CN116444729A - POE particle for high-performance photovoltaic adhesive film and preparation method thereof - Google Patents
POE particle for high-performance photovoltaic adhesive film and preparation method thereof Download PDFInfo
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- CN116444729A CN116444729A CN202310455110.6A CN202310455110A CN116444729A CN 116444729 A CN116444729 A CN 116444729A CN 202310455110 A CN202310455110 A CN 202310455110A CN 116444729 A CN116444729 A CN 116444729A
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- 239000002245 particle Substances 0.000 title claims abstract description 50
- 239000002313 adhesive film Substances 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000005977 Ethylene Substances 0.000 claims abstract description 25
- 239000000178 monomer Substances 0.000 claims abstract description 25
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 150000001993 dienes Chemical class 0.000 claims abstract description 11
- 239000003999 initiator Substances 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 239000004711 α-olefin Substances 0.000 claims abstract description 8
- 238000007334 copolymerization reaction Methods 0.000 claims abstract description 7
- 239000003960 organic solvent Substances 0.000 claims abstract description 6
- 239000012298 atmosphere Substances 0.000 claims abstract description 5
- 238000010559 graft polymerization reaction Methods 0.000 claims abstract description 5
- 238000003756 stirring Methods 0.000 claims description 22
- 239000003921 oil Substances 0.000 claims description 15
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 8
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 8
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 8
- NLSFWPFWEPGCJJ-UHFFFAOYSA-N 2-methylprop-2-enoyloxysilicon Chemical compound CC(=C)C(=O)O[Si] NLSFWPFWEPGCJJ-UHFFFAOYSA-N 0.000 claims description 7
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 6
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 6
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 6
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 6
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 238000012360 testing method Methods 0.000 claims description 6
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 claims description 5
- FIYMNUNPPYABMU-UHFFFAOYSA-N 2-benzyl-5-chloro-1h-indole Chemical compound C=1C2=CC(Cl)=CC=C2NC=1CC1=CC=CC=C1 FIYMNUNPPYABMU-UHFFFAOYSA-N 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 238000004806 packaging method and process Methods 0.000 claims description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 4
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 claims description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 claims description 4
- 229920000578 graft copolymer Polymers 0.000 claims description 4
- 239000012535 impurity Substances 0.000 claims description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 4
- 239000013557 residual solvent Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 claims description 3
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 3
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 claims description 3
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 claims description 3
- 238000011049 filling Methods 0.000 claims description 3
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 claims description 2
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 claims description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 claims description 2
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 claims description 2
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000010724 circulating oil Substances 0.000 claims description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 2
- 239000007822 coupling agent Substances 0.000 claims description 2
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 claims description 2
- MABAWBWRUSBLKQ-UHFFFAOYSA-N ethenyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)C=C MABAWBWRUSBLKQ-UHFFFAOYSA-N 0.000 claims description 2
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 claims description 2
- 238000011010 flushing procedure Methods 0.000 claims description 2
- 238000009775 high-speed stirring Methods 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 238000005086 pumping Methods 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 125000004810 2-methylpropylene group Chemical group [H]C([H])([H])C([H])(C([H])([H])[*:2])C([H])([H])[*:1] 0.000 claims 1
- 229920000098 polyolefin Polymers 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000012752 auxiliary agent Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000001125 extrusion Methods 0.000 description 5
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052726 zirconium Inorganic materials 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000003490 calendering Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 239000005038 ethylene vinyl acetate Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 2
- 229920006124 polyolefin elastomer Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 239000013538 functional additive Substances 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012968 metallocene catalyst Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
- C08F255/02—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/16—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J151/06—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/10—Adhesives in the form of films or foils without carriers
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/04—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof adapted as photovoltaic [PV] conversion devices
- H01L31/042—PV modules or arrays of single PV cells
- H01L31/048—Encapsulation of modules
- H01L31/0481—Encapsulation of modules characterised by the composition of the encapsulation material
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Electromagnetism (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Graft Or Block Polymers (AREA)
Abstract
The invention relates to the technical field of polyolefin preparation, in particular to POE particles for a high-performance photovoltaic adhesive film and a preparation method thereof. Under anhydrous inert atmosphere, ethylene is dissolved in an organic solvent in a batch reactor, alpha-olefin, conjugated diene, a copolymerization catalyst and a cocatalyst are sequentially added, and the functionalized POE with double bonds in the main chain is obtained through polymerization. And then releasing ethylene pressure, removing redundant solvent in vacuum, and introducing a second solvent, an initiator, a grafting monomer, a co-grafting monomer and the like into the same reactor to perform graft polymerization reaction, so as to prepare POE particles for the high-performance photovoltaic adhesive film. The distribution uniformity of the grafted side chains can be effectively improved, and the problems of gel generation, monomer and initiator residues caused by grafting reaction are avoided.
