JPS6313443B2 - - Google Patents
Info
- Publication number
- JPS6313443B2 JPS6313443B2 JP58229945A JP22994583A JPS6313443B2 JP S6313443 B2 JPS6313443 B2 JP S6313443B2 JP 58229945 A JP58229945 A JP 58229945A JP 22994583 A JP22994583 A JP 22994583A JP S6313443 B2 JPS6313443 B2 JP S6313443B2
- Authority
- JP
- Japan
- Prior art keywords
- modifier
- phenolic resin
- hydroxyl group
- phenolic
- compound
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 239000005011 phenolic resin Substances 0.000 claims description 22
- 229920001568 phenolic resin Polymers 0.000 claims description 21
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 17
- 239000007788 liquid Substances 0.000 claims description 15
- 239000003607 modifier Substances 0.000 claims description 15
- -1 isocyanate compound Chemical class 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 150000001993 dienes Chemical class 0.000 claims description 9
- 239000012948 isocyanate Substances 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 8
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 6
- 239000005062 Polybutadiene Substances 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 229920002857 polybutadiene Polymers 0.000 claims description 4
- 238000004080 punching Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 229920000459 Nitrile rubber Polymers 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000005452 bending Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 2
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 238000010494 dissociation reaction Methods 0.000 description 2
- 230000005593 dissociations Effects 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 229920003987 resole Polymers 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000000051 modifying effect Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Description
【発明の詳細な説明】
本発明はフエノール系樹脂の変性剤に関し、詳
しくはフエノール系樹脂に可撓性を付与し、かつ
低温加工性等を向上させる、フエノール系樹脂の
変性剤に関する。
フエノール系樹脂は機械的強度が大きく、寸法
安定性、電気絶縁性に優れ、また化学薬品に対し
て安定であるため、従来より種々の弱電機器用材
料などとして用いられている。
ところで、弱電機器用として作製される薄層の
銅張積層板に抵抗ダイオードなどの部品を自動挿
入する場合、その打抜き寸法精度向上のため低温
で打抜加工が行なわれる。そのため、この積層板
として用いられる樹脂は打抜加工性が要求され
る。
しかるに、フエノール系樹脂は硬くて脆いとい
う欠点を有しており、極めて打抜加工性が悪いも
のであつた。
そこで、フエノール系樹脂の硬くて脆いという
性質を変性して可撓性を付与し、加工時の衝撃に
耐え得るようにするために、従来はフエノール系
樹脂に植物油や液状アクリロニトリル−ブタジエ
ンゴムを添加配合することが行なわれていた。し
かし、このようにして変性したフエノール樹脂の
打抜加工性は十分でなく、また曲げ強度も満足す
べきものでなかつた。
そこで、本発明者らは打抜加工性、曲げ強度な
どのフエノール系樹脂の諸物性を向上させる変性
剤を開発すべく検討した結果、特定の化合物をフ
エノール系樹脂に添加することにより目的とする
変性効果が達成されることを見出し、この知見に
基いて本発明を完成した。
すなわち、本発明は水酸基を含有する液状ジエ
ン系重合体とトリレンジイソシアネートとの反応
により得られるイソシアネート化合物とフエノー
ル系化合物との反応生成物からなるフエノール系
樹脂の変性剤である。
本発明に用いるイソシアネート化合物とは、後
記するフエノール系化合物のフエノール性水酸基
と反応するイソシアネート基を有する化合物を意
味し、水酸基含有液状ジエン系重合体とトリレン
ジイソシアネートとの反応生成物が用いられる。
水酸基含有液状ジエン系重合体とは、炭素数４
〜12のジエン重合体、ジエン共重合体であり、具
体的にはブタジエンホモポリマー、ブタジエン−
スチレンコポリマー、ブタジエン−イソプレンコ
ポリマー、ブタジエン−アクリロニトリルコポリ
マー、ブタジエン−２−エチルヘキシルアクリレ
ートコポリマー、ブタジエン−ｎ−オクタデシル
アクリレートコポリマーなどがある。これらは数
平均分子量が300〜25000、好ましくは500〜10000
である。これら液状ジエン系重合体は、たとえば
液状反応媒体中で共役ジエンモノマーを過酸化水
素の存在下加熱反応させることによつて製造する
ことができる。このようにして得られた液状ジエ
ン系重合体は官能基としての水酸基を平均1.7〜
3.0含有するものである。
本発明において、フエノール系化合物は上記の
イソシアネート化合物と反応してそのイソシアネ
ート基を封鎖するために用いられるものである。
したがつて、フエノール系化合物としては該イソ
シアネート基と反応しうるフエノール性水酸基を
含むものであればよく、たとえばフエノール、ｏ
−クレゾール、ｍ−クレゾール、ｐ−クレゾー
ル、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、ｐ−sec.−ブチルフエノール、ｐ−tert−ブ
チルフエノール、レゾルシン、オキシベンゼン−
ｐ−スルホン酸などがある。
上記のイソシアネート化合物とフエノール系化
合物との反応は常法により行なえばよく、反応生
成物たるイソシアネート化合物のフエノール封鎖
体がフエノール系樹脂の変性剤となるのである。
本発明の好適な変性剤は水酸基を含有する液状ポ
リブタジエンとトリレンジイソシアネートとの反
応により得られるイソシアネート化合物をフエノ
ール系化合物と反応させることによられるイソシ
アネート化合物のフエノール封鎖体である。
本発明のフエノール系樹脂変性剤はフエノール
系樹脂に対して0.5〜35重量％、好ましくは５〜
