JPH0586797B2 - - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to phospholipid compounds, and particularly to phosphatidylcholine type phospholipid compounds (glycerophosphocholine compounds) having a polymerizable group. [Prior Art] Currently, various attempts are being made to encapsulate medicinal substances, enzymes, etc. into minute capsules and provide them as pharmaceuticals. The early method of such microencapsulation was the encapsulation of polymer compounds by emulsification method (Japanese Patent Publication No. 45-2757 and Patent Publication No. 17950-1983).
Encapsulation accompanied by the formation of polymers (polyamide, etc.) through interfacial polycondensation reactions
7395 and Special Publication No. 53-7396). However, these methods require large particle sizes (several μm).
It has the disadvantage that it can only form capsules (~1000 μm), and there are problems in using the obtained capsules, for example, as pharmaceuticals. By the way, the main purpose of encapsulating pharmaceutical substances and enzymes in microcapsules is to retain the activity of pharmaceutical substances and enzymes that are unstable in vivo for a long period of time, and to maintain their effects for a long period of time. As a technology that satisfies these conditions to a considerable degree, we utilize the fact that various phospholipids, which are components of biological membranes, form microscopic spherical aggregates (liposomes, particle size 0.03 to 10 μm) in water. Recently, a technique has been reported in which a phospholipid compound having a polymerizable group is synthesized, and the resulting liposome is polymerized while being kept intact to obtain stable microcapsules. For example, SL Regen (SL
Journal of the American Chemical Society (Regen) et al.
American Chemical Society), 104, 791-795
(1982) (hereinafter referred to as literature), Angewante Chemie International Edition by H-H. Hub et al.
Edition) English Edition, 19, 938-940 (1980) (hereinafter referred to as Reference ()), and Angewante Chemie International Edition by Akimoto et al.
Edition) English version 20, 90-91 (1981) (hereinafter referred to as literature). The synthetic phospholipid compounds described in these documents form liposomes (or vehicles) in water. In order to microencapsulate this liposome as it is, the polymerizable groups in each compound (i.e., methacrylic group in the compound in literature (), diacetylene group in the compound in literature (), and butadiene group in the compound in literature ()) are required. group) needs to be polymerized. In order to initiate the polymerization of the compound described in the literature (), an appropriate polymerization initiator (for example, an azo initiator such as azobisisobutyronitrile, an organic peroxide initiator such as benzoyl peroxide, Polymerization can also be carried out by adding an initiator (such as potassium sulfate) or by irradiation with ultraviolet light, but in this case high energy is required and light with a shorter wavelength is required. It is said that the compounds described in documents () and () are relatively easily polymerized by irradiation with ultraviolet light. [Problems to be solved by the invention] In any case, there is an increasing demand for the development of polymerizable phospholipid compounds that more easily polymerize when irradiated with light and form microcapsules through the polymerization. has been done. An object of the present invention is to provide a novel polymerizable phospholipid compound that has a highly photopolymerizable styrene core and forms microcapsules through polymerization. [Means for Solving the Problems] According to the present invention, the general formula: (where n is a positive integer from 1 to 10, and l
is a positive integer from 12 to 20). The phospholipid compound of the present invention represented by the general formula (A) can be synthesized according to the reaction route () or reaction route () shown below. Reaction route () [C] [C] [C] [C] [C] [C] [C] [C] carbodiimide,
DMAPy is 4-(N,N-dimethylamino)pyridine, and AcOH is acetic acid. In addition, compound (C) was manufactured by H.I.B.I.L.
Eibl) et al. method (Jus.Lieb.Ann.
Chem.), 709 226-230).
