CN114891177B - Chain extender and application thereof in polyurethane elastomer - Google Patents
Chain extender and application thereof in polyurethane elastomer Download PDFInfo
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- CN114891177B CN114891177B CN202210489304.3A CN202210489304A CN114891177B CN 114891177 B CN114891177 B CN 114891177B CN 202210489304 A CN202210489304 A CN 202210489304A CN 114891177 B CN114891177 B CN 114891177B
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- C08G18/30—Low-molecular-weight compounds
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- 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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- 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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- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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- C08G18/61—Polysiloxanes
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- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/6505—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen the low-molecular compounds being compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6511—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen the low-molecular compounds being compounds of group C08G18/32 or polyamines of C08G18/38 compounds of group C08G18/3203
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Abstract
The invention belongs to the technical field of polyurethane elastomers, and particularly relates to a chain extender and application thereof in a polyurethane elastomer. A chain extender characterized by: the chain extender comprises the following components in percentage by mass: 3-16% of thiophene containing dihydroxy or dimercapto, 1-8% of hydroxyl-terminated organic silicon, and the balance of micromolecular polyalcohol chain extender and/or micromolecular alcamines chain extender, wherein the hydroxyl-terminated organic silicon is polyether-polysiloxane copolymer with hydroxyl at two ends. The chain extender is applied to the polyurethane elastomer, and the hydrophobicity of the polyurethane elastomer is improved through the synergistic effect of the thiophene containing dihydroxy or dimercapto and the hydroxyl-terminated organic silicon, so that the polyurethane elastomer has excellent mechanical properties and low haze.
Description
Technical Field
The invention belongs to the technical field of polyurethane elastomers, and particularly relates to a chain extender and application thereof in a polyurethane elastomer.
Background
The polyurethane elastomer, abbreviated as TPU, is a linear block copolymer composed of an oligomer polyol soft segment and a diisocyanate-chain extender hard segment, and becomes one of the most rapidly developed high polymer materials due to excellent wear resistance, mechanical properties and rebound resilience. The organosilicon has excellent performances of high temperature resistance, hydrolysis resistance and the like because Si-O-Si bonds in a molecular chain have larger cohesive energy, and the chain belongs to a flexible chain and has the advantages of good low-temperature flexibility, low surface tension, good biocompatibility and the like.
In recent years, there are many reports on silicone-modified polyurethanes, and the addition modes of silicone are generally classified into two types, physical blending and copolymerization modification. The organosilicon additive is added into the polyurethane resin in a physical blending mode, and due to the poor compatibility of organosilicon and polyurethane, the organosilicon is separated out by simple physical mixing, and the stability is relatively poor. The copolymerization modification is usually carried out by a hydroxyl-or amino-terminated siloxane. The patent with the application number of 2020109386421 discloses an organic silicon modified waterborne polyurethane waterproof coating and a preparation method thereof, wherein the preparation method comprises the steps of carrying out prepolymerization reaction on polyol, isocyanate and a catalyst to obtain a first prepolymer, then sequentially adding a chain extender and a neutralizing agent to react to obtain a waterborne polyurethane prepolymer, mixing and modifying the waterborne polyurethane prepolymer and KH-550, and mixing the modified waterborne polyurethane prepolymer and an emulsifying agent to obtain the organic silicon modified waterborne polyurethane waterproof coating.
Disclosure of Invention
In order to solve the problems in the prior art, the invention provides a polyurethane elastomer and a preparation method thereof.
The chain extender comprises the following components in percentage by mass: 3-16% of thiophene containing dihydroxyl or dimercapto, 1-8% of hydroxyl-terminated organic silicon, and the balance of micromolecular polyalcohol chain extender and/or micromolecular alcamines chain extender, wherein the hydroxyl-terminated organic silicon is polyether-polysiloxane copolymer with hydroxyl at two ends.
Preferably, the bishydroxy-or dimercapto-containing thiophene is 2, 5-dihydroxy-1, 4-dithiane or 2, 5-dimethylmercapto-1, 4-dithiane.
