Synthesis and Optical Properties of Co-Polycarbonate Containing Cardo Structure and Binaphthalene Structure

doi:10.21203/rs.3.rs-4309740/v1

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Synthesis and Optical Properties of Co-Polycarbonate Containing Cardo Structure and Binaphthalene Structure

https://doi.org/10.21203/rs.3.rs-4309740/v1

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published 03 Sep, 2024

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In this paper, molten transesterification was used with diphenyl carbonate (DPC), 9,9'-bis[6-(2-hydroxyethoxy)naphthyl]fluorene (BNEF), 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene (BHEBN) were used as the polymeric monomers to prepare a series of co-polycarbonates with different molar feeding ratios. It is found that when the molar ratio of BHEBN and BNEF is 6:4, the copolymer has more comprehensive properties. The Mn of the copolymer is 23000 Mn, the Mw is 40700, and the PDI is 1.77. The glass transition temperature is 147.6℃, the initial thermal decomposition temperature (T_d,5%) is 338.9℃, the refractive index is 1.6753, the Abbe number is 18.7, and the light transmittance is 86.23%.

Co-polycarbonates

Optical properties

Refractive index

As the mainstay of optical materials, optical resin plays a very important role in our work and life. Optical resin can also be called optical plastic, it is a kind of polymer material with high transparency. It has the advantages of light weight, low price, strong impact resistance, easy processing and forming, and adjustable comprehensive performance[1–5]. Compared with inorganic optical glass, optical plastics have a wide range of applications, such as electronic appliances, aerospace, building materials, integrated photonic, precision components and other fields[6–9]. Optical resins usually include methyl methacrylate (PMMA), polystyrene (PS), polycarbonate (PC), epoxy optical resin, ring sulfur optical resin and polyurethane optical resin. Among these resins, polycarbonate is the optical resin with the best comprehensive properties[10, 11].

Polycarbonate is divided into aliphatic polycarbonate, aliphatic cyclic polycarbonate and aromatic polycarbonate[12–17]. Aliphatic polycarbonate is mainly used as membrane material in optical field due to its poor heat resistance and mechanical strength[18]. Aliphatic cyclic polycarbonate has better heat resistance and mechanical strength, but its optical properties cannot meet the demand of high refractive index[19, 20]. Aromatic polycarbonate usually has high heat resistance and mechanical strength. Aromatic polycarbonate can be widely used as high refraction optical materials[21], because aromatic ring has a large increase in refractive index. Bisphenol A polycarbonate has a refractive index of 1.59[21–23], but it is easy to produce stress birefringence during processing[24]. The birefringence effect affects the optical imaging effect and is not conducive to the application in the field of high precision components[25]. Although the resulting stress birefringence can be overcome by improving the forming process, the refractive index is low and cannot meet the needs of high-end applications. Bisphenol polycarbonate, such as bisphenol F polycarbonate, bisphenol Z polycarbonate, bisphenol S polycarbonate and bisphenol fluorene polycarbonate, has been concerned by scholars.

Among these bisphenol polycarbonates, bisphenol fluorene polycarbonate has a relatively high refractive index. However, the huge Cardo structure brings a large steric hindrance, which makes the phenol hydroxyl of bisphenol fluorene less reactive. Moreover, the glass transition temperature of bisphenol fluorene polycarbonate is much higher than that of bisphenol A polycarbonate, which causes great difficulties in forming and processing. It is mainly used in the field of high heat resistant materials. The best way to activate the hydroxyl group of bisphenol fluorene is to attach the hydroxy-ethoxy group by chemical reaction. Due to the action of ether bond, the glass transition temperature of the prepared diether fluorene polycarbonate is reduced, which can be made into better products. The refractive index of polycarbonate of diether fluorene(BPEF-PC) can reach 1.6390, which is higher than that of polycarbonate of bisphenol A[21, 26].

