CN104119494A - Preparation method of bio-based polyhydric alcohol - Google Patents
Preparation method of bio-based polyhydric alcohol Download PDFInfo
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- CN104119494A CN104119494A CN201410374574.5A CN201410374574A CN104119494A CN 104119494 A CN104119494 A CN 104119494A CN 201410374574 A CN201410374574 A CN 201410374574A CN 104119494 A CN104119494 A CN 104119494A
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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
- C08G18/30—Low-molecular-weight compounds
- C08G18/36—Hydroxylated esters of higher fatty acids
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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
- C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
- C08G18/6484—Polysaccharides and derivatives thereof
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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
- C08G2101/00—Manufacture of cellular products
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- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
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Abstract
The invention discloses a preparation method of bio-based polyhydric alcohol, which comprises the following steps of: stirring and mixing bio-oil with a polyhydroxy compound according to the mass ratio of 1:0.2 to 1:1.5 at first, adding a solid alkali catalyst, the mass of which is 0.5-2% of the total mass of reactants, heating and stirring at 60-200 DEG C for 2-24 h, cooling, filtering, and eliminating the solid alkali catalyst, thereby obtaining bio-based polyhydric alcohol. According to the invention, the source of raw materials is wide, and the cost advantage is obvious; the biological degradability is good, bio-based polyhydric alcohol can be rapidly degraded, and white pollution is avoided; the preparation process is simple and convenient, and the emission of waste gas, waste water and industrial residue is low; both the molecular structure and the hydroxyl value are adjustable and can be adjusted according to selection of raw materials and the rate of charge; the environmental impact level is low and is far lower than impact of a petroleum-based polyhydric alcohol product; the prepared bio-based polyhydric alcohol is wide in purpose, can be used for replacing the traditional petroleum-based polyhydric alcohol, and can be used in the fields of polyurethane foam, adhesives, polyurethane coatings, surface active agents and the like.
Description
Technical field
The present invention relates to chemical machine synthesis technical field, relate in particular to a kind of preparation method of biopolyol.
Background technology
Polyurethane material excellent performance, of many uses, of a great variety, be one of the fastest macromolecular material of development in recent years, the large synthetic materials in the world the 6th.Urethane is by isocyanic ester and polyol reaction and the polymkeric substance with carbamate segment repeated structural unit of making, it is a kind of segmented copolymer containing soft chain segment and hard segment, hard section is mainly made up of polyisocyanates and small molecule chain extender, and soft section is made up of oligomer polyol (normally polyethers or polyester polyol).Functionality, relative molecular mass and the molecular structure of polyvalent alcohol have conclusive impact to the performance of polyurethane product.In urethane industry, modal is polyether glycol and polyester polyol, and wherein the consumption of polyether glycol proportion maximum in urethane foam, accounts for more than 90%.Polyether glycol normally by low mass molecule alcohol class or amine etc. containing the initiator of reactive hydrogen under catalyst action and the open loop of epoxy compound such as propylene oxide (PO), oxyethane (EO) be polymerized, raw material required in building-up process mostly derives from oil.Oil is as Nonrenewable resources, and scarcity causes the continuous rise of its price, and causes the increase of polyether glycol production cost, makes the development of polyvalent alcohol industry be a greater impact and limit.According to biologist estimation, hundred million tons of the about 1400-1800 of bioenergy total amount (dry weight) of annual growth on the earth, are equivalent to 10 times of current world total energy consumption.The biomass energy of China was also very abundant, and approximately 6.5 hundred million tons of the stalk amounts in now annual rural area, will reach 7.26 hundred million tons by 2010, was equivalent to 500,000,000 tons of mark coals.Bavin firewood and forestry waste quantity are also very large, and forestry waste (not comprising charcoal firewood woods), approximately reaches 3700 m3 every year, are equivalent to 2,000 ten thousand tons of mark coals.If consider increasing municipal wastes and sanitary sewage, fowl is held the other biological matter resources such as ight soil, the annual biomass resource of China has been deducted a part and has been done feed and other raw materials more than reaching 600,000,000 tons of mark coals, and the biomass resource that can be developed as the energy reaches more than 300,000,000 ton of mark coal.And the carrier of biomass energy is organism, so this energy is to exist with form in kind, be that unique one can store and transportable renewable energy source.Its distribution is simultaneously the widest, is not subject to the restriction of weather and natural condition, as long as lived place has biomass to exist.At present, some countries such as U.S., moral, method have started attention Devoting Major Efforts To Developing and have promoted reproducible biomass energy, and Brazil takes the lead in proposing enforcement energy agriculture strategy.In September, 2005, Brazilian agriculture minister's Douglas Rodríguez is write articles and is pointed out, petroleum times is about to finish, and bioenergy will become the new forms of energy that are widely used.Biomass Energy Development with utilize biomass to there is strategic importance; facing under the background of Mineral resources exhaustion; all is seeking taking recycling economy, the ecological economy as guidance in the whole world; adhere to the strategy of sustainable development; from to protect mankind natural resources, ecotope, fully effectively utilize reproducible, huge biomass resource.The strategic importance of biomass energy and biomass utilization is that biomass have the feature multi-functional, multiple-effect is beneficial and in the vital role meeting aspect great strategy demand towards the country.
