EP2283057A1 - Mélanges de copolymères d'organopolysiloxanes - Google Patents

Mélanges de copolymères d'organopolysiloxanes

Info

Publication number
EP2283057A1
EP2283057A1 EP09757403A EP09757403A EP2283057A1 EP 2283057 A1 EP2283057 A1 EP 2283057A1 EP 09757403 A EP09757403 A EP 09757403A EP 09757403 A EP09757403 A EP 09757403A EP 2283057 A1 EP2283057 A1 EP 2283057A1
Authority
EP
European Patent Office
Prior art keywords
carbon atoms
groups
radical
fluorine
optionally substituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP09757403A
Other languages
German (de)
English (en)
Inventor
Oliver SCHÄFER
Ernst Selbertinger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wacker Chemie AG
Original Assignee
Wacker Chemie AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Wacker Chemie AG filed Critical Wacker Chemie AG
Publication of EP2283057A1 publication Critical patent/EP2283057A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/61—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step

Definitions

  • the invention relates to transparent mixtures containing organopolysiloxane copolymers and their use.
  • Organic thermoplastics are characterized by their excellent mechanical strength, elasticity and ease of processing by extrusion from the melt.
  • Silicone elastomers have excellent transparency as well as temperature, UV and weathering stability. They maintain their elastic properties at lower temperatures and therefore do not tend to embrittle. In addition, they have special water-repellent and non-stick surface properties.
  • HTV high temperature vulcanizing systems
  • RTV room temperature vulcanizing systems
  • Curing is usually carried out by peroxidic crosslinking, by hydrosilylation by means of platinum catalysis or, for example, by condensation reactions.
  • 2K systems have very long pot lives, but to achieve optimum properties, the mixing ratios of both components must be strictly adhered to, which leads to an increased equipment complexity in processing.
  • 1K systems also cure by peroxide crosslinking, by hydrosilylation by platinum catalysis, or by condensation reactions, for example.
  • either an additional processing step is required for compounding the crosslinking catalyst or the masses have only a limited pot life.
  • all these systems have in common that the products are insoluble after processing and, for example, can no longer be recycled.
  • thermoplastic elastomers and silicone polymers should make materials with good mechanical properties accessible, which at the same time are greatly simplified compared to silicones
  • the object of the invention is to improve the state of the art, in particular to provide polymers which are transparent and have thermal and optical stability.
  • the invention relates to compositions containing between 50 and 99, 999% of a
  • R is a monovalent, optionally substituted by fluorine or chlorine hydrocarbon radical having 1 to 20 carbon atoms
  • X is an alkylene radical having 1 to 20 carbon atoms in which non-adjacent methylene units are represented by groups
  • A is an oxygen atom or an amino group -NR '-
  • Z is an oxygen atom or an amino group -NR' -
  • R ' is hydrogen or an alkyl radical having 1 to 10
  • Y is a bivalent, optionally substituted by fluorine or chlorine hydrocarbon radical having 1 to 20 carbon atoms,
  • D is an optionally substituted by fluorine, chlorine, C 1 -C 6 alkyl or C 1 -C 6 alkyl substituted alkylene radical having 1 to 700
  • Carbon atoms in which non-adjacent methylene units may be replaced by groups -O-, -COO-, -OCO-, or -OCOO-,
  • B is hydrogen or a functional or non-functional organic or organosilicon radical
  • n is a number from 1 to 1000
  • a is a number of at least 1
  • b is a number from 0 to 40
  • c is a number from 0 to 30
  • d is a number greater than 0.
  • R is a monovalent, hydrocarbon radical having 1 to 6 carbon atoms, in particular unsubstituted.
  • Particularly preferred radicals R are methyl, ethyl, vinyl and phenyl.
  • X is an alkylene radical having 1 to 10 carbon atoms.
  • the alkylene radical X is not interrupted.
  • A is an NH group.
  • Z is preferably an oxygen atom or an NH group
  • Y is a hydrocarbon radical having 3 to 14 carbon atoms, which is preferably unsubstituted.
  • Y is an aralkylene, linear or cyclic alkylene radical.
  • Y is a saturated Alyklyen residue.
  • D is an alkylene radical having at least 2, in particular at least 4 carbon atoms and at most 12 carbon atoms.
  • D is a polyoxyalkylene radical, in particular polyoxyethylene radical or polyoxypropylene radical having at least 20, in particular at least 100 carbon atoms and at most 800, in particular at most 200 carbon atoms.
  • radical D is not substituted.
  • n is preferably a number of at least 3, in particular at least 25 and preferably at most 140, in particular at most 100, particularly preferably at most 60.