2-O-benzyl-rac-glycerol (2-benzyloxy-1,3-propanediol (compound It can be synthesized by condensing (B)) with a suitable fatty acid chloride or fatty acid anhydride. In reaction route (), first, compound (C) and β, β, β-trichloroethyl carbonate (TCEC) are combined. in the presence of a suitable dehydrochlorination agent (e.g., pyridine, etc.) in an anhydrous solvent (e.g., methylene chloride, etc.) under ice cooling or at room temperature for 5 to 24 hours to obtain 1-acyl-2-O-benzyl-rac. -Glycero-3-(β,β,β-trichloroethyl)carbonate (compound (D)) is synthesized. Compound (C) and
The charging molar ratio with TCEC ((TCEO)/(C)) is 1
-3, preferably 1-1.2. Next, compound (D) is reduced with hydrogen using palladium on carbon as a catalyst (for example, using 95% butanone as a solvent), and 1-acyl-rac-glycero-3
-(β,β,β-trichloroethyl)carbonate (compound (E)) is synthesized. A 1-acyl compound is produced by reacting compound (E) with ω-(p-vinylphenoxy)alkanoic anhydride in an anhydrous solvent (e.g., methylene chloride, etc.) at room temperature for 10 to 48 hours in the presence of DMAPy. -2-O-
{ω-(p-vinylphenoxy)alkanoyl}-
rac-glycero-3-(β,β,β-trichloroethyl)carbonate (compound (F)) is obtained. Next, the trichloroethyl group of compound (F) is removed using activated zinc in a mixed solvent of acetic acid/diethyl ether, for example, to form 1-acyl-2-{ω-(p
-vinylphenoxy)alkanoyl}-rac-glycerol (compound (G)) is obtained. Finally, compound (G) was converted into 2-chloro-2-oxo-
1,3,2-Dioxaphosphorane (RS Edmundson, Chemistry and Industry, London);
1828 (1962)) in an anhydrous solvent (e.g., benzene, etc.) at room temperature for 3 to 24 hours in the presence of a suitable dehydrochlorination agent (e.g., triethylamine, etc.), and then reacted with excess dry trimethylamine for 50 to 24 hours. 1 at 80℃
By reacting for ~10 hours, the desired 1-acyl-2-{ω-(p-vinylphenoxy)alkanoyl}-rac-glycero-3-phosphocholine (compound (A)) can be synthesized. In reaction route (), first, compound (C)
and 2-chloro-2-oxo-1,3,2-dioxaphosphorane (molar ratio (oxolane)/(C) is 1
-2, preferably 1-1.2), in the presence of a suitable dehydrochlorination agent (e.g., triethylamine, etc.) in an anhydrous solvent (e.g., benzene, etc.) at room temperature.
After reacting for 50 h with excess triethylamine
1-acyl-2- by reacting at ~80℃ for 1-10 hours.
O-benzyl-rac-glycero-3-phosphocholine (compound (H)) is synthesized. Next, compound (H) was reduced with hydrogen in the presence of palladium on carbon to obtain 1-acyl-rac-glycero-3-
Synthesize phosphocholine (compound (J)). Finally, compound (J) and ω-(p-vinylphenoxy)alkanoic anhydride are reacted in the presence of DMAPy in an anhydrous solvent (e.g., methylene chloride, etc.) at room temperature for 10 to 48 hours. Compound (A) can be synthesized. As the activation reagent for ω-(p-vinylphenoxy)alkanoic acid, common reagents such as dicyclohexylcarbodiimide, chloroethyl formate, and carbonylimidazole can be used. Furthermore, among the compounds represented by formula (A), the fatty acids that are raw materials for synthesizing those with l of 12, 14, or 16 are conveniently available as commercially available products at low cost. By the way, ω-(p
-vinylphenoxy)alkanoic acid can be synthesized, for example, as follows. That is, an ω-halogenated fatty acid ester represented by the formula (L) (where n is as described above, R is an alkyl group such as a methyl group or ethyl group or a benzyl group, and X is a bromine or iodine atom) and p-hydroxystyrene in a suitable anhydrous solvent (e.g., acetone) in the presence of 1 to 20 equivalent moles of a suitable anhydrous base for dehydrohalogenation (e.g., anhydrous sodium carbonate, anhydrous potassium carbonate), Either by heating to 80°C and reacting for 5 to 24 hours, or by previously reacting p-hydroxystyrene with, for example, 1 to 1.2 moles of sodium hydride in a suitable anhydrous solvent (N,N-dimethylformamide, etc.). By reacting this with a compound of the general formula (L) at 0°C to 30°C for 3 to 24 hours, the ether represented by the general formula Obtain the compound. After reacting this compound in a suitable solvent (e.g., dioxane-methanol-water mixture) containing 5 to 20 equivalent moles of a base such as sodium hydroxide or potassium hydroxide at 0 to 30°C for 3 to 24 hours, A compound represented by formula (K) is obtained by acidifying by adding an excess of acid such as concentrated hydrochloric acid. The phosphatidylcholine-type phospholipid compounds of the present invention can be used using common methods for obtaining ribosomes from natural phospholipids (e.g., Biosimica e Biosimica acta by D. Papahadjopoulos et al. Biochimia