Summary of the invention
The object of the present invention is to provide one eco-friendly, the simple synthesis of reproducible biopolyol, the method has raw material and is easy to get, renewable, biological degradability is good, and preparation is simple, hydroxyl value is adjustable, applied range, environment affect the advantages such as level is low.
In order to achieve the above object, technical scheme of the present invention is: a kind of preparation method of biopolyol, first being uniformly mixed for 1:0.2～1:1.5 in mass ratio bio oil and polyol, next adds quality is 0.5%～2% solid base catalyst of bio oil and polyol total mass, and at 60～200 DEG C, carry out heated and stirred 2～24h, then cold filtration, removes solid base catalyst, obtains biopolyol.
Described bio-oil is the wherein one of inedible oil, edible fats, animal grease, waste grease.
Described inedible oil is the wherein a kind of of curcas oil, coptis wood oil and Oleum Gossypii semen, described edible fats is the wherein a kind of of soybean oil, rapeseed oil, peanut oil, sunflower seed oil, plam oil, Semen Maydis oil, sesame oil, sweet oil, Rice pollard oil, Oleum Cocois, wheatgerm oil, walnut oil, safflower oil, linseed oil, raisin seed oil, Semen Cucurbitae oil and Semen setariae oil, described animal grease is the wherein a kind of of lard, butter and sheep oil, the grease that described waste grease is sewer oil, become sour and grease factory tankage wherein a kind of.
Described polyol is the wherein one of the hydride of saccharide compound or natural sugar compounds.
Described saccharide compound is the wherein one of glucose, sucrose, starch, chitosan, chitin, and the hydride of described natural sugar compounds is the wherein one of Sorbitol Powder, mannitol, erythritol, maltose alcohol, Saccharum lactis, Xylitol.
Described solid base catalyst is hydrotalcite, basic resin, magnesium oxide, calcium oxide, strontium oxide, salt of wormwood load type active carbon, saltpetre Supported alumina, Potassium monofluoride supported magnesium oxide and sodium hydroxide supported magnesium oxide wherein a kind of of clay, the alkoxyl group exchange of the exchange of hydrotalcite, hydroxide radical.
The invention has the beneficial effects as follows: the present invention is by being uniformly mixed for 1:0.2～1:1.5 in mass ratio bio oil and polyol first, next adds quality is 0.5%～2% solid base catalyst of bio oil and polyol total mass, and at 60～200 DEG C, carry out heated and stirred 2～24h, then cold filtration, remove solid base catalyst, obtain biopolyol.Raw material sources are extensive, and cost advantage is obvious.Vegetables oil used is reproducible biomass, and polyol also can be obtained by reproducible saccharide compound hydrogenating reduction.Biological degradability is good, can degrade rapidly, avoids white pollution.Preparation process is easy, and three waste discharge is low.Molecular structure and hydroxyl value are all adjustable, can be according to material choice and feed ratio Molecular regulator structure and hydroxyl value.Environmental influence level is low, well below the impact of petroleum base polyvalent alcohol product.Gained biopolyol is of many uses, and alternative traditional petroleum base polyvalent alcohol, for fields such as polyurethane foam, sizing agent, polyurethane coating, tensio-active agents.
