EP1549608A1 - Ester und partialester aus mehrwertigen alkoholen - Google Patents
Ester und partialester aus mehrwertigen alkoholenInfo
- Publication number
- EP1549608A1 EP1549608A1 EP03748071A EP03748071A EP1549608A1 EP 1549608 A1 EP1549608 A1 EP 1549608A1 EP 03748071 A EP03748071 A EP 03748071A EP 03748071 A EP03748071 A EP 03748071A EP 1549608 A1 EP1549608 A1 EP 1549608A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- esters
- partial esters
- partial
- acid
- component
- 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- Withdrawn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
- 150000002148 esters Chemical class 0.000 title claims abstract description 62
- 150000001298 alcohols Chemical class 0.000 title abstract description 4
- 239000000203 mixture Substances 0.000 claims abstract description 18
- 239000004033 plastic Substances 0.000 claims abstract description 14
- 229920003023 plastic Polymers 0.000 claims abstract description 14
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 239000002270 dispersing agent Substances 0.000 claims abstract description 3
- 239000000049 pigment Substances 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 21
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 20
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 16
- 229930195729 fatty acid Natural products 0.000 claims description 16
- 239000000194 fatty acid Substances 0.000 claims description 16
- 150000004665 fatty acids Chemical group 0.000 claims description 16
- 150000005846 sugar alcohols Polymers 0.000 claims description 10
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 9
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 claims description 6
- -1 polypropylene Polymers 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 239000001361 adipic acid Substances 0.000 claims description 4
- 235000011037 adipic acid Nutrition 0.000 claims description 4
- 125000001142 dicarboxylic acid group Chemical group 0.000 claims description 4
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 4
- 239000004800 polyvinyl chloride Substances 0.000 claims description 4
- 229920001169 thermoplastic Polymers 0.000 claims description 4
- 239000004416 thermosoftening plastic Substances 0.000 claims description 4
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 claims description 3
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000539 dimer Substances 0.000 claims description 3
- 229920000223 polyglycerol Polymers 0.000 claims description 3
- 239000000600 sorbitol Substances 0.000 claims description 3
- 239000006057 Non-nutritive feed additive Substances 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims description 2
- 239000004743 Polypropylene Substances 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- 229920001155 polypropylene Polymers 0.000 claims description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 abstract description 12
- 239000012170 montan wax Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000314 lubricant Substances 0.000 description 4
- 102200046998 rs62645894 Human genes 0.000 description 4
- 239000003760 tallow Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- MSIAVMAKMIQAKE-UHFFFAOYSA-N CCC(CO)(CO)CO.CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O Chemical compound CCC(CO)(CO)CO.CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O MSIAVMAKMIQAKE-UHFFFAOYSA-N 0.000 description 1
- 239000004605 External Lubricant Substances 0.000 description 1
- ACHULMYKNXGIQZ-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] octacosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)OCC(CO)(CO)CO ACHULMYKNXGIQZ-UHFFFAOYSA-N 0.000 description 1
- OCKWAZCWKSMKNC-UHFFFAOYSA-N [3-octadecanoyloxy-2,2-bis(octadecanoyloxymethyl)propyl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCCCCCCC)(COC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC OCKWAZCWKSMKNC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/30—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with trihydroxylic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/33—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with hydroxy compounds having more than three hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
- C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K
Definitions
- the invention relates to esters and partial esters of polyhydric alcohols and carboxylic acids and their use.
- the fatty acids are chain-pure or mixed in their chain length distributions, products of chain lengths C ⁇ to C-i ⁇ , in exceptional cases also C22 saturated and C22 unsaturated are available.
- montan wax acid is a mixture of long-chain carboxylic acids with 24 to 34 carbon atoms, which are obtained during the refining of montan wax.
- Non-polar lubricants Phase boundary melt to tool and then also act as a release agent.
- Non-polar lubricants have an external effect in polar plastics
- polar lubricants have an external effect in non-polar plastics and vice versa.
- Montan wax derivatives generally show a noticeable inherent color that generally prohibits their use in transparent applications.
- Fatty acid esters have only a small intrinsic color, but are often too polar and too flexible or volatile at high temperatures due to their shorter chain length.
- the invention therefore relates to esters and partial esters of the type mentioned at the outset, characterized in that they contain at least one
- component B Contain carboxylic acid residue and / or a residue of a carboxylic acid mixture with 24 to 34 C atoms (component B) and at least one carboxylic acid residue and / or a residue of a carboxylic acid mixture with 8 to 22 C atoms (component C).
