WO1991018060A1

WO1991018060A1 - Organic surface treatment

Info

Publication number: WO1991018060A1
Application number: PCT/JP1991/000647
Authority: WO
Inventors: Kazushi Miyata; Shouji Saibara; Tomohiro Harada
Original assignee: Hitachi Maxell, Ltd.
Priority date: 1990-05-16
Filing date: 1991-05-16
Publication date: 1991-11-28
Also published as: DE4191067T

Abstract

An organic surface treatment which has a number-average molecular weight of 300 or above and a chain skeleton based on carbon and hydrogen and having an affinity for solvents, said skeleton having at least two side chains containing ester, ether, ketone or phenyl groups and at least one terminal of said skeleton being a hydrophilic or reactive functional group. It can improve the dispersibility of inorganic material in solvents, when used as a surface treatment or dispersant therefor.

Description

Harm

Organic surface treatment agent

Technical field

The present invention relates to an organic surface treating agent. That is, as an inorganic material, in particular, a surface treatment agent and dispersant for inorganic powders in general, an organic surface treatment agent suitable for treating the surface of the inorganic powder to improve dispersibility in a solvent. The purpose is to provide

Technique

In general, the surface of inorganic materials and inorganic powders are hydrophilic, so they are poorly dispersed and dispersible in organic solvents and polymer binders. In manufacturing, the surface modification of inorganic materials and inorganic powders with silane coupling agents has been studied (Chemical review).

No. 4 4 “Surface modification” (edited by the Chemical Society of Japan), the dispersibility of this inorganic powder is particularly important in the production of magnetic paints. It is. The recording density of magnetic recording media made using this is dispersive. This is because it is directly related to.

Therefore, even in the field of magnetic paints, at least one or more lipophilic molecular skeletons must be used as a dispersant in order to improve the dispersibility of magnetic powders and boilers. Based on the basic idea that dispersibility can be improved by having a hydrophilic or reactive functional group at the end, fatty acids and various surfactants have been conventionally surface-treated. These powders can be used as an agent to treat these powders (Japanese Patent Application Laid-Open No. 58-102004),

Surface modification with 'one' coupling agents has been carried out (Japanese Patent Application Laid-Open Nos. 55-125, 139 and 56-58, 135). Gazette).

On the other hand, toluene, MEK, ethyl acetate, THF and the like are used as organic solvents for dissolving organic substances. Ethyl acetate contains an ester group, THF contains an ether group, Μ Ε contains a ketone group, and toluene contains a phenyl group.

However, conventional fatty acid-silane coupling agents, etc., have an ester group, ether group or phenyl group in the molecular skeleton. Including Therefore, it has poor affinity with these organic solvents.

Furthermore, since these fatty acid-silan coupling agents have a very small average molecular weight, the separation between inorganic powders cannot be separated. For this reason, the inorganic powders that have been dispersed with great effort eventually re-aggregate. Therefore, these fatty acids (silan kabu bling) were insufficient to stably disperse the inorganic powder in the presence of the organic solvent.

On the other hand, hydrophilic or reactive functional groups such as sulfonic acid groups, phosphoric acid groups, carboxylic acid groups and their salts and tertiary amino groups are added to the δί molecular binder inside the molecular chain. Attempts have been made to enhance the dispersibility of the inorganic powder in the binder itself by incorporating it into the binder (Japanese Patent Application Laid-Open Nos. Sho 56-13520 and Sho 55-111). 773 34, Japanese Patent Application Laid-Open (JP-A) No. 1132322, etc.), however, the dispersion is still insufficient, and the emergence of a new surface treatment method for improving the dispersibility has been desired.

This invention solves the inadequacy of the conventional surface treatment technology described above, and secures a molecular size large enough to separate the powders from each other and to sleep. At the same time, by arranging a hydrophilic or reactive functional group at the end of the molecular chain to maximize the function of the hydrophilic or reactive functional group, An object of the present invention is to provide an organic surface treating agent which exhibits an excellent surface treating effect in a small amount.