et Biophysia Acta), 135, 639-652 (1967)), ribosomes with a particle size of 0.02 to 1 μm can be formed in water by treating one or more of them. In forming this ribosome, in addition to the phospholipid compound of the present invention, a non-polymerizable phospholipid having ribosome-forming ability (e.g., egg yolk lecithin, dipalmitoyl lecithin, dimyristoyl lecithin, distearoyl lecithin, etc.) and/or cholesterol are used. may also be used. In addition, in formula (A), the larger the values of n and l, the easier it is to form liposomes. By irradiating the resulting liposome-dispersed aqueous solution with full ultraviolet light or ultraviolet monochromatic light (e.g., 240 nm, 310 nm) in an inert gas atmosphere (argon, nitrogen, etc.), the polymerization reaction proceeds quickly and stabilizes the solution. Microcapsules are formed. During this polymerization, there is no need to add additives such as a polymerization initiator. The microcapsules obtained from the phosphatidylcholine type phospholipid compound of the present invention can be encapsulated with a medicinal substance, enzyme, etc. (by polymerization in a physiologically acceptable aqueous solution containing the medicinal substance, enzyme, etc.). It can be expected to be used as a medicine or as a reagent for various tests such as clinical tests. In addition, by encapsulating photographic photosensitizers, dyes, etc., it becomes a material for obtaining clearer photographs and printed images. It can also be used as a surface modification material for photoresist materials and various materials. Examples of this invention will be described below. Synthesis Example 1 Synthesis of 11-(p-vinylphenoxy)undecanoic acid In a four-neck flask equipped with a calcium chloride drying tube, an isobaric addition funnel, and a thermometer, 7.2 grams (180 mmol) of oily sodium hydride (60%) were added. )
After washing with approximately 50 ml of n-hexane three times, dry N,N-dimethylformamide (DMF)
300 ml was added and stirred under ice cooling. A solution of 19 g (158 mmol) of p-hydroxystyrene dissolved in 300 ml of dry DMF was slowly added dropwise to this over 25 minutes, and the mixture was stirred for 10 minutes. Then, 11-bromodecanoic acid methyl ester
A solution of 48.6 grams (174 mmol) dissolved in 160 milliliters of dry DMF was slowly added dropwise over 30 minutes, the ice bath was removed, and the mixture was stirred at room temperature for 1.5 hours.
11 milliliters of anhydrous methanol was added. The reaction mixture was filtered, the filtrate was dried under reduced pressure using an evaporator, and the residue was purified using a silica gel column (elution solvent: benzene/petroleum ether = 1/1). The target portion was collected, and the solvent was distilled off. did.
The residue was recrystallized from methanol to obtain the desired 11-(p-
Vinylphenoxy) undecanoic acid methyl ester
27.9 grams (55% yield) were obtained. The analytical values for this compound are as follows. Thin layer chromatography (TLC) (silica gel, benzene): Rf = 0.6 (UV, I ₂ ) Mass spectrum: 318 (M ⁺ ) Infrared absorption (IR) spectrum (NaCl plate) (cm
^-1 ): 1730 (ν _c=p ester), 1620 (ν _c=c vinyl),
1600, 1505 (ν _c=c phenyl) Elemental analysis value (wt%) C 75.20 (75.43) H 9.58 (9.49) Values in parentheses are calculated values for C ₂₀ H ₃₀ O ₃ . Melting point: 61-61.5°C 27.7 grams of 11-(p-vinylphenoxy)undecanoic acid methyl ester thus obtained was dissolved in 845 milliliters of dioxane, and then 420 milliliters of methanol and 420 milliliters of 2N sodium hydroxide were dissolved therein.
After 15 hours of stirring at room temperature in the dark, the solvent was distilled off. After adding 1 liter of water and 84.5 ml of concentrated hydrochloric acid to the residue, the mixture was stirred for 1 hour. The precipitate was collected by filtration, thoroughly washed with water, and then dried under reduced pressure. This was recrystallized from 2 liters of n-hexane to obtain the desired 11-(p-vinylphenoxy).
