EP2185629A2 - Alkoxylierte phosphorsäuretriester mit hohem alkoxylierungsgrad - Google Patents
Alkoxylierte phosphorsäuretriester mit hohem alkoxylierungsgradInfo
- Publication number
- EP2185629A2 EP2185629A2 EP08785169A EP08785169A EP2185629A2 EP 2185629 A2 EP2185629 A2 EP 2185629A2 EP 08785169 A EP08785169 A EP 08785169A EP 08785169 A EP08785169 A EP 08785169A EP 2185629 A2 EP2185629 A2 EP 2185629A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- units
- carbon atoms
- formula
- branched
- phosphoric acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 title claims abstract description 36
- -1 phosphoric acid triesters Chemical class 0.000 title claims abstract description 25
- 229910000147 aluminium phosphate Inorganic materials 0.000 title claims abstract description 21
- 150000002191 fatty alcohols Chemical class 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 150000005691 triesters Chemical class 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 4
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 claims description 4
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 claims description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 101500021084 Locusta migratoria 5 kDa peptide Proteins 0.000 claims description 2
- BTFJIXJJCSYFAL-UHFFFAOYSA-N arachidyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 2
- 229960000735 docosanol Drugs 0.000 claims description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 2
- 230000008719 thickening Effects 0.000 abstract description 3
- 235000011007 phosphoric acid Nutrition 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920000137 polyphosphoric acid Polymers 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- AFINAILKDBCXMX-PBHICJAKSA-N (2s,3r)-2-amino-3-hydroxy-n-(4-octylphenyl)butanamide Chemical compound CCCCCCCCC1=CC=C(NC(=O)[C@@H](N)[C@@H](C)O)C=C1 AFINAILKDBCXMX-PBHICJAKSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000013011 aqueous formulation Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910010165 TiCu Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000008406 cosmetic ingredient Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229940045860 white wax Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/86—Polyethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
- C08G65/327—Polymers modified by chemical after-treatment with inorganic compounds containing phosphorus
Definitions
- the invention relates to phosphoric acid triesters derived from alkoxylated fatty alcohols having more than 50 alkoxy groups.
- Phosphoric acid esters are toxicologically and ecotoxicologically harmless, skin-friendly due to their neutral pH values and well suited for use in cosmetic formulations.
- Alkyl or Alkenylphosphosphorklarester are usually prepared by condensation of fatty alcohols with diphosphorus pentoxide or orthophosphoric acid, with mixtures of mono- / di- / triesters are obtained with a major proportion of mono- and diesters.
- JP 09-268193 describes a method for the preparation of phosphoric acid triesters wherein phosphorus oxychloride is reacted with a fatty alcohol or an alkoxylated fatty alcohol in the presence of a catalyst selected from TiCu, MgCl 2 or AICI 3 .
- Phosphoric acid triesters are obtained which can carry up to 50 -CH 2 CH 2 O units (EO).
- EO -CH 2 CH 2 O units
- These ethoxylated phosphoric acid esters can be used advantageously as thickeners.
- their disadvantage is their low water solubility and difficult processibility to aqueous formulations.
- phosphoric acid triesters are sought, which have no production-related chlorine-containing impurities.
- the present invention therefore provides phosphoric acid triesters of the formula (I)
- Ri, R 2 and R 3 may be the same or different and is a linear or branched, saturated alkyl group having 6 to 30, preferably 8 to 22 and particularly preferably 12 to 18 carbon atoms, for a linear or branched, mono- or polyunsaturated alkenyl group with 6 to 30, preferably 8 to 22 and particularly preferably 12 to 18 carbon atoms, or an aryl group, in particular a phenyl group substituted with 1 to 3 branched alkyl groups, each independently 3 to 18 and preferably 4 to 12 carbon atoms substituted each group (OAi) x , (A2 ⁇ ) y and (A 3 O) Z are each independently selected from units selected from CH 2 CH 2 O, C 3 H 6 O and C 4 HeO, and wherein Units CH 2 CH 2 O, C 3 H 6 O and C 4 HeO within the individual groups (OAi) x , (A 2 O) y and (A 3 O) 2 may be arranged block-wise or randomly distributed, and Each of x, y
- the units OA ⁇ OA 2 and OA 3 in the phosphoric acid esters of the formula (I) mean CH 2 CH 2 O.