Embodiment
Embodiment 1
By rapeseed oil and Xylitol in mass ratio 1:0.7 carry out mix and blend, add hydrotalcite, hydrotalcite consumption is 1% of reactant total mass, be warming up to 180 DEG C, at this temperature, carry out after heated and stirred 12h, cooling, remove by filter catalyzer and insolubles, obtain rapeseed oil Xylitol biopolyol product, hydroxyl value is 384mgKOH/g.
Embodiment 2
By curcas oil and starch in mass ratio 1:0.6 carry out mix and blend, add the hydrotalcite of alkoxyl group exchange, catalyst levels is 0.7% of reactant total mass, be warming up to 120 DEG C, at this temperature, carry out after heated and stirred 10h, cooling, remove by filter catalyzer and insolubles, obtain curcas oil starch biopolyol product, hydroxyl value is 415mgKOH/g.
Embodiment 3
By Oleum Gossypii semen and chitosan in mass ratio 1:0.7 carry out mix and blend, add basic resin, catalyst levels is 1% of reactant total mass, be warming up to 160 DEG C, at this temperature, carry out after heated and stirred 12h, cooling, remove by filter catalyzer and insolubles, obtain Oleum Gossypii semen chitosan biopolyol product, hydroxyl value is 435mgKOH/g.
Embodiment 4
By sunflower seed oil and mannitol in mass ratio 1:1 carry out mix and blend, add calcium oxide, catalyst levels is 0.7% of reactant total mass, be warming up to 180 DEG C, at this temperature, carry out after heated and stirred 10h, cooling, remove by filter catalyzer and insolubles, obtain sunflower seed oil mannitol biopolyol product, hydroxyl value is 423mgKOH/g.
Embodiment 5
By plam oil and Sorbitol Powder in mass ratio 1:1.1 carry out mix and blend, add magnesium oxide, catalyst levels is 0.5% of reactant total mass, be warming up to 170 DEG C, at this temperature, carry out after heated and stirred 12h, cooling, remove by filter catalyzer and insolubles, obtain plam oil Sorbitol Powder biopolyol product, hydroxyl value is 452mgKOH/g.
Embodiment 6
By linseed oil and maltose alcohol in mass ratio 1:0.7 carry out mix and blend, add salt of wormwood load type active carbon, catalyst levels is 0.6% of reactant total mass, be warming up to 120 DEG C, at this temperature, carry out after heated and stirred 8h, cooling, remove by filter catalyzer and insolubles, obtain linseed oil maltose alcohol biopolyol product, hydroxyl value is 224mgKOH/g.
Embodiment 7
By lard and Xylitol in mass ratio 1:0.8 carry out mix and blend, add strontium oxide, catalyst levels is 0.8% of reactant total mass, be warming up to 160 DEG C, at this temperature, carry out after heated and stirred 12h, cooling, remove by filter catalyzer and insolubles, obtain lard Xylitol biopolyol product, hydroxyl value is 334mgKOH/g.
Embodiment 8
By sewer oil and Saccharum lactis in mass ratio 1:0.7 carry out mix and blend, add Potassium monofluoride supported magnesium oxide, catalyst levels is 0.9% of reactant total mass, be warming up to 180 DEG C, at this temperature, carry out after heated and stirred 14h, cooling, remove by filter catalyzer and insolubles, obtain lard Xylitol biopolyol product, hydroxyl value is 412mgKOH/g.
Embodiment 9
By coptis wood oil and glucose in mass ratio 1:0.2 carry out mix and blend, add hydrotalcite, hydrotalcite consumption is 1% of reactant total mass, be warming up to 200 DEG C, at this temperature, carry out after heated and stirred 12h, cooling, remove by filter catalyzer and insolubles, obtain coptis wood oil glucose biological polylol product.
