JPH0149308B2 - - Google Patents
Info
- Publication number
- JPH0149308B2 JPH0149308B2 JP58205537A JP20553783A JPH0149308B2 JP H0149308 B2 JPH0149308 B2 JP H0149308B2 JP 58205537 A JP58205537 A JP 58205537A JP 20553783 A JP20553783 A JP 20553783A JP H0149308 B2 JPH0149308 B2 JP H0149308B2
- Authority
- JP
- Japan
- Prior art keywords
- weight
- parts
- adhesive
- copolymer
- vinylpyridine
- 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
- 229920001577 copolymer Polymers 0.000 claims description 26
- 239000000853 adhesive Substances 0.000 claims description 24
- 230000001070 adhesive effect Effects 0.000 claims description 24
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 18
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 18
- 239000004816 latex Substances 0.000 claims description 15
- 229920000126 latex Polymers 0.000 claims description 15
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 9
- KVBYPTUGEKVEIJ-UHFFFAOYSA-N benzene-1,3-diol;formaldehyde Chemical compound O=C.OC1=CC=CC(O)=C1 KVBYPTUGEKVEIJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 7
- 229920005989 resin Polymers 0.000 claims description 7
- 229920001971 elastomer Polymers 0.000 claims description 6
- 239000005060 rubber Substances 0.000 claims description 6
- 239000002245 particle Substances 0.000 claims description 3
- 239000000470 constituent Substances 0.000 claims 1
- 230000002787 reinforcement Effects 0.000 claims 1
- 230000007423 decrease Effects 0.000 description 10
- 239000000178 monomer Substances 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000012790 adhesive layer Substances 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical group CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical group CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BYLSIPUARIZAHZ-UHFFFAOYSA-N 2,4,6-tris(1-phenylethyl)phenol Chemical compound C=1C(C(C)C=2C=CC=CC=2)=C(O)C(C(C)C=2C=CC=CC=2)=CC=1C(C)C1=CC=CC=C1 BYLSIPUARIZAHZ-UHFFFAOYSA-N 0.000 description 1
- YQUDMNIUBTXLSX-UHFFFAOYSA-N 2-ethenyl-5-ethylpyridine Chemical compound CCC1=CC=C(C=C)N=C1 YQUDMNIUBTXLSX-UHFFFAOYSA-N 0.000 description 1
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 1
- VJOWMORERYNYON-UHFFFAOYSA-N 5-ethenyl-2-methylpyridine Chemical compound CC1=CC=C(C=C)C=N1 VJOWMORERYNYON-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 239000011258 core-shell material Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000010556 emulsion polymerization method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000011297 pine tar Substances 0.000 description 1
- 229940068124 pine tar Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000012783 reinforcing fiber Substances 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 238000010058 rubber compounding Methods 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
Landscapes
- Adhesives Or Adhesive Processes (AREA)
- Reinforced Plastic Materials (AREA)
- Moulding By Coating Moulds (AREA)
Description
【発明の詳細な説明】
本発明はビニルピリジンを含む乳化共重合体ラ
テツクスとレゾルシン−ホルマリン樹脂よりなる
ゴム補強用接着剤に関するものである。
本発明の目的はタイヤ、ベルト、ホースなどの
ゴム製品に含まれる補強用繊維とゴムの改良され
た接着剤を提供するものである。
現在、これらの繊維とゴムの接着にはすでにブ
タジエン−スチレン−ビニルピリジン共重合体ラ
テツクスとレゾルシン−ホルマリン樹脂からなる
接着剤が広く使用されている。その共重合体ラテ
ツクスの単量体組成もエマルジヨンラテツクスハ
ンドブツク（大成社発行第188頁）などから明ら
かな通り、ブタジエン70重量％、スチレン15重量
％、２−ビニルピリジン15重量％が一般的なもの
となつている。
本発明者らはこのビニルピリジンを含む共重合
体ラテツクスについて研究した結果優れた接着力
を有する接着剤を提供するものである。
