植物油脂基压敏胶的研究进展及动态

doi:10.3969/j.issn.1673-5854.2022.01.007

摘要/Abstract

摘要：

以天然可再生的植物油脂为原料制备压敏胶是解决目前石油基压敏胶基料资源短缺和环境问题的有效途径，也是目前学术研究和应用开发的热点之一。笔者综述了近年来国内外研究者在植物油脂基压敏胶方面的研究进展，按照植物油基高分子的种类(环氧树脂、丙烯酸树脂、脂肪酸衍生物、聚酯及聚氨酯等)进行了分类，重点总结了植物油脂基压敏胶基体的设计思路以及改性方法，在此基础上探讨了植物油脂基压敏胶改性研究方向(包括功能型植物油单体的开发、聚合物结构的优化等)，以期为设计发展新型的生物基压敏胶材料提供可行的理论与参考。

关键词: 植物油脂, 压敏胶, 高分子功能化, 脂肪酸

Abstract:

Using natural and renewable plant oils as raw materials to prepare pressure-sensitive adhesives is an effective way to solve the current resource shortage and environmental problems of petroleum-based pressure-sensitive adhesives, it is also one of the hotspots in academic research and application development. The author reviewed the research progress of plant oil-based pressure-sensitive adhesives by domestic and foreign researchers in recent years. And the adhesives were classified according to the types of plant oil-based polymers (epoxy resin, acrylic resin, fatty acid derivatives, polyester and polyurethane, etc.), and the design ideas and modification methods of these research were emphatically summarized. On this basis, the development of new plant oil monomer structure and copolymerization with functional monomer were discussed, so as to provide a feasible theory and reference for the design and development of new bio-based pressure sensitive adhesive materials.

Key words: plant oil, pressure sensitive adhesive, polymer functionalization, fatty acid

中图分类号:

TQ35
TB34

刘伟, 王钟, 汪钟凯. 植物油脂基压敏胶的研究进展及动态[J]. 生物质化学工程, 2022, 56(1): 47-56.

Wei LIU, Zhong WANG, Zhongkai WANG. Research Progress and Dynamic State of Plant Oil-based Pressure-sensitive Adhesives[J]. Biomass Chemical Engineering, 2022, 56(1): 47-56.

