CN106496508A - The method that hyper-branched polyester grafting Folium Agaves Sisalanae crystallite prepares modified shape memory polyurethane - Google Patents
The method that hyper-branched polyester grafting Folium Agaves Sisalanae crystallite prepares modified shape memory polyurethane Download PDFInfo
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- CN106496508A CN106496508A CN201611066703.XA CN201611066703A CN106496508A CN 106496508 A CN106496508 A CN 106496508A CN 201611066703 A CN201611066703 A CN 201611066703A CN 106496508 A CN106496508 A CN 106496508A
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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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3215—Polyhydroxy compounds containing aromatic groups or benzoquinone groups
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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
- C08G18/28—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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- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
- D21C5/00—Other processes for obtaining cellulose, e.g. cooking cotton linters ; Processes characterised by the choice of cellulose-containing starting materials
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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
- C08G2280/00—Compositions for creating shape memory
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention discloses a kind of method that hyper-branched polyester grafting Folium Agaves Sisalanae crystallite prepares modified shape memory polyurethane.Folium Agaves Sisalanae crystallite and end carboxyl super branched polyester are prepared respectively, the two remixes reaction and hyper-branched polyester grafting Folium Agaves Sisalanae crystallite is obtained, polycaprolactone diols is heated to 80 DEG C and magnetic agitation under nitrogen atmosphere until melting, it is subsequently adding N, N dimethylformamides and dibutyl tin laurate, it is heated to 105 DEG C of insulation 15min eliminating waters, 80 DEG C are cooled to again, add hexamethylene diisocyanate, 3 ~ 5h is reacted at 80 DEG C, the mixed liquor containing isocyanate terminated base polyurethane prepolymer for use as is obtained, add obtained hyper-branched polyester grafting Folium Agaves Sisalanae crystallite and 4, 4 ' '-biphenyl diphenols, stirring reaction in blanket of nitrogen, 8 ~ the 10h that is heating and curing is subsequently poured in preheated mould, hyper-branched polyester grafting Folium Agaves Sisalanae crystallite modification shape memory polyurethane is obtained.The inventive method is simple to operate, and gained shape memory polyurethane material has excellent mechanics, calorifics and shape-memory properties.
Description
Technical field
The invention belongs to intelligent macromolecule material technical field, more particularly to a kind of hyper-branched polyester grafting Folium Agaves Sisalanae crystallite system
The method of standby modification shape memory polyurethane.
Background technology
Shape-memory material has important using value in bio-medical field, structural member field, field of textiles, is near
The study hotspot and emphasis of academia and industrial quarters over year.Especially shape memory high molecule（Shape Memory Polymer,
Abbreviation SMP）Material has the advantages that easy processing, easy-formation, light weight, with very huge potential using value, from the eighties
Start, the research worker of countries in the world increases the input to SMP and research so that the research of SMP has obtained quick development,
Become when the important functional material of former.
It is used for researching and developing one of material of SMP, shape memory polyurethane as early start（Shape Memory
Polyurethane, abbreviation SMPU）From the eighties by Mitsubishi heavy industry commercial development success after obtained extensive concern.Poly-
Urethane is as chain extender by polyisocyanates and polyether polyol or PEPA and small molecule polyol, polyamine etc.
In a kind of polymer prepared by raw material.In the polymer, the chain rigidity of NCO and chain extender shows as hard section, between hard section
Hydrogen bond and other chain windings effect can play a part of physical crosslinking in SMP, and polyester or polyether Glycols are soft
Section, then can play a part of molecular switch.So, the structure design of soft and hard segments and proportion adjustment prepare high-performance SMPU
Key point.
In recent years, with the enhancing of people's environmental consciousness, ecological and protection of resources consciousness is also constantly being lifted.Using each
The research of fibre modification polymer matrix composite is planted, becomes the focus of material science research.As natural fiber has source
Extensively, little, nontoxic, the high intensity of density and modulus, be easy to surface modification and lower-price characteristic, therefore, using various
Plant resourceses residue carrys out enhancing modified polymer matrix composite and is rapidly developed.
Folium Agaves Sisalanae is a kind of common Agave perennation plant, is mainly grown in the minorities such as Brazil, Kenya, China
Country, the country are mainly distributed on the ground such as Guangxi, Guangdong and Hainan, up to 4,500,000 tons of the annual yield in the whole world.Sisal hemp leaf is included
Have an abundant crude fibre, the content of cellulose up to 50%～74%, about 150～200 μm of fibre diameter, every fiber is by several
Empty tubule composition, the surface of fiber is squama time shape, rough and uneven in surface, is not easily stripped after being combined with resin matrix, non-in sisal fiber
Resin-based reinforcing material is often suitable as.Compared with other cellulose crystallites, sisal fiber crystallite has strong but pliable in texture, high-strength
Degree, high-moduluss, rub resistance, acid and alkali-resistance and low temperature resistant the advantages of, many special dimensions have other fibers irreplaceable excellent
More property, is preferable polymer-based reinforcement material.
