WO2001012765A1 - Utilisation de composes terpeniques polyoxypropylenes/polyoxyetylenes comme agents de degraissage de surfaces dures - Google Patents
Utilisation de composes terpeniques polyoxypropylenes/polyoxyetylenes comme agents de degraissage de surfaces dures Download PDFInfo
- Publication number
- WO2001012765A1 WO2001012765A1 PCT/FR2000/002325 FR0002325W WO0112765A1 WO 2001012765 A1 WO2001012765 A1 WO 2001012765A1 FR 0002325 W FR0002325 W FR 0002325W WO 0112765 A1 WO0112765 A1 WO 0112765A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compound
- formula
- radical
- use according
- degreasing
- Prior art date
Links
- -1 polyoxypropylene Polymers 0.000 title claims abstract description 43
- 235000007586 terpenes Nutrition 0.000 title abstract description 6
- 238000005237 degreasing agent Methods 0.000 title description 2
- 229920001451 polypropylene glycol Polymers 0.000 title description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 75
- 238000005238 degreasing Methods 0.000 claims abstract description 40
- 229910052751 metal Inorganic materials 0.000 claims abstract description 12
- 239000002184 metal Substances 0.000 claims abstract description 12
- 150000003254 radicals Chemical class 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 239000004215 Carbon black (E152) Substances 0.000 claims description 14
- 229930195733 hydrocarbon Natural products 0.000 claims description 14
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- 238000004140 cleaning Methods 0.000 claims description 11
- 150000002431 hydrogen Chemical group 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 150000001340 alkali metals Chemical class 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000003129 oil well Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000006353 oxyethylene group Chemical group 0.000 abstract 1
- 150000003505 terpenes Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 16
- 239000000203 mixture Substances 0.000 description 11
- 150000001342 alkaline earth metals Chemical class 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000006260 foam Substances 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000002609 medium Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 239000003599 detergent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 4
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- ROKSAUSPJGWCSM-UWVGGRQHSA-N (-)-Nopol Chemical compound C1[C@@H]2C(C)(C)[C@H]1CC=C2CCO ROKSAUSPJGWCSM-UWVGGRQHSA-N 0.000 description 3
- ROKSAUSPJGWCSM-UHFFFAOYSA-N 2-(7,7-dimethyl-4-bicyclo[3.1.1]hept-3-enyl)ethanol Chemical compound C1C2C(C)(C)C1CC=C2CCO ROKSAUSPJGWCSM-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000007865 diluting Methods 0.000 description 3
- 150000004679 hydroxides Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 description 3
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000004115 Sodium Silicate Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 238000007306 functionalization reaction Methods 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000003165 hydrotropic effect Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 150000004686 pentahydrates Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 150000004760 silicates Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000019795 sodium metasilicate Nutrition 0.000 description 2
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 2
- 229910052911 sodium silicate Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910008433 SnCU Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- YDONNITUKPKTIG-UHFFFAOYSA-N [Nitrilotris(methylene)]trisphosphonic acid Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CP(O)(O)=O YDONNITUKPKTIG-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 229910052910 alkali metal silicate Inorganic materials 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- HJMZMZRCABDKKV-UHFFFAOYSA-N carbonocyanidic acid Chemical compound OC(=O)C#N HJMZMZRCABDKKV-UHFFFAOYSA-N 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229940005740 hexametaphosphate Drugs 0.000 description 1
- 239000000416 hydrocolloid Substances 0.000 description 1
- 230000002706 hydrostatic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- FBWNMEQMRUMQSO-UHFFFAOYSA-N tergitol NP-9 Chemical compound CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1 FBWNMEQMRUMQSO-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical class [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical class Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2003—Alcohols; Phenols
- C11D3/2006—Monohydric alcohols
- C11D3/2037—Terpenes
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
- C11D7/26—Organic compounds containing oxygen
- C11D7/263—Ethers
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
- C11D7/32—Organic compounds containing nitrogen
- C11D7/3227—Ethers thereof
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
- C23G1/00—Cleaning or pickling metallic material with solutions or molten salts
- C23G1/14—Cleaning or pickling metallic material with solutions or molten salts with alkaline solutions
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
- C11D2111/10—Objects to be cleaned
- C11D2111/14—Hard surfaces
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
- C11D2111/10—Objects to be cleaned
- C11D2111/14—Hard surfaces
- C11D2111/16—Metals
Definitions
- the subject of the present invention is the use of terpene compounds comprising oxypropylenated and oxyethylenated units, as degreasing / cleaning agents for hard surfaces, and more particularly for metallic surfaces.
