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Biobased Anethole/Polymethacrylate Cross-linked Materials with Good Transparency and High thermostability Fengkai He, Kaikai Jin, Jing Sun, and Qiang Fang ACS Sustainable Chem. Eng., Just Accepted Manuscript • DOI: 10.1021/ acssuschemeng.7b03899 • Publication Date (Web): 12 Jan 2018 Downloaded from http://pubs.acs.org on January 12, 2018

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ACS Sustainable Chemistry & Engineering

Biobased Anethole/Polyacrylate Cross-linked Materials with Good Transparency and High thermostability Fengkai He, Kaikai Jin, Jing Sun* and Qiang Fang*

Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, PR China.

* E-mail: [email protected].

KEYWORDS:

Biomass,

anethole,

thermosetting

polymers,

thermostability,

transparent materials

ABSTRACT: A series of new thermo-crosslinkable polymers with both excellent transparency and thermostability derived from a biorenewable plant oil (anethole) are reported here. By using the plant oil as the feedstock, a new monomer (anethole-based methacrylate) containing propenyl and acryloyl functional units is successfully synthesized via a simple two-step reaction route. Copolymerizing the monomer with methyl methacrylate (MA) in the presence of radical initiator gives the copolymers, which are post-polymerized at high temperature to form the polymers, exhibiting the thermostability and the transmittance depending on the content of the anethole-based methacrylate. With the increasing of the content of the anethole-based methacrylate, 1

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the thermostability of the crosslinked polymers raises while the transparency decreases. The best results are obtained when the molar ratio between methyl acrylate and anethole-based methacrylate is 2:1. In that case, the cured polymer shows a glass transition temperature (Tg) of 148 °C and a coefficient of thermal expansion (CTE) of 152.58 ppm/°C, as well as high transparency with the transmittance of more than 92% from 450 to 1100 nm. These data exhibit that the new methacrylate-containing polymers derivated from a biorenewable can be used as the high performance optical materials with both good transparency and high thermostability.

INTRODUCTION Optically transparent inorganic materials such as glass and ceramic have been widely used in industrial areas for many years. For example, they have been utilized as lens for the various optical devices, as display panels in TV and cell-phones and as windshields for cars. In recent years, they have been used as fiber optics in hospitals and the telecommunication fields.[1-5] However, these materials usually are brittle and have high density (>2.2). Therefore, organic transparent materials have attracted much attention due to their low density, good impact resistance, and excellent processability.[6-10] Among various organic transparent materials, poly(methyl methacrylate) and polycarbonate are

particularly

gathering interest because of

their excellent transparency and processability.[11-12] Nevertheless, these organic transparent materials exhibit low thermostability. Moreover, the use of some polycarbonates containing bisphenol-A units is limited because bisphenol-A is 2


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harmful to human reproductive system.[13-16] Hence, exploring the new organic materials with both good transparency and high thermostability are necessary. It is noted that poly(methyl acrylate) (PMA) also shows good transparency and good film-forming ability. However, in many cases, PMA is only used as coating because of its low glass-transition temperature (Tg) and poor solvent-resistance.[17] On the basis of low price of PMA, developing the PMA-based polymers with both good transparency and high thermostability is desirable. In principle, introducing the crosslinkable groups into the backbone of polymers could enhance the thermostability of the polymers. This suggests that attaching the crosslinkable groups to PMA can increase the thermostability of the polymer because high crosslinking density could endow the polymer with the high thermostability. It was found that that a plant oil (anethole) with an active propenyl group can be copolymerize with maleic anhydride.[18-21] In our previous reports, we found that anethole could be converted into high performance polymers via chemical methods.[22-23] During our recent research, We also found that the methoxy group at the benzene ring of anethole can be efficiently converted to -OH group in the presence of sodium lauryl mercaptan.[24] These results motivate us to design a new methacrylate, which contains both propenyl and acryloyl functional units. It is expected that the double bond at acrylate group can react with the propenyl group in anethole to form the crosslinked network in the presence of radical initiator. Our purpose is mainly to develop the application of the renewable biomass. The chemical structure of the new anethole-based methacrylate is shown in Scheme 1. In the 3



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presence of radical initiator, the new methyl acrylate (M2) forms an infusible and insoluble resin, while the homopolymer of methyl acrylate (MA) shows low Tg and solubility in the common solvents. This result indicates that the propenyl unit has reacted with the double bond in MA. We further investigate the properties of the copolymers between M2 and methyl acrylate in different molar ratio. The results exhibit that the introduction of anethole into the skeleton of PMA can efficiently increase the glass-transition temperature of the polymer without decreasing the transparency. Thus, anethole, a biorenewable aromatic compound, could be used as a starting material for production of the high performance materials with both high transparency and good thermostability. Here, we report the details.

