SK109297A3 - Synthesis of bleach activators - Google Patents
Synthesis of bleach activators Download PDFInfo
- Publication number
- SK109297A3 SK109297A3 SK1092-97A SK109297A SK109297A3 SK 109297 A3 SK109297 A3 SK 109297A3 SK 109297 A SK109297 A SK 109297A SK 109297 A3 SK109297 A3 SK 109297A3
- Authority
- SK
- Slovakia
- Prior art keywords
- acid halide
- phenol sulfonate
- acid
- amino acid
- nonanoyl
- Prior art date
Links
- 239000012190 activator Substances 0.000 title abstract description 10
- 238000003786 synthesis reaction Methods 0.000 title abstract description 8
- 230000015572 biosynthetic process Effects 0.000 title abstract description 7
- 239000007844 bleaching agent Substances 0.000 title abstract description 6
- 229940044652 phenolsulfonate Drugs 0.000 claims abstract description 20
- 150000002148 esters Chemical class 0.000 claims abstract description 15
- SBLCUTIOHNPTHL-UHFFFAOYSA-N 6-(nonanoylamino)hexanoic acid Chemical compound CCCCCCCCC(=O)NCCCCCC(O)=O SBLCUTIOHNPTHL-UHFFFAOYSA-N 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- -1 hydrocarbon esters Chemical class 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 150000001413 amino acids Chemical class 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims 2
- XDEJLUXQQIEFNG-UHFFFAOYSA-N 2-nonylhexanedioic acid Chemical compound CCCCCCCCCC(C(O)=O)CCCC(O)=O XDEJLUXQQIEFNG-UHFFFAOYSA-N 0.000 claims 1
- 101100520660 Drosophila melanogaster Poc1 gene Proteins 0.000 claims 1
- 101100520662 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) PBA1 gene Proteins 0.000 claims 1
- 230000002051 biphasic effect Effects 0.000 claims 1
- 150000003842 bromide salts Chemical class 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract description 10
- 159000000000 sodium salts Chemical class 0.000 abstract description 3
- 125000005236 alkanoylamino group Chemical group 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 2
- FEPBITJSIHRMRT-UHFFFAOYSA-N 4-hydroxybenzenesulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C=C1 FEPBITJSIHRMRT-UHFFFAOYSA-N 0.000 abstract 1
- 235000011037 adipic acid Nutrition 0.000 abstract 1
- 239000001361 adipic acid Substances 0.000 abstract 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 238000004061 bleaching Methods 0.000 description 7
- 239000003599 detergent Substances 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229940087596 sodium phenolsulfonate Drugs 0.000 description 6
- BLXAGSNYHSQSRC-UHFFFAOYSA-M sodium;2-hydroxybenzenesulfonate Chemical compound [Na+].OC1=CC=CC=C1S([O-])(=O)=O BLXAGSNYHSQSRC-UHFFFAOYSA-M 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 238000003436 Schotten-Baumann reaction Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- JQSMFSPOCAZNQP-UHFFFAOYSA-N 6-(nonylamino)-6-oxohexanoic acid Chemical compound CCCCCCCCCNC(=O)CCCCC(O)=O JQSMFSPOCAZNQP-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- YOFDKNMBODQGDQ-UHFFFAOYSA-N 6-(nonanoylamino)hexanoyl chloride Chemical compound CCCCCCCCC(=O)NCCCCCC(Cl)=O YOFDKNMBODQGDQ-UHFFFAOYSA-N 0.000 description 2
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229940045872 sodium percarbonate Drugs 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- OQUFOZNPBIIJTN-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;sodium Chemical compound [Na].OC(=O)CC(O)(C(O)=O)CC(O)=O OQUFOZNPBIIJTN-UHFFFAOYSA-N 0.000 description 1