Description
Technical Field
The invention relates to POE particles, in particular to POE particles for a high-performance photovoltaic adhesive film and a preparation method thereof.
Background
Polyolefin elastomer Polyolefin elastomer, POE for short, is one of the main raw materials of the current photovoltaic packaging adhesive film. Compared with EVA (ethylene-vinyl acetate copolymer), POE has the remarkable characteristics of low density, high water vapor barrier property, aging resistance, low temperature resistance, excellent insulating property and the like. At present, POE photovoltaic packaging adhesive films account for about 20% of market share, and the market occupation rate is rising year by year. However, the nonpolar POE particles have obvious disadvantages, such as slow absorption of small molecule functional additives, weak adhesion to the matrix, and slipping of the adhesive film due to easy precipitation of the additives.
The polar monomer, such as POE grafted polymer, is introduced into the POE molecular chain, and the defects can be remarkably improved by improving the polarity of POE, for example, CN108753184A discloses a silane grafted POE adhesive film for photovoltaic encapsulation and a preparation method. POE grafted maleic anhydride or POE grafted glycidyl methacrylate is introduced into the system, so that the compatibility of resin and polar small molecule auxiliary agents can be promoted in the processing process of the adhesive film, the absorption rate of POE resin to the auxiliary agents can be improved, the auxiliary agents in the adhesive film are prevented from being separated out, and the adhesive force of the adhesive film and a substrate is improved.
At present, POE grafted polymer for photovoltaic packaging adhesive films is produced by adopting a reaction extrusion process, namely POE particles, an initiator, a grafting monomer and the like are introduced into a double-screw extruder, grafting reaction is carried out under the POE molten state, and a polar monomer is introduced into a POE molecular chain. This method has the significant disadvantage of low grafting (silicone monomer grafting < 5%), uneven distribution of grafted side chains, and large amounts of residual initiator and grafted monomer.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides POE particles for the high-performance photovoltaic adhesive film, which have the advantages of rapid absorption auxiliary agent, strong adhesive force and auxiliary agent precipitation prevention.
In order to achieve the above purpose, the invention is realized by the following technical scheme:
POE particles for high-performance photovoltaic adhesive films and a preparation method thereof are carried out according to the following steps:
before polymerization, the batch reaction kettle is carried out in an environment with the temperature of 95 ℃, the batch reaction kettle is vacuumized in a circulating oil bath, and then the batch reaction kettle is baked for 2 hours to remove residual impurities in the kettle;
then the temperature of the oil bath is stabilized to the reaction temperature of 30-200 ℃ and N 2 Connecting a pipeline under the atmosphere, replacing the system with ethylene for 3 times, and filling ethylene until the pressure in the reactor reaches 0.1MPa;
stirring is started, under the ethylene atmosphere, an organic solvent accounting for 30% -90% of the volume of the reactor is added to enable ethylene to be fully dissolved in the reactor, and then a cocatalyst with the concentration not lower than 25 mu mL/L is added to stir for 1-10 min so as to fully remove residual impurities in the system;
then adding alpha-olefin, conjugated diene, a copolymerization catalyst and 0.01-1 mol/L hydrogen in sequence, continuously stirring at the temperature of 30-200 ℃ to carry out polymerization reaction for 0.1-10 h, and obtaining a functional POE solid with a main chain containing double bonds after polymerization;
releasing ethylene pressure to 0.1Mpa for 1-3 min in an intermittent reactor for obtaining functionalized POE solid, rapidly stirring residual solvent in the intermittent reactor at a speed of 100-500 r/min, and slowly vacuumizing by a rotary-vane vacuum pump after stirring, so as to fully remove unreacted monomers and solvent;
then flushing N in the same reactor 2 Until the pressure of the reactor reaches 0.1MPa, filling a second solvent accounting for 10-50% of the volume of the reactor, sequentially introducing an initiator, a grafting monomer and a co-grafting monomer, simultaneously adjusting an oil bath to a target reaction temperature (40-130 ℃), and carrying out graft polymerization under high-speed stirring at a stirring rate of 200-800 r/min;
after the reaction is finished, opening a pressure release valve, and releasing the pressure of the system to 0.1MPa; and then conveying the materials to a double-screw granulating line through a screw pump and a pipeline, and removing residual solvents in the materials under the vacuum pumping operation at the granulating temperature of 50-150 ℃ and the rotating speed of 50-500 r/min to prepare POE particles for the high-performance photovoltaic adhesive film with the particle size of 1-5 mm.