However, diether fluorene polycarbonate with refractive index of less than 1.64 is limited in some high-end precision components. Polycarbonate with bi-naphthalene structure was prepared by 2,2'-bis(2-hydroxy-ethoxy)-1,1'-binaphthalene. The refractive index of the material can reach 1.6592, but its heat resistance is relatively poor, and unable to be used directly. For reference to the higher refractive index of BPEF homo-polycarbonate with Cardo structure, we consider combining the structure of naphthalene and Cardo in a monomer structure to further improve the refractive index[27]. Therefore, 9,9'-bis[6-(2-hydroxyethoxy)naphthyl]fluorene (BNEF) was selected as the polymerization monomer.

In this paper, a series of co-polycarbonates with different monomer molar ratios were prepared by melting transesterification of 2,2' -bis (2-hydroxy-ethoxyl)-1,1' -dinaphthalene, 9,9'-bis[6-(2-hydroxyethoxy)naphthyl]fluorene and diphenyl carbonate. The structure, thermal and optical properties of the copolymer were characterized and analyzed.

2.1. Material and monomer preparation

Diphenyl carbonate (DPC, 99.5%, Ningbo Zhejiang Iron Wind Chemical Co., LTD), 9,9'-bis[6-(2-hydroxyethoxy)naphthyl]fluorene (BNEF, 98%, Shanghai Maclean Biochemical Technology Co., LTD), 2,2'-dihydroxy-1,1'-binaphthalene (98%, Shanghai Meryl Chemical Technology Co., LTD༉, ethylene carbonate (99%, Shanghai Maclean Biochemical Technology Co., LTD), dichloromethane (analytical grade, Guangdong Guanghua Technology Co., Ltd.), ethanol (analysis pure, Guangdong Guanghua Technology Co., LTD), Tetrahydrofuran (chromatographic purity 99.9%, Chengdu Banuo Technology Co., LTD.), Nano-sized magnesium oxide (MgO, 99.9%, Shanghai MacLean Biochemical Technology Co., LTD). Lithium acetyl acetone (99.9%, Shanghai Maclean Biochemical Technology Co., LTD). All reagents were used as received and were not processed.

The monomer 2,2'-bis(2-hydroxy-ethoxy)-1,1'-binaphthalene (BHEBN) was synthesized from 2,2'-dihydroxy-1,1'-dinaphthalene and ethylene carbonate[28]. The purity of the synthesized monomer was increased to 99.5% by recrystallization, which was used in the synthesis experiment of co-polycarbonates.

2.2. Polycarbonates synthesis

Using DPC, BNEF and BHEBN as raw materials, Co-polycarbonates were synthesized by melt transesterification and polycondensation. Firstly, 0.05mol of DPC, 0.05mol of diol (the total number of moles of BNEF and BHEBN is 0.05mol) and MgO (based on 0.05wt% of DPC) were added to a 100ml three-necked flask equipped with a mechanical stirrer. Then the reaction feedstock was heated to 160°C (oil bath temperature) in N₂ atmosphere. After complete melting, the reaction was heated to 180°C and stirred at a speed of 170rpm under normal pressure for 30 min. Within 90min, the temperature gradually increased to 240°C, and the reaction pressure gradually decreased to less than 1 Torr to ensure the complete removal of phenol. The polycondensation reaction was carried out at 240°C and 1Torr for 25 minutes. At the end of the reaction, the reaction system was restored to normal pressure by introducing N₂ and cooled to room temperature. The resultant polymer was dissolved in 100 mL of methylene chloride. After completely dissolved, it was slowly poured into a beaker containing 200 ml of anhydrous ethanol to precipitate. The products were filtered and washed twice by anhydrous ethanol and then dried in a vacuum oven at 100°C for 24 hours.

