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EP2150570A1 - Composés de polycarbonate et/ou de polyuréthanne-polyorganosiloxane - Google Patents

Composés de polycarbonate et/ou de polyuréthanne-polyorganosiloxane

Info

Publication number
EP2150570A1
EP2150570A1 EP08759862A EP08759862A EP2150570A1 EP 2150570 A1 EP2150570 A1 EP 2150570A1 EP 08759862 A EP08759862 A EP 08759862A EP 08759862 A EP08759862 A EP 08759862A EP 2150570 A1 EP2150570 A1 EP 2150570A1
Authority
EP
European Patent Office
Prior art keywords
polycarbonate
defined above
polyurethane
polyorganosiloxane
formula
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Withdrawn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
EP08759862A
Other languages
German (de)
English (en)
Inventor
Walter Simon
Karl-Heinz Sockel
Gunnar Hoffmueller
Roland Wagner
Horst Lange
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.)
Henkel AG and Co KGaA
Original Assignee
Momentive Performance Materials GmbH
Momentive Performance Materials Inc
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 Momentive Performance Materials GmbH, Momentive Performance Materials Inc filed Critical Momentive Performance Materials GmbH
Publication of EP2150570A1 publication Critical patent/EP2150570A1/fr
Withdrawn legal-status Critical Current

Links

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
    • C08G71/00—Macromolecular compounds obtained by reactions forming a ureide or urethane link, otherwise, than from isocyanate radicals in the main chain of the macromolecule
    • C08G71/04—Polyurethanes
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/445—Block-or graft-polymers containing polysiloxane sequences containing polyester sequences
    • C08G77/448—Block-or graft-polymers containing polysiloxane sequences containing polyester sequences containing polycarbonate sequences
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/458—Block-or graft-polymers containing polysiloxane sequences containing polyurethane sequences
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/10—Block- or graft-copolymers containing polysiloxane sequences

Definitions

  • the invention relates to novel polycarbonate and / or polyurethane-polyorganosiloxane compounds, processes for their preparation, their use, precursors for their preparation and reactive compositions containing the precursors.
  • Quaternary ammonium structures containing siloxane block copolymers are widely known.
  • these may be diblock copolymers of the siloxane / quaternary ammonium unit type (DE 33 40 708, EP 282720, US 6240929, US 6730766).
  • triblock copolymers have been developed which are based on the combination siloxane / quaternary ammonium unit / polyether block (WO 02/10256, WO 02/10257, WO 02/10259, WO 2004/090007, WO 03/078504, WO 2004/041912, WO 2004 / 042136).
  • An essential advantage of these triblock copolymers is that their structure can be adapted flexibly and within very wide limits to the concrete product requirements.
  • the present invention provides new polycarbonate and / or polyurethane polyorganosiloxane compounds that can react specifically from stable precursors in the application to the desired polycarbonate and / or polyurethane polyorganosiloxane compounds.
  • the new polycarbonate and / or polyurethane-polyorganosiloxane compounds are easy, safe and targeted to manufacture and have new interesting properties.
  • the invention relates to novel polycarbonate and / or polyurethane-polyorganosiloxane compounds containing at least one structural element of the formula (1):
  • Y 1 and Y 2 are independently selected from -O-, -S- and -NR 2 -, wherein
  • R 2 hydrogen or a straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radical having up to 40 carbon atoms and having one or more groups selected from -O-, -C (O) -, -NH- and -NR 3 - may contain, wherein R 3 is as defined above, and
  • ST 1 and ST 2 are independently selected from bivalent to polyvalent, preferably tetravalent, straight-chain, cyclic or branched, saturated, unsaturated or aromatic, substituted or unsubstituted hydrocarbon radicals having up to 1000 carbon atoms and having one or more
  • R 3 is a straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radical having up to 40 carbon atoms and which may contain one or more groups selected from -O-, -C (O) - and -NH-, and
  • R 5 is a straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radical having up to 100 carbon atoms, which may contain one or more groups selected from -O-, -C (O) - and -NH-, or R 5 - A -
  • ST adjacent radicals Y 1 with ST 1 and / or one or both radicals Y 2 with ST 2 which may be adjacent to ST 1 can each form a nitrogen-containing heterocyclic radical
  • ST 5 is an optionally substituted, divalent, straight-chain, cyclic or branched, saturated or unsaturated hydrocarbon radical having 1 to 12 carbon atoms,
  • ST is an optionally substituted, divalent, straight-chain, cyclic or branched, saturated or unsaturated hydrocarbon radical having 1 to 12 carbon atoms,
  • radicals ST 1 and / or ST 2 comprises a polyorganosiloxane radical
  • acid addition compounds refers in particular to salt-like compounds which are obtained by protonation of basic groups in the molecule, such as in particular optionally present amino groups, for example by reaction with inorganic or organic acids. Salts of the compounds according to the invention result, in particular, from the formation of quaternary ammonium-containing compounds, in particular radicals
  • This variant also includes the case that the heterocyclic structure comprises only one radical Y such that -Y-ST-Y- has, for example, the following structure, i. Piperidine derivatives having:
  • Substituents of the hydrocarbon radicals for ST 1 and ST 2 include one or more, preferably one to three, substituents which are preferably selected from the group consisting of: hydroxy, halogen, such as fluorine or chlorine and cyano.
  • the polyorganosiloxane structural element which is obligatory in the polycarbonate and / or polyurethane-polyorganosiloxane compounds according to the invention preferably has the formula (2):
  • R i 4 is a straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radical having up to 20 carbon atoms, and
  • R i 4 Ci to C 2 0, preferably Ci to C9, straight-chain or cyclic or branched, saturated or unsaturated or aromatic hydrocarbon radical, more preferably methyl and phenyl and
  • s is preferably 1 to 199, especially 1 to 99.
  • the siloxane unit has the structure
  • ST and ST are each -CH 2 -, so that the formula (1) follows
  • both ST and ST are each divalent radicals, so that linear polycarbonate and / or polyurethane-polyorganosiloxane compounds are formed.
