JP6347723B2 - トリス−(2−ヒドロキシエチル)−メチルアンモニウムメチルスルファート脂肪酸エステルの製造方法 - Google Patents
トリス−(2−ヒドロキシエチル)−メチルアンモニウムメチルスルファート脂肪酸エステルの製造方法 Download PDFInfo
- Publication number
- JP6347723B2 JP6347723B2 JP2014225357A JP2014225357A JP6347723B2 JP 6347723 B2 JP6347723 B2 JP 6347723B2 JP 2014225357 A JP2014225357 A JP 2014225357A JP 2014225357 A JP2014225357 A JP 2014225357A JP 6347723 B2 JP6347723 B2 JP 6347723B2
- Authority
- JP
- Japan
- Prior art keywords
- fatty acid
- hydroxyethyl
- tris
- acid ester
- amine
- 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.)
- Active
Links
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 76
- 239000000194 fatty acid Substances 0.000 title claims description 76
- 229930195729 fatty acid Natural products 0.000 title claims description 76
- -1 tris- (2-hydroxyethyl) -methylammonium methylsulfate fatty acid ester Chemical class 0.000 title claims description 63
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 81
- 239000000203 mixture Substances 0.000 claims description 58
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 39
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 30
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 30
- 238000005956 quaternization reaction Methods 0.000 claims description 27
- 239000002516 radical scavenger Substances 0.000 claims description 26
- 239000011973 solid acid Substances 0.000 claims description 26
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 24
- 239000011541 reaction mixture Substances 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 18
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 125000005313 fatty acid group Chemical group 0.000 claims description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 12
- 239000002979 fabric softener Substances 0.000 claims description 12
- 239000000835 fiber Substances 0.000 claims description 10
- 239000002245 particle Substances 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 239000011630 iodine Substances 0.000 claims description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 238000005119 centrifugation Methods 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 6
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
- 239000007983 Tris buffer Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical group 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims description 2
- FVJLCPJDDAGIJE-UHFFFAOYSA-N tris(2-hydroxyethyl)-methylazanium Chemical compound OCC[N+](C)(CCO)CCO FVJLCPJDDAGIJE-UHFFFAOYSA-N 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims 2
- 150000004665 fatty acids Chemical class 0.000 description 14
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 12
- 239000003760 tallow Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 3
- 239000000347 magnesium hydroxide Substances 0.000 description 3
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 3
- WLTHPEHYBIKNHR-UHFFFAOYSA-M methyl sulfate;tris(2-hydroxyethyl)-methylazanium Chemical compound COS([O-])(=O)=O.OCC[N+](C)(CCO)CCO WLTHPEHYBIKNHR-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000007848 Bronsted acid Substances 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 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 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 235000021281 monounsaturated fatty acids Nutrition 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000357 carcinogen Toxicity 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000002496 iodine Chemical class 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- QWDJLDTYWNBUKE-UHFFFAOYSA-L magnesium bicarbonate Chemical compound [Mg+2].OC([O-])=O.OC([O-])=O QWDJLDTYWNBUKE-UHFFFAOYSA-L 0.000 description 1
