DE1298996B - Verfahren zur Herstellung von quaternaeren Ammoniumperoxysulfaten - Google Patents
Verfahren zur Herstellung von quaternaeren AmmoniumperoxysulfatenInfo
- Publication number
- DE1298996B DE1298996B DEF45993A DEF0045993A DE1298996B DE 1298996 B DE1298996 B DE 1298996B DE F45993 A DEF45993 A DE F45993A DE F0045993 A DEF0045993 A DE F0045993A DE 1298996 B DE1298996 B DE 1298996B
- Authority
- DE
- Germany
- Prior art keywords
- ammonium
- quaternary ammonium
- peroxymonosulfate
- dimethyl
- peroxysulphates
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 17
- 125000001453 quaternary ammonium group Chemical group 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title description 4
- FHHJDRFHHWUPDG-UHFFFAOYSA-L peroxysulfate(2-) Chemical compound [O-]OS([O-])(=O)=O FHHJDRFHHWUPDG-UHFFFAOYSA-L 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 2
- 239000004744 fabric Substances 0.000 description 16
- -1 amino, hydroxy Chemical group 0.000 description 13
- 239000007844 bleaching agent Substances 0.000 description 12
- 239000012425 OXONE® Substances 0.000 description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 11
- 238000004061 bleaching Methods 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 11
- 239000001301 oxygen Substances 0.000 description 11
- OKBMCNHOEMXPTM-UHFFFAOYSA-M potassium peroxymonosulfate Chemical compound [K+].OOS([O-])(=O)=O OKBMCNHOEMXPTM-UHFFFAOYSA-M 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 238000005406 washing Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229920000742 Cotton Polymers 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- 238000005299 abrasion Methods 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- LFINSDKRYHNMRB-UHFFFAOYSA-N diazanium;oxido sulfate Chemical class [NH4+].[NH4+].[O-]OS([O-])(=O)=O LFINSDKRYHNMRB-UHFFFAOYSA-N 0.000 description 5
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000003760 tallow Substances 0.000 description 5
- 241001122767 Theaceae Species 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000005708 Sodium hypochlorite Substances 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- JZBWUTVDIDNCMW-UHFFFAOYSA-L dipotassium;oxido sulfate Chemical compound [K+].[K+].[O-]OS([O-])(=O)=O JZBWUTVDIDNCMW-UHFFFAOYSA-L 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 229920004934 Dacron® Polymers 0.000 description 2
- 229930194542 Keto Natural products 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 150000007973 cyanuric acids Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- FHHJDRFHHWUPDG-UHFFFAOYSA-N peroxysulfuric acid Chemical compound OOS(O)(=O)=O FHHJDRFHHWUPDG-UHFFFAOYSA-N 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- NNJCVNUMXCRDKM-UHFFFAOYSA-L S(=O)(=O)([O-])O[O-].C(CCCCCCCCCCCCCCCCC)[N+](C)(C)C.C(CCCCCCCCCCCCCCCCC)[N+](C)(C)C Chemical compound S(=O)(=O)([O-])O[O-].C(CCCCCCCCCCCCCCCCC)[N+](C)(C)C.C(CCCCCCCCCCCCCCCCC)[N+](C)(C)C NNJCVNUMXCRDKM-UHFFFAOYSA-L 0.000 description 1
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- WLCFKPHMRNPAFZ-UHFFFAOYSA-M didodecyl(dimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCC WLCFKPHMRNPAFZ-UHFFFAOYSA-M 0.000 description 1
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 1
- YMGGAHMANIOXGP-UHFFFAOYSA-L disodium;oxido sulfate Chemical class [Na+].[Na+].[O-]OS([O-])(=O)=O YMGGAHMANIOXGP-UHFFFAOYSA-L 0.000 description 1
- 239000004664 distearyldimethylammonium chloride (DHTDMAC) Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- LSMBCIUIICRQHJ-UHFFFAOYSA-L dodecyl(trimethyl)azanium oxido sulfate Chemical compound CCCCCCCCCCCC[N+](C)(C)C.CCCCCCCCCCCC[N+](C)(C)C.[O-]OS(=O)(=O)[O-] LSMBCIUIICRQHJ-UHFFFAOYSA-L 0.000 description 1
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
- 239000002979 fabric softener Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000003197 gene knockdown Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- VUVMPHNKMULXPD-UHFFFAOYSA-L hexadecyl(trimethyl)azanium;oxido sulfate Chemical compound [O-]OS([O-])(=O)=O.CCCCCCCCCCCCCCCC[N+](C)(C)C.CCCCCCCCCCCCCCCC[N+](C)(C)C VUVMPHNKMULXPD-UHFFFAOYSA-L 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000012430 organic reaction media Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- HJKYXKSLRZKNSI-UHFFFAOYSA-I pentapotassium;hydrogen sulfate;oxido sulfate;sulfuric acid Chemical compound [K+].[K+].[K+].[K+].[K+].OS([O-])(=O)=O.[O-]S([O-])(=O)=O.OS(=O)(=O)O[O-].OS(=O)(=O)O[O-] HJKYXKSLRZKNSI-UHFFFAOYSA-I 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 210000002374 sebum Anatomy 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000008354 tissue degradation Effects 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/62—Quaternary ammonium compounds