  • Such linear polycarbonate and / or polyurethane-polyorganosiloxane compounds of the invention are preferably used in those applications where good miscibility or dispersibility in aqueous media is needed. Such applications include, in particular, their use as softeners for fibers, particularly in laundry detergents, fabric care products, textile finishing agents, thermoplastic modifiers.
  • the invention also includes branched polycarbonate and / or polyurethane polyorganosiloxane compounds in which at least one of the radicals ST or ST is trivalent or polyvalent, preferably tetravalent, so that branched structures having linear repeating structures of structural elements of the formula (1) form ,
  • Such branched structural polycarbonate and / or polyurethane polyorganosiloxane compounds of the invention are particularly needed for those applications where thermosetting coatings or elastomers are made from the polycarbonate and / or polyurethane polyorganosiloxane compounds of the invention.
  • the polycarbonate and / or polyurethane-polyorganosiloxane compounds according to the invention preferably have on average preferably at least two, more preferably at least three structural elements of the formula (1).
  • polycarbonate and / or polyurethane-polyorganosiloxane compounds according to the invention have on average at least two, preferably at least three polyorganosiloxane structural elements of the formula (2).
  • the preferred polycarbonate and / or polyurethane polyorganosiloxane compounds according to the invention furthermore preferably have at least one, more preferably at least two, more preferably at least three repeat units of formula (3) on:
  • Y, Y, ST and ST are as defined above.
  • the number of repeating units of the formula (1) or (3) present in the polycarbonate- and / or polyurethane-polyorganosiloxane compounds according to the invention can be controlled within wide limits via the choice of the stoichiometry of the starting compounds in a manner known per se.
  • R 2 is preferably H, and the remaining variables are as defined above;
  • polycarbonate and / or polyurethane-polyorganosiloxane compounds in which Y is -NR -, where R is as defined above are preferably hydrogen.
  • Polyurethane-polyorganosiloxane compounds in which Y 1 and Y 2 are -NH- are particularly preferred according to the invention.
  • these amino groups are particularly preferred.
  • the presence of quaternary ammonium groups which serves in particular for the adjustment of hydrophilic properties, as they are particularly advantageous when used in aqueous compositions.
  • the amino groups may in particular also be terminal groups.
  • linear polycarbonate and / or polyurethane polyorganosiloxane compounds in which the radicals ST and ST are identical and are each dihydric.
  • radicals ST 1 and ST 2 may each be bivalent and the same and also the radicals Y 1 and Y 2 may be identical. Then, for example, the compound of the formula (7) results:
  • At least one radical ST must have a polyorganosiloxane group.
  • radicals ST and ST 2 in the polycarbonate and / or polyurethane-polyorganosiloxane compounds are different (ST ⁇ ST). This allows a greater flexibility of the property control via the selection of the residues ST 1 and ST 2 .
  • the polycarbonate and / or polyurethane-polyorganosiloxane compounds have at least one radical ST 1 of the following formula (9):
  • the polycarbonate and / or polyurethane-polyorganosiloxane compounds have at least one radical ST 2 a radical of the formula (10) with quaternary groups: -ST 3 -N + (R 5 ) 2 -ST 4 -N + (R 5 ) 2 -ST 3 - (10)
  • ST 3 is a straight-chain or cyclic or branched, saturated or unsaturated or aromatic, substituted or unsubstituted hydrocarbon radical having 2 to 100 carbon atoms, which may be substituted by -O-, -C (O) -, -NH-, -NR 3 - wherein R 3 is as defined above, and
  • ST 4 straight-chain or cyclic or branched, saturated or unsaturated or aromatic, substituted or unsubstituted hydrocarbon radical having 2 to 100 carbon atoms, represented by -O-, -C (O) -, -NH-, -NR 3 - and by a polyorganosiloxane unit with 2 to 200 silicon atoms may be substituted, wherein R 3 is as defined above.
  • Substituents of the hydrocarbon radicals for ST 3 and ST 4 include one or more, preferably one to three substituents, which are preferably selected from the group consisting of: hydroxy, halogen, such as fluorine or chlorine and cyano. Hydroxy is particularly preferred, especially for ST 4 .
  • polycarbonate and / or polyurethane-polyorganosiloxane compound of the following repeat units is a preferred embodiment of the invention:
  • ST 1 , ST 3 , ST 4 , R 2 and R 5 are as defined above, and A "is an organic or organic anion
  • the radicals ST 1 are structures which are derived directly from di- and higher-functional primary and secondary amines or alcohols.
  • divalent, cyclic hydrocarbon radicals having up to 15 carbon atoms for example based on bis-cyclohexylmethane structures
  • divalent, branched hydrocarbon radicals having up to 15 carbon atoms for example based on methylcyclohexyl or isophorone structures
  • divalent, aromatic hydrocarbon radicals having up to 15 carbon atoms, for example based on 2,4-toluyl, 2,6-toluyl, bis-phenylmethane and naphthylene structures
  • Example is N (CH 2 CH 2 NH 2 ) S.
  • polyamines or polyols which can contribute the radical ST include, for example, hexamethylenediamine, phenylenediamines, toluenediamines, cyclohexanediamine, ethylenediamine and oligomers thereof, trimethylolpropane, glycol, glycerol, pentaerythitol, sugars, or polyalkoxylated derivatives of the polyamine or polyols.
  • the hydrocarbon radicals ST 1 in another preferred embodiment are more complex structures which are derived from primary and secondary amino-functionalized or hydroxy-functionalized prepolymers, which may likewise be more highly functionalized.
  • Primary or secondary amino-terminated or hydroxy-terminated polyethers preferably ethylene oxide and propylene oxide-based polyethers, for example primary and secondary amino-terminated polyethers of the Jeffamine type, for example the ED and T series (Huntsman Corp.).
  • siloxane curds in ST 1 is preferably carried out via ⁇ , ⁇ -primary or secondary amino-functionalized polyorganosiloxanes.
  • the preparation of the corresponding ⁇ , ⁇ -primary or secondary aminoalkyl-terminated polyorganosiloxanes is state of the art (Silicones, Chemie und Technologie, Volkan Verlag Essen 1989, pp. 85-90).
