JPS61124960A - Preparation of binder resin - Google Patents

Abstract

PURPOSE:To obtain the binder resin of developer prevented from offset and fixable at lower temp. by reacting an alcohol having >=2 OH groups and a tertiary amino group and/or an epoxy group having a tertiary amino group in preparing a vinyl polymer from a specified monomer. CONSTITUTION:(a) The alcohol having >=2 OH groups and a tertiary amino group and/or an epoxy group having a tertiary amino group are allowed to react in polymerizing (b) styrene and/or its deriv. and (c) one selected from methacrylic acid, acrylic acid, and their ester. A preferable component of (a) is said alcohol represented by formula [I]-[IV] and its is used in an amt. of 0.05-50wt% of the total weight of the monomers and not above the amt. of (a) by molar basis. The component (a) may be reacted with the component (c) before the polymerization and during or after it with the component (c) not polymerized or polymerized.

Description

[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to a method for producing a binding resin, and more specifically, for developing an electrostatic image in electrophotography, electrostatic recording, electrostatic printing, etc. The present invention relates to a method for producing a binding resin used in a developer composition.

[Conventional technology and problems]

As a conventional electrophotographic method, as described in U.S. Patent Nos. 2,297,691 and 2,357,809, etc.
A photoconductive insulating layer is uniformly charged, the layer is then exposed to light, and the charge on the exposed portions is dissipated to form an electrical latent image, which is then coated with a colored pigment called toner. After the visible image is transferred to a transfer material such as transfer paper (transfer process), it is heated,
It consists of a step of permanently fixing (fixing step) by pressure or other suitable fixing method.

In this way, toner is used not only in the development process but also in the transfer process.
It must have the functions required in each step of the fixing process.

Generally, toner is subjected to mechanical frictional force due to shearing force and impact force during mechanical operation in a developing device, and deteriorates during copying of tens to tens of thousands of sheets. To prevent such toner deterioration, it is best to use a strong resin with a large molecular weight that can withstand mechanical friction, but these resins generally have a high softening point and are suitable for non-contact fixing methods such as oven fixing and infrared fixing. With radiant fixing, the thermal efficiency is poor, so fixing is not sufficient.Also, since the contact fixing method has good thermal efficiency, even in the widely used heat roller constant fixing method, it is necessary to use the heat roller to achieve sufficient fixing. It becomes necessary to raise the temperature, which not only causes adverse effects such as deterioration of the fixing device, curling of paper, and increased energy consumption, but also causes a significant drop in production efficiency when producing toner by pulverizing such resins. descend. Therefore, it is not possible to use a binder resin (binding resin) whose polymerization degree and even softening point are too high.

On the other hand, in the heat roller fixed fixing method, the heating roller surface and the toner image surface of the fixing sheet come into pressure contact, so the thermal efficiency is extremely high, and it is widely used from low speeds to high speeds.
When the heating roller surface and the toner image surface come into contact, a so-called offset phenomenon tends to occur, in which the toner adheres to the heating roller surface and is transferred to a subsequent transfer paper or the like. To prevent this phenomenon, the surface of the heating roller is treated with a material with excellent mold release properties such as fluorine-based resin, and in addition, a mold release agent such as silicone oil is applied to the surface of the heating roller to completely prevent the offset phenomenon. are doing.

However, the method of applying silicone oil etc.
This is not preferable because the fixing device becomes large, which not only increases cost but also makes it complicated, which tends to cause trouble.

In addition, as described in Japanese Patent Publication No. 55-6895 and Japanese Patent Application Laid-open No. 56-98202, there is a method to improve the offset phenomenon by widening the molecular weight distribution width of the binder resin, but the degree of polymerization of the resin increases and the fixation becomes difficult. The temperature also needs to be high.

As a further improved method, as described in Japanese Patent Publication No. 57-493, Japanese Patent Application Publication No. 50-44836, and Japanese Patent Application Publication No. 57-37353, the offset phenomenon is improved by making the resin asymmetrical and crosslinking. There is a method, but the fixation point has not been improved.

Generally, the minimum fusing temperature is between the cold offset (cold offset) and hot offset, so the usable temperature range is between the minimum fusing temperature and the hot offset. By raising the offset temperature as much as possible, the fixing temperature used can be lowered and the usable temperature range can be expanded, resulting in energy savings, high-speed fixing, and prevention of paper curl. In addition, since double-sided copying can be performed without trouble, there are many advantages such as making the copying machine more intelligent, controlling the temperature of the fixing device more accurately, and relaxing the tolerance range.

