橡胶籽油基类环氧丙烯酸酯树脂的合成及其性能研究

doi:10.3969/j.issn.0253-2417.2020.04.013

Abstract

Abstract:

Epoxidized rubber seed oil (ERSO) and hydroxyethyl methacrylate maleate (HEMAMA) precursors underwent epoxide-opening reaction to prepare a new rubber seed oil-based epoxy acrylate (HMMERSO). Polymer and its chemical structure were confirmed by FT-IR and ¹H NMR. The final properties of the photocurable materials obtained by mixing HMMERSO with different diluents were also studied. The obtained HMMERSO had 4.85 C=C functional groups in per triglyceride molecule, and the bio-based content was 71.2%. The HMMERSO material was found to exhibit excellent performance. The storage modulus of HMMERSO material at normal temperature could reach 752.8 MPa, the glass transition temperature (T_g) was 67.4 ℃ and the tensile strength and modulus were 9.84 and 365.5 MPa, which were 7.7, 4, 5.1 and 9.7 times of the values of the epoxidized soybean oil acrylate(AESO) material, respectively. The performance of the material modified with 30% hydroxyethyl methacrylate diluent was better, and its tensile strength reached 26.1 MPa and T_g reached 90.9 ℃.

Key words: rubber seed oil, epoxy acrylate, photocurable coating

CLC Number:

TQ35

Jianyu LU,Qiong WU,Jijun TANG,Xiaoli REN,Yonghong ZHOU,Chengguo LIU. Synthesis and Property of Rubber Seed Oil-based Epoxy Acrylate Resin[J]. Chemistry and Industry of Forest Products, 2020, 40(4): 93-99.

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References 15

1	严剑刚, 罗俊, 严永源. UV固化灯电极加工工艺研究[J]. 热加工工艺, 2018, 12 (6): 124- 127.
	YAN J G , LUO J , YAN Y Y . Study on the processing technology of UV curing lamp electrode[J]. Hot Working Technology, 2018, 12 (6): 124- 127.
2	张恒, 许磊, 胡振华, 等. 光固化3D打印用光敏树脂的研究进展[J]. 合成树脂及塑料, 2015, 32 (4): 81- 84.
	ZHANG H , XU L , HU Z H , et al. Research progress of photosensitive resin for photocuring 3D printing[J]. China Synthetic Resin and Plastics, 2015, 32 (4): 81- 84.
3	MANDAL M , MAJI T K . Comparative study on the properties of wood polymer composites based on different modified soybean oils[J]. Journal of Wood Chemistry and Technology, 2017, 37 (2): 124- 135.
4	LU J , KHOT S , WOOL R P . New sheet molding compound resins from soybean oil.I:Synthesis and characterization[J]. Polymer, 2005, 46 (1): 71- 80.
5	LIU C , DAI Y , WANG C , et al. Phase-separation dominating mechanical properties of a novel tung-oil-based thermosetting polymer[J]. Industrial Crops and Products, 2012, 43 (1): 677- 683.
6	杨晓琴, 郑志锋, 郑云武, 等. 橡胶籽油的分析表征[J]. 食品工业科技, 2016, 37 (24): 122- 125, 131.
	YANG X Q , ZHENG Z F , ZHENG Y W , et al. Analysis and characterization of rubber seed oil[J]. Science and Technology of Food Industry, 2016, 37 (24): 122- 125, 131.
7	黄元波, 郑志锋, 马焕, 等. 橡胶籽油基多元醇的制备与表征[J]. 生物质化学工程, 2017, 51 (5): 22- 26.
	HUANG Y B , ZHENG Z F , MA H , et al. Preparation and characterization of rubber seed oil-based polyols[J]. Biomass Chemical Engineering, 2017, 51 (5): 22- 26.
8	潘晓威, 叶剑芝, 曾绍东, 等. 橡胶籽资源的研究开发现状[J]. 现代农业科技, 2019, 24 (12): 131- 135.
	PAN X W , YE J Z , ZENG S D , et al. Research and development status of rubber seed resources[J]. Modern Agricultural Science and Technology, 2019, 24 (12): 131- 135.
9	CHEN Z , CHISHOLM B J , WEBSTER D C , et al. Study of epoxidized-cardanol containing cationic UV curable materials[J]. Progress in Organic Coatings, 2009, 65 (2): 246- 250.
10	LI K , SHEN Y , FEI G , et al. Preparation and properties of castor oil/pentaerythritol triacrylate-based UV curable waterborne polyurethane acrylate[J]. Progress in Organic Coatings, 2015, 78 (9): 146- 154.
11	庞来兴, 杨建文, 黄玉刚. 新型环氧大豆油丙烯酸酯类UV树脂的合成与表征[J]. 合成材料老化与应用, 2013, 42 (6): 8- 11.
	PANG L X , YANG J W , HUANG Y G . Synthesis and characterization of new epoxy soybean oil acrylate UV resin[J]. Synthetic Materials Aging and Application, 2013, 42 (6): 8- 11.
12	ZOU K , SOUCEK M D . UV-curable cycloaliphatic epoxide based on modified linseed oil:Synthesis, characterization and kinetics[J]. Macromolecular Chemistry & Physics, 2005, 206 (9): 967- 975.
13	ZONG Z , HE J , SOUCEK M D . UV-curable organic-inorganic hybrid films based on epoxynorbornene linseed oils[J]. Advanced Materials Research, 2011, 53 (2): 217- 299. 217-218, 294-299
14	WU Q , HU Y , TANG J , et al. High-performance soybean oil-based epoxy acrylate resins:"Green" synthesis and application in UV-curable coatings[J]. ACS Sustainable Chemistry & Engineering, 2018, 6 (7): 8340- 8349.
15	LIU C , DAI Y , HU Y , et al. Highly functional unsaturated ester macromonomer derived from soybean oil:Synthesis and copolymerization with styrene[J]. ACS Sustainable Chemistry & Engineering, 2016, 4 (8): 4208- 4216.

