WO1982001993A1 - Use of polyethylene imine as absorbant for odorous substances - Google Patents
Use of polyethylene imine as absorbant for odorous substances Download PDFInfo
- Publication number
- WO1982001993A1 WO1982001993A1 PCT/DE1981/000226 DE8100226W WO8201993A1 WO 1982001993 A1 WO1982001993 A1 WO 1982001993A1 DE 8100226 W DE8100226 W DE 8100226W WO 8201993 A1 WO8201993 A1 WO 8201993A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polyethyleneimine
- polyethylene imine
- odor
- odorous substances
- air
- Prior art date
Links
- 229920002873 Polyethylenimine Polymers 0.000 title claims abstract description 56
- 239000000126 substance Substances 0.000 title claims abstract description 12
- 239000007864 aqueous solution Substances 0.000 claims abstract description 4
- 239000013543 active substance Substances 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 8
- 239000002250 absorbent Substances 0.000 claims description 7
- 230000002745 absorbent Effects 0.000 claims description 7
- 239000007921 spray Substances 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 abstract description 5
- 150000001299 aldehydes Chemical class 0.000 abstract description 4
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 4
- 229930195729 fatty acid Natural products 0.000 abstract description 4
- 239000000194 fatty acid Substances 0.000 abstract description 4
- 150000004665 fatty acids Chemical class 0.000 abstract description 4
- 150000002576 ketones Chemical class 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 4
- 238000004332 deodorization Methods 0.000 abstract 2
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 235000019645 odor Nutrition 0.000 description 13
- 239000000203 mixture Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 230000009102 absorption Effects 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000008030 elimination Effects 0.000 description 4
- 238000003379 elimination reaction Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000002304 perfume Substances 0.000 description 3
- 150000003568 thioethers Chemical class 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 238000004378 air conditioning Methods 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000002781 deodorant agent Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000009965 odorless effect Effects 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000010865 sewage Substances 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- HTIRHQRTDBPHNZ-UHFFFAOYSA-N Dibutyl sulfide Chemical compound CCCCSCCCC HTIRHQRTDBPHNZ-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000004887 air purification Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940045713 antineoplastic alkylating drug ethylene imines Drugs 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000002984 plastic foam Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- -1 polyterpene alcohols Chemical class 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- GAWWVVGZMLGEIW-GNNYBVKZSA-L zinc ricinoleate Chemical compound [Zn+2].CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O.CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O GAWWVVGZMLGEIW-GNNYBVKZSA-L 0.000 description 1
- 229940100530 zinc ricinoleate Drugs 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L9/00—Disinfection, sterilisation or deodorisation of air
- A61L9/14—Disinfection, sterilisation or deodorisation of air using sprayed or atomised substances including air-liquid contact processes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L9/00—Disinfection, sterilisation or deodorisation of air
- A61L9/01—Deodorant compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L9/00—Disinfection, sterilisation or deodorisation of air
- A61L9/015—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone
- A61L9/04—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone using substances evaporated in the air without heating
- A61L9/12—Apparatus, e.g. holders, therefor
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
Definitions
- the invention relates to the use of polyethyleneimine for the absorption of odor-active substances.
- polyethyleneimine is extremely suitable for forming stable absorption compounds with fatty acids, aldehydes and ketones and thus rendering them odorless.
- the invention accordingly relates to the use of polyethyleneimine for the absorption of odor-active substances.
- odor absorbent The most important requirements to be met by an odor absorbent are good effectiveness ibei lower Amount of use, value for money, odorlessness, toxicological harmlessness, compatibility with materials to be treated and biodegradability. These requirements are ideally met by polyethyleneimine.
- Polyethyleneimine is made by polymerizing ethyleneimine.
- the degree of polymerization of the polyethylene imine used according to the invention must be so high that the polyethyleneimine is toxicologically harmless. As the degree of polymerization increases, the water solubility of the polyethyleneimine decreases.
- the degree of polymerization of the polyethyleneimine used according to the invention is not subject to any restrictions apart from the aforementioned minimum degree of polymerization, those polymeric ethyleneimines which still have sufficient water solubility are preferred for reasons of easier handling.
- Such polyethyleneimines are commercially available and are known to the person skilled in the art with regard to their properties (cf. Ullmann's Encyclopedia of Industrial Chemistry, 3rd edition, 3rd volume, page 144, for example "Polymin P", trademark of BASF).
