CN103497300B - The preparation method of cellulose acetate modified lignin resin polyurethane film - Google Patents
The preparation method of cellulose acetate modified lignin resin polyurethane film Download PDFInfo
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- 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
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4081—Mixtures of compounds of group C08G18/64 with other macromolecular compounds
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- 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
- C08G18/6492—Lignin containing materials; Wood resins; Wood tars; Derivatives thereof
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- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
- C08L75/08—Polyurethanes from polyethers
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- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
- C08J2375/08—Polyurethanes from polyethers
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- C08J2401/00—Characterised by the use of cellulose, modified cellulose or cellulose derivatives
- C08J2401/08—Cellulose derivatives
- C08J2401/10—Esters of organic acids
- C08J2401/12—Cellulose acetate
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L2205/14—Polymer mixtures characterised by other features containing polymeric additives characterised by shape
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Abstract
The preparation method of cellulose acetate modified lignin resin polyurethane film, step is: the mixing of cellulose acetate, xylogen and polyvalent alcohol; The formation of cellulose acetate modified lignin resin polyurethane film; In cellulose acetate modified lignin resin polyurethane film, solvent dispels; The slaking of cellulose acetate modified lignin resin polyurethane film.Such polyurethane film is that auxiliary material adds with cellulose acetate, fully can mix with xylogen and polyvalent alcohol in a solvent, pass through blending and modifying, enhance the mechanical property of lignin polyurethane film, and improve its hydrophilicity, thus expanding the range of application of lignin polyurethane film, the practical application for lignin polyurethane film has certain meaning.
Description
Technical field
The invention belongs to xylogen Application Areas, be specifically related to the preparation method that a kind of cellulose acetate strengthens lignin polyurethane film.
Background technology
Along with the development of science and technology, the application of polymeric film in national economy is more and more extensive, also more and more higher to the requirement of thin-film material use properties.Polyurethane film has high tensile, high-tensile strength, water-proof breathable properties, obdurability and ageing-resistant performance, and there is excellent biology and blood compatibility and chemical proofing, simultaneously because its goods are easy to use, the reasons such as functional diversities, polyurethane film is obtained develop rapidly, and be widely used in multiple fields such as health care, high-grade weaving face fabric, industry, the dark welcome by user and favor.
At present, the exhaustion day by day of fossil resource is one of difficult problem of generally facing of the whole world, and renewable biomass resource just causes and pays close attention to widely, substitutes with biomass resource the only way which must be passed that fossil resource development chemical industry is human kind sustainable development.Xylogen is that vegitabilia is only second to cellulosic the abundantest a kind of larger molecular organics matter, and it is the aromatic polymer of the complexity be aggregating in a certain way by phenylpropyl alcohol alkyl structure unit.Prove after deliberation; the xylogen with a large amount of alcoholic extract hydroxyl groups and phenolic hydroxyl group can replace polyvalent alcohol and isocyanic ester generation nucleophilic addition for the preparation of polyurethane material; so not only can reduce the dependency to petroleum products; improve the added value of xylogen; and reduce cost for polyurethane industrial, to the development of polyurethane industrial and extenuate energy dilemma and be all of great practical significance and strategic importance.
But the partial properties of traditional lignin polyurethane film does not reach the performance of conventional polyurethanes film, limits the scope of its industrial applications, therefore improving its performance has important meaning for the range of application expanding lignin polyurethane film.
In the present invention, cellulose acetate modified lignin resin polyurethane film is prepared by blended method, its mechanical property improves, and too increase the wetting ability of lignin polyurethane film, thus expanding the range of application of lignin polyurethane film, the practical application for lignin polyurethane has certain meaning.
Summary of the invention
the technical problem solved:the object of the invention is the preparation method providing a kind of cellulose acetate modified lignin resin polyurethane film.Such polyurethane film with cellulose acetate and xylogen for raw material, by the proportioning of cellulose acetate and xylogen and polyvalent alcohol to the analysis of its mechanical property, thermal characteristics and hydrophilicity and then when finding the optimum performance of film.
