WO2011054536A1 - Compositions stabilisatrices à une faible teneur en zinc pour profilés de fenêtres, - Google Patents

Compositions stabilisatrices à une faible teneur en zinc pour profilés de fenêtres, Download PDF

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Publication number
WO2011054536A1
WO2011054536A1 PCT/EP2010/006775 EP2010006775W WO2011054536A1 WO 2011054536 A1 WO2011054536 A1 WO 2011054536A1 EP 2010006775 W EP2010006775 W EP 2010006775W WO 2011054536 A1 WO2011054536 A1 WO 2011054536A1
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WIPO (PCT)
Prior art keywords
halogen
stabilizer composition
polymers according
containing polymers
stabilizer
Prior art date
Application number
PCT/EP2010/006775
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German (de)
English (en)
Inventor
Cagan Heris
Michael Schiller
Tarkan Uysal
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.)
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Application filed by Akdeniz Kimya Sanayi Ve Ticaret A.S. filed Critical Akdeniz Kimya Sanayi Ve Ticaret A.S.
Publication of WO2011054536A1 publication Critical patent/WO2011054536A1/fr

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    • 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
    • C08K5/0091—Complexes with metal-heteroatom-bonds
    • 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
    • C08K5/09—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
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring

Definitions

  • the invention relates to a low-zinc composition for the stabilization of halogen-containing polymers, in particular polyvinyl chloride (PVC) .
  • 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.
  • a halogen-containing polymer e.g. Polyvinyl chloride (PVC)
  • PVC Polyvinyl chloride
  • metal carboxylates as stabilizers in the resin.
  • melt-molding process causes blackening of the polymer, it is common practice to add a co-stabilizer.
  • a co-stabilizer There are a variety of combinations of inorganic and organic compounds known as stabilizers for halogen-containing polymers.
  • 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 occasionally combined with a magnesium salt to the above base """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 having the formula 1 depicted above give the halogen-containing polymer a good color because they can substitute the labile chlorine atoms on the halogen-containing polymer (PVC).
  • 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.
  • comparable zinc contents for stabilizer combinations for PVC profiles can be found at a comparable amount as shown in Tab. 1.
  • Zinc contents ⁇ 2.0% can be found only at a significantly higher input quantity, which has significant cost disadvantages for the user.
  • Such stabilizer combinations make it possible to produce plastic profiles with good thermal and light stability " in combination with a good initial color.”
  • the light and weathering stability is attributed, among other things, to the presence of zinc compounds by the person skilled in the art, but zinc as well as lead, tin and sulfur become an element considered unsustainable in the literature (C. Azar, J. Holmberg, K.
  • a PVC stabilizer composition has advantageous properties, particularly when using the composition for the plastic profiles, when the Zn content is limited within a very narrow range. Therefore, there is a need to provide stabilizer combinations that have the better properties than the usual stabilizer compositions.
  • Tab. 1 shows an overview of zinc contents of (window) profile stabilizer combinations in the Patent literature (patent number, example, amount of stabilizer combination used in phr, zinc content in%, application)
  • Patent no. Example use amount% Zn application
  • the present invention is therefore based on the object of providing new low-zinc stabilizer compositions at a use amount ⁇ 4.5 phr, which are particularly suitable for PVC profiles, without having the above-mentioned disadvantages of the known stabilizers.
  • This object is achieved by providing a stabilizer composition with Zinc contents of 0.5 to 1.5% at a use rate ⁇ 4.5 phr for PVC profiles.
  • 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 profiles.
  • the stabilizer compositions according to the invention moldings of halogen-containing polymers can easily be produced which enable optimum performance in use and which are comparable to PVC stabilization commodities based on stabilizer compositions for PVC profiles. This stabilizing effect also occurs when the PVC contains further stabilizers, co-stabilizers or adjuvants.
  • the present invention also relates to the use of the invention
  • Stabilizer composition for the stabilization of PVC profiles, as well as the PVC profiles, the one
  • the low-zinc stabilizer composition of the present invention can 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 are particularly advantageous.
  • Particularly advantageous are polymers of the PVC type, i. 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 zinc compound.
  • Stabilizer composition according to the present invention may be added in total in an amount of about 1 to 4.5 parts per 100 parts of resin (phr).
  • Stabilizer composition in an amount of about 2.0 to 4.3 phr added, for example in an amount of about 2.5 to about 3.8.
  • 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.
  • a dosage in the extruder for example in the Vacuum zone, 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,
  • 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 tripentaerythritol, trismethylolpropane (TMP), di-TMP, sorbitol, mannitol, malititol, saccharides, disaccharides (especially sucrose, 4-O ⁇ -D-galactopyranosyl-D-glucose, 4-O-alpha-D-glucopyranosyl-D-glucose, 6-O- (6-deoxy-alpha-L-mannopyranosyl) -D-glucose, alpha-D-glucopyranosyl alpha-D-glucopyranoside, 6-0-alpha-D-glucopyranosyl-D-glucose, 4-O-beta-D-glucopyranosyl-D-glucose, 2-O-beta-D-glu
  • 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-O-alpha-D-glucopyranosyl-D-fructose, 2-O-ß- D-glucopy
  • Glucopyranosyl-D-fructose 6-O-alpha-D-glucopyranosyl-alpha-D-fructofuranose, 6-O-alpha-D-glucopyranosyl-D-glucitol, 4-O-beta-D-galactopyranosyl-D-glucitol, 4-0-alpha-D- Glucopyranosyl-D-glucitol, 1-O-alpha-D-glucopyranosyl-D-mannitol), trisaccharides, polysaccharides, especially polyvinyl alcohols, starch, cellulose and theirs
  • antioxidants include, but are not limited to, alkylphenols, hydroxyphenylpropionates, hydroxybenzyl compounds, alkylidenebisphenols, thiobisphenols, and aminophenols, especially, for example, 2,6-di-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 used 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.
  • carboxylic anions include anions of mono and divalent 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 monoesters such as oxalic acid, malonic acid, maleic acid, fumaric acid, adipic acid, tartaric acid, cinnamic acid, mandelic acid, malic acid, glycolic acid, salicylic acid,
  • Polyglykoldicarbon Acid having a degree of polymerization of about 10 to about 12, phthalic acid, isophthalic acid, terephthalic acid or hydroxyphthalic acid, anions of trioder tetravalent carboxylic acids or
  • natural and synthetic minerals include, but are not limited to, A3, A4, A5 zeolites, mordenite zeolites, erionite, faujasite X. or Y-type and ZSM-5 zeolites, hydrotalcites (Alcamizer 1 and 4 type) and / or mixtures thereof.
  • 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
  • Monoalkyldiphenylphosphites eg diphenylisooctylphosphite, diphenylisodecylphosphite; 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 epoxysoar oil, epoxy rapeseed oil, epoxidized carboxylic acid esters, such as epoxidized epoxy methyl oleate, epoxybutyl oleate, epoxidized alicyclic compounds, glycidyl ethers, such as For example, 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 epoxysoar oil, epoxy rapeseed oil, epoxidized carboxylic acid esters, such as epoxidized epoxy methyl oleate, epoxybutyl oleate
  • Exemplary isocyanurates include, but are not limited to,
  • dihydropyridines include, but are not limited to,
  • Exemplary perchlorates include, but are not limited to, NaC104, Ca (C104) 2, g (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.
  • lubricants are, for example, fatty ketones as described in DE 4204887 and silicone-based lubricants, as mentioned for example in EP-A 0 259 783, or combinations thereof, as mentioned in EP-A 0 259 783.
  • the documents cited are hereby incorporated by reference, the disclosure of which relates to lubricants being considered part of the disclosure of the present text.
  • the stabilizer composition according to the invention has at least the following component:
  • Zinc, calcium and / or magnesium salts of at least one C7-C22 carboxylic acid which may be aliphatic or aromatic, saturated or unsaturated, branched or unbranched, such as. of technical stearic, lauric, C8-10 carboxylic and / or benzoic acid,
  • Zn-content of such a composition is between 0.5 to 1.5 wt.% With a starting amount of 1 to 4.5 phr.
  • the stabilizer composition preferably contains an isocyanurate compound.
  • the stabilizer composition according to the invention is preferably solid and preferably contains no solvent.
  • Stabilizer composition to process the methods known in the art can be used. Examples of such methods include, but are not limited to, extruding and the like.
  • 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 profiles and other halogen-containing thermoplastic polymers, preferably rigid PVC.
  • Paraffin wax (1 10 ° C) 0.20 0.20 0.20 0.20 oxidized PE wax 0.10 0.10 0.10 0.10 0.10
  • Zinc benzoate (21.3% Zn) 0.20 0.10

