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A kind of free radical polymerizable rosin benzocyclobutene monomer, its preparation method and application

A technology of benzocyclobutene and polymerized rosin, applied in the field of rosin benzocyclobutene monomer, can solve problems such as unsatisfactory performance, and achieve the effects of improving use value, reducing use, and strengthening reprocessing and utilization

Active Publication Date: 2021-02-19
INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A single BCB resin material can no longer meet the requirements of these applications in terms of performance, so it is necessary to introduce other groups to improve the performance of BCB resin

Method used

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  • A kind of free radical polymerizable rosin benzocyclobutene monomer, its preparation method and application
  • A kind of free radical polymerizable rosin benzocyclobutene monomer, its preparation method and application
  • A kind of free radical polymerizable rosin benzocyclobutene monomer, its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] The monomer prepared in this embodiment is: 12-position benzocyclobutene dehydroabietic acid allyl alcohol ester, the structure is as follows:

[0047]

[0048] The preparation process is as follows:

[0049] 1) Add 5.00 g of starting materials dehydroabietic acid, 5.54 g of NBS, and 337 mL of anhydrous acetonitrile into a round-bottomed flask, react at 25°C in the dark for 24 hours, filter with suction, dissolve the solid in ethyl acetate, add H 2 O was extracted, and the aqueous phase was washed with ethyl acetate (50mL×2), and the combined organic phases were washed with H 2 The organic phase was washed with O (50 mL×2); after that, it was washed with anhydrous Na 2 SO 4 Dry the organic phase, filter, and rotary evaporate to obtain a white solid substance: 12-bromodehydroabietic acid, the purity is greater than 95%, and the yield is greater than 90%. The product structure of this step is characterized by: 1H NMR (400MHz, DMSO) δ12.20(s, 1H), 7.36(s, 1H), 7.00(s...

Embodiment 2

[0054] The monomer prepared in this embodiment is: 12-position benzocyclobutene dehydroabietic acid allyl alcohol ester, the structure is as follows:

[0055]

[0056] The preparation process is as follows:

[0057] 1) Add 5.00 g of starting materials dehydroabietic acid, 5.54 g of NBS, and 300 mL of anhydrous acetonitrile into a round-bottomed flask, react at 25°C in the dark for 24 hours, filter with suction, dissolve the solid in ethyl acetate, add H 2 O was extracted, and the aqueous phase was washed with ethyl acetate (50mL×2), and the combined organic phases were washed with H 2 The organic phase was washed with O (50 mL×2); after that, it was washed with anhydrous Na 2 SO 4 Dry the organic phase, filter, and rotary evaporate to obtain a white solid substance: 12-bromodehydroabietic acid, the purity is greater than 95%, and the yield is greater than 90%. The product structure of this step is characterized by: 1 H NMR (400MHz, DMSO) δ12.20(s, 1H), 7.36(s, 1H), 7.00(...

Embodiment 3

[0061] Preparation of monomer

[0062] 12-bromodehydroabietic acid (the product obtained in step 1 of Example 1)) 0.419g, 0.185g of 4-boronic acid benzocyclobutene were dissolved in 10mL of dioxane, and were added to a three-necked flask and then Add potassium carbonate 0.255g, in N 2 Under protection, add tetrakis triphenylphosphine palladium 0.005g; 2 At 75°C, react for 8 hours, cool to room temperature, wash with diatomaceous earth and ethyl acetate, add H 2 O extraction; the aqueous phase was washed (50mL×2) with ethyl acetate, and the combined organic phases were washed with H 2 O washes the organic phase (50 mL×2); after that anhydrous Na 2 SO 4 The organic phase was dried, filtered, and rotary evaporated to obtain a white solid: 12-position benzocyclobutene dehydroabietic acid. The product structure of this step was characterized by: 1 H NMR(500MHz,DMSO)δ12.16(s,1H),7.10(d,J=7.5Hz,1H),7.02(dd,J=7.5,0.9Hz,1H),7.00(s,1H),6.93 (s,1H),6.91(s,1H).

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Abstract

The invention discloses a free radical polymerizable rosin benzocyclobutene monomer, a preparation method thereof and the prepared benzocyclobutene resin, a free radical polymerizable rosin benzocyclobutene monomer, and its molecular The structural formula is: the preparation method of the above-mentioned free-radical polymerizable rosin benzocyclobutene monomer is as follows, using dehydroabietic acid as a raw material, successively undergoing bromination, Suzuki coupling and esterification reactions to obtain free-radical polymerizable Rosin benzocyclobutene monomer. The free radical polymerizable rosin benzocyclobutene monomer of the present invention can undergo free radical polymerization and ring-opening post-polymerization, and synthesize functional monomers to prepare polymer materials through various reaction pathways. Using the free radical polymerizable monomer of this application The thermal stability, water resistance and dielectric properties of the resin prepared by the rosin benzocyclobutene monomer are all improved; the reprocessing and utilization of rosin are strengthened, the use value of rosin is improved, and the use of petrochemical resources is reduced.

Description

technical field [0001] The invention relates to a free radical polymerizable rosin benzocyclobutene monomer, a preparation method and application thereof, and belongs to the field of organic synthesis. Background technique [0002] In recent years, rosin modified molecular materials have been widely used in surfactants, ink coatings, food industry, papermaking additives, pharmaceuticals and pesticides, etc., and rosin modified polymer materials will also replace the previous petrochemical raw materials. On the one hand It can reduce the damage to the environment, and on the other hand, it can slow down the exhaustion of oil resources. [0003] As a new type of active resin, benzocyclobutene (BCB) resin can form both thermoplastic resin and thermosetting resin, and its resin has excellent thermal stability, molding processability, low dielectric constant and low thermal expansion coefficients and other properties. Based on these excellent properties, BCB resin has been wide...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/753C07C67/11C08F118/10
CPCC07C69/753C08F118/10C07C2602/06C07C2603/26
Inventor 王丹付飞沈明贵商士斌宋湛谦宋杰
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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