WO2002014392A1 - Procede de production d'une resine aromatique de petrole a point de ramollissement eleve, et encre d'impression contenant cette resine - Google Patents

Procede de production d'une resine aromatique de petrole a point de ramollissement eleve, et encre d'impression contenant cette resine Download PDF

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Publication number
WO2002014392A1
WO2002014392A1 PCT/JP2001/006970 JP0106970W WO0214392A1 WO 2002014392 A1 WO2002014392 A1 WO 2002014392A1 JP 0106970 W JP0106970 W JP 0106970W WO 0214392 A1 WO0214392 A1 WO 0214392A1
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WO
WIPO (PCT)
Prior art keywords
petroleum resin
softening point
turpentine
turpentine oil
gen
Prior art date
Application number
PCT/JP2001/006970
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English (en)
Japanese (ja)
Inventor
Hitoshi Yanagishita
Hironobu Soeda
Kazuo Kawai
Original Assignee
Nippon Petrochemicals Co., 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 Nippon Petrochemicals Co., Ltd. filed Critical Nippon Petrochemicals Co., Ltd.
Priority to JP2002519528A priority Critical patent/JPWO2002014392A1/ja
Publication of WO2002014392A1 publication Critical patent/WO2002014392A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/106—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C09D11/108—Hydrocarbon resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F240/00—Copolymers of hydrocarbons and mineral oils, e.g. petroleum resins

