EP3041877A1 - Blends of thermoplastic polyurethanes and rubbers and process for producing same - Google Patents
Blends of thermoplastic polyurethanes and rubbers and process for producing sameInfo
- Publication number
- EP3041877A1 EP3041877A1 EP14758515.2A EP14758515A EP3041877A1 EP 3041877 A1 EP3041877 A1 EP 3041877A1 EP 14758515 A EP14758515 A EP 14758515A EP 3041877 A1 EP3041877 A1 EP 3041877A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- rubbers
- rubber
- blends
- nitrile
- mixtures
- 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- Withdrawn
Links
Classifications
-
- 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
- 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
- C08G18/0895—Manufacture of polymers by continuous processes
-
- 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
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3237—Polyamines aromatic
- C08G18/3243—Polyamines aromatic containing two or more aromatic rings
-
- 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
Definitions
- the invention relates to the field of chemistry and relates to blends of thermoplastic polyurethanes and rubbers, as can be used, for example, for applications in which good mechanical properties, good tear and abrasion resistance, good damping properties, high chemical resistance are required, such as for rollers and roll covers in the printing, textile, paper and graphic industry, industrial wheels, bumpers, pump impellers or drive belts, and a method for their manufacture.
- polymer blends are mixtures of chemically different polymers, the chemical diversity of the polymers causing their non- and partial miscibility. Polymer blends are characterized by their chemical structure, the conformation of their chain molecules in the molecular range and their morphology in the order of molecular structure.
- Polymer blends can have improved mechanical and tribological properties compared to the individual polymers, since in this case the properties of the polymer blends result from the combination of the properties of the polymers involved (Ott, KH, et al .: Kunststoffhandbuch, Polymerblends, 1, Carl Hanser Verlag, 1993 ).
- polymer blends are defined as a macroscopically homogeneous mixture of two or more different polymers. They are usually produced by intensive mechanical mixing of molten polymers, resulting in a homogeneous material. When the melt cools, the polymer chains remain finely divided, thus ensuring that the property profile of the blend is a permanent superposition of the properties of the individual polymers (Wikipedia, keyword polymer blend).
- compositions of polyurethanes and rubbers are known in the art.
- thermoplastic polyurethane elastomer blend which is composed of at least 30 to at most 40% by volume of a polyurethane component and at least 60 to at most 70% by volume of a nitrile rubber and has a Shore A hardness from about 55 to 70 with added plasticizer.
- the polyurethane component contains at least 50% by weight of polyisocyanate and the nitrile rubber component contains about 34% by mol of acrylonitrile.
- thermoplastic polyurethane having a glass transition temperature of less than 60 ° C and a rubbery material from the group of rubbers, thermoplastic elastomers, thermoplastic vulcanizates and plastomers, which has a glass transition temperature of less than -20 ° C have.
- the weight ratio of the thermoplastic polyurethane to the rubber is at most 50:50.
- thermoplastic polymer blend comprising polyvinyl chloride, polyether urethane and a butadiene-acrylonitrile copolymer, wherein the mixture 65 to 80 parts by weight of the polyvinyl halide resin having a specific viscosity of 0.28 to 0.4, 5 bis 25 parts by weight of an unhardened aliphatic hydrocarbon-diene-aliphatic nitrile rubber copolymer having a Mooney viscosity of 47 to 70 and 5 to 25 parts by weight of a polyether polyurethane having a 350 ° F melt index of 0 to 100.
- the plasticizer is a mixture consisting of 25% to 75% of an ester plasticizer and 75% to 25% of a viscous liquid reaction product of a polyurethane elastomer with an amine, wherein the ester plasticizer has general compatibility with the rubber and the Polyurethane reaction product, dioctyl phthalate, dibutyl phthalate, Dioctyladipat and Dioctylsebacat has.
- US Pat. No. 4,374,192 discloses an electrophotographic developer consisting of coated carrier particles together with toner particles, the coating consisting of a mixture of a butadiene-acrylonitrile rubber.
- the blend contains 20% to 40% by weight of acrylonitrile and a polyurethane elastomer and is soluble in organic solvents.
