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EP1311636A2 - Melanges caoutchoutes contenant des isocyanatosilanes et des microgels - Google Patents

Melanges caoutchoutes contenant des isocyanatosilanes et des microgels

Info

Publication number
EP1311636A2
EP1311636A2 EP01958017A EP01958017A EP1311636A2 EP 1311636 A2 EP1311636 A2 EP 1311636A2 EP 01958017 A EP01958017 A EP 01958017A EP 01958017 A EP01958017 A EP 01958017A EP 1311636 A2 EP1311636 A2 EP 1311636A2
Authority
EP
European Patent Office
Prior art keywords
rubber
weight
gel
parts
gels
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Withdrawn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
EP01958017A
Other languages
German (de)
English (en)
Inventor
Werner Obrecht
Martin Mezger
Anthony Sumner
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.)
Lanxess Deutschland GmbH
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP1311636A2 publication Critical patent/EP1311636A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L19/00—Compositions of rubbers not provided for in groups C08L7/00 - C08L17/00
    • C08L19/006—Rubber characterised by functional groups, e.g. telechelic diene polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B60—VEHICLES IN GENERAL
    • B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
    • B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B60—VEHICLES IN GENERAL
    • B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
    • B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
    • B60C1/0016—Compositions of the tread
    • 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
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L21/00—Compositions of unspecified rubbers
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L15/00—Compositions of rubber derivatives
    • C08L15/005—Hydrogenated nitrile rubber
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/16—Ethene-propene or ethene-propene-diene copolymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L7/00—Compositions of natural rubber
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
    • C08L9/02—Copolymers with acrylonitrile
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
    • C08L9/06—Copolymers with styrene

