WO2013091271A1 - Microporous polyurethane elastomer composition with excellent dynamic performance and method for preparing same - Google Patents
Microporous polyurethane elastomer composition with excellent dynamic performance and method for preparing same Download PDFInfo
- Publication number
- WO2013091271A1 WO2013091271A1 PCT/CN2012/000341 CN2012000341W WO2013091271A1 WO 2013091271 A1 WO2013091271 A1 WO 2013091271A1 CN 2012000341 W CN2012000341 W CN 2012000341W WO 2013091271 A1 WO2013091271 A1 WO 2013091271A1
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- WO
- WIPO (PCT)
- Prior art keywords
- polyurethane elastomer
- polyol
- component
- elastomer composition
- dynamic performance
- Prior art date
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Classifications
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- 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation 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
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
-
- 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
- C08G18/3271—Hydroxyamines
- C08G18/3275—Hydroxyamines containing two hydroxy 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
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
- C08G18/4277—Caprolactone and/or substituted caprolactone
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4825—Polyethers containing two hydroxy 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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
Definitions
- the invention belongs to the field of polyurethane elastomer synthesis, and in particular relates to the preparation of a microcellular polyurethane elastomer composition excellent in dynamic properties.
- the microporous polyurethane elastomer is a novel material between the elastomer and the foam material, and the cell diameter is generally 0.1 to 10 ⁇ ⁇ , the cells are fine and uniform, and the density is lower than the solid elastomer material.
- the mechanical properties are significantly higher than the common foam materials. Therefore, the microcellular polyurethane elastomer has the advantages of light weight, comfort and high strength of the elastomer material and good mechanical properties. It has good cushioning performance and excellent fatigue resistance. It is an elastic material with excellent comprehensive performance. It has broad application potential in some special fields, such as the application of high-speed rail cushions and the preparation of high-speed car shock absorbers.
- the conventional railway cushion plate is made of rubber material.
- the elastic recovery is relatively slow, and the dynamic and static stiffness ratio can reach 1.5 or more. It is difficult to meet the development requirements of high-speed railway.
- the method of partial grooving is often used to reduce the dynamic stiffness of the material, which results in the stress concentration at the root of the groove and the early destruction of the material, and the life is shortened.
- the microporous polyurethane elastomer can easily reduce the dynamic and static stiffness ratio of the material due to the regularity of the molecular structure and the strong molecular design.
- the conventional common polyether is obtained by ring-opening polymerization of propylene oxide and epoxy oxime.
- the molecular structure contains a large number of pendant methyl groups. Although the molecular structure is relatively regular, when subjected to alternating external forces, the molecular chain The motion is affected by the steric hindrance of the side base, and the deformation is lagging behind the change of stress. The energy loss becomes larger, and the dynamic and static stiffness ratio becomes larger. Therefore, the dynamic and static stiffness is also difficult to achieve the dynamic and static stiffness of the current high-speed railway pad. More than the requirements of 1.35.
- Patent CN100506871C reports on a preparation method of NDI-based polyurethane microcellular elastomer. It is well known that polyurethane materials prepared by NDI have excellent dynamic performance, low damping property and high resilience, and are specially suitable for dynamic load and heat resistance. However, this material has a higher melting point, is complicated in the preparation of the polyurethane material, and has poor storage stability, and the prepared prepolymer has a storage stability time of only a few small crucibles.
- Patent CN101469054B reports a preparation method of PPDI-based polyurethane microcellular elastomer, which has better dynamic performance and better storage stability of prepolymer, but PPEI has higher melting point and complicated processing technology; CN101380442B reports a T0DI base.
- the preparation method of the polyurethane microporous elastomer has good processing performance, and the prepared polyurethane microporous elastomer material is excellent in heat resistance, wear resistance and dynamic fatigue property.
