丙烯海松酸聚乙二醇酯的合成及聚集行为

doi:10.3969/j.issn.1673-5854.2019.04.003

Abstract

Abstract:

Acrylpimaric acid was obtained with rosin and acrylic acid as raw materials and characterized by gas chromatography-mass spectrometry technology(GC-MS). Acrylicpimaric acid polyglycol ester was synthesized by steglich esterification method under mild conditions with acrylicpimaric acid and polyglycol(PEG 2000) as monomers. Structure and properties of the substance were studied by infrared, gel permeation chromatography(GPC), and thermogravimetric(TG). The average-number molecular weight of the substance was 4 700 with the polydispersity index of 1.2. The decomposition temperature of acrylicpimaric acid and polyglycol ester was 308-410℃. The critical micelle concentration(CMC) of acrylicpimaric acid polyglycol ester in water was 1 g/L by surface tension and steady-state fluorescence method. The aggregation behaviors of acrylicpimaric acid polyglycol ester in water were investigated by rayleigh light scattering(RLS), dynamic light scattering(DLS) and scanning electron microscopy(SEM) techniques. The results indicated that the stabilized micelle of 1 g/L acrylicpimaric acid polyglycol ester aggregated as the temperature was higher than the aggragation temperature(74℃) and the aggregation temperature decreased from 74℃ to 65℃ as the solution concentration increased from 1 g/L to 1.5 g/L. And as the temperature of acrylicpimaric acid polyglycol ester solution increased from 25℃ to 85℃, the average diameter of hydrate particle(D_h) increased from 295 nm to 1 056 nm.

Key words: acrylicpimaric acid polyglycol ester, steglich esterification, amphiphilic, aggregation behavior

CLC Number:

TQ35
TQ9

Yanzhi ZHAO,Juying ZHOU,Fangkai DU,Haitang XU,Jianfang LU,Xia ZHANG. Synthesis and Aggregation Behavior of Acrylicpimaric Acid Polyglycol Ester[J]. Biomass Chemical Engineering, 2019, 53(4): 19-25.

Figures/Tables 10

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References 18

1	SENGUPTA D , PIKE R W . Chemicals from biomass[J]. Science, 2007, 318 (5854): 1250- 1251. doi: 10.1126/science.1146356
2	CORMA A , IBORRA S , VELTY A . Chemical routes for the transformation of biomass into chemicals[J]. Chemical Reviews, 2007, 38 (36): 2411- 2502.
3	GUNERA F S , YAGCI Y , ERCIYES A T . Polymers from triglyceride oils[J]. Progress in Polymer Science, 2006, 31 (7): 633- 670. doi: 10.1016/j.progpolymsci.2006.07.001
4	GANDINI A . Polymers from renewable resources:A challenge for the future of macromolecular materials[J]. Macromolecules, 2008, 41 (24): 37- 59.
5	MEIER M , METZERB J O , SUHUBERT U S . Plant oil renewable resources as green alternatives in polymer science[J]. Chemical Society Reviews, 2007, 39 (5): 1788- 1802.
6	BLANAZS A , ARNES S P , RYAN A J . Self-assembled block copolymer aggregates:From micelles to vesicles and their biological applications[J]. Macromolecules Rapid Communications, 2009, 30 (4/5): 267- 277.
7	HOARE T , KOHANE D S . Hydrogels in drug delivery:Progress and challenges[J]. Polymer, 2008, 49 (8): 1993- 2007. doi: 10.1016/j.polymer.2008.01.027
8	TORCHILIN V P . Micellar nanocarriers:Pharmaceutical perspectives[J]. Pharmaceutical Research, 2007, 24 (1): 1- 16.
9	SUTTON D , NASONGKLA N , BLANCO E , et al. Functionalized micellar systems for cancer targeted drug delivery[J]. Pharmaceutical Research, 2007, 24 (6): 1029- 1046. doi: 10.1007/s11095-006-9223-y
10	OSTUNI E , CHAPMAN R G , HOLMLIN R E , et al. A survey of structure property relationships of surfaces that resist the adsorption of protein[J]. Langmuir, 2001, 17 (18): 5601- 5620.
11	TSITSILIANIS C , PAPANAGOPOULOS D , LUTZ P . Amphiphilic heteroarm star copolymers of polystyrene and poly(ethylene oxide)[J]. Polymer, 1995, 36 (19): 3745- 3752. doi: 10.1016/0032-3861(95)93779-L
12	JIANG X , SMITH Ⅲ M R , BAKER G L . Water-soluble thermo responsive polylactides[J]. Macromolecules, 2008, 41 (2): 318- 324. doi: 10.1021/ma070775t
13	MORHADE D M , NANDE V S , BARABDE U V , et al. Study of biodegradation and biocompatibility of PEGylated rosin derivatives[J]. Journal of Bioactive and Compatible Polymers, 2017, 32, 628- 640. doi: 10.1177/0883911517705404
14	ATTA A M , El-MAHFY G A , ALLOHEDAN H A , et al. Application of nonionic surfactants based on rosin as corrosion inhibitor for tubing steel during acidization of petroleum oil and gas wells[J]. International Journal of Electrochemical Science, 2015, 10, 8- 21.
15	RAY G B , CHAKRABORT I , MOULIK S P . Pyrene absorption can be a convenient method for probing critical micellar concentration(CMC) and indexing micellar polarity[J]. Journal of Colloid and Interface Science, 2006, 294, 248- 254. doi: 10.1016/j.jcis.2005.07.006
16	AGUIAR J , CARPENA P , MOLINA-BOLIVAR J A , et al. On the determination of the critical micelle concentration by the pyrene 1:3 ratio method[J]. Journal of Colloid and Interface Science, 2003, 258, 116- 122. doi: 10.1016/S0021-9797(02)00082-6
17	PASTERNACK R F , BUSTMANTE C , COLLINGS P J , et al. Porphyrin assemblies on DNA as studied by a resonance light-scattering technique[J]. Journal of America Chemistry Society, 1993, 115, 5393- 5399. doi: 10.1021/ja00066a006
18	ZHANG W Z , CHEN X D , LUO W , et al. Study of phase separation of poly(vinyl methyl ether) aqueous solutions with rayleigh scattering technique[J]. Macromolecules, 2009, 42 (5): 1720- 1725. doi: 10.1021/ma802671a

保留时间/min retention time	化合物名称 compound name	相对分子质量 relative molecular weight	匹配度 matching degree
9.21	海松酸pimaric acid	316	98%
10.20	长叶松酸palustric acid	316	96%
10.75	脱氢枞酸dehydroabietic acid	316	95%
11.55	枞酸abietic acid	316	98%
12.42	新枞酸neoabieticacid	316	99%
16.42	丙烯海松酸(间位)acrylicpimaric acid(meta-position)	402	96%
18.49	丙烯海松酸(对位)acrylicpimaric acid(para-position)	402	97%

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Synthesis and Aggregation Behavior of Acrylicpimaric Acid Polyglycol Ester

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