- polyethyleneimine according to the invention can be carried out in various ways. Doing so the amount to be used is of course dependent on the concentration of the odor-active substances to be absorbed in the medium to be treated. Because of their ease of use, the use of aqueous polyethyleneimine solutions is appropriate. Although the polyethyleneimine concentration in these solutions is not of critical importance (good results are already achieved with polyethyleneimine concentrations in the range of 0.01%), a polyethyleneimine concentration of 0.1 to 10% and preferably 1 to 3% has been found, particularly from an economic point of view. proven.
- Solutions of polyethyleneimine in water or other solvents and mixtures thereof are suitable for spraying or atomizing and are preferably used in this way.
- Another preferred embodiment of the invention consists in impregnating materials which come into contact with odor-active substances with polyethyleneimine. So substances, substances, filters or filter masses and objects such as shoe insoles can be impregnated with polyethyleneimine,
- polyethyleneimine in particular fatty acids, aldehydes and ketones
- Absorp tion of amines and sulfides less pronounced, so that a longer contact is required for fully satisfactory results.
- the polyethyleneimine used according to the invention together with other odor absorbents in order to ensure that compounds such as amines and sulfides are also completely absorbed with short contact times.
- the polyethyleneimine can be used alone or together with other odor absorbents, depending on the application, together with other customary substances.
- polyethyleneimine to absorb odor-active substances is practically possible wherever odor elimination is desired.
- Preferred areas of application are cosmetics and body care, technical odor elimination and room air improvement.
- polyethyleneimine can be used in body deodorants.
- shoe insoles can be impregnated with polyethyleneimine.
- polyethyleneimine for odor control in sewage treatment plants, in particular the waste air that accumulates in these.
- the invention in particular gives the municipalities the possibility of freeing the residents of municipal sewage treatment plants from often very unpleasant odors in a simple and inexpensive manner.
- Other areas of application that are suitable for odor elimination using polyethyleneimine include stables, animal processing plants, hospitals and chemical companies.
- polyethyleneimine as an odor absorbent
- Another focus of the use according to the invention of polyethyleneimine as an odor absorbent is in the field of indoor air improvement. So can in the air duct. Lines, ducts and shafts of air conditioning and air circulation systems are sprayed with polyethyleneimine solutions, which leads to a continuous elimination of unwanted and undesirable odors.
- filters which are impregnated with polyethyleneimine can be used in the systems mentioned and in exhaust air purification systems. In this way, the required fresh air supply is reduced, which in turn leads to energy savings.
- the use of polyethyleneimine solutions in the form of sprays to improve the odor in, for example, toilets and kitchens is particularly suitable.
- the absorption of a number of odor-active substances was investigated with the help of polyethyleneimine.
- polyethyleneimine For this purpose, about 50 g of gauze were impregnated with 100 ml of a 1.5% aqueous polyethyleneimine solution and then for 24 hours air dried.
- the gauze impregnated in this way was introduced into a closed system with a volume of approximately 300 ml.
- the air in the closed system was circulated by an integrated diaphragm pump. In each case 0.01 g of an odor-active substance was introduced into the circuit.
- the action of the polyethyleneimine can be supported by adding other absorbents such as zinc sulfate, zinc ricinoleate, soda and zinc carbonate.
- the exiting air mixture (see Example 1) is then free of all odor-active substances used.
- a typical wording is as follows:
- porous support materials such as cotton mats, felt mats, paper or plastic mats were treated with a 1.0 to 2.0% aqueous solution of polyethyleneimine and arranged in an air stream.
- activated carbon was soaked or sprayed with a 1.0 to 2.0% polyethyleneimine solution and placed in a frame in an air stream.
- a 0.1 to 2.0% aqueous solution of polyethyleneimine was atomized into an air circuit or an air outlet (e.g. air conditioning, Exhaust air) or atomized via clarifiers or introduced into their air suction.
- Formulations for cosmetic purposes a) deodorant spray
- composition is filled as a pump spray using a "press pack” system or with propellant.
- compositions according to a) and b) are suitable as an additive in soap finishing, the amount of the additive preferably being about 1.0 to 2.0%.
- Composition A was filled using a "press pack” system while Composition B was filled with a blowing agent in a weight ratio of 70:30.
