JP7333349B2 - 再生可能な原材料に基づく包装用接着剤 - Google Patents
再生可能な原材料に基づく包装用接着剤 Download PDFInfo
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- JP7333349B2 JP7333349B2 JP2020572460A JP2020572460A JP7333349B2 JP 7333349 B2 JP7333349 B2 JP 7333349B2 JP 2020572460 A JP2020572460 A JP 2020572460A JP 2020572460 A JP2020572460 A JP 2020572460A JP 7333349 B2 JP7333349 B2 JP 7333349B2
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- B32B2250/02—2 layers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2307/00—Properties of the layers or laminate
- B32B2307/70—Other properties
- B32B2307/748—Releasability
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2439/00—Containers; Receptacles
- B32B2439/70—Food packaging
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2439/00—Containers; Receptacles
- B32B2439/80—Medical packaging
Description
再生可能な原材料を少なくとも一定の割合で含む現在利用可能な接着剤システムは、石油化学原料に基づく従来のシステムと比較して効率が低く、接着剤の値および耐性が低いという欠点がある。
したがって、本発明によって対処される課題は、再生可能な原材料の割合が高く、従来のシステムと比較して同等または改善された効率を有し、特に食品包装の製造に適した接着剤組成物を提供することである。
a) ベツリンに基づく少なくとも1つのポリエステルポリオール;及び
b) 少なくとも1つのNCO末端化合物。
i) 5~50重量%、好ましくは25~35重量%の量のベツリン;及び
ii) 5~45重量%、好ましくは8~40重量%の量のジカルボン酸;及び
iii) 20~80重量%、好ましくは40~70重量%の量のトリグリセリド、
いずれの場合も、モノマー単位の総重量に基づく。
I) R1-NH-SO3Hおよびその塩(R1=CnH2n+1、(n=1~10))、シクロヘキシル、フェニル、アルキル置換シクロヘキシルまたはフェニル;
II) R'4-SO2-NH-C(O)-R4、ここで、R4、R'4=CnH2n+1(n=1~10)、シクロヘキシル、フェニル、アルキル置換シクロヘキシルまたはフェニル;又はR4及びR'4は、脂肪族または芳香族5または6員環の構成要素として共通の、任意にアルキル置換された、C2又はC3ブリッジを形成する種類であり、ここで、R4及びR'4は同一または異なる;
III) R'5-O-SO2-NH-C(O)-R5、ここで、R5、R'5=CnH2n+1、n=1~10、シクロヘキシル、フェニル、アルキル置換シクロヘキシルまたはフェニル;又はR4及びR'4は、脂肪族または芳香族5または6員環の構成要素として共通の、任意にアルキル置換された、C2又はC3ブリッジを形成する種類であり、ここで、R5及びR'5は同一または異なる;
IV)
ここで、R1はI)のように定義される;
V)
ここで、R2、R'2=CnH2n+1、ここで、n=1~10、シクロヘキシル、フェニル、アルキル置換シクロヘキシルまたはフェニル;又はR2及びR'2は、脂肪族または芳香族5または6員環の構成要素として共通の、任意にアルキル置換された、C2又はC3ブリッジを形成する種類であり、ここで、R2及びR'2は同一または異なる;
VI)
ここで、R3、R'3=CnH2n+1、ここで、n=1~10、シクロヘキシル、フェニル、アルキル置換シクロヘキシルまたはフェニル;又はR3及びR'3は、脂肪族または芳香族5または6員環の構成要素として共通の、任意にアルキル置換された、C2又はC3ブリッジを形成する種類であり、ここで、R3及びR'3は同一または異なる。
a) ベツリンと少なくとも1つのトリグリセリドとを含む混合物を提供する工程;
b) 工程a)の混合物から得られた反応生成物をNCO末端化合物と反応させる工程。
表1は、本発明による接着剤組成物に使用されるポリエステルポリオールのモノマー組成を示しており、重量はそれぞれの場合にグラムで示されている。括弧内の情報は、mol%での比率を示す。