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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, présentant une teneur en zinc approximativement comprise entre environ 0,5 et environ 1,5% Zn (par rapport à la quantité totale de la composition stabilisatrice) pour une quantité utilisée de stabilisateur comprise entre environ1 et 4,5 pour 100 parties de résine.
PCT/EP2010/006775 2009-11-06 2010-11-08 Compositions stabilisatrices à une faible teneur en zinc pour profilés de fenêtres, WO2011054536A1 (fr)

Applications Claiming Priority (2)

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DE102009052206.9 2009-11-06
DE102009052206A DE102009052206A1 (de) 2009-11-06 2009-11-06 Stabilisatorzusammensetzung mit niedrigem Zinkgehalt für Fensterprofile

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102604295A (zh) * 2012-01-12 2012-07-25 河北大学 聚合物钙锌复合皂热稳定剂、其制备方法及其应用
US8633266B2 (en) 2010-05-11 2014-01-21 Akdeniz Kimya San. ve Tic. A.S. Tin-free stabilizer composition
CN104387616A (zh) * 2014-12-16 2015-03-04 天津中财型材有限责任公司 复合Ca/Zn稳定剂及其制备方法以及环保型材
CN105585798A (zh) * 2016-02-22 2016-05-18 江苏爱特恩东台新材料科技有限公司 废聚酯制备的pvc线缆专用环保热稳定剂及其制备方法
CN106478990A (zh) * 2016-09-26 2017-03-08 深圳市志海实业股份有限公司 一种新型熔融一步法制备羟基脂肪酸钙锌pvc稳定剂

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CN103122109A (zh) * 2013-01-16 2013-05-29 江苏爱特恩高分子材料有限公司 Pvc复合热稳定剂及其应用

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8633266B2 (en) 2010-05-11 2014-01-21 Akdeniz Kimya San. ve Tic. A.S. Tin-free stabilizer composition
CN102604295A (zh) * 2012-01-12 2012-07-25 河北大学 聚合物钙锌复合皂热稳定剂、其制备方法及其应用
CN104387616A (zh) * 2014-12-16 2015-03-04 天津中财型材有限责任公司 复合Ca/Zn稳定剂及其制备方法以及环保型材
CN105585798A (zh) * 2016-02-22 2016-05-18 江苏爱特恩东台新材料科技有限公司 废聚酯制备的pvc线缆专用环保热稳定剂及其制备方法
CN105585798B (zh) * 2016-02-22 2017-07-07 盐城科迈特新材料有限公司 废聚酯制备的pvc线缆专用环保热稳定剂及其制备方法
CN106478990A (zh) * 2016-09-26 2017-03-08 深圳市志海实业股份有限公司 一种新型熔融一步法制备羟基脂肪酸钙锌pvc稳定剂

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