  • polyfunctional polyorganosiloxanes carrying primary or secondary amino groups to form the hydrocarbon radical ST 1 .
  • These comb-like and optionally ⁇ , ⁇ -ammofunktionalformaten siloxanes are also known in the art.
  • polycarbonate and / or polyurethane-polyorganosiloxane compounds according to the invention are preferably prepared by a process which comprises the reaction of a compound of the formula (12)
  • ST is ST or ST and Y is as defined above, provided that at least one of ST and / or ST comprises a polyorganosiloxane radical.
  • Y NR, wherein R is as defined above, preferably hydrogen, and ST 5 and ST 6 are each -CH 2 -.
  • the polycarbonate and / or polyurethane-polyorganosiloxane compounds according to the invention can furthermore be prepared by a process which comprises the reaction of a compound of the formula
  • ST 5 and ST 6 are each -CH 2 -, Y and Y are independently -NR -, wherein R is as defined above, preferably hydrogen.
  • PPoollyyssiillooxxaann - VVeerrbbiinndduuingen at least one radical ST 2 of the formula (10) with quaternary groups:
  • ST 3 ST 4 and R 5 are as defined above.
  • Q is a radical capable of alkylating an amino group, and ST, together with the moiety resulting from Q after the quaternization reaction, forms the radical ST 4 ,
  • 4 'comprises 4V or higher polyorganosiloxane. and ST ST or a radical optionally modified after the reaction is ST, such as a haloalkyl radical after reaction.
  • radicals Q which are capable of quaternization or alkylation of the amino groups are preferably selected from epoxy groups and haloalkyl groups.
  • the polycarbonate and / or polyurethane polyorganosiloxane compounds are preferably prepared which thus have at least one radical ST of the formula (10):
  • these are primary-tertiary or secondary-tertiary diaminostructures, such as, for example, N, N-dimethylpropylenediamine.
  • the use of such diaminostructures requires the simultaneous use of poly-, especially difunctional, quaternizing agents, since otherwise no chain formation is possible. In this way, the formation of ST structural elements of the formula (10) takes place:
  • N-methylpiperazine involves the possibility that cyclic ST, in particular ST 2, structures may form.
  • Residual amino groups can optionally be alkylated following chain formation.
  • the amino-functional or hydroxy-functional ST 2 precursors are preferably carried out in the range of room temperature to 160 0 C, preferably up to 140 0 C.
  • the reaction times are a few minutes to a few hours.
  • the amino-functional precursors forming the ST 2 unit are generally more reactive than the hydroxy-functional ST 2 precursors.
  • reaction times, reaction temperatures and the conversion achieved depend in a particular way on the type of amino groups on the precursors forming the ST 2 unit. In general, primary amino groups react more readily than secondary amino groups.
  • the quaternization compound is required to to allow a polymerization with chain formation.
  • the ST 4 -containing partners are hydrocarbon-based ⁇ , ⁇ -epoxy- and / or halogen-functionalized substances.
  • Polyether for example, glycidyl-terminated polyether epoxy-terminated polyester, epoxy-terminated polycarbonates.
  • halogen-functionalized hydrocarbon derivatives preferably chlorides and bromides, are preferably
  • Hydrocarbon dihalides haloterminated polyethers, preferably ethylene oxide and propylene oxide based polyethers
  • Halocarboxylic acid esters of hydrocarbon diols and polyethers preferably ethylene oxide and propylene oxide based polyethers, especially
  • difunctional sensealkoxylate into corresponding glycidyl, halogen or halo carboxylic acid ester derivatives and to use according to the invention.
  • These are derived, for example, from succinic acid.
  • the hydrocarbon radicals ST 4 are more complex ⁇ , ⁇ -epoxy- or halogen-terminated structures which are derived from ⁇ , ⁇ -hydroxy-functionalized prepolymers. These ⁇ , ⁇ -hydroxy-functionalized prepolymers are preferably the reaction products of
  • OH terminated polyethers preferably ethylene oxide and propylene oxide based polyethers with diisocyanates
  • ⁇ , ⁇ -hydroxy-functionalized prepolymers are converted in a preferred embodiment into the corresponding ⁇ , ⁇ -halocarboxylic acid esters, especially chloroacetic acid esters, chloropropionic acid esters and chlorobutanoic acid esters.
  • siloxane blocks according to the invention into ST 4 is preferably carried out via ⁇ , ⁇ -epoxy-terminated siloxanes, preferably ⁇ , co-glycidyl and epoxycyclohexyl-terminated siloxanes ⁇ , ⁇ -haloalkyl-terminated siloxanes, preferably chloropropyl and chlorophenyl -terminated siloxanes ⁇ , ⁇ -halocarboxylic ester-terminated siloxanes, preferably esters of chloroacetic acid, chloropropionic acid and chlorobutyric acid, ⁇ , ⁇ -halocarboxylic acid ester-terminated polyethersiloxanes, preferably esters of chloroacetic acid, chloropropionic acid and chlorobutyric acid.
  • ⁇ , ⁇ -halocarboxylic acid ester-terminated polyethersiloxanes can be carried out in analogy to WO 02/10257, Example 1.
  • SiH siloxanes are reacted with halocarboxylic acid esters of olefinic or acetylenically unsaturated polyethers.
  • polyethersiloxanes with halocarboxylic acids, their anhydrides or acid chlorides (US Pat. No. 5,152,394, US Pat. No. 5,166,297).
  • the siloxane unit in the ST units has the structure
  • siloxane blocks are introduced into the ST structures via ⁇ , ⁇ -epoxy- or halogen-functionalized siloxane prepolymers, which can preferably be obtained from the corresponding ⁇ , ⁇ -hydroxyalkyl or ⁇ , ⁇ -hydroxypolyether-terminated siloxane prepolymers.
  • OH-terminated siloxane-containing prepolymers are preferably prepared by reaction of ⁇ , ⁇ -hydroxyalkyl-terminated siloxanes with diisocyanates, ⁇ , ⁇ -polyether-terminated siloxanes with diisocyanates and then converted into the epoxy and halogen derivatives.