24.4 grams (90% yield) of undecanoic acid were obtained. The analysis results of this compound are described below. Melting point: 94-95℃ Elemental analysis (wt%): C 74.86 (74.96) H 9.62 (9.27) Values in parentheses are calculated values for C ₁₉ H ₂₈ O ₃ Mass spectrum: 304 (M ⁺ ) IR spectrum ( KBr pellet): 1700 cm ^-1 (ν _c=p carboxylic acid) ¹³ C-NMR spectrum (in CDCl ₃ , TMS standard): [Table] Synthesis example 2 Synthesis of 2-O-benzyl-rac-glycerol 1,3- 2-O-benzyl-1 synthesized from benzylidene glycerol and benzyl chloride,
3-Benzylidene glycerol (H. Ible et al., Justis Liebitz, Annalen,
Hydrolyzing Dell Chemistry, 709 , 226-230 (1967) (D. A. West et al., Journal of the American Chemical Society,
74, 4466-4467 (1952)). Yield 60
%. Boiling point: 160-165℃/4Torr (literature value: 185-187
℃/10Torr). Melting point 36-38°C (literature value: 38.5-40°C). Mass spectrum ₍ MS): 182 (M ⁺ ) (molecular weight _{of C10H14O3} 182.219). ^1H -NHR spectrum ( _CDCl3 , tetramethylsilane (TMS)) δ (ppm): 2.29 (2H, t, -OH),
3.74 (4H, m, −CH ₂ − | CH −CH ₂ −), 4.64 (2H, s, [formula]), 7.35 (5H, s, [formula]). ¹³ C-NMR spectrum (CDCl ₃ , TMS): [Table] Synthesis example 3 1-octadecyl-2-O-benzyl-rac-
Synthesis of glycerol In a flask with a calcium chloride drying tube, add 15.6 g (54.8 mmol) of stearic acid to dry benzene.
500ml was added and stirred. In this, oxalic acid chloride
After adding 9.4 ml (110 mmol) and 0.05 ml of N,N-dimethylformamide and stirring at room temperature for 3 hours, the mixture was evaporated and the residue was dried under reduced pressure. This residue was dissolved in 50 ml of dry methylene chloride, and this solution was slowly added dropwise into a solution of 7 g of 2-O-benzylglycerol dissolved in 100 ml of dry methylene chloride. After stirring overnight, 0.3 liters of chloroform was added, and the mixture was washed successively with 2N hydrochloric acid, saturated brine, 5% sodium carbonate and saturated brine, and dehydrated over sodium sulfate. After filtering this, the filtrate was subjected to evaporation, and the residue was purified using a silica gel column (petroleum ether/ether = 9/1 ~
6/4). Objective part (Rf = silica gel TLC
0.25 (petroleum ether/ether = 6/4), UV)
was collected, subjected to evaporation, and then dried under reduced pressure.
In this way, 12.78 g of the oily target compound was obtained (yield 52%). Melting point: 30-31℃. MS: 448 (M ⁺ ) (molecular weight _{of C28H48O4} 448.685) _. ¹³ C-NMR spectrum (CDCl ₃ , TMS): [Table] Compounds with l = 14 and l = 18 in general formula (C) were obtained by using palmitic acid and arachidic acid in place of stearic acid, respectively. . Synthesis example 4 1-octadecanoyl-2-O-benzyl-
Synthesis of rac-glycerol-3-trichloroethyl carbonate In a four-necked flask with a calcium chloride drying tube and an isobaric dropping funnel, 1-octadecanoyl-2-
4.2 g (9.4 mmol) of O-benzyl-rac-glycerol was dissolved in 50 ml of dry methylene chloride, and 0.81 ml (10 mmol) of dry pyridine was added thereto, followed by cooling on ice. While stirring, 2.1 g (99 mmol) of triethyl chloroformate and 15 ml of dry methylene chloride were slowly added dropwise thereto, followed by stirring overnight.