Disclosure of the invention

Therefore, the present inventors have conducted intensive studies to further improve the surface treatment effect, and as a result, firstly, a sulfonate group, a phosphate group, a force boronate group, and Secondly, a hydrophilic or reactive functional group such as a salt and a tertiary amino group is introduced into the molecular terminal. Second, the number average molecular weight is 800 or more, preferably 250 Control within 0, more preferably within a range of 1500 to 10000, and thirdly, in the chain of the molecular skeleton, an ester group, an ether group, or a keto group. By arranging two or more side walls containing a thiol group or a fluorinated group, the surface modification effect of inorganic materials, particularly inorganic powders, can be significantly enhanced. It has been found that a treatment agent can be provided.

The reason for this is that hydrophilic or reactive functional groups introduced at the molecular ends are not absorbed. Adsorbs or reacts to the surface of the inorganic material as a deposition anchor. The adsorbed or reacted molecules are arranged as if they were drawn, and the surface was changed from hydrophilic to lipophilic, and more particularly to organic solvent, significantly improving the dispersibility of the powder. It is thought that this is due to this.

The was hydrophilic or as a reactive functional group, one COOX, One OH, one N Hs, One NH ₂ R, One NRR ', One _{NH 3 +, - NH aR +} > one NHRR, +, One NRR, R "+, one S 0 ₃ X, one 0 S 03 X, one 0 P (0), (0 X) ₂ , one 0 P (0). (0 X) (0 R), one OP (0) (OR) ₂ , one P (0) (OX) ₂ , one P (0) (OX) (OR), one P (0) (0R) 2, one Si (0R) ₃ , one S i R (0 R,) 2 , one N = C = 0, your good beauty one CH (0) Chi sales of CH _2, either (provided, however, X = H or a metal, R, R ,, R "= Al key Lumpur based on Ru der) or it selected and structure Oh Ru Ru this is Nozomu or tooth rather, one COOX, one _{NH 2, - NHR, - NRR} ,, - S O.sX, - 0 S 0 ₃ X, -0 P (0) (0 X) ₂ , -P (0) (0 X) ₂ ,-S i (0 R) ₃ , -S i R (0 R ') ₂ , and One of CH (0) CH ₂ (where X = H or metal, R and R '= an alkyl group) are more preferable.

In addition, a chain-like skeleton, in which the side chain contains one C 00 H, one H, one NH ₂ , one NHR, one NRR, one CH (0) CH ₂ , and an ammonium salt By including any one of these (provided that R, R, and = alkyl group>), the surface modification effect can be further enhanced.

The method for synthesizing this kind of organic substance is not particularly limited. For example, the polymerization may be carried out using a polymerization initiator having a hydrophilic functional group such as COOH, A macromonomer method using a chain transfer agent having a hydrophilic or reactive functional group may be used.

As the polymerization initiator, it is possible to use, for example, nana, benzobisisobutyl nitrile, benzoyl peroxide, etc., and as a chain transfer agent. Thioglycerin, thioglycolic acid, sodium salt of 21-mercaptoethanesulfonate, mel-butobenzo You can use a tier or something. BEST MODE FOR CARRYING OUT THE INVENTION

Hereinafter, specific examples of the present invention will be described, but the present invention is not limited to these examples.

<< Synthesis of surface treatment agent >>

Example '1

Meta-metal creel 0.9-mol overlap part α-azobisisobutyronitrile 0.01-mol weight part o-glycerin 0.0 3-mol weight part or more On the basis of 100 parts by weight of the starting material for synthesis, the solvent was

T H F 100 Using 5 parts

The above mixture was placed on a flask equipped with a cooler, and the system was sufficiently purged with nitrogen.Then, the mixture was reacted for 20 hours at 60 with good support. Purified by reprecipitation in petroleum ether and water, and dried under reduced pressure at 60 to 8 hours The number average molecular weight of the obtained organic surface treatment agent was 3.0 X

It was 0 ³ . The introduction of the hydroxyl group was confirmed by NMR and IR.c. The fact that the hydroxyl group was uniformly introduced at the molecular end was not clear. Confirmed by resolution NMR.

As a result, the molecular structure of this organic: surface treatment agent is as follows:

CH-0H

H CHs-C) -S-CH2CHCH2OH

COOCHa

I was able to fix it,

Execution ^ 2

Methyl metal create 0.9 mol weight

2-Hydroxy methyl methacrylate 0.02 mol parts by weight Azobis'sisobutyronitrile 0.01 mol parts by weight Thioglycolic acid 0.03 mol heavy molybdenum The total amount of synthetic starting materials above 100 mol parts

T H F 60 parts by weight

Ethanol 40-fold S section

Was used.