Preferably, the small-molecule polyol chain extender is at least one of the following compounds: ethylene glycol, diethylene glycol, 1, 2-propanediol, 1, 4-butanediol, 1, 6-hexanediol, neopentyl glycol.
Preferably, the small molecule alcamine chain extender is at least one of the following compounds: ethanolamine, diethanolamine.
An application of a chain extender in polyurethane elastomer.
Preferably, the following method is used: dehydrating oligomer polyol, and then mixing the oligomer polyol with diisocyanate for reaction to obtain a prepolymer with NCO content of 3.0-9.0%; adding the chain extender and the catalyst into the prepolymer, and mixing to obtain the polyurethane elastomer, wherein the mass ratio of the prepolymer to the chain extender is 100: (12-18).
Preferably, the diisocyanate is at least one of the following compounds: toluene diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, dicyclohexylmethane diisocyanate.
Preferably, the oligomer polyol is at least one of polyester polyols having a functionality of 2 and a number average molecular weight of 500 to 4000.
Preferably, the catalyst is at least one of dibutyltin dilaurate and stannous octoate.
Compared with the prior art, the invention has the beneficial effects that:
the chain extender containing dihydroxy or dimercapto thiophene and hydroxyl-terminated organic silicon is applied to the field of polyurethane elastomers, the hydroxyl-terminated organic silicon and the dihydroxy or dimercapto thiophene replace a part of conventional chain extenders, and the polyurethane elastomer prepared through the synergistic effect of the hydroxyl-terminated organic silicon and the dihydroxy or dimercapto thiophene has good hydrophobicity and excellent mechanical properties, and simultaneously keeps good low haze.
Detailed Description
The invention is further described with reference to specific examples.
The raw material sources are as follows:
PE-4005 poly (adipic acid) polyester diol having a number average molecular weight of 500, available from Nowes polyurethane, inc., shandong;
PE-2320 Polyadipate polyester diol, number average molecular weight 2000, available from Nowegian polyurethane, inc., shandong;
PE-4040 Polyadipate polyester diol, number average molecular weight 4000, from Norway polyurethane, inc. in Shandong;
PCL-1000 polycaprolactone diol, number average molecular weight 1000, from Shandong Nonwei polyurethane, inc.;
PCL-2000 polycaprolactone diol, number average molecular weight 2000, from Shandong Novew polyurethane, inc.;
toluene diisocyanate, trade name WANNATE TDI-80, available from Vanhua Chemicals;
isophorone diisocyanate, trade name WANNATEIPDI, available from warhua chemicals;
hexamethylene diisocyanate, trade name WANNATEHDI, available from wannhua chemistry;
dicyclohexylmethane diisocyanate, trade name WANNATEHMDI, available from wanhua chemistry;
polydimethylsiloxane is available from Shanghai Tager Polymer technology, inc. under the designation TECH-2187.
Others are commercially available technical grades.
Example 1
Firstly, 80 g of PE-4005 poly adipic acid polyester dihydric alcohol is dehydrated at the temperature of 100 ℃ and the vacuum degree of 0.095MPa until the water content is 0.03 percent, and then the dehydrated product reacts with 10 g of toluene diisocyanate at the temperature of 80 ℃ for 3 hours to obtain a prepolymer with the NCO content of 3.0 percent; then mixing 1g of dibutyltin dilaurate, 100 g of prepolymer and 12 g of chain extender at 80 ℃, pouring the mixture into a mold with the temperature of 120 ℃, opening the mold after 40min, and vulcanizing to obtain the polyurethane elastomer, wherein the chain extender comprises: 10% of 2, 5-dihydroxy-1, 4-dithiane, 5% of polydimethylsiloxane, and the balance of ethylene glycol.
Example 2
Firstly, 65 g of PE-2320 polyester adipate diol is dehydrated at the temperature of 100 ℃ and the vacuum degree of 0.095MPa until the water content is 0.03%, and then the dehydrated polyester diol reacts with 25 g of toluene diisocyanate at the temperature of 80 ℃ for 3 hours to obtain a prepolymer with the NCO content of 9.0%; then mixing 1g of dibutyltin dilaurate, 100 g of prepolymer and 15 g of chain extender at 80 ℃, pouring the mixture into a mold with the temperature of 120 ℃, opening the mold after 40min, and vulcanizing to obtain the polyurethane elastomer, wherein the chain extender comprises: 16% of 2, 5-dihydroxy-1, 4-dithiane, 1% of polydimethylsiloxane, and the balance of 1, 2-propanediol.