- 239000002370 magnesium bicarbonate Substances 0.000 description 1
- 229910000022 magnesium bicarbonate Inorganic materials 0.000 description 1
- 235000014824 magnesium bicarbonate Nutrition 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000031 sodium sesquicarbonate Inorganic materials 0.000 description 1
- 235000018341 sodium sesquicarbonate Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- WCTAGTRAWPDFQO-UHFFFAOYSA-K trisodium;hydrogen carbonate;carbonate Chemical compound [Na+].[Na+].[Na+].OC([O-])=O.[O-]C([O-])=O WCTAGTRAWPDFQO-UHFFFAOYSA-K 0.000 description 1
- 125000005314 unsaturated fatty acid group Chemical group 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
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C219/06—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C219/08—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to an acyclic carbon atom of an acyclic unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/24—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfuric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
- C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
- C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
- C07C305/06—Hydrogenosulfates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
- C07C51/493—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification whereby carboxylic acid esters are formed
-
- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2003—Alcohols; Phenols
- C11D3/2006—Monohydric alcohols
- C11D3/201—Monohydric alcohols linear
-
- 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
- C11D3/26—Organic compounds containing nitrogen
- C11D3/30—Amines; Substituted amines ; Quaternized amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
市販のトリス−(2−ヒドロキシエチル)−メチルアンモニウム メチルスルファート獣脂脂肪酸エステルのメタノール含有量
表1は、市販のトリス−(2−ヒドロキシエチル)−メチルアンモニウム メチルスルファート獣脂脂肪酸エステルの、ヘッドスペースGCにより決定したメタノール含有量を示す。
トリス−(2−ヒドロキシエチル)−アミン獣脂脂肪酸エステルの製造
36のヨウ素価を有する獣脂脂肪酸2006g(6.44mol)及びトリエタノールアミン632g(4.26mol)の混合物を、撹拌しながら180℃に加熱し、反応混合物から水を留去した。この温度で1時間後に、圧力を段階的に10mbarにまで低下させ、この混合物を180℃でかつ10mbarで更に2時間撹拌した。生じたトリス−(2−ヒドロキシエチル)−アミン獣脂脂肪酸エステルは、7.0mg KOH/gの酸価及び93.7mg KOH/gの全アミン価を有していた。
例3(比較例)
ジメチルスルファート111.7g(0.89mol)を、例2からのトリス−(2−ヒドロキシエチル)−アミン獣脂脂肪酸エステル563g(0.94mol)に撹拌しながら少しずつ添加し、温度を60〜90℃の範囲内に維持するために反応混合物を冷却した。ジメチルスルファートを全て添加した後に、この反応混合物を85℃で1時間撹拌した。次いで、2−プロパノール75.1gを添加し、この混合物を均質になるまで撹拌した。生じた組成物は、4.6mg KOH/gの全アミン価を有し、かつこの組成物の質量を基準としてメタノール3200ppmを有していた。
ジメチルスルファート92.2g(0.73mol)を、例2からのトリス−(2−ヒドロキシエチル)−アミン獣脂脂肪酸エステル465.6g(0.78mol)及び炭酸水素ナトリウム14g(0.17mol)の混合物に撹拌しながら少しずつ添加し、温度を60〜90℃の範囲内に維持するために反応混合物を冷却した。ジメチルスルファートを全て添加した後に、この反応混合物を85℃で1時間撹拌した。次いで、2−プロパノール62.0gを添加し、この混合物を均質になるまで撹拌し、未反応の炭酸水素ナトリウムを除去するために加圧濾過器により濾過した。生じた組成物は、9.1mg KOH/gの全アミン価を有し、かつこの組成物の質量を基準としてメタノール190ppmを有していた。
ジメチルスルファート114.7g(0.91mol)を、例2からのトリス−(2−ヒドロキシエチル)−アミン獣脂脂肪酸エステル563g(0.94mol)に撹拌しながら少しずつ添加し、温度を60〜90℃の範囲内に維持するために反応混合物を冷却した。ジメチルスルファートを全て添加した後に、この反応混合物を85℃で1時間撹拌した。次いで、2−プロパノール75.3gを添加し、この混合物を均質になるまで撹拌した。生じた組成物は、3.1mg KOH/gの全アミン価を有し、かつこの組成物の質量を基準としてメタノール4000ppmを有していた。
ジメチルスルファート86.9g(0.69mol)を、例2からのトリス−(2−ヒドロキシエチル)−アミン獣脂脂肪酸エステル428.9g(0.716mol)及び炭酸水素ナトリウム10.6g(0.13mol)の混合物に撹拌しながら少しずつ添加し、温度を60〜90℃の範囲内に維持するために反応混合物を冷却した。ジメチルスルファートを全て添加した後に、この反応混合物を85℃で1時間撹拌した。次いで、2−プロパノール57.9gを添加し、この混合物を均質になるまで撹拌し、未反応の炭酸水素ナトリウムを除去するために加圧濾過器により濾過した。生じた組成物は、6.4mg KOH/gの全アミン価を有し、かつこの組成物の質量を基準としてメタノール1100ppmを有していた。