Therefore, resins and toners with good fixing properties and offset resistance are always desired.

In addition, when using a styrene-based binder resin to achieve such requirements, Japanese Patent Application Laid-Open Nos. 49-65232 and 1972
As described in No. 0-28840 and JP-A No. 50-81342, methods of adding paraffin wax, low molecular weight polyolefin, etc. as offset inhibitors are known, but if the amount added is small, it is ineffective, and if the amount is too large, it is It has been confirmed that the developer deteriorates quickly, and in the case of polyester resin, even if the above-mentioned anti-offset agent is applied, it has little effect, and that the more the amount used, the faster the developer deteriorates.

Polyester resin inherently has good fixing properties, and can be sufficiently fixed even in a non-contact fixing method, as described in U.S. Pat. It was difficult to use.

As described in JP-A-50-44836, JP-A-57-37353, and JP-A-57-109875, polyester resins with improved anti-offset properties using polyhydric carboxylic acids have sufficient properties for use. Those that do not have anti-offset properties, or those that do, not only sacrifice the low-temperature fixing properties inherent to polyester resins, but also
Even in the toner production process, the crushability was extremely poor, and there were also problems in developer production.

Generally, a toner is composed of a binder resin, a colorant, and other additives, with the binder resin being the main component. As toner binder resin, coumarone indene resin,
Terpene resin, styrene resin or their copolymer resin,
Polyester resins, epoxy resins, and the like are generally used, but there are few binder resins that are strongly positively charged by friction. In order to make a toner positive polarity, it is generally known to add additives such as nigrosine dye as a charge control agent, but this method has poor compatibility with the binder resin that constitutes the main component of the toner. If the particles are mixed for a long time in the developing device, the particles will be destroyed, and if nigrosine etc. is simply dispersed, particles with the opposite (negative) polarity that do not contain nigrosine etc. will be generated and there will be no image signal. A so-called smearing phenomenon occurs in which toner adheres to certain places.Furthermore, when nigrosine dyes are used, the amount of charge changes depending on the humidity of the environment due to their hydrophilic properties, resulting in a decrease in image quality.Furthermore, nigrosine dyes In general, there are drawbacks such as strong coloring and incompatibility with color toners.From the above, it is strongly positively charged,
It is desired to develop toner binder resins and toners that are not affected by environmental humidity and have excellent durability.

The present invention has been made to meet these demands, and its purpose is to provide a developing device that can prevent off-set (without applying an anti-offset liquid) in a heat roller constant fixing method and that can be fixed at a lower fixing temperature. The purpose of the present invention is to provide a binding resin for use in adhesives.

Another object of the present invention is to provide a binder resin for a developer that can prevent offset without adding an offset inhibitor in a heat roller fixed fixing method and can fix at a lower fixing temperature. .

Another object of the present invention is to provide a binder resin for a developer that has good fluidity, does not cause blocking, and has a long life (hard to deteriorate).

Another object of the present invention is to provide a binder resin for a developer that exhibits good wire crosstalk and pulverization properties during the production of the developer.

Another object of the present invention is to provide a dry developer for electrophotography,
The object of the present invention is to provide a toner that forms clear and fog-free images by using a toner binder resin that inherently has a strongly positive charging property, and more specifically, to provide a toner that is resistant to the influence of environmental humidity and that improves the above-mentioned drawbacks. The object of the present invention is to provide a toner which is extremely small and has excellent durability, and whose binder resin essentially has positive triboelectric charging properties.

Another object of the present invention is to provide a clear color developer with good transparency.

[Means for solving problems]

The present inventors have arrived at the present invention as a result of intensive research to achieve the above object.

That is, the present invention provides (c) when producing a vinyl polymer from (a) styrene and/or styrene derivatives and (b) one or more monomers selected from methacrylic acid, acrylic acid, and esters thereof. The present invention relates to a method for producing a binding resin characterized by reacting a dihydric or higher alcohol having a tertiary amino group and/or an epoxy compound having a tertiary amino group.

In the present invention, from the viewpoint of the use of the binding resin, it is preferable that the component (c) above has the following general formulas (I) to (r
V) is a dihydric or higher alcohol having a tertiary amino group, and the amount used is 0.0 based on the total amount of monomers.
5 to 50% by weight, and the number of moles used does not exceed the number of moles of component (b).

X-R.

