EP3728386A1 - Procede de preparation d'une composition comprenant un polyurethane a terminaisons nco - Google Patents
Procede de preparation d'une composition comprenant un polyurethane a terminaisons ncoInfo
- Publication number
- EP3728386A1 EP3728386A1 EP18847140.3A EP18847140A EP3728386A1 EP 3728386 A1 EP3728386 A1 EP 3728386A1 EP 18847140 A EP18847140 A EP 18847140A EP 3728386 A1 EP3728386 A1 EP 3728386A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- catalyst
- ppm
- equal
- composition
- diisocyanate
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 227
- 239000004814 polyurethane Substances 0.000 title claims abstract description 55
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 55
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 140
- 150000003077 polyols Chemical class 0.000 claims abstract description 83
- 229920005862 polyol Polymers 0.000 claims abstract description 67
- 238000000034 method Methods 0.000 claims abstract description 45
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 39
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 32
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 32
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000003863 metallic catalyst Substances 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 61
- -1 for example Chemical compound 0.000 claims description 60
- 229910052797 bismuth Inorganic materials 0.000 claims description 39
- 229910052725 zinc Inorganic materials 0.000 claims description 31
- 239000011701 zinc Substances 0.000 claims description 31
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 30
- ZMSQJSMSLXVTKN-UHFFFAOYSA-N 4-[2-(2-morpholin-4-ylethoxy)ethyl]morpholine Chemical compound C1COCCN1CCOCCN1CCOCC1 ZMSQJSMSLXVTKN-UHFFFAOYSA-N 0.000 claims description 29
- 229910052751 metal Inorganic materials 0.000 claims description 28
- 239000002184 metal Substances 0.000 claims description 28
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 25
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 claims description 22
- 150000007942 carboxylates Chemical class 0.000 claims description 22
- 125000002524 organometallic group Chemical group 0.000 claims description 21
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000000945 filler Substances 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 17
- 239000011347 resin Substances 0.000 claims description 17
- 229920005989 resin Polymers 0.000 claims description 17
- 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 15
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 15
- 239000000853 adhesive Substances 0.000 claims description 13
- 230000001070 adhesive effect Effects 0.000 claims description 13
- 239000003153 chemical reaction reagent Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000012974 tin catalyst Substances 0.000 claims description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 claims description 10
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 claims description 10
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 10
- 238000000576 coating method Methods 0.000 claims description 10
- 239000013521 mastic Substances 0.000 claims description 9
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000011248 coating agent Substances 0.000 claims description 8
- 239000000049 pigment Substances 0.000 claims description 8
- 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 8
- 239000003963 antioxidant agent Substances 0.000 claims description 7
- 239000004014 plasticizer Substances 0.000 claims description 7
- JAEQOSKUYPMJAT-UHFFFAOYSA-N 4-(2-methoxyethyl)morpholine Chemical compound COCCN1CCOCC1 JAEQOSKUYPMJAT-UHFFFAOYSA-N 0.000 claims description 6
- XDGWKBYFXMRODP-UHFFFAOYSA-N 4-[2-[2-(2,6-dimethylmorpholin-4-yl)ethoxy]ethyl]-2,6-dimethylmorpholine Chemical compound C1C(C)OC(C)CN1CCOCCN1CC(C)OC(C)C1 XDGWKBYFXMRODP-UHFFFAOYSA-N 0.000 claims description 6
- AZFJDAIILPPZJN-UHFFFAOYSA-N 4-[2-[2-(3,5-dimethylmorpholin-4-yl)ethoxy]ethyl]-3,5-dimethylmorpholine Chemical compound CC1COCC(C)N1CCOCCN1C(C)COCC1C AZFJDAIILPPZJN-UHFFFAOYSA-N 0.000 claims description 6
