CN104479318B - A kind of Biodegradable aliphatic-aromatic copolyester compositions and application thereof - Google Patents
A kind of Biodegradable aliphatic-aromatic copolyester compositions and application thereof Download PDFInfo
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Abstract
The invention discloses a kind of biodegradable fatty race aromatic copolyester compositions, by mass percentage, comprise following components: A:69.95% ~ 89.95% contains alkyl/alkyloxy side chain aliphatic aromatic copolyesters；B:10% ~ 30% polylactic acid；C:0.05% ~ 3% compatilizer；Described A by mass percentage, comprises following components: A1:44% ~ 60% aromatic polyester unit；A2:39% ~ 55% straight-chain aliphatic polyester unit；A3:0.3% ~ 3% contains alkyl/alkyloxy side chain fatty group dibasic acid unit；In the biodegradable fatty race aromatic copolyester compositions of the present invention due to add specific proportioning containing alkyl/alkyloxy side chain fatty group dibasic acid unit, the yield strength making the thin film made is improved, be conducive to improving agricultural mulching tolerant crops and the puncture resistance of weeds, reduce the probability that holes phenomenon occurs；And OTR oxygen transmission rate improves, moisture-vapor transmission reduces, and the thin film made is used as during agricultural mulching have preferably insulation, moisture-keeping function.
Description
Technical field
The invention belongs to polymer blend technical field, particularly to a kind of biodegradation containing alkyl/alkyloxy side chain
Aliphatic-aromatic copolyester compositions and the application in agricultural film industry thereof.
Background technology
At present, the mulch film great majority used in agricultural production are synthetic polymers, such as polyethylene (PE), polrvinyl chloride
(PVC) etc..While using these film material to bring certain economic benefit to agricultural, also cause serious to environment
White pollution.These materials are the long-term stable existence of meeting in natural environment, remains in the mulch film debris damage soil in soil in a large number
Earth structure, makes soil hardening, hinders crop to absorb water and fertilizer from soil, and life-time service causes crop production reduction.From Tanaka
Mulch film workload is big, cost is high in recovery, and is difficult to reclaim mulch film completely.Through long-time accumulation, mulch film relic can drop significantly
The quality of low soil.
Biodegradable fatty race-aromatic polyester has high-flexibility, good impact strength, and good molding and adds
Work performance.But its stiffness of thin film made is relatively low.By by itself and polylactic acid blend, it is possible to improve the excellent thin film of deflection and produce
Product.And can be in the natural environment in field, under the effect of water and microorganism, complete in the time about some months to several years
Degradable, end product is water and carbon dioxide, is the ideal material making mulch film.
But, the tear-resistant ability of common linear aliphatic race-aromatic copolyester (such as PBAT etc.) and PLA blend is not
, easily there is holes as during mulch film under the effects such as weeds in foot, causes insulation, moistening effect to reduce.
Summary of the invention
In order to overcome the shortcoming of above-mentioned prior art with not enough, the primary and foremost purpose of the present invention be to provide one containing alkyl/
The Biodegradable aliphatic-aromatic copolyester compositions of alkyloxy side chain.
Another object of the present invention is to provide above-mentioned biodegradable fatty race-aromatic series containing alkyl/alkyloxy side chain common
Polymer blend application in agricultural mulching industry.
The purpose of the present invention realizes by following technical solution:
A kind of Biodegradable aliphatic-aromatic copolyester compositions, by mass percentage, comprises following components:
A: containing alkyl/alkyloxy side chain aliphatic-aromatic copolyester 69.95% ~ 89.95%；
B: polylactic acid 10% ~ 30%；
C: compatilizer 0.05% ~ 3%；
Described A by mass percentage, comprises following components:
A1: aromatic polyester unit 44% ~ 60%；
A2: straight-chain aliphatic polyester unit 39% ~ 55%；
A3: containing alkyl/alkyloxy side chain fatty group dibasic acid unit 0.3% ~ 3%.
Described A3 is to react prepared containing alkyl/alkyloxy side chain aliphatic dibasic acid or ester with dihydroxy compounds；Institute
State and containing alkyl/alkyloxy side chain aliphatic dibasic acid there is following structure:
Wherein R1For alkyl or alkoxyl；
R1During for alkyl, R1It is the alkyl of 4 ~ 12, can be containing the carbon number side chain less than 2, R in R11In containing 0 ~
1 carbon-carbon double bond, carbon-carbon double bond can be at R1Any position；N1 is the integer of 0 ~ 9, and n2 is the integer of 0 ~ 9, and 0≤n1+
n2≤9；
R1During for alkoxyl, there is following structure:
Wherein R3For the one in hydrogen atom, methyl or ethyl, a is the integer of 2 ~ 4, and b is the integer of 1 ~ 6, and 4≤
a×b≤12。
Described A1 is that aromatic acid or ester react with dihydroxy compounds and prepare；Described aromatic acid is selected from
One or more kinds of mixture in p-phthalic acid, M-phthalic acid, phthalic acid or its carboxylate.