Take the above mixture into a flask equipped with a cooler, and after sufficiently evaporating the system with nitrogen, allow the mixture to react for 20 hours at 60 ° C while thoroughly stirring. Was. The reaction was purified by re-precipitation in petroleum ether and water, then dried under vacuum at 60 and 8 h; The number average molecular weight of the resulting organic surface treatment agent was 3.4xl 0 ³ Tsu der in vapor pressure osmometry. The introduction of hydroxyl groups was confirmed by NMR and IR. In addition, the fact that the carboxyl group was uniformly introduced into the molecular end was confirmed by thin-layer chromatography and high-resolution NMR.

As a result, the molecular structure of this organic surface treatment agent was

CHs CH ₃ C00H H (CH2-C) i- ( CH 2 -C) nS-CHCH 2 C00H i = 31.2 n = 0.7

COOCHs COOCHaCHaOH

It is decided.

Jeongjeong 3

Methyl metal create 0.9 mol parts by weight

2-Hydroxy methyl metal create 0.0 2 mol weight part, etc., azobisisotope port-tril 0.0 1 mol weight part

2—Merubutane tansulfonate sodium salt 0.03 mol parts by weight Synthetic needle S 100

T H F 20 parts by weight

Using 40 parts by weight of ethanol

Transfer the mixture to a flask equipped with a cooler, and thoroughly clean the system. After the substitution, the reaction was carried out at 60 ° C. for 20 hours, with good reaction. During the polymerization, 40 parts by weight of THF was added. The reaction product was re-precipitated in petroleum ether and water to give a crack, and then dried under reduced pressure at 60 to 8 hours. The number average molecule S of the obtained organic surface treating agent was 4.1 × 10 ³ by vapor pressure S transmission method. The introduction of the hydroxyl group was confirmed by NMR and IR. In addition, it was confirmed by thin-layer chromatography and intense-resolution NMR that sodium sulfonate was uniformly introduced into molecular terminals.

As a result, the molecular structure of this organic surface treatment agent is as follows:

CH ₃ CHa

H (CH ₂ one C) Uraraichi (CH ₂ one (n one S one CHsCHsSOaNa Rei = 38 · 3 η = 0.85

C0QCH3 CQOCH2CH2 OH

<

Implementation Kiyoshi 4 METER META CREATE 0.9 mole parts

2-Hydroxyethyl methacrylate 0.02 mol parts by weight, α:, azobisisophthalonitrile 0.01 mol parts by weight Melka Budbenzothiazole 0.035 mol parts by weight Total amount of synthetic starting materials 100 or more 100 parts as solvent for S part

A THF100 overlapping portion was used.

The above mixture was placed in a flask equipped with a condenser, and after sufficiently purging the system with hydrogen, the mixture was reacted at 60 with stirring for 20 hours. The reaction product was purified by reprecipitation in petroleum ether and water, and then dried under reduced pressure at 60 to 8 hours. The number average molecular weight of the obtained surface treating agent was 2.5 × 10 ^{3 by a} vapor pressure infiltration method. The introduction of hydroxyl groups was confirmed by NMR and IR. In addition, it was confirmed by thin-layer chromatography and NMR that the benzothiazole group was uniformly introduced into the molecular terminal. As a result, the molecular structure of the organic surface treatment agent was

CH; CH ₃

H (CH ₂ -C) i- (CH ₂ -C) nSY ι = 22.n = 0.5

COOCHs COOCH2CH2OH Y = benzothiazole group.