- 239000006096 absorbing agent Substances 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 6
- 238000010276 construction Methods 0.000 claims description 6
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 6
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims description 5
- BKFRZOZNMWIFLH-UHFFFAOYSA-N 1-decyl-2-methylimidazole Chemical compound CCCCCCCCCCN1C=CN=C1C BKFRZOZNMWIFLH-UHFFFAOYSA-N 0.000 claims description 5
- GMOKBQLJIIVDQQ-UHFFFAOYSA-N 1-dodecyl-2-methylimidazole Chemical compound CCCCCCCCCCCCN1C=CN=C1C GMOKBQLJIIVDQQ-UHFFFAOYSA-N 0.000 claims description 5
- BDHGFCVQWMDIQX-UHFFFAOYSA-N 1-ethenyl-2-methylimidazole Chemical compound CC1=NC=CN1C=C BDHGFCVQWMDIQX-UHFFFAOYSA-N 0.000 claims description 5
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 5
- SEULWJSKCVACTH-UHFFFAOYSA-N 1-phenylimidazole Chemical compound C1=NC=CN1C1=CC=CC=C1 SEULWJSKCVACTH-UHFFFAOYSA-N 0.000 claims description 5
- XLXCHZCQTCBUOX-UHFFFAOYSA-N 1-prop-2-enylimidazole Chemical compound C=CCN1C=CN=C1 XLXCHZCQTCBUOX-UHFFFAOYSA-N 0.000 claims description 5
- QALONTJVPVYYJN-UHFFFAOYSA-N 2-(hydroxymethyl)-1-azabicyclo[2.2.2]octan-2-ol Chemical compound OCC1(O)CC2CCN1CC2 QALONTJVPVYYJN-UHFFFAOYSA-N 0.000 claims description 5
- YSAANLSYLSUVHB-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]ethanol Chemical compound CN(C)CCOCCO YSAANLSYLSUVHB-UHFFFAOYSA-N 0.000 claims description 5
- SFDRINJYDQTXRF-UHFFFAOYSA-N 2-[bis(dimethylamino)methyl]phenol Chemical compound CN(C)C(N(C)C)C1=CC=CC=C1O SFDRINJYDQTXRF-UHFFFAOYSA-N 0.000 claims description 5
- WAPWXMDDHHWKNM-UHFFFAOYSA-N 3-[2,3-bis[3-(dimethylamino)propyl]triazinan-1-yl]-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCN1CCCN(CCCN(C)C)N1CCCN(C)C WAPWXMDDHHWKNM-UHFFFAOYSA-N 0.000 claims description 5
- QEOGKTCJGDHZDW-UHFFFAOYSA-N 3-[2-(dimethylamino)ethoxy]-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCOCCN(C)C QEOGKTCJGDHZDW-UHFFFAOYSA-N 0.000 claims description 5
- IVLICPVPXWEGCA-UHFFFAOYSA-N 3-quinuclidinol Chemical compound C1C[C@@H]2C(O)C[N@]1CC2 IVLICPVPXWEGCA-UHFFFAOYSA-N 0.000 claims description 5
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 claims description 5
- RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 claims description 5
- 239000012963 UV stabilizer Substances 0.000 claims description 5
- UVKJPLPLHHNSFL-UHFFFAOYSA-N bismuth;ethyl hexanoate Chemical compound [Bi].CCCCCC(=O)OCC UVKJPLPLHHNSFL-UHFFFAOYSA-N 0.000 claims description 5
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims description 5
- WLUJHMKCLOIRSK-UHFFFAOYSA-N 1,2,4,5-tetramethylimidazole Chemical compound CC=1N=C(C)N(C)C=1C WLUJHMKCLOIRSK-UHFFFAOYSA-N 0.000 claims description 4
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 claims description 4
- QJWQYVJVCXMTJP-UHFFFAOYSA-N 4-pyridin-4-ylmorpholine Chemical compound C1COCCN1C1=CC=NC=C1 QJWQYVJVCXMTJP-UHFFFAOYSA-N 0.000 claims description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 4
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
- 150000004703 alkoxides Chemical class 0.000 claims description 4
- NSPSPMKCKIPQBH-UHFFFAOYSA-K bismuth;7,7-dimethyloctanoate Chemical compound [Bi+3].CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O NSPSPMKCKIPQBH-UHFFFAOYSA-K 0.000 claims description 4
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 claims description 4
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 4
- 239000001993 wax Substances 0.000 claims description 4
- VNTDZUDTQCZFKN-UHFFFAOYSA-L zinc 2,2-dimethyloctanoate Chemical compound [Zn++].CCCCCCC(C)(C)C([O-])=O.CCCCCCC(C)(C)C([O-])=O VNTDZUDTQCZFKN-UHFFFAOYSA-L 0.000 claims description 4
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 claims description 3
- XFPRKNQSYRZNRI-UHFFFAOYSA-N 4-(isocyanatomethyl)bicyclo[2.2.1]heptane Chemical compound C1CC2CCC1(CN=C=O)C2 XFPRKNQSYRZNRI-UHFFFAOYSA-N 0.000 claims description 3
- LNWBFIVSTXCJJG-UHFFFAOYSA-N [diisocyanato(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(N=C=O)(N=C=O)C1=CC=CC=C1 LNWBFIVSTXCJJG-UHFFFAOYSA-N 0.000 claims description 3