Demon HO4s-N-Ry-OH・・・・・・(If)X-R
z X-R+z HO-Rs, -N-Rw NR+. -OH...
... (III) Ls (In formulas (1) to (IV), Rt+ Rz+ Rst R
ht Rt+R111R9, R1゜+ RII+ RI
2+ R131R1#l R111 has 1 to 1 carbon atoms
5 is an alkylene group, R3 and R4 are an alkyl group having 1 to 10 carbon atoms, R17+ R111 is an alkyl group having 1 to 4 carbon atoms, and R1? and RIB may form a heterocyclic ring of the same nitrogen atom. Indicates RIS. X represents a hydrogen atom or a hydroxyl group. ) More preferably, the above resin has a softening temperature of 100 to 100 using a Koka type flow tester.
160°C, and the glass transition temperature is 50°C or higher.

In the present invention, component (c) may be reacted with component (b) before polymerization, or may be reacted with component (a) and (b).
The reaction may be carried out after or during the polymerization of the components.

In the present invention, the polymerization reaction mainly proceeds by generally known vinyl polymerization, in which case a polymerization initiator such as a peroxide or preferably an azo compound is used, and a reaction suitable for the monomers and initiator used as appropriate. Condition is selected.

Examples of the styrene or styrene derivative (a) in the present invention include styrene, 0-methylstyrene, m
-Methylstyrene, p-methylstyrene, α-methylstyrene, p-ethylstyrene, 2,4-dimethylstyrene, p-n-butylstyrene, p-tert-7'
Tylstyrene, p-n-hexylstyrene, p-n-octylstyrene, p-n-nonylstyrene, p-n-decylstyrene, p-n-dodecylstyrene, p-methoxystyrene, p-phenylstyrene, p- Mention may be made of chlorstyrene, 3,4-dichlorostyrene, and others.

Examples of (b) methacrylic acid, acrylic acid, or esters thereof include acrylic acid, methyl acrylate, ethyl acrylate, AcryJL [n-propyl, isofurovir acrylate, n-butyl acrylate, isobutyl acrylate, acrylic tert-butyl acid, amyl acrylate, cyclohexyl acrylate, n acrylate
-Octyl, isooctyl acrylate, decyl acrylate, lauryl acrylate, 2-ethylhexyl acrylate, stearyl acrylate, methoxyethyl acrylate, 2-hydroxyethyl acrylate, hydroxypropyl acrylate, glycidyl acrylate, 2- acrylate
Chlorethyl, phenyl acrylate, methyl α-chloroacrylate, methacrylic acid, methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, isopropyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, tert-butyl methacrylate , amyl methacrylate, cyclohexyl methacrylate, n-octyl methacrylate, isooctyl methacrylate, decyl methacrylate, lauryl methacrylate, 2-ethylhexyl methacrylate, stearyl methacrylate, methoxyethyl methacrylate, 2-hydroxyethyl methacrylate, methacrylate Examples include hydroxypropyl acid, glycidyl methacrylate, phenyl methacrylate, dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate, and others.

Further, as the dihydric or higher alcohol having a tertiary amino group represented by the general formulas CI) to (IV) in (c) in the present invention, the following may be mentioned.

(1) Alcohol N, N represented by general formula (r)
'-Bis(hydroxymethyl)piperazine, N, N'-
Bis(hydroxymethyl)methylpiperazine, N, N'
-bis(2-hydroxyethyl)piperazine, N, N'
-bis(2-hydroxypropyl)piperazine, N,
N'-bis(2-hydroxypropyl)-2,5-dimethylpiperazine, N,N'-bis(2-hydroxyethyl)-2,5-dimethylpiperazine, N,N'-bis(2-hydroxy- 2-methylpropyl)piperazine,
N,N'-bis(2-methyl-2-hydroxynonyl)piperazine, N,N'-bis(2-hydroxy-3-
methoxylpropyl) piperazine, N, N'~bis(
3-phenyl-2-hydroxypropyl)piperazine, etc.

(2) Alcohol represented by the general formula (fil) N, N-bis(2-hydroxyethyl)methylamine, N, N~bis(2-hydroxyethyl)cyclohexylamine, N
, N-bis(2-hydroxypropyl)methylamine,
N,N-bis(2-hydroxypropyl)isopropylamine, triethanolamine, etc.