本発明で使用する共重合体ラテツクスはブタジ
エン50〜90重量％、スチレン５〜45重量％、ビニ
ルピリジン５〜20重量％から成る共重合体50〜95
重量部とブタジエン５〜95重量％、スチレン５〜
95重量％から成る共重合体５〜50重量部から構成
され、それぞれ同一共重合体粒子中に存在する共
重合体ラテツクスである。
前者の共重合体においてブタジエンが50重量％
未満では接着剤層の弾性、低温屈撓性、接着性が
低下し、90重量％を越えると接着剤層の凝集が不
十分となり接着力が低下する。
ブタジエンの一部をイソプレン、クロロプレン
などの共役ジエン系単量体の１種もしくは、２種
以上に代替することもできる。
スチレンが５重量％未満では接着力が低下し、
45重量％を越えると接着剤層の弾性、低温の屈撓
性が低下する。またスチレンの一部をα−メチル
スチレン、４−ビニルトルエン、アクリロニトリ
ルに代替することもできる。
ビニルピリジンが５重量％未満では良好な接着
力は得られず、20重量％を越えると接着剤層の弾
性、低温屈撓性が低下し、好ましくない。
本発明のビニルピリジンとは、２−ビニルピリ
ジン、５−エチル−２ビニルピリジン、２−メチ
ル−５−ビニルピリジン、４−ビニルピリジンな
どであり、これらは一種または二種以上で用いら
れるが、特に２−ビニルピリジンが好ましい。
これらの単量体から成る共重合体は50重量部未
満および95重量部を越えると接着力が低下する。
また後者の共重合体においてブタジエンが５重
量％未満では接着剤層の弾性、低温屈撓性、接着
力が低下する。また95重量％を越えると接着強度
が劣る。
ブタジエンの一部をイソプレン、クロロプレン
などの共役ジエン系単量体の一種または二種以上
に代替することもできる。
スチレンが５重量％未満では接着力が低下し、
95重量％を越えると接着剤層の弾性、低温の屈撓
性が低下する。またスチレンの一部をα−メチル
スチレン、４−ビニルトルエン、アクリロニトリ
ルに代替することもできる。
これらの単量体から成る共重合体は５重量部未
満でも50重量部を越えても接着力が低下する。以
上の共重合体は一つの共重合体粒子に存在してお
り、その形態はコアーシエル（多層）構造、サラ
ミ状構践、網目状構造、極在化構造を有するも
の、あるいはこれらの組合せ構造があげられる。
これらの異質構造を有する共重合体ラテツクスは
二段階以上の多段階乳化重合法が適しているが、
二種以上の重合方法を組合せても良い。
得られた乳化共重合体ラテツクスはレゾルシン
−ホルマリン樹脂と混合されて接着剤となるが本
発明の乳化共重合体ラテツクスの一部をスチレン
−ブタジエン共重合体ラテツクスに代替しても本
発明を達成できる。
乳化共重合体ラテツクス100重量部に対してレ
ゾルシン−ホルマリン樹脂が10〜30重量部で用い
られて接着剤となるが、レゾルシン−ホルマリン
樹脂が10重量部未満では接着力が劣り、30重量部
を越えると繊維が硬くなりすぎる。
本発明の接着剤は通常繊維100重量部に対して
２〜８重量部で用いられる。
２重量部未満では接着力が劣り、８重量部を越
えると耐被労性が劣る。
以下に実施例を示すが、本発明は実施例によつ
て何ら制限されない。
なお実施例中の部はすべて重量部を表わす。
実施例 １
水130部にロジン酸カリウム4.0部およびナフタ
レンスルホン酸ナトリウムホルマリン縮合部1.0
部、水酸化ナトリウム0.5部を加え溶解させる。
これに表−１に示した第１段目単量体80部を添加
しさらにｔ−ドデシルメルカプタン0.5部を加え
て乳化させる。過硫酸カリウム0.5部を加え、全
体を50℃に保つて重合を行つた。１段目単量体混
合物の転化率が80〜90％に達したのち、第２段目
単量体混合物をｔ−ドデシルメルカプタン0.1部
を添加し重合を続ける。
最終の転化率が90〜95％となればハイドロキノ
ン0.1部を加え重合を停止し、減圧によつて未反
応モノマーを除去することにより、共重合体ラテ
ツクスが得られた。
比較例５は上記方法の一段目の重合方法で転化
率が90％になるまで重合を行い、重合を停止し
た。未反応モノマーを除去し共重合体ラテツクス
を得た。
得られた共重合体ラテツクス100重量部と水239
部に水酸化ナトリウム0.3部、レゾルシン11.0部、
37％ホルマリン16.2部を加え、25℃にて６時間熟
成することにより得たレゾルシンホルマリン樹脂
18部を混合し固形分20％に調整して更に25℃で18
時間熟成し接着剤を得た。
得られた接着剤に1890D／２のナイロンタイヤ
コードを含浸した。
次いで150℃で３分間熱処理を行つた。接着剤
の付着率は４％であつた。接着剤処理したナイロ
ンタイヤコードは次の配合ゴムを用いて
ASTMD−2138−72（Ｈ−Pull Test法）により
接着力を測定し結果を表−１に示す。
配合ゴム処方
天然ゴム 100部
SRFカーボン 20
FEFカーボン 20
パインタール ５
スチレン化フエノール ２
ステアリン酸 2.5
亜鉛華 ５
加硫促進剤* 1.0
イオウ 3.0
＊ Ｎ−シクロヘキシル−２−ベンゾチアジル
ースルフエンアミド
【表】DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a rubber reinforcing adhesive comprising an emulsion copolymer latex containing vinylpyridine and a resorcinol-formalin resin. An object of the present invention is to provide an improved adhesive for reinforcing fibers and rubber contained in rubber products such as tires, belts, hoses, etc. At present, adhesives made of butadiene-styrene-vinylpyridine copolymer latex and resorcinol-formalin resin are already widely used for bonding these fibers and rubber. The monomer composition of the copolymer latex is generally 70% by weight of butadiene, 15% by weight of styrene, and 15% by weight of 2-vinylpyridine, as is clear from the Emulsion Latex Handbook (Page 188, published by Taiseisha). It has become a thing. The present inventors have conducted research on this vinylpyridine-containing copolymer latex, and as a result, have provided an adhesive having excellent adhesive strength. The copolymer latex used in the present invention is a copolymer consisting of 50 to 90% by weight of butadiene, 5 to 45% by weight of styrene, and 5 to 20% by weight of vinylpyridine.