ジメチルスルファート94.6g(0.75mol)を、例2からのトリス−(2−ヒドロキシエチル)−アミン獣脂脂肪酸エステル466.6g(0.78mol)及び水酸化マグネシウム8.6g(0.147mol)の混合物に撹拌しながら少しずつ添加し、温度を60〜90℃の範囲内に維持するために反応混合物を冷却した。ジメチルスルファートを全て添加した後に、この反応混合物を85℃で1時間撹拌した。次いで、2−プロパノール63.0gを添加し、この混合物を均質になるまで撹拌し、未反応の水酸化マグネシウムを除去するために加圧濾過器により濾過した。生じた組成物は、6.9mg KOH/gの全アミン価を有し、かつこの組成物の質量を基準としてメタノール610ppmを有していた。
Claims (16)
- トリス−(2−ヒドロキシエチル)−アミン脂肪酸エステルをジメチルスルファートで四級化する工程を有するトリス−(2−ヒドロキシエチル)−メチルアンモニウム メチルスルファート脂肪酸エステルの製造方法において、前記四級化を、固体の酸スカベンジャーの存在で実施し、かつ前記トリス−(2−ヒドロキシエチル)−アミン脂肪酸エステルの脂肪酸基は、16〜18個の炭素原子の平均鎖長を有する、トリス−(2−ヒドロキシエチル)−メチルアンモニウム メチルスルファート脂肪酸エステルの製造方法。
- 前記固体の酸スカベンジャーは、アルカリ金属炭酸塩、アルカリ金属炭酸水素塩、アルカリ土類金属炭酸塩、アルカリ土類金属酸化物及びアルカリ土類金属水酸化物から選択される、請求項1に記載の方法。
- 前記固体の酸スカベンジャーは、炭酸ナトリウム又は炭酸水素ナトリウムである、請求項2に記載の方法。
- 前記固体の酸スカベンジャーは、少なくとも100μmの中央粒径を有する粒子からなる、請求項1から3までのいずれか1項に記載の方法。
- 前記固体の酸スカベンジャーを、四級化により得られた反応混合物から濾過又は遠心分離により除去する、請求項1から4までのいずれか1項記載の方法。
- エタノール、1−プロパノール、2−プロパノール、エチレングリコール、ジエチレングリコール、プロピレングリコール、ジプロピレングリコール、エチレングリコールのC1〜C4−アルキルモノエーテル、プロピレングリコールのC1〜C4−アルキルモノエーテル及びこれらの混合物から選択された溶剤を、前記固体の酸スカベンジャーの分離の前に、四級化により得られた前記反応混合物に添加する、請求項5に記載の方法。
- 分離された固体の酸スカベンジャーを前記溶剤で洗浄して洗浄液を生じさせ、前記洗浄液を四級化により得られた前記反応混合物への溶剤の添加のために再使用する、請求項6に記載の方法。
- ジメチルスルファートのトリス−(2−ヒドロキシエチル)−アミン脂肪酸エステルに対するモル比の値は0.9〜0.98である、請求項1から7までのいずれか1項に記載の方法。
- 四級化を、60〜95℃の温度で実施する、請求項1から8までのいずれか1項に記載の方法。
- 前記トリス−(2−ヒドロキシエチル)−アミン脂肪酸エステルは、脂肪酸基の窒素に対する平均モル比の値が1.4〜2.0である、請求項1から9までのいずれか1項に記載の方法。
- 前記トリス−(2−ヒドロキシエチル)−アミン脂肪酸エステルの脂肪酸基は、ヨウ素価が0.5〜120である、請求項1から10までのいずれか1項に記載の方法。
- 前記トリス−(2−ヒドロキシエチル)−アミン脂肪酸エステルは、10mol%未満のポリ不飽和脂肪酸基を有する、請求項1から11までのいずれか1項に記載の方法。
- 繊維柔軟剤活性組成物であって、
a) 少なくとも1種のトリス−(2−ヒドロキシエチル)−メチルアンモニウム メチルスルファート脂肪酸エステル65〜98質量%、
b) 前記繊維柔軟剤活性組成物の、2mg KOH/g以上で7mg KOH/g未満の全アミン価を提供する量の、対応する非四級化トリス−(2−ヒドロキシエチル)−アミン脂肪酸エステル、及び
c) メタノール1〜1500ppm
を有する、繊維柔軟剤活性組成物。 - メタノール10〜800ppmを有する、請求項13に記載の繊維柔軟剤活性組成物。
- 更に、エタノール、1−プロパノール、2−プロパノール、エチレングリコール、ジエチレングリコール、プロピレングリコール、ジプロピレングリコール、エチレングリコールのC1〜C4−アルキルモノエーテル、プロピレングリコールのC1〜C4−アルキルモノエーテル及びこれらの混合物から選択された溶剤を35質量%まで含有する、請求項13又は14に記載の繊維柔軟剤活性組成物。
- 請求項10から12までのいずれか1項に定義されたトリス−(2−ヒドロキシエチル)−アミン脂肪酸エステルに対応するトリス−(2−ヒドロキシエチル)−メチルアンモニウム メチルスルファート脂肪酸エステル65〜98質量%を含有する請求項13から15までのいずれか1項に記載の繊維柔軟剤活性組成物。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP13191579.5 | 2013-11-05 | ||
EP13191579 | 2013-11-05 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2015089889A JP2015089889A (ja) | 2015-05-11 |
JP6347723B2 true JP6347723B2 (ja) | 2018-06-27 |
Family
ID=49582540
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014225357A Active JP6347723B2 (ja) | 2013-11-05 | 2014-11-05 | トリス−(2−ヒドロキシエチル)−メチルアンモニウムメチルスルファート脂肪酸エステルの製造方法 |
Country Status (9)
Country | Link |
---|---|
US (1) | US10011806B2 (ja) |
EP (1) | EP2868654B1 (ja) |
JP (1) | JP6347723B2 (ja) |
KR (1) | KR102234671B1 (ja) |
CN (1) | CN104610102B (ja) |
BR (1) | BR102014025172B1 (ja) |
ES (1) | ES2703113T3 (ja) |
MX (2) | MX2019001375A (ja) |
PL (1) | PL2868654T3 (ja) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR102014025172B1 (pt) * | 2013-11-05 | 2020-03-03 | Evonik Degussa Gmbh | Método para fabricação de um éster de ácido graxo de metisulfato de tris-(2-hidroxietil)-metilamônio, e composição ativa de amaciante de roupa |
UA119182C2 (uk) | 2014-10-08 | 2019-05-10 | Евонік Дегусса Гмбх | Активна композиція для пом'якшувача тканини |
CA3014810A1 (en) | 2016-02-26 | 2017-08-31 | Evonik Degussa Gmbh | Amides of aliphatic polyamines and 12-hydroxyoctadecanoic acid and lipase stable thickener compositions |
RU2740475C2 (ru) | 2016-12-06 | 2021-01-14 | Эвоник Корпорейшн | Органофильные глины и буровые растворы, содержащие их |
Family Cites Families (120)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2430140C3 (de) | 1974-06-24 | 1979-10-04 | Rewo Chemische Werke Gmbh, 6497 Steinau | Kationaktive Bis-(2-Acyloxypropyl)ammonium-Salze, Verfahren zu deren Herstellung und Mittel auf deren Basis |