  • a is a number of at most 50.
  • b is preferably a number of at most 50, especially at most 25.
  • c is preferably a number of at most 10, in particular at most 5.
  • Solid powdered stabilizers dissolve in contrast to organic polymers in the Organopolysiloxane / polyurea / polyurethane block copolymers not and thus lead to scattering centers that reduce the transparency.
  • the transmission when using the UV absorbers according to the invention in the wavelength range 400 nm to 430 nm, the transmission, with a layer thickness of 0.5 mm, greater than 85%.
  • the absorption is> 80%.
  • UV absorbers are preferably 4-hydroxybenzoates, benzophenones, such as 2-hydroxybenzophenones, benzotriazoles, such as preferably 2-hydroxyphenylbezotriazoles or triazine compounds.
  • UV absorbers examples include UV absorbers.
  • thermal stabilizers hindered amines and phosphorus compounds are preferably used. Examples are
  • a UV stabilizer is additionally included.
  • the UV stabilizer is preferably hindered amines, so-called HALS stabilizers. Examples are:
  • a combination of UV-absorbers and light stabilizer is preferably used, alone or together with further stabilizers are optionally liquid at temperatures below 50 0 C. This may also happen ducrh the formation of a common eutectic mixture.
  • the UV absorber is present in a higher concentration than the light stabilizer in the system. Most preferably, the UV absorber is used in an at least double concentration as the light stabilizer.
  • the concentration of free amino groups or isocyanate groups in the polymer (I) is preferably less than 40 mmol / kg, more preferably less than 15 mmol / kg and most preferably less than 10 mmol / kg.
  • Outdoor weathering is transparent and colorless.
  • the degree of yellowing can be specified by specifying a so-called deltaY or Yellowness value.
  • Humidity is less than 10, more preferably less than 5.
  • the yellowness index is determined according to ASTM E313.
  • the polydiorganosiloxane-urea copolymer of the general formula (1) shows high molecular weights and good mechanical properties with good processing properties.
  • the Processing properties are defined, inter alia, by the so-called MVR value, which is determined in accordance with DIN EN 1133. This value indicates the volume of a polymer which is pressed through a nozzle within 10 minutes at a given coating weight and given temperature. This value indicates the flowability of a polymer under defined conditions.
  • composition according to the invention preferably has an MVR value between 1 and 400 ml / 10 min (measured at 180 ° C.,
  • 21.6 kg load weight particularly preferably an MVR value between 5 and 200 ml / 10 min (measured at 180 ° C., 21.6 kg load weight), very particularly preferably an MVR value between 15 and 120 ml / 10 min (measured at 180 ° C., 21.6 kg load weight).
  • chain extenders such as dihydroxy compounds or water in addition to the urea groups
  • the chain extenders used have the general formula (6)
  • the copolymer of the general formula (1) based on the sum of the urethane and urea groups, at least 50 mol%, in particular at least 75 mol% of urea groups.
  • copolymer of the general formula (1) based on the sum of the urethane and urea groups, preference is given to containing at least 50% by weight, in particular at least 75% by weight, of polydiorganosiloxanes.
  • the functional polydialkysiloxanes used to prepare the compounds of the present invention can be prepared according to the state of the art, with special emphasis on the specific preparation of difunctional compounds, e.g. in EP 250248 or in DE 10137855, emphasis is placed.
  • diisocyanates to be used of the general formula (5) include aliphatic compounds such as isophorone diisocyanate, 6-diisocyanate, hexamethylene-1, tetramethylene 1, 4-diisocyanate, and methylenedicyclohexyl-4, 4 ⁇ - diisocyanate, or aromatic compounds such as methylenediphenyl 4, 4 ⁇ - diisocyanate, 2, 4-toluene diisocyanate, 2, 5-toluene diisocyanate, 2, 6-toluene diisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, m-xylene diisocyanate, tetramethyl-m-xylene diisocyanate or mixtures of these isocyanates.
  • aliphatic compounds such as isophorone diisocyanate, 6-diisocyanate, hexamethylene-1, tetramethylene 1, 4-di
  • Examples of commercially available compounds are the diisocyanates of the DESMODUR® series (H, I, M, T, W) of Bayer AG, Germany. Preference is given to aliphatic diisocyanates in which Y is an alkylene radical which carry these materials, which show improved UV stabilities, which is advantageous in an outdoor application of the polymers.
  • the ⁇ , ⁇ -OH-terminated alkylenes of the general formula (6) are preferably polyalkylenes or polyoxyalkylenes. These are preferably largely free of contaminants from mono-, tri- or higher-functional polyoxyalkylenes.