30重量％の割合で添加する。ここでフエノール系
樹脂はフエノール類とホルマリンから製造される
ものであり、ノボラツク樹脂およびレゾール樹脂
のいずれであつてもよいが、比較的低分子量のも
のが好適に用いられる。
フエノール系樹脂に上記変性剤を添加したのち
硬化させてフエノール系樹脂の硬化体を得る。硬
化反応は通常、60〜250℃、好ましくは120〜210
℃の温度、５〜200Kg／cm2、好ましくは50〜120
Kg／cm2の圧力にて0.1〜10時間、好ましくは0.3〜
２時間の条件にて行なう。また、本発明のフエノ
ール系樹脂の変性剤は解離触媒として（１，８−
ジアザ−ビシクロ｛５，４，０｝ウンデセン−
７）などを使用することによつて解離温度を低下
させ、硬化反応を促進することができる。
このようにして得られるフエノール系樹脂硬化
体は可撓性を有しているため、低温加工性にすぐ
れ、弱電機器用材料などに用いる場合に要求され
る打抜加工性を十分に満足している。その上、フ
エノール樹脂が本来的に有している機械的強度、
とりわけ曲げ強度が大きく、寸法安定性等にもす
ぐれている。したがつて、本発明の変性剤によつ
て改質されたフエノール系樹脂は弱電機器用材料
など可撓性が必要とされる分野に極めて有用であ
る。
次に、本発明の実施例を示す。
製造例 １
（HTP−9BKの製造）
末端に水酸基を含有する液状ポリブタジエン
（出光石油化学(株)製、Ｒ−45HT、水酸基当量
0.75meq／ｇ）100ｇを300ml丸底フラスコに入
れ、80℃で１時間、１mmHg下で真空脱泡した後、
25℃に冷却した。次いで、トリレンジイソシアネ
ート30.9ｇを加え、25℃で１時間撹拌した。さら
に、80℃で６時間加熱撹拌して液状ポリブタジエ
ンとトリレンジイソシアネートプレポリマー（遊
離イソシアネート９％）を得た。
次に、このプレポリマー100ｇを200ml丸底フラ
スコにとり、これを60℃に加温し、フエノール
20.2ｇを加えて３時間で60℃撹拌して変性剤
（HTP−9BK）を得た。
製造例 ２
（液状NBRの製造）
１のオートクレーブにイソプロピルアルコー
ル200ｇ、50％H2O215.75ｇ、ブタジエン235ｇお
よびアクリロニトリル80ｇを入れ、反応圧13Kg／
cm2、温度110℃で90分間反応を行ない変性剤（液
状NBR）を得た。
実施例１〜５および比較例１〜３
第１表に示す所定量のクレゾールレゾールワニ
ス（メタノール28.5重量％、トルエン25.0重量
％、不揮発分46.5重量％）および変性剤を混合
し、この混合物をコツトンリンター紙に含浸させ
た後、乾燥して樹脂含有量55重量％の半硬化体を
得た。得られたプリプレグを６枚重ねて温度180
℃、圧力70Kg／cm2の条件にて１時間処理して硬化
させ、厚さ２mmの積層板を作製した。混合物の組
成および積層板について評価結果を第１表に示
す。
【表】DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a modifier for phenolic resins, and more particularly to a modifier for phenolic resins that imparts flexibility to phenolic resins and improves low-temperature processability. Phenol resins have high mechanical strength, excellent dimensional stability and electrical insulation, and are stable against chemicals, so they have been used as materials for various light electrical devices. By the way, when parts such as resistance diodes are automatically inserted into thin copper-clad laminates manufactured for use in light electrical equipment, punching is performed at low temperatures in order to improve the precision of the punching dimensions. Therefore, the resin used for this laminate is required to have good punching workability. However, phenolic resins have the disadvantage of being hard and brittle, and have extremely poor punching properties. Therefore, conventionally, vegetable oil or liquid acrylonitrile-butadiene rubber was added to phenolic resin in order to modify the hard and brittle properties of phenolic resin and make it more flexible and able to withstand impact during processing. Blending was done. However, the punching workability of the phenolic resin modified in this way was not sufficient, and the bending strength was also not satisfactory. Therefore, the present inventors investigated to develop a modifier that improves various physical properties of phenolic resin, such as punching workability and bending strength, and found that by adding a specific compound to phenolic resin, the objective could be achieved. It was discovered that a modifying effect was achieved, and the present invention was completed based on this knowledge. That is, the present invention is a phenolic resin modifier comprising a reaction product of a phenol compound and an isocyanate compound obtained by reacting a liquid diene polymer containing a hydroxyl group with tolylene diisocyanate. The isocyanate compound used in the present invention refers to a compound having an isocyanate group that reacts with the phenolic hydroxyl group of a phenolic compound described later, and a reaction product of a hydroxyl group-containing liquid diene polymer and tolylene diisocyanate is used. A hydroxyl group-containing liquid diene polymer has 4 carbon atoms.
