JPH04139154A - Polycarbonate and its use - Google Patents

Abstract

NEW MATERIAL:A compound of formula I (R1 is methyl; R2 is <=30C hydrocarbon, 2-30C hydrocarbon having an ether bond; (x) is 0-2; (y) is 2-4). EXAMPLE:The condensed product of neopentyl-di(2-ethylhexyl) carbonate. USE:A lubricant and an electric insulating oil. The compound has excellent compatibility with fluorocarbon hydrogenated products (e.g. Freon R-134a) not decomposing the ozone layer and is suitable especially for freezers and electric refrigerators using the Freon as cooling media thereof. PREPARATION:For example, a polyol of formula II is made to react with a carbonate compound of formula III (but the boiling point of R2O is lower than the boiling point of the polyol) in a ratio of m1/ym2 (m1 is the mol number of the carbonate compound; m2 is the mol number of the polyol; (y) is the number of OH groups of the polyol) of 2-200, preferably 3-80, with removing the prepared alcohol (R2OH) outside the system to provide the compound of formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION Technical Field of the Invention The present invention relates to polycarbonate and its uses, and more particularly to polycarbonate, which is a non-ozone depleting fluorocarbon hydrogenated compound (HFC, Hy
drogenated Fluo+o (a+bon)
, for example, polycarbonate which has excellent compatibility with Freon R-134a, as well as excellent lubricity and electrical insulation;
The present invention also relates to lubricating oils and electrical insulating oils made of this polycarbonate, especially lubricating oils suitable for refrigerators that use ozone-depleting CFCs as refrigerants, and lubricating oils and electrical insulating oils particularly suitable for electric refrigerators.

TECHNICAL BACKGROUND OF THE INVENTION Polycarbonates are useful as a variety of lubricating oils or components thereof.

However, the volume resistivity of conventional polycarbonate is on the order of 1011 to 10'2 Ω.Especially in applications such as lubricating oil and electrical insulating oil that require electrical insulation, electrical insulation is not always sufficient. It wasn't enough.

By the way, recently, in the lubricating oil for refrigerators, the refrigerant gas is Freon R-134a (CH2
With the change to F-CF3), mineral oils and alkylbenzene compounds, which have been conventionally used as lubricating oils for refrigerators, can no longer be used because of their lack of compatibility with refrigerant gas. Therefore, polypropylene glycol, polypropylene glycol monoalkyl ether, polypropylene glycol dialkyl ether, and the like have come to be used as lubricating oils for refrigerators. However, since the above compound has low compatibility with Freon R-134a, it was not suitable for lubricating oil for refrigerators that use Freon, which does not deplete the ozone layer, as a refrigerant.

Therefore, there has been a desire for a polycarbonate that has excellent compatibility with Freon R-134a, as well as excellent lubricity and electrical insulation properties.

Note that French Patent No. 2.321.477 discloses a tricarbonate of trimethylolpropane represented by the following general formula.

CL -CH2c+cH20CoORh In the above general formula, R is a branched or unbranched alkyl group having 4 to 12 carbon atoms, a cycloalkyl group, an allyl group, an aralkyl group, and these groups are substituted with a lower alkyl group. Sometimes there are. According to the document, the tricarbonate can be used as the main component of a thermally stable lubricant, which is said to be used in particular in supersonic aircraft.

Purpose of the Invention The present invention aims to solve the problems associated with the prior art as described above, and provides a fluorocarbon hydrogen additive that is non-destructive to the ozone layer, in particular excellent compatibility with Freon R-134, and The purpose is to provide polycarbonate with excellent lubricity and electrical insulation properties.

The present invention also provides a lubricating oil and electrical insulating oil made of the polycarbonate described above, particularly a lubricating oil suitable for refrigerators that use CFCs that do not deplete the ozone layer as a refrigerant, and a lubricating oil and electrical insulating oil particularly suitable for electric refrigerators. It is intended to.

Summary of the Invention The novel polycarbonate according to the present invention is represented by the following general formula [I].