本発明の好ましい態様は以下を包含する。
〔1〕以下を含む接着剤組成物:
a) ベツリンに基づく少なくとも1つのポリエステルポリオール;及び
b) 少なくとも1つのNCO末端化合物。
〔2〕ベツリンに基づくポリエステルポリオールは、ベツリンと1つまたはそれ以上のトリグリセリドとを反応させることによって得られたものであることを特徴とする、〔1〕に記載の接着剤組成物。
〔3〕ポリエステルポリオールは、それぞれの場合にモノマー単位の総重量に基づき、以下のモノマー単位
i) 5~50重量%、好ましくは25~35重量%の量のベツリン;
ii) 5~45重量%、好ましくは8~40重量%の量のジカルボン酸;及び
iii) 20~80重量%、好ましくは40~70重量%の量のトリグリセリド、
を含む反応混合物から得られたものであることを特徴とする、〔1〕または〔2〕に記載の接着剤組成物。
〔4〕ジカルボン酸は、コハク酸、アジピン酸、アゼライン酸、セバシン酸、ドデカン酸、テトラデカン二酸、フランジカルボン酸、イソフタル酸、テレフタル酸、オルトフタル酸およびそれらの混合物からなる群から選択されることを特徴とする、〔1〕~〔3〕のいずれかに記載の接着剤組成物。
〔5〕トリグリセリドは、大豆油、亜麻仁油、ひまわり油、サフラワー油、菜種油、物理ナッツ油、軽クルミ油、ブドウ種子油、カノーラ油、トウモロコシ油、カシュー核油、魚油、ヒマシ油、トール油、ココナッツ油、パーム油、パーム核油、オリーブ油およびそれらの混合物およびそれらの誘導体、ならびに合成または生物工学的に調製されたトリグリセリドからなる群から選択されることを特徴とする、〔3〕に記載の接着剤組成物。
〔6〕NCO末端化合物は、1,5-ナフチレンジイソシアネート(NDI)、2,4'-または4,4'-ジフェニルメタンジイソシアネート(MDI)、トルエンジイソシアネート(TDI)の異性体、メチレントリフェニルトリイソシアネート(MIT)、水素化MDI(H12MDI)、テトラメチルキシレンジレンジイソシアネート(TMXDI)、1-イソシアナトメチル-3-イソシアナト-1,5,5-トリメチルシクロヘキサン(IPDI)、キシリレンジイソシアネート(XDI)、ヘキサン-1,6-ジイソシアネート(HDI)、ペンタメチレンジイソシアネート(PDI)、ジシクロヘキシルメタンジイソシアネートおよびそれらの混合物からなる群から選択されることを特徴とする、〔1〕~〔5〕のいずれかに記載の接着剤組成物。
〔7〕ベツリンに基づくポリエステルポリオールの割合は、それぞれの場合に無溶剤接着剤組成物の総重量に基づいて、20~90重量%、好ましくは30~80重量%、特に好ましくは40~60重量%であることを特徴とする、〔1〕~〔6〕のいずれかに記載の接着剤組成物。
〔8〕NCO末端化合物の割合は、それぞれの場合に無溶剤接着剤組成物の総重量に基づき、10~80重量%、好ましくは20~70重量%、特に好ましくは30~60重量%であることを特徴とする、〔1〕~〔7〕のいずれかに記載の接着剤組成物。
〔9〕組成物は1~5、好ましくは1.2~3のNCO:OH比を有することを特徴とする、〔1〕~〔8〕のいずれかに記載の接着剤組成物。
〔10〕組成物中のクリティカルな移動性成分の割合は、それぞれの場合に無溶剤接着剤組成物の総重量に基づき、300ppm未満、好ましくは200ppm未満、特に好ましくは50ppm未満であることを特徴とする、〔1〕~〔9〕のいずれかに記載の接着剤組成物。
〔11〕以下の工程を含む、〔1〕~〔10〕のいずれかに記載の接着剤組成物の製造方法:
a) ベツリンと少なくとも1つのトリグリセリドを含む混合物を提供する工程;
b) 工程a)の混合物から得られた反応生成物をNCO末端化合物と反応させる工程。
〔12〕〔1〕~〔10〕のいずれかに記載の接着剤組成物を硬化させることによって得られる接着剤。
〔13〕〔1〕~〔10〕のいずれかに記載の接着剤組成物または請求項12に記載の接着剤の積層接着剤としての使用。
〔14〕〔1〕~〔10〕のいずれかに記載の接着剤組成物または請求項12に記載の接着剤を含む物品。
〔15〕〔1〕~〔10〕のいずれかに記載の接着剤組成物を少なくとも1つの基材に塗布し、続いて少なくとも2つの基材を一緒に接合することを特徴とする、少なくとも2つの基材を結合する方法。
Claims (13)
- 以下を含む接着剤組成物:
a) ベツリンに基づく少なくとも1つのポリエステルポリオール;及び
b) 少なくとも1つのNCO末端化合物
であって、ベツリンに基づくポリエステルポリオールは、ベツリンと1つまたはそれ以上のトリグリセリドとを反応させることによって得られたものであることを特徴とする、接着剤組成物。 - ポリエステルポリオールは、それぞれの場合にモノマー単位の総重量に基づき、以下のモノマー単位
i) 5~50重量%の量のベツリン;
ii) 5~45重量%の量のジカルボン酸;及び
iii) 20~80重量%の量のトリグリセリド、
