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WO2005080493A1 - Reticulation de polymeres nitriles carboxylates au moyen de composes possedant au moins deux groupes epoxy - Google Patents

Reticulation de polymeres nitriles carboxylates au moyen de composes possedant au moins deux groupes epoxy Download PDF

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Publication number
WO2005080493A1
WO2005080493A1 PCT/CA2005/000256 CA2005000256W WO2005080493A1 WO 2005080493 A1 WO2005080493 A1 WO 2005080493A1 CA 2005000256 W CA2005000256 W CA 2005000256W WO 2005080493 A1 WO2005080493 A1 WO 2005080493A1
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WO
WIPO (PCT)
Prior art keywords
compound
polymer
epoxidized
carboxylated nitrile
hydrogenated
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.)
Ceased
Application number
PCT/CA2005/000256
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English (en)
Inventor
Frederic Guerin
Carl Walter Von Hellens
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.)
Arlanxeo Canada Inc
Original Assignee
Lanxess Inc
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Filing date
Publication date
Application filed by Lanxess Inc filed Critical Lanxess Inc
Publication of WO2005080493A1 publication Critical patent/WO2005080493A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • C08K5/04—Oxygen-containing compounds
    • C08K5/15—Heterocyclic compounds having oxygen in the ring
    • C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
    • C08K5/1515—Three-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins

Definitions

  • the present invention relates to a polymer compound comprising at least one carboxylated nitrile rubber polymer, that is optionally hydrogenated, at least one epoxidized compound having at least two epoxide functions and at least one filler, a method of inducing curing in a compound comprising at least one carboxylated nitrile rubber polymer, that is optionally hydrogenated, by addition of at least one epoxidized compound having at least two epoxide functions and subsequent curing.
  • Carboxylated hydrogenated nitrile rubber prepared by the selective hydrogenation of carboxylated acrylonitrile-butadiene rubber (nitrile rubber; XNBR, a co-polymer comprising at least one conjugated diene, at least one unsaturated nitrile, at least one carboxylated monomer and optionally further comonomers), is a specialty rubber which has very good heat resistance, excellent ozone and chemical resistance, and excellent oil resistance.
  • XNBR and HXNBR have found widespread use in the automotive (seals, hoses, bearing pads) oil (stators, well head seals, valve plates), electrical (cable sheating), mechanical engineering (wheels, rollers) and shipbuilding (pipe seals, couplings) industries, amongst others.
  • the present invention relates to a polymer compound comprising at least one carboxylated nitrile polymer, that is optionally hydrogenated, at least one epoxidized compound having at least two epoxide functions and at least one filler. It is preferred that the XNBR is fully or partially hydrogenated ("HXNBR").
  • the invention relates to a polymer compound comprising at least one carboxylated nitrile polymer, that is optionally hydrogenated, at least one epoxidized compound having at least two epoxide functions and at least one filler that comprises no further cross-linking agent, such as peroxides, sulphur, sulphur compounds, and the like.
  • Fig 1. shows for the compounds of examples 1-3 the torque (S') in dN.m for the first hour of curing at 1 ° arc and 180°C.
  • the term "carboxylated nitrile polymer" or XNBR is intended to have a broad meaning and is meant to encompass an elastomer having repeating units derived from at least one conjugated diene, at least one alpha-beta-unsaturated nitrile, at least one monomer having a carboxylic group and optionally further one or more copolymerizable monomers.
  • the conjugated diene may be any known conjugated diene, in particular a C4-C 6 conjugated diene.
  • Preferred conjugated dienes are butadiene, isoprene, piperylene, 2,3-dimethyl butadiene and mixtures thereof.
  • C 4 -C 6 conjugated dienes are butadiene, isoprene and mixtures thereof.
  • the most preferred C 4 -C 6 conjugated diene is butadiene.
  • the alpha-beta-unsaturated nitrile may be any known alpha-beta- unsaturated nitrile, in particular a C3-C5 alpha-beta-unsaturated nitrile.
  • Preferred C 3 -C 5 alpha-beta-unsaturated nitriles are acrylonitrile, methacrylonitrile, ethacrylonitrile and mixtures thereof.
  • the most preferred C 3 - C 5 alpha-beta-unsaturated nitrile is acrylonitrile.
  • the monomer having at least one carboxylic group may be any known monomer having at least one carboxylic group being copolymerizable with the nitrile and the diene.
  • Preferred monomers having at least one carboxylic group are unsaturated carboxylic acids.
  • suitable unsaturated carboxylic acids are fumaric acid, maleic acid, acrylic acid, methacrylic acid and mixtures thereof.
  • the copolymer comprises in the range of from 40 to 85 weight percent of repeating units derived from one or more conjugated dienes, in the range of from 15 to 60 weight percent of repeating units derived from one or more unsaturated nitriles and in the range of from 0.1 to 15 weight percent of repeating units derived from one or more monomers having at least one carboxylic group. More preferably, the copolymer comprises in the range of from 55 to 75 weight percent of repeating units derived from one or more conjugated dienes, in the range of from 25 to 40 weight percent of repeating units derived from one or more unsaturated nitriles and in the range of from 1 to 7 weight percent of repeating units derived from one or more monomers having at least one carboxylic group.
  • the copolymer may further comprise repeating units derived from one or more copolymerizable monomers, such as alkylacrylate, styrene.
  • repeating units derived from one or more copolymerizable monomers will replace either the nitrile or the diene portion of the nitrile rubber and it will be apparent to the skilled in the art that the above mentioned figures will have to be adjusted to result in 100 weight percent. Hydrogenated in this invention is preferably understood by more than
  • the present invention is not restricted to a special process for preparing the hydrogenated carboxylated NBR.
  • the HXNBR preferred in this invention is readily available as disclosed in WO-01/77185-A1.
  • WO-01/77185-A1 is incorporated herein by reference.
  • the XNBR as well as the HXNBR which forms a preferred component of the polymer compound of the invention can be characterized by standard techniques known in the art.
  • the molecular weight distribution of the polymer was determined by gel permeation chromatography (GPC) using a Waters 2690 Separation Module and a Waters 410 Differential Refractometer running Waters Millennium software version 3.05.01. Samples were dissolved in tetrahydrofuran (THF) stabilized with 0.025% BHT. The columns used for the determination were three sequential mixed-B gel columns from Polymer Labs. Reference Standards used were polystyrene standards from American Polymer Standards Corp.
  • the inventive polymer compound further comprises at least one epoxidized compound having at least two or more epoxide functions.
  • the epoxidized compound having at least two epoxide functions is not restricted and any known epoxidized compound having two or more epoxide functions that under the conditions typically used for rubber curing is capable of reacting with the carboxylic group(s) of the monomer having at least one carboxylic group is suitable.
  • Non-limiting examples are epoxidized mineral oils, epoxidized fatty acids, epoxidized oils from natural sources, epoxidized derivatives of fatty acid glycerides which are prepared from the corresponding oils and fats by methods known in the art.
  • Suitable epoxidized fatty acid glycerides include epoxidized soy bean oil (ESBO), epoxidized linseed oil, epoxidized corn oil, epoxidized coconut oil, epoxidized cottonzeed oil, epoxidized olive oil, epoxidized palm oil, epoxidized palm kernel oil, epoxidized peanut oil, epoxidized codliver oil, epoxidized tung oil, epoxidized beef tallow oil, epoxidized butter as well as epoxy resins, glycidyl epoxides, and non- glycidyl epoxides and mixtures thereof.
  • DGEBA diglycidyl ethers of bisphenol-A
  • the inventive polymer compound further comprises at least one filler.
  • the filler may be an active or an inactive filler or a mixture thereof.