US4234627A (en) | 1977-02-04 | 1980-11-18 | The Procter & Gamble Company | Fabric conditioning compositions |
GB2007734B (en) | 1977-10-22 | 1983-04-07 | Cargo Fleet Chemical Co | Fabric softeners |
FR2440433A1 (fr) | 1978-11-03 | 1980-05-30 | Unilever Nv | Composition d'assouplissement des etoffes et procede pour la preparer |
USRE32713E (en) | 1980-03-17 | 1988-07-12 | Capsule impregnated fabric | |
US4514461A (en) | 1981-08-10 | 1985-04-30 | Woo Yen Kong | Fragrance impregnated fabric |
DE3402146A1 (de) | 1984-01-23 | 1985-07-25 | Henkel KGaA, 4000 Düsseldorf | Neue quartaere ammoniumverbindungen, deren herstellung und verwendung als textilweichmacher |
CS246532B1 (cs) | 1984-08-01 | 1986-10-16 | Dagmar Mikulcova | Avivážní prostředek s antistatickým a změkčujícím účinkem |
US4747880A (en) | 1984-12-12 | 1988-05-31 | S. C. Johnson & Son, Inc. | Dry, granular maintenance product reconstitutable to an aqueous clean and shine product |
DE3608093A1 (de) | 1986-03-12 | 1987-09-17 | Henkel Kgaa | Konfektioniertes textilweichmacher-konzentrat |
DE3710064A1 (de) | 1987-03-27 | 1988-10-06 | Hoechst Ag | Verfahren zur herstellung von quaternaeren esteraminen und ihre verwendung |
ATE84566T1 (de) | 1987-05-01 | 1993-01-15 | Procter & Gamble | Quaternaere isopropylesterammonium-verbindungen als faser- und gewebebehandlungsmittel. |
US4789491A (en) | 1987-08-07 | 1988-12-06 | The Procter & Gamble Company | Method for preparing biodegradable fabric softening compositions |
US4882220A (en) | 1988-02-02 | 1989-11-21 | Kanebo, Ltd. | Fibrous structures having a durable fragrance |
US4954285A (en) | 1988-03-07 | 1990-09-04 | The Procter & Gamble Company | Perfume, particles, especially for use in dryer released fabric softening/antistatic agents |
US5002681A (en) | 1989-03-03 | 1991-03-26 | The Procter & Gamble Company | Jumbo particulate fabric softner composition |
US5137646A (en) | 1989-05-11 | 1992-08-11 | The Procter & Gamble Company | Coated perfume particles in fabric softener or antistatic agents |
ES2021900A6 (es) | 1989-07-17 | 1991-11-16 | Pulcra Sa | Procedimiento de obtencion de tensioactivos cationicos derivados de amonio cuaternario con funcion amino-ester. |
DE3932004A1 (de) | 1989-09-26 | 1991-04-04 | Dursol Fabrik Otto Durst Gmbh | Trocknungsmittel fuer lackoberflaechen |
US5185088A (en) | 1991-04-22 | 1993-02-09 | The Procter & Gamble Company | Granular fabric softener compositions which form aqueous emulsion concentrates |
WO1994007979A1 (en) | 1992-09-28 | 1994-04-14 | The Procter & Gamble Company | Method for using solid particulate fabric softener in automatic dosing dispenser |
DE4243701A1 (de) | 1992-12-23 | 1994-06-30 | Henkel Kgaa | Wäßrige Textilweichmacher-Dispersionen |
WO1994019439A1 (en) | 1993-02-25 | 1994-09-01 | Unilever Plc | Use of fabric softening composition |
US5827451A (en) | 1993-03-17 | 1998-10-27 | Witco Corporation | Microemulsion useful as rinse aid |
DE69406797T2 (de) | 1993-08-06 | 1998-06-10 | Procter & Gamble | Trocken-aktivierte gewebekonditionierungs- und antistatische zusammensetzungen die biologisch abbaubare, ungesättigte verbindungen enthalten |
US5391325A (en) | 1993-09-29 | 1995-02-21 | Exxon Chemical Patents Inc. | Non-toxic biodegradable emulsion compositions for use in automatic car washes |
US5427697A (en) | 1993-12-17 | 1995-06-27 | The Procter & Gamble Company | Clear or translucent, concentrated fabric softener compositions |
US5480567A (en) | 1994-01-14 | 1996-01-02 | Lever Brothers Company, Division Of Conopco, Inc. | Surfactant mixtures for fabric conditioning compositions |
