JPH0489821A - Molded item of hydrogenated norbornene resin - Google Patents

Abstract

PURPOSE:To improve the surface of a molded item of a hydrogenated polymer obtd. from a ring-opening polymer of a cyclic norbornene compd. and thereby increase the resistance to scratch, water, moisture, and heat of the item by dry coating the surface with an inorg. compd. CONSTITUTION:The surface of a molded item of a hydrogenated polymer obtd. from a ring-opening of a monomer component comprising at least one compd. of formula I [wherein A and B are each H or a 1-10C hydrocarbon group; X and Y are each H, a 1-10C hydrocarbon group, a group of formula I, II, III, IV, or V, or a group of formula VI or VII each comprising X and Y; (m) is 0 or 1; R<1>, R<2>, R<3>, and R<4> are each a 1-10C hydrocarbon group; Z is H or a hydrocarbon group; W is a group of formula VIII (wherein R<5> is a 1-10C hydrocarbon group; D is OCOR<5>, or OR<5>; and (p) is 0-3); and (n) is 0-10] and a monomer copolymerizable therewith (e.g. cyclopentene) is dry coated with an inorg. compd. (e.g. SiO2, Al2O3). The resulting coated item has an improved resistance to scratch, water, moisture, and heat and is useful in many applications including an optical lens and an automotive windshield.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a hydrogenated norbornene resin molded article dry-coated with an inorganic compound.
This invention relates to a molded article of hydrogenated norbornene resin that is dry-coated with an inorganic compound that has excellent scratch resistance, heat resistance, and optical properties.

[Prior Art] Hydrogenated ring-opening polymers of compounds having norbornene rings have recently been proposed as various (co)polymers due to their usefulness as transparent resins with excellent optical properties and heat resistance. (Japanese Unexamined Patent Publication No. 1-240517, etc.).

That is, norbornene ring compounds such as norbornene, dicyclopentadiene, tetracyclo2.5 7.
10 [One or more monomers selected from 4,4,0,1,1-3-dodecene or its derivatives, W, Mo, Re,
A hydrogenated polymer obtained by further hydrogenating a polymer obtained by ring-opening polymerization using a polymerization catalyst selected from transition metal compounds such as Ti or a catalyst combining the transition metal and an organometallic compound such as LllMg, A1, Sn, etc. In addition to having much higher heat resistance than conventional methacrylic resin,
It has excellent properties such as low water absorption and light weight, not only for optical applications such as lenses and optical discs, but also for general molded products.

However, the surface hardness of these resins was not sufficient for some uses compared to conventional acrylic resins. In addition, the thermal stability (coloring at high temperatures) of the hydrogenated ring-opening polymer of the norbornene ring compound mentioned above can be significantly improved by increasing the hydrogenation rate or adding a specific stabilizer. However, this was not always sufficient depending on the conditions, and there remained considerable cost problems in increasing the hydrogenation rate.

[Invention or Problem to be Solved] As described above, the present invention improves the surface hardness of a molded product of a hydrogenated polymer of a ring-opening polymer of a norbornene ring compound (hereinafter referred to as hydrogenated norbornene resin). The goal is to provide a method for Another object of the present invention is to improve the thermal stability of hydrogenated norbornene resin moldings.

[Means for solving the problem] That is, the present invention provides a monomer comprising at least one compound represented by the following general formula (I), or this monomer and a copolymerizable monomer copolymerizable with the monomer. To provide a molded body of a hydrogenated norbornene resin, which is obtained by dry-coating the surface of a molded body of a hydrogenated polymer obtained by ring-opening polymerization of a ring-opening polymer with an inorganic compound. It is something.

In the present invention, the hydrogenated norbornene resin is produced by ring-opening (co)polymerizing at least one compound represented by the following general formula (I) alone or with other copolymerizable monomers in the presence of a metathesis catalyst. Then, the obtained (co)polymer is subjected to a hydrogenation reaction in the presence of a monohydrogenation catalyst to hydrogenate 90% or more of the non-aromatic double bonds present in the molecule.