(R1). C (CH20COOR2)...C1]
In the above general formula [I], R1 is a methyl group, and R2 is each independently a hydrocarbon group having 30 or less carbon atoms or a hydrocarbon group having an ether bond and having 2 to 30 carbon atoms. , X is an integer from 0 to 2, and y is 2
It is an integer of ~4.

Furthermore, the novel lubricating oil and electrical insulating oil according to the present invention are
It is characterized by being made of the above polycarbonate.

DETAILED DESCRIPTION OF THE INVENTION The polycarbonate according to the present invention and its uses will be specifically described below.

The novel polycarbonate according to the present invention is represented by the following general formula [I].

(R1) C (CH20COOR2) ・ [I]
In the above general formula [I], R1 is a methyl group, and R2 is each independently a hydrocarbon group having 30 or less carbon atoms or a hydrocarbon group having an ether bond and having 2 to 30 carbon atoms. , X is an integer from 0 to 2, and y is 2
It is an integer of ~4.

The hydrocarbon group for R2 above includes an aliphatic hydrocarbon group, a ring hydrocarbon group, an aromatic hydrocarbon group, an aromatic aliphatic hydrocarbon group, and the general formula % formula % (wherein, R3 has a carbon atom number of 2 ~3 alkylene group, R4 is a hydrocarbon group having 28 or less carbon atoms, and q
is an integer of 1 to 20).

Specific examples of the aliphatic hydrocarbon group for R2 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, 2,3-dimethylbutyl group, and S-butyl group. , t-butyl group, pentyl group,
Isopentyl group, neopentyl group, n-hexyl group, 2
-ethylhexyl group, isohexyl group, n-heptyl group, isoheptyl group, n-octyl group, isooctyl group,
n-nonyl group, isononyl group, n-decyl group, isodecyl group, n-undecyl group, isoundecyl group, n-dodecyl group, ittodecyl group, n-hlyzocyl group, isotridecyl group, n-tetradecyl group, isotetradecyl group ,
n-pentadecyl group, isopentadecyl group, n-hexadecyl group, isohexadecyl group, n-heptadecyl group,
Isoheptadecyl group, n-octadecyl group, isooctadecyl group, n-nonyldecyl group, isononyldecyl group,
Examples include n-icosanyl group, isoicosanyl group, 2-ethylhexyl group, and 2-(4-methylpentyl) group.

Further, specific examples of the alicyclic hydrocarbon group in R2 include a cyclohexyl group, 1-cyclohexenyl group, methylcyclohexyl group, dimethylcyclohexyl group, decahydronaphthyl group, tricyclodecanyl group, etc. I can do it.

Furthermore, specific examples of the aromatic hydrocarbon group in R2 include phenyl group, o-tolyl group, p-1lyl group, m
Examples include -tolyl group, 2,4-xylyl group, mesityl group, and 1-naphthyl group.

Furthermore, specific examples of the aromatic aliphatic hydrocarbon group in R2 include benzyl group, methylbenzyl group, β-
Examples include phenylethyl group (phenethyl group), 1-phenylethyl group, I-methyl-1-phenylethyl group, p-methylbenzyl group, styryl group, and cinnamyl group.

Specific examples of the alkylene group in R3 above are:
Examples include ethylene group, propylene group, and isopropylene group.

Further, examples of the hydrocarbon group for R4 include an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group. Specific examples of these include the same groups as those listed as specific examples of the aliphatic hydrocarbon group, alicyclic hydrocarbon group, and aromatic hydrocarbon group for R2, respectively. .

Specifically, the glycol ether group represented by the above general formula includes ethylene glycol monomethyl ether group, diethylene glycol mono-n-butyl ether group, triethylene glycol monoethyl ether group, propylene glycol monomethyl ether group, and propylene glycol mono-n-butyl ether group. group, dipropylene glycol monoethyl ether group, tripropylene glycol monomethyl ether group, tripropylene glycol mono-n-butyl ether group, and the like.

Preferred polycarbonates represented by the above general formula [I] include, for example, polycarbonates represented by the following formulas.

(1)(CH3)2C(CH20COOR2)2C2
) C (CH20COORI! ) 4 Above (1
) and (2), R2 is represented by the above general formula [I
is the same group as R2 in ].

