CN117720732A - Preparation method of phenolic hydroxyl-terminated modified polysiloxane and toughening application of phenolic hydroxyl-terminated modified polysiloxane in epoxy plastic packaging material - Google Patents
Preparation method of phenolic hydroxyl-terminated modified polysiloxane and toughening application of phenolic hydroxyl-terminated modified polysiloxane in epoxy plastic packaging material Download PDFInfo
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- CN117720732A CN117720732A CN202311777284.0A CN202311777284A CN117720732A CN 117720732 A CN117720732 A CN 117720732A CN 202311777284 A CN202311777284 A CN 202311777284A CN 117720732 A CN117720732 A CN 117720732A
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- phenolic hydroxyl
- modified polysiloxane
- toughening
- terminated modified
- polysiloxane
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- -1 polysiloxane Polymers 0.000 title claims abstract description 49
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 44
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 239000004593 Epoxy Substances 0.000 title claims abstract description 19
- 239000004033 plastic Substances 0.000 title claims abstract description 15
- 239000005022 packaging material Substances 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 239000003822 epoxy resin Substances 0.000 claims abstract description 17
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 17
- 239000000463 material Substances 0.000 claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 12
- 238000002156 mixing Methods 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
- 229920006336 epoxy molding compound Polymers 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 10
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 229920001568 phenolic resin Polymers 0.000 claims description 9
- 239000005011 phenolic resin Substances 0.000 claims description 9
- 238000003786 synthesis reaction Methods 0.000 claims description 9
- 239000012745 toughening agent Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000012263 liquid product Substances 0.000 claims description 8
- 239000012752 auxiliary agent Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- NELGPGQMQVOTKH-UHFFFAOYSA-N 2-methoxy-4-prop-2-enylphenol Chemical compound COC1=CC(CC=C)=CC=C1O.COC1=CC(CC=C)=CC=C1O NELGPGQMQVOTKH-UHFFFAOYSA-N 0.000 claims description 3
- PWRCOONECNWDBH-UHFFFAOYSA-N 4-prop-2-enoxyphenol Chemical compound OC1=CC=C(OCC=C)C=C1 PWRCOONECNWDBH-UHFFFAOYSA-N 0.000 claims description 3
- 238000004898 kneading Methods 0.000 claims description 2
- 238000011049 filling Methods 0.000 claims 1
- 238000004806 packaging method and process Methods 0.000 abstract description 6
- 230000002194 synthesizing effect Effects 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 13
- 230000000694 effects Effects 0.000 description 6
- 239000004065 semiconductor Substances 0.000 description 6
- 238000009472 formulation Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 229910021488 crystalline silicon dioxide Inorganic materials 0.000 description 3
- 238000007599 discharging Methods 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 238000011056 performance test Methods 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 239000004848 polyfunctional curative Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 230000001603 reducing effect Effects 0.000 description 2
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 1
- 241001391944 Commicarpus scandens Species 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
Landscapes
- Epoxy Resins (AREA)
- Silicon Polymers (AREA)
Abstract
The invention discloses a phenolic hydroxyl-terminated modified polysiloxane and a preparation method thereof, and the application of the phenolic hydroxyl-terminated modified polysiloxane in epoxy plastic packaging materials is studied. The invention prepares the low-modulus epoxy plastic package material by autonomously synthesizing the polysiloxane modified by the terminal phenolic hydroxyl, and then mixing the polysiloxane serving as a toughening aid with epoxy resin, a curing agent, a catalyst and other functional aids. The prepared phenolic hydroxyl-terminated modified polysiloxane is used for toughening the epoxy plastic packaging material, provides an effective method for the low-stress technology of the epoxy plastic packaging material, and has good application prospect in the aspect of improving the reliability of plastic packaging devices.
Description
Technical Field
The invention belongs to the field of semiconductor packaging materials, and particularly relates to preparation of phenolic hydroxyl-terminated modified polysiloxane and toughening application of the phenolic hydroxyl-terminated modified polysiloxane in an epoxy plastic packaging material.
