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WO2008084046A1 - Plastifiant pour polyvinylacétales et polysulfures - Google Patents

Plastifiant pour polyvinylacétales et polysulfures Download PDF

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Publication number
WO2008084046A1
WO2008084046A1 PCT/EP2008/050148 EP2008050148W WO2008084046A1 WO 2008084046 A1 WO2008084046 A1 WO 2008084046A1 EP 2008050148 W EP2008050148 W EP 2008050148W WO 2008084046 A1 WO2008084046 A1 WO 2008084046A1
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Prior art keywords
propyl
acid
isopropyl
tert
mixture
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German (de)
English (en)
Inventor
Boris Breitscheidel
Roland Merten
Rocco Paciello
Kai Gumlich
Joaquim Henrique Teles
Henning ALTHÖFER
Tobias Wabnitz
Hans-Detlev Gilsing
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BASF SE
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BASF SE
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
    • C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
    • B32B17/1055—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
    • B32B17/10605—Type of plasticiser
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
    • B32B17/1055—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
    • B32B17/10761—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer containing vinyl acetal
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
    • C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • 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

Definitions

  • the present invention relates to diesters of alkanediols, especially Oligoalkylenglyko- len, with Cg and / or Cio-carboxylic acids, their use as plasticizers for polyvinyl acetals and polysulfides, polymer compositions containing these diesters as plasticizers and a process for preparing these diesters.
  • plasticizers also softening, plasticizing, plasticizing and elasticizing agents
  • liquid or solid, inert organic substances with low vapor pressure which usually react without a chemical reaction, interact with high molecular weight substances and have a homogeneous system to form this. They impart certain desired properties to polymeric compositions, such as their processability or structures and coatings produced with them. As a lowered glass transition temperature, increased shape-changing capacity, increased elastic properties, reduced hardness, increased adhesion, etc.
  • Polyvinyl acetals are obtained by intramolecular (partial) acetalization of polyvinyl alcohol by reaction with aldehydes, generally short-chain aliphatic aldehydes. In addition to cyclic acetal groups, the polyvinyl acetals may also have hydroxy and acetate groups. Of technical importance are polyvinyl acetals based on formaldehyde (polyvinylformal, PVFM) and butyraldehyde (polyvinylbutyral, PVB). Polyvinyl butyral is prepared, for example, by reacting a solution of polyvinyl alcohol in water with butyraldehyde and acid. The resulting PVB fails in this process from the solution. Among other things, PVB is used to make films for the production of laminated glass systems, as coating raw materials, in dispersions for textile coatings, for adhesives and peelable coatings.
  • Plasticizers for polymer compositions used in glass processing have special requirements.
  • plasticizers for polyvinyl acetals in particular polyvinyl butyral, the diesters of aliphatic diols with aliphatic carboxylic acids and the Use diesters of dicarboxylic acids with higher alcohols. So far, di-, tri- and tetraethylene glycol esters of ethyl butyric acid, ethylhexanoic acid or n-heptanoic acid have been used so far. An overview is given for example in "Plastics Additives", pp. 381 to 385, Gumbleter and Müller, Hanser Verlag, 3rd edition, Kunststoff 1990.
  • JP 59-213750 teaches to use as plasticizer for polyvinyl butyral a mixture of a diester of Oligoalkylenglycolen with aliphatic Ci-Ci2-carboxylic acids and a diester of dicarboxylic acids with alkoxylated Ci-Ci2 alcohols.
  • DE 100 64 373 A1 describes a suitable as an intermediate layer in laminated safety glasses plasticized film on the basis of partially acetalized polyvinyl alcohols, especially PVB, the addition of amide waxes to reduce the
  • the films contain one or more plasticizers which are selected from di-n-hexyl adipate, dibutyl sebacate, dioctyl phthalate, esters of di-, tri- or tetra-glycols with linear or branched aliphatic C 6 -C 7 -carboxylic acids, polyalkylene glycols and derivatives of polyalkylene glycols, in which the hydrogen of one or both terminal hydroxyl groups is replaced by an organic radical.
  • plasticizers which are selected from di-n-hexyl adipate, dibutyl sebacate, dioctyl phthalate, esters of di-, tri- or tetra-glycols with linear or branched aliphatic C 6 -C 7 -carboxylic acids, polyalkylene glycols and derivatives of polyalkylene glycols, in which the hydrogen of one or both terminal hydroxyl groups is replaced by an organic radical.
  • Critical for polyvinyl acetals, especially PVB, is also a reduced thermal stability and / or light stability, which causes a deterioration of the optical properties, eg. B. yellowing, can cause. This is particularly problematic if the PVB thus added is used for producing films for laminated glass systems, especially car windows.
  • Critical to polysulfides is a deterioration in elasticity, too high gas permeability, deteriorated chemical resistance and deteriorated aging resistance.
  • Another disadvantage is that many known plasticizers may adversely affect transparency and / or light resistance under certain circumstances.
  • Another disadvantage is the poor synthetic accessibility of many plasticizers. In addition, often expensive raw materials lead to high prices of plasticizers. In addition, many plasticizers have inadequate cold elasticity.
  • plasticizers and softener compositions which have improved performance properties and / or which are easier to prepare. They should be distinguished in particular by a good compatibility with the plastics to which they are added and have a low volatility.
  • plasticizers and softener compositions when used as a plasticizer in a polymer composition containing at least one polyvinyl acetal, especially PVB, they should not lead to reduced thermal stability and / or light stability or adversely affect the optical properties of the polyvinyl acetal.
  • diesters of alkanediols, especially oligoalkylene glycols, with Cg and / or Cio-carboxylic acids are particularly advantageously suitable as plasticizers for PVB-containing and / or polysulfide-containing polymer compositions.
  • the invention therefore provides the use of at least one compound of general formula I.
  • X is C 2 -C 4 -alkanediyl or a straight-chain or branched hydrocarbon radical of 2 to 30 carbon atoms, the carbon chain of which contains one or more nonadjacent groups selected from O, S and NR 3 , where R 3 is hydrogen, alkyl, cycloalkyl or Aryl stands,
  • a plasticizer in a polymer composition containing at least one polymer selected from polyvinyl acetals, polysulfides and mixtures thereof.
  • the invention also provides a polymer composition
  • a polymer composition comprising at least one compound of general formula I and at least one polymer selected from polyvinyl acetals, polysulfides and mixtures thereof.
  • plasticizer is broadly understood in the context of the present invention (as defined above).
  • the use of the compounds of general formula I in particular reduces the hardness of the polymer compositions added to them compared to a composition without this additive.
  • the invention also relates to compounds of general formula I and mixtures of compounds of general formula I, as defined above and below.
  • the plasticizers used according to the invention or the polymer compositions according to the invention contain no additional phosphorus atom-containing plasticizers, especially no phosphoric acid esters.
  • the plasticizers used according to the invention or the polymer compositions according to the invention contain no compounds of the formula I defined above, wherein R 1 and R 2 are both independently of one another an alkyl radical having fewer than 8 carbon atoms.
  • plasticizers used according to the invention or the polymer compositions according to the invention preferably contain no compounds of the formula I defined above, in which R 1 and R 2 are both independently of one another an alkyl radical having more than 9 carbon atoms.
  • alkyl includes straight chain or branched alkyl groups. These are preferably straight-chain or branched C 1 -C 20 -alkyl groups, preferably C 1 -C 12 -alkyl groups.
  • Suitable Cs or Cg alkyl groups are linear or branched hydrocarbon radicals. Examples include octyl, 1-methylheptyl, 2-methylheptyl, 3-methylheptyl, 4-methylheptyl, 5-methylheptyl, 6-methylheptyl, 1-ethylhexyl, 2-ethylhexyl, 3-ethylhexyl, 4-ethylhexyl, 1, 1-dimethylhexyl, 1, 2-dimethylhexyl, 1, 3-dimethylhexyl, 1, 4-dimethylhexyl, 1, 5-dimethylhexyl, 2,3-dimethylhexyl, 2,4-dimethylhexyl, 2,5-dimethylhexyl, 1-propylpentyl, 2-propylpentyl, 1-methyl-2-ethylpentyl, 1-ethyl-1-methylpentyl, 1-ethyl-2-methylpentyl, 1-
  • a specific embodiment of the C 1 -C 4 -alkyl groups consists essentially of 1-propylhexyl or mixtures of 1-propylhexyl with one or more of its isomers 1-propyl-3-methylpentyl, 1-propyl-4-methylpentyl, 1-isopropyl hexyl, 1-isopropyl-3-methylpentyl, 1-isopropyl-4-methylpentyl and / or 1-propyl-3,3-dimethylbutyl.
  • These latter compounds are hereinafter also referred to as "propylhexyl isomers" for brevity.
  • cycloalkyl in the context of the present invention includes unsubstituted and substituted mono- or bicyclic, saturated hydrocarbons, preferably Cs-Cs-cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl or C7-Ci2-bicycloalkyl. Preferred is cyclopentyl and cyclohexyl.
  • the cycloalkyl group may carry one or more, for example one, two, three, four or five substituents.
  • these substituents are selected from alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, NR 5 R 6 and halogen, wherein R 5 and R 6 are independently hydrogen, alkyl, cycloalkyl or aryl.
