WO2011070446A1 - Formule désodorisante - Google Patents
Formule désodorisante Download PDFInfo
- Publication number
- WO2011070446A1 WO2011070446A1 PCT/IB2010/003451 IB2010003451W WO2011070446A1 WO 2011070446 A1 WO2011070446 A1 WO 2011070446A1 IB 2010003451 W IB2010003451 W IB 2010003451W WO 2011070446 A1 WO2011070446 A1 WO 2011070446A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- weight
- sulfur
- deodorizing
- formulation according
- component
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 54
- 238000009472 formulation Methods 0.000 title claims abstract description 25
- 230000001877 deodorizing effect Effects 0.000 title claims abstract description 22
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 28
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 27
- 239000011593 sulfur Substances 0.000 claims abstract description 27
- 239000010426 asphalt Substances 0.000 claims abstract description 21
- 239000003085 diluting agent Substances 0.000 claims abstract description 9
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 7
- 150000001298 alcohols Chemical class 0.000 claims abstract description 5
- 239000013543 active substance Substances 0.000 claims description 13
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims description 7
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 claims description 6
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical group CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 claims description 6
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal group Chemical group C(CCCCCC)=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 claims description 6
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical group CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims description 6
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 claims description 6
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 150000003505 terpenes Chemical class 0.000 claims description 5
- 235000007586 terpenes Nutrition 0.000 claims description 5
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 claims description 4
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 claims description 4
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 claims description 4
- 229930007744 linalool Natural products 0.000 claims description 4
- BOPPSUHPZARXTH-UHFFFAOYSA-N ocean propanal Chemical compound O=CC(C)CC1=CC=C2OCOC2=C1 BOPPSUHPZARXTH-UHFFFAOYSA-N 0.000 claims description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 4
- WUOACPNHFRMFPN-SECBINFHSA-N (S)-(-)-alpha-terpineol Chemical group CC1=CC[C@@H](C(C)(C)O)CC1 WUOACPNHFRMFPN-SECBINFHSA-N 0.000 claims description 3
- GRWFGVWFFZKLTI-IUCAKERBSA-N 1S,5S-(-)-alpha-Pinene Natural products CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 claims description 3
- NFAVNWJJYQAGNB-UHFFFAOYSA-N 2-methylundecanal Chemical compound CCCCCCCCCC(C)C=O NFAVNWJJYQAGNB-UHFFFAOYSA-N 0.000 claims description 3
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 claims description 3
- 239000005770 Eugenol Substances 0.000 claims description 3
- 239000005792 Geraniol Substances 0.000 claims description 3
- 241000234269 Liliales Species 0.000 claims description 3
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 claims description 3
- OVKDFILSBMEKLT-UHFFFAOYSA-N alpha-Terpineol Chemical group CC(=C)C1(O)CCC(C)=CC1 OVKDFILSBMEKLT-UHFFFAOYSA-N 0.000 claims description 3
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 claims description 3
- 229940088601 alpha-terpineol Drugs 0.000 claims description 3
- 229940019836 cyclamen aldehyde Drugs 0.000 claims description 3
- 239000002781 deodorant agent Substances 0.000 claims description 3
- 229960002217 eugenol Drugs 0.000 claims description 3
- 229940113087 geraniol Drugs 0.000 claims description 3
- SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical compound O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 claims description 3
- 235000001510 limonene Nutrition 0.000 claims description 3
- 229940087305 limonene Drugs 0.000 claims description 3
- 229960001047 methyl salicylate Drugs 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- ZFNVDHOSLNRHNN-UHFFFAOYSA-N xi-3-(4-Isopropylphenyl)-2-methylpropanal Chemical compound O=CC(C)CC1=CC=C(C(C)C)C=C1 ZFNVDHOSLNRHNN-UHFFFAOYSA-N 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000002480 mineral oil Substances 0.000 claims description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 2
- 229960004889 salicylic acid Drugs 0.000 claims description 2
- 125000003447 alpha-pinene group Chemical group 0.000 claims 1
- 235000010446 mineral oil Nutrition 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000003902 salicylic acid esters Chemical class 0.000 abstract 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- 239000006057 Non-nutritive feed additive Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- WEEGYLXZBRQIMU-UHFFFAOYSA-N Eucalyptol Chemical compound C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 229910017464 nitrogen compound Inorganic materials 0.000 description 2
- 150000002830 nitrogen compounds Chemical class 0.000 description 2
- 150000002898 organic sulfur compounds Chemical class 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 1
- GLZPCOQZEFWAFX-JXMROGBWSA-N (E)-Geraniol Chemical compound CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- NKZPGPZCKPODMT-UHFFFAOYSA-N 3-(4-tert-butylphenyl)butanal Chemical compound O=CCC(C)C1=CC=C(C(C)(C)C)C=C1 NKZPGPZCKPODMT-UHFFFAOYSA-N 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- -1 alkyl salicylates Chemical class 0.000 description 1
- HMKKIXGYKWDQSV-KAMYIIQDSA-N alpha-Amylcinnamaldehyde Chemical compound CCCCC\C(C=O)=C\C1=CC=CC=C1 HMKKIXGYKWDQSV-KAMYIIQDSA-N 0.000 description 1
- GUUHFMWKWLOQMM-NTCAYCPXSA-N alpha-hexylcinnamaldehyde Chemical compound CCCCCC\C(C=O)=C/C1=CC=CC=C1 GUUHFMWKWLOQMM-NTCAYCPXSA-N 0.000 description 1
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 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
- A61L9/01—Deodorant compositions
Definitions
- the invention relates to a deodorizing formulation, in particular for a mixture of bitumen and sulfur, which contains active, odor-reducing agents and a diluent, and to processes for the preparation of a composition based on sulfur, which can be used for odor reduction.
