JP5452890B2 - スプレーフォーム用途向けの三量化触媒としてのテトラアルキルアンモニウムカルボキシレート塩 - Google Patents
スプレーフォーム用途向けの三量化触媒としてのテトラアルキルアンモニウムカルボキシレート塩 Download PDFInfo
- Publication number
- JP5452890B2 JP5452890B2 JP2008154668A JP2008154668A JP5452890B2 JP 5452890 B2 JP5452890 B2 JP 5452890B2 JP 2008154668 A JP2008154668 A JP 2008154668A JP 2008154668 A JP2008154668 A JP 2008154668A JP 5452890 B2 JP5452890 B2 JP 5452890B2
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- Japan
- Prior art keywords
- fumarate
- maleate
- potassium
- mono
- bis
- 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.)
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- 239000003054 catalyst Substances 0.000 title claims description 81
- -1 Tetraalkylammonium carboxylate salts Chemical class 0.000 title claims description 69
- 239000011493 spray foam Substances 0.000 title claims description 23
- 238000005829 trimerization reaction Methods 0.000 title claims description 19
- 239000000203 mixture Substances 0.000 claims description 78
- 229920005862 polyol Polymers 0.000 claims description 47
- 150000003077 polyols Chemical class 0.000 claims description 45
- 239000004814 polyurethane Substances 0.000 claims description 40
- 229920000582 polyisocyanurate Polymers 0.000 claims description 38
- 239000011495 polyisocyanurate Substances 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 25
- 239000004604 Blowing Agent Substances 0.000 claims description 21
- 229920001228 polyisocyanate Polymers 0.000 claims description 21
- 239000005056 polyisocyanate Substances 0.000 claims description 21
- 239000012948 isocyanate Substances 0.000 claims description 20
- 150000002513 isocyanates Chemical class 0.000 claims description 19
- 239000007921 spray Substances 0.000 claims description 15
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 14
- 238000002156 mixing Methods 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 13
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 12
- HJHUXWBTVVFLQI-UHFFFAOYSA-N tributyl(methyl)azanium Chemical group CCCC[N+](C)(CCCC)CCCC HJHUXWBTVVFLQI-UHFFFAOYSA-N 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 11
- SUOOZFRDMVSBLL-KSBRXOFISA-L (z)-but-2-enedioate;tetramethylazanium Chemical compound C[N+](C)(C)C.C[N+](C)(C)C.[O-]C(=O)\C=C/C([O-])=O SUOOZFRDMVSBLL-KSBRXOFISA-L 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 229920002635 polyurethane Polymers 0.000 claims description 9
- UBUNGTDUKIRAGR-UHFFFAOYSA-M prop-2-enoate;tetramethylazanium Chemical group C[N+](C)(C)C.[O-]C(=O)C=C UBUNGTDUKIRAGR-UHFFFAOYSA-M 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 238000005507 spraying Methods 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 6
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 6
- IUNCEDRRUNZACO-UHFFFAOYSA-N butyl(trimethyl)azanium Chemical group CCCC[N+](C)(C)C IUNCEDRRUNZACO-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims description 6
- 229920005906 polyester polyol Polymers 0.000 claims description 6
- 229920000570 polyether Polymers 0.000 claims description 6
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical group C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 5
- 125000003944 tolyl group Chemical group 0.000 claims description 5
- PAILTSSNLBTUSA-WXXKFALUSA-L (e)-but-2-enedioate;methyl(tripropyl)azanium Chemical compound [O-]C(=O)\C=C\C([O-])=O.CCC[N+](C)(CCC)CCC.CCC[N+](C)(CCC)CCC PAILTSSNLBTUSA-WXXKFALUSA-L 0.000 claims description 4
- XZJHCLBWSRMPDD-BTJKTKAUSA-M (z)-4-hydroxy-4-oxobut-2-enoate;methyl(tripropyl)azanium Chemical compound OC(=O)\C=C/C([O-])=O.CCC[N+](C)(CCC)CCC XZJHCLBWSRMPDD-BTJKTKAUSA-M 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- ZDFSQHNYGUZRGL-UHFFFAOYSA-M butyl(triethyl)azanium prop-2-enoate Chemical compound C(C=C)(=O)[O-].C(C)[N+](CCCC)(CC)CC ZDFSQHNYGUZRGL-UHFFFAOYSA-M 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- DAGGFULQNYPLDJ-JITBQSAISA-L potassium;(e)-but-2-enedioate;methyl(tripropyl)azanium Chemical compound [K+].[O-]C(=O)\C=C\C([O-])=O.CCC[N+](C)(CCC)CCC DAGGFULQNYPLDJ-JITBQSAISA-L 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical group CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 claims description 4
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical group CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 claims description 4