- the polyhydric alcohol preferably has 3 to 12 hydroxyl groups.
- the polyhydric alcohol is preferably trimethylolpropane, trimethylolethane, pentaerythritol, glycerol, diglycerol, polyglycerol, sorbitol, dipentaerythritol, ditrimethylolpropane and / or their ethoxylated derivatives.
- the polyhydric alcohol is particularly preferably trimethylolpropane, glycerol and / or pentaerythritol.
- the rest of the carboxylic acid mixture (component C) preferably contains 8 to 18 carbon atoms.
- esters and partial esters preferably also contain at least one dicarboxylic acid residue and / or the rest of a dicarboxylic acid mixture (component D).
- the dicarboxylic acid residue and / or the rest preferably derive from
- Dicarboxylic acid mixtures from compounds such as adipic acid, dodecanedioic acid or dimer fatty acid Dicarboxylic acid mixtures from compounds such as adipic acid, dodecanedioic acid or dimer fatty acid.
- esters and partial esters according to the present invention preferably have an acid number of 5 to 25.
- esters and partial esters according to the present invention preferably have a hydroxyl number of 5 to 400 (defined according to DGF method M-IV-6 (57)).
- esters and partial esters according to the present invention particularly preferably have a hydroxyl number of 5 to 150.
- the invention also relates to the use of esters and partial esters according to the present invention as processing aids or in the processing of plastics.
- the plastics are preferably thermoplastics.
- the thermoplastics are particularly preferably polyvinyl chloride, polyester, polycarbonate, polyamide or polypropylene.
- esters and partial esters according to the invention can be used as dispersants for pigments and as lubricants in the processing of plastics.
- esters As is generally known, the reaction of polyhydric alcohols with carboxylic acids to form esters always gives mixtures of esters of different degrees of esterification. If alcohols with three or more alcohol functions are used, such as, for example, trimethylolpropane, pentaerythritol, glycerol, sorbitol, ditrimethylolpropane, dipentaerythritol, diglycerol or polyglycerol, it is possible first to use a two-stage process and an acidic catalyst to isolate the partial esters of high molecular acid (component b ) and then implement all or part of the free hydroxyl groups with the more reactive low molecular acid (component C). This creates a polyol ester or partial ester in which carboxylic acids with 8 to 22 and 24 to 34 C atoms are incorporated in a targeted manner.
- component b an acidic catalyst
- the reaction can also be carried out in a single process step.
- Montan wax acid (1.1 mol) and tallow fatty acid (1.2 mol) were melted at 100 ° C. and glycerol (1 mol) and Fascat 2001 (0.1% by weight) were added at this temperature, then heated to 190 ° C. , The mixture was rendered inert with N 2 , stirred while distilling off the water of reaction until the acid number had dropped below 15, then cooled to 120 ° C. and filtered.
- Montan wax acid (1.5 mol) and tallow fatty acid (2 mol) were melted at 100 ° C. and pentaerythritol (1 mol) and Fascat 2001 (0.1% by weight) were added at this temperature, then heated to 190 ° C.
- the mixture was rendered inert with N 2 , stirred while distilling off the water of reaction until the acid number had dropped below 20, then cooled to 120 ° C. and filtered.
