WO2011054537A1 - Fumarate de sodium-malonate de sodium - Google Patents

Fumarate de sodium-malonate de sodium Download PDF

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Publication number
WO2011054537A1
WO2011054537A1 PCT/EP2010/006776 EP2010006776W WO2011054537A1 WO 2011054537 A1 WO2011054537 A1 WO 2011054537A1 EP 2010006776 W EP2010006776 W EP 2010006776W WO 2011054537 A1 WO2011054537 A1 WO 2011054537A1
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WO
WIPO (PCT)
Prior art keywords
halogen
stabilizer composition
polymers according
containing polymers
additionally
Prior art date
Application number
PCT/EP2010/006776
Other languages
German (de)
English (en)
Inventor
Cagan Heris
Michael Schiller
Mehmet Basalp
Original Assignee
Akdeniz Kimya Sanayi Ve Ticaret A.S.
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.)
Filing date
Publication date
Application filed by Akdeniz Kimya Sanayi Ve Ticaret A.S. filed Critical Akdeniz Kimya Sanayi Ve Ticaret A.S.
Publication of WO2011054537A1 publication Critical patent/WO2011054537A1/fr

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Classifications

    • 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
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C08K5/098—Metal salts of carboxylic acids
    • 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
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/005—Stabilisers against oxidation, heat, light, ozone
    • 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
    • C08K5/11—Esters; Ether-esters of acyclic polycarboxylic acids

