JP2007177171A - アロファネート基含有ポリイソシアネートの製造方法、ならびにウレタンプレポリマーおよびポリウレタン樹脂組成物 - Google Patents
アロファネート基含有ポリイソシアネートの製造方法、ならびにウレタンプレポリマーおよびポリウレタン樹脂組成物 Download PDFInfo
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- JP2007177171A JP2007177171A JP2005380015A JP2005380015A JP2007177171A JP 2007177171 A JP2007177171 A JP 2007177171A JP 2005380015 A JP2005380015 A JP 2005380015A JP 2005380015 A JP2005380015 A JP 2005380015A JP 2007177171 A JP2007177171 A JP 2007177171A
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- urethane prepolymer
- organic
- resin composition
- polyurethane resin
- Prior art date
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- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 66
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 66
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims abstract description 59
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical group NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 title claims abstract description 59
- 229920005749 polyurethane resin Polymers 0.000 title claims abstract description 35
- 239000011342 resin composition Substances 0.000 title claims abstract description 29
- 238000004519 manufacturing process Methods 0.000 title claims description 28
- -1 hydrogen compound Chemical class 0.000 claims abstract description 67
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000000853 adhesive Substances 0.000 claims abstract description 26
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 26
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
- 125000005461 organic phosphorous group Chemical group 0.000 claims abstract description 7
- 150000005691 triesters Chemical class 0.000 claims abstract description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 3
- 229920005862 polyol Polymers 0.000 claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 4
- 150000001621 bismuth Chemical class 0.000 claims description 3
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 7
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- 230000000052 comparative effect Effects 0.000 description 6
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- 238000004821 distillation Methods 0.000 description 6
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 6
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- 238000000034 method Methods 0.000 description 5
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- 239000004698 Polyethylene Substances 0.000 description 4
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
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- 239000011888 foil Substances 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 229920005906 polyester polyol Polymers 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 4
- PEXOFOFLXOCMDX-UHFFFAOYSA-N tritridecyl phosphite Chemical compound CCCCCCCCCCCCCOP(OCCCCCCCCCCCCC)OCCCCCCCCCCCCC PEXOFOFLXOCMDX-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- GOQYKNQRPGWPLP-UHFFFAOYSA-N heptadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
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- 239000003973 paint Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- 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 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 2
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- AAAWJUMVTPNRDT-UHFFFAOYSA-N 2-methylpentane-1,5-diol Chemical compound OCC(C)CCCO AAAWJUMVTPNRDT-UHFFFAOYSA-N 0.000 description 2
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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- 239000006260 foam Substances 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
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Classifications
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Abstract
【解決手段】ポリウレタン樹脂組成物は、活性水素基を有するウレタンプレポリマーとポリイソシアネート、あるいはイソシアネート基を有するウレタンプレポリマーと活性水素化合物とを含み、上記活性水素基もしくはイソシアネート基を有するウレタンプレポリマーは、側鎖に炭素数が5以上の炭化水素基を有するアロファネート基含有ポリイソシアネートと、2官能以上の活性水素化合物とを反応させてなる。特に、上記アロファネート基含有ポリイソシアネートは、炭素数が5以上のアルコール性水酸基含有化合物と有機ジイソシアネートとを、有機カルボン酸ビスマス塩および有機亜リン酸トリエステルを用いて反応させて得られることが好ましい。
【選択図】なし
Description
本発明に係るウレタンプレポリマーは、側鎖に炭素数が5以上の炭化水素基を有するアロファネート基含有ポリイソシアネートと、2官能以上の活性水素化合物とを反応させてなることを特徴とする。
前記ウレタンプレポリマーは、活性水素基を有する、あるいはイソシアネート基を有することが好ましい。
本発明に係る接着剤、プライマーおよびアンカーコート剤は、上記ポリウレタン樹脂組成物を含有することを特徴とする。
炭素数の多いアロファネート基含有ポリイソシアネートは、炭素数の多いアルコール性水酸基含有化合物と有機ジイソシアネートとを、有機カルボン酸ビスマス塩および有機亜リン酸トリエステルを用いて反応させることにより製造することができる。
本発明に用いられる「炭素数の多いアルコール性水酸基含有化合物」とは、具体的には、炭素数が5以上、好ましくは5〜300である、脂肪族基、脂環族基、芳香族基またはこれらの組み合わせからなる水酸基末端化合物である。
これらのアルコール性水酸基含有化合物のうち、本発明の効果が特に有効に現れる点および取り扱い易さや得られるポリイソシアネートの粘度の観点から、炭素数が5以上のモノオールが好ましい。
上記有機ジイソシアネートとしては、2,4−トリレンジイソシアネート、2,6−トリレンジイソシアネート、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、2,2’−ジフェニルメタンジイソシアネート、4,4’−ジフェニルエーテルジイソシアネート、2−ニトロジフェニル−4,4’−ジイソシアネート、2,2’−ジフェニルプロパン−4,4’−ジイソシアネート、3,3’−ジメチルジフェニルメタン−4,4’−ジイソシアネート、4,4’−ジフェニルプロパンジイソシアネート、m−フェニレンジイソシアネート、p−フェニレンジイソシアネート、ナフチレン−1,4−ジイソシアネート、ナフチレン−1,5−ジイソシアネート、3,3’−ジメトキシジフェニル−4,4’−ジイソシアネート等の芳香族ジイソシアネート;
イソホロンジイソシアネート、水素添加トリレンジイソシアネート、水素添加キシレンジイソシアネート、水素添加ジフェニルメタンジイソシアネート、水素添加テトラメチルキシレンジイソシアネート、ノルボルネンジイソシアネート等の脂環族ジイソシアネートなどが挙げられる。
これらの有機ジイソシアネートのうち、得られるポリイソシアネートの耐候性等の観点から、脂肪族または脂環式のジイソシアネートが好ましく、特にヘキサメチレンジイソシアネートが好ましい。
上記有機カルボン酸ビスマス塩を構成するカルボン酸としては、酢酸、プロピオン酸、酪酸、カプロン酸、オクチル酸、ラウリン酸、ミリスチン酸、パルミチン酸、ステアリン酸、2−エチルヘキサン酸等の飽和脂肪族モノカルボン酸;シクロヘキサンカルボン酸、シクロペンタンカルボン酸等の飽和単環モノカルボン酸;ビシクロ(4.4.0)デカン−2−カルボン酸等の飽和多環モノカルボン酸;ナフテン酸、オレイン酸、リノール酸、リノレン酸、大豆油脂肪酸、トール油脂肪酸等の不飽和脂肪族モノカルボン酸;ジフェニル酢酸等の芳香脂肪族モノカルボン酸;安息香酸、トルイル酸等の芳香族モノカルボン酸などのモノカルボン酸;
これらの有機カルボン酸ビスマス塩のうち、炭素数が10以下のモノカルボン酸のビスマス塩が好ましい。
上記有機亜リン酸トリエステルは下記式(1)で表される化合物である。
(R1O)3P (1)
式(1)中、R1はそれぞれ独立に炭素数1〜20のアルキル基または炭素数1〜20
のアルキル基で置換されていてもよいアリール基を表す。また、前記アルキル基は塩素等のハロゲン元素で置換されていてもよい。
本発明では、まず、上記アルコール性水酸基含有化合物と有機ジイソシアネートとを反応させてウレタン基を有する化合物と形成させる。このときの反応条件は特に限定されず、従来公知の条件で反応させることができる。
め、蒸留が好ましく、特に薄膜蒸留が好ましい。なお、薄膜蒸留の条件は、圧力が0.2kPa以下、温度が100〜200℃であることが好ましく、特に、圧力が0.1kPa以下、温度が120〜180℃であることが好ましい。
の多い炭化水素基を有するため、オレフィンフィルムなどの基材との接着性を向上させることができる。
本発明に係るウレタンプレポリマーは、側鎖に炭素数が5以上の炭化水素基を有するアロファネート基含有ポリイソシアネートと、2官能以上の活性水素化合物とを反応させることによって製造することができる。このようなウレタンプレポリマーのうち、活性水素基またはイソシアネート基を有するウレタンプレポリマーが好ましい。
Rを1.0未満にすると活性水素基含有ウレタンプレポリマーを得ることができ、Rが1.0を超えるとイソシアネート基含有ウレタンプレポリマーを得ることができる。
エート等が挙げられる。
以下、本発明を実施例により説明するが、本発明は、この実施例により何ら限定されるものではない。なお、実施例および比較例における「%」、「部」は特に断りのない限り「重量%」、「重量部」を意味する。
(アロファネート基含有ポリイソシアネートの製造)
攪拌機、温度計、冷却器および窒素ガス導入管を備えた容量1リットルの反応器に、窒素雰囲気下、1,6−ヘキサメチレンジイソシアネート(HDI)930g、デカノール70g、およびトリス(トリデシル)ホスファイト0.5gを仕込み、80℃で2時間ウレタン化反応を行った。次に、反応液にアロファネート化触媒としてオクチル酸ビスマス0.05gを添加し、100℃で反応させた後、塩化ベンゾイル0.03gを添加して反応を停止させた。反応時間は7時間であった。
ネート基の存在が確認されたが、ウレタン基およびイソシアヌレート基は存在しなかった。
使用した原料、アロファネート化の反応条件、および生成物の特性を下記の表1に示す。
(アロファネート基含有ポリイソシアネートの製造)
使用した原料およびアロファネート化の反応条件を表1に記載の原料および反応条件に変更した以外は実施例1と同様にしてポリイソシアネートを製造した。結果を表1に示す。
(アロファネート基含有ポリイソシアネートの製造)
アロファネート化触媒として2−エチルヘキサン酸ジルコニウム0.05g添加し、反応時間を3時間に変更した以外は、実施例1と同様にしてポリイソシアネートを製造した。結果を表1に示す。イソシアヌレート基を有する化合物が4%生成した。
(ポリイソシアネートの製造)