The polycarbonate represented by the above general formula [I] can be produced, for example, by the following method.

(a) General formula [I1] % formula % [) [In formula [I1], R1, X and Y are respectively R+, X,! / and (b) general formula [I11] % formula % [I1 "In the formula [+11], R2 is the same as R2 in the above general formula [I]" and the boiling point of R20H is lower than the boiling point of the polyol, m, /ym2 (where m is the number of moles of the carpho-inert compound, m2 is the number of moles of bool, and y is the number of moles of the polyol. represents the number of hydroxyl groups) or 2 to 2
While heating an amount of carbonate compound, preferably in the range of 3 to 80, in the presence of a basic catalyst, the alcohol (R20H) produced is removed from the reaction system by distillation, and the reaction is carried out to a reaction rate of 95% or more. .

In carrying out the above reaction, it may be desirable to replace the air in the reactor with nitrogen, or it may not be necessary to replace the air with nitrogen.

Next, after removing the base catalyst, the unreacted carbonate compound is removed from the reaction system by distillation to obtain the aliphatic polycarbonate represented by the general formula [N].

Specific examples of the carbonate compound represented by the above general formula [III] include methyl carbonate, /ethyl carbonate, dipropyl carbonate, dibutyl carbonate, methyl carbonate, /ethyl carbonate, dipropyl carbonate, dibutyl carbonate, dihexyl carbonate, octyl carbonate,
/-[2-ethylhexyl]carbonate and cyclohexyl carbonate are preferably used.

In this method, the alcohol produced in the carbonation reaction is removed from the reaction system by distillation while the carbonation reaction proceeds, so the alcohol produced in this reaction,
That is, the alcohol represented by R20H needs to have a boiling point lower than that of the polyol.

Moreover, the carbonate compound has m + /V m 2
(In the formula, ml is the number of moles of the carbonate compound, m
(2 is the number of moles of the polyol, and y represents the number of hydroxyl groups in the polyol) is used in an amount in the range of 2 to 200, preferably 3 to 80.

By limiting the amount of the carbonate compound used in this way, it is possible to suppress the production of polycarbonate with a high degree of polymerization.

In this method, the reaction is carried out by charging the above-mentioned polyol and carbonate compound into a reaction vessel, heating it in the presence of a base catalyst, and removing the generated alcohol from the reaction system by distillation to achieve a reaction rate of 95%. After the reaction is carried out to the above extent, and then the base catalyst is removed, the unreacted carbonate compound is removed from the reaction system by distillation. A reaction rate of 95% or more means that the reaction is carried out until the alcohol produced above is produced in an amount of 0.95 times the mole or more of ym2.

The above-mentioned base catalysts include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal carbonates and hydrogen carbonates such as sodium carbonate and sodium hydrogen carbonate,
Alkali metal alcoholades such as sodium methoxide, potassium methoxide, lithium methoxide, and cesium methoxide, and alkali metal compounds such as sodium hydride and sodium amide are preferably used. Among these, alkali metal alcoholades are particularly preferred. In addition, for example, alkaline earth metal compounds such as magnesium hydroxide and calcium hydroxide, trimethylamine,
Organic amino compounds such as triethylamine, imidazole, and tetramethylammonium hydroxide are also used. The amount of these catalysts used is usually such that the number of moles of catalyst/the above V m 2 is 10-1 to 10-7, preferably 10-
It is used in a range of 2 to 10-5.

In this method, the reaction is usually carried out at 50 to 300°C,
Preferably it is carried out at a temperature of 60 to 200°C. The reaction time is usually 0.5 to 200 hours, preferably 1 to 10 hours.
It is 0 hours.

After the reaction is completed, the catalyst is removed by washing with water or neutralizing with acid. Examples of acids include solid acids such as sulfonic acid type ion exchange resins; inorganic acids such as carbonic acid, ammonium carbonate, ammonium chloride, hydrochloric acid, sulfuric acid, and phosphoric acid; acetic acid,
Organic acids such as phenol are used. Among these, for example, sulfonic acid type ion exchange resins and weak inorganic acids such as ammonium carbonate are preferably used.

