CN103923291A - High-performance polyurethane elastomer and preparation method thereof - Google Patents
High-performance polyurethane elastomer and preparation method thereof Download PDFInfo
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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
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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
- C08G18/28—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
- C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
- C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
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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
- C08G18/28—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
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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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
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Abstract
The invention discloses a high-performance polyurethane elastomer and a preparation method thereof. The high-performance polyurethane elastomer comprises two parts, i.e., a prepolymer component (component A) and a chain extender (component B), wherein the component A comprises the following materials in parts by weight: 100 parts of macromolecular dihydric alcohol and 14-35 parts of PPDI; the component B comprises the following materials in parts by weight: 100 parts of chain extender and 0.1-0.5 part of catalyst; the weight ratio of the component A to the component B is 100: 6-15; the chain extender is micromolecular dihydric alcohol, three-functionality-degree alcohol amine, three-functionality-degree alcohol or combination thereof; the micromolecular dihydric alcohol is selected from resorcinol-bi(beta-ethoxyl) ether (HER) or composition of the resorcinol-bi (beta-ethoxyl) ether (HER) and p-hydroquinone-bi(beta-ethoxyl) ether (HQEE) in the weight ratio of 1:0-2. The obtained elastomer material has the advantages that the permanent deformation is small, the resilience is excellent, the heat resistance and the mechanical performance are good and the temperature for the use and the operation of the prepolymer is low.
Description
Technical field
The present invention relates to a kind of high performance polyurethane (PU) elastomerics and preparation method thereof, particularly there is the high-performance polyurethane elastomer of excellent rebound performance, low compression set ability, good resistance toheat, mechanical property and dynamic properties.
Background technology
On polyurethane elastomer molecular chain, contain a large amount of polar groups (as ester group, ether, carbamate groups, urea groups, biuret groups and allophanate group etc.), and there is very strong Intermolecular Forces and hydrogen bond, thereby give elastomerics many good performances, as good mechanical property, comprise tensile strength, tear strength and wear resisting property.And still there is good elasticity and elongation in high rigidity (Shao Er 80A～80D) scope, but this intermolecular strong interaction force make PU elastomerics under dynamic working conditions in (discharging as compression repeatedly) heat-dissipating serious, in life-time service or use temperature higher in the situation that, its physical dimension will change, and the performance such as hardness, intensity, modulus, resilience, compression set all declines.So the polyurethane elastomer goods of high-mechanic will ensure long term operation, not only need to possess suitable hardness, good mechanical strength, also to there is good rebound performance, low compression set ability.
Mostly be tolylene diisocyanate (TDI)-amine chain extender, diphenylmethanediisocyanate (MDI)-ol class chainextender system for the polyurethane elastomer material of this series products in the market, although TDI elastomer material can be prepared suitable hardness, and possesses good mechanical strength, but due to the asymmetry structure of TDI and amine chain extender form more crosslinked, make material in possessing higher force intensity, rebound performance and low compression set ability.And for MDI based article, the internal heat-dissipating impact of temperature is huge, when applied at elevated temperature, can cause temperature to raise, finally affect the work-ing life of elastomeric article.
Li Xianhui, Pang Kun Wei .PPDI type polyurethane elastomerics thermotolerance research [J]. polyurethane industrial, 2005,20 (5), 17-20, has studied the resistance toheat of PPDI type PUE to make chainextender by oneself, and chainextender structure is indefinite.Li Yanfei, Pang Kunwei, Qu Zhimin. the elastomeric synthetic and performance study [J] of PPDI type polyurethane. polyurethane industrial, 2007, 22 (2), 21-24, study the elastomeric thermotolerance of PPDI type polyurethane, wherein use taking HQEE as chainextender, when independent use HQEE is during as chainextender, PPDI performed polymer component must keep comparatively high temps (being not less than 100 DEG C), in guarantee casting process, HQEE does not separate out, this PPDI for easy distillation is great inferior position, not only can cause performed polymer at high temperature rotten, also easily cause environmental pollution, and operator are caused to actual bodily harm.