- the radicals Rr (OAi) x , R 2 - (OA 2 ) y and R 3 - (OA 3 ) Z in the Phosphorklam of formula (I) derived from fatty alcohol ethoxylates selected from fatty alcohol ethoxylates having 51 to 200 EO units ( EO CH 2 CH 2 O), preferably with 55 to 150 EO units and particularly preferably with 60 to 100 EO units, where the respective fatty alcohol radical RiO-, R 2 O- and R 3 O- is derived from alcohols selected from Octanol, decanol, dodecanol, tetradecanol, hexadecanol, octadecanol, eicosanol, behenyl alcohol, fatty alcohols having C-chain sections between 8 and 22, preferably Ci 0 / Ci 2 fatty alcohol, C 12 / Ci 4 fatty alcohol, Ci 2 / Ci 5 Fatty alcohol and Ci 6 / Ci 8 fatty alcohol
- the groups (OAi) x , (OA 2 ) y and (OA 3 ) Z in the phosphoric acid triesters of the formula (I) are each composed of CH 2 CH 2 O and C 3 HeO units, where the CH 2 CH 2 O and C 3 H 6 O units within the individual groups (OAi) x , (OA 2 ) y and (OA 3 ) Z may be arranged block-wise or randomly distributed, and contain in each case 51 to 199, preferably 55 to 150 and particularly preferably 60 to 100 CH 2 CH 2 O units and 1 to 20, preferably 1 to 10 and particularly preferably 2 to 5 C 3 H 6 ⁇ units.
- the phosphoric acid triesters of the formula (I) can preferably be prepared by reacting phosphoric acid or phosphoric acid derivatives with alkoxylated fatty alcohols, the alkoxylated fatty alcohols bearing at least 51 alkoxy groups.
- the preparation of the phosphoric acid esters of the formula (I) is particularly preferably carried out by reacting phosphoric acid or a phosphoric acid derivative selected from Orthophosphorklare, Tetraphosphordecaoxid, polyphosphoric acid, phosphorus oxychloride or phosphorus pentachloride with fatty alcohol alkoxylates at temperatures between 150 and 250 0 C, preferably between 180 and 240 0 C and in particular preferably between 200 and 230 ° C.
- the preparation of the phosphoric acid esters of the formula (I) is particularly preferably carried out by reaction of orthophosphoric acid, polyphosphoric acid or tetraphosphorodecoxide and, most preferably, by reaction of orthophosphoric acid with fatty alcohol alkoxylates.
- phosphoric acid triesters of the formula (I) which are chlorine-free are obtained. This means in particular that they contain no chlorine impurities.
- the phosphoric acid esters of the formula (I) are chlorine-free.
- the phosphoric acid triesters of the formula (I) may advantageously also be present together with other phosphoric acid esters in mixtures.
- a further subject of the present invention are therefore mixtures comprising one or more phosphoric triesters of the formula (I) and one or more phosphoric esters of the formula (II) (A 2 O) W R 5
- Ri is a linear or branched, saturated alkyl group having 6 to 30, preferably 8 to 22 and particularly preferably 12 to 18 carbon atoms, for a linear or branched, mono- or polyunsaturated alkenyl group having 6 to 30, preferably 8 to 22 and particularly preferably 12 to 18 carbon atoms, or an aryl group, in particular a phenyl group which may be substituted by 1 to 3 branched alkyl groups, each of which independently contains 3 to 18 and preferably 4 to 12 carbon atoms, is
- R 4 is H, Li + , Na + , K + , Mg ++ , Ca ++ , Al +++ , NH 4 + or quaternary
- R a, R b and R c are independently hydrogen, a linear or branched alkyl group having 1 to 22 carbon atoms, a linear or branched, mono- or polyunsaturated alkenyl group having 2 to 22 Carbon atoms, a linear mono-hydroxyalkyl group having 2 to 10 carbon atoms, preferably a mono-
- Hydroxyethyl or mono-hydroxypropyl group or a linear or branched dihydroxyalkyl group having 3 to 10 carbon atoms,
- R 5 has the meaning of Ri or R 4
- the individual groups (OAi) x and (A 2 O) w each independently consist of units selected from CH 2 CH 2 O, C 3 H 6 O and C 4 H 8 O and wherein the units CH 2 CH 2 O, C 3 H 6 O and C 4 H 8 O within the individual groups (OAi) x and (A 2 O) w can be arranged block-wise or randomly distributed,
- x is a number from 51 to 200, preferably from 55 to 150 and particularly preferably from 60 to 100, and
- w is 0 or a number from 51 to 200, preferably from 55 to 150 and particularly preferably from 60 to 100.
- Preferred mixtures according to the invention consist of the compounds of the formula (I) and (II).
- the amount of phosphoric triesters according to formula (I) is preferably greater than 80.0% by weight, more preferably from 82.0 to 95.0% by weight and particularly preferably from 85.0 to 89.0 wt .-%, based on the total weight of the phosphoric acid ester according to formula (I) and formula (II).
- the degree of neutralization of the non-esterified phosphorus valencies (P-OH) in the phosphoric esters according to formula (II) can be between 0 and 100%.