- the field of cleaning / degreasing of metal surfaces requires very high performance, in particular with regard to the degreasing power of the composition used, as well as its ability not to create foam. It should also be noted that these results are often required when the conditions for implementation are very difficult. Thus, the spray methods are very favorable to the appearance of foam, because the treatment bath is applied under pressure.
- the compounds currently used in this field are essentially ethoxylated alkylphenols. These compounds intrinsically have very satisfactory degreasing properties. However, they have an important drawback, that of promoting the appearance of foam. This unacceptable phenomenon in this application is reduced by the addition of a defoaming agent, such as, for example, alkoxylated linear alcohols. However, the presence of this type of compound significantly decreases, and this definitively, the degreasing activity of ethoxylated alkylphenol. Indeed, it is not possible to compensate for the loss of activity by an additional addition of alkylphenol, so as to recover the initial level of activity.
- alkoxylated terpene compounds are described which are presented as good degreasers which do not favor the appearance of foam.
- the exemplified compounds are derived from terpene compounds of the nopol or arbanol type, and comprise 0 to 2 oxypropylenated units and 3.3 to 10.3 oxyethylenated units.
- the object of the present invention is to propose using a particular terpene compound, satisfying the double criterion mentioned above, in the application of cleaning / degreasing of hard surfaces and in particular of metallic surfaces, and this, at low concentrations.
- the subject of the present invention is the use for cleaning degreasing of hard surfaces, of at least one compound, used with a concentration of between 0.01 and 10 g / l, when using this last, with the following formula:
- X represents -CH 2 -C (Ri) (R2) -O- or -O-CH (R'i) -CH (R'2) -O- in which: - R 1 , R 2 , R ' 1 and R' 2 , identical or different, represent hydrogen or a hydrocarbon radical, saturated or unsaturated, linear, branched or cyclic, C 1 -C 22 , preferably
- R3 and R 4 identical or different, represent hydrogen or a hydrocarbon radical, saturated or unsaturated, linear, branched or cyclic, C1-C22. provided that at least one of the radicals R3 or R4 is different from hydrogen;
- - R5 represents hydrogen, a hydrocarbon radical, saturated or not, linear, branched or cyclic, aromatic or not, C1-C22, optionally substituted, or a group chosen from the following: -SO3M
- - n is a whole number or not, between 3 and 5 inclusive;
- - p is an integer or not between 6 and 10, the limits being excluded.
- a first type of compound is defined by the formula (I) in which X is equal to -CH 2 -C (Ri) (R2) -O-.
- compound (la) corresponds to the following formula: Z-CH 2 -C (Ri) (R2) -O- [CH (R3) -CH (R4) -O] n- [ CH 2 CH2-0] p-R5
- the radical Z is chosen from the radicals of formulas c) to g). It should be noted that the radical Z is more particularly attached to the rest of the chain via any of the carbon atoms 1 to 6; carbon atoms 1, 5 and 6 being preferred. Furthermore, the radical Z can be substituted on at least one of its carbon atoms, by two C1-C6 alkyl radicals, preferably two methyl radicals.
- carbon 7 is substituted by these two alkyl radicals, more precisely two methyls.
- One of the preferred compounds of the invention therefore consists of a compound whose radical Z corresponds to one of those appearing in FIG. C) to g), and more preferably, the radicals d) and e) ; the radical Z being substituted by two methyl radicals, located on carbon 7
- the radical Z corresponds to formulas d) or e), attached to the rest of the chain by carbon 5 or 1, and carrying two methyl substituents on carbon 7.