Cellulose crystallite is a kind of natural polymer micro crystal material of renewable, degradable, with big specific surface area, can
The features such as pressure property, water absorption, good reactivity worth and function, it is widely used in food and drink, daily-use chemical industry, medicine
The field such as health and light industry.Meanwhile, cellulose crystallite also has high-moduluss, low-density, heat-resist and polymer matrix body phase
The advantages of capacitive is good, can be used to improve the mechanical property of polymer and hot property.
The method comprises the steps of firstly, preparing going out hyper-branched polyester grafting Folium Agaves Sisalanae crystallite, then by MOLECULE DESIGN, hyper-branched polyester is connect
Branch Folium Agaves Sisalanae crystallite is incorporated in " PCL+HDI+BP " system, prepares the good modified SMPU of combination property.This thinking is at present not
See document report.
Content of the invention
It is an object of the invention to provide a kind of hyper-branched polyester grafting Folium Agaves Sisalanae crystallite prepares modified shape memory polyurethane
Method.
Concretely comprise the following steps：
(1) Folium Agaves Sisalanae fibril is cut into the length of long 5 ± 0.1cm, and the removal of impurity is gone in then washing, and 80 DEG C of drying are obtained and dry Folium Agaves Sisalanae original
Fibre, stand-by.
(2) weigh that 10g steps (1) are obtained to be dried Folium Agaves Sisalanae fibril and be added in 200mL reactors, add 100mL pH
It is worth the hydrochloric acid solution for 3 ± 0.1, at 165 DEG C, reacts 40 ~ 45min, it is colourless to be then washed to filtrate, gained Folium Agaves Sisalanae fibril is squeezed
It is added to after pressing dry moisture in 200mL reactors, adds 4gNaOH, 4gNa2SO4·10H2O and 100mL water mixed dissolutions, in
2h is reacted at 170 DEG C, and sucking filtration washs constant to filtrate color, obtains dry Folium Agaves Sisalanae, standby.
(3) dry Folium Agaves Sisalanae obtained in step (2) is added in 500mL there-necked flasks, add 3.35g sodium chlorite,
325mL water and 2.5mL mass percent concentrations are 36 ~ 38% acetic acid, are heated to reacting 2h at 75 ~ 80 DEG C, using high-purity washing
Sucking filtration is washed, is then dried to constant weight at 75 DEG C, Folium Agaves Sisalanae crystallite is obtained.
(4) by 1.5 grams of N, N- dicyclohexylcarbodiimides are dissolved in 8 milliliters of DMFs, in N2Protect
Progressively it is added drop-wise under shield in 100 milliliters of there-necked flasks equipped with 8 milliliters of tetrahydrofurans and 4 grams of malic acids, stirring reaction at 25 DEG C
After 12 hours, filter, remove pale precipitation thing, filtrate obtains faint yellow oily dope, as holds after solvent is distilled off
Carboxyl super branched polyester.
(5) in 100 milliliters of there-necked flasks, 2 ~ 4 grams of steps (3) are added to be obtained obtained in Folium Agaves Sisalanae crystallite, 2 ~ 4 grams of steps (4)
End carboxyl super branched polyester and 5 ~ 7 milliliters of DMFs, in N2In 10 ~ 30 points of 30 ~ 40 DEG C of stirring reactions under protection
Clock, is subsequently adding 0.3 ~ 0.4 gram of DMAP and 5 ~ 7 grams of N, and N- DIC, isothermal reaction 10 are little
When, filter, dry, that is, hyper-branched polyester grafting Folium Agaves Sisalanae crystallite is obtained.
(6) polycaprolactone diols that 2.0g weight average molecular weight is 1000 is put in round-bottomed flask, under nitrogen atmosphere plus
Heat is to 80 DEG C and magnetic agitation is until thawing, is subsequently adding 20ml DMFs（DMF）With 0.1 ml tin dilaurates
Dibutyl tin（DBTDL）, 105 DEG C of insulation 15min eliminating waters are heated the mixture to, then are cooled to 80 DEG C, add 0.67ml six sub-
Methyl diisocyanate（HDI）, 3 ~ 5h is reacted at 80 DEG C, and the mixed liquor containing isocyanate terminated base polyurethane prepolymer for use as is obtained.
(7) hyper-branched polyester grafting Folium Agaves Sisalanae crystallite and 4,4 '-'-biphenyl diphenols of 0.35g obtained in 0.02g steps (5) are added
Enter in the obtained mixed liquor containing isocyanate terminated base polyurethane prepolymer for use as of step (6), stir at 80 DEG C in blanket of nitrogen
Reaction 10h, is then poured in preheated mould at 60 ~ 80 DEG C together, and be heating and curing at 70 ~ 90 DEG C 8 ~ 10h, that is, be obtained super
Branched polyester grafting Folium Agaves Sisalanae crystallite modification shape memory polyurethane.