Example 5

In Example 2, synthesis was performed using styrene in place of the metal methacrylate, and after the synthesis reaction, an ethanol solution of sodium hydroxide (sodium hydroxide) was used. (0.06 mol parts by weight of um) In addition, purification was carried out in the same manner as described below, and the carbonate at the molecular end was confirmed. The number average molecular weight of the obtained organic surface treatment agent was Tsu ³ .3 Χ 1 0 3 der vapor pressure osmometry c

As a result, the molecular structure of this organic surface treatment agent is

CH ₃ COONa H (CH ₂ -CH) «-(CH ₂ -C) nS-CHCH2CQ0N 颺 = 23 n = 0.65

Z COOCHzCHzOH Z-phenyl group could be determined,

Example 6

After performing the synthesis reaction in Run 1, 0.1 mol of oxidized phosphorus S part was added, and the mixture was stirred at room temperature for 2 days. Next, the organic surface treatment よ was washed well with water c, and then cleaved in the same manner as described above. The number-average molecular location of the resulting organic surface treatment agent is one because at 3.2 chi 1 0 ³ in vapor pressure osmometry 7 _c

The molecular structure of the organic surface treating agent,

CH ₃ 0P (0H) ₂ 0 HCCHs-1 0 CHN_5— CH2 CHCH2-11 0PC0H) ₂ leak = 28 -9

C00CH ₃

I was able to confirm it.

Example 7

Sodium hydroxide was added to the organic surface treating agent obtained in Example 6 in the same manner as in Example 5. Next, the phosphoric acid at the molecular end was identified. 3 obtained in al number average molecular location of the organic surface treatment agent vapor pressure osmometry. OX 1 0 ³ Der As a result, as the molecular structure of this organic surface treatment agent,

_{_{CH 3 - 0P (0Na) 2}} 0 H (CH2-C) «-S-CH ₂ CHCH ₂ 0P (0Na) ₂讕 = 28

COOCHi

_C

Example 8

Methyl methacrylate 0.9 mol parts by weight a-azobisisobutylonitrile 0.01 mol weight S part Chioglycerin 0.0 1 3 mol parts by weight The total amount of the above-mentioned synthesis starting materials is 100 parts by weight.

T H F 100 weight parts

C using

Transfer the above mixture to a flask equipped with a cooler, and after sufficiently purging the system with nitrogen, react the mixture at 60 ° C for 20 hours with good reaction. The residue was purified by reprecipitation in petroleum ether and water, and then dried under reduced pressure at 60 to 8 hours. The number average molecular weight of the obtained organic surface treatment agent is vapor Was Tsu Oh in 5.3 X 1 0 ³ in a pressure osmosis. The introduction of the hydroxyl group was confirmed by NMR and IR. The uniform introduction of hydroxyl groups at the molecular terminals was confirmed by thin-layer chromatography and NMR.

As a result, the molecular structure of the organic surface treatment agent is

CH ₃ QH

H (CH ₂ one C)瓤_ｰS one CHsCHCHsOH邐= 51-9

C00CH;

I was able to confirm

Example 9

Methyl methacrylate 0.9.Mole parts by weight Nanazobisisobutyrononitrile 0.00 7Mole parts by weight Chioglysine 0.00 5 重量 parts by weight The combined amount of the above synthetic starting materials is 100 weights S part ^: as the solvent

T H F 100 weight parts

Was used.

The mixture was placed on a flask equipped with a cooler, and the system was sufficiently purged with nitrogen. After that, the mixture was reacted for 20 hours at 60 ° C. while stirring well. The reaction was re-precipitated in petroleum ether and water and purified, and then heated under pressure at 60'C for 8 hours. The resulting number average molecular organic surface treatment agent was 8.9 X 1 0 ³ Tsu der vapor pressure osmometry. The introduction of hydroxyl groups was confirmed by NMR and IR. In addition, the fact that hydroxyl groups were uniformly introduced into the molecular terminals was confirmed by thin labor chromatography and high-resolution NMR.

CH ₃ 0H

H (CH ₂ one C)鼴_ｰS_CH ₂ CHCH20H蠆= 87 & 9 COOCH:

I was able to confirm

Example 10

Methyl metal create 0.9 乇

2-Hydroxeter Meter Crearate 0.02 Mol by Weight azobisovisobutyronitrile 0.01 Mol by Weight The total amount of synthetic starting materials in an amount of at least 0.33 parts by weight of rubutobrobionic acid is 100 parts by weight.