Preferably, the concentration of the copolymerization catalyst is 0.5-200 mu mL/L, the molar ratio of the cocatalyst to the copolymerization catalyst is 50-5000:1, the concentration of the ethylene and the alpha-olefin is 0.02-10 mol/L, and the concentration of the conjugated diene is 0.02-10 mol/L; the mass of the initiator is 0.5-10 g, the mass of the grafting monomer is 5-50 g, the mass of the co-grafting monomer is 5-50 g, the temperature of the grafting polymerization reaction is 40-130 ℃, and the reaction time is 0.1-5 h.
Preferably, the alpha-olefin is one or more of propylene, 1-butene, 1-hexene, 1-octene, 1-decene, isopentene and 2-methylpropene.
Preferably, the conjugated diene is one or more of butadiene, isoprene, cyclopentadiene, 1, 3-cyclohexadiene, 2, 4-hexadiene and 1, 3-cyclooctadiene.
Preferably, the initiator in the graft polymerization reaction is one or more of azodiisobutyronitrile, dibenzoyl peroxide, di-tert-butylperoxyisopropyl benzene, dicumyl peroxide, tert-butyl peroxy-2-ethylhexyl carbonate, 2, 5-dimethyl-2, 5-bis (tert-butylperoxy) hexane and tert-butyl peroxy-2-ethylhexyl carbonate.
Preferably, the grafting monomer is one or more of oligomer coupling agent, gamma-methacryloxypropyl trimethoxy silane, methacryloxysilane, vinyl trimethoxy silane, vinyl tri (beta-methoxyethoxy) silane, vinyl triethoxysilane and vinyl triisopropoxysilane.
Preferably, the co-grafting monomer is one or more of 1,3, 5-triallyl cyanurate, triallyl isocyanurate, trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, styrene and divinylbenzene.
Preferably, the POE particles thus produced have a density of 0.855 to 0.915g/cm 3 The method comprises the steps of carrying out a first treatment on the surface of the Under the test condition of 190 ℃/2.16kg, the melt index of the POE particles is 0.1-40 g/10 mm, the molecular weight distribution of the POE particles is 1.5-4.0, and the residual amount of the organic solvent is 50-1000 ppm based on the total mass of the POE grafted polymer.
Preferably, the grafting ratio of POE particles is 1% to 20% based on the total mass of POE particles.
Preferably, the POE particles have a double bond content of 0.01 to 0.2% based on the molar amount of conjugated diene.
And (3) application of POE particles, wherein the POE particles are used for preparing a photovoltaic packaging adhesive film.
The technical scheme of the invention has the beneficial effects that:
the absorption time of the auxiliary agent of the POE particles for the high-performance photovoltaic adhesive film prepared by the invention is less than 60min, the dynamic friction coefficient is more than 0.7, and the peeling strength with glass is more than 80N/cm. Can effectively solve the problems of slow absorption of nonpolar POE to small molecule functional auxiliary agent, weak adhesion with matrix, easy precipitation of auxiliary agent, etc.
The POE particles for the high-performance photovoltaic adhesive film prepared by the method realize high-performance modification of the POE particles in a polymerization stage, are more efficient than the traditional POE particles subjected to secondary reaction extrusion grafting, and can be directly processed and used.
The system introduces conjugated diene monomer in POE polymerization stage, can introduce double bond in POE main chain, and can raise grafting rate greatly.