  • aryl in the context of the present invention comprises a mono-, di- or trinuclear aromatic ring system containing 6 to 14 carbon ring members, which may be unsubstituted or substituted, for.
  • phenyl naphthyl and anthracenyl, more preferably phenyl.
  • the aryl group may generally carry 1, 2, 3, 4 or 5, preferably 1, 2 or 3 substituents.
  • substituents are selected from alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, halogen, and NR 5 R 6 , wherein R 5 and R 6 are independently hydrogen, alkyl, cycloalkyl or aryl.
  • R 1 and R 2 independently of one another are octyl, 1-methylheptyl, 3-methylheptyl, 5-methylheptyl, 1-ethylhexyl, 2-ethylhexyl, 1, 2-dimethylhexyl, 1, 4-dimethylhexyl, 1 Propylpentyl, 1-ethyl-3-methylpentyl, 3,4-dimethylhexyl, 2-ethyl-3-methylpentyl, nonyl, 1-propylhexyl, 1-propyl-3-methylpentyl, 1-propyl-4-methylpentyl, 1-isopropylhexyl , 1-isopropyl-3-methylpentyl, 1-isopropyl-4-methylpentyl, 1-propyl-3,3-dimethylbutyl or 2,4,4-trimethylpentyl.
  • R 1 and R 2 independently of one another are octyl, 3-methylheptyl, 5-methylheptyl, 1, 4-dimethylhexyl, 1-propylhexyl, 1-propyl-3-methylpentyl, 1-propyl-4 methylpentyl or 2,4,4-trimethylpentyl.
  • R 1 and R 2 may each have the same or different meanings.
  • R 1 and R 2 are both 1-propylhexyl or mixtures of 1-propylhexyl with one or more of the aforementioned propylhexyl isomers.
  • R 1 and R 2 are both 1-propylhexyl or a mixture of 1-propylhexyl with one or more of its isomers, which is at least 50 mole%, preferably at least 75 mole%, more preferably at least 85 mole%, 1-propyl - contains hexyl radicals. More particularly, R 1 and R 2 are both a mixture of 1-propylhexyl with 1-propyl-3-methylpentyl.
  • R 1 and R 2 are both a mixture of 1-propylhexyl with one or more of the aforementioned propylhexyl isomers containing from 50 mole% to 99.9 mole%, preferably from 75 mole% to 99 mole%. %, in particular 85 mol% to 95 mol% of 1-Propylhexylreste. Accordingly, this mixture has from 0.1 to 50 mol%, preferably from 1 to 25 mol%, in particular from 5 to 15 mol% of propylhexyl isomer radicals.
  • the group -O-X-O- is preferably a group of the formula
  • n denotes the number of repeat units and Alk represents a
  • R 4 and R 5 are independently hydrogen or methyl.
  • one of the radicals R 4 or R 5 is preferably hydrogen and the other is methyl. Furthermore, in the compounds of the formula 1.1, both radicals R 4 and R 5 are preferably hydrogen.
  • a specific embodiment are mixtures of compounds of formula 1.1 wherein R 1 and R 2 represent a mixture of 1-propylhexyl with one or more of the previously defined propylhexyl isomers.
  • R 1 and R 2 are both a mixture of 1-propylhexyl with one or more propylhexyl isomers, containing at least 50 mol%, preferably at least 75 mol%, in particular at least 85 mol%, of 1-Propylhexylreste. More particularly, R 1 and R 2 are both a mixture of 1-propylhexyl with 1-propyl-3-methylpentyl.
  • R 1 and R 2 are both a mixture of 1-propylhexyl with one or more of the aforementioned propylhexyl isomers, which is 50 mole% to 99.9 mole%, preferably 75 mole% to 99 mole%, in particular 85 mol% to 95 mol% of 1-Propylhexylreste. Accordingly, this mixture has from 0.1 to 50 mol%, preferably from 1 to 25 mol%, in particular 5 to 15 mol% of propylhexyl isomers.
  • a 1-propylhexyl / 1-propyl-3-methylpentyl ratio of about 9: 1 may be mentioned.
  • the compounds of the formula I or 1.1 can be prepared by customary processes known to the person skilled in the art. This includes the reaction of at least one diol of the formula HO-X-OH with an acid R 1 -COOH or a suitable derivative thereof and optionally an identical or different acid R 2 -COOH or a suitable derivative thereof. Suitable derivatives are, for. As the acid chlorides and acid anhydrides. As esterification catalysts, the customary catalysts can be used, for.
  • mineral acids such as sulfuric acid and phosphoric acid
  • organic sulfonic acids such as methanesulfonic acid and p-toluenesulfonic acid
  • Lewis acids in particular titanium, tin (IV) or zirconium compounds, such as tetraalkoxides, z.
  • tetrabutoxytitanium, and tin (IV) oxide are removed.
  • the esterification catalyst is used in an amount which is usually in the range of 0.05 to 5 wt .-%, preferably 0.1 to 1 wt .-%, based on the sum of acid component (or anhydride) and alcohol component.
  • Further detailed illustrations for carrying out esterification processes can be found, for example, in US Pat. No. 6,310,235, US Pat. No. 5,324,853, DE-A 2 612 355 (Derwent Abstract No. DW 77-72638 Y) or DE-A 1 945 359 (Derwent Abstract No. DW 73- 27151 U). These documents are referred to in their entirety.
  • the diols used for the preparation of the compounds of formula I HO-X-OH, especially Oligoalkylenglycole HO- (CH R 4 -CHR 5 ) -OH, are commercially available, for. B. from BASF Aktiengesellschaft Ludwigshafen.
  • Nonane and decanoic acids can be prepared by oxidation of the corresponding aldehydes or aldehyde mixtures with air on the basis of the process described in DE-A-102 39 134.
  • R 1 and / or R 2 are 2,4,4-trimethylpentyl, wherein in the event that only one of the radicals is 2,4,4-trimethylpentyl, the other is a different alkyl radical having 8 or 9 carbon atoms .
  • step d) the acid mixture obtained in step c), optionally after derivatization of the carboxylic acid function and optionally together with at least one further Cg or Cio carboxylic acid of a reaction with at least one diol of the formula HO-X-OH in the presence of an esterification catalyst subjects.
  • a hydrocarbon mixture which has a molar ratio of compounds IIa to IIb of 1: 1 to 10: 1, more preferably of 2: 1 to 8: 1, in particular of 3: 1 to 6: 1 ,
  • the hydroformylation reaction can in principle be carried out continuously, semicontinuously or discontinuously.
  • Suitable reactors for the continuous reaction are known in the art and z. As described in Ullmann's Encyclopedia of Industrial Chemistry, Vol. 1, 3rd ed., 1951, p 743 ff. Suitable pressure-resistant reactors are also known in the art and z. B. in Ullmann's Encyclopedia of Industrial Chemistry, Vol. 1, 3rd edition, 1951, p. 769 ff. Described.
  • the composition of the synthesis gas of carbon monoxide and hydrogen used in the process according to the invention can vary within wide limits.
  • the molar ratio of carbon monoxide and hydrogen is generally about 5:95 to 70:30, preferably about 40:60 to 60:40.
  • a molar ratio of carbon monoxide and hydrogen in the range of about 1: 1 is used.
  • the temperature in the hydroformylation reaction is generally in a range of about 20 to 200 0 C, preferably about 50 to 180 0 C.
  • the pressure is in a range of about 1 to 700 bar, preferably 1 to 600 bar, in particular 1 up to 300 bar.
  • the reaction pressure may vary depending on the activity of the
  • the hydroformylation catalyst according to the invention can be varied.
  • catalysts based on phosphorus-containing compounds permit reaction in a range of low pressures, such as in the range of 1 to 100 bar.
  • the hydroformylation in step b) is carried out in a preferred embodiment with rhodium catalysts homogeneously dissolved in the reaction medium, which are complexed with a phosphorus-containing ligand which has the ability to hydroformylate olefins with internal double bonds under the reaction conditions and only a relatively low tendency for the isomerization of terminal to internal double bonds.
  • the ligand is expediently used in excess with respect to the rhodium, generally with a ligand / Rh molar ratio of 2 to 300, preferably 2 to 200.
  • the rhodium concentration in the liquid reaction mixture is generally about 1 to 500 ppm by weight , preferably 2 to 350 ppm by weight.
  • rhodium salts such as rhodium acetate, rhodium chloride or rhodium nitrate
  • rhodium complexes such as Rhodiumacetylacetonat and / or Rhodi- umcarbonylENSen, such as Rh (CO) 2acac, Rh 4 (CO) ⁇ or Rh6 (CO) i6 be used (acac: acetylacetonate).
  • Rh (CO) 2acac Rh 4 (CO) ⁇ or Rh6 (CO) i6 be used (acac: acetylacetonate).
  • Rh (CO) 2acac Rh 4 (CO) ⁇
  • Rh6 (CO) i6 be used (acac: acetylacetonate).
  • the type of rhodium source used is generally not critical to the outcome of the process of the invention.
  • the rhodium compound serving as the rhodium source is generally dissolved or suspended in the reaction
  • the hydroformylation-active rhodium complex catalyst is then formed in situ in the hydroformylation reactor, under the conditions of the hydroformylation reaction, ie under the action of carbon monoxide and hydrogen on the complexed with the ligand rhodium compound. It goes without saying that preformed rhodium catalyst complexes can also be added to the reaction mixture.
