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Free radical-polymerizable rosin-modified benzocyclobutene monomer, preparation method and application thereof

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

Active Publication Date: 2019-01-11
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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  • Free radical-polymerizable rosin-modified benzocyclobutene monomer, preparation method and application thereof
  • Free radical-polymerizable rosin-modified benzocyclobutene monomer, preparation method and application thereof
  • Free radical-polymerizable rosin-modified benzocyclobutene monomer, preparation method and application thereof

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-modified benzocyclobutene monomer, a preparation method thereof, and a benzocyclobutene resin prepared from the monomer. The molecular structural formula of the free radical-polymerizable rosin-modified benzocyclobutene monomer is shown in the description. The preparation method of the free radical-polymerizable rosin-modified benzocyclobutene monomer is characterized in that dehydroabietic acid used as a raw material sequentially undergoes bromination, Suzuki coupling and esterification reactions to prepare the free radical-polymerizable rosin-modified benzocyclobutene monomer. The free radical-polymerizable rosin-modified benzocyclobutene monomer can be subjected to free radical polymerization and ring-opening polymerization, thefunctional monomer synthesized through multiple reactions is used to prepare a polymer material, and the thermal stability, the water resistance and the dielectric property of the resin prepared fromthe free radical-polymerizable rosin-modified benzocyclobutene monomer are improved; and the preparation method enhances the reprocessing utilization of rosin, improves the use values of the rosin, and reduces the use of petrochemical resources.

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 coefficient and other properties. Based on these excellent properties, BCB resin has been widel...

Claims

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Application Information

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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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