- PAILTSSNLBTUSA-KSBRXOFISA-L (z)-but-2-enedioate;methyl(tripropyl)azanium Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCC[N+](C)(CCC)CCC.CCC[N+](C)(CCC)CCC PAILTSSNLBTUSA-KSBRXOFISA-L 0.000 claims description 3
- VLMDIANDNAXHLV-KSBRXOFISA-L (z)-but-2-enedioate;tributyl(ethyl)azanium Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[N+](CC)(CCCC)CCCC.CCCC[N+](CC)(CCCC)CCCC VLMDIANDNAXHLV-KSBRXOFISA-L 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 3
- ZNAZTTDDAICXNE-WLHGVMLRSA-M ethyl(tripropyl)azanium;(e)-4-hydroxy-4-oxobut-2-enoate Chemical compound OC(=O)\C=C\C([O-])=O.CCC[N+](CC)(CCC)CCC ZNAZTTDDAICXNE-WLHGVMLRSA-M 0.000 claims description 3
- YOMFVLRTMZWACQ-UHFFFAOYSA-N ethyltrimethylammonium Chemical group CC[N+](C)(C)C YOMFVLRTMZWACQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000004088 foaming agent Substances 0.000 claims description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 3
- WOOMMQKFCBDPGE-JITBQSAISA-L potassium;(e)-but-2-enedioate;tetrabutylazanium Chemical compound [K+].[O-]C(=O)\C=C\C([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC WOOMMQKFCBDPGE-JITBQSAISA-L 0.000 claims description 3
- HEOFSSGSXXPIBR-JITBQSAISA-L potassium;(e)-but-2-enedioate;tetraethylazanium Chemical compound [K+].[O-]C(=O)\C=C\C([O-])=O.CC[N+](CC)(CC)CC HEOFSSGSXXPIBR-JITBQSAISA-L 0.000 claims description 3
- WEAIPDDMEQRLCD-JITBQSAISA-L potassium;(e)-but-2-enedioate;tributyl(ethyl)azanium Chemical compound [K+].[O-]C(=O)\C=C\C([O-])=O.CCCC[N+](CC)(CCCC)CCCC WEAIPDDMEQRLCD-JITBQSAISA-L 0.000 claims description 3
- WUHPTBIQBUDTCT-JITBQSAISA-L potassium;(e)-but-2-enedioate;triethyl(methyl)azanium Chemical compound [K+].CC[N+](C)(CC)CC.[O-]C(=O)\C=C\C([O-])=O WUHPTBIQBUDTCT-JITBQSAISA-L 0.000 claims description 3
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims description 3
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims description 3
- SEACXNRNJAXIBM-UHFFFAOYSA-N triethyl(methyl)azanium Chemical group CC[N+](C)(CC)CC SEACXNRNJAXIBM-UHFFFAOYSA-N 0.000 claims description 3
- XZJHCLBWSRMPDD-WLHGVMLRSA-M (e)-4-hydroxy-4-oxobut-2-enoate;methyl(tripropyl)azanium Chemical compound OC(=O)\C=C\C([O-])=O.CCC[N+](C)(CCC)CCC XZJHCLBWSRMPDD-WLHGVMLRSA-M 0.000 claims description 2
- CEDBOZJNBXFAIA-WLHGVMLRSA-M (e)-4-hydroxy-4-oxobut-2-enoate;tetrabutylazanium Chemical compound OC(=O)\C=C\C([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC CEDBOZJNBXFAIA-WLHGVMLRSA-M 0.000 claims description 2
- OLKRIVQBFQVHRL-WLHGVMLRSA-M (e)-4-hydroxy-4-oxobut-2-enoate;tetraethylazanium Chemical compound OC(=O)\C=C\C([O-])=O.CC[N+](CC)(CC)CC OLKRIVQBFQVHRL-WLHGVMLRSA-M 0.000 claims description 2
- JEWIULGLRSNWFL-WLHGVMLRSA-M (e)-4-hydroxy-4-oxobut-2-enoate;tetramethylazanium Chemical compound C[N+](C)(C)C.OC(=O)\C=C\C([O-])=O JEWIULGLRSNWFL-WLHGVMLRSA-M 0.000 claims description 2
- NBJMOMPKBDAQBH-WLHGVMLRSA-M (e)-4-hydroxy-4-oxobut-2-enoate;tetrapropylazanium Chemical compound OC(=O)\C=C\C([O-])=O.CCC[N+](CCC)(CCC)CCC NBJMOMPKBDAQBH-WLHGVMLRSA-M 0.000 claims description 2
- XMALBEDLRZUOAZ-WLHGVMLRSA-M (e)-4-hydroxy-4-oxobut-2-enoate;tributyl(ethyl)azanium Chemical compound OC(=O)\C=C\C([O-])=O.CCCC[N+](CC)(CCCC)CCCC XMALBEDLRZUOAZ-WLHGVMLRSA-M 0.000 claims description 2
- RPISDDBBAAGTKG-WLHGVMLRSA-M (e)-4-hydroxy-4-oxobut-2-enoate;tributyl(methyl)azanium Chemical compound OC(=O)\C=C\C([O-])=O.CCCC[N+](C)(CCCC)CCCC RPISDDBBAAGTKG-WLHGVMLRSA-M 0.000 claims description 2
- GTLCBNAEKSKWOO-WXXKFALUSA-L (e)-but-2-enedioate;ethyl(trimethyl)azanium Chemical compound CC[N+](C)(C)C.CC[N+](C)(C)C.[O-]C(=O)\C=C\C([O-])=O GTLCBNAEKSKWOO-WXXKFALUSA-L 0.000 claims description 2
- ZFIJMOAWKIHRPN-WXXKFALUSA-L (e)-but-2-enedioate;ethyl(tripropyl)azanium Chemical compound [O-]C(=O)\C=C\C([O-])=O.CCC[N+](CC)(CCC)CCC.CCC[N+](CC)(CCC)CCC ZFIJMOAWKIHRPN-WXXKFALUSA-L 0.000 claims description 2
- GQMAJLUQOPVNET-WLHGVMLRSA-M (e)-but-2-enedioate;hydron;triethyl(methyl)azanium Chemical compound [H+].CC[N+](C)(CC)CC.[O-]C(=O)\C=C\C([O-])=O GQMAJLUQOPVNET-WLHGVMLRSA-M 0.000 claims description 2
- IBQYJXBNELPBNT-WXXKFALUSA-L (e)-but-2-enedioate;tetrabutylazanium Chemical compound [O-]C(=O)\C=C\C([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC IBQYJXBNELPBNT-WXXKFALUSA-L 0.000 claims description 2