  • a preferred embodiment is the ⁇ , ⁇ -halocarboxylic acid functionalized siloxane prepolymers prepared by esterification with e.g. the anhydrides and acid chlorides are accessible.
  • hydrocarbon-based or siloxane-based substances for forming the radical ST 2 .
  • These materials contain more than two of the epoxy or halogen functions discussed above.
  • higher functional hydrocarbon based substances are the glycidyl or chloroacetic ester derivatives of glycerol, pentaerythrol, sorbitol, and their ethoxylates and / or propoxylates. It is also within the scope of the invention to convert higher-functional acid alkoxylates into corresponding glycidyl or chloroacetic acid ester derivatives and to use them in accordance with the invention. These are derived, for example, from trimellitic acid or pyromellitic acid.
  • hydrocarbon-based or siloxane-based substances It is essential that the functionality of these higher-functionality hydrocarbon-based or siloxane-based substances is greater than two. It is also within the scope of the invention to use monofunctional hydrocarbon-based or siloxane-based substances for the formation of terminal radicals ST. These materials preferably contain one of the epoxy or halogen functions discussed above.
  • Suitable monofunctional siloxane-based substances with epoxy or halogen, preferably halocarboxylic acid ester substitution are e.g. from WO 02/10256 known. They can be obtained, for example, from unsaturated epoxy- or halocarboxylic ester-functional precursors, which are added to corresponding SiH siloxanes.
  • these monofunctional hydrocarbon-based or siloxane-based ST 2 " precursors are added to control the molecular weight of the polymers formed and, optionally, to control the degree of branching of the polymer chains in cooperation with the higher functionality ST 2 precursors 2 is added in stoichiometric amounts of acid in a manner known in the art
  • the acid anions are inorganic anions, such as Halide, especially chloride and organic anions such as carboxylate, especially C 2 to Cj 8 carboxylate, alkylpolyethercarboxylate, alkylsulfate, especially methosulfate, sulfonate, especially alkylsulfonate and alkylarylsulfonate, especially toluene sulfonate.
  • solvents are typical lacquer solvents, such as methoxypropyl acetate, butyl acetate, toluene.
  • quaternized polycarbonate and / or polyurethane polyorganosiloxane compounds are obtained which have at least one of the structural elements ST, including ST to ST, over polyorganosiloxane units.
  • the invention furthermore relates to the use of the polycarbonate and / or polyurethane-polyorganosiloxane compounds according to the invention for the production of coatings, surface modification agents, elastomers, thermosets, adhesives, primers for metal and plastic surfaces, polymer additives, detergent additives, rheological agents, cosmetic agents, fiber modifiers.
  • the polycarbonate and / or polyurethane-polyorganosiloxane compounds according to the invention may in particular have the function of so-called conditioning agents ("conditioners"), ie in particular favorably influence the hair properties, such as softness, gloss, fullness, combability, etc. in particular also in combination with other conventional conditioning agents, such as poly-alpha-olefins, fluorinated oils, fluorinated waxes, fluorinated rubbers, carboxylic acid esters having at least 10 carbon atoms, cationic polymers, in the medium of the formulation insoluble or soluble silicones, mineral oils, vegetable Oils and animal oils and mixtures thereof as described for example in WO 99/009939 can be used.
  • conditioning agents such as poly-alpha-olefins, fluorinated oils, fluorinated waxes, fluorinated rubbers, carboxylic acid esters having at least 10 carbon atoms, cationic polymers, in the medium of the formulation insoluble or soluble silicones,
  • the invention furthermore preferably relates to the use of the polycarbonate and / or polyurethane-polyorganosiloxane compound according to the invention for the preparation coatings or surface modifying agents for hard surfaces such as glass, ceramics, tiles, concrete and steel parts such as car bodies and hulls.
  • the invention preferably relates to the use of the polycarbonate and / or polyurethane-polyorganosiloxane compounds according to the invention for the preparation of primers for the connection of silicone elastomers with other substrates, such as steel, aluminum, glass, plastics, such as epoxy resins, polyamides, Polyphenylensulf ⁇ den, polyesters, such as polyterephthalates.
  • this relates to the use of the polycarbonate and / or polyurethane-polyorganosiloxane compounds according to the invention for the preparation of modifiers for thermoplastics, such as polyolefins, polyamides, polyurethanes, poly (meth) acrylates, polycarbonates.
  • modifiers for thermoplastics such as polyolefins, polyamides, polyurethanes, poly (meth) acrylates, polycarbonates.
  • polycarbonate and / or polyurethane-polyorganosiloxane compounds according to the invention are used alone for the said application.
  • polyurethane-polyorganosiloxane compounds themselves can be used directly as low-temperature impact modifiers, but they can also be suitably provided beforehand suitably by mixing, compounding, and masterbatch production, for example.
  • polycarbonate and / or polyurethane-polyorganosiloxane compounds may preferably be used as constituents in adhesives and sealants, as base material for thermoplastic elastomers, such as, for example, cable sheaths, hoses, Use gaskets, keypad mats, for membranes, such as selectively gas permeable membranes.
  • thermoplastic elastomers such as, for example, cable sheaths, hoses, Use gaskets, keypad mats, for membranes, such as selectively gas permeable membranes.
  • coatings such as antifouling, non-stick coatings, fabric-compatible coatings, flame-retardant coatings and biocompatible materials.
  • These can be used as coating agents for cosmetics, personal care products, paint additives, hips in detergents, defoamer formulations and textile processing, for modifying resins or for bitumen modification.
  • packaging materials for electronic components insulation or shielding materials, sealing material in condensate-forming cavities such as aircraft, airframes, ships, automobiles, headlamp anti-fogging coatings (inside), residential windows, vehicles or medical equipment, and additives for Cleaning, cleaning or care preparations, as an additive for personal care, as a coating material for wood, paper and cardboard, as mold release agents, as a biocompatible material in medical applications such as contact lenses, as a coating material for textile fibers or textile fabrics, as a coating material for natural products such Leather and furs, as material for membranes and as a material for photoactive systems z.