  • polyether polyols, polytetramethylene diols, polyester polyols, polycaprolactone diols but also ⁇ , ⁇ -OH-terminated polyalkylenes based on polyvinyl acetate,
  • Polyvinylacetatethylencopolymere polyvinyl chloride copolymer, polyisobutlydiols are used. Preference is given here polyoxyalkyls are used, more preferably polypropylene glycols. Such compounds are as
  • Base materials for flexible polyurethane foams and for coating applications commercially available with molecular masses Mn up to more than 10,000.
  • examples of these are the BAYCOLL® polyether polyols and polyester polyols from Bayer AG, Germany or the Acclaim® polyether polyols from Lyondell Inc., USA. It is also possible to use monomeric .alpha.,. Omega.-alkylenediols, such as ethylene glycol, propanediol, butanediol or hexanediol.
  • dihydroxy compounds are also to be understood as meaning bishydroxyalkyl silicones, as described, for example, in US Pat. sold by the company Goldschmidt under the name Tegomer H-Si 2111, 2311 and 2711.
  • monoisocyanate compounds or monoamine compounds such as dodecylamine or preferably monofunctional polydiorganosiloxanes are added as additional additives, the addition of this monofunctional siloxane component preferably being added at defined levels to thereby ensure control of the rheological properties of the composition. It is also possible to use relatively unreactive components, such as carbinol functional compounds, which last react because of their tendency to react and thus form the end group of the polymers.
  • Another aspect of the invention is a process for the preparation of polymers from a composition according to the invention wherein the polymer is first granulated and then melted for further processing, wherein the UV absorber and optionally the UV stabilizer are mixed in.
  • Another object of the invention is a process for the preparation of polymers from a novel
  • composition wherein the polymer in its preparation already the UV absorber and optionally the UV stabilizer are admixed.
  • the preparation of the above-described copolymers of the general formula (1) can be carried out both in solution and in solid substance, continuously or discontinuously. It is essential that for the selected polymer mixture under the reaction conditions, an optimal and homogeneous mixing of the components takes place and a
  • Phase incompatibility is optionally prevented by solubilizers.
  • the preparation depends on the solvent used. If the proportion of hard segments such as urethane or urea units is large, it may be necessary to choose a solvent having a high solubility parameter such as dimethylacetamide. For most syntheses, THF has proven to be sufficiently well suited.
  • all ingredients are dissolved in an inert solvent. Particularly preferred is a synthesis without solvent. For the reaction without solvent, the homogenization of the mixture is of crucial importance in the reaction. Furthermore, the polymerization can also be controlled by the choice of the reaction sequence in a step synthesis.
  • the reaction preferably takes place, as usual in the preparation of polyurethanes, by adding a catalyst.
  • Suitable catalysts for the preparation are dialkyltin compounds, such as, for example, dibutyltin dilaurate, dibutyltin diacetate, or tertiary amines, such as, for example, N, N-
  • the mixtures according to the invention can be obtained in several ways.
  • the mixture of the stabilizers according to the invention to the already fully polymerized organopolysiloxane / polyurea / polyurethane block copolymer may be present either as a solid or granules or as a polymer melt. This mixture can be re-heated by e.g. be homogenized in a heated kneader.
  • Another preferred option is the addition of the stabilizers according to the invention to one of the educts which are used for the preparation of the
  • Organopolysiloxane / polyurea / polyurethane block copolymers can be used.
  • the addition is particularly preferably carried out in the silicone component.
  • the stabilizers are then distributed homogeneously in the end product.
  • Another object of the invention are films, films or moldings, wherein they have polymers of the invention.
  • Another object of the invention is a process for the encapsulation of solar cells, wherein polymers of the invention are used.
  • Tinuvin P phenol, 2- (2H-benzotriazole-2-yl) -4-methyl, Ciba
  • Tinuvin 765 bis (1, 2, 2, 6, 6-pentamethyl-4-piperidyl) sebacate
  • Irganox 1135 3, 5-di-tert-butyl-4-hydroxyhydrocinnamic acid, C7-9-branched alkyl ester, Ciba SC, liquid
  • Stabilizer mixture B75 (mixture of Irganox 1135, Tinuvin
  • the diisocyanate was metered in a nitrogen atmosphere in the first heating zone and the aminopropyl-terminated silicone oil in the second heating zone.
  • the temperature profile of the heating zones was programmed as follows: Zone 1 30 0 C, Zone 2 140 0 C, Zone 3 160 ° C, Zone 4 185 ° C, Zone 5 185 0 C, Zone 6 180 0 C.
