JPWO2017090588A1 - 無溶剤接着剤用ポリイソシアネート組成物、無溶剤型接着剤及びそれを用いた積層フィルムの製造方法 - Google Patents
無溶剤接着剤用ポリイソシアネート組成物、無溶剤型接着剤及びそれを用いた積層フィルムの製造方法 Download PDFInfo
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- JPWO2017090588A1 JPWO2017090588A1 JP2017515860A JP2017515860A JPWO2017090588A1 JP WO2017090588 A1 JPWO2017090588 A1 JP WO2017090588A1 JP 2017515860 A JP2017515860 A JP 2017515860A JP 2017515860 A JP2017515860 A JP 2017515860A JP WO2017090588 A1 JPWO2017090588 A1 JP WO2017090588A1
- Authority
- JP
- Japan
- Prior art keywords
- polyisocyanate
- maleic anhydride
- adhesive
- mass
- film
- 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.)
- Granted
Links
- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 184
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 184
- 239000000203 mixture Substances 0.000 title claims abstract description 123
- 239000000853 adhesive Substances 0.000 title claims abstract description 85
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 84
- 238000004519 manufacturing process Methods 0.000 title abstract description 10
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- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 44
- 229920001577 copolymer Polymers 0.000 claims abstract description 39
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000010030 laminating Methods 0.000 claims abstract description 13
- 239000002994 raw material Substances 0.000 claims abstract description 12
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- 239000012790 adhesive layer Substances 0.000 claims abstract description 5
- 239000003205 fragrance Substances 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 33
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 27
- 229910052782 aluminium Inorganic materials 0.000 claims description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 239000012948 isocyanate Substances 0.000 claims description 17
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims description 16
- 150000002513 isocyanates Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 12
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- -1 isocyanate compound Chemical class 0.000 description 33
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
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- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 13
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 229920000728 polyester Polymers 0.000 description 8
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 7
- 239000005058 Isophorone diisocyanate Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000004677 Nylon Substances 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- 239000004927 clay Substances 0.000 description 6
- 239000000539 dimer Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- 229920001778 nylon Polymers 0.000 description 6
- 239000004814 polyurethane Substances 0.000 description 6
- 229920002635 polyurethane Polymers 0.000 description 6
- 235000015067 sauces Nutrition 0.000 description 6
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 5
- 239000001361 adipic acid Substances 0.000 description 5
- 235000011037 adipic acid Nutrition 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
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- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
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- 238000007639 printing Methods 0.000 description 4
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 4
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- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 3
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
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Abstract
Description
また、接着強度についても高温でのレトルト処理後の強度、アルミ基材に対する密着性などが充分でない他、接着剤長期保存後の使用で増粘してしまった場合には、もはや接着剤として機能しないものであった。加えて、配合成分であるプロピレンカーボネートは低分子量であるため食品用パウチへ適用した際に、内容物へ溶出することが懸念される問題もあった。
本発明にかかる接着剤は、イソシアネート基と水酸基との化学反応によって硬化する接着剤であり、無溶剤型の接着剤として使用することができる。なお本発明でいう無溶剤型の接着剤の「溶剤」とは、本発明で使用するポリイソシアネート(A)やポリオールを溶解することの可能な、溶解性の高い有機溶剤を指し、「無溶剤」とは、これらの溶解性の高い有機溶剤を含まないことを指す。溶解性の高い有機溶剤とは、具体的には、トルエン、キシレン、塩化メチレン、テトラヒドロフラン、メタノール、エタノール、イソプロピルアルコール、酢酸メチル、酢酸エチル、酢酸n−ブチル、アセトン、メチルエチルケトン(MEK)、シクロヘキサノン、トルオール、キシロール、n−ヘキサン、シクロヘキサン等が挙げられる。中でもトルエン、キシレン、塩化メチレン、テトラヒドロフラン、酢酸メチル、酢酸エチルは特に溶解性の高い有機溶剤として知られている。
また、ポリイソシアネート(A)として、4,4’−ジフェニルメタンジイソシアネート(MDI)を反応性希釈剤として使用する場合には、環境負荷の高い芳香族アミン(PAA)を生成し易いが、芳香族ビニル・無水マレイン酸共重合体(B)は、このPAAの溶出を抑制できる、という効果をも奏する。
トリエチレングリコール等のグリコール;グリセリン、トリメチロールプロパン、ペンタエリスリトール等の3官能又は4官能の脂肪族アルコール;ビスフェノールA、ビスフェノールF、水素添加ビスフェノールA、水素添加ビスフェノールF等のビスフェノール;
ダイマージオール;前記グリコール等の重合開始剤の存在下にエチレンオキサイド、プロピレンオキサイド、ブチレンオキサイド、スチレンオキサイド、エピクロルヒドリン、テトラヒドロフラン、シクロヘキシレン等のアルキレンオキシドを付加重合したポリエーテルポリオール;該ポリエーテルポリオールを更に前記芳香族又は脂肪族ポリイソシアネートで高分子量化したウレタン結合含有ポリエーテルポリオール;プロピオラクトン、ブチロラクトン、ε−カプロラクトン、σ−バレロラクトン、β−メチル−σ−バレロラクトン等の環状エステル化合物の開環重合反応によって得られるポリエステルと前記グリコール、グリセリン、トリメチロールプロパン、ペンタエリスリトール等の多価アルコールとの反応物であるポリエステルポリオール(1);
前記3官能又は4官能の脂肪族アルコールと、多価カルボン酸とを反応させて得られるポリエステルポリオール(3);2官能型ポリオールと、前記3官能又は4官能の脂肪族アルコールと、多価カルボン酸とを反応させて得られるポリエステルポリオール(4);ジメチロールプロピオン酸、ひまし油脂肪酸等のヒドロキシル酸の重合体である、ポリエステルポリオール(5);前記ポリエステルポリオール(1)〜(5)と前記ポリエーテルポリオールと芳香族若しくは脂肪族ポリイソシアネートとを反応させて得られるウレタン結合含有ポリエステルポリエーテルポリオール;前記ポリエステルポリオール(1)〜(5)を芳香族若しくは脂肪族ポリイソシアネートで高分子量化して得られるポリエステルポリウレタンポリオール;ポリエステルポリオール(1)〜(5)とポリエーテルポリオールとの混合物等が挙げられる。
通常接着剤硬化温度は、15〜60度の範囲で行うことが一般的である。
ジエチレングリコール560質量部を反応容器に仕込み、窒素ガス気流下で撹拌しながら80℃に加熱した。更に撹拌しながらアジピン酸600質量部を反応容器に仕込み150℃〜240℃に加熱してエステル化反応を行った。酸価が5mgKOH/g以下になったところで反応容器を徐々に減圧し、1mmHg以下、200〜240℃で1時間反応させ、酸価0.8mgKOH/g、分子量約840の両末端に水酸基を有するポリエステルポリオール樹脂(以下、これを「ポリエステルポリオール樹脂Y1」と略記する)を得た。
ジエチレングリコール 690質量部、トリメチロールプロパン8質量部を反応容器に仕込み、窒素ガス気流下で撹拌しながら80℃に加熱して溶解した。更に撹拌しながらアジピン酸810質量部を反応容器に仕込み150℃〜240℃に加熱してエステル化反応を行った。酸価が5mgKOH/g以下になったところで反応容器を徐々に減圧し、1mmHg以下、200〜220℃で1時間反応させ、酸価0.8mgKOH/g、分子量約1270の両末端に水酸基を有するポリエステルポリオール樹脂(以下、これを「ポリエステルポリオール樹脂Y2」と略記する)を得た。
2−メチル−プロパンジオール333質量部、エチレングリコール179質量部、トリメチロールプロパン39質量部、を反応容器に仕込み、窒素ガス気流下で撹拌しながら80℃に加熱して溶解した。更に撹拌しながらイソフタル酸106質量部、アジピン酸610質量部を反応容器に仕込み150℃〜240℃に加熱してエステル化反応を行った。酸価が5mgKOH/g以下になったところで反応容器を徐々に減圧し、1mmHg以下、200〜240℃で1時間反応させ、酸価0.5mgKOH/g、分子量約2100の両末端に水酸基を有するポリエステルポリオール樹脂(以下、これを「ポリエステルポリオール樹脂Y3」と略記する)を得た。
合成例1で得られたポリエステルポリオール樹脂Y1の1100質量部に対して、4,4’−ジフェニルメタンジイソシアネート250質量部、MDI混合物[BASF社製「ルプラネートMI」、4,4’−ジフェニルメタンジイソシアネート/2,4’−ジフェニルメタンジイソシアネート(質量比)が1/1の混合物、NCO基含量33.3g/100g以上]1000質量部、スチレンと無水マレイン酸とを反応比率[スチレン/無水マレイン酸]が2/1で反応させて得られたスチレン・無水マレイン酸共重合体(クレイ・バレー社「SMA2000」、酸価355mgKOH/g、重量平均分子量(Mw)7500、以下これを「SMA−B1」と略記する。)47質量部を反応容器に仕込み、窒素ガス気流下で撹拌しながら85℃に加熱し約10時間反応させ、滴定法(ジ−n−ブチルアミン使用)によるイソシアネート%が13.0質量%の2官能ポリイソシアネートとSMA−B1との組成物を得た。
このSMA−B1を2質量%含有するポリイソシアネート組成物を「ポリイソシアネート組成物X1」とする。
合成例2で得られたポリエステルポリオール樹脂Y2の1280質量部に対して、4,4’−ジフェニルメタンジイソシアネート250質量部、MDI混合物[BASF社製「ルプラネートMI」、4,4’−ジフェニルメタンジイソシアネート/2,4’−ジフェニルメタンジイソシアネート(質量比)が1/1の混合物、NCO基含量g/100g以上]1000質量部、SMA−B1 51質量部を反応容器に仕込み、窒素ガス気流下で撹拌しながら85℃に加熱し約10時間反応させ、滴定法(ジ−n−ブチルアミン使用)によるイソシアネート%が13.4質量%の2官能ポリイソシアネートとSMA−B1との組成物を得た。
このSMA−B1を2質量%含有するポリイソシアネート組成物を「ポリイソシアネート組成物X2」とする。
実施例1において、SMA−B1の使用量を2.35質量部とした他は、実施例1と同様にして、2官能ポリイソシアネートとSMA−B1との組成物を得た。
このSMA−B1を0.1質量%含有するポリイソシアネート組成物を「ポリイソシアネート組成物X3」とする。
実施例1において、SMA−B1の使用量を117.5質量部とした他は、実施例1と同様にして、2官能ポリイソシアネートとSMA−B1との組成物を得た。
このSMA−B1を5質量%含有するポリイソシアネート組成物を「ポリイソシアネート組成物X4」とする。
実施例1において、SMA−B1の47質量部を、スチレンと無水マレイン酸とを反応比率[スチレン/無水マレイン酸]が3/1で反応させて得られたスチレン・無水マレイン酸共重合体(クレイ・バレー社「SMA3000」、酸価285mgKOH/g、重量平均分子量(Mw)9500、以下これを「SMA−B2」と略記する。)の47質量部へ変更した他は、実施例1と同様にして、2官能ポリイソシアネートとSMA−B2との組成物を得た。
このSMA−B2を2質量%含有するポリイソシアネート組成物を「ポリイソシアネート組成物X5」とする。
実施例1において、SMA−B1の47質量部を、スチレンと無水マレイン酸とを反応比率[スチレン/無水マレイン酸]が4/1で反応させて得られたスチレン・無水マレイン酸共重合体(クレイ・バレー社「SMA EF−40」、酸価215mgKOH/g、重量平均分子量(Mw)10500、以下これを「SMA−B3」と略記する。)の47質量部へ変更した他は、実施例1と同様にして、2官能ポリイソシアネートとSMA−B3との組成物を得た。
このSMA−B3を2質量%含有するポリイソシアネート組成物を「ポリイソシアネート組成物X6」とする。
合成例1で得られたポリエステルポリオール樹脂Y1の1520質量部に対して、トルエンジイソシアネート1000質量部、SMA−B1の50質量部を反応容器に仕込み、窒素ガス気流下で撹拌しながら85℃に加熱し約8時間反応させ、イソシアネート%が13.6質量%末端トルエンジイソシアネートからなる2官能ポリイソシアネートを得た。このスチレン/無水マレイン酸=2/1樹脂を2%含有するポリイソシアネート組成物を「ポリイソシアネートX7」とする。
合成例1で得られたポリエステルポリオール樹脂Y1の1370質量部に対して、m−キシレンジイソシアネートの1000質量部、SMA−B1の47質量部を反応容器に仕込み、窒素ガス気流下で撹拌しながら85℃に加熱し約10時間反応させ、イソシアネート%が13.5質量%末端の2官能ポリイソシアネートを得た。このSMA−B1を2質量%含有するポリイソシアネート組成物をポリイソシアネートX8とする。
合成例1で得られたポリエステルポリオール樹脂Y1の1075質量部に対して、イソフォロンジイソシアネート1000質量部、SMA−B1の42質量部を反応容器に仕込み、窒素ガス気流下で撹拌しながら85℃に加熱し約12時間反応させ、イソシアネート%が12.9%末端の2官能ポリイソシアネートを得た。このSMA−B1を2質量%含有するポリイソシアネート組成物をポリイソシアネートX9とする。
合成例1で得られたポリエステルポリオール樹脂Y1の820質量部に対して、ジシクロヘキシルメタン4,4’−ジイソシアネート(エボニック社製「Vestanat H12MDI」)1000質量部、SMA−B1の36質量部を反応容器に仕込み、窒素ガス気流下で撹拌しながら85℃に加熱し約10時間反応させ、イソシアネート%が12.8%末端の2官能ポリイソシアネートを得た。このSMA−B1を2質量%配合含有するポリイソシアネート組成物をポリイソシアネート組成物X10とする。
合成例1で得られたポリエステルポリオール樹脂Y1の535質量部、及び重量平均分子量1000のポリプロピレングリコールの535質量部に対して、4,4’−ジフェニルメタンジイソシアネート650質量部、カルボジイミド修飾4,4−メチレンビスフェニルジイソシアネート(BASF社製「ルプラネートMM−103」)650質量部、SMA−B1の47質量部を反応容器に仕込み、窒素ガス気流下で撹拌しながら85℃に加熱し約10時間反応させ、滴定法(ジ−n−ブチルアミン使用)によるイソシアネート%が13.3質量%の2官能ポリイソシアネートを得た。このSMA−B1を2質量%含有するポリイソシアネート組成物をポリイソシアネート組成物X11とする。
合成例1で得られたポリエステルポリオール樹脂Y1の1800質量部に対して、m−キシレンジイソシアネート700質量部、ヘキサメチレンジイソシアネートアロファネート体(BASF社製「Basonat HA300」)1000質量部、SMA−B1の70質量部を反応容器に仕込み、窒素ガス気流下で撹拌しながら85℃に加熱し約10時間反応させ、滴定法(ジ−n−ブチルアミン使用)によるイソシアネート%が8.1%末端の2官能ポリイソシアネートを得た。このSMA−B1を2質量%配合含有するポリイソシアネート組成物をポリイソシアネート組成物X12とする。
合成例1で得られたポリエステルポリオール樹脂Y1の1800質量部に対して、m−キシレンジイソシアネート700質量部、イソホロンジイソシアネート1000質量部、SMA−B1の70質量部を反応容器に仕込み、窒素ガス気流下で撹拌しながら85℃に加熱し約10時間反応させ、滴定法(ジ−n−ブチルアミン使用)によるイソシアネート%が9.0%末端の2官能ポリイソシアネートを得た。その後、イソホロンジイソシアネートのイソシアヌレート170部を100℃にて溶解した。このSMA−B1を2質量%配合含有するポリイソシアネート組成物をポリイソシアネート組成物X13とする。
ヘキサンメチレンジイソシアヌレート(住友コベストロジャパン製 ディスモデュールN3300)の1190質量部に対して、イソフォロンジイソシアネートのイソシアヌレート790部、SMA−B1の20質量部を容器に仕込み、窒素ガス気流下で撹拌しながら85℃にて加熱溶解した。このSMA−B1を2質量%含有する3官能ポリイソシヌレート構成されるポリイソシアネート組成物をポリイソシアネート組成物X13とする。
合成例3で得られたポリエステルポリオール樹脂Y3の1000質量部に対し、スチレンと無水マレイン酸とを反応比率[スチレン/無水マレイン酸]が1/1で反応させて得られたスチレン・無水マレイン酸共重合体(クレイ・バレー社「SMA 1000」、酸価480mgKOH/g、重量平均分子量(Mw)5500、以下これを「SMA−B4」と略記する。)を20質量部添加し、2時間攪拌してSMA−B4を溶解した。このSMA−B4を2質量%含有する樹脂をポリエステルポリオール組成物Y’とする。
合成例1で得られたポリエステルポリオール樹脂Y1の1100質量部に対して、4,4−メチレンビスジフェニルイソシアネート250質量部、MDI混合物[BASF社製「ルプラネートMI」、4,4’−ジフェニルメタンジイソシアネート/2,4’−ジフェニルメタンジイソシアネート(質量比)が1/1の混合物、NCO基含量g/100g以上]1000質量部を反応容器に仕込み、窒素ガス気流下で撹拌しながら85℃に加熱し約10時間反応させ、滴定法(ジ−n−ブチルアミン使用)によるイソシアネート%が13.2質量%の2官能ポリイソシアネートを得た。このスチレン/無水マレイン酸樹脂を含まない樹脂をポリイソシアネート樹脂Hx1とする。
実施例1において、SMA−B1の47質量部を、SMA−B4の47質量部へ変更した他は、実施例1と同様にして、2官能ポリイソシアネートとSMA−B4との組成物を得た。
このSMA−B4を2質量%含有するポリイソシアネート組成物を「ポリイソシアネート組成物Hx2」とする。
実施例1において、SMA−B1の47質量部を、スチレンと無水マレイン酸とを反応比率[スチレン/無水マレイン酸]が6/1となる割合で反応させて得られたスチレン・無水マレイン酸共重合体(クレイ・バレー社「SMA EF60」、酸価156mgKOH/g、重量平均分子量(Mw)11500、以下これを「SMA−B5」と略記する。)の47質量部へ変更した他は、実施例1と同様にして、2官能ポリイソシアネートとSMA−B3との組成物を得た。
このSMA−B5を2質量%含有するポリイソシアネート組成物を「ポリイソシアネート組成物Hx3」とする。
ヘキサンメチレンジイソシアヌレート(住友コベストロジャパン製 ディスモデュールN3300)の1190質量部に対して、イソフォロンジイソシアネートのイソシアヌレート790部を容器に仕込み、窒素ガス気流下で撹拌しながら85℃にて加熱溶解した。この3官能ポリイソシヌレートで構成されるポリイソシアネート組成物をポリイソシアネート組成物Hx4とする。
表1−1、表1−2、又は表2の配合に従い接着剤を調整し、下記の各種評価を行った。結果を表1−1、表1−2、及び表2に示す。
表1−1、表1−2、表1−3、又は表2の配合に従い、接着剤を配合した後、印刷インキユニビアNT(DIC製)で図柄をグラビア印刷したPETフィルム(15um)に、塗布量が固形分2.0g/m2程度となるように塗布し、ラミネーターでこのフィルムの塗布面とCPPフィルム(75um)と貼合し、ラミネートフィルムを作製した。このラミネートフィルムを40℃の恒温槽に3日間保存した。
ラミネートフィルムから15mm幅で切り取り、引張り試験機を使用して、T型剥離により剥離速度300mm/minで接着強度(N/15mm)を測定した。
ラミネート強度は高いほうが好ましく4N/15mm以上であればよいが、5N/15mm以上であるとなお好ましい。
前記合成例、実施例、比較例のポリイソシアネート組成物、ポリエステルポリオール組成物、ポリイソシアネート樹脂を製造した後、60℃にて10日間静置した。
静置後の組成物あるいは樹脂を使用し、表1又は表2の配合に従い接着剤を配合し、同様にしてラミネート強度を測定した。
接着剤を配合した後、印刷インキ(DIC(株)製「ユニビアNT」)で図柄をグラビア印刷したPETフィルムに、塗布量が固形分2.0g/m2程度となるように塗布し、ラミネーターでこのフィルムの塗布面とLLDPEフィルムと貼合し、ラミネートフィルムを作製した。このラミネートフィルムを40℃の恒温槽に3日間保存した。
このラミネートフィルムを150mm×300mmで切り取り、LLDPが内側になるように折り曲げ、1atm、180℃、1秒間でヒートシールしてパウチを作製した。内容物として1/1/1ソース(ミートソース : 植物油 : 食酢=1 : 1 : 1)を加えた。
充填したパウチはスチーム殺菌処理を121℃−30分にて実施し、内容物を除去しヒートシール部のT型剥離による強度を測定した。
また、取り出し後のそれぞれのパウチの外観を観察し、デラミの発生の有無により、以下の評価を行った。
評価△:デラミ箇所が5点以下
評価×:デラミ箇所が6点以上
接着剤を配合した後、印刷インキ(DIC(株)製「ユニビアNT」)で図柄をグラビア印刷したPETフィルムに、塗布量が固形分2.0g/m2程度となるように塗布し、ラミネーターでこのフィルムの塗布面とアルミ箔(15um)と貼合し、40℃の恒温槽に3日間保存した。その後、ラミネートフィルムのアルミ面にCPP(75um)と貼合し、ラミネートフィルムを作製した。このラミネートフィルムを40℃の恒温槽に3日間保存した。
このラミネートフィルムを150mm×300mmで切り取り、CPPが内側になるように折り曲げ、1atm、180℃、1秒間でヒートシールしてパウチを作製した。内容物として1/1/1ソース(ミートソース : 植物油 : 食酢=1 : 1 : 1)を加えた。
充填したパウチはスチーム殺菌処理を121℃−30分にて実施し、内容物を除去しアルミ/CPP間の強度をT型剥離により測定した。
また、取り出し後のそれぞれのパウチの外観を観察し、デラミの発生の有無により、以下の評価を行った。
接着剤を配合した後、印刷インキ(DIC(株)製「ユニビアNT」)で図柄をグラビア印刷した蒸着PETフィルムの蒸着面に、塗布量が固形分2.0g/m2程度となるように塗布し、ラミネーターでこのフィルムの塗布面とLLDPEと貼合し、ラミネートフィルムを作製した。このラミネートフィルムを40℃の恒温槽に3日間保存した。
このラミネートフィルムを150mm×300mmで切り取り、LLDPEが内側になるように折り曲げ、1atm、180℃、1秒間でヒートシールしてパウチを作製した。内容物として1/1/1ソース(ミートソース : 植物油 : 食酢=1 : 1 : 1)を加えた。
充填したパウチは煮沸処理を98℃−60分にて実施し、内容物を除去し、蒸着PET/LLDPE間のT型剥離による強度を測定した。
また、取り出し後のそれぞれのパウチの外観を観察し、デラミの発生の有無により、以下の評価を行った。
なお使用蒸着フィルムは、アルミ蒸着PETフィルム、シリカ蒸着PETフィルム、アルミナ蒸着PETフィルムである。
前記合成例、実施例、比較例のポリイソシアネート組成物、ポリエステルポリオール組成物、ポリイソシアネート樹脂を製造した後、60℃にて10日間静置した。静置後の組成物あるいは樹脂を使用し表1又は表2の配合に従い接着剤を配合し、同様にしてレトルト後のラミネート強度及び外観を評価した。
表1−1、表1−2、又は表2の配合に従い、接着剤を配合した直後、レオメーターの測定部位に約0.8g程度乗せて、配合直後の粘度が1,000mPa・s程度となる温度で30分間測定した。スタート時と30分後の粘度値から、以下の評価を行った。
評価◎:30分後の粘度がスタート時の配合液の粘度が1以上2倍未満
評価○:30分後の粘度がスタート時の配合液の粘度が2以上3倍未満
評価△:30分後の粘度がスタート時の配合液の粘度が3以上4倍未満
評価×:30分後の粘度がスタート時の配合液の粘度が4倍以上
前記合成例、実施例、比較例のポリイソシアネート組成物、ポリエステルポリオール組成物、ポリイソシアネート樹脂を製造した後、60℃にて10日間静置した。静置後の組成物あるいは樹脂を使用し表1又は表2の配合に従い接着剤を配合し、スタート時と30分後の粘度値から、上記基準に従い評価した。
接着剤を配合した後、PETフィルムに、塗布量が固形分2.0g/m2程度となるように塗布し、ラミネーターでこのフィルムの塗布面とCPPフィルムと貼合し、ラミネートフィルムを作製した。このラミネートフィルムを40℃の恒温槽に3日間保存した。
保存後のラミネートフィルムを120mm×220mmで切り取り、CPPが内側になるように折り曲げ、3方方向を10mm幅で1atm、180℃、1秒間でヒートシールして、内容物が2dm2接触するパウチを作製した。内容物は3%酢酸酢溶液を加えた。充填したパウチを70℃−2時間保存しPAAをLC/MS/MSにて測定した。
PAAは芳香族アミンを表し、
XDAはキシレンジイソシアネートを表し
PET/LLDPEはポリエチレンテレフタレート/直鎖低密度ポリエチレンを表し
AL/CPPはアルミ/無延伸ポリプロピレンを表し
AL蒸着PET/LLDPEはアルミ蒸着ポリエチレンテレフタレート/(直鎖低密度ポリエチレンを表す。
Claims (10)
- ポリイソシアネート(A)、及び芳香族ビニルと無水マレイン酸との共重合体であってその原料モノマーのモル比[芳香族ビニル/無水マレイン酸]が1.5/1〜5/1である芳香族ビニル・無水マレイン酸共重合体(B)を必須成分とすることを特徴とする無溶剤型接着剤用ポリイソシアネート組成物。
- 前記ポリイソシアネート(A)と、芳香族ビニル・無水マレイン酸共重合体(B)との配合割合が、質量比[(A)/(B)]が100/0.1〜100/6となる割合である請求項1に記載の無溶剤型接着剤用ポリイソシアネート組成物。
- 前記ポリイソシアネート(A)が、分子構造内に脂環式構造又は芳香族構造を持つポリイソシアネートとポリオール成分との反応物か、または、脂環式構造、芳香族構造又はヌレート骨格を有するポリイソシアネートである請求項1または2に記載の無溶剤型接着剤用ポリイソシアネート組成物。
- 前記ポリイソシアネート(A)が、滴定法(ジ−n−ブチルアミン使用)によるイソシアネート含有率が8〜20質量%の範囲にある請求項1〜3のいずれかに記載の無溶剤型接着剤用ポリイソシアネート組成物。
- ポリイソシアネートとポリオール成分とを反応させる無溶剤型接着剤用ポリイソシアネート組成物の製造方法であって、
前記反応を、芳香族ビニルと無水マレイン酸との共重合体であってその原料モノマーのモル比[芳香族ビニル/無水マレイン酸]が1.5/1〜5/1である芳香族ビニル・無水マレイン酸共重合体(B)の存在下で行い、
前記ポリイソシアネートと前記芳香族ビニル・無水マレイン酸共重合体(B)との質量比[ポリイソシアネート/芳香族ビニル・無水マレイン酸共重合体(B)]が100/0.1〜100/6であることを特徴とする無溶剤型接着剤用ポリイソシアネート組成物の製造方法。 - 請求項1〜4のいずれか一つに記載の無溶剤型接着剤用ポリイソシアネート組成物と、ポリオール(Y)とを必須成分とすることを特徴とする無溶剤型接着剤。
- 第一の基材フィルムと第二の基材フィルムの間に接着剤層を積層してなる積層フィルムであって、前記接着剤層が、請求項6に記載の無溶剤型接着剤であることを特徴とする積層フィルム。
- 前記基材フィルムが、アルミニウム、シリカ、またはアルミナ層を有する基材フィルムか、または金属フィルムである請求項7に記載の積層フィルム。
- 第一のプラスチックフィルムと第二のプラスチックフィルムの間に接着剤層を積層してなる積層フィルムを袋状に成形してなる包装体であって、前記接着剤層が、請求項6に記載の無溶剤型接着剤であることを特徴とする包装体。
- 前記基材フィルムが、アルミニウム、シリカ、またはアルミナ層を有する基材フィルムか、または金属フィルムである請求項9に記載の包装体。
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JP2001098245A (ja) * | 1999-09-30 | 2001-04-10 | Bridgestone Corp | 接着剤組成物、樹脂材料、ゴム物品、および空気入りタイヤ |
JP2001152127A (ja) * | 2000-11-24 | 2001-06-05 | Lock Paint Kk | ポリウレタン接着剤組成物およびその製造方法 |
TW200305587A (en) * | 2002-03-19 | 2003-11-01 | Rohm & Haas | Urethane polymer compositions |
US9676976B2 (en) * | 2010-06-21 | 2017-06-13 | Dic Corporation | Oxygen-barrier film and adhesive |
WO2014208432A1 (ja) * | 2013-06-24 | 2014-12-31 | Dic株式会社 | ラミネート接着剤組成物 |
US20160152880A1 (en) * | 2013-07-19 | 2016-06-02 | Dic Corporation | Laminate adhesive composition |
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CN103937192B (zh) * | 2014-05-12 | 2015-10-28 | 东莞市信诺橡塑工业有限公司 | Pc/pa11组合物及其制备方法 |
CN106661311B (zh) * | 2014-10-22 | 2019-03-19 | 松下知识产权经营株式会社 | 树脂组合物、预浸料、带树脂的金属箔、覆金属层叠板和印刷布线板 |
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