- R1, R2, identical or not represent a hydrogen, or a methyl radical.
- R 1 , R represent a hydrogen atom.
- radicals R3 and R 4 identical or different, represent hydrogen or a hydrocarbon radical, saturated or unsaturated, linear, branched or cyclic, C-
- said radicals represent hydrogen or a C 1 -C 4 alkyl radical, preferably the methyl radical or the ethyl radical, provided that at least one of these two radicals is different from hydrogen.
- one of the radicals represents hydrogen, the other a methyl radical.
- R 5 represents hydrogen, a hydrocarbon radical, saturated or not, linear, branched or cyclic, aromatic or not, optionally substituted, with C-1-C22, or a group chosen from -SO3M, -OP ⁇ 3 (M) 2 , - (CH2) r COOM, - (CH 2 ) z -S ⁇ 3lv1; formulas in which:
- * M represents hydrogen, an alkali metal or an ammonium function N (R) 4 + , in which R, identical or not, represent hydrogen or a hydrocarbon radical, saturated or not, linear, branched or cyclic, in C1 -C22, preferably Ci-C ⁇ - optionally hydroxylated; * r is between 1 and 6;
- R5 is a hydrocarbon radical
- the latter is more particularly a C1-C6 alkyl radical, or an alkylphenyl radical, optionally substituted by a halogen (such as chlorine for example).
- R 5 is a hydrogen atom.
- n is a whole number or not, between 3 and 5 inclusive and p is a whole number or not, between 6 and 10, the limits being excluded. According to a first particular embodiment of the present invention, the value of n is 3.
- n is between 6.2 and 7, limits included.
- p is between 6.3 and 7, limits included.
- n is between 6.2 and 7, limits included.
- the value of p is preferably between 7 inclusive and 10 excluded, preferably between 8 inclusive and 10 excluded.
- a second type of compound is defined by the formula (I) in which X represents -O-CH (R'i) -CH (R'2) -O-.
- radical Z is more particularly attached to the rest of the chain via any of the carbon 1 to 6.
- the carbon atoms 1, 3, 4 or 6 are more particularly retained .
- the radical Z can be substituted on at least one of its carbon atoms, by two C-i-C ⁇ alkyl radicals, preferably two methyl radicals.
- carbon 7 is substituted by these two alkyl radicals, more precisely two methyls.
- radical Z relates to one of the carbon atoms 2 or 5, a C-i-C ⁇ alkyl substituent, preferably a methyl radical.
- radicals R “i and R'2 identical or different, represent hydrogen or a hydrocarbon radical, saturated or unsaturated, linear, branched or cyclic, in C1-C22, provided that one of the two is different from hydrogen
- said radicals represent hydrogen or a C1-C6 alkyl radical, preferably the methyl radical.
- a particularly advantageous embodiment of the present invention consists of the use of the compounds of type (la) described above.
- the compounds according to the invention can be prepared by reacting: for obtaining compounds (la), a reagent of formula (Ha) R1 / Z-CH2-C-OH ⁇
- the radicals Z, R1, R 2 , R3 and R 4 have been defined previously.
- the reaction can also be carried out in the presence of a catalyst.
- R identical or not, represent hydrogen or a C1-C6 alkyl radical, preferably methyl, ethyl.
- the sodium, potassium and tetramethylammonium hydroxides are suitable for carrying out this reaction.
- catalysts chosen from alkoxides of alkali or alkaline-earth metals, such as, for example, sodium or potassium methylate, ethylate, tert-butoxide. It should be noted that it is also possible to use, as catalyst, primary, secondary or tertiary amines, preferably aliphatic amines, these amines being able to comprise other functions such as in particular ether functions. As an example of a catalyst of this type, mention may be made of
- the amount is more particularly between 0.5 and 40 mg relative to the weight of final product. It is possible to carry out this reaction in the presence of an acid of
- the amount of acid catalyst varies more particularly between 0.1 and 10 mmol per mole of reagent (11a) or (11b).