EXPERIMENTAL SECTION Materials. Anethole was purchased from Nanjing Chemlin Chemical Industry Co., Ltd., 1-dodecanethiol was purchased from Shanghai Aladdin Biochemical Technology Co., Ltd., methyl acrylate, acrylyl chloride and azobisisobutyronitrile (AIBN) were purchased from TCI company. Methyl acrylate was purified by distillation. Azobisisobutyronitrile was purified by recrystallization from ethanol. N-methyl-pyrrolidinone

(NMP),

dichloromethane,

sodium

hydroxide,

and

triethylamine were purchased from Sinopharm Chemical Reagent Co., Ltd., and used as received unless otherwise stated. Instruments. 1H NMR and

13

C NMR spectra were recorded on a JEOL ECZ400

NMR spectrometer at room temperature using TMS as an internal standard and CDCl3 as a solvent. High-resolution mass spectra (HRMS) were recorded on a DARTSVP 4


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(IonSense Inc.). Elemental analysis was carried out on an Elementar vario EL III system. Differential scanning calorimetry (DSC) was run on a TA Instrument DSC Q200 at a heating rate of 10 °C/min under nitrogen flow. FT-IR spectra were measured on a Nicolet spectrometer with KBr pellets. Thermogravitric analysis (TGA) was performed on a TG 209F1 apparatus with a heating rate of 10 °C/min in N2 atmosphere. UV-vis-NIR spectra were obtained on a Varian Cary 5000 instrument, and the thickness of the samples was about 2.5 mm. Dynamic mechanical analysis (DMA) and thermomechanical analysis (TMA) were performed with a heating rate of 3 °C min-1 in air on the Mettler Toledo DMA/SDTA861e and TMA/SDTS841e instruments, respectively. Shore and Rockwell hardness tests were carried out at room temperature on a LX-A hardness tester and a HRS-150 hardness tester, respectively.

Synthesis of M1. This compound was prepared according to a route previously reported.[24] 1H NMR (400 MHz, CDCl3, δ): 7.20 (d, 2H), 6.75 (d, 2H), 6.32 (d, 1H), 6.07 (m, 1H), 1.85 (d, 3H).

Synthesis of M2. To a stirring mixture of M1 (10.00 g, 74.53 mmol), acrylyl chloride (10.12 g, 111.79 mmol) and CH2Cl2 (60 mL) was added dropwise trimethylamine (11.31 g, 111.79 mmol) at 0 °C during a period of 1 h. Then the solution was stirred at the room temperature for an additional 0.5 h. The mixture was quenched with water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The obtained crude product was purified by chromatography using a mixture of petroleum ether and ethyl acetate

5



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as the eluent (100:1, v/v). M2 was prepared thus in a yield of 89.9% as a colourless transparent liquid. 1H NMR (400 MHz, CDCl3, δ): 7.31 (d, 2H), 7.04 (d, 2H), 6.60 (d, 1H), 6.39∼3.15 (m, 3H), 5.96 (d, 1H), 1.85 (d, 3H). 13C NMR (126 MHz, CDCl3, δ): 164.55, 149.26, 135.77, 132.43, 127.94, 126.67, 125.97, 121.43, 18.43. HR-MS (m/z): calcd for C12H12O2 [M]+ 188.0837, found 188.0832. Anal. Calcd for C12H12O2: C, 76.57; H, 6.43. Found: C, 76.84; H, 6.43.

Synthesis

of

poly(MA-co-M2)m/n.