Definitions

  • the invention relates to a composition for stabilizing halogen-containing polymers, in particular polyvinyl chloride (PVC) and halogenated resins. in hard-hard and soft applications involving said satellizer composition.
  • PVC polyvinyl chloride
  • Halogen-containing polymers or plastics or molded articles produced therefrom tend to undergo substantial changes during their production process and due to the effect of environmental influences. For example, these types of plastics may decompose or discolor under the influence of heat and / or light. To stabilize halogen-containing polymers, therefore, a very wide variety of substances or mixtures have already been used.
  • the calcium salt causes a fundamental stabilization of the halogen-containing polymer by the binding of the liberated hydrochloric acid as calcium chloride.
  • the calcium salt is sometimes also mixed with a magnesium salt on o.g. Base combined or replaced by a magnesium salt.
  • the calcium or magnesium salt may be used in combination with zinc salts based on o.o. organic acids are used.
  • the zinc salts with the formula 1 depicted give the halogen-containing polymer a good color, because they are the labile chlorine atoms on the
  • CONFIRMATION COPY halogen-containing polymer can substitute.
  • Zinc chloride is formed during this reaction. This chloride is known to the chemist as Lewis acids. It is capable of binding more than two chloride ions as shown in Formula 2. As a result, the chloride catalyzes the decomposition of the halogen-containing polymer and reduces the stability.
  • EP 0492803 describes the use of disodium adipate (DNA) as a costabilizer for (essentially) tin stabilizers.
  • the potassium adipate (Examples 14 and 15) has less stabilizing properties than DNA, which is recognized by the time it takes to blacken.
  • the main disadvantage of THEN is the deterioration of the initial color.
  • EP 2083044 describes the use of DNA in combination with a salt of perchloric acid or of H (CF 3 S0 3 ). Again, the beneficial effect of DNA in combination with sodium perchlorate in terms of color and / or stability.
  • zinc stearate and Natriumperchlorate (Example 3) presence suffers color stability during prolonged storage in the oven compared to zinc-free example of the second
  • the present invention is therefore based on the object to provide new stabilizer compositions which are particularly suitable for halogen-containing polymers, without having the above-mentioned disadvantages of the known stabilizers.
  • This object is achieved according to the invention by the provision of a stabilizer composition based on the sodium salts of fumaric acid and of malonic acid for halogen-containing polymers.
  • the stabilizer compositions according to the invention halogen-containing polymers and the parts and products made therefrom a very good initial color, a give excellent color retention and increased stability to the effects of sunlight and artificial light.
  • the initial color and the color retention of the halogen-containing material can be significantly improved compared to other organic and inorganic costabilizers when used in applications that are used outdoors, for example in window profiles.
  • moldings of halogen-containing polymers can be prepared without problems which enable optimum performance in use and which with the commodities for PVC stabilization on the basis of heavy metal-containing and -free
  • Stabilizer compositions are comparable. This stabilizing effect also occurs when the halogen-containing polymer contains further stabilizers, costabilizers or auxiliaries.
  • Stabilizer composition are present, with Zn compounds could be an exception.
  • Compounds of heavy metals such as tin, lead and / or cadmium are not desirable.
  • the present invention does not contain a compound of the general formula
  • X, Y or Z are either hydrogen or optionally substituted with alkyl radicals amino groups.
  • Such compounds are described in WO 2006/110106 Al.
  • the present invention also relates to the use of the invention
  • Stabilizer composition for the stabilization of halogen-containing polymers, as well as moldings of these halogen-containing polymers, which is a
  • Stabilizer composition according to the invention included.
  • the sodium fumarate and / or sodium malonate based stabilizer composition of the present invention may be used for halogen-containing polymers.
  • halogen-containing polymers may be thermoplastic halogen-containing polymers, for example, but not limited to, polyvinyl chloride (PVC),
  • Polyvinylidene chloride chlorinated or chlorosulfonated Polyethylene, chlorinated polypropylene or chlorinated ethylene / vinyl acetate copolymer or similar compounds.