图/表 4

参考文献 53

1	李自夏, 冉印. 压敏胶研究综述[J]. 广东化工, 2020, 47 (10): 53- 54. doi: 10.3969/j.issn.1007-1865.2020.10.024
2	VENDAMME R, SCHUWER N, EEVERS W. Recent synthetic approaches and emerging bio-inspired strategies for the development of sustainable pressure-sensitive adhesives derived from renewable bbuilding blocks[J/OL]. Journal of Applied Polymer Science, 2014, 131(17): 40669[2020-10-20]. https://doi.org/10.1002/app.40669.
3	SUN S M , LI M L , LIU A . A review on mechanical properties of pressure sensitive adhesives[J]. International Journal of Adhesion and Adhesives, 2013, 41, 98- 106. doi: 10.1016/j.ijadhadh.2012.10.011
4	COHEN E , BINSHTOK O , DOTAN A , et al. Prospective materials for biodegradable and/or biobased pressure-sensitive adhesives: A review[J]. Journal of Adhesion Science and Technology, 2013, 27 (18/19): 1998- 2013.
5	LLIGADAS G , RONDA J C , GALIA M , et al. Renewable polymeric materials from vegetable oils: A perspective[J]. Materials Today, 2013, 16 (9): 337- 343. doi: 10.1016/j.mattod.2013.08.016
6	MOLINA-GUTIERREZ S , LADMIRAL V , BONGIOVANNI R , et al. Radical polymerization of biobased monomers in aqueous dispersed media[J]. Green Chemistry, 2019, 21 (1): 36- 53. doi: 10.1039/C8GC02277A
7	何鑫, 吴桂英, 闫云君. 植物油基平台化合物及高分子材料研究进展[J]. 生物工程学报, 2017, 33 (5): 701- 719.
8	LORENZ C D , STEVENS M J , WOOL R P . Fracture behavior of triglyceride-based adhesives[J]. Journal of Polymer Science Part B-Polymer Physics, 2004, 42 (18): 3333- 3343. doi: 10.1002/polb.20198
9	WOOL R P . Pressure-Sensitive Adhesives, Elastomers, and Coatings from Plant Oil[M]. Amsterdam: Handbook of Biopolymers and Biodegradable Plastics, 2013: 265- 294.
10	黄旭娟, 刘鹤, 商士斌, 等. 环氧植物油脂的制备及应用研究进展[J]. 生物质化学工程, 2014, 48 (4): 45- 50.
11	AIREY G D , MOHAMMED M H . Rheological properties of polyacrylates used as synthetic road binders[J]. Rheologica Acta, 2008, 47 (7): 751- 763. doi: 10.1007/s00397-007-0250-3
12	HEINRICH L A . Future opportunities for bio-based adhesives: Advantages beyond renewability[J]. Green Chemistry, 2019, 21 (8): 1866- 1888. doi: 10.1039/C8GC03746A
13	ZHANG Y , DUBÉ M A . Green Emulsion Polymerization Technology[M]. Germany: Polymer Reaction Engineering of Dispersed Systems, 2017: 65- 100.
14	BUNKER S , STALLER C , WILLENBACHER N , et al. Miniemulsion polymerization of acrylated methyl oleate for pressure sensitive adhesives[J]. International Journal of Adhesion and Adhesives, 2003, 23 (1): 29- 38. doi: 10.1016/S0143-7496(02)00079-9
15	AHN B K , KRAFT S , SUN X S . Chemical pathways of epoxidized and hydroxylated fatty acid methyl esters and triglycerides with phosphoric acid[J]. Journal of Materials Chemistry, 2011, 21 (26): 9498- 9505. doi: 10.1039/c1jm10921a
16	AHN B K , KRAFT S , WANG D , et al. Thermally stable, transparent, pressure-sensitive adhesives from epoxidized and dihydroxyl soybean oil[J]. Biomacromolecules, 2011, 12 (5): 1839- 1843. doi: 10.1021/bm200188u
17	AHN B K , SUNG J , SUN X S . Phosphate esters functionalized dihydroxyl soybean oil rackifier of pressure-sensitive adhesives[J]. Journal of the American Oil Chemists Society, 2012, 89 (5): 909- 915. doi: 10.1007/s11746-011-1978-6
18	AHN B K , SUNG J , KIM N , et al. UV-curable pressure-sensitive adhesives derived from functionalized soybean oils and rosin ester[J]. Polymer International, 2013, 62 (9): 1293- 1301. doi: 10.1002/pi.4420
19	LI Y H , SUN X S . Di-hydroxylated soybean oil polyols with varied hydroxyl values and their influence on UV-curable pressure-sensitive adhesives[J]. Journal of the American Oil Chemists Society, 2014, 91 (8): 1425- 1432. doi: 10.1007/s11746-014-2474-6
20	LI Y H , CHOU S H , QIAN W T , et al. Optimization of soybean oil based pressure-sensitive adhesives using a full factorial design[J]. Journal of the American Oil Chemists Society, 2017, 94 (5): 713- 721. doi: 10.1007/s11746-017-2966-2
21	SUNG J G, LI Y H, SUN X S. Plasticization effects of dihydroxyl soybean oil improve flexibilities of epoxy-based films for coating applications[J/OL]. Journal of Applied Polymer Science, 2015, 132(14): 41173[2020-10-20]. https://doi.org/10.1002/app.41773.
22	KIM N , LI Y H , SUN X S . Epoxidation of Camelina sativa oil and peel adhesion properties[J]. Industrial Crops and Products, 2015, 64, 1- 8. doi: 10.1016/j.indcrop.2014.10.025
23	WU J, LEI H, LI J, et al. Nucleobase-Tackified renewable plant oil-based supramolecular adhesives with robust properties both under ambient conditions and underwater[J/OL]. Chemical Engineering Journal, 2021, 405: 126976[2020-10-20]. https://doi.org/10.1016/j.cej.2020.126976.
24	MAHMOOD M H , ABDULLAH Z , SAKURAI Y , et al. Effects of monomers on the properties of palm-oil-based radiation curable pressure sensitive adhesives (PSA): A prepolymer method[J]. Radiation Physics and Chemistry, 2001, 60 (1/2): 129- 137.
25	AHN B K , SUNG J , RAHMANI N , et al. UV-curable, high-shear pressure-sensitive adhesives derived from aacrylated epoxidized soybean oil[J]. Journal of Adhesion, 2013, 89 (4): 323- 338. doi: 10.1080/00218464.2013.749102
26	LI Y H , SUN X S . Synthesis and characterization of acrylic polyols and polymers from soybean oils for pressure-sensitive adhesives[J]. RSC Advances, 2015, 5 (55): 44009- 44017. doi: 10.1039/C5RA04399A