T H F 0

Take the above mixture into a flask equipped with a cooler, sufficiently purge the system with nitrogen, and then react for 20 hours at 60 with good stirring. The product was purified by reprecipitation in petroleum ether and water, and then heated under reduced pressure at 60'C for 8 hours. The number average molecular weight of the obtained organic surface treatment agent is It was Tsu 3.4 x1 0 ³ Der in pressure osmosis. The introduction of the hydroxyl group was confirmed by NMR and IR. In addition, the fact that the carboxyl group was uniformly introduced into the molecular terminal was confirmed by thin bronze chromatography and NMR with a high resolution.

As a result, the molecular structure of the organic surface treatment agent is as follows:

CH ₃ CH:

F CH C) 韁-CCH2-C) n-S-CH2CH2COOH ι = 32 n = 0.7

CQOCH3 COOCHaCHaQH

Confirmed

Implementation ^ 1 1

Polystyrene 0.9 mol parts by weight, Pazolonitrile 0.01 mol parts by weight

3-Melt Probability Trimetry Sicilane 0.0 3 m With respect to 100 parts by weight of the total amount of the above synthetic starting materials,

100 parts by weight of THF was used.

The above mixture was placed on a flask equipped with a cooler, and the system was sufficiently nitrogen-substituted. Then, the reaction was carried out at 60 "C for 20 hours with sufficient loss. The reaction product was reprecipitated in petroleum ether and water, purified and purified, and then dried under reduced pressure at 60 at 8 hours.The number average molecule of the obtained organic surface treating agent was vapor pressure osmosis. . 5.1 X 1 0 ³ was Tsu der by law or, door Li main door carboxymethyl Shi Li Le group average - Contact Usumayuku Russia Conclusions graph I over is a child that has been introduced into the molecular end to Β was confirmed with high-resolution NMR.

11 ((112-Ji 11 5 _ (; 112 (112 CHs Si (0CH ₃ ) 3 = 42

ZZ = fur base I was able to confirm.

Example 1 2

Methyl metal create 0.9 mol Weight 3: part

2-Hydroxy methyl methacrylate 0.02 mol weight part dimethyl amino methacrylate rate 0.02 mol weight part Zovissovisobutyronitrile 0.01 mol parts by weight Mercaptoprobionic acid 0.03 mol, combined needle of synthetic starting material over 100 parts by weight S 100 As a solvent for parts by weight,

_C using THF 100 parts by weight

The mixture was placed on a flask equipped with a cooler, and after the system was sufficiently nitrogen-substituted, the mixture was reacted for 20 hours at 60 ° C with good agitation. After reprecipitation and refining in petroleum ether and water, it was dried under reduced pressure at 60 ℃ for 8 hours. The number average molecular weight of the obtained organic surface treating agent was 3.7 × 10 ^{3 by a} vapor pressure infiltration method. In addition, the introduction of hydroxyl and amino groups The contents were confirmed by NMR and IR. The uniform introduction of the carboxyl group at the molecular end was confirmed by thin-layer chromatography and high-resolution NMR.

CHs CHs CH ₃

H (CH ₂ -C) i- (CH ₂ -C) n- (CH ₂ -C) 1 -S-CHs CHa C00H Hiring = 33.8

n = 0.75

COOCHa COOCHaCHgOH COO CH ₂ CHa (CH ₃ ) 2 1 = 0.75

The effects of the above two organic surface treatment agents according to the present invention are described below.

First, the surface modification effect of the powder of the present invention will be described by taking titanium oxide as an example.

Application example 1 100 parts by weight of approximately spherical white titanium oxide with an average diameter of 1 am The S part was placed in a three-neck flask with a cooling pipe and a stirrer, and 400 parts by weight of toluene was added. MEK 400 parts After adding the S part, add 2 parts by weight of the organic surface treating agent prepared in Example 1, stir for 2 hours, and then stir well.

I flushed for 3 hours for 8 hours. After standing at room temperature for 2 hours, aging was carried out for 50 hours at 50 * C for 1 hour. Next, the titanium oxide was thoroughly washed.

Applied 2

Instead of the organic surface treating agent produced in Example 1 in the general example 1, the organic surface treating agent produced in Shinjing 2 was used.

Apply 伢 3

Instead of the organic surface treatment agent made in Example 1 in Application Example 1, the organic surface treatment agent produced in Jeongjeong-gil 3 was used.