- Test product (A ester type) optionally 0.3 or 0.5% by weight
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10245623 | 2002-09-30 | ||
DE10245623A DE10245623A1 (de) | 2002-09-30 | 2002-09-30 | Ester und Partialester aus mehrwertigen Alkoholen |
PCT/EP2003/010502 WO2004031121A1 (de) | 2002-09-30 | 2003-09-22 | Ester und partialester aus mehrwertigen alkoholen |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1549608A1 true EP1549608A1 (de) | 2005-07-06 |
Family
ID=31984290
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP03748071A Withdrawn EP1549608A1 (de) | 2002-09-30 | 2003-09-22 | Ester und partialester aus mehrwertigen alkoholen |
Country Status (5)
Country | Link |
---|---|
US (1) | US20060094805A1 (de) |
EP (1) | EP1549608A1 (de) |
JP (1) | JP2006501337A (de) |
DE (1) | DE10245623A1 (de) |
WO (1) | WO2004031121A1 (de) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007039602A2 (en) * | 2005-10-04 | 2007-04-12 | Akzo Nobel Coatings International B.V. | Pigment preparation |
US7779856B2 (en) | 2005-10-05 | 2010-08-24 | Societe Bic | Fuel cartridge of a fuel cell with fuel stored outside fuel liner |
EP1881025B1 (de) * | 2006-07-20 | 2010-02-17 | Cognis Oleochemicals GmbH | Verwendung von Polyethylenglykolestern von Fettsäuren als Gleitmittel für thermoplastische Kunststoffe |
RU2428208C2 (ru) * | 2007-02-09 | 2011-09-10 | КейСиАй Лайсензинг Инк. | Система и способ управления пониженным давлением на участке ткани |
DE102008008251A1 (de) * | 2008-02-08 | 2009-08-20 | Cognis Oleochemicals Gmbh | Vernetzte Glycerin- oder Oligoglycerinester und deren Verwendung als Additiv in Bohrspülungen |
US10752750B2 (en) * | 2014-11-13 | 2020-08-25 | Sabic Global Technologies B.V. | Polyester composition and article prepared therefrom |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2441555A (en) * | 1943-10-12 | 1948-05-18 | Heyden Chemical Corp | Mixed esters of polyhydric alcohols |
NL171815B (nl) * | 1977-12-18 | 1982-12-16 | Nautamix Bv | Werkwijze ter bereiding van droge, poedervormige mengsels uit polyvinylchloride, glijmiddelen en stabilisatoren en werkwijze ter vervaardiging van voorwerpen daaruit. |
DE3405875A1 (de) * | 1984-02-18 | 1985-08-22 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von zelligen oder kompakten polyurethan-polyharnstoff-formkoerpern mit verbesserten entformungseigenschaften sowie innere formtrennmittel fuer das polyisocyanat-polyadditionsverfahren |
DD246559A1 (de) * | 1986-03-10 | 1987-06-10 | Petrolchemisches Kombinat | Verfahren zur herstellung von partialsynthetischen weichwachsen auf montanwachsbasis - 2 - |
DE4020483A1 (de) * | 1990-06-27 | 1992-01-02 | Hoechst Ag | Mischester und seine verwendung als gleitmittel in kunststoff-formmassen |
CA2096152A1 (en) * | 1992-05-20 | 1993-11-21 | Lawrence W. Masten | Esterified propoxylated glycerin fat substitute compositions resistant to gastrointestinal side effects |
JP3442101B2 (ja) * | 1992-07-27 | 2003-09-02 | 日清オイリオ株式会社 | ラノリン様合成油剤及びこれを配合してなる化粧品、外用剤 |
JPH0797495A (ja) * | 1993-09-28 | 1995-04-11 | Nisshin Fine Chem Kk | ハロゲン含有樹脂組成物 |
DE4413849A1 (de) * | 1994-04-21 | 1995-10-26 | Hoechst Ag | Feinverteilungsverfahren zur Herstellung von organischen Pigmenten |
DE19546073A1 (de) * | 1995-12-11 | 1997-06-12 | Hoechst Ag | Stabile wäßrige Wachsdispersionen |
DE19641604C1 (de) * | 1996-10-09 | 1998-03-12 | Goldschmidt Ag Th | Polyglycerinpartialester von Fettsäuren und mehrfunktionellen Carbonsäuren, deren Herstellung und Verwendung |
SK285128B6 (sk) * | 1999-12-28 | 2006-07-07 | Zentiva, A. S. | Liečivý prípravok s riadeným uvoľňovaním obsahujúci tramadol hydrochlorid a spôsob jeho prípravy |
-
2002
- 2002-09-30 DE DE10245623A patent/DE10245623A1/de not_active Withdrawn
-
2003
- 2003-09-22 JP JP2004540666A patent/JP2006501337A/ja not_active Withdrawn
- 2003-09-22 WO PCT/EP2003/010502 patent/WO2004031121A1/de not_active Application Discontinuation
- 2003-09-22 EP EP03748071A patent/EP1549608A1/de not_active Withdrawn
- 2003-09-22 US US10/529,827 patent/US20060094805A1/en not_active Abandoned
Non-Patent Citations (1)
Title |
---|
See references of WO2004031121A1 * |
Also Published As
Publication number | Publication date |
---|---|
US20060094805A1 (en) | 2006-05-04 |
WO2004031121A1 (de) | 2004-04-15 |
JP2006501337A (ja) | 2006-01-12 |
DE10245623A1 (de) | 2004-04-08 |
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Owner name: CLARIANT PRODUKTE (DEUTSCHLAND) GMBH |
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