  • Particularly advantageous are polymers of the PVC type, ie vinyl chloride homopolymers and copolymers of vinyl chloride with other monomers.
  • the stabilizer compositions for halogen-containing polymers according to the present invention contain at least one sodium salt of fumaric acid or a half ester of fumaric acid and / or a sodium salt of malonic acid or a half ester of malonic acid.
  • the stabilizer composition according to the present invention may be added in total in an amount of about 0.01 to about 10.0 parts per 100 parts of resin (phr).
  • the stabilizer composition is added in an amount of about 0.05 to about 5.0 phr, for example, in an amount of about 0.1 to about 2.0.
  • An amount of 0.1 to 1.9 is preferred, with the amounts of 0.1 to 1.6, 0.1 to 1.8, 0.1 to 1.7, 0.1 to 1.6, 0.1 to 1.5 being particularly preferred.
  • the lower limit can be 0.2, 0.3, 0. 4, 0.5, 0.6, 0.7, 0.8. 0.9 or 1.0.
  • the stabilizer composition used according to the invention can be added individually to the polymer or to the polymer mixture. However, it is also possible to add the combination according to the invention together with other (co) stabilizers or the auxiliaries listed below to the polymer or a polymer mixture. For example, metering in the extruder, eg in the vacuum zone, is also encompassed by the present invention.
  • the stabilizer composition according to the invention may further comprise one or more additional additives, such as, for example, primary stabilizers, co-stabilizers, zeolites, antioxidants, fillers, plasticizers,
  • Stabilizers can be combined.
  • Co-stabilizers are compounds which provide a further stabilizing contribution to halogen-containing polymers when used in the stabilizer composition according to the present invention. Possible co-
  • Stabilizers may be selected from the group consisting of 1,3-diketone compounds, dihydropyridines, polyols,
  • Isocyanurates metal salts, natural or synthetic minerals such as hydrotalcites, hydrocalumites, zeolites, amino acid derivatives, organic esters of phosphorous acid, epoxy compounds, perchlorates and salts of superacids.
  • 1,3-diketone compounds include, but are not limited to, dibenzoylmethane,
  • Co-stabilizers from the group of polyols include, but are not limited to, glycerol, pentaerythritol, di- and tri-pentaerythritol, trismethylolpropane (TMP), di-TMP, sorbitol, mannitol, alititol, saccharides, disaccharides
  • Galactopyranosyl-D-glucitol 4-O-alpha-D-glucopyranosyl-D-glucitol, 6-O-alpha-D-galactopyranosyl-D-glucose, 3-O-alpha-D-galactopyranosyl-D-myo-inositol, 4-O- ⁇ -D-galactopyranosyl-D-fructose, 4-O- ⁇ -D-galactopyranosyl- ⁇ -D-glucopyranose, 6-O-alpha-D-glucopyranosyl-D-fructose, 4-O- ⁇ - D-galactopyranosyl-alpha-D-glucopyranose, 2-0- (6-deoxy-alpha-L-mannopyranosyl) -D-glucose, 4-0-alpha-D-glucopyranosyl-D-fructose, 2-0-beta D-glu
  • antioxidants include, but are not limited to, alkylphenols, hydroxyphenylpropionates, hydroxybenzyl compounds, alkylidene bisphenols, thiobisphenols, and aminophenols, especially, for example, 2,6-di-tert. -butyl-4-methylphenol, 2, 6-Di-benzyl-4-methyl-phenol, stearyl-3- (3 '-5 1 -di-tert. butyl-' -hydroxy-phenyl) propionate, 4 '4'-thiobis (3-methyl-6-tert-butylphenol), 4-nonylphenol, 2,2'-methylenebis (4-methyl-6-tert-butylphenol), 2,5-diol tert.
  • co-stabilizers from the group of metal salts include, but are not limited to, hydroxides, oxides, carbonates, basic carbonates, and carboxylic acid salts of lithium, sodium, potassium, magnesium, calcium, aluminum, titanium, and the like.
  • the metal salts may be salts of carboxylic acids.
  • Carboxylic acids are carboxylic acids which have 2-22, in particular 7-22 carbon atoms and can be aliphatic or aromatic, saturated or unsaturated, branched or unbranched. Examples of suitable
  • Carboxylic acid anions include anions of monovalent carboxylic acids such as acetic acid, propionic acid, butyric acid, valeric acid, hexanoic acid, enanthic acid, Octanoic acid, neodecanoic acid, 2-ethylhexanoic acid,
  • Sorbic acid anions of divalent carboxylic acids or their onoesters such as oxalic acid, maleic acid, adipic acid, tartaric acid, cinnamic acid, mandelic acid, malic acid, glycolic acid, salicylic acid, Polyglykoldicarbon Acid with a
  • Examples of natural and synthetic minerals include, but are not limited to, A3, A4, A5 zeolites, mordenite, erionite, faujasite X or Y zeolites, and ZSM-5 zeolites, hydrotalcites (from Alcamizer 1 and 4-type) and / or mixtures thereof.
  • Examples of co-stabilizers from the group of amino acid derivatives include, but are not limited to, glycine, alanine, lysine, tryptophan,