Background
The epoxy resin has good mechanical strength, bonding property, heat resistance, electrical property and molding processability, and meanwhile, the synthetic cost is low, so that the epoxy resin becomes one of the main materials of the epoxy plastic packaging material for the current semiconductor packaging. However, the epoxy plastic packaging material has the defects of higher internal stress, high crosslinking density after the epoxy resin is cured, high brittleness, poor toughness and the like, and the application of the epoxy plastic packaging material is limited to a certain extent.
In recent years, semiconductors are being developed towards high integration, chips are larger, wires are finer, devices are lighter, thinner and miniaturized, and comprehensive performance and reliability of the EMC materials are also required to be higher, wherein stress is an important factor affecting the packaging reliability of the EMC materials. On one hand, the internal stress is too large, so that the bonding wires are easy to break, and the bonding wires are easy to be detached from the chip metal wiring; for large scale integrated circuits, excessive internal stress can also lead to misalignment of metal wiring and silicon chip cracking; in addition, excessive internal stress may cause cracking of the chip passivation film, and in severe cases may even crack EMC and delaminate from the frame.
The side group epoxy modified polysiloxane is widely applied to EMC materials for semiconductor packaging as a common stress modification auxiliary agent, but the stress reduction effect is limited, and the possible reasons are as follows: (a) The specificity of the EMC formula, the molar ratio of epoxy groups of the epoxy resin to hydroxyl groups in the phenolic curing agent is generally greater than 1, so that the probability of participation of the epoxy modified polysiloxane with side groups in the reaction is reduced; (b) Even if the epoxy groups on the pendant polysiloxane groups participate in the reaction, they may only ultimately hang on the resulting crosslinked network structure due to steric reasons, both of which greatly impair the stress reducing effect of the pendant epoxy-modified polysiloxane. In the current trend of high reliability requirements for packaging devices, the side group epoxy modified polysiloxane cannot meet the requirements in many application scenes. The design and preparation of the novel functional toughening additive with excellent performance and capability of reducing the stress (modulus) of the EMC material to a greater extent is a difficult problem before the design and preparation of the novel functional toughening additive, and has great challenges.
Disclosure of Invention
The invention aims to provide the polysiloxane modified by the terminal phenolic hydroxyl groups, which is modified by the terminal phenolic hydroxyl groups with higher reactivity, so that the modified new material has better toughening effect in EMC, and the application range of the EMC material for semiconductor packaging is widened.
The technical scheme of the invention is as follows:
a terminal phenolic hydroxyl modified polysiloxane has a chemical structural formula selected from one of I and II:
wherein n represents the number of repeating units and the value range is an integer between 0 and 50.
It is another object of the present invention to provide a process for preparing a terminal phenolic hydroxyl group-modified polysiloxane of the above two structural formulas, comprising the following steps.
The synthesis of structural formula I comprises the following synthesis steps:
polysiloxane containing terminal hydrogen and chloroplatinic acid (H) 2 PtCl·6H 2 O) and a trace amount of polymerization inhibitor p-hydroxyanisole (MEHQ) are added into a 500ml three-necked round bottom flask containing tetrahydrofuran, the three-necked round bottom flask is provided with a stirrer, a dropping funnel and a reflux condensing device, and the substances are heated under stirring; 2-methoxy-4- (2-propenyl) phenol (eugenol) was dissolved in tetrahydrofuran and added dropwise through a dropping funnel; after the reaction, volatile matters were removed under reduced pressure to obtain a pale yellow liquid product.
The synthesis of structural formula II comprises the following synthesis steps:
polysiloxane containing terminal hydrogen and chloroplatinic acid (H) 2 PtCl·6H 2 O) and a trace amount of polymerization inhibitor p-hydroxyanisole (MEHQ) are added into a 500ml three-necked round bottom flask containing tetrahydrofuran, the three-necked round bottom flask is provided with a stirrer, a dropping funnel and a reflux condensing device, and the substances are heated under stirring; dissolving 4-allyloxyphenol in tetrahydrofuran and adding dropwise through a dropping funnel; after the reaction, volatile matters were removed under reduced pressure to obtain a pale yellow liquid product.