Definitions

  • the invention relates to rubber mixtures which contain microgels and isocyanatosilanes and to vulcanizates produced therefrom.
  • the addition of the isocyanatosilanes improves the mechanical properties of the vulcanizates, in particular the stretching properties and the abrasion resistance, without reducing the difference between the rebound elasticities at 70 ° C. and 23 ° C.
  • crosslinked rubber particles in rubber compounds is among others described in the following patents and patent applications: US-A 5 124 408 (sulfur-modified CR gels), US-A 5 395 891 (BR gels), DE-A 19 726 729 (SBR gels) and DE patent application 19 701 487.9 (NBR gels).
  • US-A 5 124 408 sulfur-modified CR gels
  • US-A 5 395 891 BR gels
  • SBR gels DE-A 19 726 729
  • NBR gels DE patent application 19 701 487.9
  • the vulcanizates produced therefrom are particularly suitable for the production of rubber articles and tire components such as tire treads.
  • Vulcanizates with rubber gels in particular, based on CR, SBR and NBR microgels have high rebound resilience at 70 ° C and thus low rolling resistance, and low rebound resilience at 23 ° C and thus high wet slip resistance.
  • the difference in rebound elasticities between 70 ° C and 23 ° C is characteristic of rubber compounds that contain these microgels.
  • the mechanical properties of the microgel-containing vulcanizates are not sufficient for use in technical rubber articles and in tire components. Deficits exist particularly in the level of mechanical vulcanizate properties. There is therefore a need to improve the stress value at 300% elongation and elongation at break as well as the abrasion resistance.
  • the task was therefore to determine the mechanical value level (product of the stress value at 300% elongation and elongation at break) and the abrasion resistance
  • the invention therefore relates to rubber mixtures containing at least one double bond-containing rubber (A), at least one microgel (B) and at least one isocyanatosilane (C), the proportion of double bond-containing rubber (A) being 100 parts by weight and the proportion of rubber gel (B ) 1 to 150% by weight
  • Parts preferably 10 to 20 parts by weight, and the proportion of isocyanatosilane (C) 0.2 to 20 parts by weight, preferably 1 to 10 parts by weight, and further rubber auxiliaries and fillers.
  • Double-bonded rubber means the rubbers which are referred to as R rubbers according to DLN / ISO 1629. These rubbers have a double bond in the main chain. These include, for example:
  • SBR styrene / butadiene rubber
  • BR polybutadiene rubber
  • NBR nitrile rubber
  • HNBR hydrogenated nitrile rubber
  • SNBR styrene / butadiene / acrylonitrile rubber
  • CR polychloroprene
  • XSBR carboxylated styrene / butadiene rubber
  • XNBR carboxylated butadiene / acrylonitrile rubber
  • ENR epoxidized natural rubber
  • ESBR epoxidized styrene / butadiene rubber
  • rubbers containing double bonds are also to be understood to mean rubbers which are M rubbers in accordance with DIN / ISO 1629 and in addition to the saturated rubbers
  • Main chain have double bonds in side chains. This includes e.g. EPDM.
  • NR NR
  • BR BR
  • SBR SBR
  • SNBR SNBR
  • IIR IIR
  • EPDM EPDM
  • Crosslinked rubber particles (B), also referred to as rubber gels or microgels, are described, for example, in US Pat. No. 5,124,408, US Pat. No. 5,395,891, DE-A
  • Rubber rubbers with functional groups with acidic hydrogen which are mixed with alkoxysilane are preferred. NEN or reacts with isocyanates. Preferred functional groups are hydroxyl groups, carboxyl groups, amino groups or amido groups.
  • Rubber gels are: BR, NR, NBR, CR and / or SBR gels which are optionally equipped with groups on the surface of the gels and which are able to react with the isocyanatosilanes.
  • groups are, for example, the functional groups mentioned above.
  • a rubber gel which is hydroxyl-modified can be used particularly advantageously, the acrylates and methacrylates of
  • Hydroxyethanol, hydroxypropanol and hydroxybutanol can be used.
  • the amount of hydroxylating agent is 0.1 to 50 phr based on the unmodified rubber gel. 0.5 to 20 phr are particularly preferred. Hydroxybutyl acrylate is particularly preferably used in amounts of 0.5 to 20 phr for the hydroxyl modification.
  • the microgels have particle diameters of 5-1000 n, preferably 20-600 nm (D VN value according to DIN 53206).
  • the diameter specifications d_o, d 50 and d 80 denote characteristic diameters in which 10, 50 and 80 parts by weight of the sample each have a diameter which is smaller than the corresponding characteristic diameter.
  • the particle diameter is determined by means of ultracentrifugation.
  • the rubber gels are insoluble and suitable
  • Swelling agents such as toluene swellable.
  • the gel content of the rubber gels is> 80% by weight.
  • the swelling indices of the microgels (QI) in toluene are 1-50, preferably 1-20.
  • the gel content and swelling index (QI) of the rubber gels are determined by extracting the sample with toluene at room temperature.
  • the gel content indicates the percentage by weight of the portion which sediments and can be separated off in toluene when centrifuged at 20,000 rpm.
  • the swelling index is calculated from the weight of the solvent-containing gel (after centrifugation at 20,000 rpm) and the weight of the dry gel:
  • the glass transition temperature (Tg) of the rubber gels is between -70 ° C and + 10 ° C. It is determined using DSC (Differential Scanning Calorimetry) (e.g. calorimeter
  • Tg 11.6 + 0.3 mg substance are used in normal capsules. Two heats are carried out, each from -100 ° C to + 150 ° C at a heating rate of 20K / min and a cooling rate of 320 IC / min with nitrogen flushing. The glass temperatures are determined during the 2nd DS C heating.
  • the isocyanatosilanes (C) have the following basic structure:
  • R 1 , R 2 and R 3 represent alkoxy groups with 1 to 12 C atoms, preferably 1 to 8 C atoms, and can be the same or different and Q represents a spacer group with structural elements based on aliphatic, heteroaliphatic, aromatic and heteroaromatic carbon chains.
  • R 1 , R 2 and R 3 are preferably methoxy, ethoxy, propoxy and butoxy groups and Q is methyl, ethyl, propyl, butyl, pentyl and hexyl groups.
  • the preferred isocyanatoalkoxysilane is gamma-isocyanatopropyltriethoxysilane of the following formula:
  • This product is e.g. commercially available from Witco under the name Silquest A-1310 Silane.
  • the rubber mixtures according to the invention can contain additional further components such as fillers.
  • Particularly suitable fillers for the production of the rubber mixtures and vulcanizates according to the invention are:
  • the carbon blacks to be used here are produced by the soot, furnace or gas black process and have BET surface areas of 20-200 m 2 / g such as: S AF-IS AF, IIS AF, HAF, FEF or GPF - Russian.
  • silica produced for example by precipitation of solutions of silicates or Flammliydrolse of silicon halogens with specific surface areas of 5-1000, preferably 20-400 m 2 / g (BET surface area) and primary particle sizes of 5-400 nm.