- 239000002318 adhesion promoter Substances 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 239000003063 flame retardant Substances 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 239000013110 organic ligand Substances 0.000 claims description 3
- 239000006254 rheological additive Substances 0.000 claims description 3
- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 claims description 3
- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 claims description 2
- 239000005059 1,4-Cyclohexyldiisocyanate Substances 0.000 claims description 2
- ROHUXHMNZLHBSF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCC(CN=C=O)CC1 ROHUXHMNZLHBSF-UHFFFAOYSA-N 0.000 claims description 2
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 claims description 2
- AHBNSOZREBSAMG-UHFFFAOYSA-N 1,5-diisocyanato-2-methylpentane Chemical compound O=C=NCC(C)CCCN=C=O AHBNSOZREBSAMG-UHFFFAOYSA-N 0.000 claims description 2
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 claims description 2
- QGLRLXLDMZCFBP-UHFFFAOYSA-N 1,6-diisocyanato-2,4,4-trimethylhexane Chemical compound O=C=NCC(C)CC(C)(C)CCN=C=O QGLRLXLDMZCFBP-UHFFFAOYSA-N 0.000 claims description 2
- BYPFICORERPGJY-UHFFFAOYSA-N 3,4-diisocyanatobicyclo[2.2.1]hept-2-ene Chemical compound C1CC2(N=C=O)C(N=C=O)=CC1C2 BYPFICORERPGJY-UHFFFAOYSA-N 0.000 claims description 2
- WJIOHMVWGVGWJW-UHFFFAOYSA-N 3-methyl-n-[4-[(3-methylpyrazole-1-carbonyl)amino]butyl]pyrazole-1-carboxamide Chemical compound N1=C(C)C=CN1C(=O)NCCCCNC(=O)N1N=C(C)C=C1 WJIOHMVWGVGWJW-UHFFFAOYSA-N 0.000 claims description 2
- JRQLZCFSWYQHPI-UHFFFAOYSA-N 4,5-dichloro-2-cyclohexyl-1,2-thiazol-3-one Chemical compound O=C1C(Cl)=C(Cl)SN1C1CCCCC1 JRQLZCFSWYQHPI-UHFFFAOYSA-N 0.000 claims description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 2
- HDONYZHVZVCMLR-UHFFFAOYSA-N N=C=O.N=C=O.CC1CCCCC1 Chemical compound N=C=O.N=C=O.CC1CCCCC1 HDONYZHVZVCMLR-UHFFFAOYSA-N 0.000 claims description 2
- CLWKGFMSGOQXNJ-UHFFFAOYSA-N N=C=O.N=C=O.CCC1(CC)CCCCC1C Chemical compound N=C=O.N=C=O.CCC1(CC)CCCCC1C CLWKGFMSGOQXNJ-UHFFFAOYSA-N 0.000 claims description 2
- QCJBVWNJRIOSDN-UHFFFAOYSA-N N=C=O.N=C=O.CCC1CCCCC1 Chemical compound N=C=O.N=C=O.CCC1CCCCC1 QCJBVWNJRIOSDN-UHFFFAOYSA-N 0.000 claims description 2
- GNFBHJRVKAKFNZ-UHFFFAOYSA-N N=C=O.N=C=O.CCCC1CCCCC1 Chemical compound N=C=O.N=C=O.CCCC1CCCCC1 GNFBHJRVKAKFNZ-UHFFFAOYSA-N 0.000 claims description 2
- OEMVAFGEQGKIOR-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCCCC Chemical compound N=C=O.N=C=O.CCCCCCCC OEMVAFGEQGKIOR-UHFFFAOYSA-N 0.000 claims description 2
- FUCRTFHCJZBKBB-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCCCCC Chemical compound N=C=O.N=C=O.CCCCCCCCC FUCRTFHCJZBKBB-UHFFFAOYSA-N 0.000 claims description 2
- DGOMVSNLFKNSAR-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCCCCCC Chemical compound N=C=O.N=C=O.CCCCCCCCCC DGOMVSNLFKNSAR-UHFFFAOYSA-N 0.000 claims description 2
- DSSJCBOUEXFVFJ-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCCCCCCC Chemical compound N=C=O.N=C=O.CCCCCCCCCCC DSSJCBOUEXFVFJ-UHFFFAOYSA-N 0.000 claims description 2
- SGXQOOUIOHVMEJ-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCCCCCCCC Chemical compound N=C=O.N=C=O.CCCCCCCCCCCC SGXQOOUIOHVMEJ-UHFFFAOYSA-N 0.000 claims description 2
- JGCWKVKYRNXTMD-UHFFFAOYSA-N bicyclo[2.2.1]heptane;isocyanic acid Chemical compound N=C=O.N=C=O.C1CC2CCC1C2 JGCWKVKYRNXTMD-UHFFFAOYSA-N 0.000 claims description 2
- TWLCPLJMACDPFF-UHFFFAOYSA-N cyclohexane;1,2-diisocyanatoethane Chemical compound C1CCCCC1.O=C=NCCN=C=O TWLCPLJMACDPFF-UHFFFAOYSA-N 0.000 claims description 2
- 239000012973 diazabicyclooctane Substances 0.000 claims description 2
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005442 diisocyanate group Chemical group 0.000 claims description 2
- STBLQDMGPBQTMI-UHFFFAOYSA-N heptane;isocyanic acid Chemical compound N=C=O.N=C=O.CCCCCCC STBLQDMGPBQTMI-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 239000003446 ligand Substances 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 claims 1
- GNCJRTJOPHONBZ-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1h-imidazole Chemical compound CC1(C)NC=NC1(C)C GNCJRTJOPHONBZ-UHFFFAOYSA-N 0.000 claims 1
- KUZWHTCSPWYNLY-UHFFFAOYSA-N 4-ethylmorpholine;4-methylmorpholine Chemical compound CN1CCOCC1.CCN1CCOCC1 KUZWHTCSPWYNLY-UHFFFAOYSA-N 0.000 claims 1
