CN102660014A - Cardanol polyether polyol and use thereof - Google Patents
Cardanol polyether polyol and use thereof Download PDFInfo
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- CN102660014A CN102660014A CN2012100965157A CN201210096515A CN102660014A CN 102660014 A CN102660014 A CN 102660014A CN 2012100965157 A CN2012100965157 A CN 2012100965157A CN 201210096515 A CN201210096515 A CN 201210096515A CN 102660014 A CN102660014 A CN 102660014A
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- cardanol
- polyether glycol
- polyether polyol
- polyurethane
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Abstract
The invention relates to cardanol polyether polyol and a use thereof. The cardanol polyether polyol comprises cardanol aminal-based polyethylene oxide/propylene oxide polyether polyol and has a hydroxyl value of 220 to 550 and viscosity less than 4500CPS. The cardanol polyether polyol is environmentally friendly. Compared with other phenol-based Mannich polyols, the cardanol polyether polyol has specific physical and chemical properties, and can be used for preparation of polyurethane foam materials such as flame-retardant materials, energy-absorbing semi-rigid foam materials, high-resilience foam materials, polyurethane coatings and other polyurethane elastomeric materials.
Description
Technical field
The present invention relates to a kind of polyether glycol, particularly relate to a kind of cardanol polyether glycol and uses thereof.
Background technology
Urethane is because the numerous advantages of himself; Develop very rapid; Also developed thereupon as urethane important component polyether glycol; Much be to be that the polyether glycol that initiator and propylene oxide and reacting ethylene oxide make has obtained good development with polyvalent alcohol or organic amine; But traditional polyether glycol basically all from the petroleum chemicals derived prods with or its reaction obtain, along with the exhaustion to the growth of requirement and the resource itself of this Nonrenewable resources of oil, oil price is constantly bettered a record.Along with people's progressively strengthens the consciousness of renewable resources simultaneously, and some derive from natural vegetables oil more and more receives people as the substitute of petroleum derivative attention.
Plant phenols is as a kind of natural product, and its raw material sources can comprise cashew nut shell oil based on natural phant; Lacquer tree phenol; With the plant of other similar non-food chain, its staple is a kind of single phenol or bisphenol compound that has long carbochain, because of its particular chemical structure and the special physicochemical characteristic brought thus; Make it when replacing with the oil being the phenol on basis, the advantage of a lot of other improvement and modification also is provided.
Summary of the invention
Technical problem to be solved by this invention overcomes traditional polyether glycol and depends on the shortcoming that non-renewable petroleum resources are raw material, and a kind of polyether glycol based on cardanol is provided.
Another object of the present invention is to provide the purposes of cardanol polyether glycol.
For realizing the object of the invention, technical scheme of the present invention is:
A kind of cardanol polyether glycol is characterized in that, comprises the polyethylene oxide/propylene oxide polyether glycol that is the basis with the cardanol aminal, and it mainly comprises following compound with following structure (separately or with form of mixtures):
Wherein A is:
B, C, D is:
N=0 wherein, 2,4, or 6, r, p, q are positive integer.
In the specific embodiment of the present invention, said cardanol aminal is with cardanol, and formaldehyde and thanomin form for the raw material condensation, and said thanomin is the mixture of diethylolamine or diethylolamine and monoethanolamine.
In the specific embodiment of the present invention, said cardanol is that the primary structure of refining cardanol is following:
N=0 wherein, 2,4, or 6.
Its hydroxyl average functionality is 1.0-2.0, and being preferably the hydroxyl average functionality is 1.0-1.2.
In the specific embodiment of the present invention, the OH value of said Mannich polyether glycol is in the 220-550 scope, and viscosity is less than 4500CPS.
