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WO1993017072A1 - Utilisation d'ethers et/ou d'esters de di(hydroxyalkyle)sulfones comme produits auxiliaires pour la mise en ×uvre de matieres synthetiques thermoplastiques - Google Patents

Utilisation d'ethers et/ou d'esters de di(hydroxyalkyle)sulfones comme produits auxiliaires pour la mise en ×uvre de matieres synthetiques thermoplastiques Download PDF

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Publication number
WO1993017072A1
WO1993017072A1 PCT/EP1993/000383 EP9300383W WO9317072A1 WO 1993017072 A1 WO1993017072 A1 WO 1993017072A1 EP 9300383 W EP9300383 W EP 9300383W WO 9317072 A1 WO9317072 A1 WO 9317072A1
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Prior art keywords
esters
sulfones
ethers
hydroxyalkyl
use according
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Ceased
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PCT/EP1993/000383
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German (de)
English (en)
Inventor
Jörg-Dieter KLAMANN
Peter Daute
Dieter Krampitz
Andreas Lippmann
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of WO1993017072A1 publication Critical patent/WO1993017072A1/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
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/41—Compounds containing sulfur bound to oxygen

Definitions

  • the present invention relates to the use of ethers and / or esters of di (hydroxyalkyl) sulfones as processing aids for thermoplastics.
  • processing aids are necessary in order to promote the melting process and the formation of a homogeneous flowable mass and to facilitate the flow of the melt by reducing the internal friction. This can be achieved by adding lubricants, which are added to the plastic before the shaping process.
  • lubricants which are added to the plastic before the shaping process.
  • mold release agents which, after their incorporation into the plastic, migrate from the plastic to the surface owing to their limited compatibility and thus reduce the adhesive.
  • the term “mold release agent” is used here and below synonymously for the term “external lubricant” which is particularly common in the PVC field.
  • an additive acts as a lubricant or mold release agent depends on many factors, such as its structure and the type of plastic, the slide effect and mold release effect coexisting in many cases.
  • metal soaps and fatty acid esters are used as lubricants for non-polar plastics such as polyethylenes and polypropylenes and fatty acid amides used.
  • Polar plastics such as polyesters, polycarbonates, polyamides, PVC.
  • Polystyrene and ABS usually need both lubricants and mold release agents.
  • Suitable mold release agents are fatty acid amides, metal soaps, polyethylene waxes, fatty acid esters or the mostly externally applied silicone oil.
  • Suitable lubricants for polar plastics classified according to chemical classes are listed in Ull ann's Ecyclopedia of Technical Chemistry, 4th revised and expanded edition, Volume 15, Verlag Chemie, Weinheim, 1978, pages 568-569 and in Gumbleter / Müller, Plastic Additives, 3rd ed., C. Hanser Verlag, 1990, pp. 443 - 505.
  • the mold release agents customary hitherto which are mainly important in the processing of thermoplastics by the injection molding process, have a disadvantage.
  • hot plastic melts are pressed into a metal mold in which they cool until they can be ejected with little pressure.
  • a long cooling phase had to be accepted with the mold release agents previously used.
  • the mold release agents only fully developed their release effect at low demolding temperatures. From an economic point of view, mold release agents are therefore required that have a separating effect even at high temperatures and enable the ejection of molded parts with low ejector pressure.
  • the lubricants known from the prior art should also be improved in their formation of a homogeneous, flowable mass, so that even complicated structures made of thermoplastic plastics, especially of polyamides, polyolefins and polystyrene and copolymers (e.g. ABS, ASA) can be manufactured.
  • these processing aids should under no circumstances impair the color or the shape behavior of the plastic during processing of the plastic, and should not be volatile and thermally stable.
  • the object of the present invention was to provide processing aids which meet these requirements.
  • the term processing aid is defined as an agent which acts as a lubricant and / or mold release agent.
  • the requirements placed on the processing aids can be met by ethers and / or esters of di (hydroxyalkyl) sulfones.
  • the present invention relates to the use of ethers and / or esters of di (hydroxyalkyl) sulfones of the general formula (I)
  • R *, R ⁇ can be the same or different and
  • X, Y may be the same or different and represent an alkylene radical having 1 to 50 carbon atoms
  • R7, R8 may be the same or different and
  • Hydrogen and / or a methyl radical mean p, q is 0 or a number in the range from 1 to 25 as processing aids for thermoplastics.