Patent documentation CN102260368A provides a kind of polyurethane elastomer damper material and preparation method, but material rebound degree is little, and compression set is large, and characteristic feature performance rebound degree is 42%, compression set is 27%.In patent documentation CN101796092B, prepare polyurethane roller taking PPDI as raw material, the BDO that the solidifying agent of employing contains 60～99 % by weight and mostly be the diamine of 40 % by weight most and mostly be the catalyzer of 1 % by weight most.BDO easily makes the polyurethane elastomer material of PPDI system have larger tension set as chainextender.
Summary of the invention
First technical problem that the present invention will solve is to provide a kind of high-performance polyurethane elastomer material, this material has avoided causing while using BDO as chainextender the inferior position of the larger permanent deformation of PU elastomer material, and the elastomer material obtaining still has excellent rebound performance, good resistance toheat and mechanical property.
Second technical problem that the present invention will solve is to provide a kind of preparation method of high-performance polyurethane elastomer material, avoid in the time using HQEE as chainextender, PPDI performed polymer needs comparatively high temps, and cause PPDI distillation, the rotten problem of performed polymer, reduce environmental pollution and the harmful effect to operator's health.
High-performance polyurethane elastomer material of the present invention is made up of performed polymer component (A component) and chain extender component (B component) two portions:
(1) A component, comprises in weight part:
Macromolecule dihydric alcohol 100
PPDI (PPDI) 14～35
(2) B component, comprises in weight part:
Chainextender 100
Catalyzer 0.1～0.5
AB weight ratio is 100/6～15.
Macromolecule dihydric alcohol of the present invention is selected from polyester diol, PCDL or polytetrahydrofuran dibasic alcohol (PTMG) or its combination that molecular weight is 1000-3000.Preferred molecular weight 1000-2000.Wherein, polyester diol comprises the reaction product of small molecules di-carboxylic acid and small molecules dibasic alcohol, also comprise the product that various lactones and diol reaction obtain, as caprolactone reacts ε-polycaprolactone dibasic alcohol (PCL) etc. of preparation with ethylene glycol, glycol ether etc.The poly-hexanodioic acid that is preferably molecular weight 1000-2000 is polyester diol, ε-polycaprolactone.
Chainextender of the present invention is small molecules dibasic alcohol, three-functionality-degree hydramine, three-functionality-degree alcohol or its combination.Its small molecular di-alcohols chainextender is selected from two (beta-hydroxyethyl) ether (HER) of Resorcinol or two (beta-hydroxyethyl) ether (HER) of Resorcinol and the composition to quinhydrones-bis-(beta-hydroxyethyl) ether (HQEE), wherein HER/HQEE weight ratio is 1/0～2, preferably 1/0.5～1.5.Three-functionality-degree alcamines is as tri-isopropanolamine (TIPA), three-functionality-degree alcohol chainextender is as trimethylolethane (TME), glycerine (GLY), TriMethylolPropane(TMP) (TMP), polycaprolactonetriol etc., preferably TIPA, TMP and polycaprolactonetriol, its small molecular di-alcohols chainextender/three-functionality-degree alcohols or alcoholamine chain extender weight ratio are 1/0～2, preferably 1/0～1.8.
Catalyzer of the present invention is one or more mixtures in tertiary amines, organo-bismuth class or organic tin compound.The preferred triethylene diamine of tertiary amine catalyst; Organo-bismuth compounds is selected from isocaprylic acid bismuth and bismuth carboxylate or its combination, and organic tin compound is selected from one or more in stannous octoate (T-9), two sad two fourth tin and dibutyl tin dilaurate (T-12) etc.