- JAQVWVXBBKQVNN-WXXKFALUSA-L (e)-but-2-enedioate;tetraethylazanium Chemical compound [O-]C(=O)\C=C\C([O-])=O.CC[N+](CC)(CC)CC.CC[N+](CC)(CC)CC JAQVWVXBBKQVNN-WXXKFALUSA-L 0.000 claims description 2
- SUOOZFRDMVSBLL-WXXKFALUSA-L (e)-but-2-enedioate;tetramethylazanium Chemical compound C[N+](C)(C)C.C[N+](C)(C)C.[O-]C(=O)\C=C\C([O-])=O SUOOZFRDMVSBLL-WXXKFALUSA-L 0.000 claims description 2
- RGHYVCDOGZOTBL-WXXKFALUSA-L (e)-but-2-enedioate;tetrapropylazanium Chemical compound [O-]C(=O)\C=C\C([O-])=O.CCC[N+](CCC)(CCC)CCC.CCC[N+](CCC)(CCC)CCC RGHYVCDOGZOTBL-WXXKFALUSA-L 0.000 claims description 2
- VSOFDBXWYMYSID-WXXKFALUSA-L (e)-but-2-enedioate;tributyl(methyl)azanium Chemical compound [O-]C(=O)\C=C\C([O-])=O.CCCC[N+](C)(CCCC)CCCC.CCCC[N+](C)(CCCC)CCCC VSOFDBXWYMYSID-WXXKFALUSA-L 0.000 claims description 2
- CEDBOZJNBXFAIA-BTJKTKAUSA-M (z)-4-hydroxy-4-oxobut-2-enoate;tetrabutylazanium Chemical compound OC(=O)\C=C/C([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC CEDBOZJNBXFAIA-BTJKTKAUSA-M 0.000 claims description 2
- OLKRIVQBFQVHRL-BTJKTKAUSA-M (z)-4-hydroxy-4-oxobut-2-enoate;tetraethylazanium Chemical compound OC(=O)\C=C/C([O-])=O.CC[N+](CC)(CC)CC OLKRIVQBFQVHRL-BTJKTKAUSA-M 0.000 claims description 2
- NBJMOMPKBDAQBH-BTJKTKAUSA-M (z)-4-hydroxy-4-oxobut-2-enoate;tetrapropylazanium Chemical compound OC(=O)\C=C/C([O-])=O.CCC[N+](CCC)(CCC)CCC NBJMOMPKBDAQBH-BTJKTKAUSA-M 0.000 claims description 2
- XMALBEDLRZUOAZ-BTJKTKAUSA-M (z)-4-hydroxy-4-oxobut-2-enoate;tributyl(ethyl)azanium Chemical compound OC(=O)\C=C/C([O-])=O.CCCC[N+](CC)(CCCC)CCCC XMALBEDLRZUOAZ-BTJKTKAUSA-M 0.000 claims description 2
- GTLCBNAEKSKWOO-KSBRXOFISA-L (z)-but-2-enedioate;ethyl(trimethyl)azanium Chemical compound CC[N+](C)(C)C.CC[N+](C)(C)C.[O-]C(=O)\C=C/C([O-])=O GTLCBNAEKSKWOO-KSBRXOFISA-L 0.000 claims description 2
- ZFIJMOAWKIHRPN-KSBRXOFISA-L (z)-but-2-enedioate;ethyl(tripropyl)azanium Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCC[N+](CC)(CCC)CCC.CCC[N+](CC)(CCC)CCC ZFIJMOAWKIHRPN-KSBRXOFISA-L 0.000 claims description 2
- JEWIULGLRSNWFL-BTJKTKAUSA-M (z)-but-2-enedioate;hydron;tetramethylazanium Chemical compound C[N+](C)(C)C.OC(=O)\C=C/C([O-])=O JEWIULGLRSNWFL-BTJKTKAUSA-M 0.000 claims description 2
- GQMAJLUQOPVNET-BTJKTKAUSA-M (z)-but-2-enedioate;hydron;triethyl(methyl)azanium Chemical compound CC[N+](C)(CC)CC.OC(=O)\C=C/C([O-])=O GQMAJLUQOPVNET-BTJKTKAUSA-M 0.000 claims description 2
- IBQYJXBNELPBNT-KSBRXOFISA-L (z)-but-2-enedioate;tetrabutylazanium Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC IBQYJXBNELPBNT-KSBRXOFISA-L 0.000 claims description 2
- JAQVWVXBBKQVNN-KSBRXOFISA-L (z)-but-2-enedioate;tetraethylazanium Chemical compound [O-]C(=O)\C=C/C([O-])=O.CC[N+](CC)(CC)CC.CC[N+](CC)(CC)CC JAQVWVXBBKQVNN-KSBRXOFISA-L 0.000 claims description 2
- RGHYVCDOGZOTBL-KSBRXOFISA-L (z)-but-2-enedioate;tetrapropylazanium Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCC[N+](CCC)(CCC)CCC.CCC[N+](CCC)(CCC)CCC RGHYVCDOGZOTBL-KSBRXOFISA-L 0.000 claims description 2
- ZQFHXXWPFJMNPV-UHFFFAOYSA-M 2-methylprop-2-enoate;methyl(tripropyl)azanium Chemical compound CC(=C)C([O-])=O.CCC[N+](C)(CCC)CCC ZQFHXXWPFJMNPV-UHFFFAOYSA-M 0.000 claims description 2
- KNKQNHUSXHFZMW-UHFFFAOYSA-M 2-methylprop-2-enoate;tetrabutylazanium Chemical compound CC(=C)C([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC KNKQNHUSXHFZMW-UHFFFAOYSA-M 0.000 claims description 2
- NFJPGAYVLKHSGE-UHFFFAOYSA-M 2-methylprop-2-enoate;tetramethylazanium Chemical compound C[N+](C)(C)C.CC(=C)C([O-])=O NFJPGAYVLKHSGE-UHFFFAOYSA-M 0.000 claims description 2
- JUGSHJKLELFBDM-UHFFFAOYSA-M 2-methylprop-2-enoate;tetrapropylazanium Chemical compound CC(=C)C([O-])=O.CCC[N+](CCC)(CCC)CCC JUGSHJKLELFBDM-UHFFFAOYSA-M 0.000 claims description 2
- RFIIUAJGZZBDSD-UHFFFAOYSA-M 2-methylprop-2-enoate;triethyl(methyl)azanium Chemical compound CC(=C)C([O-])=O.CC[N+](C)(CC)CC RFIIUAJGZZBDSD-UHFFFAOYSA-M 0.000 claims description 2
- BBBUPMCTLFFTLU-UHFFFAOYSA-M 2-methylprop-2-enoate;trimethyl(propyl)azanium Chemical compound CC(=C)C([O-])=O.CCC[N+](C)(C)C BBBUPMCTLFFTLU-UHFFFAOYSA-M 0.000 claims description 2
- OHSOKNZTSUZROL-JITBQSAISA-L C(\C=C\C(=O)[O-])(=O)[O-].C[N+](CC)(C)C.[K+] Chemical compound C(\C=C\C(=O)[O-])(=O)[O-].C[N+](CC)(C)C.[K+] OHSOKNZTSUZROL-JITBQSAISA-L 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- 239000001747 Potassium fumarate Substances 0.000 claims description 2