(3) Alcohol N represented by general formula (III), N
'-dimethyl-N, N'-bis(2-hydroxyethyl)ethylenediamine, N,N'-dicyclohexyl-
N,N'-bis(2-hydroxyethyl)hexamethylenediamine, N,N'-diethyl-N,N'-bis(2-hydroxypropyl)ethylenediamine, N,N
'-dibutyl-N.

N-bis(2-hydroxypropyl)pentamethylenediamine, etc.

(4) Alcohol represented by general formula (IV) 2-methyl-2-N, N-dimethylamythyl-1,3-propanediol, 2-methyl-2-N, N-diethylaminomethyl-1, 3-propanediol, 2-ethyl-
2-N,N-di-n-propylaminomethyl-1,3-
Propanediol, 2-methyl-2~N, N~di-n-
Butylaminomethyl-1,3-propanediol, 2-
Methyl-2-N,N-dimethylaminoethyl-1,3-
Propanediol, 2-Methyl-2-piperidinomethyl-1,3-propanediol, Bis(2-N,N-dimethylaminomethyl)-1,3-propanediol, Bis(2-N,N-di-isopropylamino methyl)-1,
3-propanediol, 3-methyl-3-N, N-dimethylaminomethyl-1,5-bentanediol, 3-methyl-3-N, N-diethylaminemethyl-1,5-bentanediol, 4-ethyl- 4-N,N-diisopropylaminomethyl-1,6-hexanediol and the like.

Examples of the epoxy compound having a tertiary amino group include the following.

Among the components constituting the binding resin according to the present invention, (a) styrene or styrene derivative forms the main skeleton of the resin, and (b) (meth)acrylic acid or its ester is used to maintain the temperature of the resin at a temperature such as the softening point. The component (c) is a component that determines the charge and adjusts the amount of charge, lowers the fixing temperature, and improves offset resistance. There is no effect if it is less than 0.05% by weight,
If it exceeds 50% by weight, the moisture resistance of the toner will deteriorate.

In addition, the softening point of the resin of the present invention using a Koka type flow tester is 10.
The temperature is preferably 0 to 160°C; if it is too low, the offset resistance will be insufficient, and if it is too high, the fixing property will be insufficient.

The method for producing the binding resin of the present invention is carried out by a well-known addition polymerization reaction.

Coloring agents used in conjunction with the binder resin of the present invention to form a developer include carbon black, acetylene black, phthalocyanine blue, permanent brown FC, brilliant first scarlet, pigment green B10-Damine-B base, and solvent red 49. , Solvent Red 146, Solvent Blue 35, and mixtures thereof.
About 1 to 15 parts by weight is used per 100 parts by weight of the binding resin.

When making a magnetic toner using the binding resin according to the present invention, examples of the magnetic material include alloys or compounds containing elements exhibiting ferromagnetism such as ferrite and magnetite, and the magnetic material has an average particle size of 0. It can be used in the form of a fine powder of .1 to 1 .mu.m dispersed in a binding resin in an amount of 40 to 70% by weight.

Known property improving agents contained in toner include charge control agents, anti-offset agents, fluidizing agents, etc., but since the resin of the present invention has good properties by itself, these agents may not be used during toner preparation. It becomes unnecessary to add a property improver, or even if it is added, only a small amount is required.

〔Example〕

Examples of the invention will be described below, but the invention is not limited to these examples. It should be noted that all composition ratios shown in Examples are expressed in parts by weight.

Example 1 500 parts of xylene, N,
N'-bis(2-hydroxypropyl)piperazine 50
1 part and 2 parts of dibutyltin oxide, and the temperature was adjusted to 80°C. A mixed solution of 820 parts of styrene, 130 parts of n-butyl acrylate, and 10 parts of α,α”-azobisisobutyronitrile was dropwise polymerized in a nitrogen stream over 4 hours. After the dropwise addition was completed, the mixture was kept at the same temperature for 10 hours. After aging, the temperature was gradually raised to 210°C while the pressure was reduced to 2 mmHg, the xylene was distilled off, and the molten resin was taken out into a stainless steel vat, left to cool, and pulverized. Flow tester softening point 126.0℃, Tg 62.0℃
) was obtained. This softening point was determined by heating a 1 cm3 sample using a Koka type flow tester (manufactured by Shimadzu Corporation) at a temperature increase rate of 6°C/min, and applying a pressure of 20 kg/cm2 with a plunger.
Applying a load of The temperature corresponding to /2 is taken as the softening point.