The preparation method of high-performance polyurethane elastomer material of the present invention, comprises the following steps:
(1) preparation of A component: at 95～120 DEG C, the vacuum tightness 2～3h that dewaters under-0.098～-0.1MPa, adds PPDI, reacts 1.5～2.5h at 70～80 DEG C by the macromolecule dihydric alcohol of metering, vacuum defoamation, cooling discharge, sealing is preserved;
(2) preparation of B component: by liquid chainextender or melt as chainextender, the catalyzer of liquid stirs by metering in advance, mix, keeping chainextender is that liquid state is used;
(3) elastomeric preparation: material cast can adopt machine cast or hand dropping, A component temperature is 75～90 DEG C, B component temperature is 80～100 DEG C, two components are fully mixed, implantation temperature is in the mould of 110～130 DEG C, demould time 30～60min, after the demoulding goods need be at 120～125 DEG C of temperature postcure 16～24h.
Gained high-performance polyurethane elastomer material property of the present invention is in table 1.
Table 1 high-performance polyurethane elastomer material property
| Hardness/Shao A | 80～98 |
| Tensile strength/MPa | 35～55 |
| Tear strength/N/mm | 105～140 |
| Elongation/% | 250～600 |
| Rebound degree/% | 52～70 |
| Compression set/% (70 DEG C/22h) | 8～15 |
| R value | <1.2 |
Note: R value is the ratio of the storage modulus of material at 75 DEG C and 150 DEG C (E '), and R value is less, and the interior heat-dissipating of illustrative material under hot conditions is less, and thermotolerance is better.
High-performance polyurethane elastomer material of the present invention, avoid causing while using BDO as chainextender the inferior position of the larger permanent deformation of PU elastomer material, and the elastomer material obtaining still have excellent rebound performance, good resistance toheat, mechanical property and dynamic properties.Avoid in the time using HQEE as chainextender, PPDI performed polymer needs comparatively high temps simultaneously, and causes PPDI distillation, the rotten problem of performed polymer, has reduced environmental pollution and the harmful effect to operator's health.
Resulting materials of the present invention can be applicable to require high performance polyurethane rubber roll, rubber tire and the bumper and absorbing shock goods etc. that resistance toheat is good, load-carrying properties are high, dynamic heat build up is little.
Embodiment
Below in conjunction with embodiment, the invention will be further described.
Embodiment 1
(1) preparation of A component: the PCL that is 2000 by 400g number-average molecular weight is at 95～100 DEG C, and the 2h that dewaters under vacuum tightness-0.1MPa, adds 67.6g PPDI, reacts 1.5h at 70～80 DEG C, vacuum defoamation, discharging is for subsequent use.
(2) preparation of B component: 100g HER, after 85 DEG C of thawings, is mixed with the catalyzer (solution that the triethyl diamine contents that uses propylene glycol preparation is 33%) of 0.4g, and keeps liquid state.
(3) elastomeric preparation: A component is remained on to 75～80 DEG C, and B component remains on 80～85 DEG C, A/B component mixes after also deaeration according to weight ratio 100/9, pour in the mould of 120 DEG C, the 60min demoulding, 120 DEG C of postcure 20h, room temperature is placed after 7 days and is surveyed performance.Resulting materials performance is in table 2.
Embodiment 2
(1) preparation of A component: the PCL that is 1000 by 400g number-average molecular weight is at 95～100 DEG C, and the 2h that dewaters under vacuum tightness-0.1MPa, adds 118g PPDI, reacts 1.5h at 70～80 DEG C, vacuum defoamation, discharging is for subsequent use.
(2) preparation of B component: 60g HER, 30g HQEE, after 100 DEG C of thawings, are mixed with the catalyzer (solution that the triethyl diamine contents that uses propylene glycol preparation is 33%) of 0.45g, and keep liquid state.
(3) elastomeric preparation: A component is remained on to 75～80 DEG C, and B component remains on 85～90 DEG C, A/B component mixes after also deaeration according to weight ratio 100/12, pour in the mould of 120 DEG C, the 30min demoulding, 120 DEG C of postcure 20h, room temperature is placed after 7 days and is surveyed performance.Resulting materials performance is in table 2.