Described A2 is that straight-chain aliphatic binary acid or ester react with dihydroxy compounds and prepare；Described straight-chain aliphatic two
Unit's acid is selected from the Straight chain diatomic acid residue containing 3 ~ 10 carbon atoms, preferably malonic acid, succinic acid, 1,3-propanedicarboxylic acid, adipic acid, heptan
One or more kinds of mixture in diacid, suberic acid, Azelaic Acid, decanedioic acid.
Described dihydroxy compounds is selected from the alkyl diol of C2 ~ C6, preferably ethylene glycol, 1,3-PD, Isosorbide-5-Nitrae-fourth two
One or more kinds of mixture in alcohol, 1,5-pentanediol, 1,6-HD.
The described degree of randomness containing alkyl/alkyloxy side chain aliphatic-aromatic copolyester is 0.8 ~ 1.2, described degree of randomness
Obtained by 1H NMR test result calculations, method of testing reference computational methods reference " New Chemical Materials " volume 2012,40,12
Phase, p85 ~ 93.
The described intrinsic viscosity containing alkyl/alkyloxy side chain aliphatic-aromatic copolyester is 1.2 ~ 1.4dL/g, described
Intrinsic viscosity records with reference to GB/T1632.5-2008, and test temperature is 25oC, solvent is phenol/o-dichlorohenzene (60/40, wt/
Wt), the concentration of copolyesters is 0.5g/100mL, records with Ubbelohde viscometer.
The described melt mass flow rate containing alkyl/alkyloxy side chain aliphatic-aromatic copolyester is 2 ~ 5g/
10min, described melt mass flow rate records with reference to GB/T 3682-2000, and temperature is 190oC, load is 2.16Kg.
The described fusing point containing alkyl/alkyloxy side chain aliphatic-aromatic copolyester is 115oC~150oC；Described fusing point is joined
Record according to GB/T 19466.3-2004.
The above-mentioned preparation method containing alkyl/alkyloxy side chain aliphatic-aromatic copolyester:
1) Biodegradable aliphatic-aromatic copolyester can directly be prepared by conventional vacuum fusion polymerization；
2) can also first prepare the prepolymer P0 that intrinsic viscosity is 0.9 ~ 1.1dL/g, then obtain biological by chain extension legal system
Degrading aliphatic-aromatic copolyester.Wherein, chain extender can use difunctional isocyanates；Described difunctional isocyanide
Acid esters is selected from 2,6-toluene di-isocyanate(TDI), 2,4 toluene diisocyanate, '-diphenylmethane diisocyanate, 1,6-hexa-methylene
The mixture of one or more in diisocyanate, isoflurane chalcone diisocyanate.
The preparation method of described Biodegradable aliphatic-aromatic copolyester compositions:
Mix above-mentioned in high mixer containing alkyl/alkyloxy side chain aliphatic-aromatic copolyester, polylactic acid and compatilizer
After even, add in double screw extruder with weighing balance, in 170 ~ 220oC extruding pelletization i.e. can get biodegradable fatty race-virtue
Fragrant race polyester composition.
Can be containing the stabilizer of not more than 1% in Biodegradable aliphatic-aromatic copolyester compositions, stabilizer selects
More than the one or two kinds of in Hinered phenols stabilizer, phosphite-type stabilisers, amines stabilizer, thioether class stabilizer
Mixture.
Above-mentioned Biodegradable aliphatic-aromatic copolyester compositions can by the processing modes such as blowing make thin film,
Sack etc..The thin film made by Biodegradable aliphatic-aromatic copolyester compositions can serve as agricultural mulching.