According to the system, POE is subjected to grafting reaction through solution grafting polymerization, so that the distribution uniformity of grafted side chains can be effectively improved, and the problems of gel generation, monomer and initiator residues caused by grafting reaction are avoided.
Detailed Description
The technical solutions of the embodiments of the present invention will be clearly and completely described below in conjunction with the embodiments of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments.
The molar feed concentration to be used in the present invention refers to the initial concentration of ethylene, alpha-olefin of 4 to 12 carbon atoms or conjugated diene monomer, by volume of organic solvent, as it enters the reactor.
In the invention, the molar content of double bonds in POE and the grafting rate are used 1 H and 13 c Nuclear magnetic resonance spectrometer (NMR Bruker AC 400) at 120deg.C with deuterated reagent of 1,2-C 6 D 4 Cl 2 。
The film of the test sample of the POE prepared by the invention is calendered to form a film at 145 ℃ through a hot press, and the thickness of the film is 0.3mm.
According to the invention, the absorption performance of the auxiliary agent of the prepared POE particles is evaluated, the POE particles and the auxiliary agent are uniformly mixed, and then the mixture is placed in an environment of 50 ℃ until the auxiliary agent is completely absorbed, and the time is recorded.
According to the invention, the dynamic friction coefficient of the POE particles is measured, a pressed sample film is taken, 6 samples with the same size are cut, and the measurement is carried out on a base film with the length of more than 40cm by using a COF-2002 type friction coefficient meter.
According to the invention, the peel strength of the POE particles is measured, the pressed sample films are stacked into a back plate/sample film/glass form, and the film is calendered into a film at 150 ℃ through a hot press and then is carried out on a universal material tester.
Example 1: the 2L reactor was opened to raise the temperature of the oil bath to 60℃and connected to a reactor tube by a vacuum pump to remove water and oxygen, after 2 hours, 900mL of a toluene solution of 0.3mol/L butadiene was added, the stirring speed was set to 300rpm, 100mL of 1-hexene, 10mL of a toluene solution of 2mol/L methylaluminoxane, and 5mg of a zirconium catalyst were added to the reactor.
Ethylene was introduced into the reactor until the pressure was stabilized at 0.4MPa, after polymerization for 60 minutes, the ethylene pressure was released and the solvent was removed by vacuum, and 750ml of xylene, 25ml of methacryloxysilane, 5g of dibenzoyl peroxide, 25ml of 1,3, 5-triallyl cyanurate were added to the same reactor.
The stirring speed was set at 500rpm, the oil bath temperature was raised to 100℃and after 1.5 hours of reaction, the discharge valve was opened, the resulting product was washed several times with a large amount of acidified ethanol having a volume ratio of ethanol/hydrochloric acid of 95/5, filtered and dried under suction, and vacuum dried at 60℃for 8 hours. The double bond content in the product was 1.2mol% and the grafting rate was 12.3mol%.
Example 2: the 2L reactor was opened to raise the temperature of the oil bath to 60℃and connected to a reactor tube by a vacuum pump to remove water and oxygen, after 2 hours, 900mL of a xylene solution of 0.3mol/L isoprene was added, the stirring speed was set to 300rpm, 100mL of 1-butene, 10mL of a xylene solution of 2mol/L methylaluminoxane, and 5mg of a zirconium catalyst were added to the reactor.
Ethylene was introduced into the autoclave until the pressure was stabilized at 0.4MPa. After 60min of polymerization, the ethylene pressure was released and the solvent was removed by vacuum, 750ml of xylene, 25ml of methacryloxysilane, 5g of dibenzoyl peroxide, 25ml of 1,3, 5-triallyl isocyanurate were added to the same reactor. The stirring speed was set at 500rpm, the oil bath temperature was raised to 100℃and after 1.5 hours of reaction, the discharge valve was opened, the resulting product was washed several times with a large amount of acidified ethanol having a volume ratio of ethanol/hydrochloric acid of 95/5, filtered and dried under suction, and vacuum dried at 60℃for 8 hours.
The double bond content in the product was 0.6mol% and the grafting ratio was 10.4mol%.