US5869716A (en) * | 1994-03-18 | 1999-02-09 | Henkel Kommanditgesellschaft Auf Aktien | Process for the production of esterquats |
US5474691A (en) | 1994-07-26 | 1995-12-12 | The Procter & Gamble Company | Dryer-added fabric treatment article of manufacture containing antioxidant and sunscreen compounds for sun fade protection of fabrics |
DE4430721A1 (de) | 1994-08-30 | 1996-03-07 | Hoechst Ag | Autoglanztrocknungsmittel |
US5830845A (en) | 1996-03-22 | 1998-11-03 | The Procter & Gamble Company | Concentrated fabric softening composition with good freeze/thaw recovery and highly unsaturated fabric softener compound therefor |
AR006355A1 (es) | 1996-03-22 | 1999-08-25 | Procter & Gamble | Activo suavizante biodegradable y composicion que lo contiene |
US5759990A (en) | 1996-10-21 | 1998-06-02 | The Procter & Gamble Company | Concentrated fabric softening composition with good freeze/thaw recovery and highly unsaturated fabric softener compound therefor |
US5916863A (en) | 1996-05-03 | 1999-06-29 | Akzo Nobel Nv | High di(alkyl fatty ester) quaternary ammonium compound from triethanol amine |
GB9617612D0 (en) | 1996-08-22 | 1996-10-02 | Unilever Plc | Fabric conditioning composition |
CN1238000A (zh) | 1996-09-19 | 1999-12-08 | 普罗格特-甘布尔公司 | 含有阳离子聚合物的浓缩型季铵织物柔软剂组合物 |
DE19708133C1 (de) | 1997-02-28 | 1997-12-11 | Henkel Kgaa | Mittel für die Avivage von Textil- und Keratinfasern sowie die Verwendung von Hydroxycarbonsäureestern zur Herstellung von Avivagemitteln |
US5874396A (en) | 1997-02-28 | 1999-02-23 | The Procter & Gamble Company | Rinse added laundry additive compositions having color care agents |
KR100531564B1 (ko) | 1997-05-01 | 2005-11-29 | 시바 스페셜티 케미칼스 홀딩 인크. | 폴리디오가노실록산을 포함하는 직물 유연제 조성물 |
US6645479B1 (en) | 1997-09-18 | 2003-11-11 | International Flavors & Fragrances Inc. | Targeted delivery of active/bioactive and perfuming compositions |
WO1999035120A1 (en) | 1998-01-09 | 1999-07-15 | Witco Corporation | Novel quaternary ammonium compounds, compositions containing them, and uses thereof |
ZA991635B (en) | 1998-03-02 | 1999-09-02 | Procter & Gamble | Concentrated, stable, translucent or clear, fabric softening compositions. |
GB9816659D0 (en) | 1998-07-30 | 1998-09-30 | Dow Europ Sa | Composition useful for softening, cleaning, and personal care applications and processes for the preparation thereof |
EP0990695A1 (de) | 1998-09-30 | 2000-04-05 | Witco Surfactants GmbH | Weichspülmittel mit farberhaltender Wirkung |
DE19855366A1 (de) * | 1998-12-01 | 2000-06-08 | Witco Surfactants Gmbh | Niedrigkonzentrierte, hochviskose wäßrige Weichspülmittel |
EP1018541A1 (de) | 1999-01-07 | 2000-07-12 | Goldschmidt Rewo GmbH & Co. KG | Klare Weichspülmittelformulierungen |
DE19906367A1 (de) | 1999-02-16 | 2000-08-17 | Clariant Gmbh | Verwendung von Kammpolymeren als Schutzablösepolymere |
US6916781B2 (en) | 1999-03-02 | 2005-07-12 | The Procter & Gamble Company | Concentrated, stable, translucent or clear, fabric softening compositions |
US6458343B1 (en) | 1999-05-07 | 2002-10-01 | Goldschmidt Chemical Corporation | Quaternary compounds, compositions containing them, and uses thereof |
US6995131B1 (en) | 1999-05-10 | 2006-02-07 | The Procter & Gamble Company | Clear or translucent aqueous fabric softener compositions containing high electrolyte and optional phase stabilizer |
US6235914B1 (en) | 1999-08-24 | 2001-05-22 | Goldschmidt Chemical Company | Amine and quaternary ammonium compounds made from ketones and aldehydes, and compositions containing them |
JP2003511572A (ja) | 1999-10-05 | 2003-03-25 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | 布地柔軟剤組成物 |