The present invention utilizes the refined product of renewable resources-plant phenols to substitute phenols and alkyl derivative thereof, is the novel plant phenol polyether glycol on basis with the plant phenols thereby obtain a kind of.This polyether glycol is not the Green Product of raw material with non-food product chain plant still, and compares and have special physics and chemical property for the Mannich polyvalent alcohol on basis with other phenols.The hard that is particularly suitable for the water foaming prepares polyurethane foamed material.The present invention provides novel polyols through water foaming, compares the polyvalent alcohol of other types, not only dimensional stability but also have the inherent sticking power of extremely good foam layer.
Adopt the polyurethane coating of this product prepn to compare the polyurethane coating of the polyvalent alcohol preparation of other type, have fabulous water tolerance, alkali resistance is particularly useful for making the polyurethane anticorrosion protective coating of alkaline medium surface contact.
Embodiment
The raw material mass mixture ratio of using in the building-up process below in conjunction with polyether glycol of the present invention specifies its character.
Its building-up process is:
1, the cardanol that adds 50%-99% in the insulation compressive reaction still, the mixture 45-106 kilogram of 100-150 kilogram and diethylolamine or diethylolamine and monoethanolamine, nitrogen purging seals, and heat tracing is stirred to 85-145 ℃.
2, be added drop-wise to 10-30 kilogram 55% (weight) in the reaction kettle in formaldehyde solution through pressurized tank; Reinforced speed is controlled at 85-145 ℃ with temperature of reaction kettle and is as the criterion; Whole charging process need 10-150 minute; Behind reinforced the end, continue insulation half a hour to 3 hour, temperature is controlled at 120-145 ℃.
3, under 102-123 ℃, vacuumize, it is 0.30%-0.50% that moisture is reduced to weight percent, adds catalyst n, N-dimethylethanolamine (DMEA) 1.4-3.9 kilogram, and be controlled at 82-99 ℃ to temperature.
4, ethoxylation: through pressurized tank the propylene oxide of 87-369 kilogram; Or oxyethane, or the mixture of propylene oxide and oxyethane adds in the reaction kettle lentamente, and control reaction temperature is at 85-107 ℃; The reinforced time can accomplish in 2.5-15 hour; After propylene oxide/oxyethane added, reaction mixture remained on identical TR, and continuing the reaction times is 3.0-15 hour; Reaction finishes the back temperature and is controlled at 80-95 ℃, under normal pressure with nitrogen purging resultant of reaction 25-80 minute.The sampling and measuring hydroxyl value.
5, temperature vacuumized 1 hour at 120-135 ℃ at least, and moisture is reduced to below 0.075% (weight).Obtain product.Detect viscosity, performances such as hydroxyl value.
Table 1 has shown a plurality of novel Mannich polyvalent alcohol and performances of preparing according to said process to table 3:
Table 1:
Table 2:
Table 3:
Table 1-3 has shown, the character that polyether glycol had that is prepared by different ratio of components.
Claims (7)
1. a cardanol polyether glycol is characterized in that, comprises the polyethylene oxide/propylene oxide polyether glycol that is the basis with the cardanol aminal, and it mainly comprises following compound with following structure:
Wherein A is:
B, C, D is:
N=0 wherein, 2,4, or 6, r, p, q are positive integer.
2. cardanol polyether glycol according to claim 1 is characterized in that, said cardanol aminal is with cardanol, and formaldehyde and thanomin form for the raw material condensation.
3. cardanol polyether glycol according to claim 1 is characterized in that, said thanomin is the mixture of diethylolamine or diethylolamine and monoethanolamine.
4. cardanol polyether glycol according to claim 2 is characterized in that, said cardanol is that its hydroxyl average functionality of refining cardanol is 1.0-2.0.
5. cardanol polyether glycol according to claim 4 is characterized in that, said hydroxyl average functionality is 1.0-1.2.
6. cardanol polyether glycol according to claim 1, the OH value that it is characterized in that said cardanol polyether glycol is in the 220-550 scope, and viscosity is less than 4500CPS.