Definitions

  • the present invention relates to a method for producing an aromatic petroleum resin having a high softening point and excellent solubility in a non-aromatic solvent, and a printing ink containing the petroleum resin obtained by the method.
  • Petroleum resins are used in various applications such as tackifiers, modifiers, adhesives, paints, and printing inks.
  • petroleum resin is used as a vehicle or an auxiliary material, which is a liquid component that disperses a pigment and forms a film on a printing medium.
  • a petroleum resin when used as a vehicle, its purpose is to impart appropriate viscosity and improve the fluidity and interface suitability of the ink by wetting the pigment particles. Used to improve the properties and friction resistance.
  • the performance required for petroleum resins in this application is to dissolve in solvents without deteriorating the wetting performance on pigment particles and to have a high softening point.
  • aromatic solvents have been widely used as solvents for printing inks and paints.
  • problems such as air pollution and deterioration of work environment hygiene due to aromatic solvents have been pointed out.
  • replacement with non-aromatic solvents containing naphthenes and paraffins as main components is being studied.
  • non-aromatic solvents generally have significantly lower solubility for aromatic petroleum resins having a high softening point.
  • the aniline point which is a measure of solubility in printing ink resins, is about 15 ° C. higher for non-aromatic solvents than for aromatic solvents in the same boiling point range. Therefore, in a printing ink, if an aromatic solvent is directly replaced with a non-aromatic solvent having a similar boiling point range, the solubility of an aromatic petroleum resin having a high softening point becomes insufficient, and the ink becomes unsuitable.
  • Japanese Patent Application Laid-Open No. Sho 63-31312 discloses that the content of conjugated diolephine and the content of dicyclopentadiene are adjusted.
  • a method for producing a modified aromatic petroleum resin obtained by adding turpentine to a cracked fraction such as petroleum and copolymerizing the same has been proposed.
  • an object of the present invention is to provide a petroleum resin which improves the solubility in non-aromatic solvents without lowering the softening point. Disclosure of the invention
  • the present inventors have conducted intensive research on the above-mentioned problems, and as a result, have found that a fraction obtained by pyrolysis of petroleum and a turpentine oil having a specific gen value during the production of an aromatic petroleum resin are used as an acid catalyst.
  • the above problem can be solved by producing a high softening point aromatic petroleum resin excellent in solubility in a non-aromatic solvent which can solve the problem by polymerizing in the presence, and using the resin. I found that.
  • the first feature of the present invention is that a fraction having a boiling point of 140 to 220 ° C. obtained by the thermal cracking of petroleum (hereinafter referred to as “thermal cracking fraction”) and a Gen value.
  • thermal cracking fraction a fraction having a boiling point of 140 to 220 ° C. obtained by the thermal cracking of petroleum
  • Gen value a turpentine oil having a high softening point of 20 cg / g or more
  • a second feature of the present invention is that a high softening point fragrance in which the weight ratio of the polymerizable component in the “pyrolysis fraction” to the “specific gen-valent televin oil” is in the range of 100: 5 to 40.
  • the present invention relates to a method for producing an aromatic resin.
  • a third feature of the present invention relates to a method for producing a high softening point aromatic petroleum resin in which the “specified gen turpentine oil” contains] 3-ferrandrene.
  • a fourth feature of the present invention is that 15) -ferrandrene in "specified gen turpentine oil" is 15% by weight. / 0 or more, relates to a method for producing a high softening point aromatic petroleum resin.
  • a fifth feature of the present invention is that the weight ratio of the polymerizable component in the “pyrolysis fraction” to the] 3-ferrandrene in the “specific gen-valent terevin oil” is 100: 3 to 40%.
  • the present invention relates to a process for producing a high softening point aromatic petroleum resin within the range.
  • a sixth feature of the present invention relates to a printing ink containing a high softening point aromatic petroleum resin prepared by the above production method.
  • the fraction used in the present invention and having a boiling point in the range of 140 to 220 ° C. obtained by pyrolysis of petroleums is a polymer obtained by pyrolysis of petroleums such as crude oil, naphtha and butane.
  • the “pyrolysis fraction” is composed of a polymerizable component and a non-polymerizable component.
  • the polymerizable component is a mixture of various compounds.
  • styrene As its components, styrene, its alkyl derivative, for example, ⁇ -methylstyrene, vinyltoluene; indene, its alkyl derivative; cyclopentadiene, its alkyl derivative, for example, methylcyclopentane, and its addition polymer, for example, dicyclopentane And pentadiene.
  • the polymerizable component in the “pyrolysis fraction” is usually present in an amount of 10 to 90% by weight. Further, any one of the above polymerizable components may be used alone, or two or more thereof may be mixed with the above-mentioned fraction to adjust the composition ratio of the polymerizable components. In addition, the above fraction is used as it is, or After adjusting the composition ratio by the above method, it may be changed by a method such as distillation. For example, the composition ratio of the polymerizable component can be adjusted by adding dicyclopentadiene, or the like, or the content of vinyltoluene or indene can be adjusted by distilling the above fraction.
  • the non-polymerizable component in the “pyrolysis fraction” is composed of the remaining components other than the polymerizable component, and is mainly an aromatic hydrocarbon compound such as alkylbenzene. In the present invention, it mainly functions as a solvent during polymerization.
  • an aromatic hydrocarbon compound such as alkylbenzene is separately added as a non-polymerization component, and a polymerizable component is added. It is also possible to adopt a method of setting the content of 30 to 70% by weight with respect to the total amount including the turpentine.