- the contacting is carried out at a temperature sufficient to allow the reaction to be carried out.
- the temperature is above 100 ° C, more particularly between 120 and 250 ° C, and preferably between 150 and 200 ° C.
- the reaction is carried out under an inert atmosphere under the reaction conditions, such as nitrogen, or a rare gas such as argon or even carbon monoxide. Nitrogen is preferred.
- the reaction can take place at atmospheric pressure, under reduced pressure or with slight suppression. Usually, it is preferred to work under a pressure of between 1 and 4 bar.
- the amounts of the compounds (IIIll) and (IIIll) are calculated as a function of the characteristics of the formula (I), more particularly the desired values of n and p.
- the reaction mixture is preferably neutralized, in order to obtain a pH of between 5 and 8, preferably 6 and 7.
- Neutralization is carried out using acetic acid, or hydroxide, sodium carbonate or bicarbonate, depending on the nature of the catalyst involved in the reaction.
- the compound (I) is such that the radical R5 is hydrogen.
- the compounds according to the invention can be used in the metal processing industry, but also in any application in which a degreasing of such surfaces is implemented such as the degreasing of wells or oil exploitation platforms.
- the compound used according to the invention is used with an amount of between 0.01 and 10 g / l, at the time of use.
- the concentration of compound is more particularly between 0.01 and 5 g / l during use.
- the concentration of compounds is between 0.01 and 10 g / l at the time of use, in compounds used according to the invention .
- the compound according to the invention is used with a concentration preferably of between 0.01 and 5 g / l.
- aqueous degreasing or detergent media containing the compounds according to the invention are preferably used at a temperature at least of the order of their cloud temperature.
- the degreasing formulations of metal sheets or plates in an alkaline medium include, in addition to the compound used according to the invention, an alkaline detergent comprising at least one of the following compounds:
- At least one agent controlling the pH such as hydroxides, carbonates, sesquicarbonates, bicarbonate of alkali or alkaline earth metals,
- - at least one polyphosphate such as tripolyphosphate, pyrophosphate, orthophosphate, hexametaphosphate of alkali metal, alkaline earth metal, ammonium type N (R 4 ) + with R representing hydrogen, an alkyl radical in C 1 -C 4 optionally comprising an oxygen atom, - at least one alkali metal silicate, such as for example the alkali metal metasilicates, anhydrous or not, or their mixtures.
- polyphosphate such as tripolyphosphate, pyrophosphate, orthophosphate, hexametaphosphate of alkali metal, alkaline earth metal, ammonium type N (R 4 ) + with R representing hydrogen, an alkyl radical in C 1 -C 4 optionally comprising an oxygen atom, - at least one alkali metal silicate, such as for example the alkali metal metasilicates, anhydrous or not, or their mixtures.
- the concentration of alkaline detergent during use is between 1 and 100 g / l, more particularly between 5 and 20 g / l.
- the formulations can also comprise: at least one hydrotropic electrolyte such as benzenesulfonates, mono- or di (C1-C4) benzenesulfonates, toluene-, xylene- or cumene-sulfonates, alcohols and glycols, at least one sequestering agent such as nitriloacetic acid, ethylenediamine tetraacetic acid, ethylenediamine tetramethylphosphonic acid, nitrilo-trimethylene phosphonic acid or their salts,
- at least one hydrotropic electrolyte such as benzenesulfonates, mono- or di (C1-C4) benzenesulfonates, toluene-, xylene- or cumene-sulfonates, alcohols and glycols
- at least one sequestering agent such as nitriloacetic acid, ethylenediamine tetraacetic acid, ethylened
- - buffering agents such as alkanolamines, ethylenediamine, - agents inhibiting corrosion of metals.
- concentrations of these compounds vary within the usual ranges of the field. However, by way of illustration, the content of each of the compounds varies from 0 to 1.5 g / l at the time of use.