トリス(トリデシル)ホスファイトを使用しなかった以外は、実施例1と同様にしてポリイソシアネートの製造を試みたが、アロファネート化反応が起こらなかった。
1,6−ヘキサメチレンジイソシアネート970gを913gに変更し、デカノールの代わりにトリデカノール87g使用し、アロファネート化触媒として2−エチルヘキサン酸鉛0.05gを使用した添加した以外は、実施例1と同様にしてポリイソシアネートを製造した。結果を表1に示す。反応速度が非常に遅く、アロファネート化に長時間を要した。
(アロファネート基含有ポリイソシアネートの製造)
攪拌機、温度計、冷却器および窒素ガス導入管を備えた容量1リットルの四つ口フラスコに、窒素雰囲気下、表2に示す種類および量の有機ジイソシアネートおよびモノオールと、トリス(トリデシル)ホスファイト0.5gを仕込み、表2に示す反応温度で2時間ウレタン化反応を行った。次に、反応液にアロファネート化触媒としてオクチル酸ビスマス(Bi:19.4%)を0.05g添加し、100℃で反応させてウレタン基のアロファネート基への変換がほぼ完了した時点で、塩化ベンゾイル0.03gを添加して反応を停止させた。反応時間を表2に示す。
攪拌機、温度計、冷却器および窒素ガス導入管を備えた容量1リットルの四つ口フラスコに、ポリオキシプロピレングリコール(三井武田ケミカル(株)製、「Diol−1000」、分子量1000)、ジプロピレングリコールおよび表3に示すポリイソシアネートを表3に示す量で仕込み、窒素気流下、反応温度を60〜70℃の範囲に調整しながら1時間ウレタン化反応を行った。
攪拌機、温度計、冷却器および窒素ガス導入管を備えた容量1リットルの四つ口フラスコに、イソフタル酸530g、エチレングリコール129g、ネオペンチルグリコール302gを仕込み、窒素気流下、反応温度を180〜220℃の範囲に調整しながら6時間エステル化反応を行った。所定量の水を留去した後、セバシン酸215gを添加し、反応温度を180〜220℃の範囲に調整しながら、さらに7時間エステル化反応を行い、水酸基価が45のポリエステルポリオール(P−s1)を得た。
攪拌機、温度計、冷却器および窒素ガス導入管を備えた容量1リットルの四つ口フラスコに、表4に示すポリオールおよびポリイソシアネートを表4に示す量で仕込み、さらにトルエン125gを加えて80℃で1時間ウレタン化反応を行った。
主剤として合成例2で調製した各種ポリエーテルポリウレタンポリオール100部に、硬化剤としてジメチルメタンジイソシアネート/トリレンジイソシアネート混合系ポリイソシアネート硬化剤(タケネートA−5、三井武田ケミカル(株)製)30部を配合して、各種ポリウレタン系接着剤を調製した。
塗布面と未延伸ポリエチレンフィルム(130μm厚、片面コロナ処理)のコロナ処理面とを貼り合わせ、40℃で3日間養生して接着剤を硬化させて、2層複合フィルムを作製した。この複合フィルムについて、下記の方法に従い、接着性試験と耐内容物試験を実施
した。
上記複合フィルムから、長さ150mm×幅15mmの試験片を切り出し、インストロン型引張試験機を用いて、剥離速度300mm/分の条件でT型剥離試験を実施し、接着強度を測定した。結果を表5に示す。
上記複合フィルムの一端をヒートシールして、170mm×65mmのパウチを作製し、このパウチに強アルカリ性洗剤(花王(株)製、「マジックリン」)を充填した。これを50℃で1ヶ月間保存し、保存後のパウチの外観を観察した。また、上記接着性試験と同様にして保存後のパウチの接着強度を測定した。結果を表5に示す。
主剤として表6に示す量の合成例4で調製した各種ポリウレタンポリオールおよび水添ポリブタジエンポリオール(三菱化学(株)製、「ポリテールH」、水酸基価48)と、硬化剤としてHDIトリマー(三井武田ケミカル(株)製、タケネートD−177N)とをNCO/OH当量比で1.2となるように配合し、固形分が25%となるようにトルエンで希釈して各種ポリウレタン系接着剤を調製した。
次に、この接着剤を、常温下、バーコーターを用いてアルミ箔(40μm厚)上に固形分で3.5g/m2となるように塗布し、溶剤を揮発させた後、150℃のオーブン中で
3分間加熱した。その後、アルミ箔をオーブンから取り出し、接着剤塗布面と未延伸ポリエチレンフィルム(130μm厚、片面コロナ処理)のコロナ処理面またはコロナ未処理面とを貼り合わせ、2層複合フィルムを作製し、60℃で5日間養生して接着剤を硬化させた。この複合フィルムについて、実施例7と同様にして接着性試験を実施した。結果を表6に示す。
Claims (13)
- 炭素数が5以上のモノオールと有機ジイソシアネートとを、有機カルボン酸ビスマス塩および有機亜リン酸トリエステルを用いて反応させることを特徴とするアロファネート基含有ポリイソシアネートの製造方法。
- 前記モノオールと前記有機ジイソシアネートとを反応させてウレタン基を有する化合物を形成した後、該化合物を有機カルボン酸ビスマス塩と有機亜リン酸トリエステルとの共存下でアロファネート化することを特徴とする請求項1に記載のアロファネート基含有ポリイソシアネートの製造方法。
- 前記有機ジイソシアネートが、脂肪族または脂環式のジイソシアネートであることを特徴とする請求項1または2に記載のアロファネート基含有ポリイソシアネートの製造方法。