- 239000003086 colorant Substances 0.000 claims 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 claims 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 19
- 150000002009 diols Chemical class 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 13
- 239000004721 Polyphenylene oxide Substances 0.000 description 12
- 229920000570 polyether Polymers 0.000 description 12
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 11
- 239000002245 particle Substances 0.000 description 10
- 229920005906 polyester polyol Polymers 0.000 description 10
- 229920001451 polypropylene glycol Polymers 0.000 description 10
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 240000005428 Pistacia lentiscus Species 0.000 description 8
- 150000002902 organometallic compounds Chemical class 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 7
- 239000004800 polyvinyl chloride Substances 0.000 description 7
- BKUSIKGSPSFQAC-RRKCRQDMSA-N 2'-deoxyinosine-5'-diphosphate Chemical compound O1[C@H](CO[P@@](O)(=O)OP(O)(O)=O)[C@@H](O)C[C@@H]1N1C(NC=NC2=O)=C2N=C1 BKUSIKGSPSFQAC-RRKCRQDMSA-N 0.000 description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 239000011572 manganese Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 150000003505 terpenes Chemical class 0.000 description 5
- 235000007586 terpenes Nutrition 0.000 description 5
- NXQMCAOPTPLPRL-UHFFFAOYSA-N 2-(2-benzoyloxyethoxy)ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOCCOC(=O)C1=CC=CC=C1 NXQMCAOPTPLPRL-UHFFFAOYSA-N 0.000 description 4
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
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- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920006231 aramid fiber Polymers 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 229910052601 baryte Inorganic materials 0.000 description 1
- 239000010428 baryte Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- SGWHIVHMTJJAGX-UHFFFAOYSA-N bis(10-methylundecyl) benzene-1,2-dicarboxylate Chemical compound CC(C)CCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCC(C)C SGWHIVHMTJJAGX-UHFFFAOYSA-N 0.000 description 1
- TUQRJVHQQXIPMN-UHFFFAOYSA-K bis(2,2-dimethyloctanoyloxy)bismuthanyl 2,2-dimethyloctanoate Chemical compound CCCCCCC(C)(C)C(=O)O[Bi](OC(=O)C(C)(C)CCCCCC)OC(=O)C(C)(C)CCCCCC TUQRJVHQQXIPMN-UHFFFAOYSA-K 0.000 description 1
- CMCJNODIWQEOAI-UHFFFAOYSA-N bis(2-butoxyethyl)phthalate Chemical compound CCCCOCCOC(=O)C1=CC=CC=C1C(=O)OCCOCCCC CMCJNODIWQEOAI-UHFFFAOYSA-N 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- HORIEOQXBKUKGQ-UHFFFAOYSA-N bis(7-methyloctyl) cyclohexane-1,2-dicarboxylate Chemical compound CC(C)CCCCCCOC(=O)C1CCCCC1C(=O)OCCCCCCC(C)C HORIEOQXBKUKGQ-UHFFFAOYSA-N 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- BSDOQSMQCZQLDV-UHFFFAOYSA-N butan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] BSDOQSMQCZQLDV-UHFFFAOYSA-N 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
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical class OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- UCVPKAZCQPRWAY-UHFFFAOYSA-N dibenzyl benzene-1,2-dicarboxylate Chemical compound C=1C=CC=C(C(=O)OCC=2C=CC=CC=2)C=1C(=O)OCC1=CC=CC=C1 UCVPKAZCQPRWAY-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- MGWAVDBGNNKXQV-UHFFFAOYSA-N diisobutyl phthalate Chemical compound CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C MGWAVDBGNNKXQV-UHFFFAOYSA-N 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 229940093858 ethyl acetoacetate Drugs 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 230000000763 evoking effect Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 231100000219 mutagenic Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000010690 paraffinic oil Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004588 polyurethane sealant Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- ZGSOBQAJAUGRBK-UHFFFAOYSA-N propan-2-olate;zirconium(4+) Chemical compound [Zr+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-] ZGSOBQAJAUGRBK-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 231100001260 reprotoxic Toxicity 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 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