Example 3
Firstly, 90 g of PE-4040 poly adipic acid polyester diol is dehydrated at the temperature of 100 ℃ and the vacuum degree of 0.095MPa until the water content is 0.03%, and then the dehydrated diol reacts with 18 g of isophorone diisocyanate at the temperature of 80 ℃ for 3 hours to obtain a prepolymer with the NCO content of 6.0%; then mixing 1g of stannous octoate, 100 g of prepolymer and 18 g of chain extender at 80 ℃, pouring into a mold at the temperature of 120 ℃, opening the mold after 60min, and vulcanizing to obtain the polyurethane elastomer, wherein the chain extender comprises: 3% of 2, 5-dimethylmercapto-1, 4-dithiane, 8% of polydimethylsiloxane and the balance of diethanolamine.
Example 4
Firstly, 80 g of PCL-2000 polycaprolactone diol is dehydrated at the temperature of 100 ℃ and the vacuum degree of 0.095MPa until the water content is 0.03 percent, and then the 80 ℃ of the 15 g of hexamethylene diisocyanate is reacted for 3 hours to obtain a prepolymer with the NCO content of 5.0 percent; then mixing 1g of dibutyltin dilaurate, 100 g of prepolymer and 14 g of chain extender at 80 ℃, pouring the mixture into a mold with the temperature of 120 ℃, opening the mold after 40min, and vulcanizing to obtain the polyurethane elastomer, wherein the chain extender comprises: 9% of 2, 5-dihydroxy-1, 4-dithiane, 7% of polydimethylsiloxane and the balance of 1, 6-hexanediol.
Example 5
Firstly, 80 g of PCL-1000 polycaprolactone diol is dehydrated at the temperature of 100 ℃ and the vacuum degree of 0.095MPa until the water content is 0.03%, and then the 80 ℃ of the 10 g of dicyclohexylmethane diisocyanate reacts for 3 hours to obtain a prepolymer with the NCO content of 3.0%; then mixing 1g of dibutyltin dilaurate, 100 g of prepolymer and 12 g of chain extender at 80 ℃, pouring the mixture into a mold with the temperature of 120 ℃, opening the mold after 60min, and vulcanizing to obtain the polyurethane elastomer, wherein the chain extender comprises: 3% of 2, 5-dimethylmercapto-1, 4-dithiane, 5% of polydimethylsiloxane, the remainder being neopentyl glycol.
Example 6
The present embodiment is different from embodiment 1 in that: the chain extender comprises: 10% of 2, 5-dihydroxy-1, 4-dithiane and the balance ethylene glycol.
Example 7
The present embodiment is different from embodiment 1 in that: the chain extender comprises: 5% of polydimethylsiloxane D-1000, and the balance being ethylene glycol.
Example 8
The present embodiment is different from embodiment 1 in that: the chain extender is ethylene glycol.
The polyurethane elastomers obtained in examples 1 to 8 were subjected to property tests, and the test results are shown in Table 1. Wherein, the hardness is tested according to the GB/T2411 standard; the tensile strength and the elongation at break are determined according to GB/T16777-2008 standard; detecting the contact angle by referring to the GB/T30447-2013 standard; the haze was measured using a WGW photoelectric haze meter according to GB/T2410-2008 standard.
Table 1 results of performance testing of examples 1-8
The hydrophobicity of example 6 is significantly reduced compared to examples 1-5, indicating that the addition of the hydroxyl terminated silicone can increase the hydrophobicity of the polyurethane elastomer. Compared with examples 1-5, example 7 has higher haze, which shows that thiophene containing dihydroxy or dimercapto can improve the transparency of polyurethane material, and the material has low haze.