  • this relates to the use of the polycarbonate and / or polyurethane-polyorganosiloxane compounds according to the invention for the preparation of viscosity regulators, antistatic agents, mixture components for silicone rubbers, which crosslinks peroxide or by hydrosilylation (platinum catalysis) to form elastomers and modifying the surface properties, modifying the diffusion of gases, liquids, etc., or modifying the swelling behavior of the silicone elastomers, softening textile fibers to treat the textile fibers before, during, and after washing, modifying agents of natural and synthetic fibers, such as hair, cotton fibers and synthetic fibers, such as polyester fibers and polyamide fibers; fabrics, textile finishing agents, and detergent-containing formulations, such as detergents, cleaners.
  • natural and synthetic fibers such as hair, cotton fibers and synthetic fibers, such as polyester fibers and polyamide fibers
  • fabrics, textile finishing agents, and detergent-containing formulations such as detergents, cleaners.
  • the present invention furthermore relates to novel detergent formulations, cosmetic formulations, fiber treatment formulations containing the polycarbonate and / or polyurethane-polyorganosiloxane compounds according to the invention.
  • the polycarbonate and / or polyurethane-polyorganosiloxane compounds according to the invention may be present for example in solid or liquid detergent formulations in proportions of about 0.1 to 10 wt .-% based on the total amount of the formulation, in cosmetic formulations and formulations for fiber treatment, such as Fabric care before, during and after the laundry, in proportions of about 0.1 to 50 wt .-% based on the total amount of the formulation.
  • the polycarbonate and / or polyurethane polyorganosiloxane compounds according to the invention may preferably be used for the treatment and finishing of hard surfaces, such as glass, ceramics, tiles, plastic surfaces, metal surfaces, paint surfaces, especially hulls and automobile bodies, especially in dryer formulations for machine washing, as an adhesive or primer, preferably for the combination of silicone elastomers with other substrates, such as steel, aluminum, glass, epoxy resin, polyamide, as modifiers, eg Low-temperature impact modifiers and polarity modifiers, for hydrocarbon-based polymers and silicone-based elastomer systems based on peroxidic and Pt-catalyzed crosslinking.
  • hard surfaces such as glass, ceramics, tiles, plastic surfaces, metal surfaces, paint surfaces, especially hulls and automobile bodies, especially in dryer formulations for machine washing
  • an adhesive or primer preferably for the combination of silicone elastomers with other substrates, such as steel, aluminum, glass, epoxy resin, polyamide, as modifiers, eg Low-temperature
  • They can furthermore be used for the treatment of natural and synthetic fibers, for example cotton, wool, polyester and polyamide-based synthetic fibers, especially in the form of textiles, in special fiber treatment agents, in particular detergent formulations containing anionic, nonionic and cationic surfactants Compounds can be incorporated directly into the detergent, separately in the running Washing process or after the washing process can be dosed, and the treated substrates are given softness, improved elasticity and reduced crease tendency to obtain an acceptable hydrophilicity.
  • natural and synthetic fibers for example cotton, wool, polyester and polyamide-based synthetic fibers, especially in the form of textiles
  • special fiber treatment agents in particular detergent formulations containing anionic, nonionic and cationic surfactants
  • Compounds can be incorporated directly into the detergent, separately in the running Washing process or after the washing process can be dosed, and the treated substrates are given softness, improved elasticity and reduced crease tendency to obtain an acceptable hydrophilicity.
  • They may also serve as a component of separate softening systems, especially based on cationic surfactants, after the washing of fibers and fabrics, as an ironing aid and as a means of preventing or reversing textile creasing.
  • fiber equipment especially for the original equipment and treatment of, for example, cotton, wool, polyester and polyamide-based synthetic fibers, especially in the form of textiles, paper and wood.
  • Particularly preferred fields of application for the polycarbonate and / or polyurethane-polyorganosiloxane compounds according to the invention are also, preferably aqueous, solutions, mixtures, emulsions and microemulsions, in particular as a basis for cosmetic formulations.
  • polycarbonate and / or polyurethane-polyorganosiloxane compounds according to the invention can be used as pure substance, solution, mixture, emulsion or microemulsion in the form of liquids, creams or pastes as starting material for the preparation of suitable, inventive cosmetic formulations of different viscosities.
  • the process for the preparation of formulations of the polycarbonate and / or polyurethane-polyorganosiloxane compounds according to the invention can consist, for example, of the following steps: a) preparing a premix in the form of solutions, mixtures or emulsions with the polycarbonate and / or polyurethane polyorganosiloxane compounds according to the invention and b) preparing a further mixture using the premix a) and optionally adding further surfactants, auxiliaries and other additives or c) combining steps a) and b), in which the mixing of the components with stirrers, dissolvers, kneaders, pumps, mixing screws, mixing nozzles, low and high pressure emulsifiers is carried out.
  • the formulations containing the polycarbonate and / or polyurethane polyorganosiloxane compounds according to the invention can be prepared, for example, in various dosage forms, such as for the hair treatment.
  • the compositions containing the polycarbonate and / or polyurethane-polyorganosiloxanes compounds according to the invention are preferably used as cosmetic formulations for the treatment of keratin-containing substrates such.
  • Alcoholic and polyalcoholic solvents and mixtures thereof with water, oil-like substances and conventional silicones (including polydimethylsiloxanes) and binary and ternary mixtures of. are suitable for the preparation of solutions and mixtures containing the inventive polycarbonate and / or polyurethane-polyorganosiloxane Solvents and / or oily substances and / or silicones.
  • Particularly preferred solvents here are ethanol, isopropanol, ethylene glycol and ethylene glycol ethers, polyethylene glycols and their ethers, propylene glycol and propylene glycol ethers, polypropylene glycols and their ethers and glycerol and mixtures thereof.
  • Particularly preferred oily substances are mineral oil products as well as oils of vegetable, animal and synthetic origin and mixtures thereof.