  • the filler may be in particular: - highly dispersed silicas, prepared e.g. by the precipitation of silicate solutions or the flame hydrolysis of silicon halides, with specific surface areas of in the range of from 5 to 1000 m 2 /g, and with primary particle sizes of in the range of from 10 to 400 nm; the silicas can optionally also be present as mixed oxides with other metal oxides such as those of Al, Mg, Ca, Ba, Zn, Zr and Ti; - synthetic silicates, such as aluminum silicate and alkaline earth metal silicate like magnesium silicate or calcium silicate, with BET specific surface areas in the range of from 20 to 400 m 2 /g and primary particle diameters in the range of from 10 to 400 nm; - natural silicates, such as kaolin and other naturally occurring silica; - glass fibers and glass fiber products (matting, extrudates) or glass microspheres; -
  • preferred mineral fillers include silica, silicates, clay such as bentonite, gypsum, alumina, titanium dioxide, talc, mixtures of these, and the like. These mineral particles have hydroxyl groups on their surface, rendering them hydrophilic and oleophobic. This exacerbates the difficulty of achieving good interaction between the filler particles and the rubber.
  • the preferred mineral is silica, especially silica made by carbon dioxide precipitation of sodium silicate.
  • Dried amorphous silica particles suitable for use in accordance with the invention may have a mean agglomerate particle size in the range of from 1 to 100 microns, preferably between 10 and 50 microns and most preferably between 10 and 25 microns.
  • a suitable amorphous dried silica moreover usually has a BET surface area, measured in accordance with
  • Suitable silica fillers are available under the trademarks HiSil® 210, HiSil® 233 and HiSil® 243 from PPG Industries Inc. Also suitable are Vulkasil® S and Vulkasil® N, from Bayer AG. Often, use of carbon black as a filler is advantageous.
  • carbon black is present in the polymer composite in an amount of in the range of from 20 to 200 parts by weight, preferably 30 to 150 parts by weight, more preferably 40 to 100 parts by weight.
  • carbon black and mineral filler it might be advantageous to use a combination of carbon black and mineral filler in the inventive polymer composite.
  • the ratio of mineral fillers to carbon black is usually in the range of from 0.05 to 20, preferably 0.1 to 10.
  • the rubber composition according to the invention can contain further auxiliary products for rubbers, such as reaction accelerators, vulcanizing accelerators, vulcanizing acceleration auxiliaries, antioxidants, foaming agents, anti-aging agents, heat stabilizers, light stabilizers, ozone stabilizers, processing aids, plasticizers, tackifiers, blowing agents, dyestuffs, pigments, waxes, extenders, organic acids, inhibitors, metal oxides, and activators such as triethanolamine, polyethylene glycol, hexanetriol, etc., which are known to the rubber industry.
  • the rubber aids are used in conventional amounts, which depend inter alia on the intended use. Conventional amounts are e.g. from 0.1 to 50 wt.%, based on rubber.
  • the composition comprises in the range of 0.1 to 20 phr of an organic fatty acid as an auxiliary product, preferably a unsaturated fatty acid having one, two or more carbon double bonds in the molecule which more preferably includes 10% by weight or more of a conjugated diene acid having at least one conjugated carbon-carbon double bond in its molecule.
  • those fatty acids have in the range of from 8-22 carbon atoms, more preferably 12-18. Examples include stearic acid, palmitic acid and oleic acid and their calcium-, zinc-, magnesium-, potassium- and ammonium salts.
  • the composition comprises in the range of 5 to 50 phr of an acrylate as an auxiliary product.
  • Suitable acrylates are known from EP-A1-0 319 320, in particular p. 3, I. 16 to 35, from US- 5 208 294, in particular Col. 2, I. 25 to 40, and from US-4 983 678, in particular Col. 2, I. 45 to 62.
  • Particular reference is made to zinc acrylate, zinc diacrylate or zinc dimethacrylate or a liquid acrylate, such as trimethylolpropanetrimethacrylate (TRIM), butanedioldimethacrylate (BDMA) and ethylenglycoldimethacrylate (EDMA). It might be advantageous to use a combination of different acrylates and/or metal salts thereof.
  • TAM trimethylolpropanetrimethacrylate
  • BDMA butanedioldimethacrylate
  • EDMA ethylenglycoldimethacrylate
  • metal acrylates in combination with a Scorch-retarder such as sterically hindered phenols (e.g. methyl-substituted aminoalkylphenols, in particular 2,6-di-tert.-butyl-4-dimethylaminomethylphenol).
  • a Scorch-retarder such as sterically hindered phenols (e.g. methyl-substituted aminoalkylphenols, in particular 2,6-di-tert.-butyl-4-dimethylaminomethylphenol).
  • the ingredients of the final polymer composite are mixed together, suitably at an elevated temperature that may range from 25 °C to 200 °C. Normally the mixing time does not exceed one hour and a time in the range from 2 to 30 minutes is usually adequate.
  • the mixing is suitably carried out in an internal mixer such as a Banbury mixer, or a Haake or Brabender miniature internal mixer.
  • a two-roll mill mixer also provides a good dispersion of the additives within the elastomer.
  • scorch pre-crosslinking
  • the invention provides a composition comprising at least one carboxylated nitrile rubber polymer, that is optionally hydrogenated, at least one epoxidized compound having at least two epoxide functions and at least one filler.
  • the inventive polymer compound may be used in the manufacture of a shaped article comprising said inventive polymer compound.
  • Preferred shaped articles are a seal, hose, bearing pad, stator, well head seal, valve plate, cable sheating, wheel roller, pipe seal, in place gaskets or footwear component prepared by injection molding technology.
  • the inventive polymer composite is very well suited for wire and cable production.
  • Examples 1 - 3 Polymer composites were mixed in a brabender miniature internal mixer in a single mixing step (8min/30°C/80 rpm). Composites can also be prepared by mill mixing. The formulations used in this assessment are based on a recipe according to Table 1.
  • Example 3 is comparative. Table 1. Compounding Recipe.
  • Example 1 Example 2 Comp. 3
  • ArmeenTM 18D is an octadecylamine available from AkzoNobel and is used to reduce compound stickiness to metal.
  • THERBANTM XTTM 8889 is HXNBR from Bayer AG.
  • NaugardTM 445 (p-dicumyl diphenyl amine) is a stabilizer from Uniroyal.
  • Plasthall TOTMTM Trioctyl Trimellitate
  • DiakTM 7 Triallyl isocyanurate
  • StruktolTM ZP 1014 zinc peroxide 50% on inert carrier
  • Vulcup 40 KE ( ⁇ , ⁇ -bis(t-butylperoxy)diisopropylbenzene), 40% peroxide.
  • the epoxidized molecule used as curing agent is EPONTM 828, a liquid epoxy resin produced from bisphenol-A and epichlorohydrin and is available from Resolution Performance Products.
  • Polymer Composites Properties Table 2 shows a summary of the properties of polymer composites of Exp. 1-3. MDR Cure Properties (180°C, 1° arc, 1.7 Hz, 60 minutes)
  • Example 1 Comp. 3 Maximum Torque (MH, dN.m) 44.19 57.50 35.29 Minimum Torque (ML, dN.m) 1.10 0.83 1.62 Delta MH-ML (dN.m) 43.09 56.67 33.67
  • the Delta MH-ML gives an indication of the crosslinking density and it increases as a function of epoxy resin content.