technical scheme:the preparation method of cellulose acetate modified lignin resin polyurethane film, step is:
(1) mixing of cellulose acetate, xylogen and polyvalent alcohol: the cellulose acetate taking 5 ~ 40 mass parts, the xylogen of 5 ~ 40 mass parts is dissolved in organic solvent, and adds the polyvalent alcohol of 15 ~ 75 mass parts, stirs 0.5 ~ 2h, make it fully mix at 50 ~ 60 DEG C;
(2) formation of cellulose acetate modified lignin resin polyurethane film: the isocyanic ester of 40 ~ 70 mass parts is added in the liquid mixture of step (1) gained and stir, at 60 ~ 80 DEG C after confined reaction 1 ~ 1.5h, pour in Teflon mould, mould is inserted on a horizontal stand, leave standstill 12 ~ 24h;
(3) slaking of cellulose acetate modified lignin resin polyurethane film: the film of step (2) gained is put into baking oven slaking 1 ~ 3h at 80 ~ 100 DEG C;
(4) the dispelling of solvent in cellulose acetate modified lignin resin polyurethane film: soak 24 ~ 36h under the film of step (3) gained being put into water room temperature;
(5) the further slaking of cellulose acetate modified lignin resin polyurethane film: the film of step (4) gained is put into baking oven and obtain the finished product after slaking 1 ~ 3h at 100 ~ 200 DEG C.
The ethanoyl mass percentage of described cellulose acetate is 30 ~ 40%, and corresponding hydroxyl mass percentage is 4.0 ~ 9.0%.
Described organic solvent is the organic solvent by acetone and DMF 2:3 mixing by volume.
Described polyol component is that in molecule, hydroxy radical content is 2 ~ 3, relative molecular mass is the mixture of one or more in the polyvalent alcohol of 600 ~ 2000.
Described isocyanic ester is tolylene diisocyanate (TDI), diphenylmethanediisocyanate (comprising PAPI and MDI), hexamethylene diisocyanate (HDI) or isophorone diisocyanate (PPDI).
The molecular weight of described xylogen is 1000 ~ 20000; Described xylogen is sulfate-reducing conditions, alkali lignin, sulfonated lignin, high-boiling alcohol lignin, enzymolysis xylogen, thermo-cracking xylogen, acetic acid lignin, Peracetic Acid xylogen or peroxy acid xylogen.
Principle of the present invention is: utilize cellulose acetate can well be dissolved in mixed solvent and fully mix with xylogen and isocyanic ester, and the acetoxy group on cellulose acetate and residual hydroxyl can form hydrogen bond with the isocyanic acid ester bond on urethane, thus improve its mechanical property, and the introducing of acetoxy group, turn increase the wetting ability of lignin polyurethane thus finally to obtain quality homogeneous, good mechanical property and there is the film of excellent hydrophilicity.
beneficial effect:
(1) the present invention improves mechanical property and the hydrophilicity of lignin polyurethane film by directly adding the blended method of cellulose acetate, the pollution to environment is decreased with respect to the wooden method usually improving lignin polyurethane film mechanical property of chemical modification, and avoid the extra consumption that modification brings, practical minimizing raw materials cost, decrease the dependence to petroleum resources, save the energy.
(2) the present invention utilizes the mixed solvent of acetone and DMF preparation, can well dissolved lignin, itself and other reaction raw materials is well mixed, make the film smooth texture prepared homogeneous, and acetone can volatilize very soon after film forming, the time that static solidification is used can be greatly reduced, than simple use DMF or tetrahydrofuran (THF) more efficient as solvent.
(4) the cellulose acetate modified lignin resin polyurethane film that prepared by the present invention is compared normal wood quality polyurethane film than the tensile strength of traditional lignin polyurethane film and is improved about about 30%, Young's modulus brings up to 2 ~ 3 times, thus improves the mechanical property of lignin polyurethane film.
(5) cellulose acetate modified lignin resin polyurethane film normal wood quality polyurethane film compared with the average contact angle of ultrapure water that prepared by the present invention reduces about 23%, namely compare conventional polyurethanes film and have better wetting ability, expand the range of application of lignin polyurethane film.
Accompanying drawing explanation
Fig. 1 be without cellulose acetate lignin polyurethane film and be added with the scanning electron microscope (SEM) photograph that surface of fracture that cellulose acetate content is respectively the cellulose acetate wood composite quality polyurethane film of 20% and 40% amplifies 200 times, as can be seen from Figure, along with the increase of cellulose acetate content, cellulose acetate distribution in the film (circle spot) becomes large, is namely separated more and more obvious.
Fig. 2 is the DSC figure of cellulose acetate modified lignin resin polyurethane film.From in figure, along with the increase of cellulose acetate content, the Tg of polyurethane film increases gradually, and when cellulose acetate content reaches 20%, Tg reaches maximum.Major cause is the increase of the hydrogen bond that the increase of cellulose acetate content causes being formed between cellulose acetate and urethane and the increase of cellulose acetate particle, the mobility of polyurethane flexible section is caused to be deteriorated, thus cause the Tg of film to increase, but the increase of cellulose acetate particle can cause again the link between urethane soft or hard section to weaken, thus when cellulose acetate content is more than 20%, Tg reduces gradually.