27	DAVID S B , SATHIYALEKSHMI K , RAJ G A G . Studies on acrylated epoxydised triglyceride resin-co-butyl methacrylate towards the development of biodegradable pressure sensitive adhesives[J]. Journal of Materials Science-Materials in Medicine, 2009, 20, 61- 70. doi: 10.1007/s10856-008-3482-6
28	LEE T H , PARK Y I , LEE S H , et al. A crack repair patch based on acrylated epoxidized soybean oil[J]. Applied Surface Science, 2019, 476, 276- 282. doi: 10.1016/j.apsusc.2018.12.267
29	LI A L , LI K C . Pressure-sensitive adhesives based on soybean fatty acids[J]. RSC Advances, 2014, 4 (41): 21521- 21530. doi: 10.1039/c4ra03557g
30	MAASSEN W , MEIER M A R , WILLENBACHER N . Unique adhesive properties of pressure sensitive adhesives from plant oils[J]. International Journal of Adhesion and Adhesives, 2016, 64, 65- 71. doi: 10.1016/j.ijadhadh.2015.10.004
31	MAASSEN W , OELMANN S , PETER D , et al. Novel insights into pressure-sensitive adhesives based on plant oils[J]. Macromolecular Chemistry and Physics, 2015, 216 (15): 1609- 1618. doi: 10.1002/macp.201500136
32	WU Y L, LI A L, LI K C. Development and evaluation of pressure sensitive adhesives from a fatty ester[J/OL]. Journal of Applied Polymer Science, 2014, 131(23): 41143[2020-10-20]. https://doi.org/10.1002/app.41143.
33	WU Y L , LI A L , LI K C . Pressure sensitive adhesives based on oleic acid[J]. Journal of the American Oil Chemists Society, 2015, 92 (1): 111- 120. doi: 10.1007/s11746-014-2563-6
34	VENDAMME R , OLAERTS K , GOMES M , et al. Interplay between viscoelastic and chemical tunings in fatty-acid-based polyester adhesives: Engineering biomass toward functionalized step-growth polymers and soft networks[J]. Biomacromolecules, 2012, 13 (6): 1933- 1944. doi: 10.1021/bm300523e
35	VENDAMME R , EEVERS W . Sweet solution for sticky problems: Chemoreological design of self-adhesive gel materials derived from lipid biofeedstocks and adhesion tailoring via incorporation of isosorbide[J]. Macromolecules, 2013, 46 (9): 3395- 3405. doi: 10.1021/ma400203v
36	LI A L , LI K C . Pressure-sensitive adhesives based on epoxidized soybean oil and dicarboxylic acids[J]. ACS Sustainable Chemistry & Engineering, 2014, 2 (8): 2090- 2096.
37	LI Y H , WANG D H , SUN X S . Copolymers from epoxidized soybean oil and lactic acid oligomers for pressure-sensitive adhesives[J]. RSC Advances, 2015, 5 (35): 27256- 27265. doi: 10.1039/C5RA02075A
38	LI Y H , SUN X S . Polyols from epoxidized soybean oil and alpha hydroxyl acids and their adhesion properties from UV polymerization[J]. International Journal of Adhesion and Adhesives, 2015, 63, 1- 8. doi: 10.1016/j.ijadhadh.2015.07.013
39	TORRON S , HULT D , PETTERSSON T , et al. Tailoring soft polymer networks based on sugars and fatty acids toward pressure sensitive adhesive applications[J]. ACS Sustainable Chemistry & Engineering, 2017, 5 (3): 2632- 2638.
40	SAWPAN M A. Polyurethanes from vegetable oils and applications: A review[J/OL]. Journal of Polymer Research, 2018, 25(8): 184[2020-10-20]. https://doi.org/10.1007/s10965-018-1573-3.
41	REN Y B , PAN H M , LI L , et al. Synthesis of polyurethane acrylate and application to UV-curable pressure-sensitive adhesive[J]. Designed Monomers and Polymers, 2005, 8 (4): 383- 396. doi: 10.1163/1568555054460060
42	NORHISHAM S M , MAZNEE T I T N , AIN H N , et al. Soft polyurethane elastomers with adhesion properties based on palm olein and palm oil fatty acid methyl ester polyols[J]. International Journal of Adhesion and Adhesives, 2017, 73, 38- 44. doi: 10.1016/j.ijadhadh.2016.10.012
43	汪钟凯, 周江骏, 穆世玲, 等. 植物油脂基热塑性高分子合成与应用研究进展[J]. 林业工程学报, 2020, 5 (4): 1- 11.
44	黄元波, 郑志锋, 焕马, 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 (3): 21- 26.
45	陈洁, 王义刚, 李小英, 等. 橡胶籽油基复合型环保增塑剂用于PVC的研究[J]. 中国塑料, 2015, 29 (9): 78- 84.
46	李科, 陈洁, 黄金瑞, 等. 乌桕籽油制备环氧脂肪酸乙酯及增塑PVC研究[J]. 精细石油化工, 2018, 35 (3): 75- 82. doi: 10.3969/j.issn.1003-9384.2018.03.017
47	LI M , LI S , XIA J , et al. Tung oil based plasticizer and auxiliary stabilizer for poly(vinyl chloride)[J]. Materials & Design, 2017, 122, 366- 375.
48	LI A L , LI K C . Pressure-sensitive adhesives based on tung oil[J]. RCS advances, 2015, 5 (104): 85264- 85271.
49	GALLART-SIRVENT P , LI A L , LI K C , et al. Preparation of pressure-sensitive adhesives from tung oil via Diels-Alder reaction[J]. International Journal of Adhesion and Adhesives, 2017, 78, 67- 73. doi: 10.1016/j.ijadhadh.2017.06.021
50	SOTOODEH-NIA Z, HOHMANN A, BUSS A, et al. Rheological and physical characterization of pressure sensitive adhesives from bio-derived block copolymers[J/OL]. Journal of Applied Polymer Science, 2018, 135(34): 46618[2020-10-20]. https://doi.org/10.1002/app.46618.
51	LEE S Y , GAN S N . The adhesion properties of natural rubber pressure-sensitive adhesives using palm kernel oil-based alkyd resins as a tackifier[J]. Composite Interfaces, 2013, 20 (3): 177- 188. doi: 10.1080/15685543.2013.763515
52	LEE S , LEE K , KIM Y W , et al. Preparation and characterization of a renewable pressure-sensitive adhesive system derived from epsilon-ecalactone, L-lactide, epoxidized soybean oil, and rosin ester[J]. ACS Sustainable Chemistry & Engineering, 2015, 3 (9): 2309- 2320.
53	ZHAO S J , WANG Z , KANG H J , et al. Fully bio-based soybean adhesive in situ cross-linked by interactive network skeleton from plant oil-anchored fiber[J]. Industrial Crops and Products, 2018, 122, 366- 374. doi: 10.1016/j.indcrop.2018.06.013