In the general formula (I), A and B are hydrogen atoms or hydrocarbon groups having 1 to 10 carbon atoms, X and Y are hydrogen atoms, hydrocarbon groups having 1 to 10 carbon atoms, -(CH)COOR1- (C) (2)
. oc.

n R' -(CH) CN, -(CH2)nn C0NR2R"-(CH2'), C00Z, -(C
H) 0COZ, -(CH2). OZ, -(CH2)
Indicates nW or composed of X and Y, and m is O or 1. In addition, RlR, R and R4 are hydrocarbon groups having 1 to 20 carbon atoms, 2 is a hydrocarbon group or a hydrogen atom, 5 W is SIRD (R5 is 1 to 11 carbon atoms) 3
-p is a hydrocarbon group of O, D is a halogen atom, -〇COR or -OR'' p is an integer of O~3), n is O~10
indicates an integer. ] In the compound represented by the above general formula (I), in order to improve the heat resistance of the molded article, at least one of the substituents X and Y may be a group other than a hydrogen atom and a hydrocarbon group. preferable. moreover,
One of the substituents X and Y has the formula -(CH) C00RI
A carboxylic acid varnish n thyl group represented by is preferable in that it does not change during the hydrogenation step during resin production, and it is preferable that the other one is a hydrogen atom or a hydrocarbon group. Also, the formula -(CH)C
Among the carboxylic n-acid ester groups represented by 0OR', those with a smaller n are preferable because the heat resistance of the hydrogenated norbornene resin increases. Particularly in the formula -(CH2)nCOOR, it is preferable that n=0. It is preferred in terms of synthesis and stability of the hydrogenated norbornene resin. R1 has 1 or more carbon atoms
20 aliphatic, alicyclic, or aromatic hydrocarbon groups, but the larger the number of carbon atoms, the lower the water absorption of the resulting polymer, so it is preferable that the polymer has a larger number of carbon atoms. Therefore, in order to make the most of the characteristics of this resin, it is necessary to use a chain hydrocarbon group with 1 to 4 carbon atoms or a chain hydrocarbon group with 5 carbon atoms.
The above alicyclic hydrocarbon groups, phenyl groups, and substituted phenyl groups are preferred, and more preferably 8-methyl-8-methoxycarbonyltetracyclo[4,4,0,1,1"10]
-3-do2.5 decene is particularly preferred.

The ring-opening polymer can also be a copolymer by using two or more compounds represented by the general formula (I).

For example, 8-methyl-8-methoxycarbonylte2.5
7.10 Tracyclo[4,4,0,1,1]-3-dodecene and 5
-Methyl-5-methoxycarbonylbicyclo[2,2,
1] -2-heptene can also be copolymerized. This combination shows that 5-methyl-5-methoxycarbonylbicyclo[2,2°1]-2-heptene is 8-methyl-8
-methoxycarbonyltetracyclo[4,4,0,12
It is particularly preferred because it can be obtained as an intermediate in the production of 1° co-3-dodecene.

In addition, other monomers copolymerized with compound (I) include:
Cyclopentene, cyclohexene, cycloheptene, cyclooctene, pentacyclo[6°3.6 2,
7 9.135.1.1. 0. 0
Mention may be made of cycloalkanes such as co-11-pentadecene and their alkyl substituted products.

When obtaining a copolymer with a compound represented by general formula (I) using a copolymerizable monomer, if the amount of the compound represented by general formula (I) is small, the final resin obtained will have high heat resistance. Therefore, the proportion of the monomer of general formula (I) needs to be 50 mol% or more, preferably 70% or more, and more preferably 80% or more.

Further, the polymerization of the compound represented by the general formula (I) can be carried out using polybutadiene, polyisoprene, styrene-butadiene copolymer, ethylene-propylene non-conjugated diene copolymer,
It can also be carried out in the presence of an unsaturated hydrocarbon polymer containing a carbon-carbon double bond in its main chain, such as polynorbornene, and in this case, the obtained hydrogenated norbornene resin has particularly high impact resistance. Among these unsaturated hydrocarbon polymers, butadiene-styrene copolymers and isoprene-styrene copolymers are preferred because they facilitate the production of transparent molded bodies. In this case, the copolymer of diene and styrene may be a random copolymer or a block copolymer.

When polymerizing in the presence of an unsaturated hydrocarbon polymer, the polymer has a molecular weight of 1 to 50 with respect to the compound represented by general formula (I).
% by weight, preferably 3-40% by weight, more preferably 5% by weight
~30% by weight is used.

The metathesis polymerization catalyst used for ring-opening polymerization is (A)W
At least one compound selected from STi, Mo and Re compounds, and (B) periodic table IA, mA, IIB
, HA, TVA, or a compound of a group IVB element having at least one element-carbon bond or element-hydrogen bond, and an additive that increases the catalytic activity. (C)
may be added.