样品 samples	25℃储存模量 (E′₂₅)/MPa 25℃ storage modulus	玻璃化转变温度(T_g)/℃ transition temp.	交联密度(ν_e)/ (mol·m^-3) crosslinking density	5%热失重温度(T₅)/℃ 5% weight loss temp.	最大热降解温度(T_p)/℃ maximum thermal degradation temp.	成炭率 (w_char)/% char yield
HMMERSO	752.8	67.4	4.63×10³	279.9	421.4	3.3
AESO	96.9	16.9	3.63×10³	332.8	398.7	2.1
HMMERSO/HEA30	624.5	47.2	2.47×10³	285.9	423.9	5.5
HMMERSO/HEMA30	1287.0	90.9	2.24×10³	273.4	425.5	3.1
HMMERSO/TEGDA30	1005.0	77.1	7.91×10³	301.3	430.3	3.0
HMMERSO/TMPTA30	1445.0	69.3	41.30×10³	312.9	458.7	3.9

样品 samples	拉伸强度/MPa tensile strength	拉伸模量/MPa tensile modulus	断裂伸长率/% elongation at break	漆膜附着力 film adhesion	铅笔硬度 pencil hardness	漆膜柔韧性/mm flexibility of paint film
HMMERSO	9.84±0.88	365.5±23.4	5.2±0.2	2	2B	2
AESO	1.93±0.12	37.7±1.8	5.9±0.2	3	4B	2
HMMERSO/HEA30	12.1±0.77	355.5±40.9	11.7±2.3	2	3H	2
HMMERSO/HEMA30	26.1±0.2	391.9±15.1	7.8±0.7	2	2H	2
HMMERSO/TEGDA30	13.3±1.1	622.9±24.4	3.8±0.3	2	H	3
HMMERSO/TMPTA30	8.09±0.7	1009.4±36.0	2.3±0.7	2	2B	2

[1]	ZHANG Fei, HU Yun, LIU Chengguo, ZHOU Yonghong. Synthesis and Characterization of Hydroxylated Woody Oil [J]. Chemistry and Industry of Forest Products, 2018, 38(6): 27-32.
[2]	YANG Jing;XIE Chao;XU Juan;HUANG Yuan-bo;LIU Shou-qing;ZHENG Yun-wu;ZHENG Zhi-feng;. Separation and Characterization of Polyunsaturated Fatty Acids from Rubber Seed Oil [J]. , 2013, 33(2): 49-54.

Synthesis and Property of Rubber Seed Oil-based Epoxy Acrylate Resin

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