DE69921352T2 - Verfahren zur herstellung von mono-langkettigen aminoxid tensiden mit niedrigem nitrit-, nitrosamin- und restperoxid-gehalt - Google Patents
Verfahren zur herstellung von mono-langkettigen aminoxid tensiden mit niedrigem nitrit-, nitrosamin- und restperoxid-gehalt Download PDFInfo
- Publication number
- DE69921352T2 DE69921352T2 DE69921352T DE69921352T DE69921352T2 DE 69921352 T2 DE69921352 T2 DE 69921352T2 DE 69921352 T DE69921352 T DE 69921352T DE 69921352 T DE69921352 T DE 69921352T DE 69921352 T2 DE69921352 T2 DE 69921352T2
- Authority
- DE
- Germany
- Prior art keywords
- amine
- bicarbonate
- amine oxide
- hydrogen peroxide
- content
- 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.)
- Expired - Lifetime
Links
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims description 35
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 title abstract description 7
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 title abstract description 5
- 238000004519 manufacturing process Methods 0.000 title description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 title 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 70
- 150000001412 amines Chemical class 0.000 claims abstract description 59
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims abstract description 23
- -1 Mono-long chain amine Chemical class 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 239000000463 material Substances 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 239000003599 detergent Substances 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 5
- 230000001590 oxidative effect Effects 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 102000004190 Enzymes Human genes 0.000 claims description 3
- 108090000790 Enzymes Proteins 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000002243 precursor Substances 0.000 claims description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 230000035484 reaction time Effects 0.000 description 8
- 150000002826 nitrites Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 150000004005 nitrosamines Chemical class 0.000 description 4
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 2
- 239000001099 ammonium carbonate Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000004851 dishwashing Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- GPCKFIWBUTWTDH-UHFFFAOYSA-N pentane-3,3-diamine Chemical compound CCC(N)(N)CC GPCKFIWBUTWTDH-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C291/00—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
- C07C291/02—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds
- C07C291/04—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds containing amino-oxide bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US200391 | 1998-11-24 | ||
| US09/200,391 US6294514B1 (en) | 1998-11-24 | 1998-11-24 | Process for preparing mono-long chain amine oxide surfactants with low nitrite, nitrosamine and low residual peroxide |
| PCT/US1999/027315 WO2000031026A1 (en) | 1998-11-24 | 1999-11-18 | Process for preparing mono-long chain amine oxide surfactans with low nitrite, nitrosamine and low residual peroxide level |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69921352D1 DE69921352D1 (de) | 2004-11-25 |
| DE69921352T2 true DE69921352T2 (de) | 2005-10-13 |
Family