- YQQARFSQTHNBDS-UHFFFAOYSA-M butyl(trimethyl)azanium;2-methylprop-2-enoate Chemical compound CC(=C)C([O-])=O.CCCC[N+](C)(C)C YQQARFSQTHNBDS-UHFFFAOYSA-M 0.000 claims description 2
- ODLZOWNZLSFCNT-UHFFFAOYSA-M butyl(trimethyl)azanium;prop-2-enoate Chemical compound [O-]C(=O)C=C.CCCC[N+](C)(C)C ODLZOWNZLSFCNT-UHFFFAOYSA-M 0.000 claims description 2
- RQFVVTLEURLCHV-UHFFFAOYSA-M butyl(tripropyl)azanium;2-methylprop-2-enoate Chemical compound CC(=C)C([O-])=O.CCCC[N+](CCC)(CCC)CCC RQFVVTLEURLCHV-UHFFFAOYSA-M 0.000 claims description 2
- NDMZUIOASOKRLM-UHFFFAOYSA-M butyl(tripropyl)azanium;prop-2-enoate Chemical compound [O-]C(=O)C=C.CCCC[N+](CCC)(CCC)CCC NDMZUIOASOKRLM-UHFFFAOYSA-M 0.000 claims description 2
- ZUIISDIYMJZVCG-WLHGVMLRSA-M ethyl(trimethyl)azanium;(e)-4-hydroxy-4-oxobut-2-enoate Chemical compound [H+].CC[N+](C)(C)C.[O-]C(=O)\C=C\C([O-])=O ZUIISDIYMJZVCG-WLHGVMLRSA-M 0.000 claims description 2
- ZUIISDIYMJZVCG-BTJKTKAUSA-M ethyl(trimethyl)azanium;(z)-4-hydroxy-4-oxobut-2-enoate Chemical compound CC[N+](C)(C)C.OC(=O)\C=C/C([O-])=O ZUIISDIYMJZVCG-BTJKTKAUSA-M 0.000 claims description 2
- JQPARKNWUCPYTK-UHFFFAOYSA-M ethyl(trimethyl)azanium;2-methylprop-2-enoate Chemical compound CC[N+](C)(C)C.CC(=C)C([O-])=O JQPARKNWUCPYTK-UHFFFAOYSA-M 0.000 claims description 2
- QYQWWPLGDWOTIM-UHFFFAOYSA-M ethyl(trimethyl)azanium;prop-2-enoate Chemical compound [O-]C(=O)C=C.CC[N+](C)(C)C QYQWWPLGDWOTIM-UHFFFAOYSA-M 0.000 claims description 2
- ZNAZTTDDAICXNE-BTJKTKAUSA-M ethyl(tripropyl)azanium;(z)-4-hydroxy-4-oxobut-2-enoate Chemical compound OC(=O)\C=C/C([O-])=O.CCC[N+](CC)(CCC)CCC ZNAZTTDDAICXNE-BTJKTKAUSA-M 0.000 claims description 2
- UARUINOVQHEYKN-UHFFFAOYSA-M methyl(tripropyl)azanium;iodide Chemical group [I-].CCC[N+](C)(CCC)CCC UARUINOVQHEYKN-UHFFFAOYSA-M 0.000 claims description 2
- QQQVTKCSPZOPOT-UHFFFAOYSA-M methyl(tripropyl)azanium;prop-2-enoate Chemical compound [O-]C(=O)C=C.CCC[N+](C)(CCC)CCC QQQVTKCSPZOPOT-UHFFFAOYSA-M 0.000 claims description 2
- 229920001296 polysiloxane Polymers 0.000 claims description 2
- GYLQTGGHYFJOHY-UHFFFAOYSA-M potassium (E)-4-(2,2-dimethylpropoxy)-4-oxobut-2-enoate Chemical compound C(C=CC(=O)[O-])(=O)OCC(C)(C)C.[K+] GYLQTGGHYFJOHY-UHFFFAOYSA-M 0.000 claims description 2
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- OZJPDTNDVBHLNU-UHFFFAOYSA-M 4,4-dimethylpentanoate triethyl(methyl)azanium Chemical compound CC[N+](C)(CC)CC.CC(C)(C)CCC([O-])=O OZJPDTNDVBHLNU-UHFFFAOYSA-M 0.000 description 1
- ZUQQFBUKZZKFIF-UHFFFAOYSA-M 4,4-dimethylpentanoate trimethyl(propyl)azanium Chemical compound CCC[N+](C)(C)C.CC(C)(C)CCC([O-])=O ZUQQFBUKZZKFIF-UHFFFAOYSA-M 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- VQIAWQKBOAUGHE-UHFFFAOYSA-N 4-propylheptan-4-amine Chemical compound CCCC(N)(CCC)CCC VQIAWQKBOAUGHE-UHFFFAOYSA-N 0.000 description 1
- GYQQDOLSOPZVHG-UHFFFAOYSA-M 5,5-dimethylhexanoate ethyl(trimethyl)azanium Chemical compound CC[N+](C)(C)C.CC(C)(C)CCCC([O-])=O GYQQDOLSOPZVHG-UHFFFAOYSA-M 0.000 description 1
- JDHGDPCRSIKPIB-UHFFFAOYSA-M 5,5-dimethylhexanoate methyl(tripropyl)azanium Chemical compound CC(C)(C)CCCC([O-])=O.CCC[N+](C)(CCC)CCC JDHGDPCRSIKPIB-UHFFFAOYSA-M 0.000 description 1
- GIWNUIUAZASMPW-UHFFFAOYSA-M 5,5-dimethylhexanoate tetrabutylazanium Chemical compound CC(C)(C)CCCC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC GIWNUIUAZASMPW-UHFFFAOYSA-M 0.000 description 1
- BEMNPJSJBMDCMB-UHFFFAOYSA-M 5,5-dimethylhexanoate tetraethylazanium Chemical compound CC[N+](CC)(CC)CC.CC(C)(C)CCCC([O-])=O BEMNPJSJBMDCMB-UHFFFAOYSA-M 0.000 description 1
- KLOSPLMOMQLIIR-UHFFFAOYSA-M 5,5-dimethylhexanoate tetramethylazanium Chemical compound C[N+](C)(C)C.CC(C)(C)CCCC([O-])=O KLOSPLMOMQLIIR-UHFFFAOYSA-M 0.000 description 1
- TZJZZAIOYZDILR-UHFFFAOYSA-M 5,5-dimethylhexanoate tetrapropylazanium Chemical compound CC(C)(C)CCCC([O-])=O.CCC[N+](CCC)(CCC)CCC TZJZZAIOYZDILR-UHFFFAOYSA-M 0.000 description 1
- ZKGAVMQDFDBLPX-UHFFFAOYSA-M 5,5-dimethylhexanoate triethyl(methyl)azanium Chemical compound CC[N+](C)(CC)CC.CC(C)(C)CCCC([O-])=O ZKGAVMQDFDBLPX-UHFFFAOYSA-M 0.000 description 1
- RHSDBKAWECINGB-UHFFFAOYSA-M 5,5-dimethylhexanoate trimethyl(propyl)azanium Chemical compound CCC[N+](C)(C)C.CC(C)(C)CCCC([O-])=O RHSDBKAWECINGB-UHFFFAOYSA-M 0.000 description 1
