WO2012096135A1 - 液状レゾール型フェノール樹脂 - Google Patents
液状レゾール型フェノール樹脂 Download PDFInfo
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- WO2012096135A1 WO2012096135A1 PCT/JP2011/080405 JP2011080405W WO2012096135A1 WO 2012096135 A1 WO2012096135 A1 WO 2012096135A1 JP 2011080405 W JP2011080405 W JP 2011080405W WO 2012096135 A1 WO2012096135 A1 WO 2012096135A1
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- liquid resol
- resol type
- phenol resin
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- phenolic resin
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/024—Polyamines containing oxygen in the form of ether bonds in the main chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/205—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings
- C07C39/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C08G12/06—Amines
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/10—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with phenol
Definitions
- the present invention relates to a liquid resol type phenol resin.
- Phenol resin which is a thermosetting resin, is widely used as a binder to bond materials that are base materials, and has excellent mechanical properties, electrical properties, and adhesiveness, so it is used in various fields. .
- the liquid phenol resin is used by impregnating a base material mainly composed of fibers.
- Such applications include FRP, copper-clad laminate, wet paper friction material and the like.
- the amount of friction material using phenolic resin as a binder is increasing in automobiles, railway vehicles and the like.
- a liquid resol type phenol resin is used for a friction material used in an automatic transmission such as an automatic vehicle, which is called a wet friction material.
- the required characteristics of the phenolic resin for wet friction materials are increasing year by year, and in particular, the demand for improving the flexibility of the phenolic resin is increasing for the purpose of improving the friction coefficient and durability.
- a cured product of a general phenol resin is excellent in mechanical properties, but has a property of being hard and brittle, and cannot be said to be excellent in flexibility.
- the present invention provides a liquid resol type phenolic resin that has excellent properties of a phenolic resin, such as heat resistance and curability, and is capable of obtaining a molded product having excellent flexibility.
- a liquid resol type phenol resin obtained by reacting (A) a phenol and (B) a secondary and / or tertiary alkylamine compound in the presence of a basic catalyst.
- liquid resol type phenolic resin of the present invention When the liquid resol type phenolic resin of the present invention is used as a binder, a molded product having excellent heat resistance, curability and flexibility can be obtained.
- the liquid resol type phenol resin of this invention is demonstrated in detail below, it is not limited to these examples. Additions, omissions, substitutions, and other modifications can be made without departing from the spirit of the present invention.
- the liquid resol type phenol resin of the present invention is obtained by reacting (A) a phenol with (B) a secondary and / or tertiary alkylamine compound in the presence of a basic catalyst.
- a liquid resol type phenol resin is synthesized by reacting ordinary phenol and hexamine in the presence of a basic catalyst. Can do.
- Phenols examples include cresols such as phenol, o-cresol, m-cresol, p-cresol, 2,3-xylenol, 2,4 -Xylenols such as xylenol, 2,5-xylenol, 2,6-xylenol, 3,4-xylenol, 3,5-xylenol, and ethylphenols such as o-ethylphenol, m-ethylphenol, p-ethylphenol Butylphenols such as isopropylphenol, butylphenol and p-tert-butylphenol, alkylphenols such as p-tert-amylphenol, p-octylphenol, p-nonylphenol and p-cumylphenol, fluorophenol and chlorophenol Halogenated phenols such as bro
- the phenols used in the present invention are preferably soluble in the organic solvent described later.
- these phenols those selected from phenol, cresols, and bisphenol A are preferable. Thereby, mechanical strength can be raised in the molded article using the liquid resol type phenol resin of this invention.
- the secondary and / or tertiary alkylamine compound used in the liquid resol type phenolic resin of the present invention includes, for example, dimethylamine as a secondary alkylamine compound.
- diethylamine and tertiary alkylamine compounds include triethylamine, tetramethylethylenediamine, hexamethylenetetramine, and the like. These can be used alone or in combination of two or more. Among these, it is preferable to use hexamethylenetetramine. By using this, the reaction can be performed without using an aldehyde source such as formalin.
