CA2720290C - Demulsifiers and methods for use in pharmaceutical applications - Google Patents

Demulsifiers and methods for use in pharmaceutical applications Download PDF

Info

Publication number: CA2720290C
Authority: CA; Canada
Prior art keywords: surfactant; demulsifier; ethylene oxide; propylene oxide; emulsion
Prior art date: 2008-04-02
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA2720290A

Other languages

English (en)

French (fr)

Other versions

CA2720290A1 (en

Inventor

Ruela Talingting-Pabalan

Manilal S. Dahanayake

Gary Woodward

Herve Adam

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Rhodia Operations SAS

Original Assignee

Rhodia Operations SAS

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2008-04-02

Filing date

2009-04-02

Publication date

2017-05-23

2008-08-13 Priority claimed from US12/191,130 external-priority patent/US7671099B2/en

2009-04-02 Application filed by Rhodia Operations SAS filed Critical Rhodia Operations SAS

2009-10-08 Publication of CA2720290A1 publication Critical patent/CA2720290A1/en

2017-05-23 Application granted granted Critical

2017-05-23 Publication of CA2720290C publication Critical patent/CA2720290C/en

Status Expired - Fee Related legal-status Critical Current

2029-04-02 Anticipated expiration legal-status Critical

Links

238000000034 method Methods 0.000 title claims abstract description 37
239000000839 emulsion Substances 0.000 claims abstract description 43
239000002736 nonionic surfactant Substances 0.000 claims abstract description 35
239000003945 anionic surfactant Substances 0.000 claims abstract description 29
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 26
150000003839 salts Chemical class 0.000 claims abstract description 19
229920001577 copolymer Polymers 0.000 claims abstract description 18
235000007586 terpenes Nutrition 0.000 claims abstract description 16
150000003505 terpenes Chemical class 0.000 claims abstract description 15
239000002253 acid Substances 0.000 claims abstract description 12
150000007513 acids Chemical class 0.000 claims abstract description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
239000004094 surface-active agent Substances 0.000 claims description 30
239000002904 solvent Substances 0.000 claims description 28
-1 olefin sulfonate Chemical class 0.000 claims description 26
125000004432 carbon atom Chemical group C* 0.000 claims description 17
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 13
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
150000008052 alkyl sulfonates Chemical class 0.000 claims description 9
235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 claims description 9
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 claims description 7
229910052708 sodium Inorganic materials 0.000 claims description 7
239000011734 sodium Substances 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 6
229920001400 block copolymer Polymers 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
150000002430 hydrocarbons Chemical class 0.000 claims description 4
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
150000001298 alcohols Chemical class 0.000 claims description 3
SVMUEEINWGBIPD-UHFFFAOYSA-N dodecylphosphonic acid Chemical compound CCCCCCCCCCCCP(O)(O)=O SVMUEEINWGBIPD-UHFFFAOYSA-N 0.000 claims description 3
NJGCRMAPOWGWMW-UHFFFAOYSA-N octylphosphonic acid Chemical group CCCCCCCCP(O)(O)=O NJGCRMAPOWGWMW-UHFFFAOYSA-N 0.000 claims description 3
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 3
239000003849 aromatic solvent Substances 0.000 claims description 2
YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical group [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 claims description 2
235000019387 fatty acid methyl ester Nutrition 0.000 claims description 2
150000002334 glycols Chemical class 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
125000002298 terpene group Chemical group 0.000 claims 1
235000014113 dietary fatty acids Nutrition 0.000 abstract description 17
239000000194 fatty acid Substances 0.000 abstract description 17
229930195729 fatty acid Natural products 0.000 abstract description 17
239000002202 Polyethylene glycol Substances 0.000 abstract description 11
229920001223 polyethylene glycol Polymers 0.000 abstract description 11
150000004665 fatty acids Chemical class 0.000 abstract description 10
125000000129 anionic group Chemical group 0.000 abstract description 3
239000012071 phase Substances 0.000 description 20
229940117927 ethylene oxide Drugs 0.000 description 17
239000000203 mixture Substances 0.000 description 17
239000007788 liquid Substances 0.000 description 16
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 9
CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
238000000605 extraction Methods 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
238000000926 separation method Methods 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
229930182555 Penicillin Natural products 0.000 description 4
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 4
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
238000009826 distribution Methods 0.000 description 4
229940049954 penicillin Drugs 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
125000000278 alkyl amino alkyl group Chemical group 0.000 description 3
125000004948 alkyl aryl alkyl group Chemical group 0.000 description 3
125000002877 alkyl aryl group Chemical group 0.000 description 3
125000003710 aryl alkyl group Chemical group 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000000356 contaminant Substances 0.000 description 3
LEOJDCQCOZOLTQ-UHFFFAOYSA-N dibutylcarbamothioyl n,n-dibutylcarbamodithioate Chemical compound CCCCN(CCCC)C(=S)SC(=S)N(CCCC)CCCC LEOJDCQCOZOLTQ-UHFFFAOYSA-N 0.000 description 3
239000012535 impurity Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
238000010979 pH adjustment Methods 0.000 description 3
229920001451 polypropylene glycol Polymers 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000000126 substance Substances 0.000 description 3
150000003871 sulfonates Chemical class 0.000 description 3
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000001335 aliphatic alkanes Chemical class 0.000 description 2
229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
229940072049 amyl acetate Drugs 0.000 description 2
PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
235000019445 benzyl alcohol Nutrition 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
235000010290 biphenyl Nutrition 0.000 description 2
125000006267 biphenyl group Chemical group 0.000 description 2
239000000872 buffer Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000000855 fermentation Methods 0.000 description 2
230000004151 fermentation Effects 0.000 description 2
MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 2
238000002156 mixing Methods 0.000 description 2
125000001624 naphthyl group Chemical group 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
239000003921 oil Substances 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
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 1
ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
241000233866 Fungi Species 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229920005628 alkoxylated polyol Polymers 0.000 description 1
150000004996 alkyl benzenes Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000002585 base Substances 0.000 description 1
238000010923 batch production Methods 0.000 description 1
230000003796 beauty Effects 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
239000000969 carrier Substances 0.000 description 1
ASOJLQIBBYOFDE-HCHBIZCOSA-N chembl2106443 Chemical compound C(/[C@H]1O[C@H]([C@H]([C@H]1O)O)[C@H](C)[C@H](OC)C(/C)=C/C=C/CNC(=O)[C@@H](CC)[C@]1(O)[C@@H]([C@H](O[C@H]2[C@@H]([C@H](OC)[C@H](O[C@H]3[C@@H]([C@H](O)[C@@H](OC)[C@H](C)O3)OC)[C@@H](C)O2)O)C(C)(C)[C@H](\C=C\C=C\C)O1)O)=C\C=C\C=C(/C)C(=O)C1=C(O)C=CN(C)C1=O ASOJLQIBBYOFDE-HCHBIZCOSA-N 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
HWQXBVHZYDELQG-UHFFFAOYSA-L disodium 2,2-bis(6-methylheptyl)-3-sulfobutanedioate Chemical compound C(CCCCC(C)C)C(C(C(=O)[O-])S(=O)(=O)O)(C(=O)[O-])CCCCCC(C)C.[Na+].[Na+] HWQXBVHZYDELQG-UHFFFAOYSA-L 0.000 description 1
JMGZBMRVDHKMKB-UHFFFAOYSA-L disodium;2-sulfobutanedioate Chemical compound [Na+].[Na+].OS(=O)(=O)C(C([O-])=O)CC([O-])=O JMGZBMRVDHKMKB-UHFFFAOYSA-L 0.000 description 1
229960000878 docusate sodium Drugs 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
229950003445 efrotomycin Drugs 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000013505 freshwater Substances 0.000 description 1
150000002314 glycerols Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
238000012994 industrial processing Methods 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
229920005684 linear copolymer Polymers 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
244000005700 microbiome Species 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000008213 purified water Substances 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000002344 surface layer Substances 0.000 description 1
238000011282 treatment Methods 0.000 description 1
229920003169 water-soluble polymer Polymers 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D17/00—Separation of liquids, not provided for elsewhere, e.g. by thermal diffusion
- B01D17/02—Separation of non-miscible liquids
- B01D17/04—Breaking emulsions
- B01D17/047—Breaking emulsions with separation aids