According to this method, after removing the base catalyst, the unreacted carbonate compound is removed by distillation under reduced pressure. It is possible to prevent the polymerization of the resulting polycarbonate and obtain the desired polycarbonate in high yield.

The polycarbonate thus obtained may be treated with an adsorbent such as activated clay or activated carbon or washed with water to remove trace amounts of impurities, if necessary. In particular, according to such treatment, trace amounts of ionic compounds and polar compounds can be removed, so the obtained polycarbonate can be stably maintained.

According to the above method, when dimethyl carbonate is used as the carbonate compound in the above reaction, instead of removing methanol from the reaction system as an azeotrope with dimethyl carbonate, cyclohexane, benzene, hexane, etc. are added to the reaction system in advance. can be added as an azeotropic solvent, and methanol can be removed from the reaction system as an azeotrope with these azeotropic solvents. The azeotropic solvent is generally used in an amount of 5 to 100% by weight based on 100% by weight of dimethyl carbonate.

According to this method, in the reaction, methanol is removed from the reaction system as an azeotrope with the azeotropic solvent, and after the reaction is completed, unreacted dimethyl carbonate is recovered from the reaction mixture, so the recovery rate can be reduced. can be increased.

Alternatively, as described above, after recovering methanol as an azeotrope with dimethyl carbonate, the above azeotropic solvent is added to this azeotrope, and methanol is recovered as an azeotrope with these azeotropes. Dimethyl carbonate can also be recovered by removal from dimethyl carbonate.

According to the above method, after the reaction between the polyol and the carbonate compound is completed, the base catalyst used is removed, and then the unreacted carbonate compound is removed, so the desired polycarbonate can be produced in high yield. Obtainable.

Further, as another method for producing polycarbonate according to the present invention, there is the following method.

First, (a) a polyol represented by general formula [II] (R,), C(CH20H) -[■], (b) general formula [IV] R20H... [■ Co[in formula [rV], R2 is R in the above general formula [I]
2] and (c) a monoalcohol represented by the general formula [V] R, OCOOR, -[V] [In the formula [V], R5 each independently has a carbon atom number of 1
~2 alkyl group], and the boiling point of R50H is lower than the boiling point of the above polyol and monoalcohol, and mi/ym2(
In the formula, ml is the number of moles of the carbonate compound, m2
is the number of moles of the polyol, and y represents the number of hydroxyl groups in the polyol) is in the range of 2 to 200, preferably 3 to 8, while heating the carbonate compound in the presence of a base catalyst to generate the alcohol ( R50H) is removed from the reaction system by distillation, and the reaction is carried out to a reaction rate of 95% or more.

In addition, when carrying out the above reaction, it is desirable to replace the air in the reactor with nitrogen, but it is not necessary to replace the air with nitrogen.

Next, after removing the base catalyst, unreacted carbonate compounds [R60C0
2R6 (wherein R6 is each independently R2 to R
5)] is removed from the reaction system by distillation to obtain a polycarbonate represented by the above general formula [I].

In this method, the alcohol produced in the carbonation reaction is removed from the reaction system by distillation while the carbonation reaction proceeds, so the alcohol produced in this reaction,
That is, the alcohol represented by R6oH needs to have a lower boiling point than the above polyol and monoalcohol.

In addition, the carbonate compound has m + / ym 2 (
In the formula, ml is the number of moles of the carbonate compound, m2
is the number of moles of the polyol, and y represents the number of hydroxyl groups in the polyol) is used in an amount ranging from 2 to 200, preferably from 3 to 80.

By limiting the amount of the carbonate compound used in this way, it is possible to suppress the production of polycarbonate with a high degree of polymerization.

In this method, the reaction is carried out by charging the above-mentioned polyol, monoalcohol, and carbonate compound into a reaction vessel, heating it in the presence of a base catalyst, and removing the generated alcohol from the reaction system by distillation. rate 95
% or more, and then, after removing the base catalyst, the unreacted carbonate compound is removed from the reaction system by distillation. A reaction rate of 95% or more means that the reaction is carried out until the alcohol produced above is produced in an amount of 0.95 times the mole or more of ym2.