2.3. Characterizations

The FT-IR spectra of polycarbonate were obtained by Thermo Fisher Nicolet 670 spectrometer with wave number of 4000 ~ 500 cm^-1 and resolution of 4 cm^-1. The ¹H NMR and ¹³C NMR were performed on the Bruker AVANCE NEO 600 spectrometer at 25°C. Deuterated chloroform was used as solvent and TMS as internal standard. The molecular weight and molecular weight distribution of the polymers were determined by Waters 1515 pump and 2414 double-column refractive index detector (5mm MIX-C300-7.5mm PL gel) at 35°C. Tetrahydrofuran (THF) was used as an eluent at a flow rate of 1 ml/min and calibrated to polystyrene standards. Differential scanning calorimetry (DSC) was performed in nitrogen atmosphere (50 mL/min) with TA DSC 2920 instrument. The test temperature range was 20°C to 220°C, and the temperature change rate was 10°C /min. The thermal stability of the polymer was tested by a thermogravimetric analyzer (NETZSCH TG 209F3). The sample was heated from 30°C to 600°C in nitrogen atmosphere at a flow rate of 20mL/min and a heating rate of 10°C /min. The polymer sample was dissolved in dichloromethane with a mass fraction of 20%. After being completely dissolved, the film sample was coated on a small CNC coating machine (FA-202) to prepare the film sample. The coating machine sets the thickness of the film to 0.300 mm. The optical properties of the thin films were characterized using a light transmitter/fog meter (SGW®-810) and an Abbe refraction meter (WYA (2WAJ)). The refractive index was measured using D-light at room temperature.

3.1. Composition and molecular weight

The co-polycarbonates contain BNEF and BHEBN were synthesized by a two-step (transesterification and polycondensation) one-pot method (Fig. 1). The feeding ratios of BHEBN and BNEF are different, which correspond to PC-X (X is the molar percentage of BNEF), and are listed in Table 1.

Table 1

Composition and molecular weight of polycarbonates (PC-X).
Co-polycarbonates	Composition ([BHEBN]/ [BNEF])		GPC
Co-polycarbonates	Feed	Co-polycarbonates^[a]	Mn/g·mol^− 1	Mw/g·mol^− 1	PDI
PC-0	100/0	-	35000	53000	1.51
PC-20	80/20	86.3/13.7	24600	40500	1.65
PC-40	60/40	63.6/36.4	23000	40700	1.77
PC-60	40/60	48.0/52.0	22000	46300	2.10
PC-80	20/80	27.5/72.5	21600	49800	2.31
PC-100	0/100	-	18600	48900	2.63

[a] Values obtained from ¹H NMR.

With the increase of BNEF content, the molecular weight of copolymer decreases gradually, and the molecular weight distribution (PDI) increases gradually. This may be due to the greater steric hindrance of the chain segment containing BNEF than that of the chain segment containing BHEBN, and the weaker movement of the chain segment, resulting in the more uneven distribution of polymerization products.

The structure of monomer BHEBN and BNEF contains only aromatic ring and methylene. In the ¹H NMR spectrum (Fig. 3) of copolymers, proton peaks overlap and interfere with each other. The monomer composition of co-polycarbonates cannot be obtained directly from nuclear magnetic hydrogen spectrum integration. However, since the amount of aromatic hydrogen of monomer BNEF and BHEBN is different and the amount of methylene hydrogen is the same, the composition ratio of the copolymer can be calculated by the sum of the number of hydrogen protons.

According to the integral value of ¹H NMR spectrum, the molar ratio of BHEBN/BNEF in the final synthesized co-polycarbonates can be calculated by equations (1), (2) and (3). f _BHEBN and f _BNEF represent the molar percentage of BHEBN and BNEF, respectively. I_a is an integral of 3.84ppm to 4.51ppm, and I_b is an integral of 6.83ppm to 7.77ppm. The calculated molar ratios of co-polycarbonates composition are shown in Table 1.

$${\text{f}}_{\text{BHEBN}}\text{=}\frac{5{\text{I}}_{a}-2{\text{I}}_{b}}{2{\text{I}}_{a}}\times 100\% \text{(1)}$$

$${\text{f}}_{\text{BNEF}}\text{=}\frac{2{\text{I}}_{b}-3{\text{I}}_{a}}{2{\text{I}}_{a}}\times 100\% \left(2\right)$$

$$\frac{\text{BHEBN}}{\text{BNEF}}\text{=}\frac{{\text{f}}_{\text{BHEBN}}}{{\text{f}}_{\text{BNEF}}} \text{(}\text{3}\text{)}$$

From Table 1, it is found that the actual content of BNEF in the polycarbonate is lower than the theoretical amount. This may be due to the fact that BNEF monomer has a Cardo structure in addition to the binaphthalene group, and its steric hindrance is larger than that of BHEBN, so the reactivity is relatively low. Monomer BNEF did not fully participate in the polymerization and has a small loss. The change trend of molecular weight also has confirmed that the BNEF reaction activity is relatively low.

