JP2023505661A - タイヤコード用接着組成物、タイヤコードおよびタイヤ - Google Patents
タイヤコード用接着組成物、タイヤコードおよびタイヤ Download PDFInfo
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- JP2023505661A JP2023505661A JP2022533628A JP2022533628A JP2023505661A JP 2023505661 A JP2023505661 A JP 2023505661A JP 2022533628 A JP2022533628 A JP 2022533628A JP 2022533628 A JP2022533628 A JP 2022533628A JP 2023505661 A JP2023505661 A JP 2023505661A
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
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- 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 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 2
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- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 2
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- 239000004743 Polypropylene Substances 0.000 claims description 2
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- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims description 2
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- 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
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Classifications
-
- 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
-
- 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
- B60C9/00—Reinforcements or ply arrangement of pneumatic tyres
- B60C9/0042—Reinforcements made of synthetic materials
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
- C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
- C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/0838—Manufacture of polymers in the presence of non-reactive compounds
- C08G18/0842—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents
- C08G18/0861—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers
- C08G18/0866—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers the dispersing or dispersed phase being an aqueous medium
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
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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
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- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
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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
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- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3228—Polyamines acyclic
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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
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
- C08G18/348—Hydroxycarboxylic acids
-
- 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
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- 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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
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Abstract
Description
エポキシ樹脂とジオール化合物との反応生成物;
イソシアネート化合物;
ラテックス;
水分散ポリウレタン
アミン化合物;および
溶媒
を含む、タイヤコード用接着組成物が提供される。
STD B(Mp):282,000/10,700/580
STD C(Mp):126,000/4,430/370
STD D(Mp):51,200/1,920/162
繊維基材;および
前記繊維基材上に形成され、上述したタイヤコード用接着組成物から形成された接着層
を含む、タイヤコードが提供される。
(エポキシ樹脂とジオール化合物の反応生成物の製造)
エポキシ樹脂(NAGASE社のEX614B)とジオール化合物とを下記表1~表3に記載された重量比で混合し、常温(20℃)下で2時間の間、攪拌して#1~#14の反応生成物を得た。ただし、下記#C1は、ジオール化合物と反応させていないエポキシ樹脂(NAGASE社のEX614B)である。