The present invention compared with prior art, has the advantages that
1) in the Biodegradable aliphatic-aromatic copolyester compositions of the present invention due to add specific proportioning containing alkane
Base/alkyloxy side chain fatty group dibasic acid unit so that the yield strength of the thin film made is improved, and is conducive to improving agriculture
With mulch film tolerant crops and the puncture resistance of weeds, reduce the probability that holes phenomenon occurs；
2) the tear-resistant intensity of the thin film that the Biodegradable aliphatic-aromatic copolyester compositions of the present invention is made and falling
The damaged quality of mark impact is improved, and prevents thin film from holes occur during being conducive to using；
3) OTR oxygen transmission rate of the Biodegradable aliphatic-aromatic copolyester compositions of the present invention improves, and steam is saturating
Rate of crossing reduces, and the thin film made is used as during agricultural mulching have preferably insulation, moisture-keeping function.
Detailed description of the invention
Further illustrating the present invention below by detailed description of the invention, following example are the present invention preferably embodiment party
Formula, but embodiments of the present invention are not limited by following embodiment.
Now the raw material used by embodiment and comparative example is done as described below, but is not limited to these materials:
P-phthalic acid (PTA): high-class product, raises sub-petrochemical industry and produces；
Dimethyl terephthalate (DMT) (DMT): high-class product, Japan Supreme Being people produces；
BDO (BDO): top grade product, Shanxi three-dimensional is produced；
Adipic acid (AA): top grade product, Daqing petrochemical is produced；
Polylactic acid (PLA): purchased from Natureworks；
Compatilizer is purchased to BASF, and the trade mark is ADR-4370, ADR-4300, ADR-4380, ADR-4368, ADR-4385 etc.；
Other raw material, if titanate esters, dodecenylsuccinic acid (T746), octenyl succinic anhydride (ASA) are commercially available industry
Level product；
Other is containing the method for alkyl/alkyloxy side chain aliphatic diacid reference " petrochemical industry " 1993,10, p675 ~ 678
Synthesis.
Preparation containing alkyl/alkyloxy side chain aliphatic-aromatic copolyester A:
Embodiment A1
By dimethyl terephthalate (DMT) 8.73 Kg, BDO 9 Kg, put in reactor, use nitrogen displacement reaction
After air in still, it is warming up to 170 DEG C, after dimethyl terephthalate (DMT) is completely melt, adds isopropyl titanate 10 g, gradually
It is warming up to 180 DEG C and carries out esterification.After the methanol slipped out reaches theoretical amount, add adipic acid 7.96 Kg, laurylene base fourth
Diacid 142 g, continues reaction to slipping out after water reaches theoretical amount, adds isopropyl titanate 10g, be gradually heating to 230 ~ 250 DEG C,
Reacting kettle inner pressure is reduced to below 60Pa by about 30min, and continuation reaction reaches to set to stirring motor power with this understanding
Definite value.In reactor, it is filled with high pure nitrogen, obtains containing alkyl/alkoxyl side through tie rod, pelletizing after melt per os is molded out
Chain fatty race-aromatic copolyester.
Embodiment A2
By dimethyl terephthalate (DMT) 11.64Kg, 1,4-butanediol 9Kg, adipic acid 5.40Kg, octenyl succinic anhydride
630g puts in reactor, is gradually heating to 170oC, adds tetrabutyl titanate 20g, and first alcohol and water to be slipped out reaches theoretical amount
After, it is gradually heating to 230 ~ 250oReacting kettle inner pressure is reduced to below 60Pa by C, about 30min, and continues anti-with this understanding
Setting value should be reached to stirring motor power；In reactor, be filled with high pure nitrogen, after melt per os is molded out through tie rod, cut
Grain obtains copolyesters base material A 20；After A20 is dried, at double screw extruder after mixing with 0.6% hexamethylene diisocyanate
Middle reaction, obtains containing alkyl side chain aliphatic-aromatic copolyester through pelletizing.
The middle aromatic acid that feeds intake, aliphatic dibasic acid is changed fatty with containing alkyl/alkyloxy side chain by the proportioning of table 1
The ratio of race's diacid, according to above-described embodiment A1 or the preparation method of embodiment A2, can prepare different containing alkyl/alkane
Epoxide pendent fatty race-aromatic copolyester A.
Table 1 contains proportioning and the performance test results of alkyl/alkyloxy side chain aliphatic-aromatic copolyester A
Wherein, the preparation method of B4 is: prepare polybutylene terephthalate (PBT) prepolymer, polyadipate fourth the most respectively
Diol ester prepolymer, the prepolymer of poly-dodecenylsuccinic acid butanediol, be subsequently adding hexamethylene diisocyanate at double spiral shells
Bar extruder carries out chain extending reaction prepare.