- XSVSPKKXQGNHMD-UHFFFAOYSA-N 5-bromo-3-methyl-1,2-thiazole Chemical compound CC=1C=C(Br)SN=1 XSVSPKKXQGNHMD-UHFFFAOYSA-N 0.000 description 1
- 102000013142 Amylases Human genes 0.000 description 1
- 108010065511 Amylases Proteins 0.000 description 1
- 108010059892 Cellulase Proteins 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229960002684 aminocaproic acid Drugs 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012455 biphasic mixture Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229940106157 cellulase Drugs 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 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
- VTIIJXUACCWYHX-UHFFFAOYSA-L disodium;carboxylatooxy carbonate Chemical compound [Na+].[Na+].[O-]C(=O)OOC([O-])=O VTIIJXUACCWYHX-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 229960003330 pentetic acid Drugs 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical compound [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- TTZZRXVYJJWRGL-UHFFFAOYSA-K trisodium;hydrogen carbonate;sulfate Chemical compound [Na+].[Na+].[Na+].OC([O-])=O.[O-]S([O-])(=O)=O TTZZRXVYJJWRGL-UHFFFAOYSA-K 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- 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
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
-
- 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
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/404,654 US5523434A (en) | 1995-03-15 | 1995-03-15 | Synthesis of bleach activators |
| PCT/US1996/002887 WO1996028417A1 (en) | 1995-03-15 | 1996-03-04 | Synthesis of bleach activators |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK109297A3 true SK109297A3 (en) | 1998-08-05 |
Family
ID=23600487
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1092-97A SK109297A3 (en) | 1995-03-15 | 1996-03-04 | Synthesis of bleach activators |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US5523434A (hu) |
| EP (1) | EP0815075B1 (hu) |
| AT (1) | ATE198322T1 (hu) |
| AU (1) | AU5357296A (hu) |
| BR (1) | BR9607470A (hu) |
| CA (1) | CA2214117C (hu) |
| CZ (1) | CZ291279B6 (hu) |
| DE (1) | DE69611356T2 (hu) |
| DK (1) | DK0815075T3 (hu) |
| EG (1) | EG20957A (hu) |
| ES (1) | ES2153099T3 (hu) |
| GR (1) | GR3035214T3 (hu) |
| HU (1) | HUP9801398A3 (hu) |
| IL (1) | IL117394A (hu) |
| MA (1) | MA23825A1 (hu) |
| NO (1) | NO308357B1 (hu) |
| PL (1) | PL322212A1 (hu) |
| PT (1) | PT815075E (hu) |
| RU (1) | RU2158256C2 (hu) |
| SK (1) | SK109297A3 (hu) |
| TR (1) | TR199700951T1 (hu) |
| TW (1) | TW330196B (hu) |
| WO (1) | WO1996028417A1 (hu) |
| ZA (1) | ZA962057B (hu) |
Families Citing this family (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69716761T2 (de) | 1996-12-17 | 2003-07-03 | Procter & Gamble | Verfahren zur herstellung von n-(alkanoyl)aminoalkanoyloxybenzolsulfonaten |
| JP2001515062A (ja) | 1997-08-20 | 2001-09-18 | ザ、プロクター、エンド、ギャンブル、カンパニー | アミド酸フェニルエステルスルホネートの調製方法および／または精製方法 |
| MA25044A1 (fr) | 1997-10-23 | 2000-10-01 | Procter & Gamble | Compositions de lavage contenant des variants de proteases multisubstituees. |