  • the hydroformylation catalysts used are preferably complexes of rhodium with triarylphosphine ligands, especially triphenylphosphine.
  • the aldehyde mixture obtained in step b) preferably has a content of aldehydes of the formula III of at least 92% by weight, more preferably at least 95% by weight, in particular at least 96% by weight, based on the total aldehyde content.
  • the oxidation is usually carried out with an oxygen-containing gas in the presence or absence of a catalyst or in the presence or absence of an inhibitor.
  • the oxidizing agent to be used preferably contains molecular oxygen or oxygen-containing gas mixtures.
  • the oxygen content in the oxygen-containing gas is generally from 5 to 100% by volume.
  • the part remaining at 100% by volume is usually so-called inert gases, which are inert or at least substantially inert to the starting materials and products under the present conditions.
  • suitable inert gases are nitrogen, noble gases, carbon dioxide and water vapor.
  • Preference is given to using air as the oxygen-containing gas, which can be enriched with further oxygen as required or depleted with further inert gas, preferably nitrogen. Particular preference is given to air in the oxidation.
  • the oxidation is generally carried out at a temperature of 20 to 150 0 C.
  • the pressure is generally from 0.05 to 3 MPa absolute.
  • reactors in principle, all reactors can be used, which are suitable for gas-liquid reactions. Examples which may be mentioned are bubble columns, jet loop reactors and stirred tanks (preferably with appropriate gassing devices).
  • catalysts When catalysts are used in the oxidation, these usually include salts of metals which occur in several stable oxidation states, such as, for example, silver, cerium, cobalt, chromium, copper, iron, manganese, molybdenum, nickel or vanadium. Usually, the amount of catalyst is about 0.05 to 5% by weight based on the entire reaction mixture.
  • catalysts are used in the oxidation, these are, for example, alkali metal and alkaline earth metal salts.
  • Inhibitors primarily suppress undesirable side reactions. Preference is given to using basic salts of sodium and potassium, such as the hydroxides, oxides, acetates, carbonates and the salts of the corresponding carboxylic acids. Particularly preferred are sodium hydroxide and potassium hydroxide. Usually, the amount of inhibitor is about 0.1 to
  • the acid mixture obtained in step c) preferably has a content of isononanoic acid of the formula IV of at least 92% by weight, particularly preferably at least 95% by weight, in particular at least 96% by weight, based on the total acid content, on.
  • Suitable esterification processes for step d) are those mentioned above.
  • A) provides an aldehyde component selected from 2-propylheptanal or a mixture of 2-propylheptanal and at least one of the Cio-aldehydes
  • 2-propyl-4-methyl-hexanal, 2-propyl-5-methyl-hexanal, 2-isopropyl-heptanal, 2-isopropyl-4-methyl-hexanal, 2-isopropyl-5-methyl-hexanal and / or 2- Propyl-4,4-dimethylpentanal is, B) subjecting the aldehyde component to oxidation to give a carboxylic acid component consisting essentially of 2-propylheptanoic acid or of a mixture of 2-propylheptanoic acid and at least one of the cio-carboxylic acids 2-propyl-4-methylhexanoic acid, 2-propyl-5- methylhexanoic acid, 2-isopropylheptanoic acid, 2-isopropyl-4-methylhexanoic acid, 2-isopropyl-5-methylhexanoic acid and / or 2-propyl-4,4-dimethylpentanoic acid,
  • the Cio-aldehyde component provided in step A) is preferably derived from technically available aldehyde mixtures. Suitable C-io-aldehyde mixtures are z. B. starting from suitable C4 olefin mixtures, obtained by hydroformylation, aldol condensation and partial hydrogenation of the decenals thus obtained to decanal.
  • the isomeric composition in the 2-propylheptanal compositions useful in making the ester mixtures of this invention may vary depending on the nature of the preparation of these compositions and the type of starting material used, both in the content of individual isomers in these compositions and in the presence of certain isomers.
  • hydrocarbon As starting material for the preparation of 2-propylheptanal and its isomers, various sources of hydrocarbon may be used, for example 1-butene, 2-butene, raffinate I (ie an alkane / alkene obtained from the C4 cut of a cracker after separation of acetylene and dienes A mixture which still contains considerable quantities of isobutene in addition to 1- and 2-butene) or raffinate II which is obtained from raffinate I by separation of isobutene and only minor amounts of isobutene as olefin components other than 1- and 2-butene contains.
  • 1-butene 2-butene
  • raffinate I ie an alkane / alkene obtained from the C4 cut of a cracker after separation of acetylene and dienes A mixture which still contains considerable quantities of isobutene in addition to 1- and 2-butene
  • raffinate II which is obtained from raffinate I by separation of isobutene and
  • Suitable phosphoramidite ligands with 2,2'-dihydroxy-1, 1'-biphenylene or 2,2'-dihydroxy-1, 1 '-binaphthylen- bridging groups, the heteroaryl groups bound to the phosphorus atom via the nitrogen atom, such as pyrrolyl - or indolyl groups, are described in WO 98/19985 and WO 99/52632.
  • Suitable phosphinite ligands for the isomerizing hydroformylation with rhodium complex catalysts are u. a. the ligands described in WO 98/19985.
  • phosphite and phosphonite ligands are also suitable as ligands, as described, for example, in WO 01/58589.
  • phosphine ligands with a xanthenyl skeleton are also suitable.
  • Suitable bisphosphite chelating ligands are the subject of EP-A 213 369 and US-A 4 769 498, suitable sterically hindered monophosphite ligands are described, for example, in EP-A 155,508.
  • Suitable bidentate ligands which, in addition to a phosphite group, also carry a phosphinite or phosphine group in the ligand molecule, are described below. a. in WO 99/50214. Also possible is the hydroformylation in the presence of a complex of rhodium and a polymeric complexing ligand, in particular a polyamine, z. B. a polyethyleneimine. Such catalysts and hydroformylation conditions are described in WO 99/36382, WO 00/50373 and DE 102 56 164. The preparation of suitable Cs-aldehyde mixtures by hydroformylation of an isobutene-containing C4 feed is described in WO 2005/028407.
  • n / TPP triphenylphosphine homogeneous rhodium catalyst
  • the C ⁇ -aldehyde components obtained depending on the starting materials and catalysts used can, if desired, be separated completely or partially by distillation into the individual components, so that there is also a possibility here of influencing and controlling the isomer composition of the D-carboxylic acid component of the ester mixtures according to the invention.
  • a basic catalyst such as sodium or potassium hydroxide
  • n is formed -Valeraldehyd as the only condensation product 2-propylheptenal, whereas when using a mixture of isomeric C ⁇ -aldehydes, a mixture of isomers of the products of Homoaldolkondensation same aldehyde molecules and the crossed aldol condensation of different isomers is formed.
  • the aldol condensation can be controlled by the targeted implementation of individual isomers so that predominantly or completely a single Aldolkondensationsisomer is formed.
  • the aldol condensation products in question can then, preferably after prior, preferably distillative separation from the reaction mixture and, if desired, purification by distillation, be partially hydrogenated with known hydrogenation catalysts to the corresponding Cio aldehydes or aldehyde mixtures.
  • Such aldol condensation reactions and the partial hydrogenation of the resulting decenals to disalenals are also described in WO 2005/028407, to which reference is made in this regard.
  • the 2-propylheptanal or its mixture with the propylheptanal isomers prepared in this way may also contain other C 10 -aldehydes, for example n-decanal, methylnonanals, dimethyloctanals, ethyloctanals, trimethylheptanals, methylethylheptanals, butylhexanals, methylpropylhexanals, methylisopropenyls and the like.
  • C 10 -aldehydes for example n-decanal, methylnonanals, dimethyloctanals, ethyloctanals, trimethylheptanals, methylethylheptanals, butylhexanals, methylpropylhexanals, methylisopropenyls and the like.
  • the 2-propylheptanal is preferably used as the sole aldehyde or in admixture with one or more of the propylheptanal isomers for the Cio acid component of the ester mixtures according to the invention.
  • the content of 2-propylheptanal in the alcohols used to prepare the ester mixtures according to the invention, optionally still containing propyl heptanal isomers can be up to 100 wt .-% and is generally at least 50 wt .-%, preferably 60 to 98 wt. -% and particularly preferably 80 to 95 wt .-%, in particular 85 to 95 wt .-%.
  • Suitable mixtures of 2-propylheptanal with the propylheptanal isomers include, for example, those of 60 to 98% by weight of 2-propylheptanal, 1 to 15% by weight of 2-propyl-4-methyl-hexanal and 0.01 to 20 % By weight of 2-propyl-5-methyl-hexanal and 0.01 to 24% by weight of 2-isopropylheptanal, the sum of the proportions of the individual constituents not exceeding 100% by weight. The proportions of the individual constituents preferably add up to 100% by weight (that is, further aldehydes are absent).
  • 2-propylheptanal with the propylheptanal isomers include, for example, those from 75 to 95% by weight of 2-propylheptanal, 2 to 15% by weight of 2-propyl-4-methyl-hexanal, 1 to 20% by weight.
  • the proportions of the individual components add up to 100 wt .-%.