The inventive method is simple to operate, and obtained modified shape memory polyurethane material has excellent mechanics, heat
Learn and shape-memory properties.Its main performance index is as follows：Highest elongation at break reaches 1000%；Tensile strength is up to
30.89Mpa；5% thermal weight loss temperature >=275 DEG C；Shape recovery rate is 95% ~ 100%.
Specific embodiment
Embodiment：
(1) Folium Agaves Sisalanae fibril is cut into the length of long 5cm, and the removal of impurity is gone in then washing, and 80 DEG C of drying are obtained and dry Folium Agaves Sisalanae fibril, treat
With.
(2) weigh that 10g steps (1) are obtained to be dried Folium Agaves Sisalanae fibril and be added in 200mL reactors, add 100mL pH
It is worth the hydrochloric acid solution for 3, at 165 DEG C, reacts 42min, it is colourless to be then washed to filtrate, gained Folium Agaves Sisalanae fibril extruding stem moisture
After be added in 200mL reactors, add 4gNaOH, 4gNa2SO4·10H2O and 100mL water mixed dissolutions, at 170 DEG C
Reaction 2h, sucking filtration washs constant to filtrate color, obtains dry Folium Agaves Sisalanae, standby.
(3) dry Folium Agaves Sisalanae obtained in step (2) is added in 500mL there-necked flasks, add 3.35g sodium chlorite,
325mL water and the acetic acid that 2.5mL mass percent concentrations are 37%, are heated to reacting 2h at 78 DEG C, are taken out using high-purity water washing
Filter, then dries to constant weight at 75 DEG C, and Folium Agaves Sisalanae crystallite is obtained.
(4) by 1.5 grams of N, N- dicyclohexylcarbodiimides are dissolved in 8 milliliters of DMFs, in N2Protect
Progressively it is added drop-wise under shield in 100 milliliters of there-necked flasks equipped with 8 milliliters of tetrahydrofurans and 4 grams of malic acids, stirring reaction at 25 DEG C
After 12 hours, filter, remove pale precipitation thing, filtrate obtains faint yellow oily dope, as holds after solvent is distilled off
Carboxyl super branched polyester.
(5) in 100 milliliters of there-necked flasks, add 3 grams of steps (3) that end carboxylic obtained in Folium Agaves Sisalanae crystallite, 3 grams of steps (4) is obtained
Base hyper-branched polyester and 6 milliliters of DMFs, in N2In 35 DEG C of stirring reactions 20 minutes under protection, it is subsequently adding
0.35 gram of DMAP and 6 grams of N, N- DIC, isothermal reaction 10 hours are filtered, and are dried, that is, are made
Obtain hyper-branched polyester grafting Folium Agaves Sisalanae crystallite.
(6) polycaprolactone diols that 2.0g weight average molecular weight is 1000 is put in round-bottomed flask, under nitrogen atmosphere plus
Heat is to 80 DEG C and magnetic agitation is until thawing, is subsequently adding 20ml DMFs（DMF）With 0.1 ml tin dilaurates
Dibutyl tin（DBTDL）, 105 DEG C of insulation 15min eliminating waters are heated the mixture to, then are cooled to 80 DEG C, add 0.67ml six sub-
Methyl diisocyanate（HDI）, 4h is reacted at 80 DEG C, and the mixed liquor containing isocyanate terminated base polyurethane prepolymer for use as is obtained.
(7) hyper-branched polyester grafting Folium Agaves Sisalanae crystallite and 4,4 '-'-biphenyl diphenols of 0.35g obtained in 0.02g steps (5) are added
Enter in the obtained mixed liquor containing isocyanate terminated base polyurethane prepolymer for use as of step (6), stir at 80 DEG C in blanket of nitrogen
Reaction 10h, is then poured in preheated mould at 70 DEG C together, and be heating and curing at 80 DEG C 9h, that is, hyper-branched polyester is obtained
Grafting Folium Agaves Sisalanae crystallite modification shape memory polyurethane.
Hyper-branched polyester grafting Folium Agaves Sisalanae crystallite modification shape memory polyurethane obtained in the present embodiment is tested, which breaks
It is 1000% to split percentage elongation, and tensile strength is 30.89MPa；Shape recovery rate is 96.39%；5% thermal weight loss temperature is 276 DEG C,
Combination property is more excellent.