- aqueous compositions used for degreasing petroleum platforms can comprise, in addition to the compound according to the invention:
- At least one hydrotropic electrolyte such as benzenesulfonates, mono- or di-alkyl (C1-C4) benzenesulfonates, toluene-, xylene- or cumene-sulfonates, alccols and glycols,
- At least one agent controlling the pH such as, for example, carbonates, sesquicarbonates, bicarbonates of alkali metals,
- the aqueous media used for cleaning the oil wells can comprise, in addition to the compound according to the invention:
- At least one agent making it possible to adjust the pH such as, for example, carbonates, sesquicarbonates, bicarbonates of alkali metals, hydroxides of alkali or alkaline-earth metals, - additives such as enzymes in quantities which can range up to 5% of the total weight of the aqueous composition, of metal corrosion inhibiting agents,
- weighting agents so as to maintain a satisfactory hydrostatic pressure in the well.
- soluble or at least partially soluble salts such as the halides of alkali or alkaline-earth metals. It is also possible to use sulfates, carbonates, bicarbonates, silicates, phosphates of alkali or alkaline earth metals, alone or as a mixture. It is also possible to use salts of organic acids, such as formates, acetates of alkali or alkaline earth metals. It is possible to use, although not preferred, insoluble salts such as sulfates, silicates or carbonates of alkaline earth metals; alkaline earth metal or zinc bromides. - hydrocolloids such as polysaccharides of plant origin, such as polygalactomannans, cellulose, starches and their derivatives; polysaccharides of bacterial origin such as xanthan gum or deacetylated derivatives.
- surfactants anionic, cationic, zwiterrionic, amphoteric
- low foaming agents preferably low foaming agents
- This example relates to the synthesis of 6,6-dimethylbicyclo [3.1.1] hept-2-ene-2 ethanol comprising oxypropylenated units (OP) and oxyethylenated units (OE).
- OP oxypropylenated units
- OE oxyethylenated units
- the 6,6-dimethylbicyclo [3.1.1] hept-2-ene-2 ethanol (nopol) used is sold by the company Fluka.
- the nopol (6 moles) and an aqueous solution of potassium hydroxide (50%, 3.1 g) are introduced.
- the reaction medium is dehydrated at 120 ° C. under a stream of nitrogen. Then heated to 170 ° C and introduced with propylene oxide (x molar equivalents). Once the propylene oxide has been introduced, ethylene oxide (y molar equivalents) is added.
- the purpose of this example is to compare the degreasing properties of the compounds according to the invention 1 and 3, of the comparative compounds 10, 11 and 12, as well as those obtained with the defoamed Igepal NP10.
- Pre-degreased steel plates of the "Q-Panel" brand Stock n ° R-36 type "Dull matt finish" of 0.8 x 76 x 152 mm are immersed for 2 minutes in a whole lubricating oil formulated for the rolling of steel sheets for automobiles, brand QUAKER 6130 N from Quaker Chemicals, then suspended for 24 hours draining.
- the greased plates are introduced into a CIEMME LARO 350 spray degreasing machine.
- the degreasing temperature is 45 ° C and the pressure is 2 bar.
- a basic degreasing medium is prepared (pH 12-13) by diluting in water 20 g / l of an aqueous detergent containing 45% by weight of active material consisting of equal weight amounts of potassium hydroxide, sodium metasilicate (SIMET GA5, granules of anhydrous metasilicate and metasilicate pentahydrate, marketed by Rhodia Chimie) and of tetrapotassium pyrophosphate, and addition of 1 g / l of the compound to be tested.
- an aqueous detergent containing 45% by weight of active material consisting of equal weight amounts of potassium hydroxide, sodium metasilicate (SIMET GA5, granules of anhydrous metasilicate and metasilicate pentahydrate, marketed by Rhodia Chimie) and of tetrapotassium pyrophosphate, and addition of 1 g / l of the compound to be tested.
- the degreasing time is the time necessary to achieve complete covering of both sides with a continuous film of water.