The invention further aims to provide toughening application of the phenolic hydroxyl-terminated modified polysiloxane in an epoxy plastic package material, and the technical aim is achieved through the following technical scheme.
The terminal phenolic hydroxyl modified polysiloxane is used as a toughening aid, is mixed with epoxy resin, a phenolic resin curing agent, a catalyst and other functional aids, and then an epoxy plastic package (EMC) is prepared, so that the toughening effect of the terminal phenolic hydroxyl polysiloxane on the EMC material is researched.
Preferably, the epoxy resin is selected from any one or a combination of the following structures:
preferably, the phenolic resin curing agent is selected from any one or a combination of the following structures:
preferably, the structure of the catalyst is selected from any one or more of imidazole and derivatives thereof, organic amine compounds, triphenylphosphine and derivatives thereof, and phosphonium salt compounds.
Preferably, the composition of the formulation is as follows:
preferably, the specific production steps of the preparation comprise the following production steps:
(a) Uniformly mixing epoxy resin, phenolic resin curing agent, catalyst, toughening agent and other functional auxiliary agents by a high-speed stirrer to obtain a premix;
(b) And further kneading and mixing the premix by a double screw extruder, and cooling and crushing the extrudate to prepare the EMC material.
Detailed Description
In order to gain an improved understanding of the nature and meaning of the present invention, it will be further explained in connection with specific embodiments and it is necessary to point out here that: the following examples are given for the purpose of illustration only and are not to be construed as limiting the scope of the invention, since numerous insubstantial modifications and adaptations of the invention to those skilled in the art in light of the present disclosure or to methods are within the scope of the invention.
Example 1:
(1) Synthesis of structural formula i:
400g of polysiloxane having a hydrogen content of 0.17% and chloroplatinic acid (H) 2 PtCl·6H 2 O;15 ppm) and 2 drops of polymerization inhibitor para-hydroxyanisole (MEHQ) were added to a 500ml three-necked round bottom flask containing tetrahydrofuran, the three-necked round bottom flask being equipped with a stirrer, a dropping funnel and a reflux condenser, the above substances being heated to 60℃under stirring; 112g of 2-methoxy-4- (2-propenyl) phenol (eugenol) was dissolved in tetrahydrofuran and added dropwise through a dropping funnel; after 8h of reaction, volatile substances are removed under reduced pressure to obtain a pale yellow liquid product, and the molecular formula of the pale yellow liquid product is as follows:
(2) Preparation of Epoxy Molding Compound (EMC)
According to the following table formulation, crystalline SiO 2 The filler, EOCN epoxy resin, OCN phenolic resin curing agent, triphenylphosphine catalyst, toughening agent (structural formula I) and other functional auxiliary agents are uniformly mixed by a high-speed stirrer, the mixture is kneaded and mixed by a double-screw extruder, the discharging temperature is controlled to be not higher than 118 ℃, the mixture is cooled by a calender and a cooling belt after being discharged, and then the mixture is crushed by a crusher to obtain a powdery sample 1, and the sample 1 is subjected to performance test analysis.