- the remaining free valencies on the phosphorus atom may be acid groups, but also counterions selected from Li + , Na + , K + , Mg ++ , Ca ++ , Al +++ , NH 4 + , quaternary ammonium ions [HNR a R b R c ] + , wherein R a , R b and R c are independently hydrogen, a linear or branched alkyl group having 1 to 22 carbon atoms, a linear or branched, mono- or polyunsaturated alkenyl group having 2 to 22 carbon atoms, a linear mono-hydroxyalkyl group with May be 2 to 10 carbon atoms, preferably a mono-hydroxyethyl or mono-hydroxypropyl group, as well as a linear or branched di-hydroxyalkyl group having 3 to 10 carbon atoms.
- the phosphoric esters according to the formula (II) are neutralized with a degree of neutralization of 0
- the mixtures according to the invention may contain one or more phosphoric acid esters of the formula (II) in which R 5 has the meaning of R 4 , and w is 0. These compounds are mono-phosphoric acid esters. These are preferably present in the mixtures according to the invention in an amount of ⁇ 3.0% by weight, more preferably ⁇ 1.0% by weight and particularly preferably ⁇ 0.1% by weight, based on the total weight of the phosphoric acid esters of the formula ( I) and (II). In the mono
- Phosphoric acid esters of the formula (II) R 4 and R 5 may be the same or different.
- the mixtures according to the invention contain one or more phosphoric acid esters of the formula (II) in which R 5 has the meaning of Ri and w is a number from 51 to 200, preferably from 55 to 150 and particularly preferably from 60 to 100, stands.
- These compounds are di-phosphoric acid esters. These are preferably present in the mixtures according to the invention in an amount of from 5.0 to 18.0% by weight, more preferably from 10.0 to 17.0% by weight and particularly preferably from 11.0 to 15.0% by weight. -%, Based on the total weight of the phosphoric acid esters according to formula (I) and (II) before.
- the radicals R 1 and R 5 may be identical or different.
- the preparation of mixtures of the phosphoric acid esters of the formulas (I) and (II) is preferably carried out by reacting phosphoric acid or a phosphoric acid derivative selected from orthophosphoric acid, Tetraphosphordecaoxid and polyphosphoric acid and particularly preferably by reaction of orthophosphoric acid, with fatty alcohol alkoxylates at temperatures between 150 and 250 0 C, preferably between 180 and 240 0 C and particularly preferably between 200 and 230 0 C.
- mixtures of the phosphoric acid esters of the formulas (I) and (II) are obtained, which are chlorine-free.
- these phosphoric acid esters of the formulas (I) and (II) contain no Chlorverungraphye ⁇ .
- phosphoric acid (85% strength) and fatty alcohol ethoxylate are used in a certain molar ratio.
- all starting materials are initially charged in a stirred apparatus with a heating mushroom, a descaling unit with a condenser and a vacuum connection.
- the mixture is heated to 100 0 C, evacuated three times to 100 mbar and then re-aerated with nitrogen.
- the mixture is heated under nitrogen inlet to 230 ° C and esterified (water discharge).
- the reaction times are from 24 to 42 hours (calculated from 230 ° C. esterification temperature), in particular 40 hours.
- the residual acid number is then included
- Esters from 11.4 g of phosphoric acid and 935.1 g Ceteareth-80 (C 6 / i ⁇ fatty alcohol + 80 moles ethylene oxide) in a molar ratio 1: 3, residual acid number: 0.8 mg KOH / g (96% conversion), 31 P-NMR: diester / Triester 15/85 mol%. It is a white wax with a melting point of about 40 0 C.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Physical Education & Sports Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Detergent Compositions (AREA)
- Polyethers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007036187A DE102007036187A1 (de) | 2007-08-02 | 2007-08-02 | Alkoxylierte Phosphorsäuretriester mit hohem Alkoxylierungsgrad |
| PCT/EP2008/006221 WO2009015859A2 (de) | 2007-08-02 | 2008-07-29 | Alkoxylierte phosphorsäuretriester mit hohem alkoxylierungsgrad |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP2185629A2 true EP2185629A2 (de) | 2010-05-19 |
Family
ID=39399886
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP08785169A Withdrawn EP2185629A2 (de) | 2007-08-02 | 2008-07-29 | Alkoxylierte phosphorsäuretriester mit hohem alkoxylierungsgrad |