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical class CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- UWSYCPWEBZRZNJ-UHFFFAOYSA-N trimethoxy(2,4,4-trimethylpentyl)silane Chemical compound CO[Si](OC)(OC)CC(C)CC(C)(C)C UWSYCPWEBZRZNJ-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- UOKUUKOEIMCYAI-UHFFFAOYSA-N trimethoxysilylmethyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)COC(=O)C(C)=C UOKUUKOEIMCYAI-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical class OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- NRZHJVXFHRINCD-UHFFFAOYSA-K triphenoxybismuthane Chemical compound [Bi+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 NRZHJVXFHRINCD-UHFFFAOYSA-K 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
-
- 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
- C08G18/0895—Manufacture of polymers by continuous processes
-
- 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
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- 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
- C08G18/161—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22
- C08G18/163—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22 covered by C08G18/18 and C08G18/22
-
- 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
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/20—Heterocyclic amines; Salts thereof
- C08G18/2045—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings
- C08G18/2063—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings having two nitrogen atoms in the condensed ring system
-
- 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
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/20—Heterocyclic amines; Salts thereof
- C08G18/2081—Heterocyclic amines; Salts thereof containing at least two non-condensed heterocyclic rings
-
- 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
- C08G18/227—Catalysts containing metal compounds of antimony, bismuth or arsenic
-
- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4804—Two or more polyethers of different physical or chemical nature
- C08G18/4812—Mixtures of polyetherdiols with polyetherpolyols having at least three hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
- C08L75/08—Polyurethanes from polyethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/08—Polyurethanes from polyethers
Definitions
- the present invention relates to a process for preparing a composition comprising an NCO-terminated polyurethane and at least one catalyst.
- the present invention also relates to a composition comprising an NCO-terminated polyurethane and at least one catalyst, and its use as an adhesive, putty or surface coating.
- Mastics are widely used in the field of construction, in particular for assembling - by expansion joints - substrates, for example made of concrete or steel, and allow thanks to their mechanical properties, and in particular elastic, to obtain a stable joint to the dimensional variations induced in particular by the changes of temperature.
- mastics those obtained from polyurethane compositions crosslinkable with moisture. These are commonly prepared by a process involving a polyaddition step in the presence of tin catalyst, such as dioctyltin dilaurate (DOTL), or dibutyltin dilaurate (DBTL).
- tin catalyst such as dioctyltin dilaurate (DOTL), or dibutyltin dilaurate (DBTL).
- DTL dioctyltin dilaurate
- DBTL dibutyltin dilaurate
- the present invention relates to a method for preparing a composition comprising at least one NCO-terminated polyurethane, and at least one catalyst B chosen from tertiary amines, said process comprising the following steps:
- an NCO-terminated polyurethane comprising a step of polyaddition of a polyol composition (s) and a polyisocyanate composition (s), in the presence of at least one catalyst A selected from the group consisting of :
- organo-metallic catalysts with the exception of tin catalysts
- step b) adding at least one catalyst B selected from tertiary amines to the NCO-terminated polyurethane obtained after step a).