  • Preferred mixtures of 2-propylheptanal with the propylheptanal isomers include those having from 85 to 95% by weight of 2-propylheptanal, from 6 to 12% by weight of 2-propyl-4-methylhexanal and from 0.1 to 2% by weight .-% 2-propyl-5-methylhexanal and 0.01 to 1 wt .-% 2-isopropylheptanal, wherein the sum of the proportions of the individual components does not exceed 100 wt .-%.
  • the proportions of the individual components add up to 100 wt .-%.
  • Preferred mixtures of 2-propylheptanal with the propylheptanol isomers furthermore include, for example, those of 80 to 92% by weight of 2-propylheptanal, 6 to 12% by weight of 2-propyl-4-methyl-hexanal, 7 to 13% by weight.
  • the proportions of the individual components add up to 100 wt .-%.
  • R 1 and R 2 can only assume those meanings which correspond to the alkyl radicals of the carboxylic acids used in each case specifically for the esterification.
  • Such mixtures of compounds of the formula I (or 1.1) are in the context of the invention also referred to as compounds of the formula I (or 1.1) in which R 1 and R 2 are each independently an (alkyl group) - mixture of 1- Propylhexyl and at least one of the propylhexyl isomers 1-propyl-3-methyl-pentyl, 1-propyl-4-methyl-pentyl, 1-isopropyl-hexyl, 1-isopropyl-3-methyl-pentyl, 1-isopropyl-4 methyl-pentyl and / or 1-propyl-3,3-dimethylbutyl.
  • polyvinyl butyral is used in a three-stage process over polyvinyl alcohol, starting from acetylene and acetic acid for the preparation of vinyl acetate as Monomer produced. Since vinyl alcohol is unstable as a free compound and is not available for polymerization, a reaction of the polyvinyl acetate by saponification in the presence of methanol to polyvinyl alcohol. Acetalization of the polyvinyl alcohol with butyraldehyde in an acidic medium gives polyvinyl butyral.
  • Variants of the PVB resin are achieved, for example, by the choice of molecular weight from the starting polyvinyl acetate, by the degree of hydrolysis to polyvinyl alcohol, and by the amount of butyraldehyde used for the acetalization. Accordingly, PVB may also be understood as a terpolymer of vinyl acetate, vinyl alcohol and vinyl butyral.
  • the properties of PVB are determined primarily by the proportion of free hydroxyl groups, which is determined by the degree of hydrolysis of the polyvinyl acetate to polyvinyl alcohol and by the amount of butyraldehyde used in the acetalization.
  • the proportion of free hydroxyl groups is generally 5 to 50%, preferably 10 to 40% and particularly preferably 15 to 25%.
  • the polymer composition according to the invention or used with a plasticizer according to the invention comprises at least one polyvinyl butyral having a hydroxyl number (determined according to ASTM D 1396-92) in the range of 17 to 23 wt .-%, particularly preferably 18 to 21 wt .-%.
  • Such polymer compositions are advantageously suitable for the production of films, especially for the production of films for laminated glass systems.
  • the softening temperature of the PVB is 80 to 150 ° C., especially 90 to 140 ° C.
  • PVB films typically have a thickness of 0.1 to 2 mm, especially 0.4 to 1.5 mm.
  • a polysulfide is understood as meaning a polymer which has thioether groups.
  • the polysulfides may be linear or branched or crosslinked.
  • the polysulfides used according to the invention may also have further functional groups in the main chain or in a side chain. Other functional groups are especially ether groups, aromatic groups or urethane groups.
  • the polysulfides used according to the invention are preferably polymeric alkyl thioethers, where the alkyl groups can be linear or branched.
  • the polymeric compositions according to the invention may also comprise two or more than two different polysulfides.
  • Polysulfides are obtained in particular by polycondensation of alkali metal polysulfides, for example sodium pentasulfide, with alkyl dihalides, such as. B. 1, 2-dichloroethane and bis (2-chloroethoxy) methane produced. It is also possible to add trihalides, for example 1,2,3-trichloropropane, for crosslinking.
  • alkali metal polysulfides for example sodium pentasulfide
  • alkyl dihalides such as. B. 1, 2-dichloroethane and bis (2-chloroethoxy) methane produced.
  • trihalides for example 1,2,3-trichloropropane
  • the polysulfides present in the mixtures according to the invention are temperature-resistant in a range from -50 to 125 ° C., in particular from -35 to 100 ° C.
  • Polysulfides are used, for example, for the production of sealants, in particular sealants for insulating glass.
  • the polymer compositions of the invention preferably comprise at least one polymer selected from polyvinyl acetals and / or polysulfides in an amount of from 20 to 99% by weight, more preferably from 45 to 95% by weight, in particular from 50 to 90% by weight. %, and especially at 55 to 85 wt .-%, based on the total weight of the composition (the sum of all components, ie compounds of formula I, polyvinyl acetals and / or polysulfides, if any more polymers and, if present, other additives).
  • the compounds of the formula I which are used according to the invention can optionally be used together with at least one light stabilizer which absorbs light radiation in the UV-A and / or UV-B range and / or other (co) stabilizers in the polymer compositions.
  • the light stabilizers are preferably colorless in the visible range or have only a slight inherent color on.
  • the optionally used light stabilizers or (co) stabilizers preferably have a high migration stability and temperature resistance. Suitable light stabilizers and further (co) stabilizers are selected, for example, from groups a) to s):
  • the group a) of the 4,4-diarylbutadienes include, for example, compounds of the formula
  • the compounds are known from EP-A-916 335.
  • the substituents R 1 and / or R n are preferably d-Cs-alkyl and Cs-Cs-cycloalkyl.
  • the group b) of cinnamic acid esters includes, for example, 2-isoamyl 4-methoxycinnamate, 2-ethylhexyl 4-methoxycinnamate, methyl ⁇ -methoxycarbonyl cinnamate, methyl ⁇ -cyano- ⁇ -methyl-p-methoxycinnamate, butyl ⁇ - cyano-.beta.-methyl-p-methoxycinnamate and methyl-.alpha.-methoxycarbonyl-p-methoxycinnamate.
  • the group c) of the benzotriazoles includes, for example, 2- (2'-hydroxyphenyl) benzotriazoles, such as 2- (2'-hydroxy-5'-methylphenyl) benzotriazole, 2- (3 ', 5'-di-tert-butyl- 2'-hydroxyphenyl) benzotriazole, 2- (5'-tert-butyl-2'-hydroxyphenyl) benzotriazole, 2- (2'-hydroxy-5 '- (1, 1, 3,3-tetramethylbutyl) phenyl ) benzotriazole, 2- (3 ', 5'-di-tert-butyl-2'-hydroxyphenyl) -5-chloro-benzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5'-methylphenyl) 5-chloro-benzotriazole, 2- (3'-sec-butyl-5'-tert-butyl-2'-hydroxyphenyl) -benzotriazole, 2- (2'-hydroxy
  • the group e) of the diphenylcyanoacrylates includes, for example, ethyl-2-cyano-3,3-diphenylacrylate, which is obtainable, for example, commercially under the name Uvinul® 3035 from BASF AG, Ludwigshafen, 2-ethylhexyl-2-cyano-3, 3-diphenylacrylate, which is commercially available, for example, as Uvinul® 3039 from BASF AG, Ludwigshafen, and 1, 3-bis - [(2'-cyano-3 ', 3'-diphenylacryloyl) oxy] -2,2 -bis ⁇ [2'-cyano- 3 ', 3'-diphenylacryloyl) oxy] methyl ⁇ propane, which is commercially available, for example, under the name Uvinul® 3030 from BASF Aktiengesellschaft, Ludwigshafen.
  • tocopherols such as. b. ⁇ -tocopherol, ⁇ -tocopherol, ⁇ -tocopherol, ⁇ -tocopherol and mixtures thereof (vitamin E).
  • acylaminophenols such as 4-hydroxy-lauric acid anilide, 4-hydroxystearic acid anilide, 2,4-bis-octylmercapto-6- (3,5-di-tert-butyl-4-hydroxyanilino) -s-triazine and octyl-N- (3 , 5-di-tert-butyl-4-hydroxyphenyl) -carbamate.
  • esters of ß- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid with monohydric or polyhydric alcohols such.
  • 3-thiaundecanol 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo [2.2.2] octane.
  • 2,6-di-tert-butyl-4-dimethylaminomethylphenol 2,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, N, N, N ', N'-tetramethyl-4,4'-diaminodiphenylmethane, 1, 2 -Bis - [(2-methylphenyl) amino] ethane, 1, 2-bis (phenylamino) -propane, (o-tolyl) biguanide, bis [4- (1 ', 3'-dimethylbutyl) phenyl] amine, tert -octylated N-phenyl-1-naphthylamine, mixture of mono- and dialkylated tert-butyl / tert-butyl
  • Octyldiphenylamines mixture of mono- and dialkylated nonyldiphenylamines, mixture of mono- and dialkylated dodecyldiphenylamines, mixture of mono- and dialkylated isopropyl / isohexyl-diphenylamines, mixture of mono- and dialkylated tert-butyldiphenylamines, 2,3-dihydro-3, 3-dimethyl-4H-1,4-benzothiazine, phenothiazine, mixture of mono- and dialkylated tert-butyl / tert-octyl-phenothiazines, mixture of mono- and dialkylated tert-octyl-phenothiazines, N-allylphenothiazine, N, N, N ', N'-tetraphenyl-1,4-diaminobut-2-ene, N, N-bis (2,2,6,6-tetra
  • nickel compounds include, for. B. nickel complexes of 2,2'-thio-bis [4- (1, 1, 3,3-tetramethylbutyl) phenol], such as the 1: 1 or 1: 2 complex, optionally with additional ligands such n-butylamine, triethanolamine or N-cyclohexyl-diethanolamine, nickel dibutyldithiocarbamate, nickel salts of 4-hydroxy- 3,5-di-tert-butylbenzylphosphonic acid monoalkyl esters, such as e.g. As the methyl or ethyl ester, nickel complexes of ketoximes such.
