WO2005111106A1 - Carbodiimides contenant des groupes silane - Google Patents

Carbodiimides contenant des groupes silane Download PDF

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Publication number
WO2005111106A1
WO2005111106A1 PCT/EP2005/004819 EP2005004819W WO2005111106A1 WO 2005111106 A1 WO2005111106 A1 WO 2005111106A1 EP 2005004819 W EP2005004819 W EP 2005004819W WO 2005111106 A1 WO2005111106 A1 WO 2005111106A1
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Prior art keywords
carbodiimides
ethyl
methyl
carbodiimide
catalysts
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PCT/EP2005/004819
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German (de)
English (en)
Inventor
Markus Krämer
Oliver Steffen Henze
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BASF SE
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BASF SE
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Priority to DE112005000561.5T priority Critical patent/DE112005000561B4/de
Publication of WO2005111106A1 publication Critical patent/WO2005111106A1/fr
Anticipated expiration legal-status Critical
Ceased 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
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/166—Catalysts not provided for in the groups C08G18/18 - C08G18/26
    • C08G18/168—Organic compounds
    • 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
    • C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
    • C08G18/025—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only the polymeric products containing carbodiimide groups
    • 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
    • C08G18/088—Removal of water or carbon dioxide from the reaction mixture or reaction components
    • C08G18/0885—Removal of water or carbon dioxide from the reaction mixture or reaction components using additives, e.g. absorbing agents
    • 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
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6633—Compounds of group C08G18/42
    • C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/664—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
    • 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/71—Monoisocyanates or monoisothiocyanates
    • C08G18/718—Monoisocyanates or monoisothiocyanates containing silicon
    • 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
    • C08G18/7628—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group
    • C08G18/765—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group alpha, alpha, alpha', alpha', -tetraalkylxylylene diisocyanate or homologues substituted on the aromatic ring