JP4024438B2 (ja) | 1999-11-01 | 2007-12-19 | 花王株式会社 | 第4級アンモニウム塩組成物 |
DE69924623T2 (de) | 1999-12-07 | 2006-03-09 | The Procter & Gamble Company, Cincinnati | Verfahren zum Schaffen von Tragekomfort |
US6200949B1 (en) | 1999-12-21 | 2001-03-13 | International Flavors And Fragrances Inc. | Process for forming solid phase controllably releasable fragrance-containing consumable articles |
GB0002877D0 (en) | 2000-02-08 | 2000-03-29 | Unilever Plc | Fabric conditioning composition |
FR2806307B1 (fr) | 2000-03-20 | 2002-11-15 | Mane Fils V | Preparation parfumee solide sous forme de microbilles et utilisation de ladite preparation |
MXPA02011555A (es) | 2000-05-24 | 2003-04-25 | Procter & Gamble | Una composicion suavizante de telas que comprende un agente de control del mal olor. |
GB0012958D0 (en) | 2000-05-26 | 2000-07-19 | Unilever Plc | Fabric conditioning composition |
EP1199340B1 (en) | 2000-10-19 | 2005-03-09 | Soft99 Corporation | Paintwork coating composition and coating cloth |
DE60204549T2 (de) | 2001-03-07 | 2006-03-23 | The Procter & Gamble Company, Cincinnati | Weichspülmittelzusammensetzung für die anwendung in anwesenheit von waschmittelrückständen |
GB0106560D0 (en) | 2001-03-16 | 2001-05-02 | Quest Int | Perfume encapsulates |
ES2258506T3 (es) | 2001-12-24 | 2006-09-01 | Cognis Ip Management Gmbh | Composiciones cationicas para la limpieza de superficies duras. |
WO2003061817A1 (de) | 2002-01-24 | 2003-07-31 | Bayer Aktiengesellschaft | Mikrokapseln enthaltende koagulate |
US20030158344A1 (en) | 2002-02-08 | 2003-08-21 | Rodriques Klein A. | Hydrophobe-amine graft copolymer |
US7381697B2 (en) | 2002-04-10 | 2008-06-03 | Ecolab Inc. | Fabric softener composition and methods for manufacturing and using |
US7087572B2 (en) | 2002-04-10 | 2006-08-08 | Ecolab Inc. | Fabric treatment compositions and methods for treating fabric in a dryer |
US20060277689A1 (en) | 2002-04-10 | 2006-12-14 | Hubig Stephan M | Fabric treatment article and methods for using in a dryer |
US7053034B2 (en) | 2002-04-10 | 2006-05-30 | Salvona, Llc | Targeted controlled delivery compositions activated by changes in pH or salt concentration |
US20030216488A1 (en) | 2002-04-18 | 2003-11-20 | The Procter & Gamble Company | Compositions comprising a dispersant and microcapsules containing an active material |
US20030215417A1 (en) | 2002-04-18 | 2003-11-20 | The Procter & Gamble Company | Malodor-controlling compositions comprising odor control agents and microcapsules containing an active material |
US6740631B2 (en) | 2002-04-26 | 2004-05-25 | Adi Shefer | Multi component controlled delivery system for fabric care products |
MXPA04011328A (es) | 2002-05-16 | 2005-02-14 | Procter & Gamble | Composicion que se agrega en el enjuague para el tratamiento de telas y metodos y usos del mismo. |
EP1393706A1 (en) | 2002-08-14 | 2004-03-03 | Quest International B.V. | Fragranced compositions comprising encapsulated material |
US7125835B2 (en) | 2002-10-10 | 2006-10-24 | International Flavors & Fragrances Inc | Encapsulated fragrance chemicals |
US7585824B2 (en) | 2002-10-10 | 2009-09-08 | International Flavors & Fragrances Inc. | Encapsulated fragrance chemicals |
US20040071742A1 (en) | 2002-10-10 | 2004-04-15 | Popplewell Lewis Michael | Encapsulated fragrance chemicals |
US7659238B2 (en) | 2002-11-29 | 2010-02-09 | Ciba Specialty Chemicals Corp. | Fabric softener compositions comprising homo- and/or copolymers |
KR20050099508A (ko) | 2003-02-03 | 2005-10-13 | 시바 스폐셜티 케미칼스 홀딩 인코포레이티드 | 세탁제 및 직물 유연제 제제 |