  • Example of 2-hydroxy-4-methylphenylundecyl ketoxime nickel complex of 1-phenyl-4-lauroyl-5-hydroxypyrazole, optionally with additional ligands.
  • 4-piperidyl) hexamethylenediamine and formic acid ester (CAS No. 124172-53-8, for example Uvinul® 4050H from BASF Aktiengesellschaft, Ludwigshafen), condensation product of 2-chloro-4,6-bis (4-n-pyridine) butylamino-2, 2,6,6-tetramethylpiperidyl) -1,3,5-triazine and 1,2-bis (3-aminopropylamino) ethane, condensation product of 2-chloro-4,6-di- (4-n-) butylamino-1, 2,2,6,6-pentamethylpiperidyl) -1, 3,5-triazine and
  • N- (2,2,6,6-tetramethyl-4-piperidyl) -n-dodecylsuccinimide N- (1) - pentamethyl -piperidyl-n-dodecylsuccinimide, 2-undecyl-7,7,9 , 9-tetramethyl-1-oxa-3,8-diaza-4-oxospiro [4,5] decane, reaction product of 7,7,9,9-tetramethyl-2-cycloundecyl-1-oxa-3,8-diaza - 4-oxospiro [4,5] decane and epichlorohydrin, 1,1-bis (1,2,2,6,6-pentamethyl-4-piperidyloxycarbonyl) -2- (4-methoxyphenyl) ethene, N, N ' Bis-formyl-N, N'-bis (2,2,6,6-tetramethyl-4-piperid
  • the group k) of the metal deactivators include, for. N, N'-diphenyloxalic acid diamide, N-salicylal-N'-salicyloyl-hydrazine, N, N'-bis (salicyloyl) hydrazine, N, N'-bis (3,5-di-tert-butyl-4- hydroxyphenylpropionyl) hydrazine, 3-salicyloylamino-1, 2,4-triazole, bis (benzylidene) oxalyl dihydrazide, oxanilide, isophthaloyl dihydrazide, sebacoyl bisphenyl hydrazide, N, N'-diacetyl adipic dihydrazide, N, N'-bis (salicyloyl) oxalic dihydrazide, N, N '-bis (salicyloyl) thiopropiony
  • the group I) of the phosphites and phosphonites include, for. B. triphenyl phosphite, diphenylalkyl phosphites, phenyl dialkyl phosphites, tris (nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite, distearyl pentaerythritol diphosphite, tris (2,4-di-tert-butylphenyl) phosphite, diisodecylpentaerythritol diphosphite, bis (2,4-di-tert-butylphenyl) pentaerythritol diphosphite, bis (2,6-di-tert-butyl-4-methylphenyl) pentaerythritol diphosphite, diisodecyloxypentaerythri
  • the group m) of the hydroxylamines include, for. N, N-dibenzylhydroxylamine, N, N-diethylhydroxylamine, N, N-dioctylhydroxylamine, N, N-dilaurylhydroxylamine, N, N-ditetradecylhydroxylamine, N, N-dihexadecylhydroxylamine, N, N-dioctadecylhydroxylamine, N-hexadecyl N-octadecylhydroxylamine, N-heptadecyl-N-octadecylhydroxylamine, N-methyl-N-octadecylhydroxylamine and N, N-dialkylhydroxylamine from hydrogenated tallow fatty amines.
  • the group n) of the nitrenes include, for. N-benzyl- ⁇ -phenylnitrone, N-ethyl- ⁇ -methylnitrone, N-octyl- ⁇ -heptylnitrone, N-lauryl- ⁇ -undecylnitrone, N-tetradecyl- ⁇ -tridecylnitrone, N-hexadecyl- ⁇ -pentadecylnitrone, N-octadecyl- ⁇ -heptadecyl nitrone, N-hexadecyl- ⁇ -heptadecyl nitrone, N-octadecyl- ⁇ -pentadecyl nitrone, N-heptadecyl- ⁇ -heptadecyl nitrone, N-octadecyl- ⁇ -hexadecyl nitrone, N-methyl- ⁇ -hept
  • the group o) of the amine oxides include, for.
  • amine oxide derivatives as disclosed in U.S. Pat. Nos. 5,844,029 and 5,880,191 didecylmethylamine oxide, tridecylamine oxide, tridodecylamine oxide and trihexadecylamine oxide.
  • the group p) of the benzofuranones and indolinones include, for. Those disclosed in U.S. Patents 4,325,863; 4,338,244; 5,175,312; 5,216,052; 5,252,643; in the
  • the group q) of the thiosynergists includes, for example, Dilauryl thiodipropionate or distearyl thiodipropionate.
  • the group r) the peroxide-destroying compounds include, for. B. esters of ⁇ -Thiodipropionklare, z.
  • the group s) of basic costabilizers include, for. As melamine, polyvinyl pyrrolidone, dicyandiamide, triallyl cyanurate, urea derivatives, hydrazine derivatives, amines, polyamides, polyurethanes, alkali metal and alkaline earth metal salts of higher fatty acids, eg. Calcium stearate, zinc stearate, magnesium behenate, magnesium stearate, sodium ricinoleate and potassium palmitate, antimony catecholate or zinc catechinate.
  • melamine polyvinyl pyrrolidone, dicyandiamide, triallyl cyanurate, urea derivatives, hydrazine derivatives, amines, polyamides, polyurethanes, alkali metal and alkaline earth metal salts of higher fatty acids, eg. Calcium stearate, zinc stearate, magnesium behenate, magnesium stearate, sodium ricinoleate and
  • the polymer compositions of the invention preferably have the light stabilizers in an amount of 0.01 to 7 wt .-%, particularly preferably 0.1 to 5 wt .-%, in particular 0.2 to 4 wt .-%, and especially 0.5 to 3 wt .-%, based on the total weight of the composition on.
  • Lubricants should be effective between the polyvinyl acetal or the polysulfide particles and counteract frictional forces during mixing, plasticizing and deforming.
  • the polymer compositions according to the invention may contain all lubricants customary for the processing of plastics.
  • hydrocarbons such as oils, paraffins and polyethylene waxes
  • Fatty alcohols preferably having 6 to 20 C atoms
  • Ketone Carboxylic acids, such as fatty acids (eg, montanic acid); oxidized polyethylene waxes; Metal salts of carboxylic acids; Carboxylic acid amides and carboxylic acid esters, wherein the alcohol component is, for example, selected from ethanol, fatty alcohols, glycerol, ethanediol and pentaerythritol and the carboxylic acid component is, for example, selected from long-chain carboxylic acids.
  • the polymer compositions according to the invention preferably contain the lubricants in an amount of from 0.01 to 10% by weight, more preferably from 0.05 to 5% by weight, in particular from 0.1 to 3% by weight, and especially from 0.2 to 2 wt .-%, based on the total weight of the composition on.
  • Suitable nucleating agents are, for example, inorganic substances, such as talc, metal oxides, such as titanium dioxide or magnesium oxide, phosphates, carbonates or sulfates of, preferably, alkaline earth metals; organic compounds such as mono- or polycarboxylic acids and the salts thereof, for example 4-tert-butylbenzoic acid, adipic acid, diphenylacetic acid, sodium succinate or sodium benzoate; polymeric compounds, such as ionic copolymers (ionomers). Particularly preferred
  • Suitable fillers or reinforcing agents include, for. As calcium carbonate, silicates, talc, mica, kaolin, mica, barium sulfate, metal oxides and hydroxides, carbon black, graphite, wood flour and flours or fibers of other natural products, synthetic fibers.
  • fibrous or powdery fillers are also carbon or glass fibers in the form of glass fabrics, glass mats or glass silk rovings, chopped glass, glass beads and wollstonite into consideration.
  • the incorporation of glass fibers can take place both in the form of short glass fibers and in the form of continuous fibers (rovings).
  • fillers have a positive influence on the compressive, tensile and flexural strength as well as the hardness and heat resistance of plasticized polyvinyl acetal and plasticized polysulfide.
  • the polymer compositions according to the invention preferably contain the fillers and reinforcing agents in an amount of from 0.01 to 80% by weight, more preferably from 0.1 to 60% by weight, in particular from 0.5 to 50% by weight, and especially 1 to 40% by weight, based on the total weight of the composition.
  • colorant includes both dyes and pigments.
  • the colorant is a pigment.
  • the pigment may be an inorganic or organic pigment.
  • colorants are organic compounds which have fluorescence in the visible part of the electromagnetic spectrum, such as fluorescent dyes.
  • the colorant may also have other properties such as electrical conductivity or be magnetically shielding.
  • non-pigmented or blended with transparent pigments polymer compositions are used.