3.2. The chemical structure

The infrared spectrum of the prepared polycarbonate is shown in Fig. 2. Although the copolymerization ratio of polymers is different, they have high similarity in the infrared spectrum, as shown in Fig. 2a. This may be due to the fact that monomers BHEBN and BNEF are polyaromatic cyclic compounds, and the content of other groups except aromatic ring groups is very low. The absorption peak at 3050cm^-1 is the result of the C-H stretching vibration of the benzene ring[29]. At the wave number of 2930 cm^-1, the absorption peak is the methylene C-H asymmetric tensile vibration[30], and the absorption peak at 1750cm^-1 is a typical carbonyl (C = O) stretching vibration[31, 32]. In addition to these remarkable characteristic absorption peaks, other absorption peaks are highly similar. The spectrogram of 600 ~ 1800cm^-1 is enlarged (Fig. 2b). It is found that the absorption peak at 1250cm-1 is enhanced with the increase of BNEF content, but there is no absorption peak when BNEF is not contained. This may be the vibration absorption peak of C-C skeleton of quaternary carbon atoms in Cardo structure. At 1595cm^-1, the absorption peak is enhanced gradually with the increase of BNEF content. This may be because the number of aromatic rings of BNEF is more than that of BHEBN. With the increase of BNEF content, the vibration absorption peak of aromatic ring C = C skeleton is enhanced. The changes of these absorption peaks confirm the successful synthesis of copolymers.

¹H NMR characterization is necessary to further confirm the chemical structure of the synthetic polycarbonates. The ¹H NMR spectrum is shown in Fig. 3. Although there is a peak at 5.1 ~ 5.3ppm, the integral result shows that the integral value of this range is too small to be ignored and it is presumed to be an impurity peak. According to the structure of the material, it is speculated that the copolymer has two main proton absorption peaks, one is the methylene proton peak (3.84 ~ 4.51ppm) connected with oxygen[21], the other is the aromatic ring proton peak (6.83 ~ 7.77ppm). The copolymers BHEBN and BNEF both have methylene and aromatic rings attached to oxygen, and have no other characteristic groups. This makes it impossible to obtain the monomer copolymerization ratio directly from the integral of the characteristic proton peaks. But the different total number of hydrogen atoms in the copolymer can confirm the different proportion of the monomer copolymerization, because the number of hydrogen atoms in the monomer is different.

¹³C NMR characterization has been performed to further confirm the structure of the co-polycarbonates. According to the different structural units connected on both sides of the carbonyl carbon, the carbonyl carbon of co-polycarbonate appears in four forms: C₁, C₂, C₃ and C₄, as shown in Fig. 4a. In co-polycarbonate, C₂ and C₃ can be regarded as the same, the chemical environment of co-polycarbonate is relatively complex, so the chemical shift of C₁ and C₄ is slightly offset, C₃ and C₄ appear between the signal peaks of C₁ and C₄[21]. However, it is worth noting that the signal peak at 155.04ppm is not the signal peak of carbonyl carbon, but the carbon signal peak on the naphthalene ring in the BNEF unit.

In Fig. 4b, it is found that the carbon peak (141.1ppm, 140.2ppm, 133.2ppm, 118.9ppm, 106ppm) attributed to BNEF homogeneous polycarbonate also appears in the co-polycarbonates, but disappears in the BHEBN homogeneous polycarbonate without BNEF[32]. The carbon peak (134.1ppm, 124ppm, 116ppm) in the BHEBN homogenous polycarbonate appear simultaneously in the co-polycarbonate[33], but disappear when there is no BHEBN. More importantly, the peak at the chemical shift of 58.5ppm is the sp³ hybridized quaternary carbon atom in the Cardo structure, which occurs in the polycarbonates containing BNEF[34].