The basic catalyst, reaction temperature, reaction time, removal of the catalyst after the completion of the reaction, removal of impurities, and recovery of unreacted dimethyl carbonate are the same as in the previous production method.

In the method for producing polycarbonate described at the beginning, carbonate compounds other than dimethyl carbonate and diethyl carbonate, represented by general formula [I11], are difficult to obtain and therefore need to be synthesized in advance. On the other hand, in this production method, polycarbonate is produced using an easily available carbonate compound represented by general formula [V] (dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate) and a monoalcohol represented by general formula [IV]. Therefore, the synthesis of carbonate compounds as described above is not necessary and is economical.

Furthermore, according to this method, the desired polycarbonate can be obtained in a high yield as in the case of the previous production method.

The polycarbonate according to the present invention has excellent lubricity and has a volume resistivity on the order of 10 13 to 10 14 Ω·mm, and has higher electrical insulation than conventional polycarbonate. Therefore, the polycarbonate according to the present invention can be used for lubricating oils and electrical insulating oils that require electrical insulation properties, and is particularly suitable for lubricating oils and electrical insulating oils for electric refrigerators. ing.

Further, the polycarbonate according to the present invention is Freon R-1
Since it has excellent compatibility with ozone layer non-depleting fluorocarbons such as 34a, it is particularly suitable as a lubricating oil for refrigerators that use ozone layer non-depleting fluorocarbons as refrigerants.

Effects of the Invention The polycarbonate according to the present invention is Freon R-1342.
It has excellent compatibility with non-ozone layer depleting CFCs such as chlorofluorocarbons, and has excellent lubricity and electrical insulation properties.

The polycarbonate according to the present invention having the above-mentioned effects can be used in lubricating oils such as refrigerating machine lubricating oils, automobile engine oils, automobile gear oils, rolling lubricating oils, and textile lubricating oils, especially those that require electrical insulation. We can provide lubricating oil and electrical insulating oil.

The polycarbonate according to the present invention is particularly suitable as a lubricating oil for refrigerators that use CFCs that do not destroy the ozone layer as a refrigerant, and as lubricating oils and electrical insulating oils for electric refrigerators.

EXAMPLES The present invention will be explained below with reference to Examples, but the present invention is not limited to these Examples.

The analysis and performance evaluation of polycarbonate in Examples and Comparative Examples were based on the following test methods.

(1) Analysis method a, average molecular weight ■ Using a GPC system manufactured by Shimabara Seisakusho, the average molecular weight was determined based on Bostyrene standards. The measurement conditions are shown below.

4 columns polystyrene gel (G-2000HXL+
G-2[If1[I1(XL+G-3[I[I[IHX
L+G-4000HXL), detector: differential refractometer, temperature: 40°C, solvent: tetrahydrofuran, elution rate: 0.7 mA'/min, infrared absorption spectrum KBr with JASCO infrared spectrometer A-302 Measure by applying a sample between the plates.

(2) Evaluation method a, Kinematic viscosity Its K-2283 b, Pour point Its K-2269 C9 load capacity The load capacity was determined by using a Falex tester and breaking in for 5 minutes at a load of 250], bf. After operation, load is applied, and the load value at which seizure occurs is determined, and this value is taken as the load capacity value.

d1 Volume resistivity The volume resistivity of polycarbonate is ASTM D 25
It was determined in accordance with 7.

e, Compatibility with Freon R-134a (1) Sample 1 in a test tube with an inner diameter of IQ mm and a depth of 20 ann.
Take a ml sample and cool it in a dry ice-acetone bath.
Slowly introduce Freon R-1348 from the cylinder container and collect it in an amount larger than the amount of sample. Next, stir with a spatula, transfer to a -20°C refrigerant bath, and sample / Freon R-13.
The solubility is examined when the volume ratio of 4a is 1/1.

If it is completely uniform, mark it as ○; if it does not dissolve, mark it as ×.