Reference example 1

In place of the organic surface treatment agent created in Example 1 in Application Example 1, the surfactant surfactant di-sulfo-succinic acid 2-hydroxyethyl salt (trade name a) Yellow OT (manufactured by Nakarai Tesque) was used.

Reference example 2

In place of the organic surface treatment agent made in Example 1 in Example 1 for S, the silane printing agent Octadecyl Triethoxysilane (manufactured by Tipso) Was used.

Reference example 3

In place of the organic surface treatment agent prepared in Example 1 in Application Example 1, a titanium tubing agent trade name TTS (Ajinomoto S) was used.

In addition to the titanium oxide surface-treated in References 1-3 and Reference Examples 1-3, untreated titanium oxide was used as Reference Example 4 to determine the volume of sediment in the solvent. It was set as follows

1.0 s of titanium oxide was placed in a sample tube, and MEK 1008T was added, followed by ultrasonic dispersion for 6 hours. Measured sedimentary ridge after standing for 12 hours c The results are not shown in Table 1

table 1 Settling volume (C discussion 3)

Application example 1 1.3

Application example 2 0.9

Apply 伢 3 0.9

Reference Example 2.7

Reference defeat 2 2.8

Reference Example 33.1

Reference Example 46.2

As described above, according to the organic surface treatment of the present invention, the inorganic powder can be well dispersed. This is evident from the decrease in sedimentation volume in the Eocene. Next, regarding the surface modification effect of the inorganic material according to the present invention, a stainless steel plate whose surface has been thoroughly cleaned (Taking Ra = 0. as an example,

Application example 4

The stainless steel plate contained 1 w% of the organic surface treatment agent synthesized in Example 1. After immersion in MEK solution for 2 hours, aging was performed for 50 to 4 hours. Next, the plate was thoroughly washed with Μ Ε Κ.

Application example 5

Instead of the organic surface treating agent synthesized in Example 1 in Application Example 4, the organic surface treating agent synthesized in Example 3 was used.

Reference example 5

Instead of the organic surface treating agent synthesized in Example 1 in Application Example 4,

The silane coupling agent used in 2 was used.

Reference example 6

Performed in Application Example 4 Reference example instead of the organic surface treatment agent synthesized in ^ 1

Using the titanium coupling agent used in Step 3

In addition to the stainless steel plates surface-treated in 4, 5 and Reference Examples 5 and 6 ', untreated stainless steel 扳 is referred to as Reference Example 7, and water and toluene are used. The contact angle with respect to was measured. Table 2 shows the results.

Table 2 Corrosion angle (

Water toluene

Application example 4 9 0 <2 0

Application example 5 9 5 <20

Reference example 5 1 0 0 6 0

Reference example 6 1 0 5 5 5

Reference defeat 2 0 <20

From the above, it can be seen that the organic surface treating agent of the present invention can improve the surface state of the inorganic material from hydrophilic to organophilic solubility.

Furthermore, the organic surface treatment 5 of the present invention can be used not only in simply changing the surface condition of the inorganic material, but also in a specific industrial product manufacturing process. In particular, the usefulness of the present invention is demonstrated by taking the example of the surface treatment process of ferromagnetic powder in the production of magnetic recording media and magnetic recording media in which ferromagnetic powder needs to be sufficiently dispersed as inorganic powder. Explain <

Reference ^ 8 Sclerosing powder (coercive force of 150 eel stepped, 300 parts by weight saturation magnetization of 120 eiu / g)

PVC, vinegar, beer alcohol, copolymer

(VAGH manufactured by UCC)

Carbon V V 10 parts by weight

Aluminum powder 10 parts by weight

Listitic acid triple-mounting part Stearic acid n-bul 6 parts by weight

Cyclohexanone 3 9 5-fold S part

Toluene 3 9 5 layer S part

The composition having the above composition was mixed and dispersed with sand grinder to produce a magnetic paint. This paint is a polyfunctional isocyanate.

After adding 0 mass parts, apply on a 14 ^ m-thick polyethylene film so that the thickness after dust becomes approximately 2.5-im. After being heated, it was cut into 8 mm widths after the calendar processing to make a group tape. Reference Example 9

Instead of the salt bee vinegar bee vinyl alcohol copolymer (VACGH manufactured by UCC) of Reference Example 8, a vinyl chloride organic surface treatment agent containing sulfuric acid salts and hydroxyl groups (C The magnetic tape was folded in the same manner as in Reference Example 8, except that Kissi Chemical's MR110) was used.

