JP5462269B2 - イソシアネート及びアルコール間の反応のための新規な触媒 - Google Patents
イソシアネート及びアルコール間の反応のための新規な触媒 Download PDFInfo
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- JP5462269B2 JP5462269B2 JP2011531387A JP2011531387A JP5462269B2 JP 5462269 B2 JP5462269 B2 JP 5462269B2 JP 2011531387 A JP2011531387 A JP 2011531387A JP 2011531387 A JP2011531387 A JP 2011531387A JP 5462269 B2 JP5462269 B2 JP 5462269B2
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- diisocyanate
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- 239000003054 catalyst Substances 0.000 title claims description 33
- 239000012948 isocyanate Substances 0.000 title claims description 15
- 150000002513 isocyanates Chemical class 0.000 title claims description 11
- 238000006243 chemical reaction Methods 0.000 title description 19
- 150000001298 alcohols Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 239000004814 polyurethane Substances 0.000 claims description 14
- 229920002635 polyurethane Polymers 0.000 claims description 14
- 125000005442 diisocyanate group Chemical group 0.000 claims description 13
- -1 silyl organic compound Chemical class 0.000 claims description 13
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 12
- 229920005862 polyol Polymers 0.000 claims description 12
- 150000003077 polyols Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 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 7
- 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 claims description 6
- 150000003973 alkyl amines Chemical class 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 229920005906 polyester polyol Polymers 0.000 claims description 6
- 150000002009 diols Chemical class 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 5
- 229940126062 Compound A Drugs 0.000 claims description 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 239000004604 Blowing Agent Substances 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000005056 polyisocyanate Substances 0.000 claims description 3
- 229920001228 polyisocyanate Polymers 0.000 claims description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
- 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 claims description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 12
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 230000009965 odorless effect Effects 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 6
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 6
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 4
- QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide 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
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
- 239000012975 dibutyltin dilaurate Substances 0.000 description 4
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
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- 238000003786 synthesis reaction Methods 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- CUVMCSMTTFXFLG-UHFFFAOYSA-N 1,2-dicyclohexyl-3-pyrrolidin-1-ylguanidine Chemical compound C1CCCN1NC(NC1CCCCC1)=NC1CCCCC1 CUVMCSMTTFXFLG-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 229940035437 1,3-propanediol Drugs 0.000 description 2
- CWGQLZZRQHTBLU-UHFFFAOYSA-N 1-butyl-1-methyl-2,3-di(propan-2-yl)guanidine Chemical compound CCCCN(C)C(NC(C)C)=NC(C)C CWGQLZZRQHTBLU-UHFFFAOYSA-N 0.000 description 2
- LMNVQOAKGDJQPF-UHFFFAOYSA-N 1-butyl-2,3-dicyclohexyl-1-methylguanidine Chemical compound C1CCCCC1N=C(N(C)CCCC)NC1CCCCC1 LMNVQOAKGDJQPF-UHFFFAOYSA-N 0.000 description 2
- SBHMERWJFZEJCW-UHFFFAOYSA-N 2-(1,2-dicyclohexylpiperidin-3-yl)guanidine Chemical compound C1(CCCCC1)N1C(C(CCC1)NC(=N)N)C1CCCCC1 SBHMERWJFZEJCW-UHFFFAOYSA-N 0.000 description 2
- KUGOAVWLRXOHOR-UHFFFAOYSA-N 2-butyl-1,3-di(propan-2-yl)guanidine Chemical compound CCCCNC(NC(C)C)=NC(C)C KUGOAVWLRXOHOR-UHFFFAOYSA-N 0.000 description 2
- SWQDFHFHNGNOFY-UHFFFAOYSA-N 2-butyl-1,3-dicyclohexylguanidine Chemical compound C1CCCCC1N=C(NCCCC)NC1CCCCC1 SWQDFHFHNGNOFY-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
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- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
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- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
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- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
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Description
イソシアネートを1級又は2級アルコールと50〜100℃で非触媒反応することにより、ポリウレタンの合成が一般的に行われる。例えばルイス酸及びルイス塩基や、同様に多くの金属塩等の多くの触媒が、反応を最適化させるために提案されてきた。これら触媒の例は、下記文献に記載されている。
以上より、本発明の重要な目的は、少なくともジブチルスズジラウレートと同様の活性を有するがスズベースではない、イソシアネート及びアルコール間の反応用触媒を提供することである。
本発明の別の重要な目的は、ポリウレタンの合成に使用することのできる触媒を提供することである。
1)少なくとも1のイソシアネート基を有する化合物Bを、少なくとも1のヒドロキシル基を有する化合物Dと、触媒Cの存在下で反応させるステップであって、触媒Cは化合物Dとは異なり、かつ一般式(1)の非シリル有機化合物であるステップ:
R2基は、水素原子、直線又は分岐状の一価の、アルキル基、シクロアルキル基、置換又は非置換であって少なくとも1のヘテロ原子を含んでもよい、環で置換されたアルキル基、芳香族基、アリールアルキル基、フルオロアルキル基又はアルキルアミン又はアルキルグアニジン基であり;
R3基は、直線又は分岐状で一価の、アルキル基、シクロアルキル基、置換又は非置換であって少なくとも1のヘテロ原子を含んでもよい、環で置換されたアルキル基、又はアリールアルキル、フルオロアルキル、アルキルアミン又はアルキルグアニジン基を表し;
R2基が水素原子でない場合、R2及びR3基は結合して、任意で1以上の置換基で置換されても良い、3−、4−、5−、6−又は7−構成員の脂肪族環を形成してもよく;
R1、R2及びR3基はケイ素原子を含まない追加的条件がある。
R1基は、同一又は異なり;
R3基は、互いに独立して、イソプロピル基、シクロヘキシル基及び直線又は分岐状の、一価のC1−C12アルキル基から選ばれ:
R2基は、水素原子、直線又は分岐状一価のアルキル基、シクロアルキル基、置換又は非置換であって少なくとも1のヘテロ原子を含んでもよい環で置換されたアルキル基、アリールアルキル基、フルオロアルキル基又はアルキルアミン又はアルキルグアニジン基を表し;
R2基が水素原子でない場合、R2及びR3基は結合して、任意で1以上の置換基で置換されても良い、3−、4−、5−、6−又は7−構成員の脂肪族環を形成してもよい。
1)水分の不存在下かつ有効量の本発明の上記記載の触媒C存在下で、モノイソシアネート、ジイソシアネート、ポリイソシアネート及びその混合物の群から選ばれるイソシアネートである、少なくとも1の化合物Bと、モノアルコール、ジオール、ポリオール及びその混合物の群から選ばれるアルコールである、少なくとも1の化合物Dを反応させるステップ。
シクロ脂肪族ジイソシアネートの例として、イソホロンジイソシアネート(IPDI)が挙げられる。
ポリエーテルポリオールは、一般的に、エチレンオキシド、プロピレンオキシド又はテトラヒドロフラン等の環状モノマーをアニオン性又はカチオン性重付加することにより得られる。
多くの発泡剤は当分野に公知であり、その量はポリウレタンフォームである最終製品で求められるセルサイズに従い変化させて使用される。もっとも経済的な薬剤は、水であるが、塩素及び/又はフッ素を有するハロゲン化短鎖アルカン単独又はそれを水と混合して、しばしば使用される。発泡剤は、ポリオール重量の50%までの量でしばしば使用される。
本発明の他の利点及び特徴は、本発明を制限すること無しに例示として示された下記実施例を参照することにより明らかになる。
1HNMR/CDCl3(ppm):0.93(3H、t)、1.14(12H、d)、1.37(2H、sex)、1.52(2H、quint)、3.01(2H、t)、3.57(2H、m)。
1HNMR/CDCl3(ppm):0.88(3H、t)、1.06(12H、d)、1.26(2H、sex)、1.46(2H、quint)、2.67(3H、s)、3.05(2H、t)、3.35(2H、m)。
1HNMR/CDCl3(ppm):0.89(3H、t)、1−1.4(10H、m)、1.47(2H、quint)、1.5−2(12H、複数m)、2.67(3H、s)、2.90(1H、m)、2.97(1H、m)、3.06(2H、t)。
2,4−TDI(2,4−ジイソシアナト−1−メチルベンゼン)及びポリプロピレングリコールからなる2000g/mol重量の配合物を、0.5であるOH/NCOモル比で調製した。この配合物へ触媒を添加した。この試験はジャケット付き反応器内で、60℃ヘッドスペース窒素下で行われた。
a)20%のイソシアネート基の転化率が:DBTL(比較用)では数分後に完了し、触媒(A2)及び(A4)ではそれぞれ50分及び55分後に完了する;
b)50%のイソシアネート基の転化率が:DBTL(比較用)では10分後に完了し、触媒(A2)及び(A4)ではそれぞれ180分及び205分後に完了する。
Claims (8)
- 下記ステップを含む、少なくとも1のウレタン基を有する化合物Aの製造方法;
1)少なくとも1のイソシアネート基を有する化合物Bを、少なくとも1のヒドロキシル基を有する化合物Dと、触媒Cの存在下且つ有機酸金属塩非存在下で反応させるステップであって、触媒Cは化合物Dとは異なり、かつ一般式(1)の非シリル有機化合物であるステップ:
R2基は、水素原子、直線又は分岐状の一価の、アルキル基、シクロアルキル基、置換又は非置換であって少なくとも1のヘテロ原子を含んでもよい、環で置換されたアルキル基、芳香族基、アリールアルキル基、フルオロアルキル基又はアルキルアミン又はアルキルグアニジン基であり;
R3基は、直線又は分岐状で一価の、アルキル基、シクロアルキル基、置換又は非置換であって少なくとも1のヘテロ原子を含んでもよい、環で置換されたアルキル基、又はアリールアルキル、フルオロアルキル、アルキルアミン又はアルキルグアニジン基を表し;
R2基が水素原子でない場合、R2及びR3基は結合して、任意で1以上の置換基で置換されても良い、3−、4−、5−、6−又は7−構成員の脂肪族環を形成してもよく;
R1、R2及びR3基はケイ素原子を含まない追加的条件がある。 - 前記触媒Cは一般式(1)の非シリル有機化合物である請求項1記載の方法:
R1基は、同一又は異なり;
R3基は、互いに独立して、イソプロピル基、シクロヘキシル基及び直線又は分岐状の、一価のC1−C12アルキル基から選ばれ:
R2基は、水素原子、直線又は分岐状一価のアルキル基、シクロアルキル基、置換又は非置換であって少なくとも1のヘテロ原子を含んでもよい環で置換されたアルキル基、アリールアルキル基、フルオロアルキル基又はアルキルアミン又はアルキルグアニジン基を表し;
R2基が水素原子でない場合、R2及びR3基は結合して、任意で1以上の置換基で置換されても良い、3−、4−、5−、6−又は7−構成員の脂肪族環を形成してもよい。 - 前記少なくとも1のウレタン基を有する化合物Aはポリウレタンであり、少なくとも1のイソシアネート基を有する化合物Bはジイソシアネートであり、少なくとも1のヒドロキシル基を有する化合物Dはポリオールである、請求項1〜3いずれか1項記載の方法。
- 下記ステップを含む請求項1〜3いずれか1項記載の方法;
1)水分の不存在下かつ触媒的有効量の請求項1記載の触媒C存在下で、モノイソシアネート、ジイソシアネート、ポリイソシアネート及びその混合物の群から選ばれるイソシアネートである、少なくとも1の化合物Bと、モノアルコール、ジオール、ポリオール及びその混合物の群から選ばれるアルコールである、少なくとも1の化合物Dを反応させるステップ。 - 前記化合物Bは下記化合物の群から選ばれるジイソシアネートである請求項1〜5いずれか1項記載の方法;
ジフェニルメタンジイソシアネート(MDI)、特に4,4’−ジフェニルメタンジイソシアネート又は2,4’−ジフェニルメタンジイソシアネート、トルエンジイソシアネート(TDI)、ヘキサメチレンジイソシアネート(HMDI)、1,3−テトラメチルキシリレンジイソシアネート、イソホロンジイソシアネート、ジシクロヘキサメチルメタンジイソシアネート及びイソホロンジイソシアネート(IPDI)。 - 前記化合物Dはポリエステルポリオールである、請求項4記載の方法。
- 前記ステップ1)は発泡剤の存在下で行われる、請求項1〜7いずれか1項記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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FR0805636 | 2008-10-13 | ||
FR08/05636 | 2008-10-13 | ||
PCT/EP2009/007309 WO2010043353A1 (fr) | 2008-10-13 | 2009-10-12 | Nouveaux catalyseurs pour la reaction entre un isocyanate et un alcool |
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Publication Number | Publication Date |
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JP2012511589A JP2012511589A (ja) | 2012-05-24 |
JP5462269B2 true JP5462269B2 (ja) | 2014-04-02 |
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US (1) | US9102780B2 (ja) |