  • the use of pigmented polymer compositions may be advantageous.
  • Suitable inorganic color pigments are white pigments such as titanium dioxide in its three modifications rutile, anatase or brookite, lead white, zinc white, zinc sulfide or lithopone; Black pigments such as carbon black, iron oxide black, iron manganese black or spinel black; Colored pigments such as chromium oxide, chromium oxide hydrate green, cobalt green or ultramarine green, cobalt blue, iron blue, milori blue, ultramarine blue or manganese blue, ultramarine violet or cobalt and manganese violet, iron oxide red, cadmium sulfoselenide, molybdate red or ultramarine red; Iron oxide brown, mixed brown, spinel and corundum phases or chrome orange; Iron oxide yellow, nickel titanium yellow, chromium titanium yellow, cadmium sulfide, cadmium zinc sulfide, chrome yellow, zinc yellow, alkaline earth chromate, Naples yellow; Bismuth vanadate, effect pigments such as
  • Suitable inorganic pigments include: Pigment White 6, Pigment White 7, Pigment Black 7, Pigment Black 1 1, Pigment Black 22, Pigment Black 27/30, Pigment Yellow 34, Pigment Yellow 35/37, Pigment Yellow 42, Pigment Yellow Pigment Brown 24, Pigment Yellow 184, Pigment Yellow 184, Pigment Yellow 20, Pigment Orange 20, Pigment Orange 75, Pigment Brown 6, Pigment Brown 29, Pigment Brown 31, Pigment Yellow 164, Pigment Red 101, Pigment Red 104, Pigment Red 108, Pigment Red 265, Pigment Violet 15, Pigment Blue 28/36, Pigment Blue 29, Pigment Green 17, Pigment Green 26/50.
  • suitable organic pigments include aniline black, Anthrapyrimidinpig- elements, elements azomethine pigments, anthraquinone pigments, monoazo pigments, Bisazopig-, benzimidazolone pigments, quinacridone pigments, quinophthalone pigments, diketone topyrrolopyrrolpigmente, elements dioxazine, flavanthrone, Indanthronpig-, Indolinonpigmente, isoindoline pigments, isoindolinone pigments, Thioindigopig- elements, Metal complex pigments, perinone pigments, perylene pigments, pyranthrone pigments, phthalocyanine pigments, thioindigo pigments, triaryl carbonium pigments or metal complex pigments.
  • Suitable organic pigments include: Cl. (Color Index) Pigment Yellow 93, Cl. Pigment Yellow 95, Cl. Pigment Yellow 138, Cl. Pigment Yellow 139, Cl. Pigment Yellow 155, Cl. Pigment Yellow 162, Cl. Pigment Yellow 168, Cl. Pigment Yellow 180, Cl. Pigment Yellow 183, Cl. Pigment Red 44, Cl. Pigment Red 170, Cl. Pigment Red 202, Cl. Pigment Red 214, Cl. Pigment Red 254, Cl. Pigment Red 264, Cl. Pigment Red 272, Cl. Pigment Red 48: 2, Cl. Pigment Red 48: 3, Cl. Pigment Red 53: 1, Cl. Pigment Red 57: 1, Cl. Pigment Green 7, Cl. Pigment Blue 15: 1, Cl. Pigment Blue 15: 3, Cl. Pigment Violet 19.
  • pigments mentioned can also function as fillers or reinforcing agents and / or as nucleating agents.
  • Suitable dyes are: azo dyes, pyrazolone dyes, anthraquinone dyes, perinone dyes, perylene dyes, indigo and thioindigo dyes and azomethine dyes.
  • the polymer compositions according to the invention preferably contain the colorants in an amount of from 0.01 to 10% by weight, more preferably from 0.05 to 5% by weight, in particular from 0.1 to 3% by weight, and especially from 0.5 to 2 wt .-%, based on the total weight of the composition on.
  • the polymer compositions of the invention may also contain flame retardants.
  • Suitable flame retardants are organic chlorine and bromine compounds such as chloroparaffins, antimony trioxide, phosphorus compounds such as phosphate esters, aluminum hydroxide, boron compounds, molybdenum trioxide, ferrocene, calcium carbonate or magnesium carbonate.
  • the polymer compositions of the invention preferably have the flame retardants in an amount of 0.01 to 10 wt .-%, particularly preferably 0.1 to 8 wt .-%, in particular 0.2 to 5 wt .-%, and especially 0.5 to 3 wt .-%, based on the total weight of the composition on.
  • Suitable propellants are propane, butane or pentane.
  • the mixtures according to the invention comprising polyvinyl butyral or polysulfides may contain as additives in particular also regulators for the adhesion behavior towards glass, such as, for example, sodium salts, in particular sodium acetate and sodium lecithin.
  • the mixtures according to the invention comprising at least one poly sulfide as additives may also contain phenolic resins, epoxy- and mercapto-functionalized silanes or epoxy resins.
  • the mixtures according to the invention comprising polysulfides may, for example, also contain curing agents such as lead dioxide, calcium peroxide, zinc peroxide or manganese dioxide.
  • the polymer composition additionally contains at least one compatibility improver.
  • This serves to reduce or avoid any incompatibilities between the polymer component and the plasticizer component, e.g. B. to limit an undesirable release of the plasticizer from the polymer composition to an acceptable level or preferably completely avoided.
  • at least one compatibility improver is used in a polymer composition according to the invention which contains at least one polyvinyl acetal.
  • at least one compatibilizer is employed in a polymer composition of the invention containing at least one polyvinyl butyral.
  • It is preferably a polyvinyl butyral having a vinyl alcohol content (hydroxyl number determined according to ASTM D 1396-92) of at least 15% by weight, more preferably at least 16% by weight, especially at least 17% by weight, especially at least 18% by weight .-%.
  • the compatibilizer is preferably selected from nonionic surfactants.
  • Suitable nonionic surfactants are, for example, the reaction products of straight-chain or branched, saturated or mono- or polyunsaturated alcohols having 6 to 30 carbon atoms in the alkyl chain with at least one alkylene oxide.
  • Alkylene oxides suitable for alkoxylation are ethylene oxide, propylene oxide, butylene oxide and mixtures thereof. Preferred are ethylene oxide and ethylene oxide / propylene oxide mixtures. Different alkylene oxide units can be arranged in blocks or randomly distributed. Per mole of alcohol, these surfactants usually contain 2 to 50 mol, preferably 3 to 20 mol, of at least one alkylene oxide.
  • fatty alcohol alkoxylates examples which may be mentioned are fatty alcohol alkoxylates, oxo alcohol alkoxylates and guerbet alcohol ethoxylates.
  • Such surfactants are commercially available, for. B. in the form of the Lutonsol ® brands of BASF Aktiengesellschaft.
  • Suitable nonionic surfactants are furthermore the reaction products of alkylphenols having 6 to 20 C atoms in the alkyl chain with at least one alkylene oxide.
  • Alkylene oxides suitable for alkoxylation are those mentioned above. Preferred are ethylene oxide and ethylene oxide / propylene oxide mixtures. Per mole of alcohol, these surfactants usually contain 2 to 50 mol, preferably 3 to 20 mol, of at least one alkylene oxide. Examples which may be mentioned are ethoxylated octyl, isooctyl or nonylphenol.
  • nonionic surfactants are alkylamine oxides, mono- or dialkylalcanolamides, fatty acid esters of polyethylene glycols, alkoxylated (preferably ethoxylated) fatty acid amides, sugar surfactants, sorbitol esters, such as sorbitan fatty acid esters (eg sorbitan monooleate and sorbitan tristearate), polyoxyethylene sorbitan fatty acid esters, alkyl polyols. glycosides, N-alkylgluconamides, alkylmethylsulfoxides, alkyldimethylphosphine oxides such as tetradecyldimethylphosphine oxide, and mixtures thereof.
  • the aforementioned surfactants can be used to improve compatibility individually or in the form of mixtures of two or more than two surfactants.
  • Preferred nonionic surfactants are isoalkanol alkoxilates, especially isotridecanolethoxilates. These include z. For example, the Lutensol ® TO grades of BASF Akiengesellschaft. These include z. As the Marlipal ® O13 brands of Sasol. A special commercially available compatibility enhancer is Marlipal 013/40 (oligomeric ethylene glycol, consisting of four ethylenedioxy units, one-sidedly substituted with isotridecanrest at one of the two hydroxyl-terminated ends). Further preferred nonionic surfactants are C 12-18 fatty alcohol alkoxilates, especially C 12 / C 14 fatty alcohol ethoxylates. These include z.
  • Lutensol® A (3, 12, ...) N brands and the Lutensol® AT brands of BASF Akiengesellschaft. These include z.
  • Marlipal ® 24 brands of Sasol A specific commercially available compatibility enhancer is Marlipal® 24/50 (oligomeric ethylene glycol mixture consisting of five ethylenedioxy units, monosubstituted with Ci2 / 14-alkyl radical at one of the two hydroxyl-terminated ends).
  • Preferred nonionic surfactants are furthermore (C 6 -C 14 -alkyl) phenol alkoxylates, especially ethoxylates. These include z.
  • C 6 -C 14 -alkyl phenol alkoxylates especially ethoxylates.
  • These include z.