- VBHRLSQLJDHSCO-UHFFFAOYSA-N 5,5-dimethylhexanoic acid Chemical compound CC(C)(C)CCCC(O)=O VBHRLSQLJDHSCO-UHFFFAOYSA-N 0.000 description 1
- YPIFGDQKSSMYHQ-UHFFFAOYSA-M 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC([O-])=O YPIFGDQKSSMYHQ-UHFFFAOYSA-M 0.000 description 1
- ORVNPHJEDYAKQC-UHFFFAOYSA-M 7,7-dimethyloctanoate ethyl(trimethyl)azanium Chemical compound CC[N+](C)(C)C.CC(C)(C)CCCCCC([O-])=O ORVNPHJEDYAKQC-UHFFFAOYSA-M 0.000 description 1
- MGOWJKGCTZTNAS-UHFFFAOYSA-M 7,7-dimethyloctanoate methyl(tripropyl)azanium Chemical compound CCC[N+](C)(CCC)CCC.CC(C)(C)CCCCCC([O-])=O MGOWJKGCTZTNAS-UHFFFAOYSA-M 0.000 description 1
- YDMDCVPQHIJHGV-UHFFFAOYSA-M 7,7-dimethyloctanoate tetrabutylazanium Chemical compound CC(C)(C)CCCCCC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC YDMDCVPQHIJHGV-UHFFFAOYSA-M 0.000 description 1
- CBMMNVUMIHGVQG-UHFFFAOYSA-M 7,7-dimethyloctanoate tetraethylazanium Chemical compound CC[N+](CC)(CC)CC.CC(C)(C)CCCCCC([O-])=O CBMMNVUMIHGVQG-UHFFFAOYSA-M 0.000 description 1
- DAFCZHYVDVCXRP-UHFFFAOYSA-M 7,7-dimethyloctanoate tetramethylazanium Chemical compound C[N+](C)(C)C.CC(C)(C)CCCCCC([O-])=O DAFCZHYVDVCXRP-UHFFFAOYSA-M 0.000 description 1
- ZHRWWTRLAOBACK-UHFFFAOYSA-M 7,7-dimethyloctanoate tetrapropylazanium Chemical compound CC(C)(C)CCCCCC([O-])=O.CCC[N+](CCC)(CCC)CCC ZHRWWTRLAOBACK-UHFFFAOYSA-M 0.000 description 1
- RSIMEAXOUQFPSD-UHFFFAOYSA-M 7,7-dimethyloctanoate triethyl(methyl)azanium Chemical compound CC[N+](C)(CC)CC.CC(C)(C)CCCCCC([O-])=O RSIMEAXOUQFPSD-UHFFFAOYSA-M 0.000 description 1
- NKCJMPVSHUCQDV-UHFFFAOYSA-M 7,7-dimethyloctanoate trimethyl(propyl)azanium Chemical compound CCC[N+](C)(C)C.CC(C)(C)CCCCCC([O-])=O NKCJMPVSHUCQDV-UHFFFAOYSA-M 0.000 description 1
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 description 1
- FZUWYUIYVKESIP-UHFFFAOYSA-N 9,9-dimethyldecanoic acid Chemical compound CC(C)(C)CCCCCCCC(O)=O FZUWYUIYVKESIP-UHFFFAOYSA-N 0.000 description 1
- PCVAKFVNCSPYNN-UHFFFAOYSA-N 9:0(8Me,8Me) Chemical compound CC(C)(C)CCCCCCC(O)=O PCVAKFVNCSPYNN-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- GSCCALZHGUWNJW-UHFFFAOYSA-N N-Cyclohexyl-N-methylcyclohexanamine Chemical compound C1CCCCC1N(C)C1CCCCC1 GSCCALZHGUWNJW-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
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- 229910000831 Steel Inorganic materials 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- ZCQXRORGVYXZCD-UHFFFAOYSA-M butyl(trimethyl)azanium 4,4-dimethylpentanoate Chemical compound CCCC[N+](C)(C)C.CC(C)(C)CCC([O-])=O ZCQXRORGVYXZCD-UHFFFAOYSA-M 0.000 description 1
- UENDBJIWZKSFEZ-UHFFFAOYSA-M butyl(trimethyl)azanium 5,5-dimethylhexanoate Chemical compound CCCC[N+](C)(C)C.CC(C)(C)CCCC([O-])=O UENDBJIWZKSFEZ-UHFFFAOYSA-M 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- SHPKCSFVQGSAJU-UAIGNFCESA-L dipotassium;(z)-but-2-enedioate Chemical compound [K+].[K+].[O-]C(=O)\C=C/C([O-])=O SHPKCSFVQGSAJU-UAIGNFCESA-L 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- WNDZCAKTONJEEI-UHFFFAOYSA-M methyl(tripropyl)azanium;acetate Chemical compound CC([O-])=O.CCC[N+](C)(CCC)CCC WNDZCAKTONJEEI-UHFFFAOYSA-M 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000007777 multifunctional material Substances 0.000 description 1
- DWFKOMDBEKIATP-UHFFFAOYSA-N n'-[2-[2-(dimethylamino)ethyl-methylamino]ethyl]-n,n,n'-trimethylethane-1,2-diamine Chemical compound CN(C)CCN(C)CCN(C)CCN(C)C DWFKOMDBEKIATP-UHFFFAOYSA-N 0.000 description 1
- SZYLDXKMZNIHDQ-UHFFFAOYSA-N n'-[2-[2-[2-(dimethylamino)ethyl-methylamino]ethyl-methylamino]ethyl]-n,n,n'-trimethylethane-1,2-diamine Chemical compound CN(C)CCN(C)CCN(C)CCN(C)CCN(C)C SZYLDXKMZNIHDQ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 229950010765 pivalate Drugs 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- GBCLTJRGYCIYQD-JITBQSAISA-M potassium;(e)-but-2-enedioate;triethylazanium Chemical compound [K+].CC[NH+](CC)CC.[O-]C(=O)\C=C\C([O-])=O GBCLTJRGYCIYQD-JITBQSAISA-M 0.000 description 1
- HGYSIXLTMOZXCM-FJOGWHKWSA-L potassium;(z)-but-2-enedioate;ethyl(tripropyl)azanium Chemical compound [K+].[O-]C(=O)\C=C/C([O-])=O.CCC[N+](CC)(CCC)CCC HGYSIXLTMOZXCM-FJOGWHKWSA-L 0.000 description 1
- WOOMMQKFCBDPGE-FJOGWHKWSA-L potassium;(z)-but-2-enedioate;tetrabutylazanium Chemical compound [K+].[O-]C(=O)\C=C/C([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC WOOMMQKFCBDPGE-FJOGWHKWSA-L 0.000 description 1