(A) Suitable W, Ti SMo or Re as a component
Typical examples of compounds include WCl6, TiC1, Mo
Examples include C1 and Re0C13.

Specific examples of component (B) include n-BuLil
(C2H5)3A1, (C2H5)2A ICI,
Examples include LiH.

As representative examples of component (C), alcohols, aldehydes, ketones, amines, etc. can be suitably used.

The usage ratio of component (A) and component (B) is 1:1 to 1:50 in terms of metal atomic ratio (A):(B), preferably 1
:2 to 1:30.

The usage ratio of component (C) and component (A) is (C) in molar ratio.
): (A) is used in a range of 0.005+1 to 10:1, preferably 0.05:1 to 2:1.

The molecular weight of the polymer can also be adjusted by the polymerization temperature, type of catalyst, and type of solvent, but more preferably ethylene,
It may be possible to adjust the amount by coexisting α-olefins such as propylene, 1-butene, 1-pentene, 1-hexene, 1-octene, etc. in the reaction system and changing the amount thereof. The polymer used in the present invention has a molecular weight of η1□h and 0.2
~5.0 is preferred.

The hydrogenation reaction of the (co)polymer obtained by the above metathesis ring-opening polymerization is carried out by a conventional method. As the catalyst used in this hydrogenation reaction, those used in ordinary hydrogenation reactions of olefinic compounds can be used.

For example, examples of the heterogeneous catalyst include solid catalysts in which a catalyst material such as palladium, platinum, ruthenium, rhodium, or nickel is supported on a carrier such as carbon, silica, alumina, or titania.

Particularly, a catalyst in which palladium is supported on a silica/magnesia carrier is preferable from the viewpoint of activity and life.

In addition, homogeneous catalysts include organic solvent-soluble nickel, cobalt, titanium, and vanadium compounds such as nickel naphthenate, titanocene dichloride, and cobalt acetylacetonate, and organic aluminum compounds such as triethylaluminum, triisobutylaluminum, and diethylaluminum monochloride. , or a catalyst in combination with organolithium such as butyllithium can be used.

Further, noble metal complex catalysts such as chlorotris(triphenylphosphine)rhodium and dichlorotris(triphenylphosphine)ruthenium can also be used.

The hydrogenation reaction can be carried out in a hydrogen gas atmosphere of normal pressure to 300 atm, preferably 3 to 150 atm, at a temperature of 0 to 200°C, preferably 20 to 180°C. Hydrogenation rate is 60
Measured by MHzNMR, δ=4.5-6. 90% calculated from the reduction of peaks in the 0 ppm range due to hydrogenation reaction
It is necessary that it is at least 95%, more preferably at least 98%. When the hydrogenation rate is less than 90%,
This is not preferable since it may cause problems with the stability of the hydrogenated norbornene resin.

In the present application, the gel content of the hydrogenated norbornene resin used is 1% by weight or less, preferably 0.1% by weight or less, and the water content is 300 ppm or less, preferably 100% by weight or less.
ppm or less, the halogen content is less than 50 ppm, preferably less than 20 ppm.

In the present application, other thermoplastic resins may be added to the hydrogenated norbornene resin as necessary. Other thermoplastic resins have a glass transition temperature of 25°
It is a polymer of C or higher, and includes amorphous polymers, crystalline polymers, liquid crystal polymers, and the like. Specific examples of the thermoplastic resin include styrene resin, vinyl chloride resin, acrylic resin, polyphenylene ether resin, polyarylene sulfite resin, polycarbonate resin,
Examples include polyester resin, polyamide resin, polyethersulfone resin, polysulfone resin, polyimide resin, and the like.

The ratio of hydrogenated norbornene resin to other thermoplastic resin is 10 to 95:90 to 5, preferably 1 by weight.
5-90: 85-10. More preferably 20-80
: The ratio is 80 to 20. Further, the hydrogenated norbornene resin may contain a comb polymer and a rubber-reinforced thermoplastic resin, each alone or both.

Here, the rubbery polymer is a polymer having a glass transition temperature of 0° C. or lower, and includes ordinary rubbery polymers and thermoplastic elastomers.

In the present invention, a molded article of hydrogenated norbornene resin (
The shape of the molded body (hereinafter simply referred to as "molded body") may be any shape. For example, it may be in the form of an intermediate molded product before making the resin into a final molded product or a final molded product.