Embodiment 3
(1) preparation of A component: the PCL that is 1000 by 400g number-average molecular weight is at 95～100 DEG C, and the 2h that dewaters under vacuum tightness-0.1MPa, adds after 104.5g PPDI, is to react 1.5h at 70～80 DEG C in temperature, vacuum defoamation, discharging is for subsequent use.
(2) preparation of B component: 50g HER, 50g HQEE and 15.7g TIPA is after 100 DEG C of thawings, even with 0.4gT12 catalyst mix, and keep liquid state.
(3) elastomeric preparation: A component is remained on to 75～80 DEG C, and B component remains on 85～90 DEG C, A/B component mixes after also deaeration according to weight ratio 100/8.3, pour in the mould of 120 DEG C, the 60min demoulding, 120 DEG C of postcure 20h, room temperature is placed after 7 days and is surveyed performance.Resulting materials performance is in table 2.
Embodiment 4
(1) preparation of A component: the polybutylene glyool adipate that is 1000 by 400g number-average molecular weight is at 100～110 DEG C, the 3h that dewaters under vacuum tightness-0.1MPa, adds 124g PPDI, is to react 1.5h at 70～80 DEG C in temperature, vacuum defoamation, discharging is for subsequent use.
(2) preparation of B component: 60g HER, 30g HQEE, after 100 DEG C of thawings, are mixed with the catalyzer (solution that the triethyl diamine contents that uses propylene glycol preparation is 33%) of 0.45g, and keep liquid state.
(3) elastomeric preparation: A component is remained on to 75～80 DEG C, and B component remains on 85～90 DEG C, A/B component mixes after also deaeration according to weight ratio 100/13.4, pour in the mould of 120 DEG C, the 60min demoulding, 120 DEG C of postcure 20h, room temperature is placed after 7 days and is surveyed performance.Resulting materials performance is in table 2.
Comparative example 1
(1) preparation of A component: the PCL that is 1000 by 400g number-average molecular weight is at 95～100 DEG C, and the 2h that dewaters under vacuum tightness-0.1MPa, adds after 118g PPDI, is to react 1.5h at 70～80 DEG C in temperature, vacuum defoamation, discharging is for subsequent use.
(2) preparation of B component: 60g HQEE, after 100 DEG C of thawings, is mixed with the catalyzer (solution that the triethyl diamine contents that uses propylene glycol preparation is 33%) of 0.45g, and keeps liquid state.
(3) elastomeric preparation: A component is remained on to 100～110 DEG C, and B component remains on 105～110 DEG C, mixes A/B component after also deaeration according to weight ratio 100/8.8, pour in the mould of 120 DEG C, the 30min demoulding, 120 DEG C of postcure 20h, room temperature is placed after 7 days and is surveyed performance.Resulting materials performance is in table 2.
Table 2 resulting materials performance
Claims (10)
1. a high-performance polyurethane elastomer, is made up of performed polymer component (A component) and chain extender component (B component) two portions:
(1) A component, comprises in weight part:
Macromolecule dihydric alcohol 100
PPDI (PPDI) 14～35
(2) B component, comprises in weight part:
Chainextender 100
Catalyzer 0.1～0.5
A, B weight ratio are 100/6～15;
Described chainextender is small molecules dibasic alcohol, three-functionality-degree hydramine, three-functionality-degree alcohol or its combination; Described small molecules dibasic alcohol is selected from two (beta-hydroxyethyl) ether (HER) of Resorcinol or two (beta-hydroxyethyl) ether (HER) of Resorcinol and the composition to quinhydrones-bis-(beta-hydroxyethyl) ether (HQEE), and wherein HER/HQEE weight ratio is 1/0～2.