- the isocyanates used in the above patents are all special isocyanates, and the raw material cost is relatively high; on the other hand,
- the above patents all use the prepolymer method to prepare the microporous elastomer, the chain extension is carried out by using a small molecule mixture, the viscosity of the prepolymer component is large, the viscosity difference between the two components is large, the material mixing temperature is high, and the mass of the two components is high. The problem is larger than the gap, it is not easy to mix evenly, and the product quality is not easy to control stably.
- the object of the present invention is to provide a microcellular polyurethane elastomer composition excellent in dynamic performance and a preparation method thereof, and the microporous elastomer material prepared according to the composition provided by the invention has excellent dynamic performance and resilience, dynamic and static stiffness ratio 1. 35, 3 million fatigue test after appearance without damage, impact resilience 75%, can be used for the preparation of high-speed rail cushions and automotive shock absorber components.
- microporous polyurethane elastomer composition excellent in dynamic performance comprises the following two components:
- Component A comprising a polymer polyol, a chain extender, a blowing agent, a catalyst A, a catalyst B, a foam stabilizer, and an antioxidant, wherein the other raw materials account for polymerization based on 100% by weight of the total of the polymer polyol.
- the percentage of the total weight of the polyol is: 5% to 12% of the chain extender, 0. 1% ⁇ 0. 3%, the catalyst ⁇ . 3 ⁇ 1.
- 0%, the catalyst B 0. 01% ⁇ 0 6%; 6%; 2%; 0%, antioxidants 0. 3 ⁇ 0. 6%;
- Component B a modified isocyanate component, a mixture of a NC0 group-terminated urethane-modified isocyanate and an isocyanate prepared by reacting a polymer polyol with an isocyanate;
- component A and component B are mixed at a mass ratio of 100: 90 to 110.
- the temperature of component A is 30 V to 45 ° C
- the temperature of component B is 40 ° C to 50 ° C.
- the mass ratio of the component A to the component B is preferably 100: 93 to 100, more preferably 100: 95 to 97.
- the component A temperature is preferably from 33 ° C to 37 ° C
- the component B temperature is preferably from 43 ° C to 47 ° C.
- the polyether polyol or the average functionality of the polymer polyol is preferably from 1.8 to 4, preferably from 2 to 3, and the number average molecular weight is from 1000 to 8000, preferably from 2000 to 6000. 3, preferably 2 to 2. 5, a mixture of one or two of the polyester polyols having a number average molecular weight of from 1,000 to 6,000, preferably from 1,500 to 3,000, in any ratio.
- the polyether polyol is preferably one or a mixture of one or more of a polypropylene oxide ether polyol, a propylene oxide-ethylene oxide copolyether polyol, and a polytetrahydrofuran ether polyol, more preferably a polytetrahydrofuran ether.
- polyester polyols preferably from polycaprolactone polyols, polycarbonate polyols, polyadipate-1,4 butanediol ester polyols, polyadipates-1,6-hexanediol esters One or more of the polyols, more preferably a polycaprolactone polyol.
- the chain extender is preferably selected from the group consisting of ethylene glycol, diethylene glycol, dipropylene glycol, 1,4-butanediol, 1,6-hexanediol or 3,3-dichloro-4, 4- One or more of diphenyltoluenediamine.
- the blowing agent is preferably one or more selected from the group consisting of water, formic acid, acetic acid or monofluorodichloroethane, more preferably water.
- the catalyst A is preferably selected from a tertiary amine catalyst, and may be selected from triethylene glycol of triethylenediamine having a solid content of 33%.
- Catalyst B is preferably one or more selected from the group consisting of an organotin catalyst, an organic ruthenium catalyst or an organozinc catalyst, and dibutyltin dilaurate may be used.
- the foam stabilizer is preferably selected from the group consisting of a silicone surfactant, which may be selected from DC3043 (manufacturer of the US Gas Chemical), 8444 (manufacturer of Shanghai Gao Shimet Chemical) or AK7703 (manufacturer Nanjing Demei Shichuang). One or more.
- the antioxidant is preferably a hindered phenolic antioxidant, and may be selected from BHT264 (2,6-di-tert-butyl-4-methylphenol), ChinoxlOlO (manufacturer is Taiwan Double Bond Chemical) or Irganoxl035 (manufacturer) One or more of Ciba Specialty Chemicals).