ID=22741525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69921352T Expired - Lifetime DE69921352T2 (de) | 1998-11-24 | 1999-11-18 | Verfahren zur herstellung von mono-langkettigen aminoxid tensiden mit niedrigem nitrit-, nitrosamin- und restperoxid-gehalt |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6294514B1 (enExample) |
| EP (1) | EP1133469B1 (enExample) |
| JP (1) | JP4334772B2 (enExample) |
| CN (1) | CN1183105C (enExample) |
| AT (1) | ATE280150T1 (enExample) |
| CA (1) | CA2348920C (enExample) |
| DE (1) | DE69921352T2 (enExample) |
| ES (1) | ES2228140T3 (enExample) |
| WO (1) | WO2000031026A1 (enExample) |
Families Citing this family (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101056844A (zh) * | 2004-11-15 | 2007-10-17 | 宝洁公司 | 用于制备长链内脂肪叔胺的方法 |
| CN101528664A (zh) * | 2004-11-15 | 2009-09-09 | 宝洁公司 | 制备长链内脂肪族叔胺的方法 |
| GB0510989D0 (en) * | 2005-05-28 | 2005-07-06 | Unilever Plc | Detergent compositions and their use |
| ES2529815T3 (es) | 2005-10-12 | 2015-02-25 | The Procter & Gamble Company | Uso y producción de metaloproteasa neutra estable en el almacenamiento |
| US20070191256A1 (en) | 2006-02-10 | 2007-08-16 | Fossum Renae D | Fabric care compositions comprising formaldehyde scavengers |
| EP1988990A4 (en) * | 2006-02-28 | 2009-08-19 | Appleton Paper Inc | CARE WITH RELEASE PARTICLES |
| CA2658303A1 (en) * | 2006-08-01 | 2008-02-07 | The Procter & Gamble Company | Receiving apparatus |
| DE602007011272D1 (de) * | 2006-08-01 | 2011-01-27 | Procter & Gamble | Pflegemittel mit freisetzungspartikel |
| EP2426199A3 (en) | 2006-10-20 | 2012-08-22 | Danisco US Inc. | Polyol oxidases |
| ES2428729T3 (es) | 2006-11-22 | 2013-11-11 | The Procter & Gamble Company | Partícula liberadora que contiene un agente beneficioso |
| CN101617036A (zh) * | 2007-02-15 | 2009-12-30 | 宝洁公司 | 有益剂递送组合物 |
| JP2010528161A (ja) * | 2007-06-05 | 2010-08-19 | ザ プロクター アンド ギャンブル カンパニー | 香料システム |
| JP5978480B2 (ja) | 2007-06-11 | 2016-08-24 | エンカプシス エルエルシー | 有益剤含有デリバリー粒子 |
| US20090048136A1 (en) * | 2007-08-15 | 2009-02-19 | Mcdonald Hugh C | Kappa-carrageenase and kappa-carrageenase-containing compositions |
| JP2011502506A (ja) | 2007-11-01 | 2011-01-27 | ダニスコ・ユーエス・インク | サーモリシン及びその変異体の生成及び液体洗剤での使用 |
| HUE035721T2 (hu) * | 2008-02-15 | 2018-08-28 | Procter & Gamble | Vivõrészecske |
| AR072601A1 (es) * | 2008-07-30 | 2010-09-08 | Appleton Paper Inc | Particulas de entrega |
| MX2011004847A (es) * | 2008-11-07 | 2011-05-30 | Procter & Gamble | Agente benefico que contiene particulas de suministro. |
| MX2011004803A (es) | 2008-11-11 | 2011-06-16 | Danisco Inc | Composiciones y metodos que comprenden una variante de subtilisina. |
| MX2011004801A (es) | 2008-11-11 | 2011-06-16 | Danisco Inc | Composiciones y metodos que comprenden una variante de subtilisina. |
| CA2744033A1 (en) * | 2008-12-01 | 2010-06-10 | The Procter & Gamble Company | Perfume systems |
| US20100190673A1 (en) * | 2009-01-29 | 2010-07-29 | Johan Smets | Encapsulates |
| US20100190674A1 (en) * | 2009-01-29 | 2010-07-29 | Johan Smets | Encapsulates |
| CA2658247A1 (en) | 2009-03-16 | 2009-06-03 | The Procter & Gamble Company | Fabric care products |
| WO2011056904A1 (en) * | 2009-11-06 | 2011-05-12 | The Procter & Gamble Company | High efficiency particle comprising benefit agent |
| DK3190183T3 (da) | 2009-12-09 | 2019-10-14 | Danisco Us Inc | Sammensætninger og fremgangsmåder omfattende proteasevarianter |