EP (1) | EP2370488B1 (ja) |
JP (1) | JP5462269B2 (ja) |
KR (1) | KR101362010B1 (ja) |
CN (2) | CN103588943A (ja) |
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US10100068B2 (en) * | 2014-04-16 | 2018-10-16 | Sika Technology Ag | Amidine group—or guanidine group—containing silane |
WO2018015344A1 (de) | 2016-07-18 | 2018-01-25 | Sika Technology Ag | Katalysator für härtbare zusammensetzungen enthaltend hexahydrotriazin-struktureinheiten |
CN116635236A (zh) | 2020-12-18 | 2023-08-22 | 设置性能股份有限公司 | 用于3d打印的有机硅基热塑性材料 |
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ES372183A1 (es) * | 1968-10-04 | 1972-01-16 | Du Pont | Un procedimiento para la preparacion de una espuma flexiblede celdilla abierta. |
GB1289310A (ja) * | 1968-10-04 | 1972-09-13 | ||
LU68552A1 (ja) * | 1973-10-03 | 1975-06-16 | ||
LU74540A1 (ja) * | 1976-03-12 | 1977-09-27 | ||
US4192925A (en) * | 1977-03-31 | 1980-03-11 | Bayer Aktiengesellschaft | Polyhydroxyl compounds containing guanidine groups |
DE3003963A1 (de) * | 1980-02-04 | 1981-08-13 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von ggf. schaumfoermigen polyurethanen |
DE3102343A1 (de) * | 1980-02-04 | 1982-02-18 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von gegebenenfalls schaumfoermigen polyurethanen |
DE3018023A1 (de) * | 1980-05-10 | 1981-11-12 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von polyharnstoffen |
GB8906334D0 (en) * | 1988-03-31 | 1989-05-04 | Ici Plc | Internal mould release compositions |
JPH0749576B2 (ja) * | 1989-10-20 | 1995-05-31 | アドコ・プロダクツ・インコーポレーテッド | 水分にて硬化可能な一剤式シーリング材組成物 |
EP0559216A1 (en) * | 1992-03-06 | 1993-09-08 | Tosoh Corporation | Process for producing urethan foam having high-density skin layer |
JPH05306318A (ja) * | 1992-03-06 | 1993-11-19 | Tosoh Corp | 高密度表層を有するポリウレタンフォームの製造法 |
JP3031897B2 (ja) * | 1998-10-14 | 2000-04-10 | 日東電工株式会社 | エポキシ樹脂硬化物およびこれを得るための硬化方法 |
JP5420895B2 (ja) * | 2006-02-16 | 2014-02-19 | 株式会社カネカ | 硬化性組成物 |
FR2929286A1 (fr) * | 2008-03-28 | 2009-10-02 | Bluestar Silicones France Soc | Composes a structure guanidine et leurs utilisations comme catalyseurs de polycondensation d'organopolysiloxanes |
FR2930778A1 (fr) * | 2008-04-30 | 2009-11-06 | Bluestar Silicones France Soc | Article presentant des proprietes antisalissures et destine a etre utilise dans des applications aquatiques en particulier marines |
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KR20110070865A (ko) | 2011-06-24 |
EP2370488B1 (fr) | 2020-03-25 |
US9102780B2 (en) | 2015-08-11 |
US20110263743A1 (en) | 2011-10-27 |
KR101362010B1 (ko) | 2014-02-11 |
JP2012511589A (ja) | 2012-05-24 |
EP2370488A1 (fr) | 2011-10-05 |
CN102209739B (zh) | 2015-12-02 |
CN102209739A (zh) | 2011-10-05 |
WO2010043353A1 (fr) | 2010-04-22 |
CN103588943A (zh) | 2014-02-19 |
MX2011003894A (es) | 2011-11-04 |
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