Example 3: the 2L reactor was opened to conduct an oil bath, the temperature of the oil bath was raised to 60℃and a vacuum pump was connected to the reactor tube to remove water oxygen, after 2 hours, 900mL of a 0.3mol/L n-decane solution of 2, 4-hexadiene was added, the stirring speed was set at 300rpm, 100mL of 1-octene, 10mL of a 2mol/L n-decane solution of methylaluminoxane and 5mg of a zirconium metallocene catalyst were added to the reactor.
Ethylene was introduced into the autoclave until the pressure was stabilized at 0.4MPa. After polymerization for 60min, the ethylene pressure was released and the solvent was removed by vacuum, 600ml xylene, 150ml ethyl acetate, 25ml methacryloxysilane, 5g dibenzoyl peroxide, 25ml 1,3, 5-triallyl isocyanurate were added to the same reactor. The stirring speed was set at 500rpm, the oil bath temperature was raised to 100℃and after 1.5 hours of reaction, the discharge valve was opened, the resulting product was washed several times with a large amount of acidified ethanol having a volume ratio of ethanol/hydrochloric acid of 95/5, filtered and dried under suction, and vacuum dried at 60℃for 8 hours. The double bond content in the product was 0.4mol% and the grafting ratio was 9.5mol%.
Example 4: the 2L reactor was opened to raise the temperature of the oil bath to 60℃and connected to a reactor tube by a vacuum pump to remove water and oxygen, after 2 hours, 900mL of a 0.3mol/L n-decane solution of cyclopentadiene was added, the stirring speed was set to 300rpm, 100mL of 1-octene, 10mL of a 2mol/L n-decane solution of methylaluminoxane and 5mg of a zirconium-rich catalyst were added to the reactor.
Ethylene was introduced into the autoclave until the pressure was stabilized at 0.4MPa. After 30min of polymerization, the ethylene pressure was released and the solvent was removed by vacuum, 600ml of xylene, 150ml of methyl butanone, 25ml of methacryloxysilane, 5g of dibenzoyl peroxide, 25ml of triallyl isocyanurate were added to the same reactor. The stirring speed was set at 500rpm, the oil bath temperature was raised to 100℃and after 1.5 hours of reaction, the discharge valve was opened, the resulting product was washed several times with a large amount of acidified ethanol having a volume ratio of ethanol/hydrochloric acid of 95/5, filtered and dried under suction, and vacuum dried at 60℃for 8 hours.
The double bond content in the product was 0.7mol% and the grafting ratio was 8.7mol%.
Example 5: the 2L reactor was opened to raise the temperature of the oil bath to 60℃and connected to a reactor tube by a vacuum pump to remove water and oxygen, after 2 hours, 900mL of a toluene solution of 0.3mol/L butadiene was added, the stirring speed was set to 300rpm, 100mL of 1-hexene, 10mL of a toluene solution of 2mol/L methylaluminoxane, and 5mg of a zirconium catalyst were added to the reactor.
Ethylene was introduced into the autoclave until the pressure was stabilized at 0.4MPa. After polymerization for 30min, the ethylene pressure was released and the solvent was removed by vacuum, 550ml of xylene, 200ml of ethyl acetate, 25ml of methacryloxysilane, 5g of di-t-butylperoxyisopropyl benzene, 25ml of trimethylolpropane triacrylate were added to the same reactor. The stirring speed was set at 500rpm, the oil bath temperature was raised to 100℃and after 1.5 hours of reaction, the discharge valve was opened, the resulting product was washed several times with a large amount of acidified ethanol having a volume ratio of ethanol/hydrochloric acid of 95/5, filtered and dried under suction, and vacuum dried at 60℃for 8 hours. The double bond content in the product was 1.1mol% and the grafting ratio was 13.1mol%.
Comparative example 1:
the comparative example is a sample of POE particles (not modified by grafting) for photovoltaic adhesive films of the first three on the market.
Comparative example 2:
the comparative example is prepared by grafting POE particles for photovoltaic adhesive films on the market through a double screw extruder. 100 parts of POE, 2 parts of silane coupling agent vinyl trimethoxy silane, 0.1 part of tert-butyl peroxy-2-ethylhexyl carbonate and 4 parts of trimethylolpropane trimethacrylate. And (3) uniformly mixing various resins, putting the mixture into a double-screw extrusion granulator, heating and melting the mixture at 180 ℃ for extrusion, and cutting the mixture into granules, wherein the rotating speed of a screw in the double-screw extrusion granulator is 500r/min.