- Examples of the basic catalyst used in the liquid resol type phenolic resin of the present invention include alkali metal hydroxides such as sodium hydroxide, lithium hydroxide and potassium hydroxide, tertiary amines such as aqueous ammonia and triethylamine, Alkali earth metal oxides such as calcium, magnesium and barium, and alkaline substances such as hydroxide and sodium carbonate can be used alone or in combination of two or more.
- the amount of the basic catalyst to be used is not particularly limited, but can be usually 0.01 to 0.1 mol with respect to 1 mol of the phenol (A).
- the content ratio of each component of the liquid resol type phenol resin of the present invention is 0 to 100 parts by weight, preferably 0 to 50 parts by weight, secondary and / or 3 parts of phenols per 1000 parts by weight of the liquid resol type phenol resin.
- a suitable amount is 0 to 80 parts by weight, preferably 0 to 40 parts by weight, and 0 to 20 parts by weight, preferably 0 to 10 parts by weight, of the basic catalyst.
- the nitrogen content with respect to the whole liquid resol type phenolic resin is preferably 3 to 30% by weight. More preferably, it is 5 to 10% by weight. If the nitrogen content is higher than this, the viscosity becomes high and it becomes difficult to unload. Further, when the amount of nitrogen is less than this, the effect of improving flexibility and heat resistance is reduced.
- the number of moles of the (B) secondary and / or tertiary alkylamine compound is 0.13 to 0 with respect to 1 mole of the above (A) phenol. .35 moles are preferred. More preferably, it is 0.18 to 0.30 mol.
- the liquid resol type phenolic resin of the present invention is obtained by reacting the above-described (A) phenols with (B) secondary and / or tertiary alkylamine compounds in the presence of a basic catalyst.
- the reaction temperature is preferably 50 to 110 ° C, more preferably 80 to 100 ° C.
- an organic solvent can be used to dilute the resin.
- an organic solvent used for dilution For example, alcohol organic solvents, such as methanol, ethanol, isopropanol, and butanol, ketone organic solvents, such as acetone, methyl ethyl ketone, and methyl isobutyl ketone, aromatics, such as toluene and ethylbenzene Hydrocarbon solvents and mixtures thereof can be used.
- the liquid resol type phenolic resin of the present invention can be used for impregnation. Impregnation refers to soaking in a gap in a structure or structure such as a substrate.
- the base material to be impregnated include those using metal fibers, glass fibers, carbon fibers, chemical fibers and the like. In particular, it can be suitably used for wet paper friction material applications, and when used for wet paper friction material applications, in addition to these fiber components, a paper base filled with friction modifiers such as cashew dust, diatomaceous earth, etc. Materials can be used.
- the obtained molded product has excellent characteristics of phenol resin such as heat resistance and curability, and also has excellent flexibility.
- Parts described herein indicates “parts by weight”, and “%” indicates “% by weight”.
- Example 2 The same procedure as in Example 1 was carried out except that 450 parts by weight of hexamethylenetetramine (0.30 moles relative to 1 mole of phenol) was obtained, and 2780 parts by weight of a liquid resol type phenol resin was obtained.
- Example 2 The same procedure as in Example 1 was carried out except that 270 parts by weight of hexamethylenetetramine (0.18 moles relative to 1 mole of phenol) was obtained to obtain 2600 parts by weight of a liquid resol type phenolic resin.
- Example 1 was the same as Example 1 except that the mixed cresol containing 63% metacresol and 27% paracresol was used as the phenol of Example 1 and 320 parts by weight of hexamethylenetetramine (0.25 mol with respect to 1 mol of phenol). In this way, 2650 parts by weight of a liquid resol type phenol resin was obtained.
- Example 1 370 parts by weight of hexamethylenetetramine was reacted as 1600 parts by weight of a 37% formalin aqueous solution. After dehydrating this at 80 ° C. for 30 minutes under reduced pressure, 1800 parts by weight of acetone was added and cooled to 40 ° C. or less to obtain 4100 parts by weight of a liquid resol type phenol resin.
- Impregnated paper was prepared using the liquid resol type phenol resin obtained in the examples and comparative examples. A commercially available filter paper (120 mm ⁇ 10 mm ⁇ thickness 1 mm) was used as the substrate. The liquid resol type phenolic resin obtained in Examples and Comparative Examples was diluted with acetone to impregnate the above filter paper in a solution having a resin concentration of 30%, then dried and cured in an oven at 190 ° C. for 30 minutes, and tested. I got a piece.