Fig. 3 is the tensile stress-strain performance of cellulose acetate content on polyurethane film and the impact of Young's modulus.As we can see from the figure, tensile strength and Young's modulus increase along with the increase of cellulose acetate content, when cellulose acetate content reaches 20%, tensile strength reaches maximum, result conforms to the impact of cellulose acetate content on the Tg of film, and elongation rate of tensile failure reduces along with the increase of cellulose acetate content.
The impact of Fig. 4 contact angle to be cellulose acetate content to contact 3s to polyurethane film during with ultrapure water.Along with the increase of cellulose acetate content, the contact angle of lignin polyurethane film and ultrapure water contact angle reduces, and namely the hydrophilicity of polyurethane film increases.When cellulose acetate content is increased to 40%, polyurethane film reduces 23% with the contact angle of ultrapure water than the lignin polyurethane film not adding cellulose acetate.
Embodiment
Following examples further illustrate content of the present invention, but should not be construed as limitation of the present invention.Without departing from the spirit and substance of the case in the present invention, the amendment do the inventive method, step or condition and replacement, all belong to scope of the present invention.
If do not specialize, the conventional means that technique means used in embodiment is well known to those skilled in the art.
raw material sources:
Enzymolysis xylogen is provided by Shandong company of Long Li company, and its number-average molecular weight is 1200 ~ 2200g/mol, and total hydroxy radical content is about 4.1mmol/g.
Cellulose acetate is bought from Aladdin reagent company limited.
Tolylene diisocyanate (TDI) is bought from West Asia reagent, is chemical pure;
Cetomacrogol 1000 (PEG1000) is bought from Chemical Reagent Co., Ltd., Sinopharm Group, is chemical pure;
Acetone is bought from Nanjing Chemistry Reagent Co., Ltd., is analytical pure;
Dimethyl formamide (DMF) is bought from Tianjin Tian Yi Science and Technology Development Co., Ltd., is analytical pure.
detection method:
1, scanning electron microscope analysis adopts in HIT S3400N-1 type scanning electronic microscope and observes sample breakage face, and electron accelerating voltage is 25KV.
2, DSC measures the DiamondDSC type differential scanning calorimeter adopting PerkinElmer company of the U.S..Amount of samples: 2 ~ 5mg; Temperature elevating range :-60 DEG C ~ 150 DEG C; Temperature rise rate: 20 DEG C/min; Type carrier gases: nitrogen; Carrier gas flux: 20mL/min.For avoiding or reducing sample thermal history as far as possible to the impact of DSC data, this experiment is when carrying out DSC thermal analyses, and the data obtained when taking turns temperature programming with second are as the criterion.
3, the test of tensile property uses and newly thinks carefully CMT-4304 type electronic universal material testing machine, tests under room temperature (25 DEG C) and normal atmosphere conditions.Tensile property presses the mensuration of GBT528-2009 vulcanized rubber or thermoplastic elastomer tensile stress-strain performance, and testing sample is dumb-bell shape style, and total length is 100mm, and crevice length is 25mm, and narrow parallel width is 5mm, and trial speed is 200mm/min.Tensile strength and elongation at break data are all the mean value at least three parallel sample.
4, contact angle test adopts the DSA100 type contact angle instrument of German Kruss company to measure, the surfacing of film, and is fitted in veneer surface.
embodiment 1
Take 4g enzymolysis xylogen to be dissolved in the mixed solvent of 40mL acetone and 60mLDMF, and add 16gPEG1000 at 60 DEG C of stirring 0.5h, make it fully mix.The TDI of 6.53g is added, stir, pour in Teflon mould after confined reaction 1h at 75 DEG C, mould is inserted on a horizontal stand, leave standstill 24h, the film of gained is put into after baking oven dries 3h at 80 DEG C, in water, soak 24h under room temperature, finally put into baking oven 120 DEG C of further slakings of 3h, take out diaphragm (LPU), put into vacuum drying oven, in order to further testing its various performance.
embodiment 2
Take 4g enzymolysis xylogen and 1g cellulose acetate is dissolved in the mixed solvent of 40mL acetone and 60mLDMF, and add 15gPEG1000 and stir 0.5h at 60 DEG C, make it fully mix.The TDI of 6.59g is added, stir, pour in Teflon mould after confined reaction 1h at 75 DEG C, mould is inserted on a horizontal stand, leave standstill 24h, the film of gained is put into after baking oven dries 3h at 80 DEG C, in water, soak 24h under room temperature, finally put into baking oven 120 DEG C of further slakings of 3h, take out diaphragm (LPU-CA1), put into vacuum drying oven, in order to further testing its various performance.