Definitions

  • the invention relates to carbodiimides containing the following structure:
  • n 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 13, 14, 15, 16, 17, 18, 19 or 20, preferably 2 to 8 , particularly preferably on average 4 to 6,
  • R 2 aliphatic, cycloaliphatic, araliphatic or aromatic, optionally substituted, optionally branched chain radical, preferably alkylene radical with 1 to 20, preferably 2 to 10, particularly preferably 2 to 4 hydrocarbon atoms,
  • R 3 methyl, ethyl, -O-CH 3 , -O-CH 2 -CH 3 , -O-CH (CH 3 ) 2 , -OC (CH 3 ) 3 or -O-CH 2 -CH 2 - O-CH 3 , preferably -O-CH 3 or -O-CH 2 -CH 3 , particularly preferably -O-CH 3 ,
  • R 4 methyl, ethyl, -O-CH 3 , -O-CH 2 -CH 3 , -O-CH (CH 3 ) 2 , -OC (CH 3 ) 3 or -O-CH 2 -CH 2 - O-CH 3 , preferably -O-CH 3 or -O-CH 2 -CH 3 , particularly preferably -O-CH 3 ,
  • R 5 methyl, ethyl, -O-CH 3 , -O-CH 2 -CH 3 , -O-CH (CH 3 ) 2 , -OC (CH 3 ) 3 or -0-CH 2 -CH 2 - O-CH 3 , preferably -O-CH 3 or -O-CH 2 -CH 3 , particularly preferably -O-CH 3 .
  • the invention further relates to mixtures comprising the carbodiimides according to the invention and at least one compound from the following group: polyurethanes which have ester structures, polyethylene and / or butylene terephthalate, polyether esters, polyester amides, polycaprolactones, unsaturated polyester resins, polyamides, in particular thermoplastic polyurethanes the carbodiimides according to the invention and preferably ester structures.
  • polyurethanes which have ester structures, polyethylene and / or butylene terephthalate, polyether esters, polyester amides, polycaprolactones, unsaturated polyester resins, polyamides, in particular thermoplastic polyurethanes the carbodiimides according to the invention and preferably ester structures.
  • silane groups is understood to mean, in particular, organic silicon groups.
  • Organic carbodiimides are known and are used, for example, as a stabilizer against the hydrolytic degradation of compounds containing ester groups, for example polyaddition and polyconden
  • Carbodiimides can be prepared by generally known processes, for example by the action of basic catalysts on mono- or polyisocyanates with elimination of carbon dioxide.
  • Suitable catalysts are, for example, heterocyclic compounds containing phosphorus, metal carbonyls, phospholines, phospholenes and phospholidines and their oxides and sulfides.
  • Such carbodiimides, their preparation and their use as stabilizers against the hydrolytic cleavage of polyester-based plastics are e.g. described in DE-A 4 318 979, DE-A 4 442 724 and EP-A 460 481.
  • EP-A 969 029, EP-A 785 222, EP-A 507 407, EP-A 1 162 237 and US 4 118 536 describe the preparation of carbodiimides which have alkoxysilane end groups.
  • the object of the present invention was to develop improved carbodiimides as stabilizers against the hydrolytic cleavage of plastics based on polyester, which have an optimal incorporation into the starting components of the plastics or in the plastics themselves and also the dynamic and static properties of the plastics, in particular of polyurethane elastomers, not adversely affect.
  • a particular aim was to maintain the property profile of the plastics to be stabilized, in particular the thermoplastic polyurethane, even under conditions in which hydrolysis usually occurs.
  • the hydrolytic degradation of a polyester from one molecule by splitting two molecules is accompanied by a corresponding loss of molecular weight.
  • the carbodiimide trapping the acidic polymer residue results in a combination of these two molecules. This does not solve the problem of molecular weight reduction.
  • the particular advantage of the carbodiimides according to the invention lies both in their outstanding activity as hydrolysis stabilizers and in their ability to build up crosslinks and thus higher molar masses in the polymer via the siloxane groups at the end of the carbodiimide. This particular advantage is particularly advantageous in thermoplastic plastics, preferably thermoplastic polyurethane.
  • the carbodiimides according to the invention provide a very good crosslinking capacity through a simple and economical production process, which can bring about a clear molecular weight build-up in the polymer and thus ensures a high property profile of the polymer.
  • carbodiimides according to the invention have the following advantages:
  • n 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 13, 14, 15, 16, 17, 18, 19 or 20, preferred 2 to 8, particularly preferably on average 4 to 6.
  • the carbodiimides according to the invention can be prepared by generally known reaction of the isocyanate groups with one another with elimination of carbon dioxide in the presence of customary catalysts which are known for this reaction and have been described at the beginning.
  • the carbodiimides according to the invention can be obtained by reacting 1,3-bis (1-methyl-1-isocyanato-ethyl) benzene in the presence of catalysts with elimination of carbon dioxide to give carbodiimides and then the carbodiimide having isocyanate groups with a Compound which has at least one isocyanate group and at least one or two, preferably two silane groups, preferably trialkoxysilane groups, in the presence of catalysts with elimination of carbon dioxide to give the carbodiimide.
  • the molar ratio of the NCO groups of the carbodiimide having isocyanate groups to the isocyanate groups of silane is usually 10: 1 to 0.2: 1, preferably 5: 1 to 0.5: 1, particularly preferably 1: 1 to 0, 5: 1, especially 1: 1.
  • the carbodiimides according to the invention can be obtained by mixing 1,3-bis (1-methyl-1-isocyanato-ethyl) benzene in a mixture with a compound which has at least one isocyanate group and at least one, preferably a silane group, preferably trialkoxysilane group has, in the presence of catalysts with carbon dioxide release to carbodiimides.