- Igepal defoamed is a mixture of Igepal CO-660 (nonyphenol 10 OE) and Miravon B12DF (50/50)
- the product according to the invention is always more active than the agents used. implemented for comparison.
- the purpose of this example is to compare the degreasing properties of the compounds according to the invention 4 to 7, as well as those obtained with the Igepal NP9 which has not been defoamed.
- Pennzoil 80W-90 brand oil sold by Pennzoil Products
- the quantity of oil is measured by weighing the plate before and after applying the oil. - Cleaning and rinsing
- the plate is immersed in one liter of degreasing medium, with magnetic stirring (100 rpm), at 50 ° C for 10 minutes.
- the plates are rinsed under a stream of running water 2 ml / min for 5 seconds on each side, then dried at 80 ° C.
- the measurement of the effectiveness of the operation is calculated by weighing the plate before and after treatment with the degreasing medium.
- a basic degreasing medium is prepared (pH 12-13) by diluting in water 20 g / l of an aqueous detergent containing 1.5 g / l of tetrapotassium pyrophosphate, and adding 1 g / l of the compound to be tested.
- Igepal is an Igepal CO-630 which is a nonylphenol 9 OE.
- the purpose of this example is to compare the foaming properties of the compounds obtained in Examples 1 to 9, as well as those obtained with the comparative compounds Igepal defoamed, Igepal alone.
- a basic degreasing medium is prepared (pH 12-13) by diluting in water 20 g / l of an aqueous detergent containing 45% by weight of active material consisting of equal weight amounts of potassium hydroxide, sodium metasilicate (SIMET GA5, granules of anhydrous metasilicate and metasilicate pentahydrate, marketed by Rhodia Chimie) and tetrapotassium pyrophosphate and addition of 1 g / l of the test compound.
- SIMET GA5 sodium metasilicate
- granules of anhydrous metasilicate and metasilicate pentahydrate marketed by Rhodia Chimie
- tetrapotassium pyrophosphate tetrapotassium pyrophosphate
- the test is carried out at 50 ° C.
- the foam is obtained by stirring 900 g of solution using a turbine agitator (40mm turbine, speed 2000 rpm) for 5 minutes.
- the foam level is read in a test tube after 5 minutes of rest.
- Igepal defoamed is a mixture of Igepal CO-660 (nonyphenol 10 OE) and Miravon B12DF (50/50).
- Igepal Igepal CO-660 (nonyphenol 10 OE).
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Metallurgy (AREA)
- Mechanical Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Materials Engineering (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cleaning And De-Greasing Of Metallic Materials By Chemical Methods (AREA)
- Polyethers (AREA)
- External Artificial Organs (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Materials For Medical Uses (AREA)
- Lubricants (AREA)
Abstract
Description
Claims
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
MXPA02001589A MXPA02001589A (es) | 1999-08-17 | 2000-08-16 | Uso de compuestos de polioxipropileno/polioxietilenterpeno como agentes desengrasantes para superficies duras. |
BRPI0013362-0A BR0013362B1 (pt) | 1999-08-17 | 2000-08-16 | utilização de pelo menos um composto terpênico nas aplicações de desengorduramento/limpeza de superfìcies duras. |
DE60009721T DE60009721T2 (de) | 1999-08-17 | 2000-08-16 | Verwendung von polyoxypropylenierten/polyoxyethlenierten Terpenderivaten als Entfettungsmittel von harten Oberflächen |