After mixing 93 parts of the resin and 7 parts of carbon black (SU-GAL 400R manufactured by CABOSOTO) in a ball mill, coarsely pulverize it in a hammer mill, finely pulverize it in a jet mill, and classify it, a toner having an average particle size of 13.5 μm was prepared. Obtained. The obtained toner was mixed with carrier iron powder (manufactured by Nippon Tetsuko Co., Ltd., EFV 200).
/300), and the amount of charge was measured using a blow-off measuring device and found to be +19 μc/g.

A developer was prepared by mixing 91 g of the toner with 1209 g of carrier iron powder, and a commercially available electrophotographic copying machine (the photoreceptor was an organic photoconductor, the fixing roller had a diameter of 60 mm, and the rotation speed was 2
55 mm/sec, the temperature of the heat roller in the fixing device was made variable and the oil application device was removed), and a clear image was obtained with no background smudges, smearing, or missing black areas. Obtained.

When the fixing temperature was controlled at 140 DEG C. to 220 DEG C. and the image fixability and offset property were evaluated, the image was sufficiently fixed at 150 DEG C. and no hot offset or gutter occurred. When images were printed up to 50,000 sheets, clear images were obtained without any visible blurring or missing solid black areas.

The minimum fixing temperature here is 15 mm x 7.5 mm on the bottom.
A load of 500 g was placed on an n+m sand eraser, and the image fixed through the fixing machine was rubbed back and forth 5 times, and the optical reflection density was measured using a Macbeth reflection densitometer before and after rubbing.
It refers to the temperature of the fixing roller when the fixing rate exceeds 70% as defined below.

Example 2 500 parts of xylene and 20 parts of triethanolamine are charged into the reactor of Example 1, and the temperature is adjusted to 80°C. Under a nitrogen stream, 790 parts of α-methylstyrene, 10 parts of acrylic acid, 180 parts of 2-ethylhexyl acrylate and α
, α゛-Azobisdimethylwareconitrile (20 parts) was dropwise polymerized over 4 hours. After aging at the same temperature for 10 hours after the dropwise addition, the temperature was gradually raised to 210°C while the pressure was reduced to 2 mmHg, xylene was distilled off, and the molten resin was taken out into a stainless steel vat, left to cool, and pulverized to form a powder. Resin (Koka type flow tester softening point 124
．． 5° C., Tg 65.0”c) was obtained.

After mixing 93 parts of the resin and 7 parts of carbon black (SU-GAL 400R manufactured by Capot Co., Ltd.) in a ball mill,
It was crushed and classified to obtain a toner with an average particle size of 13.2 μm. The amount of charge of the obtained toner was +15 μc/g.

A developer was prepared by mixing 91 g of the toner with 1209 g of carrier iron powder, and an image was produced using the same evaluation machine as in Example 1. A clear image was obtained without background smudges, bleeding, or missing solid black areas. It was done. When the fixing temperature of the fixing device was controlled and the image fixability and offset property were evaluated, the result was 1.
It was fixed at 48° C. and no hot offset occurred.

When images were printed up to 50,000 sheets, clear images were obtained without any visible blurring or missing solid black areas.

Example 3 In the reactor of Example 1, 500 parts of xylene, 15 parts of N,N'-dimethyl-N,N'-bis(2-hydroxyethyl)ethylenediamine, 840 parts of styrene, and 1 part of methacrylic acid were added.
0 parts, butyl acrylate 135 parts and α.

Using 10 parts of α゛-azobisdimethylwareconitrile, a powdered resin (softening point 123.0°C, Tg 63.2°C using Koka type flow tester) was prepared in the same manner as in Example 1.
I got it.

After mixing 93 parts of the resin and 7 parts of carbon black (Su-Gal 400R manufactured by Capoft) in a ball mill, kneading,
Grind and classify, average particle size: 13. A toner of oμ was obtained. The amount of charge of the obtained toner was +14 μc/g. 91 g of the toner was mixed with 1209 g of carrier iron powder,
When a developer was prepared and an image was produced using the same evaluation machine as in Example 1, a clear image was obtained without background smudges, bleeding, or missing solid black areas.

Controls the fixing temperature of the fixing device to improve image fixability,
When evaluating the offset property, it was fixed at 145℃,
No hot offset occurred. When images were printed up to 50,000 sheets, clear images were obtained with no visible defects or omissions in solid black areas.