- thermoplastic polymer blends have insufficient physical properties. It is also disadvantageous that known processes for producing thermoplastic polymer blends are energy-consuming and expensive.
- the object of the present invention is to provide blends of thermoplastic polyurethanes and rubbers which have improved physical properties and a simple energy and inexpensive process for their preparation.
- thermoplastic polyurethanes and rubbers consist of rubber or a rubber mixture and 5 to 80 wt .-%, based on the blend, of one or more thermoplastic polyurethanes which are homogenized in the rubber or in the rubber mixture, and wherein in the contact areas between gums or rubber compounds and polyurethanes gearing the materials together.
- rubbers or rubber mixtures synthetic rubbers, natural rubbers, acrylate, chloroprene, halobutyl, polyurethane, isoprene, butyl, nitrile-butadiene rubbers, thermoplastic elastomers, thermoplastic vulcanizates and / or plastomers or mixtures thereof, advantageously vulcanized rubbers or rubber compounds.
- thermoplastic polyurethanes advantageously up to 70 wt .-%, based on the blend, thermoplastic polyurethanes present.
- At least one rubber or a rubber mixture is homogenized, after homogenization of which 5 to 80% by weight precursors of polyurethanes, based on the blend, are added and homogenized, the precursors
- Monomers of one or more polyisocyanates, macroglycols and chain extenders are monomers of one or more polyisocyanates, macroglycols and chain extenders.
- Synthetic rubbers natural rubbers, acrylate, chloroprene, halobutyl, polyurethane, isoprene, butyl rubbers, thermoplastic elastomers, thermoplastic vulcanizates and / or plastomers or mixtures thereof are advantageously used as rubbers or rubber mixtures.
- diene rubbers and / or hydrogenated diene rubbers are diene rubbers and / or hydrogenated diene rubbers, in particular nitrile rubbers, such as nitrile-butadiene rubbers, carboxylated nitrile-butadiene rubbers, hydrogenated nitrile-butadiene rubbers, hydrogenated carboxylated nitrile-butadiene rubbers, nitrile-isoprene rubbers. Rubbers, butadiene rubbers and / or styrene-butadiene rubbers can be used.
- nitrile rubbers such as nitrile-butadiene rubbers, carboxylated nitrile-butadiene rubbers, hydrogenated nitrile-butadiene rubbers, hydrogenated carboxylated nitrile-butadiene rubbers, nitrile-isoprene rubbers. Rubbers, butadiene rubbers and / or styrene-butad
- polyisocyanates used are aliphatic, aromatic, cycloaliphatic and / or araliphatic polyisocyanates, in particular diisocyanates.
- macroglycols are used based on polyolefins, polycarbonates, polyacetates, polysiloxanes, polycaprolactones, Polyesters, polyethers and / or block copolymers of polyester and polyether or mixtures thereof.
- amine-based compounds multifunctional compounds containing isocyanate-reactive hydrogen atoms, diols, diamine and / or mixtures of these materials are used as chain extenders.
- the prepolymer is prepared by mixing and reacting polyisocyanate (s) and macroglycol (s).
- vulcanizing agents such as sulfur compounds, accelerated sulfur compounds, peroxides, hydrogen peroxide coagens compounds, phenolic resins, catalysts, plasticizer oils, organic fillers, inorganic fillers, antioxidants, plasticizers, UV stabilizers , Flame retardants and / or additives used.
- homogenization and vulcanization are realized in an internal mixer, a rolling mill and / or an extruder.
- thermoplastic polyurethanes and rubbers by a process which have improved physical properties and can be prepared simply, as well as energy and inexpensively.
- the blends according to the invention consist of thermoplastic polyurethanes and rubbers, wherein in the blends 5 to 80 wt .-%, based on the blend, of one or more thermoplastic polyurethanes are present which are homogenized in the rubber or in the rubber mixture, and in the contact areas between rubber or rubber compounds and polyurethanes gearing the materials together.
- rubbers or rubber mixtures are advantageously vulcanized rubbers or vulcanized rubber mixtures, synthetic rubbers, natural rubbers, acrylate, chloroprene, halobutyl, polyurethane, isoprene, butyl, nitrile-butadiene rubbers, thermoplastic elastomers, thermoplastic vulcanizates and / or plastomers or mixtures thereof.