  • the silicas can optionally also be mixed oxides with other metal oxides, such as Al, Mg , Ca, Ba, Zn and Ti oxides are present.
  • Synthetic silicates such as aluminum silicate, alkaline earth metal silicate, such as magnesium silicate or calcium silicate with BET surface areas of 20-400 m 2 / g and primary particle diameters of 5-400 nm.
  • Metal oxides such as zinc oxide, calcium oxide, magnesium oxide, aluminum oxide.
  • Metal carbonates such as calcium carbonate, magnesium carbonate, zinc carbonate.
  • Metal sulfates such as calcium sulfate, barium sulfate.
  • Metal hydroxides such as aluminum hydroxide and magnesium hydroxide.
  • thermoplastics such as trans-l, 4-polybutadiene, syndiotactic 1,2-polybutadiene, polybutylene and polyethylene terephthalate or syndiotactic polystyrene.
  • Thermoplastics with high glass transition temperature such as polyamides, polyphenylene sulf ⁇ d, or polycarbonates.
  • Glass fibers and glass fiber products fibers, strands or micro glass balls.
  • - Thermoplastic fibers polyamide, polyester, aramid.
  • the fillers mentioned can be used alone or in a mixture.
  • the amount of the fillers is usually 5 to 200 parts by weight, based on 100
  • Parts by weight of rubber Parts by weight of rubber.
  • 10-100 parts by weight of rubber gel (B), together with 0.1-100 parts by weight of carbon black and / or 0.1-100 parts by weight of light fillers, are used, based in each case on 100 parts by weight of non-crosslinked rubber. If a mixture of carbon black and light fillers is used, the total amount is a maximum of 100
  • the rubber mixtures according to the invention can contain further rubber auxiliaries, such as crosslinking agents, reaction accelerators, anti-aging agents, heat stabilizers, light stabilizers, ozone protection agents, processing aids, plasticizers, tackifiers, blowing agents, dyes, pigments, wax, extenders, organic acids, retarders, metal oxides and filler activators, such as for example triethanolamine, polyethylene glycol, hexanetriol, bis (triethoxisilylpropyl) tetrasulfide or other auxiliaries known in the rubber industry.
  • auxiliaries such as crosslinking agents, reaction accelerators, anti-aging agents, heat stabilizers, light stabilizers, ozone protection agents, processing aids, plasticizers, tackifiers, blowing agents, dyes, pigments, wax, extenders, organic acids, retarders, metal oxides and filler activators, such as for example triethanolamine, polyethylene glycol, hexanetriol, bis (triethoxisilyl
  • the rubber auxiliaries mentioned are in conventional amounts, which u. a. according to the intended use. Common amounts are e.g. Amounts of 0.1-50 percent by weight, based on the amounts of rubber (A) used.
  • Cross-linking agents such as sulfur, sulfur donors, peroxides or cross-linking agents such as diisopropenylbenzene, divinylbenzene, divinyl ether, divinyl sulfone, diallyl phthalate, triallyl cyanurate, triallyl isocyanurate, 1,2-polybutadiene, N, N'-m-phenylene-maleimide and / or Triallyl trimellitate can be used.
  • cross-linking agents such as sulfur, sulfur donors, peroxides or cross-linking agents such as diisopropenylbenzene, divinylbenzene, divinyl ether, divinyl sulfone, diallyl phthalate, triallyl cyanurate, triallyl isocyanurate, 1,2-polybutadiene, N, N'-m-phenylene-maleimide and / or Triallyl trimellitate can be used.
  • the acrylates and methacrylates of polyvalent, preferably 2 to 4-valent C to C 10 alcohols such as ethylene glycol, propanediol-1, 2, butanediol, hexanediol, polyethylene glycol with 2 to 20, preferably 2 to 8, oxy- ethylene units, neopentyl glycol, bisphenol-A, glycerol, trimethyl propane, pentaerythritol, sorbitol with unsaturated polyesters from aliphatic di- and polyols as well as maleic acid, fumaric acid and / or itaconic acid.
  • the amount of crosslinking agent or crosslinking agent is generally 1 to 30 parts by weight, based on 100 parts by weight of the monomers.
  • the rubber mixtures according to the invention can also contain vulcanization accelerators.
  • suitable vulcanization accelerators are e.g. Mercaptobenzthiazoles, -sulfenamides, guanidines, thiurams, dithiocarbamates, thioureas and thiocarbonates.
  • the rubber mixtures according to the invention can be vulcanized at temperatures of 100-250 ° C., preferably 130-180 ° C., if appropriate under a pressure of 10-200 bar.
  • the mixtures according to the invention can be prepared in various ways.
  • the solid individual components it is of course possible to mix the solid individual components. Suitable units for this are, for example, roller, internal mixer or mixing extruder. However, mixing by combining the latices of the uncrosslinked or crosslinked rubbers is also possible.
  • the mixture according to the invention thus prepared can be isolated, as usual, by evaporation, precipitation or freeze coagulation (cf. US Pat. No. 2,187,146). By mixing fillers into the latex mixture and subsequent working up, the mixtures according to the invention can be obtained directly as a rubber / filler formulation.
  • Double bond-containing rubber (A), rubber gel (B) and isocyantosilane (C) such as additional fillers and, if appropriate, rubber auxiliaries, are carried out in conventional mixing units, rollers, internal mixers or also mixing extruders.
  • the mixing temperatures are around 50-180 ° C.
  • the rubber mixtures according to the invention are suitable for the production of vulcanized moldings, for example for the production of cable jackets, hoses, drive belts, conveyor belts, roller coverings, shoe soles, sealing rings, damping elements or membranes and for various tire components such as tire treads, sub-tread mixtures, carcasses or Sidewall inserts for tires with run-flat properties.
  • Gel 1 The preparation is carried out as described in US Pat. No. 5,395,891, 1.0 phr (parts per one hundred parts of rubber) being used for crosslinking with dicumyl peroxide.
  • Gel 3 The polymerization of the starting BR latex is carried out as described in US Pat. No. 5,395,891. Networking with DCP, grafting with HEMA and processing are described in the above DE application.
  • Gel 4 is prepared analogously to gel 3, with hydroxybutyl acrylate (HB A) being used instead of hydroxyethyl methacrylate (HEMA) for the hydroxyl modification.
  • HB A hydroxybutyl acrylate
  • HEMA hydroxyethyl methacrylate
  • the mixture components are mixed on the roller in the specified order according to the following recipes:
  • Vulkacit® NZ and Silquest® A-1310 silanes are mixed in on the roller.
  • the mixtures are vulcanized in the press at 160 ° C.
  • the first series of mixtures shows that the use of ⁇ -isocyanatopropyltriethoxysilane improves the mechanical properties of both a non-hydroxyl-modified BR gel (Gell) and a hydroxymodified SBR gel (Gel 2) (p 3 oo x D) is achieved.
  • characteristic information such as F m i n, F m ax.-Fn_in-, tio, t 80 and t o 9 determined .:
  • the mixtures are vulcanized in the press at 160 ° C.