  • turpentine refers to synthetic turpentine having a Gen value of 20 cg / g or more, or turpentine obtained from natural products, terbinic compounds, terpenoid compounds, and mixtures thereof (specified gen Value turpentine).
  • the gen value is defined by adding a predetermined amount of a toluene solution of maleic anhydride to 5 g of a sample, causing the mixture to react by boiling and refluxing, extracting and removing unreacted maleic anhydride with a predetermined amount of water, and removing phenolphthalein. This value is obtained by titration with an aqueous solution of sodium hydroxide (1 N) as an indicator.
  • Turpentine oil is generally obtained from natural products.
  • Turpentine oil which is obtained from natural products, is produced from volatile components of sap contained in softwoods, and is industrially obtained mainly as gum terebine, steam wood turpentine, sulfate wood turpentine, and carbonized pad terebine.
  • gum turpentine is obtained by distilling raw pine crab collected from wounds and scars on raw pine trees.
  • Steam turpentine or turpentine can be obtained by distilling the extract of unharvested pine stumps that have fallen off the bark and sapwood.
  • Sulfate wood turpentine or sulfate turpentine is obtained by condensing the steam generated during the heating step of the paper kraft (sulfate) pulping process.
  • the carbonized wood turpentine is produced from light distillates obtained by carbonizing (contaminating) coniferous wood such as greasy trees and felled trees. Those commonly used are those further purified by distillation.
  • a turpentine oil obtained from a natural product in the present invention, a turpentine having a Gen value of 20 cZg or more is used irrespective of its components and composition ratio. Jen value ranges, rather preferably is 20 cg / g or more 1 90 cg / g or less, more preferably more than 20 c g / g 1 5 0 cg / g or less, more preferably 2 0 cg / g or more l OO cg / g or less.
  • Petroleum resins produced using those with a Gen value of less than 20 cg / g have insufficient solubility in non-aromatic solvents, and a difference of reactivity with the "pyrolyzed fraction" above 190 cg Zg Becomes too large.
  • the Gen value obtained from a natural product is 20 cg / g or less
  • the Gen value is within the range specified in the present invention by appropriately isomerizing the Gen value within the range specified in the present invention.
  • Turpentine oil "and can also be used. This isomerization can be carried out by conventional heat isomerization, but the actual reaction is a complicated reaction involving reactions such as thermal decomposition and thermal rearrangement in addition to isomerization. For example, crude sulfate turpentine, a- pinene, etc.
  • Gen value Turpentine oil J is heated and isomerized at 315 to 325 ° C in a gas phase at atmospheric pressure using a stainless steel tube reactor, and then, if necessary, By distilling under reduced pressure, the Gen value can be increased to obtain “Specified Gen value Turpentine oil J.
  • This isomerization is carried out by using natural or any synthetic turpentine oil having a Gen value of 20 cgZg or less. Alternatively, it can be applied to the case where a mixture of these compounds or Terdinoid compounds is used as “specified gen turpentine oil”.
  • Specific gen turpentine oil includes natural or any synthetic turpentine oil and / or terpenoid compounds (including mixtures thereof), such as ⁇ -phenlandrene, myrcene, and terbinene.
  • Terbinene, ⁇ -terbinene, limonene, ⁇ -pyrronene, J3-pyrronene, etc., and derivatives thereof can be obtained by adding a predetermined amount.
  • 3-Fuelandrene can be obtained by further rectifying the fraction obtained by fractionating these essential oils as they are or after isomerizing them.
  • it can be produced by isomerizing and fractionating turpentine oil such as gum turpentine, steam wood turpentine, sanolephate wood turpentine, and carbonized wood turpentine by heat or the like.
  • the mixing ratio of] 3-prandren to the polymerizable component in the "pyrolysis fraction” was calculated based on 100 parts by weight of the polymerizable component in the "pyrolysis fraction". It is also preferable to use parts by weight in order to obtain the effects of the present invention. If the amount is less than 3 parts by weight, the obtained resin generally has insufficient solubility, while if it exceeds 40 parts by weight, the softening point generally decreases.
  • turpentine oil obtained by addition of natural or synthetic turpentine] can be used as “specified turpentine oil”.
  • a fraction of crude sulfate turpentine is purified and separated by distillation under reduced pressure, and has a boiling point at normal pressure of 150 to 200 ° C, preferably 16 to 50 ° C. Fractions in the range of 185 ° C, isomers of crude sulfate turpentine.
  • the polymerization operation for polymerizing the aromatic petroleum resin of the present invention may be either a batch system or a continuous system.
  • the catalyst may be added to the polymerization raw material or, if necessary, the polymerization raw material may be added to the catalyst dissolved or dispersed in an appropriate solvent.
  • Examples of the acid catalyst in the present invention include known Friedel-Crafts catalysts, for example, sulfuric acid, aluminum trichloride, boron trifluoride, and complex compounds thereof.
  • Protonic acids such as hydrochloric acid, solid acids such as silica and alumina, and acidic ion exchange resins can be used.
  • the polymerization reaction 0.05 to 5% by weight of the above catalyst is added to the raw material, and the reaction can be performed at a temperature of 120 to 70 ° C. for a period of 0.2 to 5 hours. Thereafter, if necessary, an unreacted product and a low-polymerized product can be separated by a conventional method to obtain an aromatic petroleum resin having a high softening point.
  • the aromatic petroleum resin obtained by the production method of the present invention has excellent solubility in non-aromatic solvents, and has a high softening point, and its softening point is 130 ° C or more, preferably 135 ° C or more. To 220 ° C, more preferably 140 ° C to 220 ° C.
  • the aromatic petroleum resin produced by the present invention is used for various applications such as tackifier components such as hot melt adhesives, pressure-sensitive adhesives and sealing agents, paints, and additives for plastics. It can be suitably used for paints or printing inks, utilizing the fact that it is well soluble in system solvents and has a high softening point.