7. cardanol polyether glycol according to claim 1 is characterized in that said polyether glycol can be used for polyurethane foamed material.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012100965157A CN102660014A (en) | 2012-04-01 | 2012-04-01 | Cardanol polyether polyol and use thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012100965157A CN102660014A (en) | 2012-04-01 | 2012-04-01 | Cardanol polyether polyol and use thereof |
Publications (1)
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| CN102660014A true CN102660014A (en) | 2012-09-12 |
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| CN2012100965157A Pending CN102660014A (en) | 2012-04-01 | 2012-04-01 | Cardanol polyether polyol and use thereof |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103709395A (en) * | 2013-12-16 | 2014-04-09 | 中国林业科学研究院林产化学工业研究所 | Biomass base structure flame retardant polyol and preparation method and application thereof |
| CN104725604A (en) * | 2014-12-23 | 2015-06-24 | 上海美东生物材料股份有限公司 | Waterborne curing agent and preparation method thereof |
| CN105295018A (en) * | 2015-11-19 | 2016-02-03 | 滕州市科米特新材料有限责任公司 | Modified cardanol-based polyether polyol and high-fire-resistant hard polyurethane foam prepared by modified cardanol-based polyether polyol and preparation method thereof |
| CN105358598A (en) * | 2013-06-25 | 2016-02-24 | 科思创有限公司 | Polyurethane pultrusion formulations for the production of articles with improved coating adhesion and articles produced therefrom |
| WO2016070359A1 (en) * | 2014-11-05 | 2016-05-12 | Dow Global Technologies Llc | Flame retardant polyol |
| CN106432684A (en) * | 2016-09-14 | 2017-02-22 | 中国林业科学研究院林产化学工业研究所 | Self-catalytic anacardol/lignin-based polyurethane foam and preparation method thereof |
| CN108467473A (en) * | 2018-04-16 | 2018-08-31 | 东光县强龙高分子材料有限责任公司 | A kind of natural oil is the hard polyurethane foam and preparation method thereof of raw material |
| CN108623801A (en) * | 2018-05-16 | 2018-10-09 | 苏州保力瑞生物材料科技开发有限公司 | A kind of novel plant polyenoid phenol polyether polyol and preparation method thereof |
| CN109134803A (en) * | 2018-06-25 | 2019-01-04 | 青岛海尔股份有限公司 | Glycol composition and its polyurethane rigid foam plastic of preparation |
| FR3145566A1 (en) | 2023-02-07 | 2024-08-09 | Arkema France | FORMULATIONS BASED ON BIO-SOURCED POLYOLS |
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| WO2010147091A1 (en) * | 2009-06-16 | 2010-12-23 | 旭硝子株式会社 | Process for producing polyether polyol and process for producing rigid foamed synthetic resin using same |
| WO2011003446A1 (en) * | 2009-07-08 | 2011-01-13 | Cimteclab S.R.L. | Synthesis of novel multifunctional cardanol's derivatives and their use as halogen free polyurethanic foams precursors |
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| CN1046730A (en) * | 1989-04-20 | 1990-11-07 | 三井东压化学株式会社 | The preparation method of polyether polyhydroxy-compound |
| EP1475411A1 (en) * | 2003-05-05 | 2004-11-10 | Sika Technology AG | Mannich bases and Preparation of Mannich bases |
| WO2010147091A1 (en) * | 2009-06-16 | 2010-12-23 | 旭硝子株式会社 | Process for producing polyether polyol and process for producing rigid foamed synthetic resin using same |
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Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105358598B (en) * | 2013-06-25 | 2018-08-10 | 科思创有限公司 | It is used to prepare the polyurethane pultrusion preparation of the product with improved coating adherence and product prepared therefrom |