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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)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne des mélanges caoutchoutés, contenant des microgels et des isocyanatosilanes, ainsi que des vulcanisats obtenus à partir de ces mélanges. En ajoutant des isocyanatosilanes, on améliore les propriétés mécaniques de ces vulcanisats, en particulier les propriétés d'allongement et la résistance à l'usure, sans réduire la différence des élasticités de rebondissement à 70 DEG C et 23 DEG C.
EP01958017A 2000-08-08 2001-07-25 Melanges caoutchoutes contenant des isocyanatosilanes et des microgels Withdrawn EP1311636A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10038488 2000-08-08
DE10038488A DE10038488A1 (de) 2000-08-08 2000-08-08 Isocyanatosilan- und mikrogelhaltige Kautschukmischungen
PCT/EP2001/008585 WO2002012389A2 (fr) 2000-08-08 2001-07-25 Melanges caoutchoutes contenant des isocyanatosilanes et des microgels

Publications (1)

Publication Number Publication Date
EP1311636A2 true EP1311636A2 (fr) 2003-05-21

Family

ID=7651594

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01958017A Withdrawn EP1311636A2 (fr) 2000-08-08 2001-07-25 Melanges caoutchoutes contenant des isocyanatosilanes et des microgels

Country Status (11)

Country Link
US (1) US6632888B2 (fr)
EP (1) EP1311636A2 (fr)
JP (1) JP2004506058A (fr)
KR (1) KR100684251B1 (fr)
AU (1) AU2001279783A1 (fr)
BR (1) BR0113047A (fr)
CA (1) CA2418354A1 (fr)
DE (1) DE10038488A1 (fr)
MX (1) MXPA03001185A (fr)
TW (1) TW574293B (fr)
WO (1) WO2002012389A2 (fr)

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DE10038488A1 (de) 2002-02-21
TW574293B (en) 2004-02-01
WO2002012389A3 (fr) 2002-04-18
KR20030024845A (ko) 2003-03-26
CA2418354A1 (fr) 2003-02-05
AU2001279783A1 (en) 2002-02-18
WO2002012389A2 (fr) 2002-02-14
MXPA03001185A (es) 2004-04-02
JP2004506058A (ja) 2004-02-26
US6632888B2 (en) 2003-10-14
US20020049282A1 (en) 2002-04-25
BR0113047A (pt) 2003-07-01

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