WO2005111137A1 - Plastiques contenant du carbodiimide - Google Patents

Plastiques contenant du carbodiimide Download PDF

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Publication number
WO2005111137A1
WO2005111137A1 PCT/EP2005/004827 EP2005004827W WO2005111137A1 WO 2005111137 A1 WO2005111137 A1 WO 2005111137A1 EP 2005004827 W EP2005004827 W EP 2005004827W WO 2005111137 A1 WO2005111137 A1 WO 2005111137A1
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WO
WIPO (PCT)
Prior art keywords
carbodiimides
polyurethanes
ethyl
plastics
groups
Prior art date
Application number
PCT/EP2005/004827
Other languages
German (de)
English (en)
Inventor
Markus Krämer
Oliver Steffen Henze
Original Assignee
Basf Aktiengesellschaft
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 Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Publication of WO2005111137A1 publication Critical patent/WO2005111137A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/544—Silicon-containing compounds containing nitrogen
    • C08K5/5465—Silicon-containing compounds containing nitrogen containing at least one C=N bond
    • 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
    • C08G18/28—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
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C08L75/06—Polyurethanes from polyesters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/529—Esters containing heterocyclic rings not representing cyclic esters of phosphoric or phosphorous acids

Definitions

  • thermoplastic plastics particularly preferably polyurethane, in particular thermoplastic polyurethane containing carbodiimide, which has the following structural unit:
  • Ri 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, in particular 3 hydrocarbon atoms,
  • 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, in particular 3 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 3l -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 3l
  • R 5 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 .
  • silane groups means in particular organosilicon 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 polycondensation products such as polyurethanes.
  • 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 plastics based on polyester are described, for example, in DE-A 4 318979, DE-A 4442724 and EP-A 460481.
  • EP-A 969 029, EP-A 785 222, EP-A 507407, 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, in particular polyester-based TPU, 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 Do not adversely affect plastics, in particular polyurethane elastomers.
  • 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 molecular weights 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 by 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:
  • the TPUs produced with the carbodiimides according to the invention have the following advantages over conventional carbodiimides: Improved hydrolytic resistance when stored in water at 80 ° C. Improvement (increase) in tensile strength and elongation at break when stored under water. Crosslinking of the siloxane groups in-situ when used under moist conditions Conditions, ie Eliminate the additional step of cross-linking Reduce the swelling properties Increase the heat resistance ⁇ Increase the HDT Increase the E-mode Increase the Vicat temperature
  • thermoplastics particularly preferably polyurethane, in particular thermoplastic polyurethane containing carbodiimide of the following structure:
  • 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 a generally known isocyanate which has at least one silane group in the presence of catalysts with elimination of carbon dioxide to give the carbodiimide.
  • the carbodiimides according to the invention can be prepared by reacting the isocyanate groups at elevated temperatures, for example at temperatures from 50 to 200 ° C., preferably from 150 to 185 ° C., advantageously in the presence of catalysts be condensed with elimination of carbon dioxide. Methods suitable for this are described, for example, in GB-A-1 083410, DE-B 1 130 594 (GB-A-851 936) and DE-A-11 56401 (US-A-3 502 722).
  • phosphorus compounds which are preferably selected from the group of phospholenes, phospholenoxides, phospholidines and phospholinoxides, have proven to be excellent catalysts.
  • the polycarbodiimide formation is usually terminated.
  • the catalysts can be distilled off under reduced pressure or deactivated by adding a deactivator, such as, for example, phosphorus trichloride.
  • the polycarbodiimide preparation can furthermore be carried out in the absence or presence of solvents which are inert under the reaction conditions.
  • the carbodiimide shown at the outset is preferably obtained.
  • 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, e.g. Polycondensation products such as thermoplastic polyesters such as polyethylene and butylene terephthalate, polyether esters, polyamides, polyester amides, polycaprolactones and unsaturated polyester resins and polyester esters such as e.g. Block copolymers of polyethylene or butylene terephthalate and polycaprolactone. and polyaddition products, e.g.
  • Polycondensation products such as thermoplastic polyesters such as polyethylene and butylene terephthalate, polyether esters, polyamides, polyester amides, polycaprolactones and unsaturated polyester resins and polyester esters such as e.g. Block copolymers of polyethylene or butylene
  • polyurethanes polyureas and polyurethane-polyurea elastomers that contain ester groups. These compounds containing ester groups are generally known. Their starting substances, manufacturing processes, structures and properties are described in various ways in the standard literature. Because of the good solubility in the structural components for the production of polyurethanes and the good compatibility with the polyurethanes formed, the (poly) carbodiimides according to the invention are particularly suitable as stabilizers against the hydrolytic degradation of polyurethanes, preferably compact or cellular polyurethane elastomers and in particular thermoplastic polyurethanes and cellular ones 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 mix. In individual cases, depending on the stress of the
  • 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 can be 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 In the presence of additional aids and additives, reacted.
  • 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 preferred in the production of polyurethanes, e.g. cellular, for example microcellular polyurethanes, preferably polyurethane elastomers, in particular thermoplastic polyurethanes.
  • polyurethanes e.g. cellular, for example microcellular polyurethanes, preferably polyurethane elastomers, in particular thermoplastic polyurethanes.
  • the production of these polyurethanes, in particular polyurethane elastomers can be carried out by known reaction of conventional starting components, i.e. Isocyanates, compounds reactive toward isocyanates, optionally blowing agents, preferably water and optionally catalysts, auxiliaries and / or additives are carried out 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.
  • Processes for the production of polyurethanes, preferably thermoplastic polyurethanes, preferably by reacting isocyanates, compounds which are reactive toward isocyanates, optionally blowing agents and, if appropriate, are thus preferred Catalysts, auxiliaries and / or additives, 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 methods 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 also 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 is a sho A hardness 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 plugs, bellows, trailing cables, cable jackets, seals, belts or damping elements is carried out according to 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 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, where appropriate a catalyst which accelerates the crosslinking is used.
  • crosslinking reactions above and through the silane groups are familiar to the person skilled in the art and are generally known.
  • This crosslinking usually takes place by means of moisture and can be accelerated by heat or by catalysts known for this purpose, for example Lewis acids, Lewis bases, Bronsted acids, Bronsted bases.
  • Preferably used as the catalyst for the crosslinking preferably by means of moisture, acetic acid, organic metal compounds such as titanium acid esters, iron compounds such as iron (III) acetyl acetonate, tin compounds such as tin diacetate, tin dioctoate, tin dilaurate or the tin dialkyl salts of aliphatic carboxylic acids such as dibutilyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibutyl dibut
  • the polyols listed in Table 1 were mixed with 1,4-butanediol at 80 ° C.
  • the various hydrolysis 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. Then 425 g of 4,4'-MDI (methylene diphenyl diisocyanate) were added and the mixture was stirred until the reaction mixture was homogeneous. 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. 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 controlled cabinet at a defined temperature (80 ° C). Three test specimens were removed at certain intervals (eg weekly). Then the samples were min. Stored for 30 minutes in standard climate 23/50 and determined tensile strength and elongation at break. Table 4:

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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)

Abstract

Plastiques contenant du carbodiimide qui présente l'unité structurale (I), dans laquelle 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/EP2005/004827 2004-05-13 2005-05-04 Plastiques contenant du carbodiimide WO2005111137A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004024204.6 2004-05-13
DE200410024204 DE102004024204A1 (de) 2004-05-13 2004-05-13 Kunststoffe enthaltend Carbodiimid

Publications (1)

Publication Number Publication Date
WO2005111137A1 true WO2005111137A1 (fr) 2005-11-24

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WO (1) WO2005111137A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2803660A1 (fr) * 2013-05-13 2014-11-19 Rhein Chemie Rheinau GmbH Nouveaux carbodiimides comprenant des groupes urée et/ou uréthane à terminaison, leur procédé de fabrication et leur utilisation
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

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4118536A (en) * 1976-10-08 1978-10-03 Minnesota Mining And Manufacturing Company Silane-terminated polycarbodiimide primers and composite coatings therefrom
EP0507407A1 (fr) * 1991-04-03 1992-10-07 Stahl Holland B.V. Agents de réticulation multifonctionnelle et dispersible dans l'eau
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

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4118536A (en) * 1976-10-08 1978-10-03 Minnesota Mining And Manufacturing Company Silane-terminated polycarbodiimide primers and composite coatings therefrom
EP0507407A1 (fr) * 1991-04-03 1992-10-07 Stahl Holland B.V. Agents de réticulation multifonctionnelle et dispersible dans l'eau
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 (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2803660A1 (fr) * 2013-05-13 2014-11-19 Rhein Chemie Rheinau GmbH Nouveaux carbodiimides comprenant des groupes urée et/ou uréthane à terminaison, leur procédé de fabrication et leur utilisation
WO2014184116A1 (fr) * 2013-05-13 2014-11-20 Rhein Chemie Rheinau Gmbh Nouveaux carbodiimides portant des groupes urée et/ou uréthane terminaux, procédés pour les préparer et leur utilisation
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

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Publication number Publication date
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