CA002382093A CA2382093C (fr) | 1999-08-17 | 2000-08-16 | Utilisation de composes terpeniques polyoxypropylenes/polyoxyetylenes comme agents de degraissage de surfaces dures |
AT00958691T ATE263826T1 (de) | 1999-08-17 | 2000-08-16 | Verwendung von polyoxypropylenierten/polyoxyethylenierten terpenderivaten als entfettungsmittel von harten oberflächen |
AU70135/00A AU759508B2 (en) | 1999-08-17 | 2000-08-16 | Use of polyoxypropylene/polyoxyethylene terpene compounds as degreasing agents for hard surfaces |
JP2001517651A JP3983543B2 (ja) | 1999-08-17 | 2000-08-16 | ポリオキシプロピレン/ポリオキシエチレンテルペン化合物の、硬質表面用脱脂剤としての使用 |
EP00958691A EP1206512B1 (fr) | 1999-08-17 | 2000-08-16 | Utilisation de composes terpeniques polyoxypropylenes/polyoxyethylenes comme agents de degraissage de surfaces dures |
US11/273,012 US20060079426A1 (en) | 1999-08-17 | 2005-11-14 | Use of polyoxypropylene/polyoxyethylene terpene compounds as degreasing agents for hard surfaces |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9910559A FR2797643B1 (fr) | 1999-08-17 | 1999-08-17 | Utilisation composes terpeniques polyoxypropylenes/ polyoxyethylenes comme agent de degraissage de surfaces dures |
FR99/10559 | 1999-08-17 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10049575 A-371-Of-International | 2002-05-15 | ||
US10/820,929 Continuation US20040198624A1 (en) | 1999-08-17 | 2004-04-08 | Use of polyoxypropylene/polyoxyethylene terpene compounds as degreasing agents for hard surfaces |
Publications (1)
Publication Number | Publication Date |
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WO2001012765A1 true WO2001012765A1 (fr) | 2001-02-22 |
Family
ID=9549189
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2000/002325 WO2001012765A1 (fr) | 1999-08-17 | 2000-08-16 | Utilisation de composes terpeniques polyoxypropylenes/polyoxyetylenes comme agents de degraissage de surfaces dures |
Country Status (14)
Country | Link |
---|---|
EP (1) | EP1206512B1 (fr) |
JP (1) | JP3983543B2 (fr) |
KR (1) | KR100588273B1 (fr) |
CN (1) | CN1185328C (fr) |
AT (1) | ATE263826T1 (fr) |
AU (1) | AU759508B2 (fr) |
BR (1) | BR0013362B1 (fr) |
CA (1) | CA2382093C (fr) |
DE (1) | DE60009721T2 (fr) |
DK (1) | DK1206512T3 (fr) |
ES (1) | ES2214310T3 (fr) |
FR (1) | FR2797643B1 (fr) |
MX (1) | MXPA02001589A (fr) |
WO (1) | WO2001012765A1 (fr) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011018366A1 (fr) | 2009-08-13 | 2011-02-17 | Rhodia Operations | Composition de nettoyage de graffiti |
WO2011036053A1 (fr) | 2009-09-28 | 2011-03-31 | Rhodia Operations | Dispersion d'un polymère hydrosoluble dans un milieu liquide |
US8765021B2 (en) | 2008-04-09 | 2014-07-01 | Rhodia Operations | Aqueous treatment composition for inhibiting corrosion and acid attack on metallic surfaces |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2918994B1 (fr) * | 2007-07-20 | 2012-10-19 | Rhodia Operations | Formulations de diesters d'acide carboxylique et leur utilisation pour le traitement de materiaux. |
CN101993790B (zh) * | 2009-08-17 | 2012-06-06 | 中国石油化工股份有限公司 | 炼油装置的清洗剂及其制备方法 |
KR101673589B1 (ko) * | 2009-10-30 | 2016-11-07 | 동우 화인켐 주식회사 | 평판표시장치의 유리기판용 세정제 조성물 |
PE20171646A1 (es) | 2014-12-02 | 2017-11-13 | Minerva Neurosciences Inc | Composiciones que comprenden 2-((1-(2(4-fluorofenil)-2-oxoetil)piperidin-4-il)metil)isoindolin-1-ona para tratar la esquizofrenia |