After adding 150 ml of diethyl ether thereto, the mixture was washed with dilute hydrochloric acid, water and 5% sodium carbonate, and the organic layer was collected and dehydrated over sodium sulfate. After filtration, the filtrate was evaporated and the residue was dried under reduced pressure to obtain 5.7 g (yield 97%) of the target compound. MS: 622 (M ⁺ ) ( _molecular weight _{of C31H49O6Cl3} 624.083 ₎ . Elemental analysis values (wt%): C 60.00 (59.66) H 8.15 (7.91) (Calculated values in parentheses, same below) ¹³ C-NMR spectrum (CDCl ₃ , TMS): [Table] Synthesis example 5 1-octadeca Synthesis of noyl-2-[11-(p-vinylphenoxy)undecanoyl]-rac-glycerol 1-octadecanoyl-2-O-benzyl-
2.0 g (3.2 mmol) of rac-glycero-3-trichloroethyl carbonate was dissolved in 80 ml of 95% butanone. To this was added 0.4 g of 10% Pd-C/40 ml of 95% butanone, stirred at room temperature for 3 hours under a hydrogen atmosphere of 1 atm, and then filtered. subjecting the filtrate to evaporation;
After drying under reduced pressure, it was freeze-dried from benzene. This was dissolved in 40 ml of dry methylene chloride. 11-(p-vinylphenoxy)undecanoic acid
1.17 g (3.8 mmol) in 80 ml of dry methylene chloride
After dissolving in the solution, 0.79 g (3.8 mmol) of DCC was added, stirred at room temperature in the dark for 3 hours, and filtered. This filtrate was added to the above methylene chloride solution. After adding 0.8 mmol of N,N-dimethylaminopyridine to this mixture, the mixture was allowed to react at room temperature in the dark for one day. After the reaction, 0.4 liter of diethyl ether was added, and the mixture was washed successively with dilute hydrochloric acid, water, 5% sodium carbonate and water, and dehydrated with sodium sulfate. After filtration, the filtrate was evaporated and the residue was dried under reduced pressure.
Dissolve this in 15ml of acetic acid/15ml of ethyl ether,
It was treated with 3.0 g of activated zinc for 30 minutes. Add diethyl ether/chloroform (4/1) to this mixture.
After adding 400 ml, it was filtered, and the filtrate was washed with water and then dehydrated with sodium sulfate. After filtration, the filtrate was evaporated and the residue was purified using a silica gel column (benzene/
diethyl ether = 9/1) and target compound 0.76
g (yield 37%) was obtained. MS: 645 (M+1) (molecular weight _{of C40H68O6 644.973} ). Elemental analysis values (wt%): C 74.08 (74.49) H 10.55 (10.63) ¹³ C-NMR spectrum (CDCl ₃ , TMS): [Table] Example 1 (Reaction route ()) 1-Octadecanoyl-2- Synthesis of [11-(p-vinylphenoxy)undecanoyl]-rac-glycero-3-phosphocholine In a flask with a calcium chloride drying tube, 1-octadecanoyl-2-[11-(p-vinylphenoxy)undecanoyl-rac-glycerol 0.6g
After dissolving (0.93 mmol) in 20 ml of dry benzene, 20 mg of N,N-dimethylaminopyridine and 0.17 ml of dry triethylamine were added. 2-chloro-2-oxo-1, 2-chloro-2-oxo-1,
After adding 0.14 g (1.2 mmol) of 3,2-dioxaphosphocholine, the mixture was stirred overnight at room temperature in the dark. The filtered solution was subjected to evaporation, and the residue was dried under reduced pressure. After dissolving this in 30 ml of dry acetonitrile, 20 ml of dry trimethylamine was added and reacted in a pressure bottle at 160°C for 6 hours. The reaction mixture was evaporated and the residue was purified using a silica gel column (chloroform/methanol/water = 65/25/4).