- C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
- D06L4/10—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen
- D06L4/13—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen using inorganic agents
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
- D06L4/10—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen
- D06L4/15—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen using organic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Inorganic Chemistry (AREA)
- Detergent Compositions (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US365874A US3353902A (en) | 1964-05-08 | 1964-05-08 | Method of using quaternary ammonium peroxysulfates |
| US67151267A | 1967-07-21 | 1967-07-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1298996B true DE1298996B (de) | 1969-07-10 |
Family
ID=27003129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF45993A Pending DE1298996B (de) | 1964-05-08 | 1965-05-07 | Verfahren zur Herstellung von quaternaeren Ammoniumperoxysulfaten |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US3353902A (enrdf_load_stackoverflow) |
| CH (1) | CH471274A (enrdf_load_stackoverflow) |
| DE (1) | DE1298996B (enrdf_load_stackoverflow) |
| GB (1) | GB1054473A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2207979A1 (de) * | 1971-02-22 | 1972-08-31 | The Procter & Gamble Co, Cincinnati, Ohio (V.StA.) | Trockene chlorfreie Bleichmittel |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4203852A (en) * | 1974-03-01 | 1980-05-20 | Colgate-Palmolive Company | Softener, bleach and anti-cling composition |
| US4404061A (en) * | 1981-08-17 | 1983-09-13 | International Paper Company | Bleaching of lignocellulosic materials with monopersulfuric acid or its salts |
| US4475984A (en) * | 1981-08-17 | 1984-10-09 | International Paper Co. | Process for pretreating wood chips with monoperoxy sulfuric acid or its salts prior to alkaline pulping |
| US5234616A (en) * | 1987-10-30 | 1993-08-10 | The Clorox Company | Method of laundering clothes using a delayed onset active oxygen bleach composition |
| US5559089A (en) * | 1992-03-12 | 1996-09-24 | The Procter & Gamble Company | Low-dosage automatic dishwashing detergent with monopersulfate and enzymes |
| FR2746020B1 (fr) * | 1996-03-14 | 1998-04-24 | Composition a base de peracides pour la decontamination de materiaux souilles par des agents toxiques |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB812752A (en) * | 1956-01-23 | 1959-04-29 | Laporte Chemical | Improvements in or relating to the treatment of textiles |
| US2882121A (en) * | 1954-12-07 | 1959-04-14 | Stevensons Dyers Ltd | Permonosulfuric acid for bleaching synthetic polymer textiles |
| BE572175A (enrdf_load_stackoverflow) * | 1957-10-31 | |||
| US3042622A (en) * | 1957-11-01 | 1962-07-03 | Colgate Palmolive Co | Abrasive cleaning composition |
| US3156521A (en) * | 1961-10-19 | 1964-11-10 | Dow Chemical Co | Process of bleaching textiles with lower alkyl quaternary ammonium perhalides |
| US3149990A (en) * | 1962-01-19 | 1964-09-22 | Minnesota Mining & Mfg | Heat-sensitive copy-sheet |
| US3142691A (en) * | 1962-02-02 | 1964-07-28 | Henkel & Cie Gmbh | Production of light-colored sulfonated fatty acids and fatty acid derivatives |
-
0
- GB GB1054473D patent/GB1054473A/en active Active
-
1964
- 1964-05-08 US US365874A patent/US3353902A/en not_active Expired - Lifetime
-
1965
- 1965-05-07 DE DEF45993A patent/DE1298996B/de active Pending
- 1965-05-07 CH CH637865A patent/CH471274A/de not_active IP Right Cessation
-
1967
- 1967-07-21 US US671512A patent/US3475493A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2207979A1 (de) * | 1971-02-22 | 1972-08-31 | The Procter & Gamble Co, Cincinnati, Ohio (V.StA.) | Trockene chlorfreie Bleichmittel |
Also Published As
| Publication number | Publication date |
|---|---|
| US3353902A (en) | 1967-11-21 |
| CH637865A4 (enrdf_load_stackoverflow) | 1968-12-31 |
| CH471274A (de) | 1969-05-30 |
| US3475493A (en) | 1969-10-28 |
| GB1054473A (enrdf_load_stackoverflow) |
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