WO1991018060A1 - Traitement organique de surface - Google Patents

Traitement organique de surface Download PDF

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Publication number
WO1991018060A1
WO1991018060A1 PCT/JP1991/000647 JP9100647W WO9118060A1 WO 1991018060 A1 WO1991018060 A1 WO 1991018060A1 JP 9100647 W JP9100647 W JP 9100647W WO 9118060 A1 WO9118060 A1 WO 9118060A1
Authority
WO
WIPO (PCT)
Prior art keywords
organic surface
group
weight
surface treatment
parts
Prior art date
Application number
PCT/JP1991/000647
Other languages
English (en)
Japanese (ja)
Inventor
Kazushi Miyata
Shouji Saibara
Tomohiro Harada
Original Assignee
Hitachi Maxell, Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hitachi Maxell, Ltd. filed Critical Hitachi Maxell, Ltd.
Priority to JP3508965A priority Critical patent/JP3027412B2/ja
Priority to US07/793,382 priority patent/US5357036A/en
Publication of WO1991018060A1 publication Critical patent/WO1991018060A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/14—Derivatives of phosphoric acid
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B5/00—Recording by magnetisation or demagnetisation of a record carrier; Reproducing by magnetic means; Record carriers therefor
    • G11B5/62—Record carriers characterised by the selection of the material
    • G11B5/68—Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent
    • G11B5/70—Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent on a base layer
    • G11B5/712—Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent on a base layer characterised by the surface treatment or coating of magnetic particles
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
    • C09C3/10—Treatment with macromolecular organic compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/04—Sulfonates or sulfuric acid ester salts derived from polyhydric alcohols or amino alcohols or derivatives thereof
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B5/00—Recording by magnetisation or demagnetisation of a record carrier; Reproducing by magnetic means; Record carriers therefor
    • G11B5/62—Record carriers characterised by the selection of the material
    • G11B5/68—Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent
    • G11B5/70—Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent on a base layer
    • G11B5/7013—Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent on a base layer characterised by the dispersing agent

Definitions

  • 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.
  • 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
  • inorganic materials and inorganic powders are hydrophilic, so they are poorly dispersed and dispersible in organic solvents and polymer binders.
  • silane coupling agents have been studied (Chemical review).
  • 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.
  • 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),
  • 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
  • ⁇ ⁇ contains a ketone group
  • toluene contains a phenyl group.
  • 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.
  • 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 ⁇ 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.
  • 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.
  • 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.
  • 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.
  • hydrophilic or reactive functional groups introduced at the molecular ends are not absorbed.
  • 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.
  • 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
  • the surface modification effect can be further enhanced.
  • the method for synthesizing this kind of organic substance is not particularly limited.
  • 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.
  • the polymerization initiator it is possible to use, for example, nana, benzobisisobutyl nitrile, benzoyl peroxide, etc., and as a chain transfer agent.
  • 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
  • Methyl metal create 0.9 mol weight
  • Methyl metal create 0.9 mol parts by weight
  • 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
  • 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 ⁇ 1 0 3 der vapor pressure osmometry c
  • 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.
  • the molecular structure of the organic surface treatment agent is
  • Methyl methacrylate 0.9.Mole parts by weight Nanazobisisobutyrononitrile 0.00 7Mole parts by weight Chioglysine 0.00 5 ⁇ parts by weight
  • the combined amount of the above synthetic starting materials is 100 weights S part ⁇ : as the solvent
  • 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.
  • Methyl metal create 0.9 ⁇
  • 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.
  • the molecular structure of the organic surface treatment agent is as follows:
  • 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 °C 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.
  • 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.
  • 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.
  • the surfactant surfactant di-sulfo-succinic acid 2-hydroxyethyl salt (trade name a) Yellow OT (manufactured by Nakarai Tesque) was used.
  • TTS titanium tubing agent trade name
  • untreated titanium oxide was used as Reference Example 4 to determine the volume of sediment in the solvent. It was set as follows
  • the inorganic powder can be well dispersed. This is evident from the decrease in sedimentation volume in the Eocene.
  • 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 ⁇ ⁇ ⁇ .
  • the silane coupling agent used in 2 was used.
  • the organic surface treating agent of the present invention can improve the surface state of the inorganic material from hydrophilic to organophilic solubility.
  • 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.
  • 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.
  • composition having the above composition was mixed and dispersed with sand grinder to produce a magnetic paint.
  • This paint is a polyfunctional isocyanate.
  • 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.
  • 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.
  • 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.
  • a magnetic tape was prepared in the same manner as in Reference 8 except that a five-fold S part 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
  • VACC made by UCC 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.
  • salt bean vinegar be vinyl alcohol copolymer
  • 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.
  • 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,
  • the organic surface treatment ⁇ of the present invention contributes to the improvement of the dispersibility of the ferromagnetic powder.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Paints Or Removers (AREA)