- HEOFSSGSXXPIBR-FJOGWHKWSA-L potassium;(z)-but-2-enedioate;tetraethylazanium Chemical compound [K+].[O-]C(=O)\C=C/C([O-])=O.CC[N+](CC)(CC)CC HEOFSSGSXXPIBR-FJOGWHKWSA-L 0.000 description 1
- WEAIPDDMEQRLCD-FJOGWHKWSA-L potassium;(z)-but-2-enedioate;tributyl(ethyl)azanium Chemical compound [K+].[O-]C(=O)\C=C/C([O-])=O.CCCC[N+](CC)(CCCC)CCCC WEAIPDDMEQRLCD-FJOGWHKWSA-L 0.000 description 1
- NFFVHVMUCDEQNM-FJOGWHKWSA-L potassium;(z)-but-2-enedioate;tributyl(methyl)azanium Chemical compound [K+].[O-]C(=O)\C=C/C([O-])=O.CCCC[N+](C)(CCCC)CCCC NFFVHVMUCDEQNM-FJOGWHKWSA-L 0.000 description 1
- WUHPTBIQBUDTCT-FJOGWHKWSA-L potassium;(z)-but-2-enedioate;triethyl(methyl)azanium Chemical compound [K+].CC[N+](C)(CC)CC.[O-]C(=O)\C=C/C([O-])=O WUHPTBIQBUDTCT-FJOGWHKWSA-L 0.000 description 1
- MBJFOILRLVOXMP-UAIGNFCESA-M potassium;(z)-but-2-enedioate;trimethylazanium Chemical compound [K+].C[NH+](C)C.[O-]C(=O)\C=C/C([O-])=O MBJFOILRLVOXMP-UAIGNFCESA-M 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/09—Processes comprising oligomerisation of isocyanates or isothiocyanates involving reaction of a part of the isocyanate or isothiocyanate groups with each other in the reaction mixture
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Description
(a)次の式(1)を有する立体障害を有するカルボキシレート塩
R1、R2及びR3は、独立して、C1〜C18アルキル、アルケニル、アリール又はアラルキル(それらは、置換されているか又は置換されていない)から選択され;
nは、0〜10の整数であり:そして
Mは、第4級アンモニウムイオンである)又は
(b)次の式(2)を有するα,β−不飽和カルボキシレート塩
X、Y及びZは、独立して、水素原子、メチル、エチル、プロピル、ブチル、ペンチル、ヘキシル、フェニル、トリル、ベンジル、−CO2H又は−CO2Mから選択され:そして
Mは、第4級アンモニウムイオンであり、そして
X、Y又はZが−CO2H又は−CO2Mである場合には、Mもまた、アルカリ金属であることができる)。
当業者が本発明の詳細な説明を理解するために、次の定義を提供する。
PIR−ポリイソシアヌレート
PUR−ポリウレタン
イソシアネートインデックス−用いられるポリイソシアネートの実際の量を、反応混合物中の全ての活性水素と反応するために要求されるポリイソシアネートの化学量論的な量で割り、100を乗ずる。(Eq NCO/活性水素のEq)×100としても知られている。
pphp−ポリオール100重量部あたりの重量部
Air Products and Chemicals,Inc.(APCI)から市販される、DABCO(商標)K15触媒は、ジエチレングリコール中の2−エチルヘキサノエート(オクタン酸カリウムとして公知)の70%溶液である。
APCIから市販される、DABCO TMR(商標)触媒は、エチレングリコール中、2−ヒドロキシプロピルトリメチルアンモニウムオクトエートの75%溶液である。
APCIから市販される、Polycat(商標)触媒は、ウレタン触媒、すなわち、ペンタメチルジエチレントリアミンである。
本発明において用いられる触媒組成物は、次の式(1)を有する立体障害を有するカルボキシレート塩を少なくとも1種含むことができる:
R1、R2及びR3は、独立して、C1〜C18アルキル、アルケニル、アリール又はアラルキル(それらは、置換されているか又は置換されていない)から選択され;
nは、0〜10の整数であり:そして
Mは、テトラアルキルアンモニウムイオンである)。
PIR/PURフォームを製造するために特に有用な本発明の触媒組成物は、少なくとも1種のテトラアルキルアンモニウムα,β−不飽和カルボキシレート塩を含むことができる。さらに、本発明の範囲内の触媒組成物は、次の式(2)を有するα,β−不飽和カルボキシレート塩を少なくとも1種含む:
X、Y及びZは、独立して、C1〜C36アルキル、アルケニル、アリール又はアラルキル(それらは、置換されているか又は置換されていない);−CO2H、−CO2M;又は水素原子から選択され:そして
Mは、上述の立体障害を有するカルボン酸のテトラアルキルアンモニウム塩に関して詳しく説明したようなテトラアルキルアンモニウムイオンであり、そして参照することによりここに組み入れる)。
上記PIR/PURスプレーフォーム生成法において有用であるポリイソシアネートには、ヘキサメチレンジイソシアネート、イソホロンジイソシアネート、フェニレンジイソシアネート、トルエンジイソシアネート(TDI)、ジフェニルメタンジイソシアネート異性体(MDI)、水和されたMDI及び1,5−ナフタリンジイソシアネートが含まれるが、これらに限定されるものではない。例えば、2,4−TDI、2,6−TDI及びそれらの混合物を、本発明において容易に用いることができる。他の好適なジイソシアネートの混合物には、クルードMDI又はPAPI(他の異性体及び類似のより高分子量のポリイソシアネートと共に4,4’−ジフェニルメタンジイソシアネートを含む)として当業界に公知のものが含まれるが、これらに限定されるものではない。本発明の別の態様では、ポリイソシアネートとポリエーテルポリオール又はポリエステルポリオールとを部分的に事前反応させた混合物を含むポリイソシアネートのプレポリマーが好適である。さらに別の態様では、上記ポリイソシアネートは、MDIを含むか、又はMDI若しくはMDIの混合物から本質的に成る。
本発明の目的のため、イソシアネートインデックスは、方程式:
イソシアネートインデックス=(Eq NCO/活性水素のEq)×100
(式中、Eq NCOは、ポリイソシアネート中のNCO官能基の数であり、そして活性水素のEqは、水素原子の当量数である)
で表される。
PIR/PURフォーム生成法において典型的に用いられるポリオールは、ポリアルキレンエーテル及びポリエステルポリオールを含む。上記ポリアルキレンエーテルポリオールは、ポリ(アルキレンオキシド)ポリマー、例えば、ポリ(エチレンオキシド)及びポリ(プロピレンオキシド)ポリマー、並びにジオール及びトリオールを含む、多水酸基化合物に由来する末端ヒドロキシル基を有するコポリマーを含む。これらには、エチレングリコール、プロピレングリコール、1,3−ブタンジオール、1,4−ブタンジオール、1,6−ヘキサンジオール、ネオペンチルグリコール、ジエチレングリコール、ジプロピレングリコール、ペンタエリトリトール、グリセロール、ジグリセロール、トリメチロールプロパン、シクロヘキサンジオール及び糖、例えば、サッカロース並びに低分子量ポリオール様のものが含まれるが、これらに限定されるものではない。
スプレーPIR/PURフォームを製造するフォーム配合物及び方法に従って、単独で又は組み合わせて用いられうる好適な発泡剤には、水、メチレンクロライド、アセトン、ヒドロフルオロカーボン(HFC)、ヒドロクロロフルオロカーボン(HCFC)及び炭化水素が含まれるが、これらに限定されるものではない。HFCの例には、HFC−245fa、HFC−134a及びHFC−365が含まれるが、これらに限定されるものではない;HCFCの実例となる例には、HCFC−141b、HCFC−22及びHCFC123が含まれるが、これらに限定されるものではない。例示的な炭化水素には、n−ペンタン、イソペンタン、シクロペンタン等又はそれらの任意の組み合わせが含まれるが、これらに限定されるものではない。本発明の態様の1つでは、上記発泡剤又は発泡剤の混合物は、少なくとも1種の炭化水素を含む。別の態様では、上記発泡剤は、n−ペンタンを含む。さらに、本発明の別の態様では、上記発泡剤は、n−ペンタン又はn−ペンタンと1種若しくは2種以上の発泡剤との混合物から本質的に成る。