2. high-performance polyurethane elastomer according to claim 1, it is characterized in that three-functionality-degree hydramine refers to tri-isopropanolamine (TIPA), three-functionality-degree alcohol refers to trimethylolethane (TME), glycerine (GLY), TriMethylolPropane(TMP) (TMP) or polycaprolactonetriol; Small molecules dibasic alcohol/three-functionality-degree alcohol or hydramine weight ratio are 1/0～2.
3. high-performance polyurethane elastomer according to claim 2, is characterized in that HER/HQEE weight ratio is 1/0.5～1.5, and small molecules dibasic alcohol/three-functionality-degree alcohol or hydramine weight ratio are 1/0～1.8.
4. high-performance polyurethane elastomer according to claim 1, is characterized in that described macromolecule dihydric alcohol is selected from polyester diol, PCDL or polytetrahydrofuran dibasic alcohol (PTMG) or its combination that molecular weight is 1000-3000.
5. high-performance polyurethane elastomer according to claim 4, is characterized in that described polyester diol refers to the product that the reaction product of small molecules di-carboxylic acid and small molecules dibasic alcohol, various lactone and diol reaction obtain.
6. high-performance polyurethane elastomer according to claim 5, is characterized in that described polyester diol refers to that the poly-hexanodioic acid of molecular weight 1000-2000 is polyester diol, ε-polycaprolactone.
7. high-performance polyurethane elastomer according to claim 1, is characterized in that catalyzer refers to one or more mixtures in tertiary amines, organo-bismuth class or organic tin compound.
8. high-performance polyurethane elastomer according to claim 7, is characterized in that catalyzer refers to one or more in triethylene diamine, isocaprylic acid bismuth and/or bismuth carboxylate, stannous octoate (T-9), two sad two fourth tin or dibutyl tin dilaurate (T-12).
9. a method of preparing the described high-performance polyurethane elastomer of one of claim 1-8, comprises the following steps:
(1) preparation of A component: at 95～120 DEG C, the vacuum tightness 2～3h that dewaters under-0.098～-0.1MPa, adds PPDI, reacts 1.5～2.5h at 70～80 DEG C by the macromolecule dihydric alcohol of metering, vacuum defoamation, cooling discharge, sealing is preserved;
(2) preparation of B component: by liquid chainextender or melt as chainextender, the catalyzer of liquid stirs by metering in advance, mix, keeping chainextender is that liquid state is used;
(3) elastomeric preparation: material cast can adopt machine cast or hand dropping, A component temperature is 75～90 DEG C, B component temperature is 80～100 DEG C, two components are fully mixed, implantation temperature is in the mould of 1 10～130 DEG C, demould time 30～60min, after the demoulding goods need be at 120～125 DEG C of temperature postcure 16～24h.
10. the method for preparing high-performance polyurethane elastomer according to claim 9, is characterized in that resulting materials has following performance:
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| CN105131235A (en) * | 2015-09-19 | 2015-12-09 | 烟台德邦科技有限公司 | Synthesis method of thermoplastic polyurethane elastomer |
| CN105131234A (en) * | 2015-09-08 | 2015-12-09 | 沈阳化工大学 | Radiation-resistant robot crawler and preparation method thereof |
| CN105504209A (en) * | 2015-12-31 | 2016-04-20 | 山东一诺威聚氨酯股份有限公司 | Mechanical property-improved polyurethane elastomer and preparation method thereof |
| CN107312129A (en) * | 2017-06-28 | 2017-11-03 | 苏州奥斯汀新材料科技有限公司 | A kind of low compression set deformation method for preparing thermoplastic polyurethane elastomer |
| CN108586697A (en) * | 2018-05-10 | 2018-09-28 | 青岛海洋新材料科技有限公司 | A kind of low compression set polyurethane elastomer pointing and preparation method thereof |
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| CN114891182A (en) * | 2022-05-27 | 2022-08-12 | 唯万科技有限公司 | High-temperature-resistant sealing material for main seal of excavator and preparation method thereof |
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