(2) In order to investigate the compatibility between the carbonate product and Freon R-134a in more detail, we tested lubricating oil and Freon R-13a.
4a in various proportions and sealed in a glass tube, and the limit temperature (critical temperature) at which the two are compatible is determined.

Example 1 301 g (289 mol) of neopentyl glycol was placed in a 51-capacity flask equipped with a 10-stage sieve tray distillation column.
, di[2-ethylhexyl]carbonate 4293
g (15,01 mol) and 28% by weight of NaOCH
1.0 g of methanol solution of No. 3 (NaOCH30,005
Mol) was prepared.

This mixture was heated under reduced pressure (40-10 mm Hg) for 13
The reaction was carried out for 10 hours while heating to 0 to 160°C and distilling off the produced 2-ethylhexanol.

The distilled 2-ethylhexanol weighed 742 g (5,
70 mol), and the 2-ethylhexanol yield was 9
It was 9%.

In the reaction mixture thus obtained, the Na used
After neutralizing the catalyst with an aqueous solution containing ammonium carbonate in a molar amount 5 times that of OCH3 and washing with water, unreacted di[2-
Ethylhexyl] carbonate was removed to obtain 962 g of polycarbonate.

The obtained polycarbonate is liquid and H-NMR
From the results of analysis, IR analysis, and GC-Ms analysis, it was found that it had the following structure.

CH2CH3 The obtained polycarbonate was measured by 'H-NMR, and the following peaks appeared on the chart. In addition,
During this measurement, CDCl3 was used as a solvent.

0, 87~0. 93ppm (1+i 12H)
1. 0ppm (s 6H) 1.25-1. 35ppI11(81i)1, 35
~1. 45ppm (8H) 1.59-1. 65
ppm (2H) 3, 97ppm (s 4H) 4, 0-4. O8ppm (4H) As a result of GC-MS analysis of this polycarbonate, a molecular ion peak of M' appeared on the chart at m/e = 41-7.

Moreover, the infrared absorption spectrum of the obtained polycarbonate is shown in FIG.

Furthermore, the results of GPC analysis of the obtained polycarbonate are shown below. In addition, it was confirmed that a condensate of neopentyl di[2-ethylhexyl] carbonate was partially present in the product.

Weight average molecular weight (]'aW)/number average molecular weight (Mn) [
GPC]: 1.05 Weight average molecular weight (Mw) by polystyrene conversion method
+ 484 Amount of sodium remaining in the product: 0.01 ppm or less Total acid value in the product: 001 or less Table 1 shows the evaluation results of the lubricating oil's basic performance and electrical insulation.

Example 2 In Example 1, the amount of neobentyl glycol of Example 1 and the methanol solution of 28% by weight Na OCH3 was 258 g (2.48 mol), respectively.
2. 0 g (NaQC)13Q, [I11 mol)
and instead of di(2-ethylhexyl) carbonate, di[I,3-dimethylbutyl]carbonate 2
Prepare 707g (11.75mol) and reduce the degree of vacuum to 50~
Polycarbonate 73 was prepared in the same manner as in Example 1, except that the reaction temperature was 120 to 135°C.
6g was obtained.

In addition, the distilled amount of 1,3-dimethylbutanol is 502
g (4.91 mol), and the yield of 1,3-dimethylbutanol was 99%.

The obtained polycarbonate is liquid and H-NMR
From the results of analysis, IR analysis, and GC-Ms analysis, it was found that it had the following structure.

As a result of measuring the obtained polycarbonate by 'H-NMR, the following peaks appeared on the chart. In addition,
During this measurement, CDCl was used as the solvent.

was used.

0, 93ppm (d 12H) 1, O2ppm (s 6H) 1, 27++pm (d 6) 1) 1, 31pp
m (2H) 1, 62ppm (2) 1) 1, 70ppm (2tl) 3, 9 7 ppm (s 4H) 4, 85pp
m (2H) As a result of GC-Ms analysis of this polycarbonate, a molecular ion peak of M' appeared on the chart at m/e=361.