- the tensile strength was measured according to JIS P 8113 “Paper and paperboard—Testing method for tensile properties—” under normal conditions and after treatment at 240 ° C. for 1 hour. Further, each Rockwell hardness was measured in accordance with JIS K 7202 “Plastic Rockwell Hardness Test Method”.
- the tensile strength is measured as an index of the mechanical strength of the cured product (molded product). In the present invention, the higher the value, the better.
- the Rockwell hardness is measured as an index representing the hardness of a cured product (molded product), and in the present invention, a lower numerical value is preferable.
- Examples 1 to 4 are liquid resol type phenol resins of the present invention.
- the obtained cured resin was rich in flexibility because of its low Rockwell hardness, and was found to be excellent in heat resistance because of its high strength retention rate (tensile strength) after heat treatment at 240 ° C.
- Comparative Example 1 is a resol-type resin obtained by using phenol and formaldehyde, but has low flexibility because of its high Rockwell hardness, a large decrease in tensile strength after heat treatment at 240 ° C., and heat resistance. An excellent resin could not be obtained.
- the present invention it is possible to provide a liquid resol type phenolic resin that has excellent properties of a phenolic resin such as heat resistance and curability and that can provide a molded product that is also excellent in flexibility. Therefore, the present invention is extremely useful industrially.
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- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Abstract
Description
本願は、2011年1月14日に、日本に出願された特願2011-005440号に基づき優先権を主張し、その内容をここに援用する。
液状フェノール樹脂は成形品を得るために、繊維を主成分とする基材に含浸して用いられる。このような用途としてはFRP、銅張積層板、湿式ペーパー摩擦材等が挙げられる。
その中でも自動車、鉄道車両などにおける、フェノール樹脂をバインダーとして使用した摩擦材の使用量が増加している。特に湿式摩擦材と呼ばれる、オートマチック車等の自動変速機等において使用される摩擦材には、一般的に液状レゾール型フェノール樹脂が用いられる。その湿式摩擦材用フェノール樹脂に対する要求特性は年々高まっており、特に、摩擦係数や耐久性の向上を目的として、フェノール樹脂の柔軟性向上への要求が高まってきている。しかしながら、一般的なフェノール樹脂の硬化物は、機械的特性に優れる反面、堅くてもろいという性質をもち、柔軟性に優れているとは言えない。
しかし、このような変性のフェノール樹脂は、熱履歴後の強度低下が著しく、サイクル寿命が短いという課題があった。
[1] (A)フェノール類と、(B)2級及び/又は3級のアルキルアミン化合物とを塩基性触媒の存在下で反応させてなる液状レゾール型フェノール樹脂。
[2] 前記液状レゾール型フェノール樹脂全体に対する窒素含有量が、3~30重量%である、前記[1]に記載の液状レゾール型フェノール樹脂。
[3] 前記(B)2級及び/又は3級のアルキルアミン化合物が、ヘキサメチレンテトラミンである前記[1]又は[2]に記載の液状レゾール型フェノール樹脂。
[4]前記(A)フェノール類と(B)2級及び/又は3級のアルキルアミン化合物とを、(B)/(A)モル比=0.13~0.35で反応させてなる前記[1]ないし[3]のいずれかに記載の液状レゾール型フェノール樹脂。