Country Status (6)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102007036186A1 (de) * | 2007-08-02 | 2008-06-19 | Clariant International Limited | Phosphorsäureester enthaltend über Polyol-Einheiten verbrückte Phosporatome |
| EP2176349A2 (de) * | 2007-08-02 | 2010-04-21 | Clariant Finance (BVI) Limited | Phosphorsäureester enthaltend über diol-einheiten verbrückte phosphoratome |
| DE102007036188A1 (de) * | 2007-08-02 | 2008-06-19 | Clariant International Limited | Verfahren zur Herstellung alkoxylierter Phosphorsäuretriester |
| DE102008006857A1 (de) * | 2008-01-31 | 2009-01-29 | Clariant International Ltd. | Zusammensetzungen enthaltend Phosphorsäureester und hydrophob modifizierte vernetzte, anionische Polymere |
| WO2012019688A2 (de) | 2010-07-27 | 2012-02-16 | Clariant International Ltd | Zusammensetzungen enthaltend wasserstoffperoxid oder wasserstoffperoxid freisetzende substanzen |
| DE102010054918A1 (de) | 2010-12-17 | 2011-06-30 | Clariant International Ltd. | Zusammensetzungen enthaltend Wasserstoffperoxid oder Wasserstoffperoxid freisetzende Substanzen |
| DE102013204605A1 (de) * | 2013-03-15 | 2014-09-18 | Evonik Industries Ag | Phosphorsäureester, ihre Herstellung und Verwendung |
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| US2895787A (en) * | 1954-12-30 | 1959-07-21 | American Viscose Corp | Process of producing all skin rayon |
| NL248754A (enrdf_load_stackoverflow) * | 1959-02-24 | |||
| US4056480A (en) * | 1975-06-10 | 1977-11-01 | Monsanto Company | Hydraulic fluids |
| US4180532A (en) * | 1978-06-05 | 1979-12-25 | Gaf Corporation | Phosphoric acid esters of poly(2-10)ethyleneoxy n butane 1,4-diols |
| US4220611A (en) * | 1978-06-29 | 1980-09-02 | Sandoz, Inc. | Polyoxyalkylene bridged phosphate esters |
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| US7592300B2 (en) * | 2003-11-24 | 2009-09-22 | The Dial Corporation | Antimicrobial compositions containing an aromatic carboxylic acid and a hydric solvent |
| JP2005255875A (ja) * | 2004-03-12 | 2005-09-22 | Asahi Kasei Corp | 架橋構造体 |
| US7935732B2 (en) * | 2004-04-08 | 2011-05-03 | Isp Investments Inc. | Antimicrobial compositions |
| DE102004046356A1 (de) * | 2004-09-24 | 2006-03-30 | Clariant Gmbh | Verfahren zur Herstellung von Alk(en)ylphosphorsäureestersalzen |
| DE102004047092A1 (de) * | 2004-09-29 | 2006-03-30 | Clariant Gmbh | Agrochemische Zusammensetzung enthaltend Phosphorsäureester |
| FR2892936A1 (fr) * | 2005-11-10 | 2007-05-11 | Galderma Res & Dev | Composition pharmaceutique ou cosmetique, et procede de solubilisation mixte pour preparer la composition. |
| EP2176349A2 (de) * | 2007-08-02 | 2010-04-21 | Clariant Finance (BVI) Limited | Phosphorsäureester enthaltend über diol-einheiten verbrückte phosphoratome |
| DE102007036188A1 (de) * | 2007-08-02 | 2008-06-19 | Clariant International Limited | Verfahren zur Herstellung alkoxylierter Phosphorsäuretriester |
| DE102007036186A1 (de) * | 2007-08-02 | 2008-06-19 | Clariant International Limited | Phosphorsäureester enthaltend über Polyol-Einheiten verbrückte Phosporatome |
| JP2010535162A (ja) * | 2007-08-02 | 2010-11-18 | クラリアント・ファイナンス・（ビーブイアイ）・リミテッド | アルコキシル化されたリン酸トリエステルを含む水性組成物 |
| DE102008006857A1 (de) * | 2008-01-31 | 2009-01-29 | Clariant International Ltd. | Zusammensetzungen enthaltend Phosphorsäureester und hydrophob modifizierte vernetzte, anionische Polymere |
-
2007
- 2007-08-02 DE DE102007036187A patent/DE102007036187A1/de not_active Withdrawn
-
2008
- 2008-07-29 WO PCT/EP2008/006221 patent/WO2009015859A2/de active Application Filing
- 2008-07-29 JP JP2010518555A patent/JP2010535255A/ja active Pending
- 2008-07-29 CN CN200880101583A patent/CN101790554A/zh active Pending
- 2008-07-29 EP EP08785169A patent/EP2185629A2/de not_active Withdrawn
- 2008-07-29 US US12/671,802 patent/US20110230449A1/en not_active Abandoned
Non-Patent Citations (1)
| Title |
|---|
| See references of WO2009015859A2 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2010535255A (ja) | 2010-11-18 |
| US20110230449A1 (en) | 2011-09-22 |
| WO2009015859A2 (de) | 2009-02-05 |
| WO2009015859A3 (de) | 2009-09-03 |
| CN101790554A (zh) | 2010-07-28 |
| DE102007036187A1 (de) | 2008-06-19 |
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