- the isocyanate in the modified isocyanate component is preferably 4,4'-diphenylmethyl modified from 4,4'-diphenylmethane diisocyanate (pure MDI) or carbonized diimine-uretonimide. ⁇ Diisocyanate (liquefied MDI), p-phenylene diisocyanate ⁇ ?01), 1,5-naphthalene diisocyanate (1) or 3,3 '-dimethyl-4,4'-biphenyldiisocyanate (T0DI) One or more.
- the modified isocyanate component is preferably from 11% to 14% by weight, more preferably from 12% to 12% by weight, more preferably from 2% to 25%, more preferably from 2 to 2, more preferably from 2 to 2.
- the invention has the following advantages: (1) The invention adopts a semi-prepolymer method to prepare a microporous polyurethane elastomer material, the two components have similar viscosity, the mixing mass ratio is similar, the mixing temperature is low, and the material is easy to be uniformly mixed, the process The control conditions are simple and easy to operate. (2) The microporous polyurethane elastomer material prepared by the composition provided by the invention has a dynamic-static stiffness ratio of 1.35, impact resilience of 75%, no damage after 3 million fatigue tests, and a dimensional change rate of 20%, which can be used for high-speed rail Preparation of high performance products such as cushions and automotive shock absorbers. .
- the temperature of component A is maintained at 35 ° C
- the temperature of component B is maintained at 45 ° C
- the two components are quickly mixed uniformly at a weight ratio of 100: 110, and poured into a mold which is pre-55 ° C, 85 After aging for 10 minutes in the drying tunnel of °C, the mold was opened to obtain a polyurethane microcellular elastomer material.
- PTMG2000 polytetrahydrofuran ether polyol
- the component A temperature at 35 when in use The temperature of C and B components is maintained at 45 V.
- the two components are quickly mixed evenly at a weight ratio of 100:90.
- the mixture is poured into a mold that is pre-55 ° C. After curing for 10 minutes in a drying oven at 85 ° C, the mold is opened. A polyurethane microcellular elastomer material is obtained.
- PTMG2000 polytetrahydrofuran ether polyol
- the moisture content is less than 0.05%, the moisture content is less than 0. 05%, the moisture content is less than 0. 05%, the moisture content is less than 0. 05%, the moisture content is less than 0. 05%, 5 ⁇ 13 ⁇
- the temperature was reduced to 50 ° C, the addition of 72.5 parts of pure MDI, slowly heated to 75 times the incubation reaction 1. 5 hours, adding 15 parts of liquefied MDI, stirring 0. 5 hours, sampling test, - NC0 mass content of 13. 1%, cooled to 50 ° C discharge, sealed and stored.
- the temperature of component A is maintained at 35 ° C
- the temperature of component B is maintained at 45 ° C
- the two components are quickly mixed uniformly at a weight ratio of 100: 92, poured into a mold of 55 ⁇ , and baked at 85 ⁇ . After the mold is aged for 10 minutes, the mold is opened, and a polyurethane microporous elastomer material is obtained.
- PTMG2000 polytetrahydrofuran ether polyol
- component A When used, the temperature of component A was maintained at 35 ° C and the temperature of component B was maintained at 45. C, the two components are quickly mixed uniformly according to the weight ratio of 100 : 95, poured into a mold of 55 ⁇ , and the mold is opened after being aged for 10 minutes in an 85 ⁇ drying tunnel to obtain a polyurethane microcellular elastomer material.
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
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Priority Applications (1)
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BR112013026700A BR112013026700A2 (en) | 2011-12-23 | 2012-03-19 | microporous polyurethane elastomeric compound with excellent dynamic performance and method of compound preparation |
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CN201110437144XA CN102585162A (en) | 2011-12-23 | 2011-12-23 | Microporous polyurethane elastomer compound with excellent dynamic performance and preparation method thereof |
CN201110437144.X | 2011-12-23 |
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