[5] 含浸用に用いられる、前記[1]ないし[4]のいずれかに記載の液状レゾール型フェノール樹脂。
本発明の液状レゾール型フェノール樹脂は、(A)フェノール類と、(B)2級及び/又は3級のアルキルアミン化合物を塩基性触媒の存在下で反応させてなる。
本発明に用いる液状レゾール型フェノール樹脂を得る手法は種々存在し限定されるものではないが、例えば通常のフェノールとヘキサミンを塩基性触媒存在下で反応させることにより液状レゾール型フェノール樹脂を合成することができる。
本発明の液状レゾール型フェノール樹脂に用いられるフェノール類としては、例えば、フェノール、o-クレゾール、m-クレゾール、p-クレゾール等のクレゾール類、2,3-キシレノール、2,4-キシレノール、2,5-キシレノール、2,6-キシレノール、3,4-キシレノール、3,5-キシレノール等のキシレノール類、o-エチルフェノール、m-エチルフェノール、p-エチルフェノール等のエチルフェノール類、イソプロピルフェノール、ブチルフェノール、p-tert-ブチルフェノール等のブチルフェノール類、p-tert-アミルフェノール、p-オクチルフェノール、p-ノニルフェノール、p-クミルフェノール等のアルキルフェノール類、フルオロフェノール、クロロフェノール、ブロモフェノール、ヨードフェノール等のハロゲン化フェノール類、p-フェニルフェノール、アミノフェノール、ニトロフェノール、ジニトロフェノール、トリニトロフェノール等の1価フェノール置換体、及び、1-ナフトール、2-ナフトール等の1価のフェノール類、レゾルシン、アルキルレゾルシン、ピロガロール、カテコール、アルキルカテコール、ハイドロキノン、アルキルハイドロキノン、フロログルシン、ビスフェノールA、ビスフェノールF、ビスフェノールS、ジヒドロキシナフタリン等の多価フェノール類などが挙げられる。これらを単独あるいは2種以上を混合して使用することができる。本発明に使用されるフェノール類は、後述する有機溶剤に可溶であることが好ましい。
これらのフェノール類の中でも、フェノール、クレゾール類、ビスフェノールAから選ばれるものが好ましい。これにより、本発明の液状レゾール型フェノール樹脂を用いた成形品において、機械的強度を高めることができる。
本発明の液状レゾール型フェノール樹脂で用いられる2級及び/又は3級のアルキルアミン化合物としては、例えば、2級アルキルアミン化合物として、ジメチルアミン、ジエチルアミン、3級アルキルアミン化合物として、トリエチルアミン、テトラメチルエチレンジアミン、ヘキサメチレンテトラミンなどが挙げられる。これらを単独で使用または2種以上併用することができる。
これらの中でも、ヘキサメチレンテトラミンを用いることが好ましい。これを用いることで、ホルマリン等のアルデヒド源を用いずに反応させることができる。
本発明の液状レゾール型フェノール樹脂においては、液状レゾール型フェノール樹脂全体に対する窒素含有量が、3~30重量%であることが好ましい。より好ましくは5~10重量%である。
窒素含有量がこれより多いと、高粘度となり釜出しが困難となる。また、窒素量がこれより少ないと、柔軟性、耐熱性の向上効果が小さくなる。
これにより、本発明の液状レゾール型フェノール樹脂を含浸用に使用した場合に、良好な含浸性を有するとともに、成形品の柔軟性を向上させることができる。
得られた成形品は、耐熱性、硬化性など、フェノール樹脂の優れた特性を有し、かつ、柔軟性にも優れている。
ここに記載されている「部」は「重量部」を、「%」は「重量%」を示す。
撹拌装置、還流冷却器及び温度計を備えた反応装置に、フェノール1000重量部、ヘキサメチレンテトラミン370重量部(フェノール1モルに対して0.25モル)、メタノール100重量部、アセトン100重量部および50%水酸化ナトリウム水溶液を20重量部添加し、95℃に加熱昇温させ3時間保持した。
その後、アセトン1200重量部を加え、40℃以下に冷却して、液状レゾール型フェノール樹脂2700重量部を得た。
実施例及び比較例で得られた液状レゾール型フェノール樹脂を用いて、含浸紙を作製した。基材には市販の濾紙(120mm×10mm×厚さ1mm)を使用した。
実施例及び比較例で得られた液状レゾール型フェノール樹脂をアセトンで希釈して樹脂濃度を30%にした溶液中に上記濾紙を含浸した後、190℃のオーブンで30分間乾燥、硬化し、試験片を得た。得られた試験片について、JIS P 8113「紙及び板紙-引張特性の試験方法-」に準拠して、常態、及び、240℃1時間処理後について、各々、引張強さを測定した。また、JIS K 7202「プラスチックのロックウェル硬さ試験方法」に準拠して、各々、ロックウェル硬度を測定した。なお、引張強さは硬化物(成形品)の機械的強度の指標として測定したものであり、本発明においては数値が高いほど好ましい。また、ロックウェル硬度は硬化物(成形品)の硬さを表す指標として測定したものであり、本発明においては数値が低い方が好ましい。
一方、比較例1は、フェノール及びホルムアルデヒドを用いて得られたレゾール型樹脂であるが、ロックウェル硬度が高いことから柔軟性が低く、240℃熱処理後の引張強さの低下が大きく、耐熱性に優れた樹脂を得ることができなかった。
Claims (5)
- (A)フェノール類と、(B)2級及び/又は3級のアルキルアミン化合物とを塩基性触媒の存在下で反応させてなる液状レゾール型フェノール樹脂。
- 前記液状レゾール型フェノール樹脂全体に対する窒素含有量が、3~30重量%である、請求項1に記載の液状レゾール型フェノール樹脂。
- 前記(B)2級及び/又は3級のアルキルアミン化合物が、ヘキサメチレンテトラミンである請求項1又は2に記載の液状レゾール型フェノール樹脂。