The integral data obtained by ¹³C NMR can be combined with equations (4), (5), and (6) to calculate the numerical mean sequence length (L_n) of BHEBN carbonate unit and BNEF carbonate unit in the co-polycarbonate, and the random degree (R) of the co-polycarbonate. The results are listed in Table 2.

$${\text{L}}_{\text{n,BHC}}\text{=}\text{1+}\frac{2{\text{I}}_{BHC}}{{\text{I}}_{BHC\&BNC}} \text{(}\text{4}\text{)}$$

$${\text{L}}_{\text{n,BNC}}\text{=}\text{1+}\frac{2{\text{I}}_{BNC}}{{\text{I}}_{BHC\&BNC}} \left(5\right)$$

$$\text{R}\text{=}\frac{\text{1}}{{\text{L}}_{\text{n,BHC}}}+\frac{\text{1}}{{\text{L}}_{\text{n,BNC}}} \text{(}\text{6}\text{)}$$

Where, I_BHC, I_BNC and I_BHC&BNC correspond to the area integral values of C₄, C₁ and C₂&C₃ signal peaks in Fig. 4a; L_n,BHC and L_n,BNC are the numerical mean sequence lengths of BHEBN carbonate unit and BNEF carbonate unit. R is the random degree of the copolymer.

Table 2

Composition and Microstructure of polycarbonates (PC-X).
Co-polycarbonates	Composition ([BHEBN]/ [BNEF])		Microstructure
Co-polycarbonates	Feed	Co-polycarbonates^[a]	L_n,BHC	L_n,BNC	R
PC-0	100/0	-	-	-	-
PC-20	80/20	83.2/16.8	4.31	3.15	0.55
PC-40	60/40	66.1/33.9	2.31	4.13	0.68
PC-60	40/60	46.8/53.2	1.33	5.65	0.93
PC-80	20/80	23.7/76.3	1.12	12.76	0.97
PC-100	0/100	-	-	-	-

[a] Values obtained from ¹³C NMR.

When R = 0, it is a simple physical blending of homopolymer. When 0 < R < 1, it is block copolymer; When R = 1, it is random copolymer; When R = 2, it is an alternate copolymer. The co-polycarbonate synthesized in this paper is a block copolymer with R values ranging from 0.55 to 0.97. With the increase of BNEF content, the copolymer tends to be random copolymer.

3.3. Thermal properties

The synthesized polycarbonates were characterized by DSC (Fig. 5) to study the thermal properties of the co-polycarbonates. It can be seen that there is no melt crystallization peak in the cooling scan and no melt crystallization peak in the second heating scan. Moreover, all polycarbonates have only one glass transition temperature, so all the synthetic polycarbonates are amorphous.

Table 3

DSC and TGA results of polycarbonates (PC-X).
Co-polycarbonate	DSC (Second heating scan)	TGA
Co-polycarbonate	T_g (°C)	T_D,5%(°C)	T_DM(°C)
PC-0	118.0	325.7	378.6
PC-20	131.9	330.1	385.1/430.1
PC-40	147.6	338.9	391.4/431.1
PC-60	163.1	341.6	392.8/445.2
PC-80	180.9	359.8	401.7/445.6
PC-100	200.0	373.2	444.9

T_{D, 5%}: The decomposition temperature at 5% weight lost.

T_DM: The decomposition temperature at maximum weight loss rate.

The glass transition temperature results of the synthesized polycarbonates are listed in Table 3. The glass transition temperature (Tg) of BHEBN homologous polycarbonate (PC-0) is 118℃, while the Tg of BNEF homologous polycarbonate (PC-100) is 200℃. The glass transition temperature of copolymer is between 118℃ and 200℃, and increases with the increase of BNEF content. In the copolymerization process, although there is a loss of BNEF, the actual measured glass transition temperature is in good agreement with the results obtained from the Fox equation (Fig. 6). When the content of BNEF is higher than 40%, the glass transition temperature is higher than that of BPA-PC[35], which can be applied to more high-temperature environmental fields.