Example 2:
(1) Synthesizing a structural formula II:
hydrogen content was set to 0.17%400g of polysiloxane, chloroplatinic acid (H) 2 PtCl·6H 2 O;15 ppm) and 2 drops of polymerization inhibitor para-hydroxyanisole (MEHQ) were added to a 500ml three-necked round bottom flask containing tetrahydrofuran, the three-necked round bottom flask being equipped with a stirrer, a dropping funnel and a reflux condenser, the above substances being heated to 60℃under stirring; 103g of 4-allyloxyphenol was dissolved in tetrahydrofuran and added dropwise via a dropping funnel; after 8h of reaction, volatile substances are removed under reduced pressure to obtain a pale yellow liquid product, and the molecular formula of the pale yellow liquid product is as follows:
(2) Preparation of Epoxy Molding Compound (EMC)
According to the following table formulation, crystalline SiO 2 The filler, EOCN epoxy resin, OCN phenolic resin curing agent, triphenylphosphine catalyst, toughening agent (structural formula II) and other functional auxiliary agents are uniformly mixed by a high-speed stirrer, the mixture is further kneaded and mixed by a double-screw extruder, the discharging temperature is controlled to be not higher than 118 ℃, the mixture is cooled by a calender and a cooling belt after being discharged, and then the mixture is crushed by a crusher to obtain a powdery sample 2, and the sample 2 is subjected to performance test analysis.
Composition of the components | Sample 2 |
Packing material | 82 |
Epoxy resin and phenolic hardener | 15.5 |
Catalyst | 0.4 |
Toughening agent | 0.3: structure II |
Others | 1.8 |
Comparative example:
(1) Toughening agent-side group epoxy modified polysiloxane
Purchased from japanese daokannin; trade name: SF 8421EG fluid; CAS number: 556-67-2.
(2) Preparation of Epoxy Molding Compound (EMC)
According to the following table formulation, crystalline SiO 2 The filler, EOCN epoxy resin, OCN phenolic resin curing agent, triphenylphosphine catalyst, toughening agent (dakangning 8421) and other functional auxiliary agents are uniformly mixed by a high-speed stirrer, and are further kneaded and mixed by a double-screw extruder, the discharging temperature is controlled to be not higher than 118 ℃, the discharged materials are cooled by a calender and a cooling belt, and then crushed by a crusher to obtain a powdery sample 3, and the sample 3 is subjected to performance test analysis.
Composition of the components | Sample 3 |
Packing material | 82 |
Epoxy resin and phenolic hardener | 15.5 |
Catalyst | 0.4 |
Toughening agent | 0.3: daokanning 8421 |
Others | 1.8 |
The EMC performance evaluation results prepared in examples and comparative examples are shown in the following table:
from the comparison of the data of the sample 1, the sample 2 and the sample 3 in the table, compared with the sample 3, the modulus of the sample 1 and the sample 2 is obviously reduced, which indicates that the terminal phenolic hydroxyl group modified polysiloxane has better toughening effect than the traditional side group epoxy modified polysiloxane; meanwhile, the modulus data of the sample 1 and the sample 2 are compared, and the modulus of the sample 2 is lower, namely the toughening effect is better than that of the sample 1, which is attributed to the fact that the benzene ring of the structure of the sample 2 has no methoxy substituent group, and the reactivity of phenol is higher. In summary, the phenolic hydroxyl-terminated modified polysiloxane has excellent toughening effect in EMC materials for semiconductor encapsulation.
Claims (9)
1. The phenolic hydroxyl-terminated modified polysiloxane is characterized in that the polysiloxane has a chemical structural formula selected from one of I and II:
wherein n represents the number of repeating units and the value range is an integer between 0 and 50.
2. A method for preparing a phenolic hydroxyl-terminated modified polysiloxane, which is characterized in that the synthesis of the structural formula I comprises the following synthesis steps:
polysiloxane containing terminal hydrogen and chloroplatinic acid (H) 2 PtCl·6H 2 O) and a trace amount of polymerization inhibitor p-hydroxyanisole (MEHQ) are added into a 500ml three-necked round bottom flask containing tetrahydrofuran, the three-necked round bottom flask is provided with a stirrer, a dropping funnel and a reflux condensing device, and the substances are heated under stirring; 2-methoxy-4- (2-propenyl) phenol (eugenol) was dissolved in tetrahydrofuran and added dropwise through a dropping funnel; after the reaction, volatile matters were removed under reduced pressure to obtain a pale yellow liquid product.
