JP5677942B2 - 有機繊維コード用接着剤組成物、並びにそれを用いたゴム補強材、タイヤおよび接着方法 - Google Patents
有機繊維コード用接着剤組成物、並びにそれを用いたゴム補強材、タイヤおよび接着方法 Download PDFInfo
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- JP5677942B2 JP5677942B2 JP2011511385A JP2011511385A JP5677942B2 JP 5677942 B2 JP5677942 B2 JP 5677942B2 JP 2011511385 A JP2011511385 A JP 2011511385A JP 2011511385 A JP2011511385 A JP 2011511385A JP 5677942 B2 JP5677942 B2 JP 5677942B2
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- organic fiber
- rubber
- fiber cord
- mass
- adhesive composition
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- 239000000853 adhesive Substances 0.000 title claims description 80
- 230000001070 adhesive effect Effects 0.000 title claims description 80
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- 239000005060 rubber Substances 0.000 title claims description 61
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- 238000000034 method Methods 0.000 title claims description 19
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- -1 isocyanate compound Chemical class 0.000 claims description 39
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- 239000003795 chemical substances by application Substances 0.000 claims description 27
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 27
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- 244000043261 Hevea brasiliensis Species 0.000 description 2
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- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
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- 239000000600 sorbitol Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
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- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 2
- 229960002447 thiram Drugs 0.000 description 2
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- OEVVKKAVYQFQNV-UHFFFAOYSA-N 1-ethenyl-2,4-dimethylbenzene Chemical compound CC1=CC=C(C=C)C(C)=C1 OEVVKKAVYQFQNV-UHFFFAOYSA-N 0.000 description 1
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- FCMUPMSEVHVOSE-UHFFFAOYSA-N 2,3-bis(ethenyl)pyridine Chemical compound C=CC1=CC=CN=C1C=C FCMUPMSEVHVOSE-UHFFFAOYSA-N 0.000 description 1
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
- SEFYJVFBMNOLBK-UHFFFAOYSA-N 2-[2-[2-(oxiran-2-ylmethoxy)ethoxy]ethoxymethyl]oxirane Chemical compound C1OC1COCCOCCOCC1CO1 SEFYJVFBMNOLBK-UHFFFAOYSA-N 0.000 description 1
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
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- CPGFMWPQXUXQRX-UHFFFAOYSA-N 3-amino-3-(4-fluorophenyl)propanoic acid Chemical compound OC(=O)CC(N)C1=CC=C(F)C=C1 CPGFMWPQXUXQRX-UHFFFAOYSA-N 0.000 description 1
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- NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 description 1
- JTHGIRIGZAGNOX-UHFFFAOYSA-N 4-pentan-2-ylphenol Chemical compound CCCC(C)C1=CC=C(O)C=C1 JTHGIRIGZAGNOX-UHFFFAOYSA-N 0.000 description 1
- ZUTYZAFDFLLILI-UHFFFAOYSA-N 4-sec-Butylphenol Chemical compound CCC(C)C1=CC=C(O)C=C1 ZUTYZAFDFLLILI-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
- VJOWMORERYNYON-UHFFFAOYSA-N 5-ethenyl-2-methylpyridine Chemical compound CC1=CC=C(C=C)C=N1 VJOWMORERYNYON-UHFFFAOYSA-N 0.000 description 1
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- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
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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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/58—Epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