- the blend contains up to 70% by weight of thermoplastic polyurethanes which are homogenized in the rubber or in the rubber mixture and have toothings of the materials with one another in the contact regions between rubber or rubber mixtures and polyurethanes.
- the blends according to the invention are prepared by a process in which at least one rubber or a rubber mixture is homogenized. Subsequently, 5 to 80 wt .-% precursors of polyurethanes, based on the blend, are added and homogenized with the rubber or the rubber mixture. These precursors are
- Monomers of one or more polyisocyanates, macroglycols and chain extenders are monomers of one or more polyisocyanates, macroglycols and chain extenders.
- a prepolymer of polyisocyanate (s) and macroglycol (s) is prepared by mixing and reactive reaction and added together with at least one chain extender to the rubber or rubber mixture.
- the resulting polymer blend is advantageously subjected to a vulcanization process of the rubber or the rubber mixture.
- the prepolymer prepared from polyisocyanates and macroglycols
- the monomers of polyisocyanates and macroglycols can be used together with the chain extender for the in-situ formation of thermoplastic polyurethane in the rubber directly.
- in-situ synthesized polyurethane is formed by the addition of the precursors during mixing with the rubber or the rubber mixture, which forms an improved homogenization and in the contact areas of polyurethane and rubber, a toothing of the materials what to improved properties of the blend according to the invention, such as an improved modulus of elasticity, increased breaking stress, elongation at break and hardness with reduced abrasion behavior leads.
- the blend according to the invention has an isocyanate index of 90 to 110.
- the isocyanate index is understood to mean the percentage ratio of isocyanate groups to isocyanate-reactive hydrogen atoms in the blend.
- thermoplastic polyurethanes and rubbers can be produced with advantageous properties when the Polyurethane precursors / precursors of a prepolymer of polyisocyanate (s) and macroglycol (s) and chain extenders or monomers of polyisocyanate (s) and macroglycol (s) and chain extenders are synthesized in-situ during homogenization and advantageously vulcanization of the rubbers to thermoplastic polyurethanes ,
- Organic polyisocyanates used according to the invention are advantageously aliphatic, aromatic, cycloaliphatic and araliphatic polyisocyanates, especially diisocyanates such as hexamethylene diisocyanate, isophorone diisocyanate, 4,4'-disocyanates, tetramethyl-m-xylylene diisocyanate, tetramethyl-p-xylylene diisocyanate, toluene diisocyanate, xylene diisocyanate, phenylene diisocyanates, preferably 4,4'-diphenylmethane diisocyanate, optionally with isomers of diphenylmethane diisocyanate.
- the polyisocyanate used according to the invention may also be a compound having reactive isocyanate side groups, as is known in polyurethane technology.
- macroglycols also called polyols, which are based on polyolefins, polycarbonates, polyacetates, polysiloxanes, preferably polycaprolactone, polyesters, polyethers, block copolymers of polyester / polyethers and the like, and mixtures thereof.
- Saturated and / or unsaturated polyols can also be used according to the invention.
- Chain extenders which may advantageously be used are multifunctional and in particular diisocyanate-reactive hydrogen-containing compounds, preferably diols and more preferably diamines or a mixture of different types.
- the amine-based chain extenders, preferably diamines may be selected from the following classes of compounds: 4,4'-methylenedianiline, o-phenylenediamine, m-phenylenediamine, p-phenylenediamine, 4,4'-methylenebis (2-methoxyaniline), bis (4-amino-2-chloro-3,5-diethylphenyl) -methane, 4,4'-methylenebis (2-6-diethylaniline), 4,4'-methylenebis (2-methyl-aniline), 4,4 Methylene-bis (2-6-dimethyl-aniline), 4,4'-methylenebis (2-isopropyl-6-methyl-aniline), 4,4'-methylenebis (2,6-diisopropylaniline) , Diethyl
- the rubber component may be selected from any conventional rubbers known in the art. From polar rubbers such as nitrile-butadiene rubber, carboxylated nitrile-butadiene rubber, hydrogenated nitrile-butadiene rubber, hydrogenated carboxylated nitrile-butadiene rubber, nitrile-isoprene rubber, acrylate rubber, chloroprene rubber, halobutyl rubber, Polyurethane rubber and the like; also from non-polar rubbers such as natural rubber, isoprene rubber, butadiene rubber, styrene-butadiene rubber, butyl rubber and the like, or also from mixtures of different rubbers.