| GB9726247D0 (en) * | 1997-12-11 | 1998-02-11 | Ass Octel | Preparation of esters |
| GB9726246D0 (en) * | 1997-12-11 | 1998-02-11 | Ass Octel | Preparation of esters |
| US6420331B1 (en) * | 1998-06-10 | 2002-07-16 | Procter & Gamble Company | Detergent compositions comprising a mannanase and a bleach system |
| EP0982291B1 (de) * | 1998-07-31 | 2003-03-26 | Clariant GmbH | Verfahren zur Herstellung von Amidosäurephenylestern |
| US6583095B1 (en) | 1998-11-20 | 2003-06-24 | Procter & Gamble Company | Synthesis of bleach activators |
| DE19900939C2 (de) * | 1999-01-13 | 2001-06-07 | Clariant Gmbh | Verfahren zur Herstellung von Amidosäurephenylestern |
| CA2378897C (en) | 1999-07-16 | 2009-10-06 | The Procter & Gamble Company | Laundry detergent compositions comprising zwitterionic polyamines and mid-chain branched surfactants |
| US6448431B1 (en) * | 1999-09-13 | 2002-09-10 | Eastman Chemical Company | Production of aryl carboxylate esters |
| US6812198B2 (en) * | 1999-11-09 | 2004-11-02 | The Procter & Gamble Company | Laundry detergent compositions comprising hydrophobically modified polyamines |
| MXPA02004615A (es) | 1999-11-09 | 2002-09-02 | Procter & Gamble | Composiciones detergentes de lavar ropa que comprenden poliaminas hidrofobamente modificadas. |
| US6696401B1 (en) * | 1999-11-09 | 2004-02-24 | The Procter & Gamble Company | Laundry detergent compositions comprising zwitterionic polyamines |
| DE19956863A1 (de) * | 1999-11-25 | 2001-06-21 | Axiva Gmbh | Verfahren zur Isolierung von Amidosäurephenylestersulfonaten aus Wasser-Lösungsmittel-Gemischen |
| DE19956862A1 (de) | 1999-11-25 | 2001-06-21 | Axiva Gmbh | Verfahren zur Gewinnung und Reinigung substituierter Benzolsulfonate |
| US6498124B2 (en) | 2000-06-02 | 2002-12-24 | Eastman Chemical Company | Isolation of phenyl ester salts from mixtures comprising sulfolane |
| US6660712B2 (en) | 2000-06-02 | 2003-12-09 | Dale Elbert Van Sickle | Stabilization of amido acids with antioxidants |
| AU2001268171A1 (en) | 2000-06-02 | 2001-12-11 | Eastman Chemical Company | Process for recycling amido-carboxylic acid esters into amido-carboxylic acids |
| EP1286958B1 (en) | 2000-06-02 | 2005-01-12 | Eastman Chemical Company | Improved purification of phenyl ester salts |
| US6500973B2 (en) | 2000-06-02 | 2002-12-31 | Eastman Chemical Company | Extractive solution crystallization of chemical compounds |
| GB2366564A (en) | 2000-08-30 | 2002-03-13 | Procter & Gamble | Preparation of Esters and Amides |
| DE60134760D1 (de) | 2000-10-27 | 2008-08-21 | Procter & Gamble | Stabilisierte flüssige zusammensetzungen |
| DE10139663A1 (de) * | 2001-08-11 | 2003-02-20 | Clariant Gmbh | Verfahren zur Herstellung von Acyloxybenzolsulfonaten |
| DE10145223A1 (de) | 2001-09-13 | 2003-04-03 | Basf Ag | Verfahren zur Herstellung von meso-Zeaxanthin |
| DE10233827A1 (de) * | 2002-07-25 | 2004-02-12 | Clariant Gmbh | Verfahren zur Herstellung von Acyloxybenzolsulfonaten |
| DE10300981A1 (de) * | 2003-01-14 | 2004-07-22 | Clariant Gmbh | Verfahren zur Herstellung von Acyloxybenzolsulfonaten |
| US20080177089A1 (en) | 2007-01-19 | 2008-07-24 | Eugene Steven Sadlowski | Novel whitening agents for cellulosic substrates |