did. The target part (the part having the same Rf value as egg yolk phosphatidylcholine (EYPC) by TLC) was collected, subjected to evaporation, and the residue was freeze-dried from benzene. In this way, 0.45 g of the target compound (yield
60%). FABMS: 810 (M+1) (molecular weight of C ₄₅ H ₈₀ N ₁ O ₉ P ₁
810.103 Elemental analysis value: N1.75 (1.73) ¹³ C-NMR spectrum (CDCl ₃ , TMS): [Table] Synthesis example 6 1-octadecanoyl-2-O-benzyl-
Synthesis of rac-glycero-3-phosphocholine In a four-necked flask with a calcium chloride drying tube and an isobaric dropping funnel, 1-octadecanoyl-2-
After dissolving 14.8 g (33 mmol) of O-benzyl-rac-glycerol in 100 ml of dry benzene, N,
50 mg of N-dimethylaminopyridine and 5.3 ml (40 mmol) of dry triethylamine were added. A solution of 4.5 g (40 mmol) of 2-chloro-2-oxo-1,3,2-dioxaphosphorane in 30 ml of dry benzene was slowly added dropwise to the mixture while stirring, and the mixture was stirred overnight at room temperature. After filtration, the filtrate was evaporated and the residue was dried under reduced pressure. After dissolving this in 0.1 liter of dry acetonitrile, 0.1 liter of dry triethylamine was added, and in a pressure bottle,
The reaction was carried out at 60°C for 6 hours. The reaction mixture was evaporated and the residue was purified on a silica gel column (chloroform/methanol/water = 64/25/4). In this way, 13.9 g (yield 72%) of the target compound was obtained. TLC (silica gel; chloroform/methanol/water = 65/25/4): Rf = 0.2 (UV) (Reference: EYPC Rf = 0.3) FABMS: 614 (M + 1) (C ₃₃ H ₆₀ N ₁ O ₇ P ₁ molecular weight
613.814) Elemental analysis value (wt%): N2.22 (2.28) ¹³ C-NMR spectrum (CDCl ₃ , TMS): [Table] Of the compounds of general formula (H), l = 14 and l = 18 The compound was also synthesized in the same manner. Synthesis example 7 1-octadecanoyl-rac-glycero-3-
Synthesis of phosphocholine 1-octadecanoyl-2-O-benzyl-
3.0 g (4.9 mmol) of rac-glycero-3-phosphocholine was mixed with butanone/methanol/water = 8/2/
After dissolving in 50ml of 0.5 mixed solvent, 10% Pd-C0.6
g/10 ml of butanone was added. The mixture was stirred at room temperature for 2 days under 1 atmosphere of hydrogen and filtered. After subjecting the filtrate to evaporation, the residue was purified using a silica gel column (chloroform/methanol/water =
65/25/4). The target part (the part showing the same Rf value as lysolecithin in TLC) was collected, subjected to evaporation, and then freeze-dried from a benzene/methanol mixed solvent. In this way, 2.0 g of the target compound (yield
78%). Elemental analysis value (wt%): N2.54 (2.67) FABMS: 524 (M+1) (molecular weight of C ₂₆ H ₅₄ N ₁ O ₇ P ₁
523.690) ¹³ C-NMR spectrum (CDCl ₃ , TMS) δ
(ppm): [Table] Of the compounds of general formula (J), compounds with l=14 and l=18 were also synthesized in the same manner. Example 2 Synthesis of 1-hexadecanoyl-2-[11-(p-vinylphenoxy)undecanoyl-rac-glycero-3-phosphocholine 11-(p
-vinylphenoxy)undecanoic acid 0.49g (1.6
After dissolving DCC (1.6 mmol) in 50 ml of dry methylene chloride, 0.34 g (1.6 mmol) of DCC was added, and at room temperature,
The mixture was stirred in the dark for 3 hours. Filter this, and the filtrate is
0.40 g (0.81 mmol) of 1-hexadecanoyl-rac-glycero-3-phosphocholine and 10 mg of N,N-dimethylaminopyridine were dissolved in dry methylene chloride.
After adding the solution to 50 ml, the mixture was stirred overnight at room temperature in the dark. After adding 100 ml of chloroform to this, it was washed with water, and the organic layer was dehydrated with sodium sulfate. After filtration, the filtrate was evaporated and the residue was purified using a silica gel column (chloroform/methanol/
Wednesday = 65/25/4). Objective part (silica gel
Collect the parts that show the same Rf value as EYPC by TLC,
This was subjected to evaporation and the residue was lyophilized from benzene/methanol. Thus, 0.33g of the target compound
(Yield 52% was obtained. FABMS: 783 (M+2) (molecular weight of C ₄₃ H ₇₆ N ₁ O ₉ P ₁
782.049) ¹³ C-NMR spectrum (CDCl ₃ , TMS): Consistent with the compound of Example 1. Elemental analysis value (wt%): N2.07 (1.79). [Effects of the Invention] As described above, the present invention provides a novel phospholipid compound that can form microcapsules through polymerization. The compound of this invention is
Since the styrene cores are bonded through ether bonds, it has the advantage of being less likely to decompose even when irradiated with a relatively large amount of light, which facilitates the photopolymerization operation.

Claims (1)

[Claims] 1 General formula [Chemical formula] (where n is a positive integer from 1 to 10, and l
is a positive integer from 12 to 20).