~12 diene polymers and diene copolymers, specifically butadiene homopolymer, butadiene-
Examples include styrene copolymer, butadiene-isoprene copolymer, butadiene-acrylonitrile copolymer, butadiene-2-ethylhexyl acrylate copolymer, butadiene-n-octadecyl acrylate copolymer. These have a number average molecular weight of 300 to 25,000, preferably 500 to 10,000.
It is. These liquid diene polymers can be produced, for example, by subjecting a conjugated diene monomer to a heating reaction in the presence of hydrogen peroxide in a liquid reaction medium. The liquid diene polymer thus obtained has an average of 1.7 to 1.7 hydroxyl groups as functional groups.
Contains 3.0. In the present invention, the phenol compound is used to react with the above-mentioned isocyanate compound to block its isocyanate groups.
Therefore, the phenolic compound may be any compound containing a phenolic hydroxyl group that can react with the isocyanate group, such as phenol, o
-Cresol, m-cresol, p-cresol, 2,3-xylenol, 2,4-xylenol, 2,5-xylenol, 2,6-xylenol, 3,4-xylenol, 3,5-xylenol, p-sec .-Butylphenol, p-tert-butylphenol, resorcinol, oxybenzene-
Examples include p-sulfonic acid. The reaction between the above-mentioned isocyanate compound and phenol compound may be carried out by a conventional method, and the phenol capped product of the isocyanate compound as a reaction product becomes a modifier for the phenolic resin.
A preferred modifier of the present invention is a phenol-blocked isocyanate compound obtained by reacting an isocyanate compound obtained by reacting a hydroxyl group-containing liquid polybutadiene with tolylene diisocyanate with a phenolic compound. The phenolic resin modifier of the present invention is 0.5 to 35% by weight, preferably 5 to 35% by weight based on the phenolic resin.
Add at a rate of 30% by weight. Here, the phenolic resin is produced from phenols and formalin, and may be either a novolak resin or a resol resin, but one with a relatively low molecular weight is preferably used. The above modifier is added to the phenolic resin and then cured to obtain a cured product of the phenolic resin. Curing reaction is usually 60-250℃, preferably 120-210℃
Temperature in °C, 5-200Kg/ cm2 , preferably 50-120
0.1-10 hours at a pressure of Kg/ cm2 , preferably 0.3-10 hours
It is carried out under the conditions of 2 hours. In addition, the modifier for the phenolic resin of the present invention is used as a dissociation catalyst (1,8-
Diaza-bicyclo{5,4,0}undecene-
By using 7), etc., the dissociation temperature can be lowered and the curing reaction can be promoted. The cured phenolic resin obtained in this way has flexibility, so it has excellent low-temperature processability and satisfies the punching processability required when used as a material for light electrical equipment. There is. Moreover, the inherent mechanical strength of phenolic resin,
In particular, it has high bending strength and excellent dimensional stability. Therefore, the phenolic resin modified with the modifier of the present invention is extremely useful in fields where flexibility is required, such as materials for light electrical equipment. Next, examples of the present invention will be shown. Production example 1 (Production of HTP-9BK) Liquid polybutadiene containing a hydroxyl group at the end (manufactured by Idemitsu Petrochemical Co., Ltd., R-45HT, hydroxyl group equivalent
0.75meq/g) was placed in a 300ml round bottom flask and degassed under vacuum at 80℃ for 1 hour under 1mmHg.