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Public Health (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Physics & Mathematics (AREA)
Thermal Sciences (AREA)
Dispersion Chemistry (AREA)
Medicinal Preparation (AREA)

CA2720290A 2008-04-02 2009-04-02 Demulsifiers and methods for use in pharmaceutical applications Expired - Fee Related CA2720290C (en)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US7276808P	2008-04-02	2008-04-02
US61/072,768		2008-04-02
US12/191,130 US7671099B2 (en)	2007-08-13	2008-08-13	Method for spearation crude oil emulsions
US12/191,130		2008-08-13
PCT/US2009/002056 WO2009123732A2 (en)	2008-04-02	2009-04-02	Demulsifiers and methods for use in pharmaceutical applications

Publications (2)

Publication Number	Publication Date
CA2720290A1 CA2720290A1 (en)	2009-10-08
CA2720290C true CA2720290C (en)	2017-05-23

Family

ID=43298738

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA2720290A Expired - Fee Related CA2720290C (en)	2008-04-02	2009-04-02	Demulsifiers and methods for use in pharmaceutical applications

Country Status (3)

Country	Link
EP (1)	EP2276468A4 (de)
CA (1)	CA2720290C (de)
WO (1)	WO2009123732A2 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2015157273A1 (en) *	2014-04-07	2015-10-15	U.S. Water Services, Inc.	Method and composition for increasing recovery of oil from fermentation processes

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0392697A3 (de) *	1989-04-12	1991-01-16	Petrolite Corporation	Demulgatoren zur Lösung von Emulsionen, die bei der Herstellung von Arzneimitteln gebildet werden
US5013452A (en) *	1989-06-23	1991-05-07	Petrolite Corporation	Resolution of emulsions formed in the production of pharmaceuticals
WO1993010756A1 (en) *	1991-11-25	1993-06-10	Richardson-Vicks, Inc.	Use of salicylic acid for regulating skin wrinkles and/or skin atrophy
US5670557A (en) *	1994-01-28	1997-09-23	Minnesota Mining And Manufacturing Company	Polymerized microemulsion pressure sensitive adhesive compositions and methods of preparing and using same
US7238744B2 (en) *	2002-04-12	2007-07-03	Daramic, Inc.	Ultrahigh molecular weight polyethylene articles and method of manufacture
US7501470B2 (en) *	2004-12-03	2009-03-10	Rhodia Inc.	Use of polyoxypropylene and polyoxyethylene terpene compounds in emulsion polymerization
CA2696312C (en) *	2007-08-13	2015-10-06	Rhodia, Inc.	Method for separating crude oil emulsions

2009
- 2009-04-02 WO PCT/US2009/002056 patent/WO2009123732A2/en not_active Ceased
- 2009-04-02 CA CA2720290A patent/CA2720290C/en not_active Expired - Fee Related
- 2009-04-02 EP EP09727655.4A patent/EP2276468A4/de not_active Withdrawn

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Publication number	Publication date
WO2009123732A2 (en)	2009-10-08
EP2276468A2 (de)	2011-01-26
EP2276468A4 (de)	2013-05-01
WO2009123732A3 (en)	2009-12-30
CA2720290A1 (en)	2009-10-08

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