  • the preparation of the carbodiimides according to the invention by reacting the isocyanate groups can be carried out at elevated temperatures, e.g. at temperatures from 50 to 200 ° C, preferably from 150 to 185 ° C, advantageously in the presence of catalysts with carbon dioxide elimination. Methods suitable for this are described, for example, in GB-A-1 083 410, DE-B 1 130 594 (GB-A-851 936) and DE-A-11 56 401 (US-A-3 502 722).
  • the following have proven to be excellent catalysts, e.g. Phosphorus compounds, which are preferably selected from the group of phospholenes, phospholenoxides, phospholidines and phospholinoxides.
  • the polycarbodiimide formation is usually ended.
  • the catalysts can be distilled off under reduced pressure or by adding a deactivator, such as e.g. Phosphorus trichloride can be deactivated.
  • a deactivator such as e.g. Phosphorus trichloride can be deactivated.
  • the polycarbodiimide preparation can also be carried out in the absence or presence of solvents which are inert under the reaction conditions.
  • the specialist adjust the degree of condensation in the usual way.
  • the easiest way to follow the course of the reaction is to determine the NCO content.
  • Other parameters such as viscosity increase, color deepening or CO 2 development can also be used to monitor the process and control the reaction.
  • TMXDI 1,3-Bis- (1-methyl-1-isocyanato-ethyl) -benzene, hereinafter also referred to as TMXDI, is used as the diisocyanate for the preparation of the carbodiimides according to the invention.
  • the TMXDI can be used in mixtures with other, generally customary isocyanates, for example hexamethylene diisocyanate, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethyl-cyclohexane (isophorone diisocyanate), di (cyclohexyl) methane diisocyanate, trimethylhexamethylene diisocyanate, dodecane diisocyanate, octane diisocyanate - Isocyanate and / or cyclohexane-1,4-diisocyanate.
  • at least 30 mol% of TMXDI is preferably used.
  • isocyanates preferably monoisocyanates, containing at least one, preferably one, silver group
  • the carbodiimides according to the invention containing at least one, preferably one to twenty carbodiimide structures, particularly preferably the average degree of condensation (number average), i.e. the average number of carbodiimide structures in the carbodiimides according to the invention one to ten, particularly preferably 2 to 8, in particular 4 to 6.
  • number average i.e. the average number of carbodiimide structures in the carbodiimides according to the invention one to ten, particularly preferably 2 to 8, in particular 4 to 6.
  • the monocarbodiimides and / or oligomeric polycarbodiimides according to the invention are outstandingly suitable as acceptors for carboxyl compounds and are therefore preferably used as stabilizers against the hydrolytic degradation of compounds containing ester groups, for example polymers containing ester groups, for example polycondensation products such as thermoplastic polyesters such as polyethylene and butylene terephthalate and polyether esters , Polyamides, polyester amides, polycaprolactones and unsaturated polyester resins and polyester esters such as block copolymers of polyethylene or butylene terephthalate and polycaprolactone.
  • polymers containing ester groups for example polycondensation products
  • thermoplastic polyesters such as polyethylene and butylene terephthalate and polyether esters
  • Polyamides, polyester amides, polycaprolactones and unsaturated polyester resins and polyester esters such as block copolymers of polyethylene or butylene terephthalate and polycaprolactone.
  • polyurethanes for example polyurethanes, polyureas and polyurethane-polyurea elastomers, which contain ester groups.
  • ester groups are generally known. Their starting substances, manufacturing processes, structures and properties are described in a variety of ways in the standard literature. Due to the good solubility in the structural components for the production of poly Urethanes and good compatibility with the polyurethanes formed are the (poly) carbodiimides according to the invention particularly suitable as stabilizers against the hydrolytic degradation of polyurethanes, preferably compact or cellular polyurethane elastomers and in particular thermoplastic polyurethanes and cellular or compact elastomers.
  • the concentration of the carbodiimides according to the invention in the polycondensation or polyaddition products containing ester groups to be stabilized is generally 0.05 to 10% by weight, preferably 0.1 to 5% by weight, based on the total weight of the mixture. In individual cases, depending on the stress on the plastic due to hydrolysis, the concentration can also be higher.
  • the carbodiimides which can be used according to the invention can be introduced into the products containing ester groups to be stabilized by various methods.
  • the carbodiimides according to the invention can be combined with one of the structural components for the preparation of the polyadducts, e.g. the polyisocyanates and / or polyhydroxyl compounds for the production of polyurethanes are mixed, or the carbodiimides can be added to the reaction mixture for the production of the polyurethanes.
  • the carbodiimides according to the invention can be incorporated into the melt of the fully reacted polyaddition or polycondensation products.
  • the carboxyl-containing polyester polyols are first treated with the carbodiimides according to the invention to reduce the acid contents and then these, optionally with the addition of further amounts of carbodiimides, with polyisocyanates, optionally in the presence of additional ones Tools and additives, brought to reaction.
  • the carbodiimides according to the invention can be introduced into the polyurethane via the isocyanate component.
  • the carbodiimides according to the invention are particularly useful when they are introduced into the polymer containing ester groups during customary packaging.