Embodiment 10
By soybean oil and sucrose in mass ratio 1:0.3 carry out mix and blend, add the clay of hydroxide radical exchange, the clay consumption of hydroxide radical exchange is 0.5% of reactant total mass, be warming up to 190 DEG C, at this temperature, carry out after heated and stirred 2h, cooling, remove by filter catalyzer and insolubles, obtain soybean oil sucrose biopolyol product.
Embodiment 11
By peanut oil and chitin in mass ratio 1:0.4 carry out mix and blend, add salt of wormwood load type active carbon, salt of wormwood load type active carbon consumption is 0.6% of reactant total mass, be warming up to 180 DEG C, at this temperature, carry out after heated and stirred 4h, cooling, remove by filter catalyzer and insolubles, obtain peanut oil chitin biopolyol product.
Embodiment 12
By Semen Maydis oil and erythritol in mass ratio 1:0.5 carry out mix and blend, add saltpetre Supported alumina, saltpetre Supported alumina consumption is 0.8% of reactant total mass, be warming up to 160 DEG C, at this temperature, carry out after heated and stirred 14h, cooling, remove by filter catalyzer and insolubles, obtain Semen Maydis oil erythritol biopolyol product.
Embodiment 13
By sesame oil and maltose alcohol in mass ratio 1:0.8 carry out mix and blend, add sodium hydroxide supported magnesium oxide, sodium hydroxide supported magnesium oxide consumption is 0.8% of reactant total mass, be warming up to 160 DEG C, at this temperature, carry out after heated and stirred 24h, cooling, remove by filter catalyzer and insolubles, obtain sesame oil maltose alcohol biopolyol product.
Embodiment 14
By sweet oil and maltose alcohol in mass ratio 1:1 carry out mix and blend, add sodium hydroxide supported magnesium oxide, sodium hydroxide supported magnesium oxide consumption is 2% of reactant total mass, be warming up to 100 DEG C, at this temperature, carry out after heated and stirred 20h, cooling, remove by filter catalyzer and insolubles, obtain sweet oil maltose alcohol biopolyol product.
Embodiment 15
By Rice pollard oil and sucrose in mass ratio 1:1.2 carry out mix and blend, add salt of wormwood load type active carbon, salt of wormwood load type active carbon consumption is 1.5% of reactant total mass, be warming up to 80 DEG C, at this temperature, carry out after heated and stirred 10h, cooling, remove by filter catalyzer and insolubles, obtain Rice pollard oil sucrose biopolyol product.
Embodiment 16
By Oleum Cocois and starch in mass ratio 1:1.5 carry out mix and blend, add salt of wormwood load type active carbon, salt of wormwood load type active carbon consumption is 1.8% of reactant total mass, be warming up to 60 DEG C, at this temperature, carry out after heated and stirred 5h, cooling, remove by filter catalyzer and insolubles, obtain Oleum Cocois starch biopolyol product.
Embodiment 17
By wheatgerm oil and Xylitol in mass ratio 1:0.7 carry out mix and blend, add hydrotalcite, hydrotalcite consumption is 0.9% of reactant total mass, be warming up to 70 DEG C, at this temperature, carry out after heated and stirred 22h, cooling, remove by filter catalyzer and insolubles, obtain wheatgerm oil Xylitol biopolyol product.
Embodiment 18
By walnut oil and Xylitol in mass ratio 1:0.7 carry out mix and blend, add hydrotalcite, hydrotalcite consumption is 0.7% of reactant total mass, be warming up to 70 DEG C, at this temperature, carry out after heated and stirred 22h, cooling, remove by filter catalyzer and insolubles, obtain walnut oil and Xylitol biopolyol product.
Embodiment 19
By safflower oil and starch in mass ratio 1:0.5 carry out mix and blend, add sodium hydroxide supported magnesium oxide, sodium hydroxide supported magnesium oxide consumption is 2% of reactant total mass, be warming up to 180 DEG C, at this temperature, carry out after heated and stirred 24h, cooling, remove by filter catalyzer and insolubles, obtain safflower oil and Xylitol biopolyol product.