The

random

cross-linked

copolymers

(poly(MA-co-M2)m/n) were prepared by a radical polymerization route. In poly(MA-co-M2)m/n, m/n represented the mole ratio between MA and M2. All the copolymers were synthesized according to the same procedure as that for the preparation of poly(MA-co-M2)8/1. Here, taking as an example, the synthesis of poly(MA-co-M2)8/1 was described as below. A glass tube having a mixture of MA (731.8 mg, 8.50 mmol), M2 (200.0 mg, 1.06 mmol), and AIBN (1.6 mg, 9.56 µmol) was heated to 60 °C and kept at this temperature for 3 h until the liquid became a transparent solid. The tube was then kept at 90 °C, 120 °C, 150 °C, and 220 °C for 5 h, respectively. Thus, the fully cross-linked polymer was prepared, which could not swell in common solvents. RESULTS AND DISCUSSION As described in Scheme 1, using a new route we reported recently,[24] 4-hydroxypropenylbenzene (M1) is prepared in a near quantitative yield starting from anethole. Based on M1, the new methyl acrylate, M2, is synthesized in a yield of 90%. The chemical structure of M2 is confirmed by 1H NMR,

13

C NMR, mass spectra 6


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(HRMS), and FT-IR analysis. Figure S1 depicts the 1H NMR spectrum of M2. It is seen that the characteristic proton peaks attributed to the H at the C=C bond are observed at 5.96~6.60 ppm. This 1H NMR spectrum also confirms the presence of the benzene ring and methyl group, showing at 7.31, 7.04 and 1.85 ppm, respectively. 13C NMR spectrum of M2 is given in Figure S2. As can be seen from Figure S2, the characteristic signal of C=O group appears at 164.55 ppm. FT-IR spectrum of M2 indicates the characteristic peaks of C=O, -C=C-CH3 and -CH=CH2 groups at 1737, 1656 and 1630 cm-1, respectively. All the data are consistent with the proposed chemical structure of M2.

Scheme 1. Procedure for the synthesis of the new monomer and polymers.

The polymerization reaction of M2 in the presence of AIBN, a radical initiator, was monitored by DSC, and the results are shown in Figure 1. As exhibited in Figure 1, the radical polymerization starts about 85 °C and gives a peak exothermic temperature of about 124 °C. The second scan shows no exothermic peaks, indicating that these M2 has completely transferred into the crosslinked networks. FT-IR spectrum of M2 7



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after heating at 220 °C exhibits that the characteristic signal attributed to the group -CH=CH2 of acrylate at 1630 cm-1 and the representative peak of -C=C-CH3 of anethole at 1650 cm-1 completely disappears, suggesting that the copolymerization between -C=C-CH3 group and -CH=CH2 group has occurred in M2.

Figure 1. DSC traces of M2 in the presence of AIBN at a heating rate 10 °C min-1 in N2 .

Figure 2. FT-IR spectra of M2 and its homopolymer.

We further investigate the copolymerization reaction of M2 with MA in different molar ratio. Table 1 summarizes the results of DSC traces. As shown in Table 1, the peak exothermic temperature of the co-monomers raises with the increasing of the 8


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molar ratio between M2 and MA. The heat enthalpy of the co-monomers also exhibits an increasing tendency with the largening of the molar ratio between M2 and MA, suggesting that the amount of M2 in the co-monomer has a slight effect on the copolymerization reaction of MA with M2.

Table 1. DSC data of the copolymers. Samples

Tonset (°C)

Tpeak (°C)

∆H (KJ/mol)

PMA

97

116

72.8

poly(MA-co-M2)8/1

90

118

74.5

poly(MA-co-M2)4/1

88

119

76.0

poly(MA-co-M2)2/1

81

120

82.0

PM2

91

124

88.9

We further investigate the thermostability of the copolymers between M2 and MA in different molar ratio. Figure 3 depicts the TGA results. As can be seen from Figure 3, PMA offers the lowest Td5 of about 362 °C and the lowest char yield of 1.74% at 1000 °C, whereas PM2 shows the highest Td5 of about 362 °C and the highest char yield of 14.56%. For the copolymers of MA with M2, they exhibit increasing Td5 and char yield with the raising of the content of M2 in the copolymer. This result indicates that copolymerizing M2 with methyl acrylate can form a thermo-crosslinking network, which may offer good thermostability to the polymers.

9



Page 10 of 20

Figure 3. TGA curves of polymers in N2 with a heating rate of 10 ºC min-1. The glass transition temperatures (Tg) of copolymers were measured by DMA. Figure 4 shows the DMA curves of the copolymers, running the tests from 25 to 350 °C. It is seen from Figure 4, the glass transition temperatures of the copolymers increase with the amount of M2 raise in the copolymers. The values of storage modulus show the same tendency as that of the glass transition temperatures. For example, PMA is a thermoplastic polymer that shows lowest storage modulus of near 0 MPa. However, poly(MA-co-M2)2/1 possesses higher storage modulus and Tg. For PM2, it indicates storage modulus of reaching to 3 GPa even at 350 °C. All these results suggest that the introduction of M2 leads to a highly crosslinked network, which enhances the thermostability of the copolymer.