- the rubber component may also consist of thermoplastic elastomers, thermoplastic vulcanizates, plastomers or other rubbery materials.
- the rubber component of this invention are, in particular, diene rubbers, hydrogenated diene rubbers, preferably nitrile rubber, and advantageously nitrile-butadiene rubber.
- the rubber component is preferably crosslinked by conventional vulcanization or electron beam induced vulcanization.
- Typical crosslinkers are sulfur compounds, accelerated sulfur compounds, peroxides, hydrogen peroxide-coagens compounds, phenolic resins, and / or combinations thereof.
- Auxiliaries and additives typical of polyurethane and rubber technology can also be used. This includes the use of compatibilizers, such as surfactants, to adjust the interfacial tension between the polyurethane and rubber phases.
- compatibilizers such as surfactants
- the in situ process of the present invention can be accomplished using conventional internal mixers, rolling mills or extruders known in the art.
- the process according to the invention is also particularly advantageous since highly reactive and high molecular weight amine-based chain extenders can be used without the use of a catalyst in order to obtain the blend according to the invention, which consists of a matrix of rubber in which polyurethane is distributed in finely dispersed form. It is advantageous that with the diamine content of the chain extender in the in-situ synthesized thermoplastic polyurethanes, a significant mechanical reinforcement of the blend is achieved.
- the inventive method allows a high degree of flexibility in the adaptation of the soft and hard segments of the in-situ synthesized thermoplastic polyurethanes and leads to significantly improved physical properties, in particular in tensile and abrasion resistance.
- nitrile-butadiene rubber 100 g are kneaded in a heated internal mixer (Haake Rheomix 600P) at 120 ° C. and 60 rpm for 5 minutes. following 8.2 g of prepolymer (methylene diphenyl diisocyanates, polyester-based prepolymer, with 8.54 wt .-% isocyanates) and 2.9 g of 4,4 '- (m-phenylene diisopropylidene) anilines are pre-mixed as a chain extender and added to the mixing in the rubber and the components. 5 Minutes mixed at 120 ° C. The added starting materials have an isocyanate index of 100.
- prepolymer methylene diphenyl diisocyanates, polyester-based prepolymer, with 8.54 wt .-% isocyanates
- 4,4 '- (m-phenylene diisopropylidene) anilines 5 Minutes mixed at 120 ° C.
- the resulting mixture is then mixed on a rolling mill (Servitec Polymix 1 1 OL) for 10 minutes with 5 g of zinc oxides, 2 g of stearic acid, 1, 7 g of N-cyclohexyl-2-benzothiazolylsulfenamid (CBS) and 2 g of sulfur and then on a Heating press vulcanized at a temperature of 150 ° C and a pressure of 15 MPa.