- the present invention relates to a process for the preparation of a composition comprising at least one NCO-terminated polyurethane, and at least one catalyst B chosen from tertiary amines, said process comprising the following steps:
- an NCO-terminated polyurethane comprising a step of polyaddition of a polyol composition (s) and a polyisocyanate composition (s), in the presence of at least one catalyst A selected from the group consisting of :
- organo-metallic catalysts with the exception of tin catalysts
- the NCO-terminated polyurethane may have a viscosity at 23 ° C. of less than or equal to 300,000 mPa.s, preferably less than or equal to 250,000 mPa.s, more preferably ranging from 100 mPa.s to 200,000 mPa.s. in particular from 4,000 mPa.s to 150,000 mPa.s, and preferably from 10,000 to 150,000 mPa.s.
- the viscosity can be measured using a Brookfield viscometer according to ISO 2555 (1999). Typically, the measurement carried out at 23 ° C can be done using a Brookfield RVT viscometer, a needle adapted to the viscosity range and a rotation speed of 20 rpm.
- the NCO-terminated polyurethane may have a number average molecular weight ranging from 1,000 g / mol to 50,000 g / mol, preferably from 1,000 g / mol to 30,000 g / mol, preferably from 5,000 g / mol to 20,000 g / mol, preferably 10,000 g / mol to 20,000 g / mol.
- the number-average molecular weight of the NCO-terminated polyurethanes can be measured by methods well known to those skilled in the art, for example by steric exclusion chromatography (or SEC) using polyethylene glycol type standards.
- the NCO-terminated polyurethane may have a polymolecularity number ranging from 1.5 to 3.5, preferably from 2.0 to 3.3.
- the polymolecularity index is defined as the ratio M w (weight average molecular weight) / M n (number average molecular weight) of the polyurethane.
- the above-mentioned polyol composition (s) may consist of a polyol or a mixture of polyols.
- the polyol (s) that can be used may be chosen from among those having a number-average molecular mass ranging from 200 g / mol to 20,000 g / mol, preferably from 400 g / mol to 18,000 g / mol.
- the number average molecular weight of the polyols can be calculated from the hydroxyl number (IOH) expressed in mg KOH / g and the functionality of the polyol or determined by methods well known to those skilled in the art, by example by steric exclusion chromatography (or SEC in English) with PEG (polyethylene glycol) standard.
- the polyols have a hydroxyl functionality ranging from 2 to 6.
- the hydroxyl functionality of a polyol is the average number of hydroxyl groups per mole of polyol.
- the polyol (s) that can be used can be chosen from polyester polyols, polyether polyols, polydiene polyols, polycarbonate polyols, polyether polycarbonate polyols, polyols. -OH terminated polymers, and mixtures thereof.
- the polyol (s) that can be used can be chosen from aromatic polyols, aliphatic polyols, carbonate polyols and mixtures of these compounds.
- the polyester polyol (s) may have a number-average molecular mass ranging from 1,000 g / mol to 10,000 g / mol, preferably from 2,000 g / mol to 6,000 g / mol. .
- polyester polyols mention may for example be made of:
- polyesters polyols of natural origin such as castor oil
- aliphatic polyols linear, branched or cyclic
- aromatic polyols such as, for example, ethanediol, 1,2-propanediol, 1,3-propanediol, glycerol, trimethylolpropane or 1,6-propanediol; hexanediol, 1,2,6-hexanetriol, butenediol, sucrose, glucose, sorbitol, pentaerythritol, mannitol, triethanolamine, N-methyldiethanolamine, and mixtures thereof, with
- polycarboxylic acid or its ester or anhydride derivative such as 1,6-hexanedioic acid, dodecanedioic acid, azelaic acid, sebacic acid, adipic acid, 1,18-acid; octadecanedioic acid, phthalic acid, succinic acid and mixtures of these acids, an unsaturated anhydride such as, for example, maleic or phthalic anhydride, or a lactone such as, for example, caprolactone.
- an unsaturated anhydride such as, for example, maleic or phthalic anhydride
- a lactone such as, for example, caprolactone.
- polyester polyols evoked can be prepared in a conventional manner, and are for the most part commercially available.
