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Rosin or rosin derivative long chain flexible monomer preparation method

A technology of rosin derivatives and flexible monomers, which is applied in the field of preparation of rosin or rosin derivatives long-chain flexible monomers, achieving the effect of wide application prospects

Inactive Publication Date: 2013-08-07
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

[0004] In order to solve the problem of the flexibility of the rosin-based monomer after the homopolymerization reaction, the present invention adopts the method of first introducing the flexible chain and then introducing the acrylate function to synthesize the rosin-based monomer

Method used

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  • Rosin or rosin derivative long chain flexible monomer preparation method
  • Rosin or rosin derivative long chain flexible monomer preparation method
  • Rosin or rosin derivative long chain flexible monomer preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] The first step is to dissolve rosin or rosin derivatives in dichloromethane or tetrahydrofuran, add an acid chloride reagent, and react at 0-85°C for 1-12 hours to synthesize rosin or rosin derivative acid chlorides; the rosin can be selected from gum rosin, Tall rosin and wood rosin. Rosin derivatives can be hydrogenated rosin, disproportionated rosin, acrylic rosin, maleic rosin, dehydroabietic acid, L-pimaric acid, maleopimaric acid, isopimaric acid; the acid chloride reagent can be oxalyl chloride (C 2 o 2 Cl 2 ), phosphorus trichloride (PCl 3 ), phosphorus pentachloride (PCl 5 ), thionyl chloride (SOCl 2 ), phosphorus oxychloride (POCl 3 ); the temperature can be selected from 0°C, 10°C, 20°C, 30°C, 40°C, 50°C, 60°C, 70°C, 80°C, 85°C. The reaction time can be selected from 1 hour, 2 hours, 3 hours, 4 hours, 5 hours, 6 hours, 7 hours, 8 hours, 9 hours, 10 hours, 11 hours, 12 hours;

[0032] The second step is to mix rosin or rosin derivative acid chloride wit...

Embodiment 2

[0035] Synthesis of dehydroabietic acid-1,6-hexanediol-based long-chain flexible monomer

[0036] The synthetic route is shown below,

[0037]

[0038]In order to prepare flexible resin acid-based soft monomers, first connect hexanediol to dehydroabietic acid (DA), and use excess hexanediol (hexanediol / dehydroabietic acid=10 / 1 (molar ratio)) Dehydroabietic acid-1,6-hexanediol monoester can be efficiently synthesized with dehydroabietic acid chloride (DA-Cl), and then dehydroabietic acid-1 can be synthesized by reacting with a slight excess of methacryloyl chloride, 6-Hexanediol-based monomer;

[0039] The synthesis steps are:

[0040] (1) Add 1.00g of dehydroabietic acid (0.0033mol) into the reactor, dissolve it with 30ml of dichloromethane, add 0.6ml of oxalyl chloride (0.0055mol), and react at 25°C for 3 hours to obtain dehydroabietic acid chloride; ( 2) Add 4.10 g (0.033 mol) of catalyst 4-dimethylaminopyridine (DMAP) and 0.033 mol of 1,6-hexanediol to the reaction pr...

Embodiment 3

[0043] Synthesis of dehydroabietic acid-1,6-hexanediol-based long-chain flexible monomer

[0044] The synthetic route is shown below,

[0045]

[0046] The synthesis steps are:

[0047] (1) Add 1.00g of dehydroabietic acid (0.0033mol) into the reactor, dissolve it with 30ml of dichloromethane, add 0.6ml of oxalyl chloride (0.0055mol), and react at 25°C for 3 hours to obtain dehydroabietic acid chloride; ( 2) Add 4.10 g (0.033 mol) of catalyst 4-dimethylaminopyridine (DMAP) and 0.033 mol of 1,6-hexanediol to the reaction product of the first step, and react at 50° C. for 12 hours. The DMAP salt was filtered off, the resulting filtrate was dropped into petroleum ether and the corresponding precipitate was filtered off again, the filtrate was collected, and the solvent was removed to obtain 1.00 g of dehydroabietic acid-1,6-hexanediol monoester. (3) Add 0.40 g (1.0 mmol) of dehydroabietic acid-1,6-hexanediol monoester, 2.5 mmol of catalyst triethylamine (TEA) and 0.00010 g o...

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Abstract

The present invention relates to a rosin or rosin derivative long chain flexible monomer preparation method, which comprises the following steps: 1) placing rosin or a rosin derivative in dichloromethane or tetrahydrofuran, adding an acyl chlorination reagent, carrying out a reaction for 1-12 h at a temperature of 0-85 DEG C to synthesize rosin acyl chloride or rosin derivative acyl chloride; 2) mixing the rosin acyl chloride or the rosin derivative acyl chloride and a long chain aliphatic diol according to a certain molar ratio, dissolving in tetrahydrofuran, adding a catalyst, carrying out a reaction for 5-24 h at a temperature of 50-80 DEG C to synthesize rosin long chain aliphatic diol monoester or rosin derivative long chain aliphatic diol monoester, and carrying out precipitation purification in a specific solvent; and (3) mixing the purified rosin long chain aliphatic diol monoester or the purified rosin derivative long chain aliphatic diol monoester and acryloyl chloride or methacryloyl chloride according to a certain molar ratio, adding a catalyst and a polymerization inhibitor hydroquinone, and carrying out a reaction for 4-24 h at a temperature of -10-10 DEG C to synthesize a rosin long chain flexible monomer or a rosin derivative long chain flexible monomer, wherein the synthesized rosin long chain flexible monomer or the synthesized rosin derivative long chain flexible monomer can be subjected to a free radical polymerization reaction.

Description

technical field [0001] The invention relates to a preparation method of rosin or a rosin derivative long-chain flexible monomer, and the synthesis of a resin acid-based monomer with a low glass transition temperature after polymerization. Background technique [0002] Acrylate monomer is a very important chemical raw material. Through free radical polymerization, acrylate monomer can synthesize a class of resin with aging resistance, light resistance, non-yellowing, high strength and good water resistance. This resin has been widely used in Energy, medical, construction, health, food, machinery manufacturing, packaging, adhesives and coatings and many other fields. After decades of development, the structure of acrylic acid monomers has developed from a single functionality, such as methyl methacrylate, to a multi-functionality, propoxylated glycerol triacrylate; from small molecular compounds to oligomers, such as Epoxy acrylate, urethane acrylate, polyester acrylate, etc....

Claims

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Application Information

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IPC IPC(8): C07C69/753C07C67/14C07J73/00
Inventor 王基夫俞娟刘玉鹏储富祥王春鹏
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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