Universal ^ 6

Salted Bee Vinegar Bee Vinyl Alcohol Copolymer (UCC Co., Ltd.) A magnetic tape was prepared in the same manner as in Reference Example 8, except that 60 parts by weight of YAGH manufactured by Japan and 5 parts by weight of the organic surface treating agent synthesized in Example 1 were used.

Application example 7

Vinyl alcohol copolymer (VACC made by UCC) of Reference Example 8 Instead of 65 parts by weight, vinyl chloride copolymer (vinyl alcohol copolymer) VAGH manufactured by UCC) 60 parts by weight of organic surface treating agent synthesized in Example 2. A magnetic table was prepared in the same manner as in Reference Example 8 except that 5 parts by weight was used.

Application example 8

Clay Bee Vinegar B Vinyl Alcohol Copolymer (VACC manufactured by UCC) of Reference Example 8 A magnetic tape was prepared in the same manner as in Reference Example 8, except that 60 parts by weight of VAGH (manufactured by KK) and 5 parts by weight of the organic surface treating agent synthesized in Example 3 were used.

Application example 9

In reference example 8, the clay bee vinegar bee vinyl alcohol copolymer (V.AGH manufactured by UCC) was replaced with 65 parts by weight, and the salt bee bee vinyl alcohol copolymer (UCC A magnetic tape was prepared in the same manner as in Reference Example 8, except that 60 parts by weight of VAGH (manufactured by KK) and 5 parts by weight of the organic surface treating agent synthesized in Example 4 were used.

Application example 1 Reference Example 8 Salt Bee Vinegar Bee Vinyl Alcohol Copolymer (UCC V

(AGH) 65 instead of 5 parts by weight, S-B S-vinyl alcohol copolymer

(VAGH manufactured by UCC) Organic surface treating agent synthesized in 60 parts by weight and in Example 5

A magnetic tape was prepared in the same manner as in Reference 8 except that a five-fold S part was used.

Application example 1 1

-Reference Kiyoshi 8 salt bee vinegar bee vinyl alcohol copolymer (V0GH manufactured by UC0) Instead of 65 parts by weight, salt bee bee vinyl alcohol copolymer

(UCC VAGH) A heavy air tape was prepared in the same manner as in Reference Example 8 except that 60 parts of S part and an organic surface treatment agent synthesized in Jeongjin 6 were used in an amount of 0.5 part by weight.

Application example 1 2

Reference 8 Salt BV vinyl alcohol copolymer (VAGH, manufactured by UCC) 65 Instead of 5 parts by weight, vinyl chloride S-BV alcohol copolymer (UCC) VAGH ) 60 parts by weight and organic surface treatment agent synthesized in Example 7 A magnetic tape was prepared in the same manner as in Reference Example 8 except that 5 parts by weight was used.

Salt bee vinegar bee vinyl alcohol copolymer (VACC manufactured by UCC) of Reference Example 6 UCC S VAGH) Except that 60 parts by weight and the organic surface treating agent synthesized in Example 8 were used.

Reference Example 8 Salty Bee Vinegar Bee Vinyl Alcohol Copolymer (VACC made by UCC) 6 A magnetic tape was prepared in the same manner as in Reference Example 8, except that 60 parts by weight of YAGH manufactured by UCC and 5 parts by weight of the organic surface treating agent synthesized in Example 9 were used.

Defeat 1¾5 Reference Example 8 Salt Bee Vinegar Bee-Bull Alcohol Copolymer (V

(AGH) 6 5-fold In place of S-part, salt bean vinegar be vinyl alcohol copolymer

(UCC Company VAGH) A patch tape was prepared in the same manner as in Reference Example 8 except that 60 overlapping portions and 5 parts by weight of the organic surface treating agent synthesized in Example 10 were used.

For S 伢 1 6

PVC / vinyl alcohol copolymer of Reference Example 8 instead of 65 parts by weight of PVC alcohol copolymer (UCC's VAGH)

(VAGH manufactured by UCC) 60 layers .: Magnetic tapes were prepared in the same manner as in Reference ^ 8 except that part B and the organic surface treating agent synthesized in step 11 were used.