Test example 1:
examples 1 to 5 and comparative examples 1 to 2 were calendered to form films at 145℃by means of a hot press, the film thickness being 0.3mm. The sample films were then subjected to performance testing, the test structures being shown in table 1.
TABLE 1 copolymer film Performance test Table
With the above-described preferred embodiments according to the present invention as an illustration, the above-described descriptions can be used by persons skilled in the relevant art to make various changes and modifications without departing from the scope of the technical idea of the present invention. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention. The technical scope of the present invention is not limited to the description, but must be determined according to the scope of claims.
Claims (11)
1. The POE particles for the high-performance photovoltaic adhesive film and the preparation method thereof are characterized by comprising the following steps:
before polymerization, the batch reaction kettle is carried out in an environment with the temperature of 95 ℃, the batch reaction kettle is vacuumized in a circulating oil bath, and then the batch reaction kettle is baked for 2 hours to remove residual impurities in the kettle;
then the temperature of the oil bath is stabilized to the reaction temperature of 30-200 ℃ and N 2 Connecting a pipeline under the atmosphere, replacing the system with ethylene for 3 times, and filling ethylene until the pressure in the reactor reaches 0.1MPa;
stirring is started, under the ethylene atmosphere, an organic solvent accounting for 30% -90% of the volume of the reactor is added to enable ethylene to be fully dissolved in the reactor, and then a cocatalyst with the concentration not lower than 25 mu mL/L is added to stir for 1-10 min so as to fully remove residual impurities in the system;
then adding alpha-olefin, conjugated diene, a copolymerization catalyst and 0.01-1 mol/L hydrogen in sequence, continuously stirring at the temperature of 30-200 ℃ to carry out polymerization reaction for 0.1-10 h, and obtaining a functional POE solid with a main chain containing double bonds after polymerization;
releasing ethylene pressure to 0.1Mpa for 1-3 min in an intermittent reactor for obtaining functionalized POE solid, rapidly stirring residual solvent in the intermittent reactor at a speed of 100-500 r/min, and slowly vacuumizing by a rotary-vane vacuum pump after stirring, so as to fully remove unreacted monomers and solvent;
then flushing N in the same reactor 2 Until the pressure of the reactor reaches 0.1MPa, andfilling a second solvent accounting for 10-50% of the volume of the reactor, sequentially introducing an initiator, a grafting monomer and a co-grafting monomer, simultaneously adjusting an oil bath to a target reaction temperature (40-130 ℃), and carrying out graft polymerization under high-speed stirring at a stirring rate of 200-800 r/min;
after the reaction is finished, opening a pressure release valve, and releasing the pressure of the system to 0.1MPa; and then conveying the materials to a double-screw granulating line through a screw pump and a pipeline, and removing residual solvents in the materials under the vacuum pumping operation at the granulating temperature of 50-150 ℃ and the rotating speed of 50-500 r/min to prepare POE particles for the high-performance photovoltaic adhesive film with the particle size of 1-5 mm.
2. The POE particles for high performance photovoltaic film according to claim 1 and the preparation method thereof, wherein: the concentration of the copolymerization catalyst is 0.5-200 mu mL/L, the molar ratio of the cocatalyst to the copolymerization catalyst is 50-5000:1, the concentrations of ethylene and alpha-olefin are 0.02-10 mol/L, and the concentration of conjugated diene is 0.02-10 mol/L; the mass of the initiator is 0.5-10 g, the mass of the grafting monomer is 5-50 g, the mass of the co-grafting monomer is 5-50 g, the temperature of the grafting polymerization reaction is 40-130 ℃, and the reaction time is 0.1-5 h.
3. The POE particles for high performance photovoltaic film according to claim 1 and the preparation method thereof, wherein: the alpha-olefin is one or more of propylene, 1-butene, 1-hexene, 1-octene, 1-decene, isopentene and 2-methyl propylene.