embodiment 3
Take 4g enzymolysis xylogen and 2g cellulose acetate is dissolved in the mixed solvent of 40mL acetone and 60mLDMF, and add 14gPEG1000 and stir 0.5h at 60 DEG C, make it fully mix.The TDI of 6.64g is added, stir, pour in Teflon mould after confined reaction 1h at 75 DEG C, mould is inserted on a horizontal stand, leave standstill 24h, the film of gained is put into after baking oven dries 3h at 80 DEG C, in water, soak 24h under room temperature, finally put into baking oven 120 DEG C of further slakings of 3h, take out diaphragm (LPU-CA2), put into vacuum drying oven, in order to further testing its various performance.
embodiment 4
Take 4g enzymolysis xylogen and 3g cellulose acetate is dissolved in the mixed solvent of 40mL acetone and 60mLDMF, and add 13gPEG1000 and stir 0.5h at 60 DEG C, make it fully mix.The TDI of 6.69g is added, stir, pour in Teflon mould after confined reaction 1h at 75 DEG C, mould is inserted on a horizontal stand, leave standstill 24h, the film of gained is put into after baking oven dries 3h at 80 DEG C, in water, soak 24h under room temperature, finally put into baking oven 120 DEG C of further slakings of 3h, take out diaphragm (LPU-CA3), put into vacuum drying oven, in order to further testing its various performance.
embodiment 5
Take 4g enzymolysis xylogen and 4g cellulose acetate is dissolved in the mixed solvent of 40mL acetone and 60mLDMF, and add 12gPEG1000 and stir 0.5h at 60 DEG C, make it fully mix.The TDI of 6.75g is added, stir, pour in Teflon mould after confined reaction 1h at 75 DEG C, mould is inserted on a horizontal stand, leave standstill 24h, the film of gained is put into after baking oven dries 3h at 80 DEG C, in water, soak 24h under room temperature, finally put into baking oven 120 DEG C of further slakings of 3h, take out diaphragm (LPU-CA4), put into vacuum drying oven, in order to further testing its various performance.
The test data of embodiment 1-5 as table 1 successively shown in:
Table 1
| Sample | Enzymolysis xylogen content/% a | Cellulose acetate content/% a | Isocyanate index | Elongation rate of tensile failure/% | Tensile strength/MPa | Glass transition temperature/DEG C | Contact angle/° |
| LPU | 30 | 0 | 1.55 | 252.98 | 5.88 | -24.66 | 89.86 |
| LPU-CA1 | 30 | 10 | 1.55 | 213.51 | 6.69 | -17.77 | 86.91 |
| LPU-CA2 | 30 | 20 | 1.55 | 158.38 | 7.61 | ?14.23 | 82.14 |
| LPU-CA3 | 30 | 30 | 1.55 | 139.92 | 7.47 | ?15.64 | 75.31 |
| LPU-CA4 | 30 | 40 | 1.55 | 109.71 | 6.93 | ?15.55 | 69.27 |
A: relative to the mass percentage of PEG1000.
Claims (1)
1. the preparation method of cellulose acetate modified lignin resin polyurethane film, it is characterized in that step is: take 4g enzymolysis xylogen and 2g cellulose acetate is dissolved in the mixed solvent of 40mL acetone and 60mLDMF, and add 14gPEG1000 at 60 DEG C of stirring 0.5h, make it fully mix; The TDI of 6.64g is added, stir, pour in Teflon mould after confined reaction 1h at 75 DEG C, mould is inserted on a horizontal stand, leave standstill 24h, the film of gained is put into after baking oven dries 3h at 80 DEG C, 24h is soaked under room temperature in water, finally put into baking oven 120 DEG C of further slakings of 3h, take out diaphragm, put into vacuum drying oven and preserve.
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| CN105601985B (en) * | 2016-03-27 | 2019-06-18 | 华南理工大学 | A kind of lignin melamine primary surface hydrophobic foam and preparation method thereof |
| CN114409921B (en) * | 2022-02-22 | 2022-11-18 | 华南农业大学 | Modified lignin polyol and preparation method of polyurethane hot melt adhesive thereof |
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| CN101928373A (en) * | 2010-08-27 | 2010-12-29 | 华南理工大学 | Plant fiber component-based polyalcohol and preparation method thereof |
| CN103183801A (en) * | 2013-03-20 | 2013-07-03 | 中国林业科学研究院林产化学工业研究所 | Method for preparing polyurethane film by CIMV wheat straw lignin |
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| CN101928373A (en) * | 2010-08-27 | 2010-12-29 | 华南理工大学 | Plant fiber component-based polyalcohol and preparation method thereof |
| CN103183801A (en) * | 2013-03-20 | 2013-07-03 | 中国林业科学研究院林产化学工业研究所 | Method for preparing polyurethane film by CIMV wheat straw lignin |
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