  • cyclomethicones (according to INCI) cyclomethicones, cyclotetrasiloxanes, cyclopentasiloxanes, cyclohexasiloxanes, dimethicones having a viscosity range of 0.65 to 60,000,000 mPa.s at 25 0 C and dimethiconol having a viscosity range of 10 to 60,000,000 mPa.s at 25 0 C.
  • Preferred solutions and mixtures containing the polycarbonate and / or polyurethane-polyorganosiloxane compounds according to the invention have the following composition in% by weight, based on the total weight of the composition:
  • compositions of the emulsions of the polycarbonate and / or polyurethane-polyorganosiloxane compounds according to the invention To prepare the emulsions, water and nonionic, cationic and amphoteric surfactants and surfactant mixtures are generally used.
  • emulsions can auxiliaries such.
  • inorganic and organic acids bases and buffers, salts, thickeners, stabilizers for emulsions such.
  • ' xanthan gum ' preservatives, foam stabilizers, defoamers and solvents such.
  • alcohols ethanol, isopropanol, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, glycol ethers and glycerol and mixtures thereof).
  • polycarbonate and / or polyurethane-polyorganosiloxane compounds according to the invention which are used in the emulsions can themselves serve as emulsifier in the preparation of emulsions.
  • a preferred emulsion which can preferably be used for the preparation of cosmetic formulations, consists, for example, of the following constituents in% by weight, based on the total amount of the composition:
  • microemulsions having a high active content of polycarbonate and / or polyurethane-polyorganosiloxane compounds according to the invention since, in addition to the possibility of producing clear cosmetic formulations, they additionally have the advantage of simple process incorporation ("cold process") It is possible to use the polycarbonate and / or polyurethane-polyorganosiloxane compounds according to the invention in the preparation of microemulsions in the form of to use solutions and mixtures described above.
  • a preferred active content of the polycarbonate and / or polyurethane-polyorganosiloxane compounds according to the invention in the emulsion is between 5 and 60% by weight, more preferably 10-50% by weight, based on the total amount of the composition.
  • a very particularly preferred microemulsion consists of the following, but not limiting constituents in wt .-% based on the total amount of the microemulsion:
  • Another object of the invention is the use of the solutions prepared with the polycarbonate and / or polyurethane-polyorganosiloxane compounds according to the invention, mixtures or emulsions in a cosmetic formulation.
  • These cosmetic formulations are prepared using the previously prepared solutions or emulsions, but they may also be prepared directly from the individual components.
  • Cosmetic formulations include, for example:
  • the formulations also include hair colorants, which can be distinguished depending on the washing resistance of the obtained color result in 3 types - permanent, semi-permanent and temporary hair dyes.
  • hair here includes all keratin fibers, but in particular human hair.
  • the hair dyes contain, for example, besides the polycarbonate and / or polyurethane polyorganosiloxane compounds according to the invention, customary silicones, surfactants, auxiliaries and colorants.
  • Each of these ingredients can be used either alone or in combination with other ingredients, and stands for additional functions in the formulations which increase the volume, combability and gloss, as well as reduce the washout of color from and from colored keratinous substrates such as human and animal hair and contain at least one polycarbonate and / or polyurethane polyorganosiloxane compounds.
  • silicones include, for example: Cyclic, linear and branched polydimethylsiloxanes having a viscosity from 0.65 to 200,000,000 mPa.s at 25 0 C, and mixtures thereof such as for example octaorgano cyclotetrasiloxanes, octamethylcyclotetrasiloxanes, decaorganocyclopentasiloxanes, dodecaorganocyclohexasiloxanes, the organic radical preferably being methyl, such as SF 1173, SF 1202, SF 1217, SF 1204 and SF 1258 from Momentive Performance Materials formerly GE Bayer Silicones, dimethicones such as Baysilone M oils ( M3 to M 2,000,000), SE 30, SF 1214, SF 1236, SF 1276 and CF 1251 from GE Bayer Silicones
  • solid silicones so-called MQ resins, e.g. SR 1000 from GE Bayer Silicones / Momentive Performance Materials and their solutions in solvents such as the above-mentioned silicones and aliphatic solvents, e.g. Isododecane.
  • MQ resins e.g. SR 1000 from GE Bayer Silicones / Momentive Performance Materials
  • solvents such as the above-mentioned silicones and aliphatic solvents, e.g. Isododecane.
  • organofunctional silicones such as alkyl-, aryl-, arylalkyl-, phenyl-, fluoroalkyl-, and polyether-modified silicones such as the types SF 1632, SF 1642, SF 1555, Baysilone CF 1301, Baysilone PK 20, FF 157, SF 1188A, SF 1288 and SF 1388 from GE Bayer Silicones / Momentive Performance Materials.
  • anionic surfactants are as
  • Taurides sarcosides, sulfosuccinates, protein-fatty acid condensates, alkyl phosphates and
  • Alkyl ether Here, the free acids and their alkali metal salts, magnesium, ammonium and mono-, di- and triethanolamine salts.
  • the alkyl and acyl groups typically contain 8-18 C atoms and may be unsaturated.
  • the alkyl ether sulfates, alkyl amide ether sulfates, alkyl ether carboxylates and alkyl ether phosphates can be 1-10 ethylene oxide or propylene oxide or a
  • amphoteric surfactants are listed below amphoteric surfactants.
  • Alkylbetaines alkylamidobetaines, sulfobetaines, acetates and diacetates, imidazolines,
  • the alkyl and acyl groups contain 8-19 carbon atoms.
  • Nonionic surfactants are nonionic surfactants:
  • nonionic surfactants As an example, but not limiting, the following nonionic surfactants as
  • Alkyl ethoxylates aryl ethoxylates, ethoxylated esters, polyglycol amides, polysorbates,
  • Glycerin fatty acid ethoxylates alkylphenol polyglycol ethers and sugar surfactants such as e.g. Alkylglycosides.
  • cationic surfactants For cationic surfactants, a distinction is made between pure cationic surfactants and cationic polymers.