- 側鎖に炭素数が5以上の炭化水素基を有するアロファネート基含有ポリイソシアネートと、2官能以上の活性水素化合物とを反応させてなるウレタンプレポリマー。
- 前記アロファネート基含有ポリイソシアネートが、炭素数が5以上の炭化水素基を有するモノオールと有機ジイソシアネートとを反応させてなることを特徴とする請求項4に記載のウレタンプレポリマー。
- 前記ウレタンプレポリマーが活性水素基を有することを特徴とする請求項4または5に記載のウレタンプレポリマー。
- 前記ウレタンプレポリマーがイソシアネート基を有することを特徴とする請求項4または5に記載のウレタンプレポリマー。
- 請求項6に記載の活性水素基を有するウレタンプレポリマーとポリイソシアネートとを含むポリウレタン樹脂組成物。
- 請求項7に記載のイソシアネート基を有するウレタンプレポリマーと活性水素化合物とを含むポリウレタン樹脂組成物。
- オレフィンポリオールをさらに含有することを特徴とする請求項8または9に記載のポリウレタン樹脂組成物
- 請求項8〜10のいずれかに記載のポリウレタン樹脂組成物を含有する接着剤。
- 請求項8〜10のいずれかに記載のポリウレタン樹脂組成物を含有するプライマー。
- 請求項8〜10のいずれかに記載のポリウレタン樹脂組成物を含有するアンカーコート剤。
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CN2006800497696A CN101351487B (zh) | 2005-12-28 | 2006-12-26 | 含有脲基甲酸酯基的聚异氰酸酯的制备方法、氨基甲酸酯预聚物及聚氨酯树脂组合物 |
MYPI20082396A MY148212A (en) | 2005-12-28 | 2006-12-26 | Process for producing allophanate group-containing polyisocyanates, urethane prepolymers, and polyurethane resin compositions |
PCT/JP2006/325934 WO2007074831A1 (ja) | 2005-12-28 | 2006-12-26 | アロファネート基含有ポリイソシアネートの製造方法、ならびにウレタンプレポリマーおよびポリウレタン樹脂組成物 |
KR1020087018390A KR20080090470A (ko) | 2005-12-28 | 2006-12-26 | 알로파네이트기 함유 폴리아이소사이아네이트의 제조 방법,및 우레탄 프리폴리머 및 폴리우레탄 수지 조성물 |
US12/087,200 US20090036630A1 (en) | 2005-12-28 | 2006-12-26 | Process for Producing Allophanate Group-Containing Polyisocyanates, Urethane Prepolymers, and Polyurethane Resin Compositions |
EP06843318.4A EP1970394B1 (en) | 2005-12-28 | 2006-12-26 | Method for producing allophanate group-containing polyisocyanate |
EP12178828.5A EP2520598A3 (en) | 2005-12-28 | 2006-12-26 | Process for producing allophanate group-containing polyisocyanates, urethane prepolymers, and polyurethane resin compositions |
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Also Published As
Publication number | Publication date |
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US20090036630A1 (en) | 2009-02-05 |
KR20080090470A (ko) | 2008-10-08 |
EP1970394A4 (en) | 2012-05-09 |
EP2520598A2 (en) | 2012-11-07 |
EP2520598A3 (en) | 2013-05-01 |
CN101351487B (zh) | 2011-06-15 |
JP4943004B2 (ja) | 2012-05-30 |
MY148212A (en) | 2013-03-29 |
EP1970394B1 (en) | 2013-05-22 |
WO2007074831A1 (ja) | 2007-07-05 |
EP1970394A1 (en) | 2008-09-17 |
CN101351487A (zh) | 2009-01-21 |
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