  • the speed was 150 u / min.
  • the diisocyanate (methylenebis (4-isocyanatocyclohexane)) was metered into zone 1 at 1320 mg / min and the amine oil (2900 g / mol) was metered into zone 2 at 15 g / min.
  • the nozzle of the extruder could a
  • Polydimethylsiloxane-polyurea block copolymer having a molecular weight of 84,200 g / mol and an MVR value (21.6 kg, 180 ° C) of 63, which was subsequently granulated.
  • the polymer from Example 2 was mixed with various amounts of the stabilizer mixture B75 from Ciba SC (100 ppm, 250 ppm, 500 ppm) and then compounded in a 2-shaft kneader.
  • the homogeneous mixture thus obtained was after cooling and granulation in a Suntester the Fa. Altlas irradiated (750 W / m2). After various times samples were taken and their weight average molecular weight determined
  • optical properties of the material were also determined:
  • Stabilizer concentration and stabilizer combination significantly more UV-stable materials can be obtained.
  • the polymer from Example 1 was mixed in a bucket with various amounts of the stabilizer mixture B75 from Ciba SC (1000 ppm, 2500 ppm, 5000 ppm) and then compounded in a 2-shaft kneader.
  • Stabilizer concentration and stabilizer combination can obtain highly UV-stable materials.
  • the temperature profile of the heating zones was programmed as follows: Zone 1 30 0 C, Zone 2 140 0 C, Zone 3 160 ° C, Zone 4 185 ° C, Zone 5 185 0 C, Zone 6 180 0 C.
  • the speed was 150 u / min.
  • the diisocyanate methylene bis (4-isocyanatocyclohexane)
  • a polydimethylsiloxane polyurea block copolymer was obtained with a molecular weight of 88,300 g / mol and a MVR value (21.6 kg 180 0 C) of 57 to the nozzle of the extruder, which was subsequently granulated.
  • the polymer from example 5 was irradiated in a Suntester from the company Atlas (750 W / m 2 ). After 1000 h, samples were taken and their weight average molecular weight determined.
  • Stabilizer concentration and stabilizer combination can obtain highly UV-stable materials by adding a stabilizer in a starting material of the polyaddition.
  • the diisocyanate was metered in a nitrogen atmosphere in the first heating zone and the aminopropyl-terminated silicone oil (FLUID NH 40 D) in the second heating zone.
  • the temperature profile of the heating zones was programmed as follows: Zone 1 30 0 C, Zone 2 140 0 C, Zone 3 160 ° C, Zone 4 185 ° C, Zone 5 185 0C, Zone 6 180 0 C.
  • the speed was 150 u / minute
  • the speed was 150 u / minute.
  • Diisocyanate methylene bis (4-isocyanatocyclohexane)
  • the amine oil fluid NH 40 D, 2900 g / mol
  • a polydimethylsiloxane polyurea block copolymer could be obtained (21.6 kg 180 0 C) of 88 to the nozzle of the extruder having a molecular weight of 65200 g / mol and a MVR value, which was then granulated.
  • the polymer from Example 8 was added to a bucket with various amounts of the stabilizer mixture Tinuvin 571 (UV absorber) and Tinuvin 765 (UV stabilizer) from. Ciba SC and then compounded in a 2 wave kneader, the thus obtained homogeneous mixture was after Cooling and granulation were irradiated in a Suntester from the company Atlas (750 W / m 2 ). After 200 hours, samples were taken and their weight average molecular weight determined.
  • UV absorber UV absorber
  • Tinuvin 765 UV stabilizer
  • UV absorber should be used in a higher concentration than the UV stabilizer.
  • the diisocyanate was heated under a nitrogen atmosphere in the first heating zone and the aminopropyl-terminated (fluid NH 40 D) silicone oil (bisaminopropyl-terminated PDMS having a molecular weight of 2900 g / mol; BAPS) in the second heating zone. dosed.
  • Various amounts of stabilizer Tinuvin 571, Tinuvin 765 and Irganox 1135 were mixed into the aminoproyl-terminated silicone oil (FLUID NH 40 D) and optionally a monofunctional aminopropyl-terminated PDMS (MAPS) having a molecular weight of 980 g / mol.
  • the temperature profile of the heating zones was programmed as follows: Zone 1 30 0 C, Zone 2 140 0 C, Zone 3 160 ° C, Zone 4 185 ° C, Zone 5 185 0 C, Zone 6 180 0C.
  • the speed was 150 rpm.
  • the diisocyanate (methylenebis (4-isocyanatocyclohexane)) (H12MDI) was metered into zone 1 at 1320 mg / min and the amine oil component was metered into zone 2 at 15 g / min.
  • H12MDI methylenebis (4-isocyanatocyclohexane)
  • a polydimethylsiloxane polyurea block copolymer could be obtained, which was then granulated. All materials were colorless, highly transparent polymers.
  • the individual polymers were subjected to a molecular weight determination, the content of free amino groups determined by NMR and then at 85 0 C and 85% rel. Humidity stored for 6 weeks in a climate chamber.
  • Example 10 (Production by Blend Method) The polymer from Example 2 was mixed with various amounts of the solid Tinuvin P from Ciba SC (100 ppm, 250 ppm, 500 ppm) and then compounded in a 2-shaft kneader.