ウレタン触媒は、ポリウレタンを生成するための反応を促進し、そしてPIR/PURフォームを製造するために上記触媒系のさらなる成分及び本発明の組成物として用いることができる。本明細書に用いるために好適なウレタン触媒には、金属塩触媒、例えば、有機錫及びアミン化合物、例えば、トリエチレンジアミン(TEDA)、N−メチルイミダゾール、1,2−ジメチルイミダゾール、N−メチルモルホリン、N−エチルモルホリン、トリエチルアミン、N,N’−ジメチルピペラジン、1,3,5−トリス(ジメチルアミノプロピル)ヘキサヒドロトリアジン、2,4,6−トリス(ジメチルアミノメチル)フェノール、N−メチルジシクロヘキシルアミン、ペンタメチルジプロピレントリアミン、N−メチル−N’−(2−ジメチルアミノ)エチルピペラジン、トリブチルアミン、ペンタメチルジエチレントリアミン、ヘキサメチルトリエチレンテトラアミン、ヘプタメチルテトラエチレンペンタミン、ジメチルアミノシクロヘキシルアミン、ペンタメチルジプロピレントリアミン、トリエタノールアミン、ジメチルエタノールアミン、ビス(ジメチルアミノエチル)エーテル、トリス(3−ジメチルアミノ)プロピルアミン、1,8−ジアザビシクロ[5.4.0]ウンデセン又はそれらの酸ブロックされた誘導体等、並びに任意のそれらの混合物が含まれるが、これらに限定されるものではない。ペンタメチルジエチレントリアミンが、本発明に関連するフォーム用途向けのウレタン触媒として特に有用である。
フォーム製造の際又はフォーム生成物の最終用途に関する要求によっては、種々の添加剤をPIR/PURフォーム配合物に用い、特性を調整することができる。これらには、セル安定化剤、難燃剤、連鎖延長剤、エポキシ樹脂、アクリル樹脂、充填剤、顔料又はそれらの任意の組み合わせが含まれるが、これらに限定されるものではない。当業界に公知の他の混合物又は材料が、上記フォーム配合物に含まれ、そして本発明の範囲内であることが理解される。
本発明は、スプレーフォームPIR/PURフォームを調製するための方法であって、スプレーミキシングヘッド/アプリケーターにおいて、少なくとも1種のポリイソシアネートを、少なくとも1種のポリオール、少なくとも1種の発泡剤、及び立体障害を有するカルボン酸若しくはα,β−不飽和カルボン酸又はその両方のテトラアルキルアンモニウム塩を少なくとも1種含む有効量の触媒組成物を含むポリオール成分と接触させることを含む方法を提供する。上記組成物は、少なくとも1種のウレタン触媒をさらに含むことができる。同様に、上記組成物は、少なくとも1種のセル安定化剤、少なくとも1種の難燃剤、少なくとも1種の連鎖延長剤、少なくとも1種のエポキシ樹脂、少なくとも1種のアクリル樹脂、少なくとも1種の充填剤、少なくとも1種の顔料又はそれらの任意の組み合わせから選択される、少なくとも1つの添加剤をさらに含むことができる。次いで、上記スプレーヘッド/アプリケーターにより、好適な表面、例えば、木材、プラスチック、コンクリート又は金属上に上記フォーム組成物をスプレーする。
上述のように、上記発泡剤は、上記触媒組成物がテトラアルキルアンモニウムカルボキシレート塩を含む場合には、クロロフルオロカーボン(CFC)ではない。
Claims (9)
- ポリイソシアヌレート/ポリウレタンスプレーフォームの製造法であって、
スプレーミキシングヘッド内で、n−ペンタン、イソペンタン、シクロペンタン、及びそれらの任意の組み合わせから成る群から選択される発泡剤の存在下で、ポリイソシアネートと、少なくとも1種のポリオール、及び次の式(2):
X、Y及びZは、独立して、C1〜C36アルキル、アルケニル、アリール又はアラルキル(それらは、置換されているか又は置換されていない);−CO2H;−CO2M;又は水素原子であり、そして
Mはテトラアルキルアンモニウムイオンであるが、ただし
X、Y又はZが−CO2Mの場合には、X、Y又はZにおける−CO 2 MのMはアルカリ金属であることができる)
のα,β−不飽和カルボキシレート塩を少なくとも1種含む三量化反応を触媒するための有効量の触媒組成物を含むポリオール組成物とを接触させることにより製造された組成物を、表面にスプレーすることを含む、
前記製造法。 - 少なくとも1種のウレタン触媒をさらに含む、請求項1に記載の方法。
- X、Y及びZが、独立して、水素原子、メチル、エチル、プロピル、ブチル、ペンチル、ヘキシル、フェニル、トリル、ベンジル、−CO2H、又は−CO2Mから選択される、請求項1又は2に記載の方法。
- Mが、テトラメチルアンモニウム、テトラエチルアンモニウム、トリメチルエチルアンモニウム、トリエチルメチルアンモニウム、テトラプロピルアンモニウム、トリメチルプロピルアンモニウム、トリプロピルメチルアンモニウム、トリブチルメチルアンモニウム、トリメチルブチルアンモニウム、トリブチルエチルアンモニウム、トリブチルプロピルアンモニウム又はテトラブチルアンモニウムである、請求項1〜3のいずれか一項に記載の方法。
- 前記α,β−不飽和カルボキシレート塩が、アクリル酸の塩、メタクリル酸の塩、フマル酸の塩、マレインの塩、又はそれらの任意の組み合わせである、請求項1〜4のいずれか一項に記載の方法。
- 前記α,β−不飽和カルボキシレート塩が、テトラメチルアンモニウムアクリレート、テトラエチルアンモニウムアクリレート、テトラプロピルアンモニウムアクリレート、テトラブチルアンモニウムアクリレート、トリメチルエチルアンモニウムアクリレート、トリエチルメチルアンモニウムアクリレート、トリプロピルメチルアンモニウムアクリレート、トリメチルプロピルアンモニウムアクリレート、トリメチルブチルアンモニウムアクリレート、トリブチルメチルアンモニウムアクリレート、トリエチルブチルアンモニウムアクリレート、トリブチルエチルアンモニウムアクリレート、トリブチルプロピルアンモニウムアクリレート、トリプロピルブチルアンモニウムアクリレート、テトラメチルアンモニウムメタクリレート、テトラエチルアンモニウムメタクリレート、テトラプロピルアンモニウムメタクリレート、テトラブチルアンモニウムメタクリレート、トリメチルエチルアンモニウムメタクリレート、トリエチルメチルアンモニウムメタクリレート、トリプロピルメチルアンモニウムメタクリレート、トリメチルプロピルアンモニウムメタクリレート、トリメチルブチルアンモニウムメタクリレート、トリブチルメチルアンモニウムメタクリレート、トリエチルブチルアンモニウムアクリレート、トリブチルエチルアンモニウムメタクリレート、トリブチルプロピルアンモニウムメタクリレート、トリプロピルブチルアンモニウムメタクリレート、モノ(テトラメチルアンモニウム)フマレート、ビス(テトラメチルアンモニウム)フマレート、フマル酸カリウムテトラメチルアンモニウム、モノ(トリメチルエチルアンモニウム)フマレート、ビス(トリメチルエチルアンモニウム)フマレート、モノ(トリエチルメチルアンモニウム)フマレート、フマル酸カリウムトリエチルメチルアンモニウム、フマル酸カリウムトリメチルエチルアンモニウム、モノ(テトラエチルアンモニウム)フマレート、ビス(テトラエチルアンモニウム)フマレート、フマル酸カリウムテトラエチルアンモニウム、モノ(テトラプロピルアンモニウム)フマレート、ビス(テトラプロピルアンモニウム)フマレート、フマル酸カリウムテトラプロピルアンモニウム、ビス(トリプロピルメチルアンモニウム)フマレート、モノ(トリプロピルエチルアンモニウム)フマレート、フマル酸カリウムトリプロピルメチルアンモニウム、ビス(トリプロピルエチルアンモニウム)フマレート、モノ(トリプロピルエチルアンモニウム)フマレート、フマル酸カリウムトリプロピルエチルアンモニウム、ビス(トリプロピルメチルアンモニウムフマレート)、モノ(トリプロピルメチルアンモニウム)フマレート、フマル酸カリウムトリプロピルメチルアンモニウム、モノ(テトラブチルアンモニウム)フマレート、ビス(テトラブチルアンモニウム)フマレート、フマル酸カリウムテトラブチルアンモニウム、ビス(トリブチルメチルアンモニウム)フマレート、モノ(トリブチルメチルアンモニウム)フマレート、フマル酸カリウムトリブチルメチルアンモニウム、ビス(トリブチルエチルアンモニウム)フマレート、モノ(トリブチルエチルアンモニウム)フマレート、フマル酸カリウムトリブチルエチルアンモニウム、モノ(テトラメチルアンモニウム)マレエート、ビス(テトラメチルアンモニウム)マレエート、マレイン酸カリウムテトラメチルアンモニウム、モノ(トリメチルエチルアンモニウム)マレエート、ビス(トリメチルエチルアンモニウム)マレエート、モノ(トリエチルメチルアンモニウム)マレエート、フマル酸カリウムトリエチルメチルアンモニウム、フマル酸カリウムトリメチルエチル、モノ(テトラエチルアンモニウム)マレエート、ビス(テトラエチルアンモニウム)マレエート、フマル酸カリウムテトラエチルアンモニウム、モノ(テトラプロピルアンモニウム)マレエート、ビス(テトラプロピルアンモニウム)マレエート、フマル酸カリウムテトラプロピルアンモニウム、ビス(トリプロピルメチルアンモニウム)マレエート、モノ(トリプロピルメチルアンモニウム)マレエート、フマル酸カリウムトリプロピルメチルアンモニウム、ビス(トリプロピルエチルアンモニウム)マレエート、モノ(トリプロピルエチルアンモニウム)マレエート、フマル酸カリウムトリプロピルエチルアンモニウム、ビス(トリプロピルメチルアンモニウムマレエート)、モノ(トリプロピルメチルアンモニウム)マレエート、フマル酸カリウムトリプロピルメチルアンモニウム、モノ(テトラブチルアンモニウム)マレエート、ビス(テトラブチルアンモニウム)マレエート、フマル酸カリウムテトラブチルアンモニウム、ビス(トリブチルエチルアンモニウム)マレエート、モノ(トリブチルメチルアンモニウム)マレエート、フマル酸カリウムトリブチルメチルアンモニウム、ビス(トリブチルエチルアンモニウム)マレエート、モノ(トリブチルエチルアンモニウム)マレエート、フマル酸カリウムトリブチルエチルアンモニウム、又はそれらの任意の組み合わせである、請求項1〜5のいずれか一項に記載の方法。
- 前記α,β−不飽和カルボキシレート塩が、テトラメチルアンモニウムアクリレート又はテトラメチルアンモニウムマレエートである、請求項1〜6のいずれか一項に記載の方法。
- ポリイソシアヌレート/ポリウレタンスプレーフォームの調製法であって、
スプレーミキシングヘッド内で、n−ペンタン、イソペンタン、シクロペンタン、及びそれらの任意の組み合わせから成る群から選択される発泡剤の存在下で、少なくとも1種のポリイソシアネートと、少なくとも1種のポリオール、及び次の式(2):
X、Y及びZは、独立して、C1〜C36アルキル、アルケニル、アリール又はアラルキル(それらは、置換されているか又は置換されていない);−CO2H;−CO2M;又は水素原子であり、そして
Mはテトラアルキルアンモニウムイオンであるが、ただし
X、Y又はZが−CO2Mの場合には、X、Y又はZにおける−CO 2 MのMはアルカリ金属であることができる)
のα,β−不飽和カルボキシレート塩を少なくとも1種含む有効量の触媒組成物を含むポリオール組成物とを接触させるステップ、そして
表面上に接触生成物をスプレーするステップ、
を含む、前記調製法。 - 前記ポリイソシアネート及び前記ポリオール組成物が、次の成分:
成分 重量部(pphp)
ポリエステルポリオール 10 〜100
マンニッヒポリオール 0 〜 90
ポリエーテルポリオール 0 〜 90
発泡剤 5 〜 40
シリコーン界面活性剤 0.2〜 5
水 0 〜 10
アミン触媒 0 〜 20
金属触媒 0 〜 20
三量化触媒 0.1〜 10
イソシアネートインデックス(NCOインデックス) 80 〜500
(ここで、前記三量化触媒は、式(2)のα,β−不飽和カルボキシレート塩である)を含む、請求項1〜8のいずれか一項に記載の方法。
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US11/762,360 US20080312351A1 (en) | 2007-06-13 | 2007-06-13 | Tetraalkylammonium Carboxylate Salts as Trimerization Catalysts for Spray Foam Applications |
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EP (1) | EP2003157A3 (ja) |
JP (1) | JP5452890B2 (ja) |
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KR100958876B1 (ko) | 2008-04-02 | 2010-05-20 | 삼성엔지니어링 주식회사 | 다양한 극성/비극성 용매 혼화성 이온성 액체 및 그의제조방법 |
TW201542682A (zh) * | 2014-02-27 | 2015-11-16 | Sekisui Chemical Co Ltd | 用以現場形成難燃性聚胺酯發泡體之現場發泡系統 |
JP6651552B2 (ja) * | 2015-06-18 | 2020-02-19 | エボニック オペレーションズ ゲーエムベーハー | 立体障害性塩およびイソシアネート反応性基を有する第三級アミンからの三量体化触媒 |
WO2018105730A1 (ja) * | 2016-12-08 | 2018-06-14 | 積水化学工業株式会社 | ウレタン樹脂組成物 |
JP7453739B2 (ja) * | 2018-03-26 | 2024-03-21 | 積水化学工業株式会社 | ポリオール含有組成物、及びポリウレタンフォーム |
JP7478048B2 (ja) | 2019-07-08 | 2024-05-02 | 積水化学工業株式会社 | ポリオール含有組成物、発泡性ポリウレタン組成物及びポリウレタンフォーム |
CN110560159B (zh) * | 2019-08-13 | 2020-10-20 | 清华大学 | 一种用于叔碳酸缩水甘油酯制备的催化剂及其制备方法 |
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US3940517A (en) * | 1973-01-11 | 1976-02-24 | The Celotex Corporation | Polyisocyanurate foam, catalyst composition and process for producing such |
US3993652A (en) * | 1973-07-09 | 1976-11-23 | Air Products And Chemicals, Inc. | Cyclic quaternary hydroxyalkyl phenoxide catalysts for isocyanate reactions |
US3988267A (en) * | 1973-07-09 | 1976-10-26 | Air Products And Chemicals, Inc. | Quaternary hydroxyalkyl tertiary amine bases as polyurethane catalysts |
US3892687A (en) * | 1973-07-09 | 1975-07-01 | Air Prod & Chem | Quaternary hydroxyalkyl tertiary amine bases as poluyrethane catalysts |
US3989651A (en) * | 1974-07-09 | 1976-11-02 | The Upjohn Company | Catalyst for sprayable polyisocyanurate foam composition |
US3954684A (en) * | 1974-07-09 | 1976-05-04 | The Upjohn Company | Foam process using tertiary amine/quaternary ammonium salt catalyst |
US3980594A (en) * | 1975-04-23 | 1976-09-14 | The General Tire & Rubber Company | Trimerization of aromatic isocyanates catalyzed by certain ammonium salts |
US4026840A (en) * | 1975-06-09 | 1977-05-31 | Air Products And Chemicals, Inc. | Hydroxyalkyl tertiary amine catalysts for isocyanate reactions |
US4148980A (en) * | 1977-05-03 | 1979-04-10 | Basf Wyandotte Corporation | Novel carboxylate catalysts for the preparation of foams characterized by polyisocyanurate, polyurethane and poly (urethane-isocyanurate) linkages |
DE2916201A1 (de) * | 1979-04-21 | 1980-10-30 | Huels Chemische Werke Ag | Verfahren zur trimerisierung von diisocyanaten |
US4503226A (en) * | 1984-04-30 | 1985-03-05 | Olin Corporation | Process for trimerizing organic polyisocyanates |
GB8531180D0 (en) * | 1985-12-18 | 1986-01-29 | Ici Plc | Cocatalyst systems |
GB9021051D0 (en) * | 1990-09-27 | 1990-11-07 | Ici Plc | Catalyst composition |
US5321050A (en) * | 1992-08-06 | 1994-06-14 | Nisshinbo Industries, Inc. | Method for producing modified polyisocyanurate foams |
US5691440A (en) * | 1995-10-05 | 1997-11-25 | Arco Chemical Technonogy, L.P. | Catalyst and process for producing isocyanate trimers |
JP4106746B2 (ja) * | 1998-06-24 | 2008-06-25 | 旭硝子株式会社 | 硬質ウレタン変性ポリイソシアヌレートフォームの製造方法、および、ポリオール組成物 |
US20070112085A1 (en) * | 2003-09-29 | 2007-05-17 | Tosoh Corporation | Catalyst composition for production of rigid polyurethane foam and isocyanurate-modified rigid polysurethane foam and raw-material composition containing the same |
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JP2008308689A (ja) | 2008-12-25 |
KR20080109631A (ko) | 2008-12-17 |
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