Abstract

Traitement organique de surface présentant un poids moléculaire numérique moyen égal ou supérieur à 300 et un squelette de chaîne basé sur le carbone et l'hydrogène et possédant une affinité pour les solvants, ledit squelette possédant au moins deux chaînes latérales contenant des groupes ester, éther, cétone ou phényle et au moins une terminaison dudit squelette étant un groupe fonctionnel hydrophile ou réactif. Ce composé permet d'améliorer la dispersibilité de matériaux organiques dans les solvants, lorsqu'on l'utilise en tant que traitement de surface ou en tant que dispersant.
PCT/JP1991/000647 1990-05-16 1991-05-16 Traitement organique de surface WO1991018060A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP3508965A JP3027412B2 (ja) 1990-05-16 1991-05-16 有機表面処理剤
US07/793,382 US5357036A (en) 1990-05-16 1991-05-16 Organic surface-treating agent

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2/126250 1990-05-16
JP12625090 1990-05-16

Publications (1)

Publication Number Publication Date
WO1991018060A1 true WO1991018060A1 (fr) 1991-11-28

Family

ID=14930524

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1991/000647 WO1991018060A1 (fr) 1990-05-16 1991-05-16 Traitement organique de surface

Country Status (2)

Country Link
DE (1) DE4191067T (fr)
WO (1) WO1991018060A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009165910A (ja) * 2008-01-11 2009-07-30 Toyo Ink Mfg Co Ltd 分散剤、及びそれを用いた顔料組成物並びに顔料分散体

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4843366B1 (fr) * 1970-08-19 1973-12-18
JPS50137886A (fr) * 1974-03-29 1975-11-01
JPS5750535A (en) * 1980-09-12 1982-03-25 Toagosei Chem Ind Co Ltd Nonaqueous solvent type dispersant
JPS62265301A (ja) * 1986-05-12 1987-11-18 Nippon Soda Co Ltd シラン変性ブタジエン系重合体及び該重合体を用いた表面処理剤
JPH01210467A (ja) * 1988-02-19 1989-08-24 Dainichiseika Color & Chem Mfg Co Ltd 顔料組成物
JPH01259069A (ja) * 1988-04-08 1989-10-16 Nippon Paint Co Ltd アクリル樹脂で被覆した水性塗料用金属顔料
JPH0216110A (ja) * 1988-05-02 1990-01-19 Ppg Ind Inc アクリル重合体
JPH0291160A (ja) * 1988-09-28 1990-03-30 Dainippon Ink & Chem Inc 熱可塑性樹脂の着色剤用分散剤及びそれを含有する組成物

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4843366B1 (fr) * 1970-08-19 1973-12-18
JPS50137886A (fr) * 1974-03-29 1975-11-01
JPS5750535A (en) * 1980-09-12 1982-03-25 Toagosei Chem Ind Co Ltd Nonaqueous solvent type dispersant
JPS62265301A (ja) * 1986-05-12 1987-11-18 Nippon Soda Co Ltd シラン変性ブタジエン系重合体及び該重合体を用いた表面処理剤
JPH01210467A (ja) * 1988-02-19 1989-08-24 Dainichiseika Color & Chem Mfg Co Ltd 顔料組成物
JPH01259069A (ja) * 1988-04-08 1989-10-16 Nippon Paint Co Ltd アクリル樹脂で被覆した水性塗料用金属顔料
JPH0216110A (ja) * 1988-05-02 1990-01-19 Ppg Ind Inc アクリル重合体
JPH0291160A (ja) * 1988-09-28 1990-03-30 Dainippon Ink & Chem Inc 熱可塑性樹脂の着色剤用分散剤及びそれを含有する組成物

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009165910A (ja) * 2008-01-11 2009-07-30 Toyo Ink Mfg Co Ltd 分散剤、及びそれを用いた顔料組成物並びに顔料分散体

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Publication number Publication date
DE4191067T (fr) 1992-06-25

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