Embodiment 1 ~ 9 and comparative example 1 ~ 4:
Alkyl/alkyloxy side chain aliphatic-aromatic copolyester A, polylactic acid and as compatilizer will be contained by the proportioning of table 2
Compatilizer mix in high mixer after, add in double screw extruder with weighing balance, in 170 ~ 220oC extruding pelletization is given birth to
Thing degrading aliphatic-aromatic copolyester compositions.
The proportioning of table 2 Biodegradable aliphatic-aromatic copolyester compositions P
The performance test results of table 3 Biodegradable aliphatic-aromatic copolyester compositions P
From table 2 and table 3 it can be seen that due to add specific proportioning containing alkyl/alkyloxy side chain aliphatic dibasic acid
Ester units, the thin film yield strength that Biodegradable aliphatic-aromatic copolyester compositions prepares is improved, and is conducive to improving
Agricultural mulching tolerant crops and the puncture resistance of weeds, reduce the probability that holes phenomenon occurs；And the thin film that said composition prepares
Tear-resistant intensity and the mark damaged quality of impact that falls be improved, prevent thin film from holes occurring during being conducive to using；
It addition, the OTR oxygen transmission rate of Biodegradable aliphatic-aromatic copolyester compositions improves, moisture-vapor transmission drops
Low, the thin film made is used as during agricultural mulching have preferably insulation, moisture-keeping function.
Each performance test standard or method:
Intrinsic viscosity records with reference to GB/T1632.5-2008, and test temperature is 25oC, solvent is phenol/o-dichlorohenzene
(60/40, wt/wt), copolyesters A concentration is 0.5g/100mL, records with Ubbelohde viscometer；
Copolyesters1H NMR VARIAN company Mercury300 nuclear magnetic resonance chemical analyser records, and solvent is CDCl3/
CD3COOD(9/1)；
The degree of randomness of copolyesters A by1H NMR test result calculations obtains, and method of testing is with reference to computational methods reference " chemical industry
New material " volume 2012,40,12 phases, p85 ~ 93；
Melt mass flow rate records with reference to GB/T 3682-2000, and temperature is 190oC, load is 2.16Kg；
Fusing point records with reference to GB/T 19466.3-2004；
Film stretchability can record with reference to GB/T 1040.3-2006；
The tear-resistant intensity of thin film records with reference to GB/T 16578.2-2009；
Thin film shock resistance records with reference to GB/T 9639.1-2008；
Film water vapor transmission rates records with reference to ASTM F 1249；
Thin-films Oxygen vapor permeability records with reference to ASTM D 3985.
Film thickness records with reference to GB/T 20220-2006.
Claims (12)
1. a Biodegradable aliphatic-aromatic copolyester compositions, it is characterised in that by mass percentage, comprise with
Lower component:
A: containing alkyl/alkyloxy side chain aliphatic-aromatic copolyester 69.95% ~ 89.95%；
B: polylactic acid 10% ~ 30%；
C: compatilizer 0.05% ~ 3%；
Described A by mass percentage, comprises following components:
A1: aromatic polyester unit 44% ~ 60%；
A2: straight-chain aliphatic polyester unit 39% ~ 55%；
A3: containing alkyl/alkyloxy side chain fatty group dibasic acid unit 0.3% ~ 3%.
Biodegradable aliphatic-aromatic copolyester compositions the most according to claim 1, it is characterised in that described A3
For reacting prepared containing alkyl/alkyloxy side chain aliphatic dibasic acid or ester with dihydroxy compounds；Described containing alkyl/alkoxyl
Pendent fatty race binary acid has a following structure:
Wherein R1For alkyl or alkoxyl；
R1During for alkyl, R1For the alkyl of C4 ~ C12, R1In can containing carbon number less than 2 side chain, R1In containing 0 ~ 1
Carbon-carbon double bond, carbon-carbon double bond can be at R1Any position；N1 is the integer of 0 ~ 9, and n2 is the integer of 0 ~ 9, and 0≤n1+n2
≤9；
R1During for alkoxyl, there is following structure:
Wherein R3For the one in methyl or ethyl, a is the integer of 2 ~ 4, and b is the integer of 1 ~ 6, and 4≤a × b≤12.
Biodegradable aliphatic-aromatic copolyester compositions the most according to claim 1, it is characterised in that described A1
React prepared for aromatic acid or ester with dihydroxy compounds；Described aromatic acid selected from p-phthalic acid,
One or more kinds of mixture in phthalic acid, phthalic acid.