Application example 1 7

Reference Example 8 vinyl acetate vinegar vinyl alcohol copolymer (VACC manufactured by UCC) 6 In place of 5 parts by weight, vinyl alcohol copolymer (vinyl acetate vinegar) SVAGH Organic surface treatment synthesized in 60 parts by weight and practice 1 1 2 A magnetic tape was prepared in the same manner as in Reference Example 8, except that 5 parts by weight of the agent were used.

Each magnetic tape obtained in the above application example was assembled into an 8 mm video cassette, and the chroma SZN ratio, C / N ratio,

RF output was measured. The measurement results are shown in Table 3.

Table 3

Chroma S / N ratio C / N ratio R F output

(dB) (dB) (dB)

Reference Example 8 0 0 0

Reference Example 9 0.6 0.6 0.6 0.4

Application example 6 2. 1 2. 4 1. 9

Application 7 2. 6 2. 9 2. 0

Application example 8 2. 6 2. 4 2. 1

Apply ^ 9 2. 2. 3 1. 8

S example 1 0 2. 9 2. 7 2. 3 Application 伢 2. 8 2. 9 2. 2

Application example 1 2 2.5 2.7 2.0

Application example 1 3 2. 0 2. 3 2.0

Application example 1 4 1 .9 2.2 1 .9

Apply 伢 1 5 2. 5 3. 0 2.0

Application example 1 8 8 2 .. 3 1.7

Application example 1 3. 0 2. 9 2. 3

From the above results, it can be seen that the organic surface treatment ^ of the present invention contributes to the improvement of the dispersibility of the ferromagnetic powder.

Claims

The scope of the claims

1. It has a solvent-soluble chain skeleton whose main component is carbon and hydrogen, and has an ester group, an ether group, and a ketone group in the chain of the skeleton. Is

-Has at least two side chains containing a benzyl group, and at least one terminal of the skeleton is a hydrophilic or reactive functional group, and has a number average molecular weight of 300 or more. An organic surface treatment agent characterized by the following features.

2. The hydrophilic or Tata anti wide functional group is one COOX, One OH, - NH _3, One NH ₂ R, One NRR ', One NH ₃ + one NH ₂ R +, single NHRR' tens - NRR 'R _{"ten, - S 0 3 X, -} 0 S 0 3 X, one 0 P (0) (0 X ) 2, one OP (0) (OX) ( OR), one OP (0) (OR ) ₂ , one P (0) (OX) ₂ , one P (0) (OX) (OR), one P (0) (OR) ₂ , one Si (OR) ₃ , one SiR (OR, Any of 2, 1 N = C-0 and 1 CH (0) CH2 (where X = H or a metal, R, R ', R "= an alkyl group; 2. The organic surface treating agent according to claim 1, wherein the organic surface treating agent has a structure transparent to the organic compound.

3. was hydrophilic or are anti-wide functional groups, one C 00 X, One NH _2, - NHR, One NRR ,, one S OsX, - 0 S 0 a X one _{OP (0) (OX) 2} , one _{P (0) (OX) 2} , one S i (oR) 3, one _{S i R (oR ') 2} , and single CH (0) CH ₂ sac Chi, either (provided that were X = H or The organic surface treatment agent according to claim 2, wherein the organic surface treatment agent has a structure selected from the group consisting of a metal, R, R, and an alkyl group.

4. One C00H, one 0H, one Nt, and one NHR, one NRR, one CH (0) CH2, and one ammonium salt 2. The organic surface treating agent according to claim 1, wherein the organic surface treating agent comprises any one of R, R, and = an alkyl group.

5. The main component is carbon and hydrogen having two or more side chains including an ester group, an ether group, a ketone group or a fluorine group within the skeleton. 2. The organic surface treating agent according to claim 1, wherein, in the solvent-like skeleton, preferably, they are an acrylic resin or a styrene resin.

6. It is characterized in that the number-average molecular arrangement is between 800 and 250

The organic surface treating agent according to claim 1, wherein

7. Characteristic that the number average molecular weight is more than 150 000 and less than 150 000

Claim 8 The organic surface treating agent described in S.