- polyethyleneimine "Polymin P” and “Polymin SK” (trademark of BASF) were used.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
- Treating Waste Gases (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL8120479A NL8120479A (nl) | 1980-12-18 | 1981-12-16 | Toepassing van polyethyleenimine voor het absorberen van geuraktieve stoffen. |
| BR8108919A BR8108919A (pt) | 1980-12-18 | 1981-12-16 | Utilizacao de polietilenimina para a absorcao de substancias de odoridade ativa |
| DK360582A DK360582A (da) | 1980-12-18 | 1982-08-11 | Anvendelse af polyethyleniaain til absorption af lugtaktive stoffer |
| FI822843A FI76495C (fi) | 1980-12-18 | 1982-08-16 | Anvaendning av polyetylenimin foer luktbekaempning. |
| NO822800A NO158281C (no) | 1980-12-18 | 1982-08-17 | Anvendelse av polyethyleniminloesninger ved luktbekjempelse |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3047774A DE3047774C2 (de) | 1980-12-18 | 1980-12-18 | Verwendung von Polyethyleniminlösungen zur Geruchsbekämpfung |
| DE3047774801218 | 1980-12-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1982001993A1 true WO1982001993A1 (en) | 1982-06-24 |
Family
ID=6119535
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/DE1981/000226 WO1982001993A1 (en) | 1980-12-18 | 1981-12-16 | Use of polyethylene imine as absorbant for odorous substances |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS57501944A (cs) |
| AU (1) | AU550277B2 (cs) |
| BR (1) | BR8108919A (cs) |
| CA (1) | CA1173631A (cs) |
| CH (1) | CH658392A5 (cs) |
| DE (1) | DE3047774C2 (cs) |
| ES (1) | ES508649A0 (cs) |
| FI (1) | FI76495C (cs) |
| FR (1) | FR2497670B1 (cs) |
| GB (1) | GB2102292B (cs) |
| GR (1) | GR76970B (cs) |
| IT (1) | IT1142135B (cs) |
| NL (1) | NL8120479A (cs) |
| PT (1) | PT74148B (cs) |
| SE (1) | SE448148B (cs) |
| WO (1) | WO1982001993A1 (cs) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0277398A1 (en) * | 1985-10-31 | 1988-08-10 | Aikoh Co. Ltd. | A deodorant composition and use thereof |
| EP0858797A1 (fr) * | 1997-02-14 | 1998-08-19 | L'oreal | Composition déodorante comprenant un dendrimère |
| WO2003088931A3 (en) * | 2002-04-16 | 2004-04-29 | Cosmetica Inc | Polymeric odor absorption ingredients for personal care products |
| WO2005110502A1 (en) * | 2004-04-30 | 2005-11-24 | Kimberly-Clark Worldwide, Inc. | Absorption of pain-causing agents |
| DE102009040089A1 (de) | 2009-09-04 | 2011-07-21 | Beiersdorf AG, 20253 | Zubereitungen mit wasserunlöslichen polymeren Aminen zur Verminderung von Körpergeruch |
| WO2012175330A2 (en) | 2011-06-20 | 2012-12-27 | L'oreal | Cosmetic use of a flocculant polymer as antiperspirant |
| KR20140040102A (ko) * | 2011-02-11 | 2014-04-02 | 킴벌리-클라크 월드와이드, 인크. | 살균 용액과 함께 사용하기 위한 와이프 |
| US8778321B2 (en) | 2007-10-01 | 2014-07-15 | Nanotex Llc | Modification of cellulosic substrates to control body odor |
| US9260817B2 (en) | 2009-09-18 | 2016-02-16 | The Procter & Gamble Company | Freshening compositions comprising malodor binding polymers and malodor counteractants |
| US9273427B2 (en) | 2009-09-18 | 2016-03-01 | The Procter & Gamble Company | Freshening compositions comprising malodor binding polymers |
| US9821081B2 (en) | 2012-11-27 | 2017-11-21 | The Procter & Gamble Company | Perfume-free malodor reducing compositions |