US7135451B2 (en) | 2003-03-25 | 2006-11-14 | The Procter & Gamble Company | Fabric care compositions comprising cationic starch |
US20050014672A1 (en) | 2003-07-18 | 2005-01-20 | Shoaib Arif | Rinse aid additive and composition containing same |
JP4633722B2 (ja) * | 2003-10-16 | 2011-02-16 | ザ プロクター アンド ギャンブル カンパニー | 特定の小胞透過性を有する小胞を含む水性組成物 |
US7977303B2 (en) | 2004-02-27 | 2011-07-12 | The Procter & Gamble Company | Multiple use fabric conditioning block with indentations |
EP1584674B1 (en) | 2004-03-29 | 2007-08-15 | Clariant Produkte (Deutschland) GmbH | Easy-dispersible concentrate ester quat compositions |
US7704940B2 (en) | 2004-04-09 | 2010-04-27 | The Sun Products Corporation | Granulate for use in a cleaning product and process for its manufacture |
EP1838827A1 (en) | 2004-10-18 | 2007-10-03 | The Procter and Gamble Company | Concentrated fabric softener active compositions |
DE102005020551A1 (de) | 2005-05-03 | 2006-11-09 | Degussa Ag | Feste, redispergierbare Emulsion |
US20060252669A1 (en) | 2005-05-06 | 2006-11-09 | Marija Heibel | Fabric care composition comprising polymer encapsulated fabric or skin beneficiating ingredient |
JP4757711B2 (ja) * | 2005-06-01 | 2011-08-24 | 花王株式会社 | 透明又は半透明の液体柔軟剤組成物 |
US20070054835A1 (en) | 2005-08-31 | 2007-03-08 | The Procter & Gamble Company | Concentrated fabric softener active compositions |
DE602006004426D1 (de) | 2005-09-06 | 2009-02-05 | Clariant Brazil S A | Stabile wässrige Esterquat-Zusammensetztungen |
DE602006021041D1 (de) | 2005-09-22 | 2011-05-12 | Procter & Gamble | Weichspülerzusammensetzung mit verringerter stoffeinfärbung |
US7572761B2 (en) | 2005-11-14 | 2009-08-11 | Evonik Degussa Gmbh | Process for cleaning and softening fabrics |
WO2007092020A1 (en) * | 2006-02-10 | 2007-08-16 | Stepan Company | Fabric conditioning active compositions |
WO2007099505A1 (en) | 2006-02-28 | 2007-09-07 | The Procter & Gamble Company | Fabric care compositions comprising cationic starch |
ES2294923B1 (es) | 2006-03-31 | 2009-02-16 | Kao Corporation, S.A. | Composicion para el enjuague y secado de vehiculos. |
EP1849855A1 (de) | 2006-04-27 | 2007-10-31 | Degussa GmbH | Thixotrope Weichspülmittel |
EP1876223B1 (en) | 2006-07-06 | 2009-02-18 | Clariant (Brazil) S.A. | Concentrated esterquat composition |
WO2008021892A1 (en) | 2006-08-08 | 2008-02-21 | The Procter & Gamble Company | Fabric enhancers comprising nano-sized lamellar vesicle |
ES2479116T3 (es) | 2007-02-28 | 2014-07-23 | Unilever N.V. | Composiciones de tratamiento de telas, su fabricación y uso |
US20080242584A1 (en) | 2007-04-02 | 2008-10-02 | Errol Hoffman Wahl | Fabric care composition |
US20110237667A1 (en) | 2007-08-06 | 2011-09-29 | Clariant Finance (Bvi) Limited | Compositions Containing Diethanol Amine Esterquats |
MY151001A (en) * | 2007-12-28 | 2014-03-31 | Malaysian Palm Oil Board Mpob | Fatty acid compositions of methyl ester for esterquats production suitable for fabric softener |
US8080513B2 (en) | 2008-01-11 | 2011-12-20 | The Procter & Gamble Company | Method of shipping and preparing laundry actives |
US8361953B2 (en) | 2008-02-08 | 2013-01-29 | Evonik Goldschmidt Corporation | Rinse aid compositions with improved characteristics |
ES2647570T3 (es) | 2009-11-06 | 2017-12-22 | The Procter & Gamble Company | Cápsulas de alta eficacia que comprenden agente beneficioso |
JP5431619B2 (ja) * | 2010-04-01 | 2014-03-05 | ザ プロクター アンド ギャンブル カンパニー | 柔軟仕上げ剤 |
MY160707A (en) | 2010-04-01 | 2017-03-15 | Evonik Degussa Gmbh | Fabric softener active composition |
US8183199B2 (en) | 2010-04-01 | 2012-05-22 | The Procter & Gamble Company | Heat stable fabric softener |