Furthermore, data on the infrared absorption spectrum of the obtained polycarbonate is shown below.

Main peak v C-82800~3000an δC-H1460~14Han-' v C= 0 1745an-', +25 [IC!
+1 Furthermore, the results of GPC analysis of the obtained polycarbonate are shown below. In addition, it was confirmed that a condensate of neopentyl-di[I,3-dimethylbutyl]carbonate was partially present in the product.

Weight average molecular weight (Mw)/number average molecular weight (Mn) [G
P Cl: 1.09 Weight average molecular weight (M w ) by polystyrene conversion method
・440 Residual amount of sodium in product: 0. Total acid value in the product: Nppm or less: O, O1 or less The evaluation results of the basic performance and electrical insulation properties of the lubricating oil are shown in Table 1.

Example 3 In Example 2, neopentyl glycol, 28 wt% Na OCH3 in methanol and di[I
, 3-dimethylbutyl] carbonate were charged in amounts of 127 g (1.22 mol) and 0.68 g (NaO
CL 0.1103 mol), 2817 g (12,
420 g of polycarbonate was obtained in the same manner as in Example 1, except that the amount of polycarbonate was 23 mol).

The amount of 1,3-dimethylbutanol distilled out was 245g (
2.40 mol), and the yield of 1,3-dimethylbutanol was 98%.

The obtained polycarbonate is liquid and H-NMR
The results of analysis, IR analysis and GC-Ms analysis are shown in Example 2.
It was found that it had the same structure as the polycarbonate of Example 2.

Furthermore, the results of GPC analysis of the obtained polycarbonate are shown below. In addition, it was confirmed that a condensate of neopentyl-di[I,3-dimethylbutyl]carbonate was partially present in the product.

Weight average molecular weight (Mw)/number average molecular weight (Mn) [GP
C]: 1.09 Weight average molecular weight (Mw) by polystyrene conversion method
:372 Residual amount of sodium in product: O,O1ppm1pp
Total acid value in the product: 0.01 or less The evaluation results of the lubricating oil's basic performance and electrical insulation properties are shown in Table 1.

Example 4 Neopentyl glycol 313 was prepared in the same manner as in Example 1.
g (3,01 mol), 2-ethylhexanol 27
35 g (21,0% mol) and 1901 g (21,13 mol) dimethyl carbonate, 28% by weight N
a Methanol solution of OCH3 1, 3 g (Na
OCH30,0067 mol) was charged.

This mixture was heated at 110 to 160° C. for 11 hours under normal pressure, and the methanol produced was distilled off. The amount of methanol distilled out was 852 g (26.62 mol), and the methanol yield was 98.5%.

This mixture was then heated under reduced pressure (130~IOm+Hg)
The mixture was heated to 130 to 170°C and reacted for 8 hours, and methanol, dimethyl carbonate, 2-ethylhexanol and methyl-2-ethylhexyl carbonate were distilled off.

The reaction mixture thus obtained was post-treated in the same manner as in Example 1 to obtain 1103 g of polycarbonate.

The obtained polycarbonate is liquid and H-NMR
The results of analysis, IR analysis and GCMs analysis were consistent with Example 1, confirming that it had the same structure as the polycarbonate of Example 1.

Furthermore, the results of GPC analysis of the obtained polycarbonate are shown below. In addition, it was confirmed that a condensate of neopentyl di[2-ethylhexyl] carbonate was partially present in the product.

Weight average molecular weight (IVW)/number average molecular weight (IVn) [
GPC]: 1.06 Weight average molecular weight (Mw) by polystyrene conversion method
: 500 Residual amount of sodium in product: 0. [11 ppm or less Total acid value in the product/0.01 or less The evaluation results of the lubricating oil basic performance and electrical insulation properties are shown in Table 1.

Example 5 In the same manner as in Example 1, pentaerythritol 136
g (1,00 mol), n-butanol 1481 g (2
0.01 mol), dimethyl carbonate 1801 g (
20,02 mol) and 28% by weight N! QC)+1 methanol solution 0. 94 g (llaOcH3[I
,0048 mol) was charged.