- bitumen processing can be carried out at lower temperatures in the range of 130 to 150 ° C.
- US-A-3,960,585 and WO 2005/059016 disclose that the formation of hydrogen sulfide upon heating a mixture of asphalt and sulfur can be suppressed by the addition of free radical-forming inhibitors and / or redox catalysts. However, these additives are not sufficiently effective.
- the invention therefore an object of the invention to suppress or at least reduce this odor nuisance in mixtures of bitumen and sulfur.
- a deodorizing formulation according to claim 1 comprising active agents and at least one diluent, the active agents comprising the following components:
- the active agents consist of the following components:
- EP-A 1 235 768 and WO 2009/019 041 describe processes for reducing the odor of bitumen in which odor-reducing formulations are mixed into liquid bitumen, which in particular contain certain carboxylic acid esters or certain aldehydes.
- the foul-smelling volatiles of bitumen consist essentially of organic sulfur and nitrogen compounds, while in the present case especially hydrogen sulphide and sulfur dioxide must be eliminated.
- the bitumen / sulfur mixture preferably contains minor amounts of sulfur, in particular 20 to 40 wt.%.
- the deodorizing formulation of active agents and diluents is preferably incorporated into the bitumen / sulfur mixture in amounts of from 50 to 1000 ppm, in particular from 100 to 500 ppm, the formulation preferably being from 5 to 50% by weight and in particular from 10 to 40% by weight of active agents and from 95 to 50% by weight, in particular from 90 to 60% by weight, of diluent.
- Component A is preferably benzyl salicylate, but other alkyl salicylates having 1 to 8 carbon atoms in the alkyl radical are also suitable, for example methyl salicylate.
- Benzylsalicylate has the great advantage that it is extremely high due to its very high boiling point low vapor pressure, so that the deodorizing formulation remains effective in the mixture of bitumen and sulfur for a long time, eg several months.
- Component B is preferably heptanal or dodecanal.
- the further aldehydes of component C are preferably selected from:
- the alcohols of component D are preferably naturally occurring alcohols selected from:
- Limonene (1-methyl-4-prop-1-en-2-ylcyclohexene C] 0 Hi 6 ).
- the optional ketones of component F are preferably selected from:
- Benzophenone butyl methyl ketone and 1,8-cineole.
- the active agents are used together with a diluent.
- the deodorizing formulation causes the deodorizing formulation to be in liquid form. At the same time it acts as a mixing agent when mixing the individual components. In addition, it prevents that evaporate at relatively high temperature individual relatively low-boiling components of the active agents.
- Preferred diluents are mineral oils, ie hydrocarbon middle distillates, such as CATENEX from SHELL, and vegetable oils, such as sunflower oil or mixtures thereof.
- the present invention further relates to a method according to
- a deodorant composition based on sulfur and 0.02 to 0.3% by weight of the deodorizing formulation, if appropriate together with 0 to 8% by weight of other additives, is initially used , each based on sulfur produced.
- Suitable additives are processing aids, for example ethylenebisstearylamide or amyl acetate, and colorants, for example carbon powders. This mixture can then be incorporated at 140 to 170 ° C in liquid bitumen.
- sulfur based means that sulfur is the essential ingredient of the composition.
- the first deodorizing agent Preferably, the first deodorizing agent
- Mixture of sulfur and optionally the processing aid and the colorant to produce and apply the deodorizing formulation on the particles on the surface for example, according to customary in plastics technology by spraying, by tumbling or by compounding.