| CN102712882A (zh) * | 2009-12-18 | 2012-10-03 | 宝洁公司 | 包含包封物的组合物以及用于制备它们的方法 |
| CA2780653C (en) | 2009-12-18 | 2014-05-13 | The Procter & Gamble Company | Encapsulates |
| RU2557239C2 (ru) | 2010-04-01 | 2015-07-20 | Дзе Проктер Энд Гэмбл Компани | Органосиликоны |
| WO2011130222A2 (en) | 2010-04-15 | 2011-10-20 | Danisco Us Inc. | Compositions and methods comprising variant proteases |
| US20110269657A1 (en) | 2010-04-28 | 2011-11-03 | Jiten Odhavji Dihora | Delivery particles |
| US9186642B2 (en) | 2010-04-28 | 2015-11-17 | The Procter & Gamble Company | Delivery particle |
| US9993793B2 (en) | 2010-04-28 | 2018-06-12 | The Procter & Gamble Company | Delivery particles |
| MX339810B (es) | 2010-05-06 | 2016-06-09 | The Procter & Gamble Company * | Productos de consumo con variantes de la proteasa. |
| EP2569408A1 (en) | 2010-05-12 | 2013-03-20 | The Procter and Gamble Company | Care polymers |
| WO2012138696A2 (en) | 2011-04-07 | 2012-10-11 | The Procter & Gamble Company | Shampoo compositions with increased deposition of polyacrylate microcapsules |
| WO2012138710A2 (en) | 2011-04-07 | 2012-10-11 | The Procter & Gamble Company | Personal cleansing compositions with increased deposition of polyacrylate microcapsules |
| CN103458871B (zh) | 2011-04-07 | 2015-05-13 | 宝洁公司 | 具有增强的聚丙烯酸酯微胶囊的沉积的调理剂组合物 |
| TR201901382T4 (tr) | 2011-05-05 | 2019-02-21 | Danisco Inc | Serin proteaz varyantlarını içeren bileşimler ve yöntemler. |
| WO2012151480A2 (en) | 2011-05-05 | 2012-11-08 | The Procter & Gamble Company | Compositions and methods comprising serine protease variants |
| US20140187468A1 (en) | 2011-08-31 | 2014-07-03 | Danisco Us Inc. | Compositions and Methods Comprising a Lipolytic Enzyme Variant |
| RU2610439C2 (ru) | 2011-11-11 | 2017-02-10 | Басф Се | Самоэмульгируемые полиолефиновые композиции |
| US20130118531A1 (en) | 2011-11-11 | 2013-05-16 | The Procter & Gamble Company | Emulsions containing polymeric cationic emulsifiers, substance and process |
| WO2013096653A1 (en) | 2011-12-22 | 2013-06-27 | Danisco Us Inc. | Compositions and methods comprising a lipolytic enzyme variant |
| EP3842531A1 (en) | 2012-10-12 | 2021-06-30 | Danisco US Inc. | Compositions and method comprising a lipolytic enzyme variant |
| KR20150082502A (ko) | 2012-11-05 | 2015-07-15 | 다니스코 유에스 인크. | 써몰리신 프로테아제 변이체를 포함하는 조성물 및 방법 |
| EP2935573A1 (en) | 2012-12-19 | 2015-10-28 | Danisco US Inc. | Novel mannanase, compositions and methods of use thereof |
| ES2797483T3 (es) | 2013-07-19 | 2020-12-02 | Danisco Us Inc | Composiciones y métodos comprendiendo una variante de enzima lipolítica |
| EP3653707B1 (en) | 2013-09-12 | 2025-07-16 | Danisco US Inc. | Compositions and methods comprising lg12-clade protease variants |
| EP3080262B1 (en) | 2013-12-13 | 2019-02-06 | Danisco US Inc. | Serine proteases of bacillus species |
| DK3119884T3 (da) | 2014-03-21 | 2019-10-14 | Danisco Us Inc | Serinproteaser af bacillus-arter |
| EP3268471B1 (en) | 2015-03-12 | 2019-08-28 | Danisco US Inc. | Compositions and methods comprising lg12-clade protease variants |
| US9730867B2 (en) | 2016-01-06 | 2017-08-15 | The Procter & Gamble Company | Methods of forming a slurry with microcapsules formed from phosphate esters |
| CN109715791B (zh) | 2016-05-03 | 2023-07-14 | 丹尼斯科美国公司 | 蛋白酶变体及其用途 |
| US20190136218A1 (en) | 2016-05-05 | 2019-05-09 | Danisco Us Inc | Protease variants and uses thereof |