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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)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention concerne un composé polymère comprenant au moins un polymère de caoutchouc nitrile carboxylaté, éventuellement hydrogéné, au moins un composé époxydisé doté d'au moins deux fonctions époxyde et au moins une charge. L'invention concerne également un procédé propre à induire une polymérisation dans un composée comprenant au moins un polymère de caoutchouc nitrile carboxylaté, éventuellement hydrogéné, par adjonction d'au moins un composé époxydé doté d'au moins deux fonctions époxyde, suivie de durcissement.
PCT/CA2005/000256 2004-02-23 2005-02-22 Reticulation de polymeres nitriles carboxylates au moyen de composes possedant au moins deux groupes epoxy Ceased WO2005080493A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CA2,458,752 2004-02-23
CA 2458752 CA2458752A1 (fr) 2004-02-23 2004-02-23 Reticulation de polymeres carboxyles du type nitrile a l'aide de composes contenant au moins deux groupes epoxy

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WO2005080493A1 true WO2005080493A1 (fr) 2005-09-01

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CA (1) CA2458752A1 (fr)
TW (1) TW200540217A (fr)
WO (1) WO2005080493A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2138535A1 (fr) 2008-06-23 2009-12-30 Lanxess Deutschland GmbH Compositions de caoutchouc contenant des nanotubes en carbone
CN103788579A (zh) * 2014-01-18 2014-05-14 安徽华联电缆集团有限公司 一种耐高温城轨电缆护套材料
CN107619512A (zh) * 2016-07-13 2018-01-23 赞南科技(上海)有限公司 一种高性能氢化丁腈橡胶胶料及其制备方法
CN110885482A (zh) * 2019-12-16 2020-03-17 江苏冠联新材料科技股份有限公司 一种高强度超耐磨胶辊用nbr胶料