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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)
  • Polyurethanes Or Polyureas (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention se rapporte à des compositions contenant entre 50 et 99,999 % d'un copolymère à blocs organopolysiloxane/polyurée/polyuréthane de formule générale (1) contenant entre 0,001 % et 10 % d'un absorbeur d'UV et pouvant être compatibles avec le polymère de formule générale I, la concentration de groupes isocyanate ou de groupes amine libres dans le polymère (I) étant inférieure à 40 mmoles/kg; R désignant un radical hydrocarboné monovalent ayant 1 à 20 atomes de carbone et substitué le cas échéant par un atome de fluor ou de chlore; X désignant un radical alkyle ayant 1 à 20 atomes de carbone dans lequel on peut remplacer des motifs méthylène non adjacents par des groupes -O-; A désignant un atome d'oxygène ou un groupe amine -NR'-; Z désignant un atome d'oxygène ou un groupe amine -NR'-; R' désignant l'hydrogène ou un radical alkyle ayant 1 à 10 atomes de carbone; Y désignant un radical hydrocarboné divalent ayant 1 à 20 atomes de carbone et substitué le cas échéant par un atome de fluor ou de chlore; D désignant un radical alkyle ayant 1 à 700 atomes de carbone, substitué le cas échéant par un atome de fluor, de chlore, un groupe alkyle en C1-C6 ouun ester d'alkyle enC1-C6 et dans lequel on peut remplacer les motifs méthylène non adjacents par des groupes -O-, -COO-, -OCO- ou -OCOO-; B désignant l'hydrogène ou un radical organique ou organosilicique fonctionnel ou non fonctionnel; n désignant un nombre de 1 à 1000; a désignant un nombre d'au moins 1; b désignant un nombre de 0 à 40,15; c désignant un nombre de 0 à 30; et d désignant un nombre supérieur à 0.
EP09757403A 2008-05-29 2009-05-25 Mélanges de copolymères d'organopolysiloxanes Withdrawn EP2283057A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102008002075A DE102008002075A1 (de) 2008-05-29 2008-05-29 Mischungen von Organopolysiloxan-Copolymeren
PCT/EP2009/056299 WO2009147020A1 (fr) 2008-05-29 2009-05-25 Mélanges de copolymères d’organopolysiloxanes

Publications (1)

Publication Number Publication Date
EP2283057A1 true EP2283057A1 (fr) 2011-02-16

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EP09757403A Withdrawn EP2283057A1 (fr) 2008-05-29 2009-05-25 Mélanges de copolymères d'organopolysiloxanes

Country Status (10)

Country Link
US (1) US20110076795A1 (fr)
EP (1) EP2283057A1 (fr)
JP (1) JP2011522076A (fr)
KR (1) KR20110008291A (fr)
CN (1) CN102046687A (fr)
AU (1) AU2009254100B2 (fr)
BR (1) BRPI0912298A2 (fr)
DE (1) DE102008002075A1 (fr)
MX (1) MX2010012973A (fr)
WO (1) WO2009147020A1 (fr)

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MX2010012973A (es) 2011-01-21
BRPI0912298A2 (pt) 2015-10-20
DE102008002075A1 (de) 2009-12-03
AU2009254100A1 (en) 2009-12-10
US20110076795A1 (en) 2011-03-31
JP2011522076A (ja) 2011-07-28
WO2009147020A1 (fr) 2009-12-10
CN102046687A (zh) 2011-05-04
AU2009254100B2 (en) 2012-05-31
KR20110008291A (ko) 2011-01-26

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