  • Ethers and esters of di (hydroxyalkyl) sulfones and sulfoxides are known compounds.
  • the mono- and / or diesters of thiodiglycol sulfones are particularly suitable, if necessary in a mixture with solvents, dispersing aids, emulsifiers and / or stabilizers, and a soft, dry textile fabric To give a grip.
  • ethers and / or esters of di (hydroxyalkyl) sulfones used in the context of the invention are of the etherification or esterification or ring opening methods known per se accessible from ⁇ -olefin epoxide compounds.
  • the sulfides of the general structure (II) on which the sulfones are based are expediently
  • Suitable di (hydroxyalkyl) sulfides that are oxidized to the sulfones are, for example, di (hydroxyoctyl) sulfide, di (hydroxyhexyl) sulfide, di (hydroxypentyl) sulfide, di (hydroxyisopropyl) sulfide, di (hydroxyisobutyl) sulfide and especially the commercially available thiodiglycol. Accordingly, in the context of the invention, preference is given to using ethers and / or esters of sulfones of the general formula I in which X and Y represent a straight-chain and / or branched, aliphatic alkylene group and in particular a methylene group.
  • ethers and / or esters of sulfones of the general formula I are used, in which p and q are equal to zero, that is to say they have no ethylene and / or propylene oxide units.
  • the sulfides described above are reacted with alkanols with 6 to 50 C atoms or ⁇ -olefin epoxy compounds with 6 to 30 C atoms, preferably with 8 to 22 C atoms.
  • sulfones of the general formula (I) are formed under ring opening, in which R 1 and / or R 4 denotes a ⁇ -hydroxy-substituted alkyl radical.
  • This ring opening generally takes place in a manner known per se in the presence of an acidic catalyst, such as sulfonic acids and mineral acids, or in the presence of a basic catalyst, such as alkali hydroxide and / or alkali methoxylate, the catalyst in amounts of 0.01 to 5 % By weight, based on the reaction mixture, is present. More detailed information on this reaction procedure can also be found in German Offenlegungsschriften DE-A-3936862 and DE-A-4038608.
  • Preferred alkanols are those having 8 to 22 carbon atoms, such as caprylic, pelargon, capric, lauryl, myristyl, palmityl, stearyl, linoleic, linolenic and / or behenyl alcohol.
  • the etherification expediently takes place in the presence of acidic catalysts such as sulfonic acids or mineral acids, which are present in amounts of 0.01 to 5% by weight, based on the reaction mixture.
  • the etherification is advantageously carried out at temperatures in the range from 120 to 240 ° C. with constant removal of water of reaction formed.
  • R * and / or R ⁇ can also mean a saturated and / or unsaturated acyl radical having 6 to 50 C atoms, preferably having 8 to 22 C atoms.
  • monocarboxylic acids and / or carboxylic acid derivatives such as anhydrides, acid chlorides and / or esters of short-chain alcohols having 1 to 4 carbon atoms, are esterified under customary esterification conditions, for example according to Ullmann's Encyclopedia of Industrial Chemistry, Vol. 11, 4. revised edition, Verlag Chemie, Weinheim, 1976, pages 91-93.
  • the reactants are reacted with one another in the presence of esterification catalysts such as tin compounds or tin grinding at temperatures of 160 to 260 ° C. with elimination of fiber. If desired, it can be wet be distilled off azeotropically, for which purpose it is necessary to add an organic solvent which forms an azeotrope with water.
  • esterification catalysts such as tin compounds or tin grinding at temperatures of 160 to 260 ° C. with elimination of fiber.
  • it can be wet be distilled off azeotropically, for which purpose it is necessary to add an organic solvent which forms an azeotrope with water.
  • Suitable monocarboxylic acids from which R 1 and R ⁇ are derived are aliphatic saturated and / or unsaturated monocarboxylic acids such as caproic acid, caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, arachidic acid, behenic acid, eurucic acid, Lignoceric acid, cerotic acid and melissic acid and mixtures of these acids as can be obtained from natural fats and oils.
  • monocarboxylic acids from which R 1 and R ⁇ are derived are aliphatic saturated and / or unsaturated monocarboxylic acids such as caproic acid, caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, arachidic acid, behenic acid, eurucic acid, Lignoceric acid, cerotic acid and melis
  • monocarboxylic acids are montanic acids and carboxylic acids, which are obtainable by oxidation of high-molecular alcohols such as the UNILIN R alcohols from the Petrolite Specialty Polymers Group.
  • branched carboxylic acids which are accessible by oxidation of the ⁇ -branched primary alcohols obtained by the Guerbet process.
  • Examples of these ⁇ -branched carboxylic acids are 2-n-butyl-n-octanoic acid, 2-n-heptyl-n-undecanoic acid, 2-n-octyl-n-dodecanoic acid, 2-n-dodecyl-n-he- xadecanoic acid and 2-n-hexadecyl-n-eicosanoic acid.
  • R.sup.1 and R.sup.1 signify an optionally ⁇ -hydroxy-substituted alkyl radical with 8 to 22 carbon atoms and / or an acyl radical with 8 to 22 carbon atoms.