  • a particular commercially available compatibilizer is Marlophen NP6 (oligomeric ethylene glycol consisting of six ethylenedioxy units, one-sidedly substituted with 4-nonylphenyl at one of the two hydroxyl-terminated ends).
  • the polymer compositions according to the invention preferably contain at least one compatibility improver in an amount of from 0.1 to 15% by weight, more preferably from 0.5 to 10% by weight, in particular from 1 to 8% by weight, based on the total weight of the composition.
  • the compatibility improvers incompatibilities between the polymer component and the plasticizer component, the z. B. polarity differences between polymer and plasticizer may be due to reduce or avoid.
  • the compatibilizer also has no otherwise adverse effect on the mechanical properties of the polymer composition.
  • the polymer composition according to the invention may additionally contain at least one further polymer.
  • Preferred further polymers are selected from polyolefin homopolymers and copolymers, polytetrafluoroethylenes, ethylene-tetrafluoroethylene copolymers, polyvinyl chlorides, polyvinylidene chlorides, polyvinyl alcohols, polyvinyl esters, polyvinylalkanals, polyamides, polyimides, polycarbonates, polyesters, poly (meth) acrylates, polyurethanes, Poly (vinylaromatic) homopolymers and copolymers, polyethers, polyether ketones and mixtures thereof.
  • the polymer composition according to the invention additionally comprises at least one further polymer which is selected from homo- and copolymers based on ethylene, propylene, butadiene, vinyl chloride, vinyl acetate, glycidyl acrylate, glycidyl methacrylate, acrylates and methacrylates with alcohol components of branched or unbranched C 1 to C 10 alcohols, styrene or acrylonitrile.
  • polyacrylates with the same or different alcohol radicals from the group of C 4 - to Cs-alcohols, in particular of the butanol, hexanol, octanol and 2-ethylhexanol, polymethyl methacrylate, polyvinyl chloride, methyl methacrylate-butyl acrylate copolymers, methyl methacrylate-butyl methacrylate Copolymers, ethylene-vinyl acetate copolymers, chlorinated polyethylene, nitrile rubber, acrylonitrile-butadiene-styrene copolymers, ethylene-propylene copolymers, ethylene-propylene-diene copolymers, styrene-acrylonitrile copolymers, acrylonitrile-butadiene rubber, styrene-butadiene Elastomers and methyl methacrylate-styrene-butadiene copolymers
  • the polymer composition according to the invention additionally contains at least one further polymer which is transparent or at least translucent.
  • Such polymers are especially suitable for use of the polymer composition in glassmaking and processing. Examples which may be mentioned are: polyethylene, polypropylene, polyamide 6, polyamide 66, polycarbonate, polycarbonate-polyethylene terephthalate blends, polycarbonate-polybutylene terephthalate blends, polycarbonate-acrylonitrile / styrene / acrylonitrile copolymer blends, polycarbonate-acrylonitrile / Butadiene / styrene copolymer blends, methyl methacrylate-acrylonitrile / butadiene / styrene polymer (MABS), polyethylene terephthalate, polybutylene terephthalate, polymethyl methacrylate, impact modified polymethyl methacrylate, polybutyl acrylate, polymethyl methacrylate polyvinylidene difluor
  • ABS styrene / acrylonitrile copolymers
  • ASA acrylonitrile / styrene / acrylic ester polymer
  • the compounds of the formula I used according to the invention and, if present, the light stabilizers of groups a) to s) and / or the other additives are added to the polymer composition.
  • the addition is done in the usual way, for example by mixing with the plastic.
  • the compounds of the formula I used according to the invention and, if appropriate, the additives are added to the starting monomers and the mixture of monomers, compounds of the formula (I) and, if appropriate, the additives is polymerized.
  • the compounds of the formula I used according to the invention and, if appropriate, the additives are added during the polymerization of the monomers.
  • a precondition for an addition before or during the polymerization is that the compound of the formula I used according to the invention and, if appropriate, the additives are stable under the polymerization conditions, ie they do not decompose or only slightly decompose.
  • the compounds of the formula I used according to the invention and, if present, the light stabilizers of groups a) to s) and / or the other additives are added to the finished polymer or to a mixture of finished polymers. This is done in the usual way according to known mixing method. This includes mixing with melting, preferably at temperatures of 100 to 300 ° C. However, the components can also be mixed "cold" without melting, and the powdery or granular mixture is first melted and homogenized during processing.
  • the compounds of the formula I used according to the invention and, if present, the light stabilizers of groups a) to s) and / or the other additives together or separately from each other, all at once, in portions or continuously over the time constant or with a gradient, can inflict.
  • some of the compounds of the formula I used according to the invention can be added to the monomers during the polymerization and the remainder added to the finished polymer, or the entire amount of the compounds of the formula I can be added to the finished polymer.
  • the compound of the formula I used according to the invention is preferably added to the plastics in the form of a premix (masterbatch or compound). Furthermore, the premix may contain the aforementioned light stabilizers of groups a) to s) and other additives.
  • the blending is preferably carried out in a conventional extruder, wherein the components can be mixed or introduced individually into the extruder or else introduced proportionately at a later point of the extruder to the molten or solid product in the extruder.
  • a conventional extruder wherein the components can be mixed or introduced individually into the extruder or else introduced proportionately at a later point of the extruder to the molten or solid product in the extruder.
  • single or twin-screw extruders are particularly suitable for melt extrusion.
  • the resulting polymer compositions can be pelleted (or granulated), for example, or processed by well-known methods, for example by extrusion, injection molding, foaming with blowing agents, thermoforming, blow molding or calendering.
  • the mixtures according to the invention are particularly suitable because of the low volatility of the diesters according to the invention and the high compatibility of the components, ie the diester and the polyvinyl butyral or the diester and the poly-sulfide, for the production of softened PVB articles or polysulfide -Artikeln.
  • the invention also relates to the use of a mixture comprising at least one polyvinyl acetal, in particular polyvinyl butyral, and a diester of an ethylene or propylene glycol and a nonyl or decylcarboxylic acid or a comprising at least one polysulfide and a diester of an ethylene or propylene glycol and a nonyl or decylcarboxylic acid in housings for electrical appliances, such as kitchen appliances and computer housings, piping, apparatus, cables, wire sheathing, window profiles, interior fittings, in the vehicle and furniture, in floor coverings, medical articles, food packaging, gaskets, sealants, sealants for insulating glass, films, laminated films, films for laminated safety glass, in particular for the vehicle sector and the architectural sector, records, artificial leather, toys, packaging containers, adhesive tape, Clothing, coatings, being fibers for fabrics.
  • electrical appliances such as kitchen appliances and computer housings, piping, apparatus, cables, wire sheathing, window profiles, interior
  • the invention also relates to articles comprising a mixture comprising at least one polyvinyl acetal, in particular polyvinyl butyral, and a diester of an ethylene or propylene glycol and a nonyl or Decylcarbonklare or a mixture comprising at least one polysulfide and a diester of an ethylene or propylene glycol and a nonyl or decylcarboxylic acid.
  • An article according to the invention may include, for example, a housing for electrical appliances, a pipeline, a device, a cable, a wire sheath, a window profile, a floor covering, a medical article, a toy, a food packaging, a seal, a sealant, a sealant for insulating glass , a film, a composite film, a laminated safety glass film, in particular for the automotive sector and the architectural sector, a record, artificial leather, a packaging container, an adhesive tape, clothing, a coating or a fiber for tissue.
  • PVB articles produced by means of the mixtures according to the invention are distinguished by high strength, very good extensibility and outstanding adhesion to glass surfaces. This makes it possible to produce very flexible films with good transparency and light resistance and very good glass adhesion, which is particularly important for use as films for the production of laminated safety glass.
  • the strength and ductility of PVB films is determined in particular by the Shore hardnesses A and D (determination according to DIN 53505), the fracture stress (determination according to DIN EN ISO 527, part 1 and 3), the elongation at break (determined according to DIN EN ISO 527 , Part 1 and 3) and the stress at 100% elongation (determined according to DIN EN ISO 527, Part 1 and 3).
  • Polysulfide sealants prepared, for example, with the mixtures according to the invention are distinguished, in addition to high elasticity and low gas permeability, in particular by good weather resistance, good chemical resistance, in particular swelling resistance, and good resistance to aging.
  • PVB film samples based on a PVB resin having a higher vinyl alcohol content (> 18% by weight), a plasticizer used according to the invention and a compatibility improver do not show any exudation of the plasticizer even after storage for 30 days at 99% relative humidity.
  • Such a polymer composition also shows a significantly improved low-temperature resistance up to at least - 70 0 C.
  • PVB films based on such a polymer composition additionally also have very good optical properties.
  • Laminated glass panes made with them are characterized by a high light transmission with a very low yellow value.
  • the plasticizer used in the invention also has a lower tendency to escape and volatility than the standard plasticizer 3G8.
  • a 2-liter autoclave with reflux condenser was charged with 340 g of a potassium acetate solution (28 g of KOH in 312 ml of HOAc) and with 10.65 kg of a do-aldehyde mixture (2-propylheptanal and 2-propyl-4-methylhexanal in a weight ratio of 9 : 1) offset.
  • a potassium acetate solution 28 g of KOH in 312 ml of HOAc
  • a do-aldehyde mixture (2-propylheptanal and 2-propyl-4-methylhexanal in a weight ratio of 9 : 1 : 1 offset.