Parts by weight, butadiene 5-95% by weight, styrene 5-95% by weight
It is a copolymer latex composed of 5 to 50 parts by weight of a 95% by weight copolymer, each present in the same copolymer particles. Butadiene is 50% by weight in the former copolymer.
If it is less than 90% by weight, the elasticity, low-temperature flexibility, and adhesiveness of the adhesive layer will decrease, and if it exceeds 90% by weight, the cohesion of the adhesive layer will be insufficient and the adhesive force will decrease. A part of butadiene can also be replaced with one or more conjugated diene monomers such as isoprene and chloroprene. If the styrene content is less than 5% by weight, the adhesive strength will decrease,
If it exceeds 45% by weight, the elasticity and low-temperature flexibility of the adhesive layer will decrease. Moreover, a part of styrene can also be replaced with α-methylstyrene, 4-vinyltoluene, or acrylonitrile. If the vinylpyridine content is less than 5% by weight, good adhesive strength cannot be obtained, and if it exceeds 20% by weight, the elasticity and low-temperature flexibility of the adhesive layer will decrease, which is not preferable. The vinylpyridine of the present invention includes 2-vinylpyridine, 5-ethyl-2vinylpyridine, 2-methyl-5-vinylpyridine, 4-vinylpyridine, etc., and these may be used alone or in combination of two or more, but 2-vinylpyridine is particularly preferred. If the amount of the copolymer made of these monomers is less than 50 parts by weight or more than 95 parts by weight, the adhesive strength will decrease. If the latter copolymer contains less than 5% by weight of butadiene, the elasticity, low-temperature flexibility, and adhesive strength of the adhesive layer will decrease. Moreover, if it exceeds 95% by weight, the adhesive strength will be poor. A part of butadiene can also be replaced with one or more conjugated diene monomers such as isoprene and chloroprene. If the styrene content is less than 5% by weight, the adhesive strength will decrease,
If it exceeds 95% by weight, the elasticity and low-temperature flexibility of the adhesive layer will decrease. Moreover, a part of styrene can also be replaced with α-methylstyrene, 4-vinyltoluene, or acrylonitrile. The adhesive strength of copolymers made of these monomers decreases even if the amount is less than 5 parts by weight or exceeds 50 parts by weight. The above copolymers exist in one copolymer particle, and the morphology thereof may be a core-shell (multilayer) structure, a salami-like structure, a network structure, a localized structure, or a combination of these structures. can give.
A multi-step emulsion polymerization method with two or more steps is suitable for these copolymer latexes with a heterogeneous structure.
Two or more types of polymerization methods may be combined. The obtained emulsion copolymer latex is mixed with a resorcinol-formalin resin to form an adhesive, but the present invention can also be achieved by substituting a part of the emulsion copolymer latex of the present invention with a styrene-butadiene copolymer latex. can. Resorcinol-formalin resin is used in an amount of 10 to 30 parts by weight per 100 parts by weight of the emulsified copolymer latex to form an adhesive. However, if the resorcinol-formalin resin is less than 10 parts by weight, the adhesive strength is poor, so 30 parts by weight is used. If it exceeds the limit, the fibers will become too hard. The adhesive of the present invention is usually used in an amount of 2 to 8 parts by weight per 100 parts by weight of fibers. If it is less than 2 parts by weight, the adhesive strength will be poor, and if it exceeds 8 parts by weight, the stress resistance will be poor. Examples are shown below, but the present invention is not limited by the examples. Note that all parts in the examples represent parts by weight. Example 1 4.0 parts of potassium rosinate and 1.0 part of formalin condensation of sodium naphthalene sulfonate in 130 parts of water
1 part and 0.5 part of sodium hydroxide and dissolve.