The thermal stability of the synthesized polycarbonate was analyzed by TGA (Fig. 7). The initial thermal decomposition temperature (T_D,5%) is positively correlated with the content of BNEF in the polycarbonates. This is because the BNEF polycarbonate chain segment with naphthalene ring and Cardo structure has higher rigidity and heat resistance.It is interesting to note that the DTG curves of the polycarbonate show double valleys, which means that there are two maximum thermal decomposition rates. However, both BHEBN homogenous polycarbonate (PC-0) and BNEF homogenous polycarbonate (PC-100) have only one maximum thermal decomposition rate. Co-polycarbonates have only one glass transition temperature. This indicates that homo-polycarbonates are degraded in one step, while co-polycarbonates are degraded in two steps[14]. In spite of this, the variation trend of decomposition temperature at maximum thermal decomposition rate (T_DM) of polycarbonate is positively correlated with the content of BNEF.

3.4. Optical properties

The sample was characterized by optical properties test, and the characterization results were shown in Table 4. It can be seen from the data in Table 4 that BNEF homo-polycarbonate (PC-100) has a refractive index of up to 1.6813. By comparing the structures of BNEF and BHEBN, it can be concluded that the Cardo structure with multi-aromatic rings greatly improves the refractive index, which is consistent with the literature reports. Compared with the 1.6390 refractive index of BPEF homologous polycarbonate, the high refractive index of BNEF homologous polycarbonate is attributed to the naphthalene ring group.

Table 4

Optical properties of polycarbonates (PC-X).
Polymer	Refractive index	Abbe number	Transmittance
PC-0	1.6592	20.8	88.25
PC-20	1.6710	18.7	87.54
PC-40	1.6753	18.5	87.23
PC-60	1.6780	18.4	87.07
PC-80	1.6809	18.3	87.80
PC-100	1.6813	18.0	87.91

The refractive index of polycarbonate increased with the increase of BNEF content, but the glass transition temperature also increased gradually. The increasing rate of the glass transition temperature is much higher than that of the initial thermal decomposition temperature, which will make it more difficult to process the material. BNEF mainly increases the refractive index, and the addition of BHEBN can adjust the glass transition temperature of the copolymer. The Abbe number is calculated from the refractive index at three specific wavelengths. There is a negative correlation between Abbe number and refractive index, but it is mainly determined by the structure of the material. Transmittance is the primary index of optical materials, which is mainly affected by material structure and sample preparation technology.

In the field of optical polycarbonate, high refractive index has always been the research target of scholars. In this paper, the prepared polycarbonates have a higher refractive index, and have the advantages of heat resistance and transparency of carbonate, which may promote the wide application of the co-polycarbonates. A single material with excellent properties is often difficult to apply in isolation. Therefore, it is necessary to improve the comprehensive properties of materials through copolymerization or blending to meet the application requirements. The introduction of BHEBN in BNEF polycarbonate can reduce the refractive index, but greatly reduce the glass transition temperature, thus making the processing and molding of the material easier. When the content of BHEBN is 60%, the content of BNEF is 40%, the copolymerization of polycarbonate (PC-40) has better comprehensive performance. The refractive index was 1.6753, the Abbe number was 18.7, the light transmission was 87.23%, the Tg was 147.6℃ and the initial thermal decomposition temperature was 338.9℃.

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Funding:

This work was supported by the Key Deployment Project of the Chinese Academy of Sciences [grant numbers ZDRW-CN-2022-1].

Data availability

The data used to support the findings of this study are included within the article.

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Synthesis and Optical Properties of Co-Polycarbonate Containing Cardo Structure and Binaphthalene Structure

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Abstract

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1. Introduction

2. Experimental

2.1. Material and monomer preparation

2.2. Polycarbonates synthesis

2.3. Characterizations

3. Results and discussion

3.1. Composition and molecular weight

3.2. The chemical structure

3.3. Thermal properties

3.4. Optical properties

4. Conclusion

Declarations

Funding:

Data availability

References

Status:

Journal Publication

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