- polyester polyols there may be mentioned, for example, the following products of hydroxyl functionality equal to 2:
- the DYNACOLL ® 7381 (comercialisé by EVONIK) average molecular weight of about 3500 g / mol and having a melting point of 65 ° C,
- the DYNACOLL ® 7360 (commercially available from EVONIK) resulting from the condensation of adipic acid with hexanediol, and has an average molecular weight of about 3500 g / mol, and a melting point of 55 ° C about
- the DYNACOLL ® 7330 (commercially available from EVONIK) average molecular weight of about 3500 g / mol and having a melting point of 85 ° C
- DYNACOLL® 7250 polyester polyol having a viscosity of 180 Pa.s at 23 ° C., a number-average molecular weight Mn equal to 5,500 g / mol and a T g equal to -50 ° C. C
- KURARAY® P-6010 polyester polyol having a viscosity of 68 Pa.s at 23 ° C., a number-average molecular mass equal to 6,000 g / mol, and a T g equal to -64 ° C,
- polyester polyol having a viscosity of 687 Pa.s at 23 ° C, and a number average molecular weight of 10 000 g / mol.
- the polyester polyol is chosen from: a polycaprolactone; Castor oil ; a polyester polyol resulting from the condensation of ethylene glycol, propylene glycol, 1,3-propanediol and / or 1,6-hexanediol with adipic acid and / or the different isomers of phthalic acid; and their mixtures.
- the polyether polyol (s) may have a number-average molecular weight ranging from 200 to 20,000 g / mol, preferably from 400 to 12,000 g / mol.
- the polyether polyol (s) has (have) hydroxyl functionality ranging from
- the polyether polyol (s) usable according to the invention is (are) preferably chosen from polyoxyalkylene polyol, the linear or branched alkylene portion of which comprises from 1 to 4 carbon atoms. preferably 2 to 3 carbon atoms.
- the polyether polyol (s) usable according to the invention is (are) preferably chosen from polyoxyalkylene diols or polyoxyalkylene triols, and more preferably polyoxyalkylene diols, including the alkylene part, linear or branched, comprises 1 to 4 carbon atoms, preferably 2 to 3 carbon atoms.
- polyoxypropylene diol or triol also known as polypropylene glycols (PPG) diol or triol
- PPG polypropylene glycols
- polyoxyethylene diol or triol also referred to as polyethylene glycols (PEG) diol or triol
- PEG polyethylene glycols
- polyoxybutylene glycols also referred to as polybutylene glycols (PBG) diol or triol
- PBG polybutylene glycols
- copolymers or terpolymers of PPG / PEG / PBG diol or triol having a number-average molecular weight ranging from 400 g / mol to 18,000 g / mol and preferably ranging from 400 g / mol to 4000 g / mol,
- PolyTHF polytetrahydrofuran diol or triol having a number-average molecular weight ranging from 250 g / mol to 4000 g / mol,
- PTMG polytetramethylene glycols
- the polyether polyol (s) usable (s) is (are) chosen from polyoxypropylene diols or triols.
- the polyether polyols mentioned above can be prepared in a conventional manner, and are widely available commercially. They may for example be obtained by polymerization of the corresponding alkylene oxide in the presence of a catalyst based on a double metal-cyanide complex.
- polyether diols examples include polyoxypropylene diols marketed under the "Acclaim®” designation by Bayer, such as G “ACCLAIM ® 12200" of average molecular weight of 1 next 1335 g / mol , "ACCLAIM® 8200” with a number average molecular mass of 8,057 g / mol, and "ACCLAIM® 4200” with a number average molecular mass of close to 4,020 g / mol, or the marketed polyoxypropylene diol under the name "VORANOL P2000" by the company DOW of average molecular weight in the vicinity of 2 004 g / mol.
- polyether triols By way of examples of polyether triols, mention may be made of the polyoxypropylene triol marketed under the name "VORANOL CP3355" by the company DOW, with a number average molecular weight of close to 3554 g / mol.
- the polyol (s) polydiene (s) used (s) according to the invention can be chosen (s) preferably from polydienes containing terminal hydroxyl groups, and their corresponding hydrogenated or epoxidized derivatives.
- the polydiene (s) polyol (s) used (s) according to the invention is (are) chosen from polybutadienes having terminal hydroxyl groups, optionally hydrogenated or epoxidized.
- the polyol (s) polydiene (s) usable (s) according to the invention is (are) chosen from homopolymers and copolymers of butadiene having terminal hydroxyl groups, optionally hydrogenated or epoxidized.
- terminal hydroxyl groups of a polydiene polyol means the hydroxyl groups located at the ends of the main chain of the polydiene polyol.