  • nonionic surfactants As an example, but not limiting, the following nonionic surfactants as
  • Cationically modified polymers are used in addition to the pure cationic surfactants, in particular for "2-in-1" shampoos
  • a comprehensive description of these polymers is given in US Pat. No. 5,977,038 and WO 01-41720 Al
  • Preferred are cationic polyacrylamides, cationic protein derivatives, hydroxyalkyl cellulose ethers and cationic guar Derivatives
  • Particular preference is given to cationic guar derivatives with the CTFA name Guar Hydroxypropyltrimonium Chloride
  • These types are available under the trade names Cosmedia Guar C 261 (Henkel), Diagum P 5070 (Diamalt), Jaguar C types and Jaguar EXCEL from Rhodia.
  • auxiliaries are part of the following auxiliaries.
  • Inorganic and organic acids, bases and buffers, salts, alcohols such as e.g.
  • Xanthan gum moisturizers, preservatives, foam stabilizers,
  • Titanium dioxide Titanium dioxide, collagen hydrolyzate, keratin hydrolyzate, silk hydrolyzate, antidandruff agents such as e.g. Zinc pyrithione, salicylic acid, selenium disulfide, sulfur and
  • Perfume oils perfume oils, fragrances, styling polymers, moisturizers, plant extracts and other natural or nature-identical raw materials.
  • Dyes and other ingredients of hair dyes are described in: A. Domsch, The cosmetic preparations, Verlag für Chem. Industrie, 4th edition, 1992. Dyes are described in: Regulation on Cosmetic Agents (Cosmetics Regulation), Federal Law Gazette 1997, Part I S 2412, ⁇ 3 and Annex 3 and in the European Community (EC) Directive, 76/68 / EEC, Annex IV.
  • EC European Community
  • hair dyes are differentiated into permanent, semi-permanent and temporary hair dyes.
  • Permanent dyeings that are not washed out by several washes (more than 10) are caused by chemical reaction between dye precursors under oxidative conditions by hydrogen peroxide. In this case, the mixture of the corresponding components determines the achievable color result.
  • a distinction is made in the precursors between oxidation bases (developers) and coupling components (modifiers).
  • oxidation bases are suitable as constituents of the formulations: m- and p-phenylenediamines (diaminobenzenes), their N-substituted derivatives and .alpha
  • oxidation bases and coupling components are incorporated with surfactants in oil-in-water emulsions, but also simple solutions or shampoos are known as formulations.
  • the formulations also contain antioxidants, e.g. Sodium sulfite, sodium dithionite, ascorbic acid or thioglycolic acid to stabilize the precursors and are treated with alkaline substances such. Ammonia adjusted to a pH between 8 and 12 (preferably 9-11).
  • surfactants are added as wetting agents, complexing agents for heavy metals, fragrances for covering the ammonia odor, conditioners for improving the hair feeling and for protecting the hair and solvents such as ethanol, ethylene glycol, glycerol or benzyl alcohol.
  • permanent hair colorants are offered as 2-component systems consisting of color solution, cream or shampoo described above and from the developer solution.
  • the developer solution in this case contains between 6-12% hydrogen peroxide and can optionally be added with components of the formulation containing the color components.
  • the peroxide solution must be carefully stabilized.
  • Temporary dyeings unlike the semipermanent hair dyes contain larger dye molecules that are unable to penetrate the hair. They are designed to maintain staining for 1-6 washes. Typically, azo and basic dyes and, azine and thiazine derivatives are used here. As far as the composition of the formulations is concerned, the same applies for semipermanent and permanent hair dyes. Dyes and other ingredients of hair dyes are described in: A. Domsch, The cosmetic preparations, Verlag für Chem. Industrie, 4th edition, 1992. Dyes are described in: Regulation on Cosmetic Agents (Cosmetics Regulation), Federal Law Gazette 1997, Part I S 2412, ⁇ 3 and Annex 3 and in the European Community (EC) Directive, 76/68 / EEC, Annex IV.
  • EC European Community
  • a typical shampoo formulation according to the invention for the care and conditioning of hair which is not limiting on the invention consists of the following constituents in% by weight, in each case based on the overall formulation:
  • a special, but not limiting the invention shampoo formulation consists of the following components in wt .-%:
  • a typical hair conditioner according to the invention, but not limited to the invention, for the care and conditioning of hair consists of the following constituents in% by weight:
  • a special composition of a hair conditioner which does not limit the invention consists of the following constituents in% by weight:
  • Polyorganosiloxane compounds (as a 43.5% emulsion in water with nonionic emulsifiers) 0 - 15% Silicones Conditioners (Co-adjuvants) 0 - 10% Cetrimonium chloride (25 - 35%) 0 - 3% Guar Hydroxypropyltrimonium Chloride 1 - 10% Cetearyl Alcohol 0 - 10% Glycerol 0.01 - 1% Phenoxyethynol (and) Methylparaben (and)
  • citric acid 0 - 1% citric acid to 100% supplemented by water.
  • a typical, according to the invention but not limiting hair care treatment for the care and conditioning of hair consists of the following constituents in wt .-%:
  • a special hair care treatment which does not limit the invention consists of the following constituents in% by weight:
  • a very special hair care treatment which does not limit the invention, consists of the following constituents in% by weight:
  • Polyorganosiloxane compounds (as a 43.5% emulsion in water with nonionic emulsifiers)
  • a typical formulation according to the invention, but not limiting the invention for temporary, semi-permanent or permanent hair dyeing care and conditioning of the hair, consists of the following constituents in% by weight:
  • a special color cream according to the invention but not limiting the invention for permanent hair coloring, consists of the following constituents in% by weight:
  • polycarbonate and / or polyurethane polyorganosiloxane compounds according to the invention (as a 20% emulsion in water with nonionic emulsifiers)
  • a special dye solution for permanent hair dyeing according to the invention but not limited to the invention consists of the following constituents in% by weight:
  • polycarbonate and / or polyurethane polyorganosiloxane compounds according to the invention (as a 20% emulsion in water with nonionic emulsifiers)
  • silicone conditioning agent co-adjuvants
  • a typical developer formulation for permanent hair dyeing according to the invention which is not limited to the invention, consists of the following constituents in% by weight:
  • a special, non-limitative developer of the invention for a permanent hair dye consists of the following constituents in% by weight:
  • polycarbonate and / or polyurethane polyorganosiloxane compounds according to the invention (as a 20% emulsion in water with nonionic emulsifiers) 10-30% hydrogen peroxide (30%)
  • Pentasodium Pentetate pentaacetate
  • the erf ⁇ ndungsmä J solutions or mixtures are preferably suitable for the preparation of cosmetic formulations, such as for the treatment, conditioning, cleaning and / or care of dyed or to be dyed substrates. That is to say that the formulations comprising at least one polycarbonate and / or polyurethane polyorganosiloxane compound according to the invention can be used in particular for the cleaning, care and conditioning of fibrous or sheetlike substrates and if these are dyed and their color impression is to be retained as far as possible.