- 前記(A)フェノール類と(B)2級及び/又は3級のアルキルアミン化合物とを、(B)/(A)モル比=0.13~0.35で反応させてなる請求項1ないし3のいずれかに記載の液状レゾール型フェノール樹脂。
- 含浸用に用いられる、請求項1ないし4のいずれかに記載の液状レゾール型フェノール樹脂。
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13/979,063 US20130310612A1 (en) | 2011-01-14 | 2011-12-28 | Liquid resol-type phenolic resin |
CA2824575A CA2824575A1 (en) | 2011-01-14 | 2011-12-28 | Liquid resol-type phenolic resin |
JP2012552663A JP5761204B2 (ja) | 2011-01-14 | 2011-12-28 | 液状レゾール型フェノール樹脂 |
KR1020137019479A KR101810725B1 (ko) | 2011-01-14 | 2011-12-28 | 액상 레졸형 페놀 수지 |
CN201180064382.9A CN103282407B (zh) | 2011-01-14 | 2011-12-28 | 液态甲阶型酚醛树脂 |
EP11855299.1A EP2664642A4 (en) | 2011-01-14 | 2011-12-28 | LIQUID RESOL-PHENOL RESIN |
US14/625,337 US9657139B2 (en) | 2011-01-14 | 2015-02-18 | Liquid resol-type phenolic resin |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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JP2011005440 | 2011-01-14 | ||
JP2011-005440 | 2011-01-14 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
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US13/979,063 A-371-Of-International US20130310612A1 (en) | 2011-01-14 | 2011-12-28 | Liquid resol-type phenolic resin |
US14/625,337 Continuation US9657139B2 (en) | 2011-01-14 | 2015-02-18 | Liquid resol-type phenolic resin |
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WO2012096135A1 true WO2012096135A1 (ja) | 2012-07-19 |
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PCT/JP2011/080405 WO2012096135A1 (ja) | 2011-01-14 | 2011-12-28 | 液状レゾール型フェノール樹脂 |
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US (2) | US20130310612A1 (ja) |
EP (1) | EP2664642A4 (ja) |
JP (1) | JP5761204B2 (ja) |
KR (1) | KR101810725B1 (ja) |
CN (1) | CN103282407B (ja) |
CA (1) | CA2824575A1 (ja) |
WO (1) | WO2012096135A1 (ja) |
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JP6412063B2 (ja) * | 2016-06-24 | 2018-10-24 | トヨタ自動車株式会社 | バッテリパック構造 |
CN114599757B (zh) * | 2019-11-01 | 2022-09-13 | 住友电木株式会社 | 湿式摩擦材料用粘接剂组合物 |
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JPH0959599A (ja) | 1995-08-25 | 1997-03-04 | Aisin Chem Co Ltd | 湿式摩擦材 |
JP2004277624A (ja) * | 2003-03-18 | 2004-10-07 | Sumitomo Bakelite Co Ltd | ナフトール樹脂の製造方法 |
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JP2007217650A (ja) * | 2006-02-20 | 2007-08-30 | Sekisui Chem Co Ltd | 熱硬化性樹脂の製造方法、熱硬化性樹脂、それを含む熱硬化性組成物、成形体、硬化体、硬化成形体、並びにそれらを含む電子機器 |
JP2009067921A (ja) * | 2007-09-14 | 2009-04-02 | Sumitomo Bakelite Co Ltd | オイル変性フェノール樹脂乳濁液 |