| US8558051B2 (en) * | 2007-07-18 | 2013-10-15 | The Procter & Gamble Company | Disposable absorbent article having odor control system |
| US8198503B2 (en) * | 2007-11-19 | 2012-06-12 | The Procter & Gamble Company | Disposable absorbent articles comprising odor controlling materials |
| US8293697B2 (en) | 2009-03-18 | 2012-10-23 | The Procter & Gamble Company | Structured fluid detergent compositions comprising dibenzylidene sorbitol acetal derivatives |
| US8153574B2 (en) | 2009-03-18 | 2012-04-10 | The Procter & Gamble Company | Structured fluid detergent compositions comprising dibenzylidene polyol acetal derivatives and detersive enzymes |
| WO2011112887A1 (en) | 2010-03-12 | 2011-09-15 | The Procter & Gamble Company | Di-amido gellant for use in consumer product compositions |
| CA2792767C (en) | 2010-03-12 | 2014-07-08 | The Procter & Gamble Company | Ph tuneable amido-gellant for use in consumer product compositions |
| US20110240510A1 (en) | 2010-04-06 | 2011-10-06 | Johan Maurice Theo De Poortere | Optimized release of bleaching systems in laundry detergents |
| JP5698348B2 (ja) | 2010-05-18 | 2015-04-08 | ミリケン・アンド・カンパニーＭｉｌｌｉｋｅｎ ＆ Ｃｏｍｐａｎｙ | 蛍光増白剤およびそれを含む組成物 |
| BR112012029188B1 (pt) | 2010-05-18 | 2020-12-08 | Milliken & Company | compostos clareadores óticos e composições compreendendo os mesmos |
| US8476216B2 (en) | 2010-05-28 | 2013-07-02 | Milliken & Company | Colored speckles having delayed release properties |
| US8715368B2 (en) | 2010-11-12 | 2014-05-06 | The Procter & Gamble Company | Thiophene azo dyes and laundry care compositions containing the same |
| JP2014512257A (ja) | 2011-02-25 | 2014-05-22 | ミリケン・アンド・カンパニー | カプセルおよびそれを含む組成物 |
| US20130029895A1 (en) | 2011-07-27 | 2013-01-31 | Jean-Luc Phillippe Bettiol | Multiphase liquid detergent composition |
| US20130303427A1 (en) | 2011-09-13 | 2013-11-14 | Susana Fernandez Prieto | MICROCAPSULE COMPOSITIONS COMPRISING pH TUNEABLE DI-AMIDO GELLANTS |
| US9777250B2 (en) | 2015-10-13 | 2017-10-03 | Milliken & Company | Whitening agents for cellulosic substrates |
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| US11518963B2 (en) | 2018-10-18 | 2022-12-06 | Milliken & Company | Polyethyleneimine compounds containing N-halamine and derivatives thereof |
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| CN110872246A (zh) * | 2019-12-02 | 2020-03-10 | 山东益丰生化环保股份有限公司 | 一种高含量季戊四醇四(3-巯基丙酸)酯的制备方法 |
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| US11351106B2 (en) | 2020-09-14 | 2022-06-07 | Milliken & Company | Oxidative hair cream composition containing thiophene azo colorant |
| US20220079862A1 (en) | 2020-09-14 | 2022-03-17 | Milliken & Company | Hair care composition containing polymeric colorant |
| WO2022197295A1 (en) | 2021-03-17 | 2022-09-22 | Milliken & Company | Polymeric colorants with reduced staining |
| WO2023038971A1 (en) | 2021-09-09 | 2023-03-16 | Milliken & Company | Phenolic compositions for malodor reduction |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4634551A (en) * | 1985-06-03 | 1987-01-06 | Procter & Gamble Company | Bleaching compounds and compositions comprising fatty peroxyacids salts thereof and precursors therefor having amide moieties in the fatty chain |