US20110239377A1 (en) | 2010-04-01 | 2011-10-06 | Renae Dianna Fossum | Heat Stable Fabric Softener |
ES2536849T3 (es) | 2010-04-01 | 2015-05-29 | Evonik Degussa Gmbh | Composición de sustancia activa suavizante de tejidos |
MX2012012340A (es) | 2010-04-28 | 2012-11-21 | Evonik Degussa Gmbh | Composicion suavizante de telas. |
US8507425B2 (en) | 2010-06-29 | 2013-08-13 | Evonik Degussa Gmbh | Particulate fabric softener comprising ethylenediamine fatty acid amides and method of making |
EP2632893B1 (en) * | 2010-10-25 | 2018-12-05 | Stepan Company | Esteramines and derivatives from natural oil metathesis |
JP5897321B2 (ja) * | 2011-12-26 | 2016-03-30 | 花王株式会社 | 袋状柔軟剤物品 |
WO2013113453A1 (en) | 2012-01-30 | 2013-08-08 | Evonik Industries Ag | Fabric softener active composition |
JP6233303B2 (ja) * | 2012-03-30 | 2017-11-22 | 三菱ケミカル株式会社 | エポキシ化合物の製造方法及びエポキシ化反応用触媒組成物 |
DK2847307T3 (en) * | 2012-05-07 | 2016-07-25 | Evonik Degussa Gmbh | ACTIVE SOFT COMPOSITION FOR TEXTILES AND PROCEDURES FOR MANUFACTURING THEREOF |
BR102014025172B1 (pt) * | 2013-11-05 | 2020-03-03 | Evonik Degussa Gmbh | Método para fabricação de um éster de ácido graxo de metisulfato de tris-(2-hidroxietil)-metilamônio, e composição ativa de amaciante de roupa |
-
2014
- 2014-10-09 BR BR102014025172-3A patent/BR102014025172B1/pt active IP Right Grant
- 2014-10-10 CN CN201410531796.3A patent/CN104610102B/zh active Active
- 2014-10-15 PL PL14188997T patent/PL2868654T3/pl unknown
- 2014-10-15 EP EP14188997.2A patent/EP2868654B1/en active Active
- 2014-10-15 ES ES14188997T patent/ES2703113T3/es active Active
- 2014-10-17 MX MX2019001375A patent/MX2019001375A/es unknown
- 2014-10-17 MX MX2014012611A patent/MX363849B/es active IP Right Grant
- 2014-10-31 KR KR1020140149959A patent/KR102234671B1/ko active IP Right Grant
- 2014-11-03 US US14/531,507 patent/US10011806B2/en active Active
- 2014-11-05 JP JP2014225357A patent/JP6347723B2/ja active Active
Also Published As
Publication number | Publication date |
---|---|
BR102014025172A2 (pt) | 2015-09-29 |
MX2014012611A (es) | 2016-06-30 |
US10011806B2 (en) | 2018-07-03 |
BR102014025172B1 (pt) | 2020-03-03 |
PL2868654T4 (pl) | 2019-05-31 |
CN104610102A (zh) | 2015-05-13 |
MX2019001375A (es) | 2019-06-24 |
PL2868654T3 (pl) | 2019-05-31 |
KR20150051889A (ko) | 2015-05-13 |
US20150126431A1 (en) | 2015-05-07 |
JP2015089889A (ja) | 2015-05-11 |
CN104610102B (zh) | 2019-07-02 |
EP2868654A1 (en) | 2015-05-06 |
MX363849B (es) | 2019-04-05 |
KR102234671B1 (ko) | 2021-04-02 |
EP2868654B1 (en) | 2018-09-19 |
ES2703113T3 (es) | 2019-03-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5570651B2 (ja) | 織物柔軟剤活性組成物 | |
JP5460919B2 (ja) | 織物柔軟剤活性組成物 | |
JP6548726B2 (ja) | 布地柔軟剤活性組成物 | |
JP5992605B2 (ja) | 織物柔軟剤活性組成物およびその製造方法 | |
JP6347723B2 (ja) | トリス−(2−ヒドロキシエチル)−メチルアンモニウムメチルスルファート脂肪酸エステルの製造方法 | |
JP4271562B2 (ja) | トリエステルカチオン組成物とその製造法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A711 Effective date: 20151222 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20170426 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20170913 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20170925 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20171225 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20180507 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20180529 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6347723 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
S533 | Written request for registration of change of name |
Free format text: JAPANESE INTERMEDIATE CODE: R313533 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |