JP7425977B2 - 湿気硬化型ホットメルト接着剤組成物、接着体、及び衣類 - Google Patents
湿気硬化型ホットメルト接着剤組成物、接着体、及び衣類 Download PDFInfo
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- JP7425977B2 JP7425977B2 JP2021515773A JP2021515773A JP7425977B2 JP 7425977 B2 JP7425977 B2 JP 7425977B2 JP 2021515773 A JP2021515773 A JP 2021515773A JP 2021515773 A JP2021515773 A JP 2021515773A JP 7425977 B2 JP7425977 B2 JP 7425977B2
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- urethane prepolymer
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- melt adhesive
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- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2262/00—Composition or structural features of fibres which form a fibrous or filamentary layer or are present as additives
- B32B2262/02—Synthetic macromolecular fibres
- B32B2262/0261—Polyamide fibres
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- 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
- B32B2262/00—Composition or structural features of fibres which form a fibrous or filamentary layer or are present as additives
- B32B2262/02—Synthetic macromolecular fibres
- B32B2262/0292—Polyurethane fibres
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- 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
- B32B2262/00—Composition or structural features of fibres which form a fibrous or filamentary layer or are present as additives
- B32B2262/12—Conjugate fibres, e.g. core/sheath or side-by-side
- B32B2262/128—Woven fabric
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
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- B32B2307/00—Properties of the layers or laminate
- B32B2307/50—Properties of the layers or laminate having particular mechanical properties
- B32B2307/51—Elastic
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- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
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- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/304—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being heat-activatable, i.e. not tacky at temperatures inferior to 30°C
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Description
一実施形態の湿気硬化型ホットメルト接着剤組成物は、ポリオールに由来する構造単位及びポリイソシアネートに由来する構造単位を含む重合鎖を含み、イソシアネート基を2個以上有するウレタンプレポリマーと、ポリオールに由来する構造単位及びポリイソシアネートに由来する構造単位を含む重合鎖を含み、ひまし油モノオールで変性されているイソシアネート基を1個以上有するウレタンプレポリマーの変性体とを含有する。一般に、湿気硬化型ホットメルト接着剤組成物は、化学反応によって高分子量化し、接着性等を発現し得るものである。ウレタンプレポリマーは、湿気と反応することによって高分子量化して硬化する(硬化物を形成する)ことから、湿気硬化型ホットメルト接着剤の主成分として作用し得る。一方で、ウレタンプレポリマーの変性体は、主に伸縮性の向上に作用していることが推測される。
ウレタンプレポリマーは、ポリオール((a)成分)に由来する構造単位及びポリイソシアネート((b)成分)に由来する構造単位を含む重合鎖を含み、2個以上のイソシアネート基を有する。すなわち、ウレタンプレポリマーは、ポリオールと、ポリイソシアネートとの反応物であって、重合鎖の主鎖の末端基又は側鎖基として、2個以上のイソシアネート基を有している。なお、ウレタンプレポリマーは、後述のひまし油モノオールで変性されているイソシアネート基を有していない化合物を意味し、ウレタンプレポリマーは、後述のウレタンプレポリマーの変性体を包含しない概念である。本実施形態の接着剤組成物は、このようなウレタンプレポリマーを含有することによって、湿気硬化後に優れた接着強度を発現することができる。
(a)成分は、水酸基を2個以上有する化合物であれば、特に制限なく用いることができる。(a)成分は、水酸基を2個有する化合物(ジオール)であってよい。ポリオールは、接着強度をより向上させる観点から、ポリエステルポリオールを含んでいてもよい。(a)成分は、ポリエーテルポリオールをさらに含んでいてもよい。このようなウレタンプレポリマーは、ポリエステルポリオールに由来する構造単位と、ポリエーテルポリオールに由来する構造単位と、ポリイソシアネートに由来する構造単位とを含む重合鎖を含み得る。
溶離液:テトラヒドロフラン
流量:1.0mL/分
カラム温度:40℃
検出器:RI
(b)成分は、イソシアネート基を2個以上有する化合物であれば、特に制限なく用いることができる。(b)成分は、イソシアネート基を2個有する化合物(ジイソシアネート)であってよい。(b)成分としては、例えば、ジフェニルメタンジイソシアネート、ジメチルジフェニルメタンジイソシアネート、トリレンジイソシアネート、キシリレンジイソシアネート、p-フェニレンジイソシアネート等の芳香族イソシアネート;ジシクロヘキシルメタンジイソシアネート、イソフォロンジイソシアネート等の脂環族イソシアネート;ヘキサメチレンジイソシアネート等の脂肪族イソシアネートなどが挙げられる。(b)成分は、反応性及び接着性の観点から、好ましくは芳香族ジイソシアネートを含み、より好ましくはジフェニルメタンジイソシアネートを含む。(b)成分は、1種を単独で用いてもよく、2種以上を組み合わせて用いてもよい。
ウレタンプレポリマーの変性体は、ポリオールに由来する構造単位及びポリイソシアネートに由来する構造単位を含む重合鎖を含み、ひまし油モノオールで変性されているイソシアネート基を1個以上有する。すなわち、ウレタンプレポリマーの変性体は、ウレタンプレポリマーとひまし油モノオールとの反応物であって、重合鎖の主鎖の末端基又は側鎖基として、1個以上のひまし油モノオールで変性されているイソシアネート基を有している。本実施形態の接着剤組成物は、このようなウレタンプレポリマーの変性体を含有することによって、湿気硬化後に優れた伸縮性が発現し得る。例えば、ウレタンプレポリマーがジオールとジイソシアネートとの反応物である場合、重合鎖の主鎖の末端基として存在するイソシアネート基の数は2個である。このウレタンプレポリマーがひまし油モノオールで変性されると、少なくとも一方のイソシアネート基が変性されていることになるため、ウレタンプレポリマーの変性体は、湿気との反応点が少なくなり、ウレタンプレポリマーに比べて、高分子量化が抑制されることが推測される。
(c)成分は、ひまし油を加水分解して得られるひまし油脂肪酸(リシノール酸)に由来する基と1個の水酸基とを有するモノオールである。(c)成分は、例えば、リシノール酸のジグリセリドであってよい。(c)成分は、1種を単独で用いてもよく、2種以上を組み合わせて用いてもよい。
一実施形態の接着体は、第1の被着体と、第2の被着体と、第1の被着体及び第2の被着体を互いに接着する接着剤層とを備え、接着剤層が、上述の湿気硬化型ホットメルト接着剤組成物の硬化物を含有する。接着体を備える物品としては、例えば、衣類(特に、無縫製衣類)が挙げられる。
一実施形態の衣類は、上述の接着体を備える。この場合、第1の被着体及び第2の被着体は布である。衣類は、無縫製衣類であってよい。
<湿気硬化型ホットメルト接着剤組成物の調製>
表1に示す種類及び質量部のポリオール、ポリイソシアネート、及びひまし油モノオールを用いた。予め真空乾燥機によって脱水処理したポリオールに対して、ポリイソシアネートを、ポリオールの水酸基に対するポリイソシアネートのイソシアネート基の当量比が((NCO)当量/(OH)当量)が表1で示す数値となるように加えて、均一になるまで混合した。これを110℃で1時間反応させることによって、ウレタンプレポリマーを得た。表1に示すとおり、(NCO)当量/(OH)当量が1より大きいことから、得られたウレタンプレポリマーは、ポリオールに由来する構造単位及びポリイソシアネートに由来する構造単位を含む重合鎖とその重合鎖に結合した2個以上のイソシアネート基とを有することが推測される。次いで、得られたウレタンプレポリマーに対して、表1で示す質量部のひまし油モノオールを加えて、さらに110℃で1時間減圧脱泡撹拌することによって、湿気硬化型ホットメルト接着剤組成物を得た。湿気硬化型ホットメルト接着剤組成物は、ひまし油モノオールの添加量から見て、イソシアネート基を2個以上有するウレタンプレポリマーとひまし油モノオールで変性されているイソシアネート基を1個以上有するウレタンプレポリマーの変性体とを含む混合物であることが推測される。
・ポリオール(a)
(a-1-1)非晶性ポリエステルポリオール:アジピン酸及びイソフタル酸と、エチレングリコール及びネオペンチルグリコールとを主成分とする非晶性ポリエステルポリオール、水酸基数:2、数平均分子量:2000
(a-2-1)結晶性ポリエステルポリオール:アジピン酸とエチレングリコール及び1,4-ブタンジオールとを主成分とする結晶性ポリエステルポリオール、水酸基数:2、数平均分子量:2000
(a-2-2)結晶性ポリエステルポリオール:アジピン酸と1,6ヘキサンジオールとを主成分とする結晶性ポリエステルポリオール、水酸基数:2、数平均分子量:5000
(a-3-1)ポリエーテルポリオール:旭硝子株式会社製、商品名:EXCENOL2020、数平均分子量:2000、水酸基数:2
・ポリイソシアネート(b)
(b-1)ジフェニルメタンジイソシアネート:日本ポリウレタン工業株式会社製、商品名:ミリオネートMT、イソシアネート基数:2
・ひまし油モノオール(c)
(c-1)ひまし油モノオール:伊藤製油株式会社製、商品名:URIC H-31、水酸基数:1
実施例1~4及び比較例1の硬化前の湿気硬化型ホットメルト接着剤組成物の粘度を、BH-HH型少量回転粘度計(東機産業株式会社製)を用い、ロータ4号、試料量15g、120℃の条件で測定した。結果を表1に示す。