To this was added 80 parts of the first stage monomer shown in Table 1, and further 0.5 part of t-dodecyl mercaptan was added for emulsification. 0.5 part of potassium persulfate was added, and the whole was kept at 50°C for polymerization. After the conversion of the first-stage monomer mixture reaches 80 to 90%, 0.1 part of t-dodecyl mercaptan is added to the second-stage monomer mixture to continue polymerization. When the final conversion rate reached 90 to 95%, 0.1 part of hydroquinone was added to stop the polymerization, and unreacted monomers were removed under reduced pressure to obtain a copolymer latex. In Comparative Example 5, polymerization was carried out using the first stage polymerization method of the above method until the conversion rate reached 90%, and then the polymerization was stopped. Unreacted monomers were removed to obtain a copolymer latex. 100 parts by weight of the obtained copolymer latex and 239 parts by weight of water
0.3 parts of sodium hydroxide, 11.0 parts of resorcinol,
Resorcin formalin resin obtained by adding 16.2 parts of 37% formalin and aging at 25°C for 6 hours.
Mix 18 parts, adjust the solid content to 20%, and further heat at 25℃ for 18
After time aging, an adhesive was obtained. The resulting adhesive was impregnated with 1890D/2 nylon tire cord. Next, heat treatment was performed at 150°C for 3 minutes. The adhesion rate of the adhesive was 4%. Adhesive-treated nylon tire cord is made using the following compounded rubber.
The adhesive strength was measured according to ASTMD-2138-72 (H-Pull Test method) and the results are shown in Table-1. Compounded rubber formulation Natural rubber 100 parts SRF carbon 20 FEF carbon 20 Pine tar 5 Styrenated phenol 2 Stearic acid 2.5 Zinc white 5 Vulcanization accelerator * 1.0 Sulfur 3.0 * N-Cyclohexyl-2-benzothiazirusulphenamide [Table]
Claims (1)
ぞれ同一共重合体粒子中に存在する共重合体
ラテツクス (2) レゾルシン・ホルマリン樹脂 を主要構成成分とするゴム補強用接着剤。[Scope of Claims] 1 (1) (A) 50 to 95 parts by weight of a copolymer composed of 50 to 90% by weight of butadiene, 5 to 45% by weight of styrene, 5 to 20% by weight of vinylpyridine, and (B) butadiene 5 Copolymer latex in which 5 to 50 parts by weight of a copolymer composed of ~95% by weight styrene is present in each copolymer particle (2) Main constituents are resorcinol formalin resin Adhesive for rubber reinforcement.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58205537A JPS6096674A (en) | 1983-10-31 | 1983-10-31 | Rubber reinforcement adhesive |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58205537A JPS6096674A (en) | 1983-10-31 | 1983-10-31 | Rubber reinforcement adhesive |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6096674A JPS6096674A (en) | 1985-05-30 |
| JPH0149308B2 true JPH0149308B2 (en) | 1989-10-24 |
Family
ID=16508528
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58205537A Granted JPS6096674A (en) | 1983-10-31 | 1983-10-31 | Rubber reinforcement adhesive |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6096674A (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0699869B2 (en) * | 1986-08-07 | 1994-12-07 | 日本ゼオン株式会社 | Method for producing rubber-reinforced polyester fiber |
| JPH0674401B2 (en) * | 1986-08-28 | 1994-09-21 | 住友ダウ株式会社 | Adhesive composition for bonding rubber and fiber |
| JP2007046210A (en) * | 2005-08-12 | 2007-02-22 | Teijin Techno Products Ltd | Method for producing rubber reinforcing fiber |
| KR101650607B1 (en) | 2009-04-28 | 2016-08-23 | 가부시키가이샤 브리지스톤 | Adhesive composition for organic fiber cords, rubber-reinforcing material using same, tire and bonding method |
| EP2504406B1 (en) * | 2009-11-24 | 2015-05-06 | Omnova Solutions Inc. | Rubber adhesive compositions containing vinyl pyridine latex polymers with alternate nitrogen monomers |
| EP4074799A4 (en) | 2019-12-09 | 2023-05-24 | Bridgestone Corporation | ADHESIVE COMPOSITION, COMPOSITE RUBBER/ORGANIC FIBER CABLE, AND TIRE |
| WO2021256149A1 (en) | 2020-06-19 | 2021-12-23 | デンカ株式会社 | Adhesive composition for organic fiber cord, rubber reinforcing material and method for producing same, and rubber article |
| EP4265699A4 (en) | 2020-12-15 | 2024-06-19 | Bridgestone Corporation | Adhesive composition, rubber-organic fiber cord composite, and tire |
-
1983
- 1983-10-31 JP JP58205537A patent/JPS6096674A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6096674A (en) | 1985-05-30 |
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