Example 4 In the reactor of Example 1, 500 parts of xylene, 2-methyl-2
Using 15 parts of -N,N-dimethylaminomethyl-1,3-propanediol, 855 parts of styrene, 10 parts of methacrylic acid, 120 parts of lauryl methacrylate, and 10 parts of α,α゛-azobisdimethylwareconitrile, Example 1
A powdered resin (softening point of Koka type flow tester: 123.6°C, Tg: 62.3°C) was obtained in the same manner as above.

After mixing 93 parts of the resin and 7 parts of carbon blank (Su-Gal 400R manufactured by Cabot) in a ball mill, kneading,
It was crushed and classified to obtain a toner with an average particle size of 13.2 μm.

The amount of charge of the obtained toner was +16 μc/g.

Mixing 91 g of the toner with 1209 g of carrier iron powder,
When a developer was prepared and an image was produced using the same evaluation machine as in Example 1, a clear image was obtained without background smudges, smearing, or missing solid black areas.

Controls the fixing temperature of the fixing device to improve image fixability,
When evaluating the offset property, it was fixed at 144℃,
No hot offset occurred (no force). When images were printed up to 50,000 images, clear images were obtained without any visible distortion or loss of evening parts to black.

Example 5 In the reactor of Example 1, 500 parts of xylene, 13 parts of the following epoxy compound, 837 parts of styrene, 10 parts of acrylic acid, 140 parts of butyl acrylate, and 20 parts of α,α°-azobisdimethylwareconitrile were used. Then, in the same manner as in Example 1, a powdered resin (softening point 125.4°C using Koka type flow tester) was prepared.
, Tg 65.2°C).

After mixing 93 parts of the resin and 7 parts of carbon black (Su-Gal 400R manufactured by Cabot) in a ball mill, kneading,
It was crushed and classified to obtain a toner with an average particle size of 13.7 μm. The amount of charge of the obtained toner was +16 μc/g. 91 g of the toner was mixed with 1209 g of carrier iron powder,
When a developer was prepared and an image was produced using the same evaluation machine as in Example 1, a clear image was obtained without background smudges, bleeding, or missing solid black areas.

Controls the fixing temperature of the fixing device to improve image fixability,
When evaluating the offset property, it was fixed at 146℃,
No hot off cents occurred. When images were printed up to 50,000 sheets, clear images were obtained without any visible blurring or missing solid black areas.

Comparative Example 1 Resin (Koka flow tester softening point 128.4"C, Tg
66.0°C) was obtained.

After mixing 93 parts of the resin and 7 parts of carbon black (SU-GAL 400R manufactured by Capot Co., Ltd.) in a ball mill, kneading,
Grind and classify, average particle size: 13. A toner of Oμ was obtained. When the obtained toner was mixed with carrier iron powder and the amount of charge was measured using a blow-off measuring device, it was found to be -7 μc/g.

Claims (1)

[Scope of Claims] 1 (a) styrene and/or styrene derivative;
(b) When producing a vinyl polymer from one or more monomers selected from methacrylic acid, acrylic acid, and esters thereof, (c) a dihydric or higher alcohol having a tertiary amino group and/or a tertiary 1. A method for producing a binding resin, which comprises reacting an epoxy compound having a class amino group. The component 2(c) is a dihydric or higher alcohol having a tertiary amino group represented by the following general formulas [I] to [IV], and the amount used is 0.2 or more based on the total amount of monomers.
05 to 50% by weight, and the number of moles used does not exceed the number of moles of component (b). ▲There are mathematical formulas, chemical formulas, tables, etc.▼……[I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼……[II] ▲There are mathematical formulas, chemical formulas, tables, etc.▼……[III] ▲Mathematical formulas, chemical formulas, There are tables, etc.▼...[IV] (In formulas [I] to [IV], R_1, R_2, R_5, R
_6, R_7, R_8, R_9, R_1_0, R_1_
1, R_1_2, R_1_3, R_1_4, R_1_6
, is an alkylene group having 1 to 15 carbon atoms, R_3, R_
4 is an alkyl group having 1 to 10 carbon atoms, R_1_7, R
_1_8 represents an alkyl group having 1 to 4 carbon atoms, R_
1_7 and R_1_8 may form a heterocyclic ring of the same nitrogen atom, and R_1_5 represents an alkyl group having 1 to 3 carbon atoms or ▲There is a numerical formula, chemical formula, table, etc.▼. X
represents a hydrogen atom or a hydroxyl group. ) 3 The softening temperature of the resin using a high-performance flow tester is 10.
The manufacturing method according to claim 1, wherein the temperature is 0 to 160°C, and the glass transition temperature is 50°C or higher.