US11466225B2 (en) | 2018-03-06 | 2022-10-11 | Shrieve Chemical Products, Inc. | Lubricant and refrigerant compositions comprising polyalkylene glycols and uses thereof |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1996001245A1 (fr) * | 1994-07-01 | 1996-01-18 | Rhone Poulenc Chimie | Derives terpeniques polyalcoxyles et compositions en contenant |
FR2757508A1 (fr) * | 1996-12-20 | 1998-06-26 | Rhodia Chimie Sa | Composes terpeniques polyalcoxyles, leur procede de preparation et leur utilisation comme agents demoussants |
-
1999
- 1999-08-17 FR FR9910559A patent/FR2797643B1/fr not_active Expired - Lifetime
-
2000
- 2000-08-16 CN CNB008132046A patent/CN1185328C/zh not_active Expired - Lifetime
- 2000-08-16 JP JP2001517651A patent/JP3983543B2/ja not_active Expired - Lifetime
- 2000-08-16 KR KR1020027002017A patent/KR100588273B1/ko active IP Right Grant
- 2000-08-16 MX MXPA02001589A patent/MXPA02001589A/es active IP Right Grant
- 2000-08-16 DE DE60009721T patent/DE60009721T2/de not_active Expired - Lifetime
- 2000-08-16 BR BRPI0013362-0A patent/BR0013362B1/pt not_active IP Right Cessation
- 2000-08-16 WO PCT/FR2000/002325 patent/WO2001012765A1/fr active IP Right Grant
- 2000-08-16 AT AT00958691T patent/ATE263826T1/de active
- 2000-08-16 CA CA002382093A patent/CA2382093C/fr not_active Expired - Lifetime
- 2000-08-16 DK DK00958691T patent/DK1206512T3/da active
- 2000-08-16 AU AU70135/00A patent/AU759508B2/en not_active Expired
- 2000-08-16 ES ES00958691T patent/ES2214310T3/es not_active Expired - Lifetime
- 2000-08-16 EP EP00958691A patent/EP1206512B1/fr not_active Expired - Lifetime
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1996001245A1 (fr) * | 1994-07-01 | 1996-01-18 | Rhone Poulenc Chimie | Derives terpeniques polyalcoxyles et compositions en contenant |
FR2757508A1 (fr) * | 1996-12-20 | 1998-06-26 | Rhodia Chimie Sa | Composes terpeniques polyalcoxyles, leur procede de preparation et leur utilisation comme agents demoussants |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8765021B2 (en) | 2008-04-09 | 2014-07-01 | Rhodia Operations | Aqueous treatment composition for inhibiting corrosion and acid attack on metallic surfaces |
WO2011018366A1 (fr) | 2009-08-13 | 2011-02-17 | Rhodia Operations | Composition de nettoyage de graffiti |
WO2011036053A1 (fr) | 2009-09-28 | 2011-03-31 | Rhodia Operations | Dispersion d'un polymère hydrosoluble dans un milieu liquide |
Also Published As
Publication number | Publication date |
---|---|
DE60009721T2 (de) | 2005-03-31 |
BR0013362A (pt) | 2002-04-30 |
KR100588273B1 (ko) | 2006-06-09 |
BR0013362B1 (pt) | 2010-11-03 |
ES2214310T3 (es) | 2004-09-16 |
EP1206512A1 (fr) | 2002-05-22 |
DE60009721D1 (de) | 2004-05-13 |
AU759508B2 (en) | 2003-04-17 |
FR2797643B1 (fr) | 2003-06-06 |
CA2382093C (fr) | 2005-10-25 |
KR20020019984A (ko) | 2002-03-13 |
AU7013500A (en) | 2001-03-13 |
JP2003507531A (ja) | 2003-02-25 |
MXPA02001589A (es) | 2002-07-02 |
DK1206512T3 (da) | 2004-06-07 |
CN1376193A (zh) | 2002-10-23 |
CA2382093A1 (fr) | 2001-02-22 |
EP1206512B1 (fr) | 2004-04-07 |
JP3983543B2 (ja) | 2007-09-26 |
FR2797643A1 (fr) | 2001-02-23 |
ATE263826T1 (de) | 2004-04-15 |
CN1185328C (zh) | 2005-01-19 |
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