichtionischen und/oder amphoteren Tensid, Gewichtsprozente bezogen auf die Komposition.
- a ') 10 to 70 wt .-% of the acid adduct and
- b ') 30 to 90 wt .-% of at least one other cationic and / or anionic and / or nonionic and / or amphoteric surfactant, percentages by weight based on the composition.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19622981A DE19622981A1 (en) | 1996-06-08 | 1996-06-08 | Acid adducts of fatty acid polyhydroxyalkylamides |
AU30307/97A AU3030797A (en) | 1996-06-08 | 1997-05-30 | Acid addition compounds of fatty acid polyhydroxy alkyl amides |
PCT/EP1997/002811 WO1997047591A1 (en) | 1996-06-08 | 1997-05-30 | Acid addition compounds of fatty acid polyhydroxy alkyl amides |
EP97925021A EP0906269A1 (en) | 1996-06-08 | 1997-05-30 | Acid addition compounds of fatty acid polyhydroxy alkyl amides |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19622981A DE19622981A1 (en) | 1996-06-08 | 1996-06-08 | Acid adducts of fatty acid polyhydroxyalkylamides |
Publications (1)
Publication Number | Publication Date |
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DE19622981A1 true DE19622981A1 (en) | 1997-12-11 |
Family
ID=7796453
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19622981A Withdrawn DE19622981A1 (en) | 1996-06-08 | 1996-06-08 | Acid adducts of fatty acid polyhydroxyalkylamides |
Country Status (4)
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---|---|
EP (1) | EP0906269A1 (en) |
AU (1) | AU3030797A (en) |
DE (1) | DE19622981A1 (en) |
WO (1) | WO1997047591A1 (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1314718A1 (en) * | 2001-11-23 | 2003-05-28 | Cognis Iberia, S.L. | Quaternised fatty acid amidoamines |
EP1894989A1 (en) * | 2006-09-01 | 2008-03-05 | The Procter and Gamble Company | Pasty Composition for Sanitary Ware |
US11116220B2 (en) | 2017-12-22 | 2021-09-14 | Ecolab Usa Inc. | Antimicrobial compositions with enhanced efficacy |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4238207A1 (en) * | 1992-11-12 | 1994-05-19 | Henkel Kgaa | New quat. fatty acid poly:hydroxy:alkylamide(s) - useful in prodn. of antistatic agents for tissue and textile surfaces |
DE4238211C2 (en) * | 1992-11-12 | 1997-11-13 | Henkel Kgaa | Use of detergent mixtures containing cationic sugar surfactants and other surfactants for the production of softeners |
US5534197A (en) * | 1994-01-25 | 1996-07-09 | The Procter & Gamble Company | Gemini polyhydroxy fatty acid amides |
US5512699A (en) * | 1994-01-25 | 1996-04-30 | The Procter & Gamble Company | Poly polyhydroxy fatty acid amides |
DE19512299A1 (en) * | 1995-04-05 | 1996-10-10 | Hoechst Ag | New N-acyl-N-poly:hydroxy-hydrocarbyl di:amino-propane |
-
1996
- 1996-06-08 DE DE19622981A patent/DE19622981A1/en not_active Withdrawn
-
1997
- 1997-05-30 WO PCT/EP1997/002811 patent/WO1997047591A1/en not_active Application Discontinuation
- 1997-05-30 AU AU30307/97A patent/AU3030797A/en not_active Abandoned
- 1997-05-30 EP EP97925021A patent/EP0906269A1/en not_active Withdrawn
Also Published As
Publication number | Publication date |
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AU3030797A (en) | 1998-01-07 |
WO1997047591A1 (en) | 1997-12-18 |
EP0906269A1 (en) | 1999-04-07 |
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