Cooled to 25°C. Next, 30.9 g of tolylene diisocyanate was added and stirred at 25°C for 1 hour. Further, the mixture was heated and stirred at 80° C. for 6 hours to obtain liquid polybutadiene and tolylene diisocyanate prepolymer (9% free isocyanate). Next, 100 g of this prepolymer was placed in a 200 ml round bottom flask, heated to 60°C, and the phenol
20.2g was added and stirred at 60°C for 3 hours to obtain a modifier (HTP-9BK). Production example 2 (Production of liquid NBR) 200 g of isopropyl alcohol, 15.75 g of 50% H 2 O 2 , 235 g of butadiene and 80 g of acrylonitrile were placed in the autoclave 1, and the reaction pressure was 13 kg/
cm 2 and a temperature of 110° C. for 90 minutes to obtain a modifier (liquid NBR). Examples 1 to 5 and Comparative Examples 1 to 3 A predetermined amount of cresol resol varnish shown in Table 1 (methanol 28.5% by weight, toluene 25.0% by weight, non-volatile content 46.5% by weight) and a modifier were mixed, and this mixture was mixed. After impregnating Tonlinter paper with the mixture, it was dried to obtain a semi-cured product with a resin content of 55% by weight. 6 sheets of the obtained prepreg were stacked and heated to a temperature of 180.
℃ and a pressure of 70 Kg/cm 2 for 1 hour to harden, thereby producing a laminate with a thickness of 2 mm. Table 1 shows the evaluation results regarding the composition of the mixture and the laminate. 【table】
Claims (1)
レンジイソシアネートとの反応により得られるイ
ソシアネート化合物とフエノール系化合物との反
応生成物からなるフエノール系樹脂の変性剤。 ２ 水酸基を含有する液状ジエン系重合体が末端
水酸基含有液状ポリブタジエンである特許請求の
範囲第１項記載の変性剤。[Scope of Claims] 1. A phenolic resin modifier comprising a reaction product of an isocyanate compound obtained by reacting a hydroxyl group-containing liquid diene polymer with tolylene diisocyanate and a phenol compound. 2. The modifier according to claim 1, wherein the liquid diene polymer containing a hydroxyl group is a liquid polybutadiene containing a terminal hydroxyl group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58229945A JPS60123522A (en) | 1983-12-07 | 1983-12-07 | Modifying agent for phenolic resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58229945A JPS60123522A (en) | 1983-12-07 | 1983-12-07 | Modifying agent for phenolic resin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60123522A JPS60123522A (en) | 1985-07-02 |
| JPS6313443B2 true JPS6313443B2 (en) | 1988-03-25 |
Family
ID=16900178
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58229945A Granted JPS60123522A (en) | 1983-12-07 | 1983-12-07 | Modifying agent for phenolic resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60123522A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0806170B1 (en) * | 2007-10-22 | 2019-02-26 | Bridgestone Corporation | FUNCTIONALIZED POLYMER, METHOD FOR PREPARING A FUNCTIONALIZED POLYMER, AND COMPOSITION UNDERSTANDING A FUNCTIONALIZED POLYMER |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4911278A (en) * | 1972-05-29 | 1974-01-31 | ||
| JPS5811559A (en) * | 1981-07-13 | 1983-01-22 | Sanyo Chem Ind Ltd | Primer composition |
-
1983
- 1983-12-07 JP JP58229945A patent/JPS60123522A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4911278A (en) * | 1972-05-29 | 1974-01-31 | ||
| JPS5811559A (en) * | 1981-07-13 | 1983-01-22 | Sanyo Chem Ind Ltd | Primer composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60123522A (en) | 1985-07-02 |
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