4. The POE particles for high performance photovoltaic film according to claim 1 and the preparation method thereof, wherein: the conjugated diene is one or more of butadiene, isoprene, cyclopentadiene, 1, 3-cyclohexadiene, 2, 4-hexadiene and 1, 3-cyclooctadiene.
5. The POE particles for high performance photovoltaic film according to claim 1 and the preparation method thereof, wherein: the initiator in the graft polymerization reaction is one or more of azodiisobutyronitrile, dibenzoyl peroxide, di-tert-butylperoxyisopropyl benzene, dicumyl peroxide, tert-butyl peroxy-2-ethylhexyl carbonate, 2, 5-dimethyl-2, 5-bis (tert-butylperoxy) hexane and tert-butyl peroxy-2-ethylhexyl carbonate.
6. The POE particles for high performance photovoltaic film according to claim 1 and the preparation method thereof, wherein: the grafting monomer is one or more of oligomer coupling agent, gamma-methacryloxypropyl trimethoxy silane, methacryloxy silane, vinyl trimethoxy silane, vinyl tri (beta-methoxyethoxy) silane, vinyl triethoxy silane and vinyl triisopropoxy silane.
7. The POE particles for high performance photovoltaic film according to claim 1 and the preparation method thereof, wherein: the co-grafting monomer is one or more of 1,3, 5-triallyl cyanurate, triallyl isocyanurate, trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, styrene and divinylbenzene.
8. The POE particles for high performance photovoltaic film according to claim 1 and the preparation method thereof, wherein: the density of the POE particles is 0.855-0.915 g/cm 3 The method comprises the steps of carrying out a first treatment on the surface of the Under the test condition of 190 ℃/2.16kg, the melt index of the POE particles is 0.1-40 g/10 mm, the molecular weight distribution of the POE particles is 1.5-4.0, and the residual amount of the organic solvent is 50-1000 ppm based on the total mass of the POE grafted polymer.
9. The POE particles for high performance photovoltaic film according to claim 1 and the preparation method thereof, wherein: the grafting rate of the POE particles is 1-20% based on the total mass of the POE particles.
10. The POE particles for high performance photovoltaic film according to claim 1 and the preparation method thereof, wherein: calculated by the molar quantity of conjugated diene, the double bond content of POE particles is 0.01-0.2%.
11. Use of POE particles for high performance photovoltaic adhesive films as defined in any one of claims 1 to 10, characterized in that: and the POE particles are used for preparing photovoltaic packaging adhesive films.
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| US3953541A (en) * | 1973-07-20 | 1976-04-27 | Mitsui Petrochemical Industries Ltd. | Process for preparation of polyolefin graft copolymers |
| CN101367896A (en) * | 2007-08-14 | 2009-02-18 | 中国科学院化学研究所 | Unsaturated polyolefin copolymer and method of preparing the same |
| CN103289582A (en) * | 2013-05-21 | 2013-09-11 | 上海海优威电子技术有限公司 | Packaging adhesive film for cross-linked POE (polyolefin elastomer) solar photovoltaic module |
| CN108753184A (en) * | 2018-06-21 | 2018-11-06 | 常州斯威克光伏新材料有限公司 | A kind of photovoltaic encapsulation Silane Grafted POE glued membranes and preparation method |
| CN111334202A (en) * | 2020-03-02 | 2020-06-26 | 上海海优威新材料股份有限公司 | Hot melt adhesive film |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3953541A (en) * | 1973-07-20 | 1976-04-27 | Mitsui Petrochemical Industries Ltd. | Process for preparation of polyolefin graft copolymers |
| CN101367896A (en) * | 2007-08-14 | 2009-02-18 | 中国科学院化学研究所 | Unsaturated polyolefin copolymer and method of preparing the same |
| CN103289582A (en) * | 2013-05-21 | 2013-09-11 | 上海海优威电子技术有限公司 | Packaging adhesive film for cross-linked POE (polyolefin elastomer) solar photovoltaic module |
| CN108753184A (en) * | 2018-06-21 | 2018-11-06 | 常州斯威克光伏新材料有限公司 | A kind of photovoltaic encapsulation Silane Grafted POE glued membranes and preparation method |
| CN111334202A (en) * | 2020-03-02 | 2020-06-26 | 上海海优威新材料股份有限公司 | Hot melt adhesive film |
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