  • the alcohol components of these esters may include monohydric alcohols such as methyl alcohol, ethyl alcohol, propyl alcohol, i-propyl alcohol, butyl alcohol, ⁇ -ethylhexanol, octyl alcohol, i-octyl alcohol, lauryl alcohol, stearyl alcohol, and the like, as well as polyols such as ethylene glycol, Propylene glycol, 1, 3-butanediol, 1, 4-butanediol, glycerol, diglycerol, trismethylolpropane, pentaerythritol,
  • co-stabilizers from the group of phosphorous acid esters include, but are not limited to, triaryl phosphites, such as
  • Triphenyl phosphite tris (p-nonylphenyl) phosphite
  • Alkylaryl phosphites such as
  • Monoalkyl diphenyl phosphites e.g. Diphenylisooctyl phosphite, diphenylisodecyl phosphite; and dialkyl monophenyl phosphites such as phenyl diisooctyl phosphite, phenyl diisodecyl phosphite; and trialkyl phosphites such as triisooctyl phosphite, tristearyl phosphite and the like.
  • co-stabilizers from the group of epoxy compounds include, but are not limited to, various animal or vegetable oils, such as epoxysoic, epoxy, or epoxidized Carboxylic acid esters such as epoxidized epoxy methyl oleate, epoxy butyl oleate, epoxidized alicyclic compounds, glycidyl ethers such as bisphenol A diglycidyl ether, bisphenol F diglycidyl ether; Glycidic esters, such as glycidyl acrylate, glycidyl methacrylate, their polymers, copolymers; and epoxidized polymers such as epoxidized polybutadiene, epoxidized ABS, and the like.
  • various animal or vegetable oils such as epoxysoic, epoxy, or epoxidized Carboxylic acid esters such as epoxidized epoxy methyl oleate, epoxy butyl oleate, epoxidized alicyclic compounds, glycid
  • Exemplary isocyanurates include, but are not limited to,
  • Exemplary dihydropyridines include, but are not limited to,
  • Exemplary perchlorates include, but are not limited to, NaC104, Ca (C104) 2, Mg (C104) 2, or A1 (C104) 3. Further exemplary compounds of this group are Alcamizer 5 and Alcamizer 5-2 from Kyowa.
  • chalk or coated chalk may also be named as fillers, the fillers being not restricted thereto.
  • Stabilizer composition of the invention can be added is titanium dioxide. Titanium dioxide occurs essentially in nature in three modifications: anatase, brookite, and rutile.
  • a stabilizer composition of the invention may further include lubricants such as montan wax, fatty acid esters, purified or hydrogenated natural or synthetic triglycerides or partial esters, polyethylene waxes, amide waxes, chloroparaffins, glycerol esters or
  • lubricants Contain alkaline earth soap.
  • Useful lubricants are moreover also described in "Plastics Additives Handbook", H. Zweifel / RD Maier / M. Schiller, Carl Hanser Verlag, 6th edition, 2009, pp. 539-579.
  • Further suitable lubricants are, for example, fatty ketones as described in DE 4204887 and
  • Silicone-based lubricant as it is called, for example, EP-DA 0 259 783, or combinations thereof, as described in the
  • EP-DA 0 259 783 are called.
  • the documents cited are hereby expressly incorporated by reference.
  • halogen-containing polymers with the stabilizer composition according to the invention In order to process halogen-containing polymers with the stabilizer composition according to the invention, the processes known in the prior art can be used. Examples of such methods include, but are not limited to, calendering, extruding, injection molding, blow molding, and the like.
  • the stabilized halogen-containing polymers prepared according to the invention can be prepared for different applications.
  • window profiles, pipes, floor coverings, roofing membranes, cables and films can be produced.
  • the polymers can be used in materials, for example, for pleasure craft, rotor blades for wind turbines and wagon construction.
  • the present invention accordingly provides a remarkable and novel contribution to the development of the prior art, in particular for the processing and stabilization of PVC and other halogen-containing materials thermoplastic polymers.
  • the selection of the examples is based on the examples in EP2083044A1.
  • the selected test substances (both according to the invention and not according to the invention) were prepared in the laboratory and tested in PVC.
  • a dry blend of the following composition was brought to a temperature of 120 ° C. in the course of 5 minutes in a heating refrigerator without additional heating and then cooled to 40 ° C. within a further 5 minutes. Subsequently, the dry blend was stored for 24 h at room temperature.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne une composition stabilisatrice pour des polymères contenant des halogènes, qui contient au moins un sel de sodium d'un acide dicarboxylique du groupe de l'acide malonique et/ou de l'acide fumarique et/ou de leurs monoesters.
PCT/EP2010/006776 2009-11-06 2010-11-08 Fumarate de sodium-malonate de sodium WO2011054537A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102009052207.7 2009-11-06
DE102009052207 2009-11-06