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0518067A2 (fr) * 1991-06-12 1992-12-16 Beiersdorf Aktiengesellschaft Adhésif thermofusible réactif
US5260130A (en) * 1989-09-29 1993-11-09 Shin-Etsu Chemical Co., Ltd. Adhesive composition and coverlay film therewith
US5859155A (en) * 1994-05-24 1999-01-12 Mitsui Chemicals, Inc. Adhesive of epoxy resin, carboxylated rubber aromatic amine and dicyandiamide
US6054509A (en) * 1997-08-28 2000-04-25 Shin-Etsu Chemical Co., Ltd. Adhesive of epoxy resin, nitrile rubbers and curing agent
WO2001014470A1 (fr) * 1999-08-26 2001-03-01 Pirelli Pneumatici S.P.A. Procede de fabrication de pneumatiques, pneumatiques obtenus selon ce procede et compositions elastomeres utilisees
WO2002068528A1 (fr) * 2001-02-23 2002-09-06 Pirelli Pneumatici S.P.A. Procede de production de pneumatiques, pneumatiques ainsi obtenus et compositions elastomeriques utilisees par ce procede
WO2003078163A1 (fr) * 2002-03-15 2003-09-25 Henkel Kommanditgesellchaft Auf Aktien Adhesif epoxyde dote d'une meilleure resistance aux chocs
US6709741B1 (en) * 2001-09-07 2004-03-23 Taiflex Scientific Co., Ltd. FPC adhesive of epoxy resin, onium hexafluoroantimonate, nitrile rubber and filler

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5260130A (en) * 1989-09-29 1993-11-09 Shin-Etsu Chemical Co., Ltd. Adhesive composition and coverlay film therewith
EP0518067A2 (fr) * 1991-06-12 1992-12-16 Beiersdorf Aktiengesellschaft Adhésif thermofusible réactif
US5859155A (en) * 1994-05-24 1999-01-12 Mitsui Chemicals, Inc. Adhesive of epoxy resin, carboxylated rubber aromatic amine and dicyandiamide
US6054509A (en) * 1997-08-28 2000-04-25 Shin-Etsu Chemical Co., Ltd. Adhesive of epoxy resin, nitrile rubbers and curing agent
WO2001014470A1 (fr) * 1999-08-26 2001-03-01 Pirelli Pneumatici S.P.A. Procede de fabrication de pneumatiques, pneumatiques obtenus selon ce procede et compositions elastomeres utilisees
WO2002068528A1 (fr) * 2001-02-23 2002-09-06 Pirelli Pneumatici S.P.A. Procede de production de pneumatiques, pneumatiques ainsi obtenus et compositions elastomeriques utilisees par ce procede
US6709741B1 (en) * 2001-09-07 2004-03-23 Taiflex Scientific Co., Ltd. FPC adhesive of epoxy resin, onium hexafluoroantimonate, nitrile rubber and filler
WO2003078163A1 (fr) * 2002-03-15 2003-09-25 Henkel Kommanditgesellchaft Auf Aktien Adhesif epoxyde dote d'une meilleure resistance aux chocs

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHAKRABORTY S.K. ET AL: "Epoxy-Resin-Cured Carboxylated Nitrile Rubber.", JOURNAL OF APPLIED POLYMER SCIENCE., vol. 27, no. 12, 1982, pages 4561 - 4576, XP001007483, DOI: doi:10.1002/app.1982.070271204 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2138535A1 (fr) 2008-06-23 2009-12-30 Lanxess Deutschland GmbH Compositions de caoutchouc contenant des nanotubes en carbone
US20130261246A1 (en) * 2008-06-23 2013-10-03 Lanxess Deutschland Gmbh Carbon nanotube containing rubber compositions
US8895671B2 (en) 2008-06-23 2014-11-25 Lanxess Deutschland Gmbh Carbon nanotube containing rubber compositions
CN103788579A (zh) * 2014-01-18 2014-05-14 安徽华联电缆集团有限公司 一种耐高温城轨电缆护套材料
CN107619512A (zh) * 2016-07-13 2018-01-23 赞南科技(上海)有限公司 一种高性能氢化丁腈橡胶胶料及其制备方法
CN107619512B (zh) * 2016-07-13 2022-04-08 浙江赞昇新材料有限公司 一种高性能氢化丁腈橡胶胶料及其制备方法
CN110885482A (zh) * 2019-12-16 2020-03-17 江苏冠联新材料科技股份有限公司 一种高强度超耐磨胶辊用nbr胶料

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TW200540217A (en) 2005-12-16

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