| GB2570215A (en) * | 2017-12-12 | 2019-07-17 | Henkel Kgaa | Polyethylene imine with low molecular weight as antiperspirant active substance in the form of a suspension |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2271716A (en) * | 1992-10-26 | 1994-04-27 | Unilever Plc | Propellant-free deodorant composition |
| US6764986B1 (en) * | 1999-07-08 | 2004-07-20 | Procter & Gamble Company | Process for producing particles of amine reaction products |
| US6740713B1 (en) * | 1999-07-08 | 2004-05-25 | Procter & Gamble Company | Process for producing particles of amine reaction products |
| CA2486879A1 (en) * | 2002-05-29 | 2003-12-04 | Unilever Plc | Odor control in amine salt containing cosmetic compositions |
| WO2007021532A1 (en) * | 2005-08-09 | 2007-02-22 | Exxonmobil Research And Engineering Company | Polyalkyleneimines and polyalkyleneacrylamide salt for acid gas scrubbing process |
| US20080164439A1 (en) * | 2007-01-10 | 2008-07-10 | Xinggao Fang | Textiles treated with hyperbranched polyethyleneimine derivatives for odor control properties |
| US20090246258A1 (en) * | 2008-03-28 | 2009-10-01 | Piyush Shukla | Antimicrobial and odor adsorbing textile |
| US20120183489A1 (en) * | 2011-01-14 | 2012-07-19 | Ricky Ah-Man Woo | Compositions comprising metallated malodor control polymers |
| US9248209B2 (en) | 2011-01-14 | 2016-02-02 | The Procter & Gamble Company | Compositions comprising hydrophobically modified malodor control polymers |
| WO2014085215A1 (en) * | 2012-11-27 | 2014-06-05 | The Procter & Gamble Company | Perfume-free malodor reducing compositions |
| JP6635733B2 (ja) * | 2015-09-14 | 2020-01-29 | 株式会社日本触媒 | 消臭剤 |
| CN107955340B (zh) * | 2017-11-02 | 2020-05-29 | 上海日之升科技有限公司 | 低散发汽车空调出风口叶片用pbt材料及其制备方法 |
| US11518963B2 (en) | 2018-10-18 | 2022-12-06 | Milliken & Company | Polyethyleneimine compounds containing N-halamine and derivatives thereof |
| US11466122B2 (en) | 2018-10-18 | 2022-10-11 | Milliken & Company | Polyethyleneimine compounds containing N-halamine and derivatives thereof |
| US11732218B2 (en) | 2018-10-18 | 2023-08-22 | Milliken & Company | Polyethyleneimine compounds containing N-halamine and derivatives thereof |
| US11299591B2 (en) | 2018-10-18 | 2022-04-12 | Milliken & Company | Polyethyleneimine compounds containing N-halamine and derivatives thereof |
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| JPS4833118A (cs) * | 1971-06-02 | 1973-05-08 | ||
| FR2164801A1 (cs) * | 1971-12-22 | 1973-08-03 | Gillette Co | |
| US3939099A (en) * | 1974-12-26 | 1976-02-17 | Chesebrough-Pond's, Inc. | Fragrance composition |
| DE2623652A1 (de) * | 1975-05-30 | 1976-12-09 | Procter & Gamble | Unterwaescheartikel und verfahren zu deren herstellung |
| FR2310800A1 (fr) * | 1975-05-16 | 1976-12-10 | Japan Synthetic Rubber Co Ltd | Parfum-deodorant a base d'hydrogel |
| JPS534783A (en) * | 1976-07-02 | 1978-01-17 | Japan Synthetic Rubber Co Ltd | Gel hydrate and gel hydrate deodorant |
| FR2368509A1 (fr) * | 1976-10-20 | 1978-05-19 | Oreal | Nouveaux deodorants ou desodorisants et compositions les contenant |
| DE2737070A1 (de) * | 1977-08-17 | 1979-03-08 | Vulich | Verfahren zur reinigung von gasen |
| FR2455068A1 (fr) * | 1979-04-26 | 1980-11-21 | Kuraray Co | Gel aqueux a base de derives ammoniacaux de copolymeres de l'anhydride maleique et de polyamines et leurs utilisations |