  • the aromatic petroleum resin produced by the method of the present invention is used as a printing ink according to a known compounding recipe.
  • Non-aromatic solvents for example, naphthenic solvents and aliphatic solvents which are non-aromatic solvents having an aromatic hydrocarbon content of not more than 3% by volume, preferably not more than 1% by volume, etc.
  • the hydrocarbon solution can be obtained by dissolving the group petroleum resin in an appropriate ratio, for example, 1 to 70% by weight. This makes it possible to provide a printing ink comprising a non-aromatic solvent that is less harmful to air pollution and working environment hygiene.
  • known mouth-modified phenol resins, alkyd resins, drying oils, semi-drying oils, non-drying oils, and the like can be mixed simultaneously if necessary. Alternatively, they can be mixed after separately forming a varnish.
  • appropriate pigments for inks such as yellow, red, indigo, and black are dispersed and mixed in an appropriate amount by a known method, and further comprise a friction resistance improver, a drying inhibitor, an ink dryer, and the like.
  • an offset printing ink such as a rotary offset ink and a sheet-fed offset ink can be manufactured.
  • various ink compositions such as newspaper printing inks and letterpress printing inks Can be manufactured.
  • the aromatic petroleum resin produced by the method of the present invention can be used in various fields where existing aromatic petroleum resins are used in addition to these uses.
  • a hot-melt adhesive is added to a base resin as a tackifier component such as a pressure-sensitive adhesive and a sealing agent.
  • Base resins used in hot melt adhesives include ethylene monoacetate copolymer, ethylene monoacrylate copolymer, styrene monobutadiene styrene copolymer, styrene monoisoprene monostyrene copolymer, and hydrides thereof. And the like.
  • Examples of the base resin used for the pressure-sensitive adhesive include natural rubber, synthetic rubber, styrene-butadiene-styrene copolymer, styrene-isoprene-styrene copolymer, and hydrides thereof. .
  • aromatic petroleum resin of the present invention is also useful as an additive for plastics, and can be used, for example, as an additive for polyolefin films and sheets. In addition, it can be used as an additive for paints, road pavement materials, rubber, and plastic moldings.
  • the solubility is represented by the following equation.
  • Solubility solvent amount (g) / sample (g)
  • Aromatic solvents used were naphthenic hydrocarbon solvent;: is (aromatic hydrocarbon content 1 volume 0/0 trade names: AF Solvent No. 7, Mitsubishi Oil Co., Ltd.).
  • Turpentine having various gen values was produced. Some of them are exemplified. Turpentine oil whose production method is not described was recovered according to these methods.
  • Turpentine oil with a Gen value of 30 (c gZg): (“Specified Gen value Turpentine oil”) Crude sulfur turpentine is placed in a glass distillation column (25 mm ID, 500 mm length) in stainless steel DEXON packing ( (Diameter: 3 mm) and distilled under reduced pressure (boiling point at normal pressure: 165 to 185 ° C) to recover.
  • Turpentine oil with a Gen value of 45 (cg / g): (“Specified Gen value Turpentine oil”)
  • a reactor 14 mm ID, 50 Omm length) filled with stainless steel filler and set vertically in a tube furnace The reaction was performed by heating. The reaction temperature was detected by a thermocouple inside the reactor. A preheating tube with a small inside diameter was provided at the entrance to the reactor.
  • crude sulfate turpentine was supplied by a metering pump, vaporized, and then continuously introduced into the reactor. The reaction was performed at 320 ° C ⁇ 5 ° C.
  • the crude product distilled from the outlet of the reactor was condensed by cooling and collected in a 1000 ml round bottom flask sealed with nitrogen. Antioxidants were added to the crude product at 100-1000 ppm.
  • the crude product was distilled using the distillation apparatus used in (a) (boiling point at normal pressure: 165-185 ° C) and recovered.
  • composition ratio of the polymerizable components in the feedstock oil was adjusted by adding 22 parts by weight of 97% by weight of dicyclopentadiene (DCPD) to 78 parts by weight of the polymerizable components of the “pyrolysis fraction”.
  • DCPD dicyclopentadiene
  • the turpentine oil having a Gen value of 30 (c g / g) was added to the stock oil, and the mixture was operated under the same conditions as in Examples 1 to 9 to obtain a petroleum resin.
  • the softening point and solubility of the obtained resin were measured by the methods described above. Table 1 shows the results. It had a high softening point and excellent solubility.
  • Turpentine oil which does not fall under the category of “specific turpentine oil”, was added to 100 parts by weight of the polymerizable component of the “pyrolysis fraction”, and the mixture was operated under the same conditions as in Examples 1 to 9 to obtain a petroleum resin.
  • the softening point and solubility of the obtained resin were measured by the methods described above. Table 1 shows the results. Poor solubility.
  • the present invention relates to a method for producing an aromatic petroleum resin having a high softening point and excellent solubility in a non-aromatic solvent.
  • This high softening point aromatic petroleum resin is used for hot melt adhesion IJ, sealants, paints, inks, etc.
  • non-aromatic solvents can be used in printing ink applications as compared with conventional ones, so air pollution and work environment hygiene problems can be significantly reduced.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne un procédé de production d'une résine aromatique de pétrole à point de ramollissement élevé, possédant une solubilité satisfaisante lorsqu'elle est placée dans des solvants non aromatiques, ce procédé consistant à polymériser une fraction obtenue par pyrolyse de pétrole et possédant un point d'ébullition se situant dans la plage comprise entre 140 et 220 °C, avec une huile de térébenthine dont l'indice de diène est de l'ordre de 20 cg/g ou davantage, en présence d'un catalyseur d'acide.
PCT/JP2001/006970 2000-08-14 2001-08-13 Procede de production d'une resine aromatique de petrole a point de ramollissement eleve, et encre d'impression contenant cette resine WO2002014392A1 (fr)