  • R 1 or R ⁇ hydrogen
  • sulfones of the general formula I in which R and R 2 are an acyl radical are very particularly preferably used, and these are preferably derived from saturated and / or unsaturated, preferably saturated fatty acids having 8 to 22 carbon atoms, preferably with 12 to 22 carbon atoms and in particular of lauric, myristic, palitic, stearic and / or behenic acid.
  • etherified or esterified sulfones can be obtained if at least equimolar amounts of hydroxyl groups, for example the thiodiglycol, to monocarboxylic acids, alkanols and / or - olefin epoxide are set, preferably with a slight excess of 1 to 20 mol%, based on the molar amount on hydroxyl groups - worked.
  • alkoxylated ethers and / or esters of sulfones can also be used.
  • p and q in the general formula (I) denote a number in the range from 1 to 25, preferably 1 to 15, which may be a whole or broken number, which is the molar amount of alkoxide used corresponds.
  • alkoxylated ethers and / or esters are expediently prepared analogously to the non-alkoxylated sulfones.
  • alkoxylated sulfones which carry ethylene and / or propylene oxide units
  • alkoxylated alcohols ring-opened epoxides or carboxylic acids
  • alkoxylation products of the di (hydroxyalkyl) sulfides of the general structure (II) going out.
  • alkoxylated di (hydroxyalkyl) sulfides are preferably reacted with non-alkoxylated alcohols or olefin epoxides of the type described and then oxidized.
  • the carboxylic acids already described are preferably alkoxylated and then esterified with the di (hydroxyalkyl) sulfides of the general structure (II) before the oxidation takes place.
  • alkoxylation itself takes place under the usual conditions. Within the alkoxylated sulfones, exactly the same are preferred as for the non-alkoxylated ones.
  • the sulfones can be mixed with sulfoxides.
  • the Oxidation of sulfides depending on the reaction conditions, to mixtures of sulfides, sulfoxides and sulfones, which likewise belong to the scope of the present invention.
  • ethers and / or esters of sulfones which are not alkoxylated, that is to say those of the general formula (I) in which p and q are zero, are very particularly preferred.
  • the particularly suitable non-ethoxylated ethers and / or esters of the sulfones have already been listed.
  • esters and / or ethers of the sulfones are added to the thermoplastics to be processed in amounts of 0.01 to 10, preferably 0.05 to 5 and in particular 0.1 to 3 per hundred resins (phr) are added to the thermoplastics. They are expediently added to the melt obtained in the production of the thermoplastic or applied to the plastic granules or powder at elevated temperatures. For homogeneous mixing, it is advisable to extrude the ethers and / or esters of the sulfones with the thermoplastic plastic together at temperatures between 140 ° C.
  • ethers and / or esters of the sulfones can be added to all pure and modified thermoplastic plastics and their mixtures, be they polymers, polycondensates or polyaddition products. They are preferably suitable for processing polyamides, polyesters, polycarbonates, polystyrenes and copolymers, polypropylene and polyethylene and mixtures thereof.
  • thermoplastic materials can of course be modified, such as the impact-modified polypropylene modified with rubber, filled with fillers, stabilized or pigmented.
  • they are preferably used for thermoplastic materials which are shaped by means of extrusion, pressing, rolling, calendering, blow molding, foaming and injection molding, preferably by injection molding.
  • the esters and / or ethers of the sulfones show particularly good effects in polar plastics such as polyamide, polyester, polycarbonate, polystyrene and copolymers and mixtures thereof. The separating effect is then excellent with these plastics and, above all, is present even at high temperatures.
  • esters and / or ethers of the sulfones also act as lubricants, which ensures a smooth, rapid flow of the.
  • the plastic melt is reached.
  • they act as a lubricant in polyamide, polystyrene and copolymers of polypropylene and polyethylene, which makes it possible also to produce complex molded parts f.
  • esters and / or ethers of the sulfones are compatible with other lubricants, stabilizers, pigments and fillers, so that they can be added to the thermoplastic materials using known conventional additives.
  • Another object of the present invention is a method for improving the processing of thermoplastic materials, characterized in that the thermoplastic materials before they are processed. Processing ether and / or esters of di (hydroxyalkyl) sulfones of the general formula (I) can be added.
  • Another object of the present invention are molded parts based on thermoplastic materials, characterized in that they contain ethers and / or esters of di (hydroxyalkyl) sulfones of the general formula (I).