Embodiment 20
By raisin seed oil and starch in mass ratio 1:0.5 carry out mix and blend, add sodium hydroxide supported magnesium oxide, sodium hydroxide supported magnesium oxide consumption is 1.8% of reactant total mass, be warming up to 140 DEG C, at this temperature, carry out after heated and stirred 12h, cooling, remove by filter catalyzer and insolubles, obtain raisin seed oil starch biopolyol product.
Embodiment 21
By Semen Cucurbitae and chitosan in mass ratio 1:0.5 carry out mix and blend, add sodium hydroxide supported magnesium oxide, sodium hydroxide supported magnesium oxide consumption is 1.4% of reactant total mass, be warming up to 120 DEG C, at this temperature, carry out after heated and stirred 12h, cooling, remove by filter catalyzer and insolubles, obtain Semen Cucurbitae oil chitosan biopolyol product.
Embodiment 22
By Semen setariae oil and chitosan in mass ratio 1:0.5 carry out mix and blend, add sodium hydroxide supported magnesium oxide, sodium hydroxide supported magnesium oxide consumption is 1.1% of reactant total mass, be warming up to 70 DEG C, at this temperature, carry out after heated and stirred 12h, cooling, remove by filter catalyzer and insolubles, obtain Semen setariae oil chitosan biopolyol product.
Embodiment 23
By butter and chitosan in mass ratio 1:0.5 carry out mix and blend, add sodium hydroxide supported magnesium oxide, sodium hydroxide supported magnesium oxide consumption is 0.5% of reactant total mass, be warming up to 60 DEG C, at this temperature, carry out after heated and stirred 9h, cooling, remove by filter catalyzer and insolubles, obtain butter chitosan biopolyol product.
Embodiment 24
By sheep oil and Sorbitol Powder in mass ratio 1:0.5 carry out mix and blend, add calcium oxide, Calcium Oxide Dosage is 0.9% of reactant total mass, be warming up to 60 DEG C, at this temperature, carry out after heated and stirred 9h, cooling, remove by filter catalyzer and insolubles, obtain sheep oil Sorbitol Powder biopolyol product.
Embodiment 25
By the grease becoming sour and Sorbitol Powder in mass ratio 1:0.5 carry out mix and blend, add calcium oxide, Calcium Oxide Dosage is 2% of reactant total mass, be warming up to 200 DEG C, at this temperature, carry out after heated and stirred 24h, cooling, remove by filter catalyzer and insolubles, obtain rapeseed oil Sorbitol Powder biopolyol product.
Embodiment 26
By grease factory tankage and Sorbitol Powder in mass ratio 1:0.5 carry out mix and blend, add calcium oxide, Calcium Oxide Dosage is 2 % of reactant total mass, be warming up to 200 DEG C, at this temperature, carry out after heated and stirred 22h, cooling, remove by filter catalyzer and insolubles, obtain soybean oil Sorbitol Powder biopolyol product.
Claims (6)
1. the preparation method of a biopolyol, it is characterized in that: first being uniformly mixed for 1:0.2～1:1.5 in mass ratio bio oil and polyol, next adds quality is 0.5%～2% solid base catalyst of bio oil and polyol total mass, and at 60～200 DEG C, carry out heated and stirred 2～24h, then cold filtration, remove solid base catalyst, obtain biopolyol.
2. a kind of preparation method of biopolyol according to claim 1, is characterized in that: described bio-oil is the wherein a kind of of inedible oil, edible fats, animal grease, waste grease.
3. a kind of preparation method of biopolyol according to claim 2, it is characterized in that: described inedible oil is curcas oil, the wherein one of coptis wood oil and Oleum Gossypii semen, described edible fats is soybean oil, rapeseed oil, peanut oil, sunflower seed oil, plam oil, Semen Maydis oil, sesame oil, sweet oil, Rice pollard oil, Oleum Cocois, wheatgerm oil, walnut oil, safflower oil, linseed oil, raisin seed oil, the wherein one of Semen Cucurbitae oil and Semen setariae oil, described animal grease is lard, the wherein one of butter and sheep oil, described waste grease is sewer oil, the grease becoming sour, and grease factory tankage is wherein a kind of.