  • the formulations containing at least one novel polycarbonate and / or polyurethane-polyorganosiloxane compound according to the invention can furthermore be used for the cleaning, care and treatment and conditioning of keratin-containing substrates, since they serve as cleaning agents for wool, for washing and / or increasing the volume and / or the combing and / or gloss and / or to reduce the leaching of the color to and from dyed or simultaneously to be dyed keratin-containing substrates such as human and animal hair are suitable.
  • the formulations containing at least one inventive polycarbonate and / or polyurethane-polyorganosiloxane compound can be used in particular for the cleaning, care and treatment, cleaning and care of keratin-containing fibers or hair before, during and / or after the dyeing process, since the Hair colorants formulated herewith simultaneously lead to the improvement of the softness and / or the reduction of the wet and dry combing forces and / or to the increase of the gloss and / or increase the hair volume and / or to reduce the leaching of dyes from and from tinted and dyed hairs.
  • the dosage form it is possible, on the one hand, to incorporate the polycarbonate and / or polyurethane-polyorganosiloxane compounds according to the invention into non-transparent fabric softener dispersions or fabric softener emulsions or transparent microemulsions or solutions.
  • Typical further components for such non-transparent or transparent formulations are: quaternary ammonium compounds, preferably alkanoic acid ester units containing quaternary ammonium compounds as plasticizers, organic solvents, preferably monohydric and polyhydric alcohols,
  • glycols and oligoglycols such as dipropylene glycol monobutyl ether, tripropylene monomethyl ether, diethylene glycol diacetate, to improve the solubility and transparency of the formulation
  • Diols and higher alcohols of longer-chain hydrocarbons for example 2,2,4-trimethyl-l, 3-pentanediol, to increase the solubility of the plasticizer components, nonionic surfactants, preferably alkoxylates of branched or unbranched Cs to C / io alcohols and fatty acid esters of alkylene oxides for emulsion stabilization or microemulsion production perfume
  • Viscosity regulator dyes preservatives preservatives.
  • Fatty amines or their complexes with anionic surfactants as conditioning agents quaternary ammonium compounds, preferably quaternary ammonium compounds containing alkanoic acid ester units as plasticizers non-ionic plasticizers, for example based on sorbitan esters,
  • Soil release agents for example based on cellulose ethers, guar
  • the carrier material is a sponge-like or porous sheet-like material which has a sufficient capacity to accommodate the laundry freshener formulation.
  • woven and nonwoven materials used. These are materials based on natural or synthetic polymers, such as wool, cotton, sisal, linen, cellulose esters, polyvinyl compounds, polyolefins, polyamides, polyurethanes, polyesters.
  • the invention furthermore relates to a reactive composition comprising at least one compound of the formula (10)
  • At least one of the radicals ST comprises a polyorganosiloxane radical.
  • Y is NR 2 , wherein R 2 is as defined above, preferably hydrogen, and ST and ST are each -CH 2 -.
  • the invention furthermore relates to a reactive composition comprising at least one compound of the formula (13)
  • Q is a radical capable of alkylating an amino group and ST is taken together with that resulting from Q after the quaternization reaction
  • Polyorganosiloxanrest comprises.
  • the said cured compositions can be cured in particular by heating and / or adding catalyst.
  • the reactive compositions can be used in particular as lK (component) composition or less preferably as 2K (component) composition.
  • radical ST comprises at least one polyorganosiloxane radical.
  • ST is preferably ST 1 which is as defined above
  • ST 5 and ST 6 are each preferably -CH 2 -
  • Y is preferably Y 1 , which is preferably NR, wherein R is as defined above, preferably hydrogen ,
  • the polymers according to Examples 1 and 2 can be incorporated in an amount of 0.5-3% in powdered and liquid detergents based on anionic and / or nonionic surfactants, where they exert their particular softening effect on the fiber materials to be cleaned.

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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)
  • Silicon Polymers (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Detergent Compositions (AREA)
  • Epoxy Resins (AREA)
  • Paints Or Removers (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne de nouveaux composés de polycarbonate et/ou de polyuréthanne-polyorganosiloxane, leurs procédés de production, leur utilisation, des précurseurs pour leur production, ainsi que des compositions réactives renfermant ces précurseurs.
EP08759862A 2007-05-21 2008-05-21 Composés de polycarbonate et/ou de polyuréthanne-polyorganosiloxane Withdrawn EP2150570A1 (fr)

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DE102007023869A DE102007023869A1 (de) 2007-05-21 2007-05-21 Neue Polycarbonat- und/oder Polyurethan-Polyorganosiloxan-Verbindungen
PCT/EP2008/056260 WO2008142109A1 (fr) 2007-05-21 2008-05-21 Composés de polycarbonate et/ou de polyuréthanne-polyorganosiloxane

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DE102007023869A1 (de) 2008-12-18
US20100210809A1 (en) 2010-08-19
BRPI0811775A2 (pt) 2014-11-11
WO2008142109A1 (fr) 2008-11-27
CN101802053B (zh) 2013-05-08
JP2010529217A (ja) 2010-08-26
JP5624883B2 (ja) 2014-11-12
CN101802053A (zh) 2010-08-11
US8410236B2 (en) 2013-04-02

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