を含む反応混合物から得られたものであることを特徴とする、請求項1に記載の接着剤組成物。 - ジカルボン酸は、コハク酸、アジピン酸、アゼライン酸、セバシン酸、ドデカン酸、テトラデカン二酸、フランジカルボン酸、イソフタル酸、テレフタル酸、オルトフタル酸およびそれらの混合物からなる群から選択されることを特徴とする、請求項1または2に記載の接着剤組成物。
- トリグリセリドは、大豆油、亜麻仁油、ひまわり油、サフラワー油、菜種油、物理ナッツ油、軽クルミ油、ブドウ種子油、カノーラ油、トウモロコシ油、カシュー核油、魚油、ヒマシ油、トール油、ココナッツ油、パーム油、パーム核油、オリーブ油およびそれらの混合物およびそれらの誘導体、ならびに合成または生物工学的に調製されたトリグリセリドからなる群から選択されることを特徴とする、請求項2に記載の接着剤組成物。
- NCO末端化合物は、1,5-ナフチレンジイソシアネート(NDI)、2,4'-または4,4'-ジフェニルメタンジイソシアネート(MDI)、トルエンジイソシアネート(TDI)の異性体、メチレントリフェニルトリイソシアネート(MIT)、水素化MDI(H12MDI)、テトラメチルキシレンジレンジイソシアネート(TMXDI)、1-イソシアナトメチル-3-イソシアナト-1,5,5-トリメチルシクロヘキサン(IPDI)、キシリレンジイソシアネート(XDI)、ヘキサン-1,6-ジイソシアネート(HDI)、ペンタメチレンジイソシアネート(PDI)、ジシクロヘキシルメタンジイソシアネートおよびそれらの混合物からなる群から選択されることを特徴とする、請求項1~4のいずれかに記載の接着剤組成物。
- ベツリンに基づくポリエステルポリオールの割合は、それぞれの場合に無溶剤接着剤組成物の総重量に基づいて、20~90重量%であることを特徴とする、請求項1~5のいずれかに記載の接着剤組成物。
- NCO末端化合物の割合は、それぞれの場合に無溶剤接着剤組成物の総重量に基づき、10~80重量%であることを特徴とする、請求項1~6のいずれかに記載の接着剤組成物。
- 組成物は1~5のNCO:OH比を有することを特徴とする、請求項1~7のいずれかに記載の接着剤組成物。
- 以下の工程を含む、請求項1~8のいずれかに記載の接着剤組成物の製造方法:
a) ベツリンと少なくとも1つのトリグリセリドを含む混合物を提供する工程;
b) 工程a)の混合物から得られた反応生成物をNCO末端化合物と反応させる工程。 - 請求項1~8のいずれかに記載の接着剤組成物を硬化させることによって得られる接着剤。
- 請求項1~8のいずれかに記載の接着剤組成物または請求項10に記載の接着剤の積層接着剤としての使用。
- 請求項1~8のいずれかに記載の接着剤組成物または請求項10に記載の接着剤を含む物品。
- 請求項1~8のいずれかに記載の接着剤組成物を少なくとも1つの基材に塗布し、続いて少なくとも2つの基材を一緒に接合することを特徴とする、少なくとも2つの基材を結合する方法。
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EP18179485.0 | 2018-06-25 | ||
EP18179485.0A EP3587530A1 (de) | 2018-06-25 | 2018-06-25 | Verpackungsklebstoffe basierend auf nachwachsenden rohstoffen |
PCT/EP2019/065968 WO2020002042A1 (en) | 2018-06-25 | 2019-06-18 | Packaging adhesives based on renewable raw materials |
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CN115521434B (zh) * | 2022-09-20 | 2023-11-03 | 中国科学院宁波材料技术与工程研究所 | 一种桦木醇基热塑性聚氨酯弹性体及其制备方法 |
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JP2001288222A (ja) | 2000-04-06 | 2001-10-16 | Kyokuto Kobunshi Kk | ベチュリンから得られるポリマー及びその製造法 |
US20080004369A1 (en) | 2004-11-17 | 2008-01-03 | Jukka Seppala | Crosslinkable Biopolymer |
JP2010202861A (ja) | 2009-03-02 | 2010-09-16 | Rohm & Haas Co | 生物ベースのポリオール |
JP2015160911A (ja) | 2014-02-27 | 2015-09-07 | 大日精化工業株式会社 | 接着剤組成物 |