| US4252789A (en) * | 1979-08-01 | 1981-02-24 | The Gillette Company | Deodorant stick |
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| GB999057A (en) * | 1963-08-22 | 1965-07-21 | British American Tobacco Co | Improvements relating to cigarette filters |
| JPS503396B2 (cs) * | 1971-12-06 | 1975-02-04 | ||
| SE7607100L (sv) * | 1975-07-02 | 1977-01-03 | Rohm & Haas | Absorbermedel |
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- 1980-12-18 DE DE3047774A patent/DE3047774C2/de not_active Expired
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1981
- 1981-12-16 BR BR8108919A patent/BR8108919A/pt unknown
- 1981-12-16 AU AU79345/82A patent/AU550277B2/en not_active Ceased
- 1981-12-16 CH CH4757/82A patent/CH658392A5/de not_active IP Right Cessation
- 1981-12-16 JP JP57500174A patent/JPS57501944A/ja active Pending
- 1981-12-16 NL NL8120479A patent/NL8120479A/nl unknown
- 1981-12-16 WO PCT/DE1981/000226 patent/WO1982001993A1/en active IP Right Grant
- 1981-12-16 GB GB08223605A patent/GB2102292B/en not_active Expired
- 1981-12-17 PT PT74148A patent/PT74148B/pt unknown
- 1981-12-17 FR FR8123575A patent/FR2497670B1/fr not_active Expired
- 1981-12-17 GR GR66830A patent/GR76970B/el unknown
- 1981-12-18 IT IT25684/81A patent/IT1142135B/it active
- 1981-12-18 CA CA000392735A patent/CA1173631A/en not_active Expired
- 1981-12-18 ES ES508649A patent/ES508649A0/es active Granted
-
1982
- 1982-08-13 SE SE8204681A patent/SE448148B/sv not_active IP Right Cessation
- 1982-08-16 FI FI822843A patent/FI76495C/fi not_active IP Right Cessation
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| JPS4833118A (cs) * | 1971-06-02 | 1973-05-08 | ||
| FR2164801A1 (cs) * | 1971-12-22 | 1973-08-03 | Gillette Co | |
| US3939099A (en) * | 1974-12-26 | 1976-02-17 | Chesebrough-Pond's, Inc. | Fragrance composition |
| FR2310800A1 (fr) * | 1975-05-16 | 1976-12-10 | Japan Synthetic Rubber Co Ltd | Parfum-deodorant a base d'hydrogel |
| DE2623652A1 (de) * | 1975-05-30 | 1976-12-09 | Procter & Gamble | Unterwaescheartikel und verfahren zu deren herstellung |
| JPS534783A (en) * | 1976-07-02 | 1978-01-17 | Japan Synthetic Rubber Co Ltd | Gel hydrate and gel hydrate deodorant |
| FR2368509A1 (fr) * | 1976-10-20 | 1978-05-19 | Oreal | Nouveaux deodorants ou desodorisants et compositions les contenant |
| DE2737070A1 (de) * | 1977-08-17 | 1979-03-08 | Vulich | Verfahren zur reinigung von gasen |
| FR2455068A1 (fr) * | 1979-04-26 | 1980-11-21 | Kuraray Co | Gel aqueux a base de derives ammoniacaux de copolymeres de l'anhydride maleique et de polyamines et leurs utilisations |
| US4252789A (en) * | 1979-08-01 | 1981-02-24 | The Gillette Company | Deodorant stick |
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| Chemical Abstracts, Vol. 89, No. 2, published on 10 July 1978 (Columbus Ohio USA) page 359, column 2, abstract 11983m; & JP-A-53 004 783, published on 17 January 1978 (JAPAN SYNTHETIC RUBBER CO.) * |
| Chemical Abstracts, Vol. 89, No. 4, published on 24 July 1978, (Columbus, Ohio, USA) F. Woeller et al: "Sythesis of porous polyaromatic column packings for GC analysis of extraterrestrial atmospheres" page 784, column 2, abstract 35900h; & J.Chromatrogr.Sci. 1978, 16(4), 137-40 * |
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0354281A1 (en) * | 1985-10-31 | 1990-02-14 | Aikoh Co. Ltd. | A deodorant composition and use thereof |