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JP2002519528A JPWO2002014392A1 (ja) 2000-08-14 2001-08-13 高軟化点芳香族石油樹脂の製造法およびその石油樹脂を含む印刷インキ

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101412788B (zh) * 2007-10-18 2011-05-04 中国石化上海石油化工股份有限公司 碳九馏份制环戊二烯及甲基环戊二烯生产废液的利用方法
CN101412789B (zh) * 2007-10-18 2012-04-18 中国石化上海石油化工股份有限公司 碳九馏份制取环戊二烯生产废液的利用方法
WO2012147514A1 (fr) * 2011-04-26 2012-11-01 Ｊｘ日鉱日石エネルギー株式会社 Résine alcénylique aromatique
US11613675B2 (en) 2019-01-31 2023-03-28 Synthomer Adhesive Technologies Llc Packaging adhesives comprising low volatile tackifier compositions

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5565248A (en) * 1978-11-10 1980-05-16 Nippon Oil Co Ltd Hot-melt composition
JPS56157414A (en) * 1980-05-09 1981-12-04 Nippon Oil Co Ltd Production of hydrocarbon resin
US4857617A (en) * 1987-07-30 1989-08-15 Tosoh Corporation Process for producing a high softening point hydrocarbon resin
EP0842984A1 (fr) * 1996-05-28 1998-05-20 Nippon Petrochemicals Co., Ltd. Composition thermofusible et resine de petrole aromatique modifiee utilisee dans celle-ci

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5565248A (en) * 1978-11-10 1980-05-16 Nippon Oil Co Ltd Hot-melt composition
JPS56157414A (en) * 1980-05-09 1981-12-04 Nippon Oil Co Ltd Production of hydrocarbon resin
US4857617A (en) * 1987-07-30 1989-08-15 Tosoh Corporation Process for producing a high softening point hydrocarbon resin
EP0842984A1 (fr) * 1996-05-28 1998-05-20 Nippon Petrochemicals Co., Ltd. Composition thermofusible et resine de petrole aromatique modifiee utilisee dans celle-ci

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101412788B (zh) * 2007-10-18 2011-05-04 中国石化上海石油化工股份有限公司 碳九馏份制环戊二烯及甲基环戊二烯生产废液的利用方法
CN101412789B (zh) * 2007-10-18 2012-04-18 中国石化上海石油化工股份有限公司 碳九馏份制取环戊二烯生产废液的利用方法
WO2012147514A1 (fr) * 2011-04-26 2012-11-01 Ｊｘ日鉱日石エネルギー株式会社 Résine alcénylique aromatique
JP2012229324A (ja) * 2011-04-26 2012-11-22 Jx Nippon Oil & Energy Corp アルケニル芳香族系樹脂
US11613675B2 (en) 2019-01-31 2023-03-28 Synthomer Adhesive Technologies Llc Packaging adhesives comprising low volatile tackifier compositions
US11661531B2 (en) 2019-01-31 2023-05-30 Synthomer Adhesives Technology LLC Hygiene adhesives comprising low volatile tackifier compositions
US11725122B2 (en) 2019-01-31 2023-08-15 Synthomer Adhesive Technologies Llc Processes for making low volatile tackifier compositions
US11753566B2 (en) 2019-01-31 2023-09-12 Synthomer Adhesive Technologies Llc Low volatile tackifier compositions

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