WO2015133496A1 (ja) | 2014-03-04 | 2015-09-11 | 三井化学株式会社 | ラミネート接着剤、ラミネートフィルムの製造方法、ラミネートフィルムおよびレトルトパウチ材料 |
JP2017527648A (ja) | 2014-07-04 | 2017-09-21 | ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェンHenkel AG & Co. KGaA | フィラー含有ポリウレタンラミネート接着剤 |
WO2018005538A2 (en) | 2016-06-28 | 2018-01-04 | Myriant Corporation | Hybrid polyols based on natural oil polyols |
WO2018095962A1 (de) | 2016-11-25 | 2018-05-31 | Henkel Ag & Co. Kgaa | Niedrig-viskose, schnell härtende kaschierklebstoff-zusammensetzung |
-
2018
- 2018-06-25 EP EP18179485.0A patent/EP3587530A1/de active Pending
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2019
- 2019-06-18 WO PCT/EP2019/065968 patent/WO2020002042A1/en active Application Filing
- 2019-06-18 KR KR1020207036625A patent/KR20210023865A/ko not_active Application Discontinuation
- 2019-06-18 CN CN201980042211.2A patent/CN112292434B/zh active Active
- 2019-06-18 JP JP2020572460A patent/JP7333349B2/ja active Active
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001288222A (ja) | 2000-04-06 | 2001-10-16 | Kyokuto Kobunshi Kk | ベチュリンから得られるポリマー及びその製造法 |
US20080004369A1 (en) | 2004-11-17 | 2008-01-03 | Jukka Seppala | Crosslinkable Biopolymer |
JP2010202861A (ja) | 2009-03-02 | 2010-09-16 | Rohm & Haas Co | 生物ベースのポリオール |
JP2015160911A (ja) | 2014-02-27 | 2015-09-07 | 大日精化工業株式会社 | 接着剤組成物 |
WO2015133496A1 (ja) | 2014-03-04 | 2015-09-11 | 三井化学株式会社 | ラミネート接着剤、ラミネートフィルムの製造方法、ラミネートフィルムおよびレトルトパウチ材料 |
JP2017527648A (ja) | 2014-07-04 | 2017-09-21 | ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェンHenkel AG & Co. KGaA | フィラー含有ポリウレタンラミネート接着剤 |
WO2018005538A2 (en) | 2016-06-28 | 2018-01-04 | Myriant Corporation | Hybrid polyols based on natural oil polyols |
WO2018095962A1 (de) | 2016-11-25 | 2018-05-31 | Henkel Ag & Co. Kgaa | Niedrig-viskose, schnell härtende kaschierklebstoff-zusammensetzung |
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CN112292434A (zh) | 2021-01-29 |
CN112292434B (zh) | 2023-05-16 |
EP3587530A1 (de) | 2020-01-01 |
JP2021528546A (ja) | 2021-10-21 |
KR20210023865A (ko) | 2021-03-04 |
WO2020002042A1 (en) | 2020-01-02 |
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