実施例1~4及び比較例1の湿気硬化型ホットメルト接着剤組成物を120℃で溶融し、ディスペンサーによって伸縮性布地(ウレタンをナイロンで囲むようにして形成された糸を用いて編み込まれた布地、厚み:520μm)上に塗布した。その後、塗布した接着剤組成物上に、同じ伸縮性布地を配置し、60℃で接着剤組成物からなる層の厚みを100μmまで圧着することによって積層体を得た。上述の積層体を23℃、50%RHで24時間放置し、接着剤組成物からなる層を硬化させることによって接着体を作製した。接着体の接着強度を、引張試験機(株式会社島津製作所製、商品名:オートグラフAGS-X)を用いて、測定温度25℃、引張速度100mm/分の条件でT型剥離強度試験によって測定し、湿気硬化型ホットメルト接着剤組成物の硬化後の接着強度を求めた。結果を表1に示す。
セパレータフィルムを2枚用意した。実施例1~4及び比較例1の湿気硬化型ホットメルト接着剤組成物を120℃で溶融させてから、1枚のセパレータフィルム上に塗布し、もう1枚のセパレータフィルムで湿気硬化型ホットメルト接着剤組成物を挟み込み、低圧プレス試験機(有限会社稲岡鋳造所製)を用いて、プレス温度100℃、プレス圧力400kPaの条件で100μmの厚さにプレスすることによって湿気硬化型ホットメルト接着剤組成物からなる接着剤フィルムを得た。得られた接着剤フィルムを23℃、50%RHで24時間放置することによって硬化させ、接着剤フィルムの硬化物を得た。得られた接着剤フィルムの硬化物を、ダンベルカッター(株式会社ダンベル製)を用い、ダンベル1号形に打ち抜き、セパレータフィルムを剥離して、測定試料とした。引張弾性率及び伸び率は、オートグラフAGS-X(株式会社島津製作所製)を用いて、測定温度が23℃、引張速度が10mm/分、チャック間距離が40mmの条件で測定した。引張弾性率は、引張初期段階の応力-歪み曲線の傾きから求めた。伸び率は、以下の方法によって求めた。測定試料を引張速度100mm/分で破断まで伸長させた。測定前のサンプル長さ及び破断まで伸長させたときの長さを測定し、それぞれL1及びL2とした。測定したL1及びL2を以下の式に代入することによって算出した。それぞれの結果を表1に示す。
伸び率(%)=L2/L1×100
Claims (5)
- ポリオールに由来する構造単位及びポリイソシアネートに由来する構造単位を含む重合鎖を含み、イソシアネート基を2個以上有するウレタンプレポリマーと、
ポリオールに由来する構造単位及びポリイソシアネートに由来する構造単位を含む重合鎖を含み、ひまし油モノオールで変性されているイソシアネート基を1個以上有するウレタンプレポリマーの変性体と、
を含有する、湿気硬化型ホットメルト接着剤組成物(ただし、分子中に1個以上のオキサゾリジン環を有する化合物をさらに含有する場合を除く。)。 - 前記ウレタンプレポリマーにおけるポリオール及び前記ウレタンプレポリマーの変性体におけるポリオールが、非晶性ポリエステルポリオール及び結晶性ポリエステルポリオールを含む、請求項1に記載の湿気硬化型ホットメルト接着剤組成物。
- 布及び紙から選択される複数の被着体を互いに貼り合わせるために用いられる、請求項1又は2に記載の湿気硬化型ホットメルト接着剤組成物。
- 第1の被着体と、
第2の被着体と、
前記第1の被着体及び前記第2の被着体を互いに接着する接着剤層と、
を備え、
前記接着剤層が、請求項1又は2に記載の湿気硬化型ホットメルト接着剤組成物の硬化物を含有する、接着体。 - 請求項4に記載の接着体を備え、
前記第1の被着体及び前記第2の被着体が布である、衣類。
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KR102363116B1 (ko) * | 2016-04-26 | 2022-02-15 | 쇼와덴코머티리얼즈가부시끼가이샤 | 습기 경화형 반응성 핫멜트 접착제 조성물 및 그의 제조 방법 |
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2019
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- 2019-11-21 JP JP2021515773A patent/JP7425977B2/ja active Active
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- 2019-11-21 US US17/605,661 patent/US20220204826A1/en active Pending
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Patent Citations (4)
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JP2013216723A (ja) | 2012-04-04 | 2013-10-24 | Yokohama Rubber Co Ltd:The | 1液湿気硬化性樹脂組成物、それを用いたシーリング材及び接着剤 |
JP2016074996A (ja) | 2014-10-06 | 2016-05-12 | グンゼ株式会社 | 衣類 |
JP2016121351A (ja) | 2014-12-24 | 2016-07-07 | 東洋インキScホールディングス株式会社 | 接着剤組成物および積層体 |
JP2016160344A (ja) | 2015-03-02 | 2016-09-05 | 日立化成株式会社 | 湿気硬化型反応性ホットメルト接着剤組成物 |
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EP3949778A4 (en) | 2022-05-04 |
WO2020217574A1 (ja) | 2020-10-29 |
TW202106841A (zh) | 2021-02-16 |
KR20220002370A (ko) | 2022-01-06 |
US20220204826A1 (en) | 2022-06-30 |
EP3949778A1 (en) | 2022-02-09 |
CN113966182B (zh) | 2024-05-10 |
CN113966182A (zh) | 2022-01-21 |
JPWO2020217574A1 (ja) | 2020-10-29 |
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