JP2010138273A (ja) * | 2008-12-11 | 2010-06-24 | Sumitomo Bakelite Co Ltd | 湿式摩擦材用フェノール樹脂組成物及び摩擦材 |
JP2011021093A (ja) * | 2009-07-15 | 2011-02-03 | Lignyte Co Ltd | 変性フェノール樹脂、その製造方法、フェノール樹脂組成物、耐火物組成物、鋳型用レジンコーテッドサンド、成形材料、不織布、硬化物、炭化物、活性炭 |
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2011
- 2011-12-28 CA CA2824575A patent/CA2824575A1/en not_active Abandoned
- 2011-12-28 US US13/979,063 patent/US20130310612A1/en not_active Abandoned
- 2011-12-28 KR KR1020137019479A patent/KR101810725B1/ko active IP Right Grant
- 2011-12-28 JP JP2012552663A patent/JP5761204B2/ja active Active
- 2011-12-28 EP EP11855299.1A patent/EP2664642A4/en not_active Withdrawn
- 2011-12-28 WO PCT/JP2011/080405 patent/WO2012096135A1/ja active Application Filing
- 2011-12-28 CN CN201180064382.9A patent/CN103282407B/zh not_active Expired - Fee Related
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2015
- 2015-02-18 US US14/625,337 patent/US9657139B2/en active Active
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JPS5270000A (en) * | 1974-12-09 | 1977-06-10 | Vladimir Washiriebichi Moiseef | Process for producing phenol amine resin |
JPH0959599A (ja) | 1995-08-25 | 1997-03-04 | Aisin Chem Co Ltd | 湿式摩擦材 |
JP2004277435A (ja) * | 2003-01-20 | 2004-10-07 | Nok Corp | 加硫接着剤組成物 |
JP2004277624A (ja) * | 2003-03-18 | 2004-10-07 | Sumitomo Bakelite Co Ltd | ナフトール樹脂の製造方法 |
JP2007217650A (ja) * | 2006-02-20 | 2007-08-30 | Sekisui Chem Co Ltd | 熱硬化性樹脂の製造方法、熱硬化性樹脂、それを含む熱硬化性組成物、成形体、硬化体、硬化成形体、並びにそれらを含む電子機器 |
JP2009067921A (ja) * | 2007-09-14 | 2009-04-02 | Sumitomo Bakelite Co Ltd | オイル変性フェノール樹脂乳濁液 |
JP2010138273A (ja) * | 2008-12-11 | 2010-06-24 | Sumitomo Bakelite Co Ltd | 湿式摩擦材用フェノール樹脂組成物及び摩擦材 |
JP2011021093A (ja) * | 2009-07-15 | 2011-02-03 | Lignyte Co Ltd | 変性フェノール樹脂、その製造方法、フェノール樹脂組成物、耐火物組成物、鋳型用レジンコーテッドサンド、成形材料、不織布、硬化物、炭化物、活性炭 |
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Non-Patent Citations (1)
Title |
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See also references of EP2664642A4 |
Also Published As
Publication number | Publication date |
---|---|
KR20140003501A (ko) | 2014-01-09 |
EP2664642A4 (en) | 2014-12-10 |
KR101810725B1 (ko) | 2017-12-19 |
CN103282407B (zh) | 2015-01-21 |
CA2824575A1 (en) | 2012-07-19 |
US20130310612A1 (en) | 2013-11-21 |
US9657139B2 (en) | 2017-05-23 |
US20150158979A1 (en) | 2015-06-11 |
JPWO2012096135A1 (ja) | 2014-06-09 |
EP2664642A1 (en) | 2013-11-20 |
JP5761204B2 (ja) | 2015-08-12 |
CN103282407A (zh) | 2013-09-04 |
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