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Preparation method of castor-oil base branched polybasic cyclic carbonate and non-isocyanate polyurethane thereof

An oil-based non-isocyanate and polyurethane technology, applied in polyurea/polyurethane coatings, organic chemistry, coatings, etc., can solve the problem of reduced reactivity, low number of cyclocarbonates, and poor design and control of cyclocarbonate groups To achieve the effect of high reactivity and high renewable carbon content

Active Publication Date: 2016-03-02
JIANGXI SCI & TECH NORMAL UNIV
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AI Technical Summary

Problems solved by technology

The renewable carbon content of the obtained vegetable oil-based cyclocarbonate prepared by this method is 100%, but it needs to be reacted for a long time in a special reactor under high temperature, high pressure and the presence of a catalyst. Located in the unsaturated fatty acid chain, the epoxy group after epoxidation is in the same position as the double bond, and the insertion rate of carbon dioxide is not high due to the steric effect, resulting in a low number of cyclic carbonates inserted, and This type of method cannot be well designed to control the number of access of cyclic carbonate groups in vegetable oil; the prepared cyclic carbonate groups are directly connected to vegetable oil fatty acid chains without spacers, and are easily covered and entangled by long chains of fatty acids And reduce its reactivity as a polyurethane preparation prepolymer

Method used

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  • Preparation method of castor-oil base branched polybasic cyclic carbonate and non-isocyanate polyurethane thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] 1) Preparation of mercapto cyclocarbonate

[0021] Add 11.8g of glycerol cyclocarbonate, 13g of 3-mercaptopropionic acid, 1.24g of p-toluenesulfonic acid, and 40ml of dichloromethane into the reaction flask, and reflux at 80°C for 8h. After the solution was washed three times with deionized water, it was dried with anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation to obtain 16.27 g of mercapto cyclocarbonate with a yield of 79%. Its NMR data are as follows:

[0022] 1 HNMR (400MHz, CDCl 3 , δppm) 4.95 (ddd, J = 9.1, 6.1, 3.8Hz, 1H), 4.58 (t, J = 8.6Hz, 1H), 4.43 (dd, J = 12.6, 3.3Hz, 1H), 4.35 (dd, J =5.2,2.6Hz,1H),4.32(d,J=5.3Hz,1H),2.81(td,J=7.9,4.0Hz,2H),2.74(dd,J=10.2,3.9Hz,2H),1.71 -1.61(m,1H).

[0023] 13 CNMR (100MHz, CDCl 3 ,δppm) 171.18(OC=O), 154.56(OC(O)O), 73.82(CH), 65.19(CH 2 ), 63.24 (CH 2 ), 38.09 (CH 2 ), 19.45 (CH 2 ).

[0024] 2) Preparation of castor oil-based polyols with an average hydroxyl group functionali...

Embodiment 2

[0035] 1) Preparation of castor oil-based polyols with an average hydroxyl group functionality of 5.7

[0036] Add 9g of castor oil, 3.78g of 2-mercaptoethanol, 0.20g of photoinitiator 2,2-diethoxyacetophenone and 20ml of dichloromethane into the reactor, react under ultraviolet light for 8h at room temperature, and use deionized Excessive 2-mercaptoethanol was removed by water washing, the organic layer was dried with anhydrous magnesium sulfate, and methylene chloride was removed by rotary evaporation to obtain 9.77g of castor oil-based polyol with an average hydroxyl group functionality of 5.7, and the double bond reaction was determined to be complete by NMR technology. The yield was 87.1%.

[0037] 2) Preparation of castor oil-based branched polyolefins with an average carbon-carbon double bond functionality of 5.7

[0038] Add 4 g of castor oil-based polyols with an average hydroxyl group functionality of 5.7, 3.44 g of triethylamine and 30 ml of ethyl acetate into the ...

Embodiment 3

[0046]The preparation of the castor oil-based multi-branched cyclocarbonate whose cyclocarbonate average functionality is 6.8:

[0047] Add 7.48g of castor oil-based branched polyolefins with an average carbon-carbon double bond functionality of 8.7, 3.5g of mercapto cyclocarbonate, 0.15g of 2-hydroxy-2-methyl-1-phenylacetone and 10ml of chloroform Into the reactor, react under ultraviolet light at room temperature for 12 hours, and remove the solvent by rotary evaporation to obtain 10.98 g of castor oil-based polycyclic carbonate with an average functionality of cyclic carbonate of 6.8. Its NMR data are as follows:

[0048] 1 HNMR (400MHz, CDCl 3 , δppm) 5.82 (td, J = 14.3, 6.2Hz, 2.7H), 5.20 (s, 1H), 5.02 (dd, J = 18.4, 12.3Hz, 12H), 4.65 (dt, J = 15.4, 7.7Hz, 6H), 4.48-4.15(m, 25H), 4.03-3.85(m, 2H), 2.97(dd, J=20.1, 13.3Hz, 6H), 2.78(ddt, J=24.6, 12.6, 6.0Hz, 36H) ,2.54(t,J=7.3Hz,14H),2.42-2.23(m,17H),2.19-1.99(m,6H),1.87-1.73(m,5H),1.72-1.46(m,37H),1.27 (dd, J=14.4, ...

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Abstract

The present invention discloses a preparation method of castor-oil base branched polybasic cyclic carbonate and non-isocyanate polyurethane thereof. The method is as below: raw materials of 10-undecylenic acid modified castor-oil base branched polyenoid prepolymer and thiol cyclic carbonate and a solvent chloroform are subjected to UV radiation reaction in the presence of a photoinitiator for 6-15 h to obtain a castor-oil base polybasic branched cyclic carbonate prepolymer; and the prepolymer further reacts with an amino compound to prepare the castor-oil base non-isocyanate polyurethane. The preparation of the cyclic carbonate does not require high temperature, high pressure or catalyst, and can well control the graft number of cyclic carbonate groups in the vegetable oil; and the prepared cyclic carbonate has branched structure and lower viscosity, and has long space group from a vegetable oil connection point, so that the cyclic carbonate group at the end has very high reactivity. The castor-oil base polyurethane material has the advantages of biodegradability and high content of renewable carbon, and can be used as renewable polyurethane resin for paint.

Description

technical field [0001] The invention discloses a preparation method of castor oil-based branched polycyclic cyclic carbonate and non-isocyanate polyurethane, in particular to a castor oil-based branched polycyclic cyclic carbonate prepolymer modified with 10-undecylenic acid and Its non-isocyanate polyurethane preparation method. Background technique [0002] Non-isocyanate polyurethane (NIPU) is prepared by the copolymerization reaction of polycyclic carbonate prepolymer and polyamine. Compared with polyisocyanate polyurethane, it not only avoids the use of more toxic isocyanate, but also retains the excellent mechanical properties of traditional polyurethane materials. , and because there is no urethane bond in its main chain structure, it makes up for the shortcomings of traditional polyisocyanate polyurethane in terms of hydrolysis stability and impermeability from the molecular structure, and it has excellent chemical resistance and water resistance. and impermeability...

Claims

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Application Information

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IPC IPC(8): C08G71/04C07D317/36C09D175/04
CPCC07D317/36C08G71/04C09D175/04
Inventor 付长清申亮李文才
Owner JIANGXI SCI & TECH NORMAL UNIV
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