Specific examples of the molding method include injection molding, compression molding, and extrusion molding.

In the present invention, the method of dry coating the molded body with the inorganic compound is not particularly limited, but preferably includes vacuum evaporation, sputtering, and the like.

The vacuum evaporation equipment used in the vacuum evaporation method is not particularly limited, and the inorganic compound is heated and evaporated under vacuum, and the evaporated inorganic compound is deposited onto the molded body, preferably 0.001 to 100 μm.
Any material may be used as long as it can be deposited to a thickness of m.

The method of evaporating the inorganic compound is not particularly limited, such as a resistance heating method, a high frequency heating method, an electron beam heating method, etc., but an electron beam heating method is preferable because it has fewer restrictions on the target inorganic compound.

In the second case, the degree of vacuum of the vacuum evaporation equipment used is usually
It is 10'Torr or less, preferably 10-4 Torr or less. Vacuum deposition may be a so-called batch method or a continuous method.

A sputtering method in which the surface of the body under vacuum is irradiated with accelerated ions and the generated atoms are deposited on the molded body is also a preferable method. The method used at this time is
Examples include so-called magnetron sputtering method and facing target sputtering method. The sputtering method may be a so-called batch method or a continuous method.

The inorganic compounds that can be coated on the molded body in the present invention include HA group such as aluminum, metal, lium, and indium, A group such as silicon, tin, and lead, IB group such as copper, gold, and silver, zinc, IIB group such as cadmium, ■B group such as titanium, zirconium, VB group such as vanadium, niobium, tantalum, VB group such as chromium, molybdenum, tungsten, iron, ruthenium, cobalt, rhodium, nickel, palladium, platinum, etc. Compounds containing one or more metals in the lanthanum group, such as group III, gadolinium, and terbium, i.e., oxides and chlorides of the aforementioned metals;
Examples include fluorides, sulfides, nitrides, and hydrides.

Specific examples include oxides such as silicon oxide, aluminum oxide, tin oxide, indium oxide, titanium oxide, tantalum oxide, lead oxide, and zirconium oxide, nitrides such as silicon nitride, titanium nitride, aluminum nitride, and tantalum nitride, and sulfides. There are sulfides such as zinc, molybdenum sulfide, and cadmium sulfide.

Preferred inorganic compounds include silicon oxide, aluminum oxide, titanium oxide, tantalum oxide, lead oxide, zinc oxide, zirconium oxide, silicon nitride, titanium nitride, and aluminum nitride. Two or more of these inorganic compounds may be used for coating at the same time. Furthermore, coating with the inorganic compound may be performed two or more times in succession to provide two or more layers of coating.

The surface of the hydrogenated norbornene resin molded body coated with an inorganic compound in this way is modified, resulting in surface hardness (scratch resistance), hygroscopicity, moisture resistance, water absorption, and heat resistance (heating stability). and other characteristics are significantly improved.

[Examples] Next, the present invention will be specifically explained by examples, but the present invention is not limited to these examples unless it exceeds the spirit thereof.

In the following Examples and Comparative Examples, parts mean parts by weight and % means % by weight unless otherwise specified.

Dry coating was performed using the following experimental equipment.

Vacuum deposition equipment: Manufactured by Sawara Vacuum Machinery Industry 500φ single layer deposition equipment Sputtering equipment: TOKUDA CFS-8ES The evaluation method was as follows.

Surface hardness: Pencil hardness (JIS K5400), value at a load of 100g Hygroscopicity: Water absorption rate (%) of dry sample held in a constant temperature and humidity chamber at a temperature of 80°C and a humidity of 95% for 240 hours Heat resistance: Sample 50 while the gear is open at 140℃
The sample was held for 0 hours and the change in yellowness was examined. Yellowness was determined according to JIS K7103.

Reference Example 1 (Production of hydrogenated norbornene resin (A)) In a nitrogen atmosphere, 8-
Methyl-8-methoxycarbo2.5 7.10 Nyltetracyclo[4,,4,0,1,1-3-dodecene 5kg, toluene 20Il, molecular weight regulator 1
- 650 g of hexene, concentration of WCl6 as catalyst 0.0
86 ml of a 50 M/N chlorobenzene solution 34 ml of a paraaldehyde toluene solution with a concentration of 0.1 M/ρ. 205 ml of a toluene solution of diethylaluminium monochloride with a concentration of 0.5 M/(l) was added and reacted at 80°C for 4 hours. To this polymer solution was added 1.0 ml of triethanolamine.
After adding 16 kg of methanol and stirring thoroughly, unreacted monomers and catalyst were removed by discarding the upper layer. After adding 0.05% of pentaerythrityl-tetrakis [3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate] based on the polymer to the obtained lower layer liquid, it was dried with a steam strip. The polymer was recovered by this.