| WO2017219011A1 (en) | 2016-06-17 | 2017-12-21 | Danisco Us Inc | Protease variants and uses thereof |
| WO2019245704A1 (en) | 2018-06-19 | 2019-12-26 | Danisco Us Inc | Subtilisin variants |
| CA3194468A1 (en) | 2020-10-16 | 2022-04-21 | Johan Smets | Consumer product compositions comprising a population of encapsulates |
| MX2023004232A (es) | 2020-10-16 | 2023-04-21 | Procter & Gamble | Composiciones de productos de consumo con al menos dos poblaciones de encapsulados. |
| US12486478B2 (en) | 2020-10-16 | 2025-12-02 | The Procter & Gamble Company | Consumer products comprising delivery particles with high core:wall ratios |
| WO2023114939A2 (en) | 2021-12-16 | 2023-06-22 | Danisco Us Inc. | Subtilisin variants and methods of use |
| JP2025529133A (ja) | 2022-09-02 | 2025-09-04 | ダニスコ・ユーエス・インク | サブチリシン変異体及びそれに関連する方法 |
| CN120303400A (zh) | 2022-11-09 | 2025-07-11 | 丹尼斯科美国公司 | 枯草杆菌蛋白酶变体和使用方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL128580C (enExample) | 1964-05-25 | |||
| JPS60120848A (ja) * | 1983-12-01 | 1985-06-28 | Mitsubishi Petrochem Co Ltd | 混合第３級アミンオキシドの製造方法 |
| US4942260A (en) | 1988-08-29 | 1990-07-17 | Ethyl Corporation | Amine oxide process with CO2 and aluminum |
| US4960934A (en) | 1989-10-27 | 1990-10-02 | Ethyl Corporation | Amine oxide process |
| GB9102311D0 (en) | 1991-02-02 | 1991-03-20 | Albright & Wilson | Nitrosamine inhibition |
| DE4140259A1 (de) | 1991-12-06 | 1993-06-09 | Basf Ag, 6700 Ludwigshafen, De | Verfahren zur herstellung tertiaerer aminoxide |
| GB9202057D0 (en) * | 1992-01-31 | 1992-03-18 | Albright & Wilson | Synergistic inhibition of nitrosamines and nitrites |
| US5466870A (en) | 1993-10-29 | 1995-11-14 | The Procter & Gamble Company | Process for reducing the levels of nitrite contaminants in amine oxide surfactants |
| US5583258A (en) | 1995-02-15 | 1996-12-10 | The Procter & Gamble Company | Process for preparing mono-long chain amine oxide surfactants |
| DE19520270A1 (de) | 1995-06-02 | 1996-12-05 | Basf Ag | Verfahren zur Herstellung von Aminoxiden |
| DE19528945A1 (de) | 1995-08-07 | 1997-02-13 | Hoechst Ag | Verfahren zur Herstellung von tertiären Aminoxiden |
-
1998
- 1998-11-24 US US09/200,391 patent/US6294514B1/en not_active Expired - Lifetime
-
1999
- 1999-11-18 EP EP99960454A patent/EP1133469B1/en not_active Expired - Lifetime
- 1999-11-18 JP JP2000583854A patent/JP4334772B2/ja not_active Expired - Lifetime
- 1999-11-18 CN CNB998136719A patent/CN1183105C/zh not_active Expired - Lifetime
- 1999-11-18 AT AT99960454T patent/ATE280150T1/de not_active IP Right Cessation
- 1999-11-18 ES ES99960454T patent/ES2228140T3/es not_active Expired - Lifetime
- 1999-11-18 WO PCT/US1999/027315 patent/WO2000031026A1/en not_active Ceased
- 1999-11-18 CA CA002348920A patent/CA2348920C/en not_active Expired - Lifetime
- 1999-11-18 DE DE69921352T patent/DE69921352T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CN1328543A (zh) | 2001-12-26 |
| CA2348920C (en) | 2006-07-25 |
| ES2228140T3 (es) | 2005-04-01 |
| WO2000031026A1 (en) | 2000-06-02 |
| JP2002530368A (ja) | 2002-09-17 |
| US6294514B1 (en) | 2001-09-25 |
| CA2348920A1 (en) | 2000-06-02 |
| DE69921352D1 (de) | 2004-11-25 |
| EP1133469B1 (en) | 2004-10-20 |
| EP1133469A1 (en) | 2001-09-19 |
| CN1183105C (zh) | 2005-01-05 |
| ATE280150T1 (de) | 2004-11-15 |
| JP4334772B2 (ja) | 2009-09-30 |
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