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WO2011054537A1 true WO2011054537A1 (fr) 2011-05-12

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102013005426A1 (de) 2013-03-27 2014-10-02 Baerlocher Gmbh Stabilisatorzusammensetzungen enthaltend Salze von Dicarbonsäuren und Polyole

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE875865C (de) * 1940-03-01 1953-05-07 Hoechst Ag Verfahren zum Stabilisieren von Vinylchloridpolymerisaten
DE2137373A1 (de) * 1970-07-27 1972-02-10 Solvay Stabilisierung von mit Hilfe von chlorhaltigen Weichmachern weichgemachtem Polyvinylchlorid
GB1291144A (en) * 1970-05-18 1972-09-27 Pfizer Non-toxic stabilizer compositions for chlorine-containing polymers
US3965064A (en) * 1972-02-28 1976-06-22 Unibra S.A. Process for the crystallization of polycarbonates and products obtained
EP0259783A2 (fr) 1986-09-10 1988-03-16 NEYNABER CHEMIE GmbH Lubrifiant pour des matières thermoplastiques
DE4002988A1 (de) 1990-02-01 1991-08-14 Baerlocher Chem Basische calcium-aluminium-hydroxid-dicarboxylate, verfahren zu deren herstellung und deren verwendung
EP0492803A1 (fr) 1990-12-27 1992-07-01 Elf Atochem North America, Inc. Composition stabilisée de polymère halogéné
DE4106404C1 (fr) 1991-02-28 1992-07-09 Baerlocher Gmbh, 8000 Muenchen, De
DE4204887A1 (de) 1992-02-19 1993-08-26 Neynaber Chemie Gmbh Verwendung von fettketonen als gleitmittel fuer formmassen auf basis von polyvinylchlorid bzw. vinylchlorid-copolymeren
WO2006110106A1 (fr) 2005-04-15 2006-10-19 Sun Ace Kakok (Pte.) Ltd. Composition de stabilisation pour des polymères contenant du chlore
EP2083044A1 (fr) 2008-01-23 2009-07-29 Reagens S.p.A. Composition pour stabiliser des polymères contenant de l'halogène

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE875865C (de) * 1940-03-01 1953-05-07 Hoechst Ag Verfahren zum Stabilisieren von Vinylchloridpolymerisaten
GB1291144A (en) * 1970-05-18 1972-09-27 Pfizer Non-toxic stabilizer compositions for chlorine-containing polymers
DE2137373A1 (de) * 1970-07-27 1972-02-10 Solvay Stabilisierung von mit Hilfe von chlorhaltigen Weichmachern weichgemachtem Polyvinylchlorid
US3965064A (en) * 1972-02-28 1976-06-22 Unibra S.A. Process for the crystallization of polycarbonates and products obtained
EP0259783A2 (fr) 1986-09-10 1988-03-16 NEYNABER CHEMIE GmbH Lubrifiant pour des matières thermoplastiques
DE4002988A1 (de) 1990-02-01 1991-08-14 Baerlocher Chem Basische calcium-aluminium-hydroxid-dicarboxylate, verfahren zu deren herstellung und deren verwendung
EP0492803A1 (fr) 1990-12-27 1992-07-01 Elf Atochem North America, Inc. Composition stabilisée de polymère halogéné
DE4106404C1 (fr) 1991-02-28 1992-07-09 Baerlocher Gmbh, 8000 Muenchen, De
DE4204887A1 (de) 1992-02-19 1993-08-26 Neynaber Chemie Gmbh Verwendung von fettketonen als gleitmittel fuer formmassen auf basis von polyvinylchlorid bzw. vinylchlorid-copolymeren
WO2006110106A1 (fr) 2005-04-15 2006-10-19 Sun Ace Kakok (Pte.) Ltd. Composition de stabilisation pour des polymères contenant du chlore
EP2083044A1 (fr) 2008-01-23 2009-07-29 Reagens S.p.A. Composition pour stabiliser des polymères contenant de l'halogène

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
H. ZWEIFEL; R. D. MAIER; M. SCHILLER: "Plastics Additives Handbook", vol. 6, 2009, CARL HANSER VERLAG, pages: 539 - 579

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102013005426A1 (de) 2013-03-27 2014-10-02 Baerlocher Gmbh Stabilisatorzusammensetzungen enthaltend Salze von Dicarbonsäuren und Polyole

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