(水分散ポリウレタンの製造)
ポリエステルポリオール(重量平均分子量2000g/mol)、ジオール(1,6-ヘキサンジオール)、およびイオノマー(dimethylol butanoic acid)を1:0.2:0.8のモル比で反応器に投入し、75±5℃および常圧の下で、4時間の間混合して混合物を得た。メチレンジフェニルジイソシアネート(MDI)を前記ポリエステルポリオールに対して1:2のモル比で前記混合物に添加し、2時間の間反応させてポリウレタンプレポリマーを製造した。製造されたポリウレタンプレポリマーの反応温度を60℃に下げ、溶媒(acetone)に中和剤(トリエタノールアミン、TEA)を投入して分散させた。中和したポリウレタンプレポリマーに、固形分含有量が60重量%になるように、蒸留水を投入して攪拌した。そして、鎖延長剤(ethylene diamine)を、前記ポリエステルポリオールに対して1:1のモル比で添加し攪拌して水分散ポリウレタンを得た(重量平均分子量:308,000g/mol)。
(タイヤコード用接着組成物の製造)
下記表4、5および6に記載された含有量(重量%)で各成分を混合し、常温(20℃)下で24時間の間攪拌して実施例1~14および比較例1の接着組成物をそれぞれ製造した。
-I:イソシアネート化合物(EMS社のIL-6,caprolactam-blocked 4,4’-MDI)
-L:ラテックス(Closlen社の0653、ビニルピリジン-スチレン-ブタジエン系共重合体)
-U:前記製造例Bによる水分散ポリウレタン
-A:アミン化合物(DAEJUNG社のPiperazine)
-S:溶媒(脱塩水)
(タイヤコード用接着組成物の製造)
前記実施例1において、前記製造例Aの#1による1.8重量%の「エポキシ樹脂とジオール化合物の反応生成物」(E成分)の代わりに、エポキシ樹脂(NAGASE社のEX614B)1.2重量%および1,4-ブタンジオール0.6重量%を、前記I、L、U、AおよびS成分と共に添加し攪拌したことを除いては、前記実施例1と同一の方法で接着組成物を製造した。
(タイヤコード用接着組成物の製造)
前記実施例1において、前記製造例Aの#1による1.8重量%の「エポキシ樹脂とジオール化合物との反応生成物」(E成分)の代わりに、1,6-ヘキサンジオール-ジグリシジルエーテル1.8重量%を、前記I、L、U、AおよびS成分と共に添加し攪拌したことを除いては、前記実施例1と同様の方法で接着組成物を製造した。
ポリエステル原糸を使用して360TPMの撚り数を有する下撚糸(Z-方向)2本を準備した。2本の下撚糸を、360TPMの撚り数で共に上撚り(S-方向)して(S-方向に撚り合わせて)合撚糸(1650dtex/2合計)を製造した。前記合撚糸をローコード(raw cord)として使用した。
(1)ウベローデ(Ubbelohde)粘度計を用いて25℃の恒温水槽で、通常の方法により、前記実施例および比較例の接着組成物に対する相対粘度を測定した。相対粘度を測定する前に、脱塩水をウベローデ粘度計に一定量入れた後、脱塩水の粘度を測定する。測定された脱塩水の粘度を基準として、各実施例および比較例の接着組成物に対する相対粘度(R.V.)を測定する。
Claims (15)
- エポキシ樹脂とジオール化合物の反応生成物;
イソシアネート化合物;
ラテックス;
水分散ポリウレタン
アミン化合物;および
溶媒
を含む、タイヤコード用接着組成物。 - 0.5~10.0重量%の前記反応生成物;
1.0~20.0重量%の前記イソシアネート化合物;
1.0~30.0重量%の前記ラテックス;
0.5~10.0重量%の前記水分散ポリウレタン;
0.1~10.0重量%の前記アミン化合物;および
60.0~85.0重量%の前記溶媒
を含む、請求項1に記載のタイヤコード用接着組成物。 - 前記反応生成物は、前記エポキシ樹脂と前記ジオール化合物とが1:0.1~1:5の重量比で反応したものである、請求項1に記載のタイヤコード用接着組成物。
- 前記エポキシ樹脂は、ビスフェノール系エポキシ樹脂、ノボラック系エポキシ樹脂、およびオキサゾリドン系エポキシ樹脂からなる群より選ばれた1種以上を含む、請求項1に記載のタイヤコード用接着組成物。
- 前記ジオール化合物は、炭素数3~8の直鎖または分枝鎖の脂肪族ジオール化合物である、請求項1に記載のタイヤコード用接着組成物。
- 前記ジオール化合物は、1,3-プロパンジオール、1,4-ブタンジオール、1,3-ブタンジオール、2,3-ブタンジオール、および1,6-ヘキサンジオールからなる群より選ばれた1種以上を含む、請求項1に記載のタイヤコード用接着組成物。
- 前記イソシアネート化合物は、メチレンジフェニルジイソシアネート、トルエンジイソシアネート、およびヘキサメチレンジイソシアネートからなる群より選ばれた1種以上を含む、請求項1に記載のタイヤコード用接着組成物。
- 前記ラテックスは、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とその変性ラテックス、スチレン-ブタジエンラテックスとその変性ラテックス、天然ゴムラテックス、アクリル酸エステル共重合体ラテックス、ブチルゴムラテックス、およびクロロプレンゴムラテックスからなる群より選ばれた1種以上を含む、請求項1に記載のタイヤコード用接着組成物。
- 前記水分散ポリウレタンは、ポリカーボネート系ウレタン、ポリエステル系ウレタン、ポリアクリル系ウレタン、ポリテトラメチレン系ウレタン、ポリカプロラクトン系ウレタン、ポリプロピレン系ウレタン、およびポリエチレン系ウレタンからなる群より選ばれた1種以上を含む、請求項1に記載のタイヤコード用接着組成物。
- 前記アミン化合物は、脂肪族アミンおよび脂環族アミンからなる群より選ばれた1種以上を含む、請求項1に記載のタイヤコード用接着組成物。
- 前記溶媒は水である、請求項1に記載のタイヤコード用接着組成物。
- ウベローデ(Ubbelohde)粘度計を用いて25℃の下で測定された、2.0~3.0の相対粘度を有する、請求項1に記載のタイヤコード用接着組成物。
- 繊維基材;および
前記繊維基材上に形成され、請求項1に記載のタイヤコード用接着組成物から形成された接着層
を含む、タイヤコード。 - 前記繊維基材はポリエステル繊維を含むローコード(raw cord)である、請求項13に記載のタイヤコード。
- 請求項13に記載のタイヤコードを含む、タイヤ。
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KR1020210045707A KR102485252B1 (ko) | 2020-04-09 | 2021-04-08 | 타이어 코드용 접착 조성물, 타이어 코드 및 타이어 |
PCT/KR2021/004456 WO2021206491A1 (ko) | 2020-04-09 | 2021-04-09 | 타이어 코드용 접착 조성물, 타이어 코드 및 타이어 |
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EP4074801A1 (en) | 2022-10-19 |
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