  • an air pressure of 14 bar was set in the autoclave.
  • the speed of the stirrer was increased to 1200 rpm.
  • the temperature in the autoclave rose to 50 0 C and was controlled by the air supply kept at this temperature.
  • the autoclave was cooled to room temperature and depressurized.
  • the crude product obtained was a C 10 -carboxylic acid mixture consisting of 2-propylheptanoic acid and 2-propyl-4-methylhexanoic acid in a weight ratio of 9: 1.
  • the crude acid was subjected to distillation in a continuous distillation apparatus for purification.
  • the purity of the C 10 carboxylic acid after distillation was 99% (weight ratio of 2-propylheptanoic acid to 2-propyl-4-methylhexanoic acid of 9: 1).
  • Triethylene glycol 500 g, supplier: BASF AG, Ludwigshafen
  • the mixture was then filtered through activated carbon and the solvent removed in vacuo (initially 100 0 C at 1 atm, then 1 h at 150 0 C, 1 mbar).
  • the purity of the thus obtained triethylene glycol di (2-propylheptanoate) -containing ester mixture was 98.5% based on ester content (determined by NMR spectroscopy), the residual acid number was 0.02 mg KOH / g (titration), the water content was 20 ppm (Karl Fischer titration).
  • plasticizer properties of the ester mixture from Example 2 are compared with those of a commercial plasticizer (triethylene glycol di- (2-ethylhexanoate), available as Solutia S-2075 from Solutia).
  • a commercial plasticizer triethylene glycol di- (2-ethylhexanoate
  • films are produced using commercially available PVB resins and their performance (mechanical and optical) properties are tested.
  • volatility of both plasticizers from the film samples is tested.
  • the vinyl alcohol and vinyl acetate content of the PVB resin is determined wet-chemically according to the standard method for the chemical analysis of polyvinyl butyral according to ASTM D 1396-92.
  • the average molecular weight of the PVB resin is determined by gel permeation chromatography.
  • the powdery PVB resin and the comparative plasticizer 3G8 or the plasticizer 3G10 according to the invention in a mixture with the additive Marlophen NP6 are each metered separately into an extruder in accordance with the mixture composition. Careful homogenization of the components at the beginning of the extrusion ensures consistent mechanical and optimal see the properties of the film.
  • the extrusion takes place at temperatures above 150 0 C through a slot die, wherein the film thickness is set to 0.8 mm.
  • the PVB film pattern obtained after leaving the extruder is wound between PE foils and cut into test pieces of 30 cm ⁇ 40 cm. The performance properties and the measuring methods used are shown in the following Table 3.
  • PVB film and standard film according to the invention have similar break and elongation at break and tear resistance data which meet the requirements for technical products.
  • Both PVB Foil samples show an identical cold resistance. Even at a temperature of - 70 0 C no brittleness break occurs. The measured value is well below that described in the literature brittle temperature for PVB film of -55 0 C.
  • a further parameter for describing the temperature flexibility properties is the temperature-dependent torsional stiffness. In the absence of the availability of a torsional stiffness tester, the measurements are carried out in accordance with DIN 53447 using a rheometer with a solid-state measuring system.
  • plasticizer volatility from PVB film requires the determination of the mass loss of the film body under thermal stress.
  • test films the migration tendency of the plasticizer according to DIN 53405 test specimens of the PVB standard film and the PVB film according to the invention (test films) in the drying cabinet within two glass panes with for fixing and load above and below fitting Tonkachel between two PE film pieces (contact films) identical geometric shape heated to 50 0 C.
  • the exit tendency of the plasticizers is monitored by decreasing the masses of the test films and increasing the masses of the contact films after 1, 2 and 5 days (see Table 4).
  • thermogravimetric analysis TGA
  • the film sample is first heated under N2 atmosphere from 30 to 200 0 C at a rate of 10 ° C / min, the sample mass is measured at short intervals. Apparently, no plasticizer leakage takes place in this rapid heating process. Therefore, both film samples are subjected at a constant temperature of 110 0 C over a period of 120 minutes a thermogravimetric analysis. This process is also used to determine plasticizer volatility from PVC films.
  • TGA thermogravimetric analysis

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des diesters d'alcanediols, en particulier d'oligoalkylèneglycols, avec des acides carboxyliques C9 et/ou C10. L'invention concerne également leur utilisation comme plastifiant pour des polyvinylacétales et des polysulfures, des compositions polymères qui contiennent ces diesters comme plastifiant, et un procédé de fabrication de ces diesters.
PCT/EP2008/050148 2007-01-08 2008-01-08 Plastifiant pour polyvinylacétales et polysulfures Ceased WO2008084046A1 (fr)

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EP07100226.5 2007-01-08

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009118261A1 (fr) * 2008-03-28 2009-10-01 Exxonmobil Chemical Patents Inc. Plastifiants esters de polyols et leur procédé de fabrication
EP2123448A4 (fr) * 2007-03-09 2011-04-27 Nippon Sheet Glass Co Ltd Matériau de vitre pour automobile, automobile, liquide de revêtement de traitement antibuée et article antibuée
US8420866B2 (en) 2008-12-30 2013-04-16 Basf Se Process for preparing ketones by reacting 1,1-disubstituted olefins with N2O
WO2012175255A3 (fr) * 2011-06-21 2013-05-10 Evonik Oxeno Gmbh Procédé de production d'acide 2-éthylheptanoïque
WO2018069072A1 (fr) * 2016-10-11 2018-04-19 Kuraray Europe Gmbh Films multicouches à base d'acétal de polyvinyle à teneur élevée en plastifiant
CN110546191A (zh) * 2017-11-10 2019-12-06 积水化学工业株式会社 树脂发泡体
CN113504333A (zh) * 2021-08-20 2021-10-15 上海烟草集团有限责任公司 检测纸质包装材料中有机物迁移量的方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0010718A1 (fr) * 1978-10-27 1980-05-14 Hoechst Aktiengesellschaft Feuille transparente en polyvinylbutyral et procédé pour sa fabrication
JPH028222A (ja) * 1988-06-27 1990-01-11 Adeka Argus Chem Co Ltd ポリサルファイド重合体用低温性可塑剤
WO1996022268A1 (fr) * 1995-01-18 1996-07-25 Exxon Chemical Patents Inc. Composes organiques et leurs procedes de production
WO2002102591A1 (fr) * 2001-06-19 2002-12-27 Ht Troplast Ag Feuille de pvb renfermant un plastifiant
WO2003057773A1 (fr) * 2002-01-10 2003-07-17 Clariant Gmbh Matiere nanocomposite pour la fabrication de feuilles a gradient d'indice de refraction

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0010718A1 (fr) * 1978-10-27 1980-05-14 Hoechst Aktiengesellschaft Feuille transparente en polyvinylbutyral et procédé pour sa fabrication
JPH028222A (ja) * 1988-06-27 1990-01-11 Adeka Argus Chem Co Ltd ポリサルファイド重合体用低温性可塑剤
WO1996022268A1 (fr) * 1995-01-18 1996-07-25 Exxon Chemical Patents Inc. Composes organiques et leurs procedes de production
WO2002102591A1 (fr) * 2001-06-19 2002-12-27 Ht Troplast Ag Feuille de pvb renfermant un plastifiant
WO2003057773A1 (fr) * 2002-01-10 2003-07-17 Clariant Gmbh Matiere nanocomposite pour la fabrication de feuilles a gradient d'indice de refraction

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 199008, Derwent World Patents Index; AN 1990-054944, XP002468611 *

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2123448A4 (fr) * 2007-03-09 2011-04-27 Nippon Sheet Glass Co Ltd Matériau de vitre pour automobile, automobile, liquide de revêtement de traitement antibuée et article antibuée
WO2009118261A1 (fr) * 2008-03-28 2009-10-01 Exxonmobil Chemical Patents Inc. Plastifiants esters de polyols et leur procédé de fabrication
US9546259B2 (en) 2008-03-28 2017-01-17 Exxonmobil Chemical Patents Inc. Polyol ester plasticizers and process of making the same
US8420866B2 (en) 2008-12-30 2013-04-16 Basf Se Process for preparing ketones by reacting 1,1-disubstituted olefins with N2O
WO2012175255A3 (fr) * 2011-06-21 2013-05-10 Evonik Oxeno Gmbh Procédé de production d'acide 2-éthylheptanoïque
WO2018069072A1 (fr) * 2016-10-11 2018-04-19 Kuraray Europe Gmbh Films multicouches à base d'acétal de polyvinyle à teneur élevée en plastifiant
CN109789684A (zh) * 2016-10-11 2019-05-21 可乐丽欧洲有限责任公司 具有高增塑剂含量的基于聚乙烯醇缩醛的多层膜
CN110546191A (zh) * 2017-11-10 2019-12-06 积水化学工业株式会社 树脂发泡体
US11499042B2 (en) 2017-11-10 2022-11-15 Sekisui Chemical Co., Ltd. Foamed resin object
CN113504333A (zh) * 2021-08-20 2021-10-15 上海烟草集团有限责任公司 检测纸质包装材料中有机物迁移量的方法
CN113504333B (zh) * 2021-08-20 2023-03-14 上海烟草集团有限责任公司 检测纸质包装材料中有机物迁移量的方法

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