This polymer was dissolved in tetrahydrofuran, charged into a high-pressure reactor, 1 kg of 5% palladium/alumina catalyst was added as a hydrogenation catalyst, the temperature was 150°C, and the hydrogen pressure was 100 kg.
The hydrogenation reaction was carried out at /cat for 5 hours.

The obtained polymer was filtered to remove the catalyst, and then dried with a steam strip to recover the hydrogenated norbornene resin (A).

The intrinsic viscosity (ηinh) of the obtained polymer was 0°75
ml/g, no oleorefin peak was observed on the NMR chart, and the hydrogenation rate was 99% or more.

Reference Example 2 (Production of hydrogenated norbornene resin (B)) In Reference Example 1, 4.5 kg of 8-methyl-8-methoxycarbonyltetracyclo[4,4,0,12°517·1°co-3-dodecene and 5-methyl 5-methoxycarbonylbicyclo[2,2,1]-2-heptene 0. Polymerization, hydrogenation, etc. were carried out in the same manner as in Reference Example 1, except that the weight was changed to 5 kg, to obtain a hydrogenated norbornene resin (B).

The intrinsic viscosity (η1nh) of the obtained polymer was 0°90d.
ff/g, no oleorefin beak quality was observed on the NMR chart, and the hydrogenation rate was 99% or more.

Reference Example 3 (Production of hydrogenated norbornene resin (C)) In Reference Example 1, 8-methyl-8-methoxycarbonyltetracyclo[4,4,0,1""17.10] 3-dodecene 4.5 ) cg and dicyclopentadiene 0. 5kg
Polymerization, hydrogenation, etc. were carried out in the same manner as in Reference Example 1, except for changing to, to obtain a hydrogenated norbornene resin (C).

The intrinsic viscosity (ηinh) of the obtained polymer was 0985
c[/g, no oleorefin peak was observed in quality on the NMR chart, and the hydrogenation rate was 99% or more.

Reference Example 4 (Production of hydrogenated norbornene resins (D) and (E)) Polymerization, hydrogenation, etc. were carried out in the same manner as in Reference Example 1, except that the amount of hydrogenation catalyst and hydrogenation time were changed. Hydrogenated norbornene resin (D) with hydrogenation rate of 97%, hydrogenation rate of 9
A 5% hydrogenated norbornene resin (E) was obtained.

Reference Example 5 (Production of hydrogenated norbornene resin (F)) In a nitrogen atmosphere, a norbornene ring-containing monomer, tetracyclo[4,4,0,12
"', 17°10] 3-dodecene 3.50 kg, pentacyclo[6,5,1°1, 0, 0
``13] -4-Pentadecene 1゜3.6 2.7 Using 50 kg, toluene 2091, molecular weight regulator 1-hexene 75 ml, catalyst TLC14 toluene solution with a concentration of 1.0 M/11 150 ml, triethylamine 200 ml of a toluene solution with a concentration of 0.1 M/ρ and 800 ml of a toluene solution with a concentration of triethylaluminum of 1.0 M/g were added, and the mixture was reacted at 25°C for 2.5 hours. The polymer was recovered by the method, and the intrinsic viscosity (ηinh) was 0.47
cM2/g (in chloroform, 30°C, concentration 0.
5g/df) hydrogenated norbornene resin (F)2.
Obtained 50 kg.

Example 1 Using the resin (A) obtained in Reference Example 1, a molded plate of 80 x 55 x 2.4 dimensions was manufactured using an injection molding machine (Niigata Tekko, NN30B). The obtained molded plate was installed in a 650φ vacuum deposition machine, and the pressure inside the machine was 1O-4 Torr, and the thickness was 0.3t.
A SIO2 film of m was formed.

Table 1 shows the evaluation results of the molded plate on which this SiO2 film was deposited.