  • Esters of the sulfones with melting points below 80 ° C were applied to the plastic granules in the Henschel fluid mixer at approx. 80 ° C / 1000 min. Ester of the sulfones with melting points above 80 ° C were distributed by shaking in a polyethylene bag. The homogeneous incorporation of the sulfone esters into the plastic was carried out in a Collin twin-screw extruder (type 235, 50x15 D) at temperatures from 190 to 265 ° C. The homogeneous mass was cooled in an integrated water bath and pelletized using a round strand pelletizer. The granules were then dried. Table 1 shows the extrusion and drying conditions of the plastics with the incorporated esters of the sulfones. The amount is parts by weight which have been added to 100 parts by weight of thermoplastic.
  • the plastics are:
  • PA polyamide 66, unreinforced extrusion type (monofilament), low melt viscosity; Melt-volu e-index of 150 cm 3/10 min at 275 ° C / 5 kg; available as Ultramid R A 3 natural from BASF AG
  • PBT polybutylene terephthalate, unmodified, with a melt flow index of 34 g / 10 min at 250 ° C / 21.2 kg; Vicat softening temperature (DIN 53460) 180 ° C; available as Vestodur R 1000 from Hüls AG
  • PP polypropylene, completely stabilized, lubricant-free with a melt flow index of 5 g / 10 min at 230 ° C / 2.16 kg and a Vicat softening temperature of 148 ° C; available as Hostalen R PPT 1070 from Hoechst AG
  • PE polyethylene with a density of 0.923 g / cm 3 (DIN 53479) and a melt flow index of 2 to 3 g / 10 min (DIN 53735) at 190 ° C / 2.16 kg; Crystallite melting point 115 ° C (DTA); available as Flamul t R PEJ 06 natur from Herberts GmbH
  • ABS . Acrylonitrile-butadiene-styrene copolymer, gleitschok with ei ⁇ nem melt volume index of 2 cm 3/10 min. at 220 ° C / 10 kg and a Vicat softening temperature VST / B / 120 of 115 ° C; obtained as Novodur R P 3 T from Bayer AG
  • PC polycarbonate, medium-viscosity injection molding, release agent-free, with a density of 1.2 kg / cm 3 (DIN 53497) available as Xantar P 24 from DSM, the Netherlands
  • the release agent properties were determined using the Mannesmann Demag injection molding machine, model D-60 NC II, and a special demoulding tool (demoulding sleeve).
  • the oil pressure building up in the ejector system when the injection-molded sleeve was removed from the mold was evaluated as a measure of the separating action of the esters of the sulfones (registration of ejector pressure, core temperature during removal from the mold and metering time).
  • a mold was injected with the dimensions: mold 35 x 35 x 3.5 (top) / 2.0 (bottom) height x inner diameter x wall thickness, sprues
  • Nozzle temperature 270 ° C
  • Injection pressure 18 (approx. 420 bar)
  • Cooling time 15.0 s
  • Dosing delay time 0.5 s
  • Nozzle contact force 60 Mold clamping force: 500 kN mold temperature: gate side: water-cooled (9 1 / min) core: 80, 100 and 120 ° C at the time of demolding
  • the flow behavior was determined in the Mannes ann-Demag D 120 NC injection molding machine and the spiral shape.
  • the length of the sprayed spirals was used as a measure of the lubricant effect.
  • the following were selected as injection molding parameters:
  • Nozzle temperature 290 ° C
  • Screw speed 8-16 (position)
  • Injection pressure 12 (approx. 310 bar)
  • Cooling time 15.0 s
  • Dosing delay time 0.5 s
  • Time-dependent back nozzle 0.5 s
  • Nozzle contact force 11 Form clamping force: 1000 kN Tool: spiral, 3 x 15 mm, deflected at right angles, rod gate
  • the sulfone esters according to the invention are outstandingly suitable for polyamides; they are particularly characterized by the low demoulding pressures at all temperatures.
  • Nozzle temperature 230 ° C
  • Cooling time 15.0 s
  • Dosing delay time 0.5 s
  • Time-dependent back nozzle 0.5 s
  • Table 3 summarizes the spiral lengths. As a comparison 2, a mixture of 0.75 g of N, N-ethylene bisstearamide and 0.75 g of calcium stearate in PP was tested under the same conditions.
  • the flow behavior was determined as described. The following were selected as injection molding parameters:
  • Nozzle temperature 210 ° C
  • Cooling time 15.0 s
  • Dosing delay time 0.5 s
  • Delay time nozzle back 2.0 s
  • Time-dependent back nozzle 0.5 s
  • the flow behavior was determined in the Mannesmann Demag D 120 NC injection molding machine and the spiral shape.
  • the length of the sprayed spirals was used as a measure of the lubricant effect.
  • the following were selected as injection molding parameters:
  • Nozzle temperature 250 ° C
  • Cooling time 20.0 s
  • Dosing delay time 0.5 s
  • Time-dependent back nozzle 0.5 s
  • Table 5 summarizes the spiral lengths. As comparison 4, calcium stearate was tested under the same conditions.
  • release agent test was carried out as already described. The following were selected as injection molding parameters:
  • Time-dependent back nozzle 0.5 s
  • Molding temperature gate side: water-cooled (8 1 / min)
  • the sulfone esters according to the invention are outstandingly suitable for polycarbonates, since they ensure low demolding pressures over the entire temperature range. Release agent test on PBT (example H)
  • release agent test was carried out as already described. The following were selected as injection molding parameters:

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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 l'utilisation d'éthers et/ou d'esters de di(hydroxyalkyle) sulfones, qui sont éventuellement alcoxylés, comme produits auxiliaires pour la mise en oeuvre de matières synthétiques thermoplastiques. L'invention concerne en outre un procédé visant à assurer une meilleure mise en oeuvre des matières thermoplastiques, ainsi que les matières thermoplastiques qui contiennent les éthers et/ou les esters desdits sulfones.
PCT/EP1993/000383 1992-02-25 1993-02-17 Utilisation d'ethers et/ou d'esters de di(hydroxyalkyle)sulfones comme produits auxiliaires pour la mise en ×uvre de matieres synthetiques thermoplastiques Ceased WO1993017072A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4205700.0 1992-02-25
DE19924205700 DE4205700A1 (de) 1992-02-25 1992-02-25 Verwendung von ethern und/oder estern von di (hydroxyalkyl)sulfonen als verarbeitungshilfsmittel fuer thermoplastische kunststoffe

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Publication Number Publication Date
WO1993017072A1 true WO1993017072A1 (fr) 1993-09-02

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PCT/EP1993/000383 Ceased WO1993017072A1 (fr) 1992-02-25 1993-02-17 Utilisation d'ethers et/ou d'esters de di(hydroxyalkyle)sulfones comme produits auxiliaires pour la mise en ×uvre de matieres synthetiques thermoplastiques

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DE (1) DE4205700A1 (fr)
WO (1) WO1993017072A1 (fr)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4041003A (en) * 1975-02-18 1977-08-09 Bayer Aktiengesellschaft Process for molding aromatic polycarbonates having perfluoroalkanesulphonic acid derivatives as mold release agents

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4041003A (en) * 1975-02-18 1977-08-09 Bayer Aktiengesellschaft Process for molding aromatic polycarbonates having perfluoroalkanesulphonic acid derivatives as mold release agents

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DE4205700A1 (de) 1993-08-26

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