- a rolling mill Server Polymix 1 1 OL
- CBS N-cyclohexyl-2-benzothiazolylsulfenamid
Landscapes
- 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)
- Manufacturing & Machinery (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102013217661.9A DE102013217661B4 (en) | 2013-09-04 | 2013-09-04 | Process for producing blends of thermoplastic polyurethanes and rubbers and blends produced therewith |
PCT/EP2014/068245 WO2015032681A1 (en) | 2013-09-04 | 2014-08-28 | Blends of thermoplastic polyurethanes and rubbers and process for producing same |
Publications (1)
Publication Number | Publication Date |
---|---|
EP3041877A1 true EP3041877A1 (en) | 2016-07-13 |
Family
ID=51483396
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP14758515.2A Withdrawn EP3041877A1 (en) | 2013-09-04 | 2014-08-28 | Blends of thermoplastic polyurethanes and rubbers and process for producing same |
Country Status (6)
Country | Link |
---|---|
US (1) | US10450445B2 (en) |
EP (1) | EP3041877A1 (en) |
JP (1) | JP2016529376A (en) |
KR (1) | KR20160056906A (en) |
DE (1) | DE102013217661B4 (en) |
WO (1) | WO2015032681A1 (en) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPWO2019124502A1 (en) * | 2017-12-22 | 2020-11-19 | Toyo Tire株式会社 | Rubber composition and pneumatic tires |
DE102018204884A1 (en) * | 2018-03-29 | 2019-10-02 | SchäferRolls GmbH & Co. KG | Process for the preparation of a polyurethane and a polyurethane produced or preparable by the process |
FR3086950B1 (en) | 2018-10-09 | 2020-12-25 | Hutchinson | RUBBER COMPOSITION FOR DYNAMIC APPLICATIONS, ITS PREPARATION PROCESS, PRODUCTS INCORPORATED AND USES |
KR20210112357A (en) | 2019-01-04 | 2021-09-14 | 바스프 에스이 | Rigid Phase Modified Thermoplastic Polyurethane |
EP3741912A1 (en) * | 2019-05-22 | 2020-11-25 | Valmet Technologies Oy | Roll for manufacture of a fibrous web and method for making it |
CN111763417A (en) * | 2020-06-30 | 2020-10-13 | 江阴久盛科技有限公司 | Nano titanium dioxide filled thermoplastic polyurethane/chloroprene rubber blend composite material and preparation method thereof |
CN112708255A (en) * | 2020-12-24 | 2021-04-27 | 广州机械科学研究院有限公司 | Low-temperature-resistant elastomer rubber composition and application thereof |
FI20216016A1 (en) * | 2021-09-30 | 2023-03-31 | Valmet Technologies Oy | Belt |
CN114395246B (en) * | 2021-12-20 | 2024-02-23 | 绍兴市聚成新材料科技股份有限公司 | Dynamically vulcanized silica gel modified polyurethane and preparation method thereof |
CN115403837B (en) * | 2022-10-11 | 2024-04-05 | 无锡二橡胶股份有限公司 | Production formula of high-speed spinning high-count differential fiber drafting rubber roller |
CN117946343A (en) * | 2024-01-27 | 2024-04-30 | 广州佳沐体育发展有限公司 | Lockable plastic throwing court ground material |
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WO2007025690A1 (en) * | 2005-09-01 | 2007-03-08 | Sartomer Technology Co., Inc. | High modulus rubber composition |
EP1889735A1 (en) * | 2006-07-26 | 2008-02-20 | Sumitomo Rubber Industries, Ltd. | Rubber composition and tire using same |
US20080045643A1 (en) * | 2006-08-17 | 2008-02-21 | Henning Steven K | High Modulus Rubber Compositions and Articles |
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-
2013
- 2013-09-04 DE DE102013217661.9A patent/DE102013217661B4/en active Active
-
2014
- 2014-08-28 US US14/916,375 patent/US10450445B2/en active Active
- 2014-08-28 EP EP14758515.2A patent/EP3041877A1/en not_active Withdrawn
- 2014-08-28 JP JP2016539479A patent/JP2016529376A/en not_active Ceased
- 2014-08-28 KR KR1020167008878A patent/KR20160056906A/en not_active Application Discontinuation
- 2014-08-28 WO PCT/EP2014/068245 patent/WO2015032681A1/en active Application Filing
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WO2007025690A1 (en) * | 2005-09-01 | 2007-03-08 | Sartomer Technology Co., Inc. | High modulus rubber composition |
EP1889735A1 (en) * | 2006-07-26 | 2008-02-20 | Sumitomo Rubber Industries, Ltd. | Rubber composition and tire using same |
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Title |
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See also references of WO2015032681A1 * |
Also Published As
Publication number | Publication date |
---|---|
US10450445B2 (en) | 2019-10-22 |
KR20160056906A (en) | 2016-05-20 |
JP2016529376A (en) | 2016-09-23 |
WO2015032681A1 (en) | 2015-03-12 |
DE102013217661B4 (en) | 2023-01-12 |
US20160194483A1 (en) | 2016-07-07 |
DE102013217661A1 (en) | 2015-03-05 |
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