- C08J5/06—Reinforcing macromolecular compounds with loose or coherent fibrous material using pretreated fibrous materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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Description
本発明の有機繊維コード用接着剤組成物は、(ブロックド)イソシアネート化合物および/またはアミン系硬化剤(A)と、エポキシ化合物(B)と、ゴムラテックス(C)と、を含むものである。これにより、有機繊維コードとゴムとの接着の過程において、レゾルシンおよびホルマリンを実質的に使用せずに、一浴で同等以上の接着力を得ることができる。また、本発明の接着剤組成物は、ポリエステル樹脂やアラミド樹脂など接着が難しい有機繊維コードに適用する場合であっても、エポキシ樹脂による前処理をすることなく使用できる。本発明の有機繊維コード用接着剤組成物がエポキシ化合物(B)を含まないと、接着剤組成物の有機繊維コード表面への吸着が不十分となって、有機繊維コードと接着剤組成物との間の接着性が低下する。また、(ブロックド)イソシアネート化合物は接着剤組成物の架橋密度を向上させる効果があり、本発明の接着剤組成物が(ブロックド)イソシアネート化合物を含まないと、接着剤組成物の強度が低下することにより、やはり接着性が低下する。一方、アミン系硬化剤は、エポキシ化合物の硬化速度を速める効果があり、これにより、有機繊維コードと接着剤組成物との間の接着性を向上させることができる。
(実施例1〜13、参考例1〜9および比較例1,2)
ポリエステルのタイヤコード(ポリエステル製、1670dtex/2、撚り数39×39/10cm:2本の1670dtexのポリエステル繊維を、撚り数39×39/10cmで撚ったもの)を準備した。下記表中に示す配合で、各実施例、参考例および比較例の接着剤を作製し、該接着剤を20質量%含む接着剤水溶液を調製した。接着剤水溶液に、準備したタイヤコードを浸漬して引き上げ、タイヤコードに接着剤水溶液を付着させた。
得られた接着剤の接着力を、JIS K6301に従って評価した。接着力は、従来例の接着力を100とした指数で示し、数値が大なるほど結果が良好である。結果を下記表1に併記する。
※2)アミン系硬化剤(東京化成工業(株)製、ピペラジン(無水物))
※3)エポキシ化合物(ナガセ化成工業(株)製、「デナコールEX614B」、ソルビトール・ポリグリシジルエーテル)
※4)ビニルピリジン−スチレン−ブタジエン共重合体ラテックス(Vpラテックス、固形分濃度=41質量%、住友A&L(株)製、PYLATEX)
Claims (9)
- 有機繊維が撚糸されてなるタイヤ補強用の有機繊維コードを、(ブロックド)イソシアネート化合物および/またはアミン系硬化剤(A)と、エポキシ化合物(B)と、ゴムラテックス(C)と、を含み、レゾルシンおよびホルマリンを含まない有機繊維コード用接着剤組成物で被覆して接着剤層を形成して、前記有機繊維コードとゴムとを前記有機繊維コード用接着剤組成物のみを介して接着するにあたり、前記ゴムラテックス(C)として、(i)スチレン含有率30〜60質量%、ブタジエン含有率60質量%未満およびビニルピリジン含有率0.5〜15質量%で構成される単量体混合物を重合させた後、(ii)引き続いてスチレン含有率10〜40質量%、ブタジエン含有率45〜75質量%およびビニルピリジン含有率5〜20質量%で構成される単量体混合物を、前記(i)における重合で用いたスチレン含有率よりも低いスチレン含有率で重合させて得られる、二重構造を有するビニルピリジン−スチレン−ブタジエン系共重合体ラテックスを用いることを特徴とする接着方法。
- 前記有機繊維コードを前記有機繊維コード用接着剤組成物に含浸して、前記接着剤層を形成する請求項1記載の接着方法。
- 前記有機繊維コードの表面に前記接着剤層を形成後、該有機繊維コードに乾燥処理および加熱処理を施し、さらに、該有機繊維コードを未加硫ゴムに埋設し、該未加硫ゴムを加硫処理して、前記有機繊維コードとゴムとを前記有機繊維コード用接着剤組成物を介して接着する請求項1記載の接着方法。
- 前記有機繊維コードとして、ポリエステルまたはナイロンからなるものを用いる請求項1記載の接着方法。
- 有機繊維が撚糸されてなるタイヤ補強用の有機繊維コードと、該有機繊維コードを被覆するゴムとからなるゴム補強材であって、前記有機繊維コードと前記ゴムとが、(ブロックド)イソシアネート化合物および/またはアミン系硬化剤(A)と、エポキシ化合物(B)と、ゴムラテックス(C)と、を含み、レゾルシンおよびホルマリンを含まない有機繊維コード用接着剤組成物のみを用いて接着されてなり、前記ゴムラテックス(C)が、(i)スチレン含有率30〜60質量%、ブタジエン含有率60質量%未満およびビニルピリジン含有率0.5〜15質量%で構成される単量体混合物を重合させた後、(ii)引き続いてスチレン含有率10〜40質量%、ブタジエン含有率45〜75質量%およびビニルピリジン含有率5〜20質量%で構成される単量体混合物を、前記(i)における重合で用いたスチレン含有率よりも低いスチレン含有率で重合させて得られる、二重構造を有するビニルピリジン−スチレン−ブタジエン系共重合体ラテックスからなることを特徴とするゴム補強材。
- 前記エポキシ化合物(B)の質量bに対する前記(ブロックド)イソシアネート化合物および/またはアミン系硬化剤(A)の質量aの比率であるa/bが、0.1以上30以下である請求項5記載のゴム補強材。
- 前記ゴムラテックス(C)の質量cに対する、前記エポキシ化合物(B)と前記(ブロックド)イソシアネート化合物および/またはアミン系硬化剤(A)との合計質量b+aの比率である(b+a)/cが、0.1以上1.0以下である請求項5記載のゴム補強材。
- 前記有機繊維コードが、ポリエステルまたはナイロンからなる請求項5記載のゴム補強材。
- 請求項5記載のゴム補強材を用いたことを特徴とするタイヤ。
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PCT/JP2010/057332 WO2010125992A1 (ja) | 2009-04-28 | 2010-04-26 | 有機繊維コード用接着剤組成物、並びにそれを用いたゴム補強材、タイヤおよび接着方法 |
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WO2014091376A1 (en) | 2012-12-13 | 2014-06-19 | Kordsa Global Endustriyel Iplik Ve Kord Bezi Sanayi Ve Ticaret Anonim Sirketi | A dipping material for cord fabrics and a production method thereof |
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CN102414362B (zh) | 2015-01-07 |
CN102414362A (zh) | 2012-04-11 |
WO2010125992A1 (ja) | 2010-11-04 |
KR20120023706A (ko) | 2012-03-13 |
US20120041113A1 (en) | 2012-02-16 |
KR101650607B1 (ko) | 2016-08-23 |
EP2426253A4 (en) | 2015-01-07 |
JPWO2010125992A1 (ja) | 2012-11-01 |
US9394647B2 (en) | 2016-07-19 |
EP2426253A1 (en) | 2012-03-07 |
EP2426253B1 (en) | 2017-08-23 |
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