| US4852989A (en) * | 1987-05-08 | 1989-08-01 | The Procter & Gamble Company | Bleaching compounds and compositions comprising fatty peroxyacids salts thereof and precursors therefor having amide moieties in the fatty chain |
| GB8712909D0 (en) * | 1987-06-02 | 1987-07-08 | Interox Chemicals Ltd | Preparation of esters |
| CA2161212A1 (en) * | 1993-05-20 | 1994-12-08 | Alan David Willey | Bleaching compounds comprising peroxyacid activators used with enzymes |
-
1995
- 1995-03-15 US US08/404,654 patent/US5523434A/en not_active Expired - Fee Related
-
1996
- 1996-03-04 PT PT96910359T patent/PT815075E/pt unknown
- 1996-03-04 DK DK96910359T patent/DK0815075T3/da active
- 1996-03-04 AT AT96910359T patent/ATE198322T1/de not_active IP Right Cessation
- 1996-03-04 CA CA002214117A patent/CA2214117C/en not_active Expired - Fee Related
- 1996-03-04 DE DE69611356T patent/DE69611356T2/de not_active Expired - Fee Related
- 1996-03-04 AU AU53572/96A patent/AU5357296A/en not_active Abandoned
- 1996-03-04 PL PL96322212A patent/PL322212A1/xx unknown
- 1996-03-04 HU HU9801398A patent/HUP9801398A3/hu unknown
- 1996-03-04 CZ CZ19972875A patent/CZ291279B6/cs not_active IP Right Cessation
- 1996-03-04 ES ES96910359T patent/ES2153099T3/es not_active Expired - Lifetime
- 1996-03-04 TR TR97/00951T patent/TR199700951T1/xx unknown
- 1996-03-04 SK SK1092-97A patent/SK109297A3/sk unknown
- 1996-03-04 EP EP96910359A patent/EP0815075B1/en not_active Expired - Lifetime
- 1996-03-04 RU RU97117099/04A patent/RU2158256C2/ru active
- 1996-03-04 WO PCT/US1996/002887 patent/WO1996028417A1/en active IP Right Grant
- 1996-03-04 BR BR9607470A patent/BR9607470A/pt not_active Application Discontinuation
- 1996-03-07 IL IL11739496A patent/IL117394A/xx active IP Right Grant
- 1996-03-13 EG EG22196A patent/EG20957A/xx active
- 1996-03-14 ZA ZA962057A patent/ZA962057B/xx unknown
- 1996-03-14 MA MA24182A patent/MA23825A1/fr unknown
- 1996-05-02 TW TW085105280A patent/TW330196B/zh active
-
1997
- 1997-09-05 NO NO974095A patent/NO308357B1/no unknown
-
2001
- 2001-01-11 GR GR20010400028T patent/GR3035214T3/el not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IL117394A0 (en) | 1996-07-23 |
| NO308357B1 (no) | 2000-09-04 |
| CZ291279B6 (cs) | 2003-01-15 |
| CA2214117A1 (en) | 1996-09-19 |
| CA2214117C (en) | 2002-08-13 |
| GR3035214T3 (en) | 2001-04-30 |
| TR199700951T1 (xx) | 1998-01-21 |
| IL117394A (en) | 2000-08-31 |
| AU5357296A (en) | 1996-10-02 |
| EP0815075B1 (en) | 2000-12-27 |
| DE69611356D1 (de) | 2001-02-01 |
| US5523434A (en) | 1996-06-04 |
| PT815075E (pt) | 2001-04-30 |
| PL322212A1 (en) | 1998-01-19 |
| EP0815075A1 (en) | 1998-01-07 |
| MA23825A1 (fr) | 1996-10-01 |
| ATE198322T1 (de) | 2001-01-15 |
| NO974095L (no) | 1997-09-05 |
| MX9707037A (es) | 1997-11-29 |
| HUP9801398A3 (en) | 2000-03-28 |
| NO974095D0 (no) | 1997-09-05 |
| TW330196B (en) | 1998-04-21 |
| DK0815075T3 (da) | 2001-01-29 |
| HUP9801398A2 (hu) | 1998-12-28 |
| BR9607470A (pt) | 1997-12-23 |
| EG20957A (en) | 2000-07-30 |
| WO1996028417A1 (en) | 1996-09-19 |
| DE69611356T2 (de) | 2001-07-19 |
| ES2153099T3 (es) | 2001-02-16 |
| ZA962057B (en) | 1996-11-27 |
| CZ287597A3 (cs) | 1998-02-18 |
| RU2158256C2 (ru) | 2000-10-27 |
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