10


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Figure 4. DMA curves of the polymers.

It is well known that PMA shows good optical transparency. Therefore, in order to investigate optical properties of the copolymers, UV-vis-NIR spectra of the copolymers were carried out. As depicted in Figure 5, the copolymer films exhibit the transmittance of more than 90% at a range of wavelengths from 450 to 1100 nm. Interestingly, poly(MA-co-M2)2/1 shows a high transmittance of 92% even at the wavelength of 450 nm (Table 2). Besides, this copolymer also exhibits high thermostability with Td5 of 398 °C at N2 and Tg of 148 °C. These results indicate that introducing M2 into PMA not only improves the thermostability of the polymer but also maintains the high transparency of the polymer.

Table 2. Transmittance of the polymer sheets with average thickness of 2.5 mm at 450 nm. Samples

PMA

poly(MA-co-M2)8/1

poly(MA-co-M2)4/1

poly(MA-co-M2)2/1

PM2

T%

95

92

90

92

85

11



Page 12 of 20

Figure 5. UV-vis-NIR spectra of the polymer sheets with average thickness of 2.5 mm.

Dimensional stability is an important parameter for the evaluation of the properties of materials. The sample’s dimension change is usually evaluated by the static thermal mechanical analysis (TMA). The sample’s coefficient of thermal expansion (CTE) can be calculated according to equation 1:

α(T ) =

1 dL(T )

L dT

(1)

Where α(T) is temperature-dependent coefficient thermal expansion (CTE), L is the length of sample before heating, and L(T) is the length of sample at a temperature T. As shown in Figure 6, with the rising of content of M2 in the copolymers, the copolymers exhibit lower coefficient thermal expansion (CTE). For instance, poly(MA-co-M2)8/1 shows a CTE of 200.65 ppm/°C , whereas poly(MA-co-M2)2/1 offers the value of 152.58 ppm/°C. In particular, PM2 exhibits a CTE of 72.28 ppm/°C, which is comparable to some commercial materials, such as epoxy resins.[25] 12


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Figure 6. TMA curves of polymers.

Hardness test is usually used to evaluate the mechanical properties. At room temperature, PMA is similar to rubber because of low Tg. Therefore, the hardness of PMA was tested by the Shore hardness tester, and the other copolymers were tested by the Rockwell hardness tester. As depicted in Table S1, PMA shows a hardness of 54, and the other copolymers show hardness varying from 114 to 123 with the increasing content of M2, which are better than common optical materials, such as PMMA[26] and PC[27]. These data imply that M2 can endow the materials with good wear-resisting ability. Such good properties exhibit that the copolymers may have potential application as new type of optical materials.

CONCLUSIONS In summary, we have successfully synthesized a series of thermosetting polymers based on a biorenewable anethole. The polymers show the thermostability and the transmittance depending on the content of the anethole in the polymers. With the increasing of the content of anethole unit in the polymers, the thermostability of the 13



Page 14 of 20

polymers raises. The transparency of the polymers also changes with the increasing of the content of anethole unit. The best results are obtained when the molar ratio between methyl acrylate and anethole-based methacrylate is 2:1. Hardness tests show that the polymers exhibit higher hardness than poly (methyl acrylate). These data suggest that the biorenewable anethole could be utilized as a modifier for improvement of the thermostability and wear-resistance of some optical materials without decreasing their transparency.

ASSOCIATED CONTENT

Supporting Information

This Supporting Information is available free of charge via the Internet at http://pubs.acs.org.

AUTHOR INFORMATION

Corresponding Author * E-mail: [email protected].

Notes The authors declare no competing financial interest. ACKNOWLEDGMENTS

Financial supports from Ministry of Science and Technology of China (2015CB931900) and the Natural Science Foundation of China (NSFC No. 21574146, 14


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No. 21504103 and No.21774142) and the Science and Technology Commission of Shanghai

Municipality

(15ZR1449200

and

16JC1403800)

are

gratefully

acknowledged. The authors are also grateful to the Strategic Priority Research Program of the Chinese Academy of Sciences (Grant XDB 20020000).

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For Table of Contents Use Only

Toc Graphic

Synopsis: A series of high performance thermosetting polymers derived from plant oil (anethole) have been developed, which show excellent transparency and high thermal stability.

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