The hydrophobicity of the polyurethane material in the embodiment 8 is lower than that in the embodiments 6 and 7, and the haze of the polyurethane material in the embodiment 8 is the highest than that in the embodiments 6 and 7, which shows that the hydroxyl-terminated organosilicon and the thiophene containing the dihydroxy or the dimercapto have synergistic effect, and the hydrophobic property of the polyurethane material can be further improved by the mutual cooperation of the hydroxyl-terminated organosilicon and the thiophene containing the dihydroxy or the dimercapto.
The above detailed description is only for explaining the present application, and it is not limited to the present application, and those skilled in the art can make modifications to the present embodiment as necessary without inventive contribution after reading the present specification, but all of them are protected by patent law within the scope of the claims of the present application.
Claims (8)
1. A chain extender characterized by: the chain extender comprises the following components in percentage by mass: 3-16% of thiophene containing dihydroxy or dimercapto, 1-8% of hydroxyl-terminated organic silicon, and the balance of micromolecular polyalcohol chain extender and/or micromolecular alcamines chain extender, wherein the hydroxyl-terminated organic silicon is polyether-polysiloxane copolymer with hydroxyl at two ends;
the thiophene containing dihydroxy or dimercapto is 2, 5-dihydroxy-1, 4-dithiane or 2, 5-dimethylmercapto-1, 4-dithiane.
2. A chain extender in accordance with claim 1, wherein: the small-molecule polyol chain extender is at least one of the following compounds: ethylene glycol, diethylene glycol, 1, 2-propylene glycol, 1, 4-butanediol, 1, 6-hexanediol, neopentyl glycol.
3. A chain extender in accordance with claim 1, wherein: the micromolecule alcamines chain extender is at least one of the following compounds: ethanolamine, diethanolamine.
4. Use of a chain extender according to any one of claims 1 to 3 in a polyurethane elastomer.
5. Use of a chain extender according to claim 4 in polyurethane elastomers, characterized in that: the following method is adopted: dehydrating oligomer polyol, and then mixing the oligomer polyol with diisocyanate for reaction to obtain a prepolymer with NCO content of 3.0-9.0%; adding the chain extender and the catalyst into the prepolymer and then mixing to obtain the polyurethane elastomer, wherein the mass ratio of the prepolymer to the chain extender is 100: (12-18).
6. Use of a chain extender according to claim 5 in a polyurethane elastomer, characterized in that: the diisocyanate is at least one of the following compounds: toluene diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, dicyclohexylmethane diisocyanate.
7. Use of a chain extender according to claim 5 in polyurethane elastomers, characterized in that: the oligomer polyol is at least one of polyester polyols with the functionality of 2 and the number average molecular weight of 500-4000.
8. Use of a chain extender according to claim 5 in polyurethane elastomers, characterized in that: the catalyst is at least one of dibutyltin dilaurate and stannous octoate.
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| CN1299382A (en) * | 1996-09-23 | 2001-06-13 | 弹性医学有限公司 | Polysiloxane-contg. polyurethane elastomeric compositions |
| CN102918073A (en) * | 2010-03-31 | 2013-02-06 | 陶氏环球技术有限责任公司 | Polyurethane compositions having improved impact resistance and optical properties |
| CN103119077A (en) * | 2010-07-20 | 2013-05-22 | 拜耳知识产权有限责任公司 | Polyurethane having high light refraction |
| CN110194826A (en) * | 2018-08-31 | 2019-09-03 | 广东工业大学 | Modified polyorganosiloxane and its application |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1701988A4 (en) * | 2003-11-28 | 2009-11-04 | Commw Scient Ind Res Org | Polyurethanes |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1299382A (en) * | 1996-09-23 | 2001-06-13 | 弹性医学有限公司 | Polysiloxane-contg. polyurethane elastomeric compositions |
| CN102918073A (en) * | 2010-03-31 | 2013-02-06 | 陶氏环球技术有限责任公司 | Polyurethane compositions having improved impact resistance and optical properties |
| CN103119077A (en) * | 2010-07-20 | 2013-05-22 | 拜耳知识产权有限责任公司 | Polyurethane having high light refraction |
| CN110194826A (en) * | 2018-08-31 | 2019-09-03 | 广东工业大学 | Modified polyorganosiloxane and its application |
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