| AT395534B (de) * | 1985-10-31 | 1993-01-25 | Aikoh Co | Desodorierende zusammensetzung |
| AT398901B (de) * | 1985-10-31 | 1995-02-27 | Aikoh & Co Ltd | Desodorierende zusammensetzung |
| EP0277398A1 (en) * | 1985-10-31 | 1988-08-10 | Aikoh Co. Ltd. | A deodorant composition and use thereof |
| EP0858797A1 (fr) * | 1997-02-14 | 1998-08-19 | L'oreal | Composition déodorante comprenant un dendrimère |
| FR2759582A1 (fr) * | 1997-02-14 | 1998-08-21 | Oreal | Composition deodorante |
| US6001342A (en) * | 1997-02-14 | 1999-12-14 | L'oreal | Deodorant composition and use thereof |
| WO2003088931A3 (en) * | 2002-04-16 | 2004-04-29 | Cosmetica Inc | Polymeric odor absorption ingredients for personal care products |
| WO2005110502A1 (en) * | 2004-04-30 | 2005-11-24 | Kimberly-Clark Worldwide, Inc. | Absorption of pain-causing agents |
| US8778321B2 (en) | 2007-10-01 | 2014-07-15 | Nanotex Llc | Modification of cellulosic substrates to control body odor |
| DE102009040089A1 (de) | 2009-09-04 | 2011-07-21 | Beiersdorf AG, 20253 | Zubereitungen mit wasserunlöslichen polymeren Aminen zur Verminderung von Körpergeruch |
| US9273427B2 (en) | 2009-09-18 | 2016-03-01 | The Procter & Gamble Company | Freshening compositions comprising malodor binding polymers |
| US9260817B2 (en) | 2009-09-18 | 2016-02-16 | The Procter & Gamble Company | Freshening compositions comprising malodor binding polymers and malodor counteractants |
| KR20140040102A (ko) * | 2011-02-11 | 2014-04-02 | 킴벌리-클라크 월드와이드, 인크. | 살균 용액과 함께 사용하기 위한 와이프 |
| EP2672873A4 (en) * | 2011-02-11 | 2015-10-07 | Kimberly Clark Co | WIPE CLOTH FOR USE WITH A DEVOTIVE SOLUTION |
| KR101968771B1 (ko) * | 2011-02-11 | 2019-04-12 | 킴벌리-클라크 월드와이드, 인크. | 살균 용액과 함께 사용하기 위한 와이프 |
| WO2012175330A2 (en) | 2011-06-20 | 2012-12-27 | L'oreal | Cosmetic use of a flocculant polymer as antiperspirant |
| US9821081B2 (en) | 2012-11-27 | 2017-11-21 | The Procter & Gamble Company | Perfume-free malodor reducing compositions |
| GB2570215A (en) * | 2017-12-12 | 2019-07-17 | Henkel Kgaa | Polyethylene imine with low molecular weight as antiperspirant active substance in the form of a suspension |
| GB2570215B (en) * | 2017-12-12 | 2020-03-25 | Henkel Kgaa | Polyethylene imine with low molecular weight as antiperspirant active substance in the form of a suspension |
Also Published As
| Publication number | Publication date |
|---|---|
| AU550277B2 (en) | 1986-03-13 |
| JPS57501944A (cs) | 1982-11-04 |
| FI76495B (fi) | 1988-07-29 |
| FI822843A0 (fi) | 1982-08-16 |
| FR2497670A1 (fr) | 1982-07-16 |
| ES8405276A1 (es) | 1984-06-16 |
| GR76970B (cs) | 1984-09-04 |
| FR2497670B1 (fr) | 1986-04-18 |
| CH658392A5 (de) | 1986-11-14 |
| IT8125684A0 (it) | 1981-12-18 |
| GB2102292A (en) | 1983-02-02 |
| AU7934582A (en) | 1982-07-01 |
| DE3047774A1 (de) | 1982-07-01 |
| BR8108919A (pt) | 1982-11-30 |
| NL8120479A (nl) | 1982-11-01 |
| FI822843L (fi) | 1982-08-16 |
| GB2102292B (en) | 1984-05-16 |
| SE8204681D0 (sv) | 1982-08-13 |
| PT74148B (en) | 1986-01-24 |
| SE448148B (sv) | 1987-01-26 |
| SE8204681L (sv) | 1982-08-13 |
| FI76495C (fi) | 1988-11-10 |
| CA1173631A (en) | 1984-09-04 |
| IT1142135B (it) | 1986-10-08 |
| PT74148A (en) | 1982-01-01 |
| ES508649A0 (es) | 1984-06-16 |
| DE3047774C2 (de) | 1986-10-30 |
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