| US10005877B2 (en) | 2013-06-25 | 2018-06-26 | Covestro Llc | Polyurethane pultrusion formulations for the production of articles with improved coating adhesion and articles produced therefrom |
| CN105358598A (en) * | 2013-06-25 | 2016-02-24 | 科思创有限公司 | Polyurethane pultrusion formulations for the production of articles with improved coating adhesion and articles produced therefrom |
| CN103709395B (en) * | 2013-12-16 | 2016-06-08 | 中国林业科学研究院林产化学工业研究所 | Biomass-based structure flame retardant polyol and its preparation method and application |
| CN103709395A (en) * | 2013-12-16 | 2014-04-09 | 中国林业科学研究院林产化学工业研究所 | Biomass base structure flame retardant polyol and preparation method and application thereof |
| JP2017535541A (en) * | 2014-11-05 | 2017-11-30 | ダウ グローバル テクノロジーズ エルエルシー | Flame retardant polyol |
| CN107074740A (en) * | 2014-11-05 | 2017-08-18 | 陶氏环球技术有限责任公司 | Fire retardant polyalcohol |
| WO2016070359A1 (en) * | 2014-11-05 | 2016-05-12 | Dow Global Technologies Llc | Flame retardant polyol |
| CN107074740B (en) * | 2014-11-05 | 2020-11-10 | 陶氏环球技术有限责任公司 | Flame retardant polyols |
| CN104725604A (en) * | 2014-12-23 | 2015-06-24 | 上海美东生物材料股份有限公司 | Waterborne curing agent and preparation method thereof |
| CN105295018A (en) * | 2015-11-19 | 2016-02-03 | 滕州市科米特新材料有限责任公司 | Modified cardanol-based polyether polyol and high-fire-resistant hard polyurethane foam prepared by modified cardanol-based polyether polyol and preparation method thereof |
| CN106432684A (en) * | 2016-09-14 | 2017-02-22 | 中国林业科学研究院林产化学工业研究所 | Self-catalytic anacardol/lignin-based polyurethane foam and preparation method thereof |
| CN106432684B (en) * | 2016-09-14 | 2018-10-02 | 中国林业科学研究院林产化学工业研究所 | A kind of self-catalysis type anacardol/lignin-base polyurethane foam and preparation method thereof |
| CN108467473A (en) * | 2018-04-16 | 2018-08-31 | 东光县强龙高分子材料有限责任公司 | A kind of natural oil is the hard polyurethane foam and preparation method thereof of raw material |
| CN108623801A (en) * | 2018-05-16 | 2018-10-09 | 苏州保力瑞生物材料科技开发有限公司 | A kind of novel plant polyenoid phenol polyether polyol and preparation method thereof |
| CN109134803A (en) * | 2018-06-25 | 2019-01-04 | 青岛海尔股份有限公司 | Glycol composition and its polyurethane rigid foam plastic of preparation |
| FR3145566A1 (en) | 2023-02-07 | 2024-08-09 | Arkema France | FORMULATIONS BASED ON BIO-SOURCED POLYOLS |
| WO2024165811A1 (en) | 2023-02-07 | 2024-08-15 | Arkema France | Formulations based on bio-sourced polyols |
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Owner name: CHANGSHU NAISU BIOMATERIALS TECHNOLOGY CO., LTD. Free format text: FORMER OWNER: NAIS CO., LTD. Effective date: 20131106 Free format text: FORMER OWNER: GUANGZHOU YULI CHEMICAL CO., LTD. BEIJING ORIENTAL CLEARSKY TECHNOLOGY CO., LTD. Effective date: 20131106 |
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Effective date of registration: 20131106 Address after: 215500 Changshu Province, Jiangsu Province, new materials Industrial Park Road, Yu Sheng, No. 26 Applicant after: Changshu Naisu Biological Material Technology Co., Ltd. Address before: Lewis, 16192, coast road, Delaware Applicant before: Naisu Co., Ltd. Applicant before: Guangzhou Yuli Chemical Co., Ltd. Applicant before: Beijing Dongfangqingkong Technology Co., Ltd. |
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Application publication date: 20120912 |