Example 2 Using the resin (A) obtained in Reference Example 1, a molded plate of 80 x 55 x 2.4 mm was manufactured using an injection molding machine (Niigata Tekko, NN30B). The obtained molded plate was installed in a sputtering machine, and the pressure inside the machine was set to 10-3 Torr, and the thickness was 0.3 μm.
A SiO2 film was formed. Table 1 shows the evaluation results of the molded plate on which this SIO2 film was deposited.

Examples 3 to 7 In Example 1, the resins were (B), (C), and (
A SiO2 film was formed on a molded plate in the same manner as in Example 1 except that D), (E), and (F) were changed. The evaluation results are shown in Table-1.

Example 8 50 parts of the resin (A) produced in Reference Example 1 and polystyrene (
50 parts of Topolix 600) were kneaded at 280° C. for 5 minutes using a plastic bender to obtain a thermoplastic main resin composition (G). Using the obtained thermoplastic resin composition (G), a molded plate was manufactured in the same manner as in Example 1, a S l 02 film was deposited in the same manner as in Example 1, and the evaluation results of the resin plate are shown. −
Shown in 1.

Comparative Examples 1 to 7 In Examples 1.3 to 8, the resin plates before forming the SiO3 film were evaluated, and the results are shown in Table 1.

Examples 9 and 10 A silicon nitride film with a thickness of 0.2 μm (Example 9) and a silicon nitride film with a thickness of 0.2 μm were prepared in the same manner as in Example 2 except that the inorganic compound was changed.
Molded plates each having a 2 μm A 120 s film (Example 10) formed thereon were obtained. The evaluation results of these molded plates are shown in Table-1.

Margins below [Effects of the Invention] As described above, the present invention modifies the surface of a hydrogenated norbornene resin molded product by dry coating it with an inorganic substance, thereby improving the surface of the resin molded product. The scratch resistance, water resistance, humidity resistance, and heat resistance of the material can be significantly improved.

The molded product of the present invention is suitable for optical parts such as optical lenses and optical discs; automobile windshields, ceiling materials, headlamp lenses, fog lamp lenses, stop lamp lenses, turn lamp lenses, rear combination lenses, room lamp lenses, and lamps. Automotive parts such as glue flapers, rearview mirrors, room mirrors, fuse covers, panel meter covers, wheel caps, and general interior and exterior parts; camera parts such as lens barrels, mirror frames, and other camera exterior parts; fluorescent light covers and lampshades Lighting equipment parts such as; Display parts; Electrical parts such as microwave oven lids and washing machine laundry lids; Electronic parts such as light emitting diode encapsulants; OA equipment parts; Audio equipment parts such as cassette cases and cassette halves; Ramen cups , containers such as search cups, crystal cups, folding boxes, bento boxes, steam containers, frozen food containers, dry food containers, microwave food containers, trays; Building materials: Civil engineering materials: Shipbuilding materials: Agricultural materials; Logistics materials; Medical equipment such as syringes and petri dishes; Various nameplates; Daily goods; Films; Sheets;
Useful for pipes; bottles; and many other applications.

Patent applicant: Japan Synthetic Rubber Co., Ltd.

Claims (1)

[Claims] A monomer consisting of at least one compound represented by the following general formula (I), or a monomer obtained by ring-opening polymerization of this monomer and a copolymerizable monomer copolymerizable therewith. A molded article of a hydrogenated norbornene resin obtained by dry-coating the surface of a hydrogenated polymer molded article obtained by further hydrogenating a ring-opened polymer obtained by dry coating with an inorganic compound. General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, A and B are hydrogen atoms or hydrocarbon groups having 1 to 10 carbon atoms, X and Y are hydrogen atoms, hydrocarbon groups having 1 to 10 carbon atoms, -(CH_2)_
nCOOR^1, -(CH_2)_nOCOR^1, -
(CH_2)_nCN, -(CH_2)_nCONR^
2R^3, -(CH_2)_nCOOZ, -(CH_2
)_nOCOZ, -(CH_2)_nOZ, -(CH_
2) _nW, or ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼ composed of X and Y, and m is 0 or 1. In addition, R^1, R^2
, R^3 and R^4 are hydrocarbon groups having 1 to 20 carbon atoms,
Z is a hydrocarbon group or hydrogen atom, W is SiR^5_pD
_3_-_p (R^5 is a hydrocarbon group having 1 to 10 carbon atoms,
D represents -OCOR^5 or -OR^5, p represents an integer of 0 to 3), and n represents an integer of 0 to 10. ]