4. a kind of preparation method of biopolyol according to claim 1, is characterized in that: described polyol is hydride wherein a kind of of saccharide compound or natural sugar compounds.
5. a kind of preparation method of biopolyol according to claim 4, it is characterized in that: described saccharide compound is the wherein one of glucose, sucrose, starch, chitosan, chitin, the hydride of described natural sugar compounds is the wherein one of Sorbitol Powder, mannitol, erythritol, maltose alcohol, Saccharum lactis, Xylitol.
6. a kind of preparation method of biopolyol according to claim 1, is characterized in that: described solid base catalyst is hydrotalcite, basic resin, magnesium oxide, calcium oxide, strontium oxide, salt of wormwood load type active carbon, saltpetre Supported alumina, Potassium monofluoride supported magnesium oxide and sodium hydroxide supported magnesium oxide wherein a kind of of clay, the alkoxyl group exchange of hydrotalcite, hydroxide radical exchange.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106634627A (en) * | 2016-11-22 | 2017-05-10 | 汪逸凡 | Preparation method of water-resisting biomass wood adhesive |
| CN107522832A (en) * | 2017-08-10 | 2017-12-29 | 郑州大学 | A kind of bio-based polyurethane polyalcohol and preparation method thereof and the hard polyurethane foam and the method for preparation using its preparation |
| CN109651590A (en) * | 2019-01-07 | 2019-04-19 | 江南大学 | A kind of preparation method of glucose soybean oil base crosslinking one-step synthesis polyurethane |
| CN112920369A (en) * | 2021-01-28 | 2021-06-08 | 孝感市易生新材料有限公司 | Self-antibacterial lactic acid-based waterborne polyurethane, preparation method and emulsion thereof |
| EP4375208A1 (en) * | 2022-11-22 | 2024-05-29 | Amorim Cork Research, Lda. | Vegetable oil-based binder and agglomerated cork stopper comprising the same |
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| CN1910131A (en) * | 2003-10-14 | 2007-02-07 | 康斯乔最高科学研究公司 | Method of preparing fatty acid monoesters |
| CN101249449A (en) * | 2008-03-28 | 2008-08-27 | 华东师范大学 | Novel solid body base catalyst and applications for biological diesel oil synthesizing |
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| CN1842586A (en) * | 2003-08-29 | 2006-10-04 | 株式会社日本触媒 | Method of production of fatty acid alkyl esters and/or glycerine and fatty acid alkyl ester-containing composition |
| CN1910131A (en) * | 2003-10-14 | 2007-02-07 | 康斯乔最高科学研究公司 | Method of preparing fatty acid monoesters |
| CN101249449A (en) * | 2008-03-28 | 2008-08-27 | 华东师范大学 | Novel solid body base catalyst and applications for biological diesel oil synthesizing |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106634627A (en) * | 2016-11-22 | 2017-05-10 | 汪逸凡 | Preparation method of water-resisting biomass wood adhesive |
| CN107522832A (en) * | 2017-08-10 | 2017-12-29 | 郑州大学 | A kind of bio-based polyurethane polyalcohol and preparation method thereof and the hard polyurethane foam and the method for preparation using its preparation |
| CN107522832B (en) * | 2017-08-10 | 2020-05-19 | 郑州大学 | Bio-based polyester polyol, preparation method thereof, polyurethane rigid foam prepared from bio-based polyester polyol and preparation method of polyurethane rigid foam |
| CN109651590A (en) * | 2019-01-07 | 2019-04-19 | 江南大学 | A kind of preparation method of glucose soybean oil base crosslinking one-step synthesis polyurethane |
| CN112920369A (en) * | 2021-01-28 | 2021-06-08 | 孝感市易生新材料有限公司 | Self-antibacterial lactic acid-based waterborne polyurethane, preparation method and emulsion thereof |
| EP4375208A1 (en) * | 2022-11-22 | 2024-05-29 | Amorim Cork Research, Lda. | Vegetable oil-based binder and agglomerated cork stopper comprising the same |
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