  • the carbodiimides according to the invention are particularly preferably used in the production of polyurethanes, for example cellular, for example microcellular polyurethanes, preferably polyurethane elastomers, in particular thermoplastic polyurethanes.
  • polyurethanes in particular polyurethane elastomers
  • These polyurethanes, in particular polyurethane elastomers can be prepared by known reaction of conventional starting components, ie isocyanates, compounds which are reactive toward isocyanates, optionally blowing agents, before adds water and optionally catalysts, auxiliaries and / or additives in the presence of the carbodiimides according to the invention.
  • the carbodiimides according to the invention are preferably added to the component which contains the blowing agent, preferably water.
  • polyurethanes preferably thermoplastic polyurethanes
  • processes for the production of polyurethanes preferably thermoplastic polyurethanes, preferably by reacting isocyanates, compounds which are reactive toward isocyanates, optionally blowing agents and optionally catalysts, auxiliaries and / or additives are preferred, the reaction being carried out in the presence of the carbodiimides according to the invention.
  • the carbodiimides are suitable, for example: also to terminate esterification reactions in the production of polyester when the desired degree of polycondensation has been reached.
  • thermoplastically processable polyurethane elastomers according to the invention can be used for extrusion, injection molding, calendar articles and for powder slush processes.
  • the carbodiimides according to the invention are preferably used in thermoplastic polyurethanes.
  • the present invention therefore also relates to processes for producing silicon-organic groups, in this document also as silane-modified, i.e. Thermoplastic polyurethane containing silicon-organic groups and crosslinkable TPU obtainable in this way, in particular cable sheaths, fibers or hoses, in particular compressed air hoses, and the corresponding products crosslinked via the silane groups.
  • the invention relates to cable sheathing, fibers or hoses, in particular compressed air hoses, based on thermoplastic polyurethane which is crosslinked via silane groups, in particular siloxane groups, in particular cable sheathing, fibers or hoses in which the crosslinked thermoplastic polyurethane has a Shore-A hardness of between 85 and 98 and a Vicat temperature according to DIN EN ISO 306 (10N / 120 K / h) of greater than 130 ° C, particularly preferably greater than 140 ° C, in particular greater than 145 ° C.
  • TPUs produced according to the invention which are usually present in the form of granules or in powder form, into injection molding and extrusion articles, for example the desired films, moldings, rolls, fibers, linings in automobiles, hoses, cable connectors, bellows, trailing cables, cable jackets, seals , Belts or damping elements are carried out using customary methods, such as Injection molding or extrusion.
  • Injection molding and extrusion articles of this type can also be made from compounds containing the TPU according to the invention and at least one further thermoplastic, in particular a polyethylene, polypropylene, polyester, polyether, polystyrene, PVC, ABS, ASA, SAN, polyacrylonitrile, EVA, PBT, PET, polyoxy- methylene.
  • the TPU produced according to the invention can be used to produce the articles shown at the beginning.
  • the silane-modified thermoplastic polyurethane will preferably be spun into fibers or hoses, in particular compressed air hoses, by generally known methods, and then the thermoplastic polyurethane will be crosslinked via the silane groups by means of moisture, optionally using a catalyst which accelerates the crosslinking.
  • a catalyst which accelerates the crosslinking.
  • the crosslinking reactions above and through the silane groups are familiar to the person skilled in the art and are generally known. This crosslinking is usually carried out by moisture and can be carried out by heat or catalysts known for this purpose, e.g. Lewis acids, Lewis bases,
  • Bronsted acids, Bronsted bases are accelerated.
  • Acetic acid organic metal compounds such as titanium acid esters, iron compounds such as e.g. Iron (III) acetylacetonate, tin compounds e.g. Tin diacetate, tin dioctoate, tin dilaurate or the tin dialkyl salts of aliphatic carboxylic acids such as dibutyl tin diacetate, dibutyl tin dilaurate or the like, particularly preferably tin dilaurate and / or acetic acid.
  • organic metal compounds such as titanium acid esters
  • iron compounds such as e.g. Iron (III) acetylacetonate
  • tin compounds e.g. Tin diacetate, tin dioctoate, tin dilaurate or the tin dialkyl salts of aliphatic carboxylic acids such as dibutyl tin diacetate, dibutyl t
  • the polyols listed in Table 1 were mixed at 1,40 with butanediol.
  • the various hydrolysis protective stabilizers as listed in Table 1 were then added with stirring.
  • Elastostab® H01 polymeric carbodiimide (hydrolysis protection agent) from Elastogran GmbH
  • Stabaxol® 1 monomeric carbodiimide (hydrolysis protection agent) from Rheinchemie GmbH
  • Stabilizer 1 Stabilizer produced in Example 1
  • the glycol mixture was heated to 80 ° C. with stirring.
  • 425 g of 4,4'-MDI methylene diphenyl diisocyanate
  • the mixture was then poured into a flat Teflon dish and annealed at 125 ° C. on a hot plate for 10 minutes.
  • the resulting TPU rind was annealed in a heating cabinet at 100 ° C for 24 h. After the mold plates had been granulated, they were processed into 2 mm spray plates on an injection molding machine. The mechanical values were determined and are listed in Table 2.
  • test specimens were punched out of the spray plates, these were placed in glasses (250 and 500 ml) with distilled water and placed in a temperature control cabinet at a defined temperature (80 ° C.). Three test specimens were removed at certain intervals (e.g. weekly). Then the samples were min. Stored for 30 minutes in standard climate 23/50 and determined tensile strength and elongation at break.