3. A preparation method of phenolic hydroxyl-terminated modified polysiloxane is characterized in that the synthesis of the structural formula II comprises the following synthesis steps:
polysiloxane containing terminal hydrogen and chloroplatinic acid (H) 2 PtCl·6H 2 O) and a trace amount of polymerization inhibitor p-hydroxyanisole (MEHQ) are added into a 500ml three-necked round bottom flask containing tetrahydrofuran, the three-necked round bottom flask is provided with a stirrer, a dropping funnel and a reflux condensing device, and the substances are heated under stirring; dissolving 4-allyloxyphenol in tetrahydrofuran and adding dropwise through a dropping funnel; after the reaction, volatile matters were removed under reduced pressure to obtain a pale yellow liquid product.
4. The toughening application of the phenolic hydroxyl-terminated modified polysiloxane in the epoxy molding compound is characterized in that the phenolic hydroxyl-terminated modified polysiloxane in claim 1 is mixed with epoxy resin, phenolic resin curing agent, catalyst and other functional auxiliary agents, and then the Epoxy Molding Compound (EMC) is obtained through production.
5. The toughening application of the phenolic hydroxyl-terminated modified polysiloxane in the epoxy molding compound of claim 4, wherein the epoxy resin is selected from any one or a combination of the following structures:
6. the toughening application of the phenolic hydroxyl-terminated modified polysiloxane in the epoxy molding compound of claim 4, wherein the phenolic resin curing agent is selected from any one or a combination of the following structures:
7. the toughening application of the phenolic hydroxyl-terminated modified polysiloxane in the epoxy molding compound, according to claim 4, wherein the structure of the catalyst is selected from any one or more of imidazole and derivatives thereof, organic amine compounds, triphenylphosphine and derivatives thereof, and phosphonium salt compounds.
8. The toughening application of the phenolic hydroxyl terminated modified polysiloxane in the epoxy plastic packaging material according to claim 4, wherein the formula comprises the following components:
and (3) filling: 82 parts;
epoxy resin and phenolic curing agent: 15.5 parts;
catalyst: 0.4 parts;
toughening agent: 0.3 part of toughening agent which is one of terminal phenolic hydroxyl modified polysiloxane of a structural formula I and terminal phenolic hydroxyl modified polysiloxane of a structural formula II;
other functional auxiliaries: 1.8 parts.
9. The toughening application of the phenolic hydroxyl-terminated modified polysiloxane in the epoxy plastic packaging material according to claim 4, wherein the specific production steps of the preparation comprise the following production steps:
(a) Uniformly mixing epoxy resin, phenolic resin curing agent, catalyst, toughening agent and other functional auxiliary agents by a high-speed stirrer to obtain a premix;
(b) And further kneading and mixing the premix by a double screw extruder, and cooling and crushing the extrudate to prepare the EMC material.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN202311777284.0A CN117720732A (en) | 2023-12-22 | 2023-12-22 | Preparation method of phenolic hydroxyl-terminated modified polysiloxane and toughening application of phenolic hydroxyl-terminated modified polysiloxane in epoxy plastic packaging material |
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Application Number | Priority Date | Filing Date | Title |
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CN202311777284.0A CN117720732A (en) | 2023-12-22 | 2023-12-22 | Preparation method of phenolic hydroxyl-terminated modified polysiloxane and toughening application of phenolic hydroxyl-terminated modified polysiloxane in epoxy plastic packaging material |
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Publication Number | Publication Date |
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CN117720732A true CN117720732A (en) | 2024-03-19 |
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CN202311777284.0A Pending CN117720732A (en) | 2023-12-22 | 2023-12-22 | Preparation method of phenolic hydroxyl-terminated modified polysiloxane and toughening application of phenolic hydroxyl-terminated modified polysiloxane in epoxy plastic packaging material |
Country Status (1)
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CN (1) | CN117720732A (en) |
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- 2023-12-22 CN CN202311777284.0A patent/CN117720732A/en active Pending
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