[1]	李希越, 王洪波, 赵玉晓, 华栋梁, 王宁. 好氧生物预处理时间对玉米秸秆水解酸化的影响[J]. 生物质化学工程, 2022, 56(1): 13-22.
[2]	曾静, 杨红, 刘士清, 尹芳, 张无敌. pH值对苦荞渣厌氧发酵性能的影响[J]. 生物质化学工程, 2021, 55(5): 35-41.
[3]	李冬娜,马晓军. 污泥厌氧发酵产酸机理及应用研究进展[J]. 生物质化学工程, 2020, 54(2): 51-60.
[4]	陈博,黄元波,王培燕,刘守庆,宁德鲁,郑志锋. 载银介孔SBA-15吸附剂的制备及其对脂肪酸甲酯的吸附研究[J]. 生物质化学工程, 2019, 53(3): 1-7.
[5]	王婧, 野村正人, 古研, 毕良武, 赵振东. 香榧种子含油量及脂肪酸组成对比研究[J]. 生物质化学工程, 2018, 52(4): 7-11.
[6]	李梅, 丁呈祥, 陈洁, 诸进华, 汪梅, 夏建陵. 环保型钙锌复合热稳定剂与增塑剂在 PVC中的协效作用研究[J]. 生物质化学工程, 2017, 51(2): 1-7.
[7]	黄旭娟, 刘鹤, 商士斌, 齐帆. 环氧植物油脂的制备及应用研究进展[J]. 生物质化学工程, 2014, 48(4): 45-50.
[8]	傅宇飞, 孙杨, 潘再法, 王丽丽. 越南安息香种子脂肪酸的在线甲基化-GC分析研究[J]. 生物质化学工程, 2014, 48(2): 18-22.
[9]	周建钟;余丽艳;马海杰;柯大伟;郭明. 乳液型竹纤维素-丙烯酸酯压敏胶制备初探[J]. 生物质化学工程, 2012, 46(6): 21-24.
[10]	朱春玲;周卫兵;何祯祥. 杂交楝果实含油量及籽油脂肪酸组成分析[J]. 生物质化学工程, 2012, 46(5): 25-28.
[11]	陈建洪;叶活动;罗丹明;韩小亮;赖凌雁;曹爱玉. 环氧脂肪酸甲酯连续闪蒸脱水脱味精制工艺研究[J]. 生物质化学工程, 2012, 46(5): 33-35.
[12]	李科;蒋剑春;聂小安;李翔宇;张天健;陈洁;吴欢. 管道式连续甲酯化制备生物柴油中试实验[J]. 生物质化学工程, 2011, 45(6): 15-18.
[13]	陈林;张维;刘天中;陈晓琳;王俊峰;高莉丽;彭小伟;陈昱. 两步法催化高酸价微藻油脂制备生物柴油[J]. 生物质化学工程, 2011, 45(3): 1-7.
[14]	聂小安;夏建陵;沈卫锋;陈新华. 环保型钙/锌PVC热稳定剂的发展现状[J]. 生物质化学工程, 2011, 45(1): 41-46.
[15]	原姣姣;王成章;陈虹霞. 近红外光谱技术及其在植物油品质分析中的应用[J]. 生物质化学工程, 2010, 44(6): 59-65.