Biodegradable aliphatic-aromatic copolyester compositions the most according to claim 1, it is characterised in that described A2
React prepared for straight-chain aliphatic binary acid or ester with dihydroxy compounds；Described straight-chain aliphatic binary acid selected from containing 3 ~
The Straight chain diatomic acid of 10 carbon atoms.
Biodegradable aliphatic-aromatic copolyester compositions the most according to claim 4, it is characterised in that described directly
Chain fatty race binary acid is in malonic acid, succinic acid, 1,3-propanedicarboxylic acid, adipic acid, 1,5-pentanedicarboxylic acid., suberic acid, Azelaic Acid, decanedioic acid
One or more kinds of mixture.
6., according to the Biodegradable aliphatic-aromatic copolyester compositions described in any one of claim 2 ~ 5, its feature exists
In, described dihydroxy compounds is selected from the alkyl diol of C2 ~ C6.
Biodegradable aliphatic-aromatic copolyester compositions the most according to claim 6, it is characterised in that described two
Hydroxy compounds one in ethylene glycol, 1,3-propylene glycol, 1,4-butanediol, 1,5-pentanediol, the 1,6-HD or
Two or more mixture.
Biodegradable aliphatic-aromatic copolyester compositions the most according to claim 1, it is characterised in that described contain
The degree of randomness of alkyl/alkyloxy side chain aliphatic-aromatic copolyester is 0.8 ~ 1.2, and described degree of randomness is by 1H NMR test knot
Fruit is calculated, computational methods reference " New Chemical Materials " volume 2012,40 of test result, 12 phases, p85 ~ 87 and page 93.
Biodegradable aliphatic-aromatic copolyester compositions the most according to claim 1, it is characterised in that described contain
The intrinsic viscosity of alkyl/alkyloxy side chain aliphatic-aromatic copolyester is 1.2 ~ 1.4dL/g, and described intrinsic viscosity is with reference to GB/
T1632.5-2008 records, and test temperature is 25oC, solvent is 60 percentage by weight phenol/40 percentage by weight o-dichlorohenzenes,
The concentration of copolyesters is 0.5g/100mL, records with Ubbelohde viscometer.
Biodegradable aliphatic-aromatic copolyester compositions the most according to claim 1, it is characterised in that described contain
The melt mass flow rate of alkyl/alkyloxy side chain aliphatic-aromatic copolyester is 2 ~ 5g/10min, described melt quality
Flow rate records with reference to GB/T 3682-2000, and temperature is 190oC, load is 2.16Kg.
11. Biodegradable aliphatic-aromatic copolyester compositionss according to claim 1, it is characterised in that described contain
The fusing point of alkyl/alkyloxy side chain aliphatic-aromatic copolyester is 115oC~150oC；Described fusing point is with reference to GB/T
19466.3-2004 record.
The 12. Biodegradable aliphatic-aromatic copolyester compositionss as described in any one of claim 1 ~ 11 are at agricultural mulching
Application in industry.
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| CN102344556A (en) * | 2011-08-08 | 2012-02-08 | 北京旭阳化工技术研究院有限公司 | Biodegradable branched aromatic polyester-aliphatic polyester multi-block polymer |
| CN102492271A (en) * | 2011-12-02 | 2012-06-13 | 金发科技股份有限公司 | Full biodegradation plastic material and preparation method thereof |
| CN102516517A (en) * | 2011-12-13 | 2012-06-27 | 金发科技股份有限公司 | Method for preparing polyester-polyester blocked copolyester |
| CN102942770A (en) * | 2012-12-10 | 2013-02-27 | 中国热带农业科学院湛江实验站 | Completely-biodegradable agricultural mulching film |
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| DE19912996A1 (en) * | 1999-03-23 | 2000-09-28 | Wolff Walsrode Ag | Biodegradable agricultural films |
| KR101604113B1 (en) * | 2012-12-04 | 2016-03-16 | 주식회사 엘지화학 | Biodegradble resin composition |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102344556A (en) * | 2011-08-08 | 2012-02-08 | 北京旭阳化工技术研究院有限公司 | Biodegradable branched aromatic polyester-aliphatic polyester multi-block polymer |
| CN102492271A (en) * | 2011-12-02 | 2012-06-13 | 金发科技股份有限公司 | Full biodegradation plastic material and preparation method thereof |
| CN102516517A (en) * | 2011-12-13 | 2012-06-27 | 金发科技股份有限公司 | Method for preparing polyester-polyester blocked copolyester |
| CN102942770A (en) * | 2012-12-10 | 2013-02-27 | 中国热带农业科学院湛江实验站 | Completely-biodegradable agricultural mulching film |
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