- a mixture of active agents was prepared from:
- a mixture of active agents was prepared from:
Landscapes
- Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
Abstract
L'invention concerne une formule désodorisante, notamment pour un mélange de bitume et de soufre, laquelle formule contient des agents actifs atténuant les odeurs, à base d'esters d'acide salicylique, d'aldéhydes et éventuellement d'alcools, ainsi qu'un diluant. L'invention concerne en outre des procédés de préparation d'une composition désodorisante à base de soufre, laquelle peut être incorporée au bitume en vue d'atténuer les odeurs.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP10814658A EP2509642A1 (fr) | 2009-12-08 | 2010-12-07 | Formule désodorisante |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP09306195A EP2338526A1 (fr) | 2009-12-08 | 2009-12-08 | Formule désodorisante |
EP09306195.0 | 2009-12-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2011070446A1 true WO2011070446A1 (fr) | 2011-06-16 |
Family
ID=42209374
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/IB2010/003451 WO2011070446A1 (fr) | 2009-12-08 | 2010-12-07 | Formule désodorisante |
Country Status (2)
Country | Link |
---|---|
EP (2) | EP2338526A1 (fr) |
WO (1) | WO2011070446A1 (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018068728A1 (fr) * | 2016-10-12 | 2018-04-19 | Shell Internationale Research Maatschappij B.V. | Procédé de réduction d'odeurs de bitume et de crmb |
US11274208B2 (en) | 2016-10-12 | 2022-03-15 | Shell Oil Company | Reducing crumb rubber modified bitumen odors |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3960585A (en) | 1973-12-17 | 1976-06-01 | Shell Oil Company | Reducing H2 S-emission from hot cast sulfur-asphalt mixtures |
DE19725920A1 (de) * | 1996-06-25 | 1998-02-05 | Heresch & Heresch Umweltengine | Verfahren zur Geruchsneutralisation bei Asphaltmischanlagen |
EP1235768A1 (fr) | 1999-11-16 | 2002-09-04 | Alan Jeffrey Ronyak | Composition hydrocarbonee contenant des agents de suppression d'odeur |
WO2004045657A1 (fr) * | 2002-11-15 | 2004-06-03 | Air & D - Sarl | Procede pour desodoriser des installations de grande surface |
WO2005059016A1 (fr) | 2003-12-10 | 2005-06-30 | Shell Internationale Research Maatschappij B.V. | Granules de soufre contenant un suppresseur de h2s |
US6987207B1 (en) * | 2005-03-03 | 2006-01-17 | Alan Jeffrey Ronyak | Hydrocarbonaceous composition |
EP1772158A2 (fr) * | 2005-10-06 | 2007-04-11 | Air & D- Sarl | Procédé du reduction des substances malodorantes dans citernes |
WO2009019041A1 (fr) | 2007-08-09 | 2009-02-12 | Air & D - Sarl | Procédé de réduction de l'odeur du bitume |
DE102007062314A1 (de) * | 2007-12-21 | 2009-06-25 | Air & D - Sarl | Verfahren zum Reduzieren von übelriechenden Substanzen in Tankbehältern |
-
2009
- 2009-12-08 EP EP09306195A patent/EP2338526A1/fr not_active Withdrawn
-
2010
- 2010-12-07 EP EP10814658A patent/EP2509642A1/fr not_active Withdrawn
- 2010-12-07 WO PCT/IB2010/003451 patent/WO2011070446A1/fr active Application Filing
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3960585A (en) | 1973-12-17 | 1976-06-01 | Shell Oil Company | Reducing H2 S-emission from hot cast sulfur-asphalt mixtures |
DE19725920A1 (de) * | 1996-06-25 | 1998-02-05 | Heresch & Heresch Umweltengine | Verfahren zur Geruchsneutralisation bei Asphaltmischanlagen |
EP1235768A1 (fr) | 1999-11-16 | 2002-09-04 | Alan Jeffrey Ronyak | Composition hydrocarbonee contenant des agents de suppression d'odeur |
WO2004045657A1 (fr) * | 2002-11-15 | 2004-06-03 | Air & D - Sarl | Procede pour desodoriser des installations de grande surface |
WO2005059016A1 (fr) | 2003-12-10 | 2005-06-30 | Shell Internationale Research Maatschappij B.V. | Granules de soufre contenant un suppresseur de h2s |
US6987207B1 (en) * | 2005-03-03 | 2006-01-17 | Alan Jeffrey Ronyak | Hydrocarbonaceous composition |
EP1772158A2 (fr) * | 2005-10-06 | 2007-04-11 | Air & D- Sarl | Procédé du reduction des substances malodorantes dans citernes |
WO2009019041A1 (fr) | 2007-08-09 | 2009-02-12 | Air & D - Sarl | Procédé de réduction de l'odeur du bitume |
DE102007037534A1 (de) * | 2007-08-09 | 2009-02-12 | Air & D - Sarl | Verfahren zu Geruchsverminderung bei Bitumen |
DE102007062314A1 (de) * | 2007-12-21 | 2009-06-25 | Air & D - Sarl | Verfahren zum Reduzieren von übelriechenden Substanzen in Tankbehältern |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018068728A1 (fr) * | 2016-10-12 | 2018-04-19 | Shell Internationale Research Maatschappij B.V. | Procédé de réduction d'odeurs de bitume et de crmb |
US11274208B2 (en) | 2016-10-12 | 2022-03-15 | Shell Oil Company | Reducing crumb rubber modified bitumen odors |
Also Published As
Publication number | Publication date |
---|---|
EP2338526A1 (fr) | 2011-06-29 |
EP2509642A1 (fr) | 2012-10-17 |
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