Claims (1)
1. a kind of method that hyper-branched polyester grafting Folium Agaves Sisalanae crystallite prepares modified shape memory polyurethane, it is characterised in that concrete step
Suddenly it is：
(1) Folium Agaves Sisalanae fibril is cut into the length of long 5 ± 0.1cm, and the removal of impurity is gone in then washing, and 80 DEG C of drying are obtained and dry Folium Agaves Sisalanae original
Fibre, stand-by；
(2) weigh that 10g steps (1) are obtained to be dried Folium Agaves Sisalanae fibril and be added in 200mL reactors, adding 100mL pH value is
3 ± 0.1 hydrochloric acid solution, reacts 40 ~ 45min at 165 DEG C, and it is colourless to be then washed to filtrate, gained Folium Agaves Sisalanae fibril extruding stem
It is added to after moisture in 200mL reactors, adds 4gNaOH, 4gNa2SO4·10H2O and 100mL water mixed dissolutions, in 170
2h is reacted at DEG C, and sucking filtration washs constant to filtrate color, obtains dry Folium Agaves Sisalanae, standby；
(3) dry Folium Agaves Sisalanae obtained in step (2) is added in 500mL there-necked flasks, adds 3.35g sodium chlorite, 325mL water
Be 36 ~ 38% acetic acid with 2.5mL mass percent concentrations, be heated to 2h being reacted at 75 ~ 80 DEG C, using high-purity water washing sucking filtration,
Then dry to constant weight at 75 DEG C, Folium Agaves Sisalanae crystallite is obtained；
(4) by 1.5 grams of N, N- dicyclohexylcarbodiimides are dissolved in 8 milliliters of DMFs, in N2Under protection by
Step is added drop-wise in 100 milliliters of there-necked flasks equipped with 8 milliliters of tetrahydrofurans and 4 grams of malic acids, stirring reaction 12 hours at 25 DEG C
Afterwards, filter, remove pale precipitation thing, filtrate obtains faint yellow oily dope after solvent is distilled off, as end carboxyl surpasses
Branched polyester；
(5) in 100 milliliters of there-necked flasks, add 2 ~ 4 grams of steps (3) that end carboxylic obtained in Folium Agaves Sisalanae crystallite, 2 ~ 4 grams of steps (4) is obtained
Base hyper-branched polyester and 5 ~ 7 milliliters of DMFs, in N2In 30 ~ 40 DEG C of stirring reactions 10 ~ 30 minutes under protection,
It is subsequently adding 0.3 ~ 0.4 gram of DMAP and 5 ~ 7 grams of N, N- DIC, isothermal reaction 10 hours, mistake
Filter, dries, that is, hyper-branched polyester grafting Folium Agaves Sisalanae crystallite is obtained；
(6) polycaprolactone diols that 2.0g weight average molecular weight is 1000 is put in round-bottomed flask, is heated under nitrogen atmosphere
80 DEG C and magnetic agitation are subsequently adding 20ml DMFs and 0.1 ml dibutyl tin laurates until melt,
105 DEG C of insulation 15min eliminating waters are heated the mixture to, then is cooled to 80 DEG C, add 0.67ml hexamethylene diisocyanates, in
3 ~ 5h is reacted at 80 DEG C, and the mixed liquor containing isocyanate terminated base polyurethane prepolymer for use as is obtained；
(7) hyper-branched polyester grafting Folium Agaves Sisalanae crystallite and 4,4 '-'-biphenyl diphenols of 0.35g obtained in 0.02g steps (5) are added to
In the obtained mixed liquor containing isocyanate terminated base polyurethane prepolymer for use as of step (6), in blanket of nitrogen at 80 DEG C stirring reaction
10h, is then poured in preheated mould at 60 ~ 80 DEG C together, and be heating and curing at 70 ~ 90 DEG C 8 ~ 10h, that is, be obtained hyperbranched
Polyester graft Folium Agaves Sisalanae crystallite modification shape memory polyurethane.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112094397A (en) * | 2020-09-23 | 2020-12-18 | 广东石油化工学院 | Preparation method of sisal hemp based shape memory polyurethane foam |
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|---|---|---|---|---|
| CN103951830A (en) * | 2014-05-25 | 2014-07-30 | 桂林理工大学 | Preparation method of hyperbranched polyester graft modified sisal fiber cellulose microcrystal |
| CN105622888A (en) * | 2016-03-28 | 2016-06-01 | 桂林理工大学 | Method for preparing shape memory polymer material with high strength and low response temperature |
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2016
- 2016-11-29 CN CN201611066703.XA patent/CN106496508A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103951830A (en) * | 2014-05-25 | 2014-07-30 | 桂林理工大学 | Preparation method of hyperbranched polyester graft modified sisal fiber cellulose microcrystal |
| CN105622888A (en) * | 2016-03-28 | 2016-06-01 | 桂林理工大学 | Method for preparing shape memory polymer material with high strength and low response temperature |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112094397A (en) * | 2020-09-23 | 2020-12-18 | 广东石油化工学院 | Preparation method of sisal hemp based shape memory polyurethane foam |
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