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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

Carbodiimides contenant la structure de formule (I) dans laquelle n représente 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 ou 20, R1 représente un reste aliphatique, cycloaliphatique, araliphatique ou aromatique, éventuellement substitué et éventuellement à chaîne ramifiée, R2 représente un reste aliphatique, cycloaliphatique, araliphatique ou aromatique, éventuellement substitué et éventuellement à chaîne ramifiée, R3 représente méthyl-, éthyl, -O-CH3, -O-CH2-CH3, -O-CH(CH3)2, -O-C(CH3)3 ou -O-CH2-CH2-O-CH3, R4 représente méthyl-, éthyl, -O-CH3, -O-CH2-CH3, -O-CH(CH3)2, -O-C(CH3)3 ou -O-CH2-CH2-O-CH3 et R5 représente méthyl-, éthyl, -O-CH3, -O-CH2-CH3, -O-CH(CH3)2, -O-C(CH3)3 ou -O-CH2-CH2-O-CH3.
PCT/EP2005/004819 2004-05-13 2005-05-04 Carbodiimides contenant des groupes silane Ceased WO2005111106A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE112005000561.5T DE112005000561B4 (de) 2004-05-13 2005-05-04 Carbodiimide enthaltend Silangruppen

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DE200410024195 DE102004024195A1 (de) 2004-05-13 2004-05-13 Carbodiimide enthaltend Silangruppen
DE102004024195.3 2004-05-13

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015178352A1 (fr) * 2014-05-23 2015-11-26 関西ペイント株式会社 Composition de revêtement, article revêtu, et procédé de formation de film de revêtement
FR3125423A1 (fr) 2021-07-23 2023-01-27 L'oreal Composition cosmétique comprenant au moins un composé (poly)carbodiimide et au moins un alcoxysilane aminé

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CA1099844A (fr) * 1976-10-08 1981-04-21 Minnesota Mining And Manufacturing Company Polycarbodiimide terminee par un silane
DE4442722A1 (de) * 1994-12-01 1996-06-05 Basf Ag Schlagzäh thermoplastische Formmassen
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EP0628541A1 (fr) * 1993-06-08 1994-12-14 BASF Aktiengesellschaft Carbodiimides et/ou polycarbodiimides oligomérique à base de 1,3-bis-(1-méthyle-1-isocyanatoéthyl)-benzène, procédé de leur préparation et leur utilisation comme stabilisateurs d'hydrolyse
EP0969029A1 (fr) * 1998-06-05 2000-01-05 Basf Corporation Polycarbodiimides et leur utilisation comme couche intermediaire adhésive dans les peintures pour automobiles
EP1162237A1 (fr) * 2000-06-05 2001-12-12 Rohm And Haas Company Composition de revêtement résistante à l'usure et méthode de production de revêtement

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015178352A1 (fr) * 2014-05-23 2015-11-26 関西ペイント株式会社 Composition de revêtement, article revêtu, et procédé de formation de film de revêtement
JPWO2015178352A1 (ja) * 2014-05-23 2017-04-20 関西ペイント株式会社 塗料組成物、塗装物品及び塗膜形成方法
FR3125423A1 (fr) 2021-07-23 2023-01-27 L'oreal Composition cosmétique comprenant au moins un composé (poly)carbodiimide et au moins un alcoxysilane aminé

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