This mixture was heated at 90 to 135°C for 7 hours under normal pressure,
The generated methanol was distilled off. The amount of methanol distilled out was 760 g (23.76 mol), and the methanol yield was 99.0%.

This mixture was then heated under reduced pressure (760-110III
QHg) was heated to 140-150°C and reacted for 10 hours, and methanol, dimethyl carbonate, n-butanol and methylbutyl carbonate were distilled off.

The reaction mixture thus obtained was post-treated in the same manner as in Example 1 to obtain 407 g of polycarbonate.

The resulting polycarbonate is a viscous liquid;
From the results of H-NMR analysis, IR analysis, and GPC analysis, it was found that it had the following structure.

C [CL -0-C-OCH2CH2CH2CH3.

As a result of measuring the obtained polycarbonate by 'H-NMR, the following peaks appeared on the chart. In addition,
During this measurement, CDC/i was used as a solvent.

0, 9! 5ppm (tri 12H) 1, 4
2ppm (8H) 1, 65ppm (88) 4, 14ppm (tri 8H) 4, 24pp
a+ (s 8H) Furthermore, the infrared absorption spectrum of the obtained polycarbonate is shown in FIG.

Furthermore, the results of GPC analysis of the obtained polycarbonate are shown below. In addition, it was confirmed that a part of the polycarbonate condensate represented by the above formula was present in the product.

Weight average molecular weight (Mw)/number average molecular weight (Mn) [GP
C] :1. I9 Weight average molecular weight by polystyrene conversion method (Fii!w
) Near 66) Residual amount of IJum in the product: 0.01 ppm or less Total acid value in the product: 0. O] Table 1 shows the evaluation results of the lubricating oil's basic performance and electrical insulation properties.

The polycarbonates of Examples 1 to 5 were all excellent in lubricity and electrical insulation properties determined from load resistance values.

[Brief explanation of the drawing]

FIG. 1 and FIG. 2 are infrared absorption spectra of the polycarbonates obtained in Example 1 and Example 5, respectively. Patent Applicant Mitsui Petrochemical Industries Co., Ltd. Representative Patent Attorney Shun Suzuki Partial Patent Office Procedural Amendment September 24, 1991 Commissioner Wataru Fukasawa 2゜Name of Invention Polycarbonate and Its Uses 3゜Person making the amendment Relationship to the incident Patent applicant name: Mitsui Petrochemical Industries, Ltd. 4゜ Representative Address: 3rd floor, Araku Building, 2-19-2 Nishigotanda, Tokyo Parts Ward [Telephone: 13 (3491) 3181] Column 7 of "3. Detailed Description of the Invention" of the specification subject to the amendment. Contents of the amendment are as shown in the attached sheet (other than the matters stated in the column subject to the amendment, Table 1 on page 36 of the specification subject to the amendment Correct as shown in the attached sheet.

Claims (3)

[Claims] (1) The following general formula [I] (R_1)_xC(CH_2OCOOR_2)_y...
・[I] [In the formula [I], R_1 is a methyl group,
R_2 is each independently a hydrocarbon group having 30 or less carbon atoms or a hydrocarbon group having an ether bond having 2 to 30 carbon atoms, x is an integer of 0 to 2, and y is 2
is an integer of ~4]. (2) The following general formula [I] (R_1)_xC(CH_2OCOOR_2)_y...
・[I] [In the formula [I], R_1 is a methyl group,
R_2 is each independently a hydrocarbon group having 30 or less carbon atoms or a hydrocarbon group having an ether bond having 2 to 30 carbon atoms, x is an integer of 0 to 2, and y is 2
A lubricating oil characterized by being made of a polycarbonate represented by: (3) The following general formula [I] (R_1)_xC(CH_2OCOOR_2)_y...
・[I] [In the formula [I], R_1 is a methyl group,
R_2 is each independently a hydrocarbon group having 30 or less carbon atoms or a hydrocarbon group having an ether bond having 2 to 30 carbon atoms, x is an integer of 0 to 2, and y is 2
An insulating oil characterized by being made of polycarbonate represented by the following formula: an integer of ~4.