- the hydrogenated derivatives mentioned above can be obtained by total or partial hydrogenation of the double bonds of a polydiene containing terminal hydroxyl groups, and are therefore saturated or unsaturated.
- the epoxidized derivatives mentioned above can be obtained by chemoselective epoxidation of the double bonds of the main chain of a polydiene containing terminal hydroxyl groups, and therefore comprise at least one epoxy group in its main chain.
- polybutadiene polyols mention may be made of saturated or unsaturated butadiene homopolymers, comprising terminal hydroxyl groups, optionally epoxidized, such as for example those marketed under the name POLY BD® or KRASOL® by the company CRAY VALLEY .
- the -OH terminated prepolymers can be obtained by polyaddition reaction between one or more polyol (s), and one or more polyisocyanate (s), in amounts of polyisocyanate (s) and polyol ( s) resulting in an NCO / OH molar ratio strictly less than 1.
- the reaction can be carried out in the presence of a catalyst, the catalyst being preferably a catalyst A according to the invention, namely chosen from the group consisting of organic catalysts. -metallics with the exception of tin catalysts, tertiary amines and mixtures thereof.
- the polyols and polyisocyanates that can be used can be those typically used for the preparation of -OH-terminated prepolymers, and preferably those described for the preparation of the NCO-terminated polyurethane according to the invention.
- CONVERGE POLYOL 212-10 and CONVERGE POLYOL 212-20 marketed by the company NOVOMER respectively having a number-average molecular weight (Mn) equal to 1000 and 2000 g / mol, the hydroxyl numbers of which are respectively 1 12 and 56 mg KOH / g, DESMOPHEN® C XP 2716 marketed by COVESTRO with a number-average molecular weight (Mn) equal to 326 g / mol, the hydroxyl number of which is 344 mg KOH / g, POLYOL C-590, C1090, C-2090 and C-3090 marketed by KURARAY having a number-average molecular weight (Mn) ranging from 500 to 3000 g / mol and a hydroxyl number ranging from 224 to 37 mg KOH / g.
- the polyol composition (s) consists of one or more polyols chosen from those mentioned above and their mixtures.
- the polyol (s) composition may consist of one or more polyols including at least one polyether polyol. More particularly, the polyol (s) composition may consist of one or more polyether polyols.
- polyisocyanate means a compound comprising at least two isocyanate groups (NCO).
- the above-mentioned polyisocyanate composition (s) may consist of a polyisocyanate or a mixture of polyisocyanates.
- the polyisocyanate (s) usable can be selected from those typically used in the synthesis of an NCO-terminated polyurethane.
- the polyisocyanate (s) usable can be aliphatic (linear or branched) or aromatic, and optionally substituted.
- the polyisocyanate (s) is (are) chosen from diisocyanates, triisocyanates, and mixtures thereof.
- the polyisocyanate (s) is (are) chosen from the group consisting of pentamethylene diisocyanate (PDI), hexamethylene diisocyanate (HDI), heptane diisocyanate, octane diisocyanate, nonane diisocyanate, decane diisocyanate, undecane diisocyanate, dodecane diisocyanate, methylene bis (4-cyclohexyl isocyanate) (HMDI), isophorone diisocyanate (I PDI), norbornane diisocyanate, norbornene diisocyanate, 1,4-cyclohexane diisocyanate (CHDI), methylcyclohexane diisocyanate, ethylcyclohexane diisocyanate, propylcyclohexane diisocyanate, methyldiethylcyclohexane diisocyanate, methyldiethylcycl
- the MDI can be in the form of an isomer or mixture of isomers, such as 4,4'-MDI and / or 2,4'-MDI.
- TDI can be in the form of an isomer or a mixture of isomers, such as 2,4-TDI and / or 2,6-TDI.
- the polyisocyanate is MDI, and in particular 4,4'-MDI.
- the polyisocyanate (s) used to prepare the polyurethane used according to the invention are typically widely available commercially.
- SCURANATE® TX sold by the company VENCOREX, corresponding to a 2,4-TDI of purity of the order of 95%
- SCURANATE® T100 sold by the company VENCOREX, corresponding to a 2,4-TDI of purity greater than 99% by weight
- DESMODUR® I sold by COVESTRO
- ISONATE® M125 marketed by DOW
- DOW corresponding to an MDI containing at least 97 % by weight of the 4,4'-MDI isomer.
- step a Process for the preparation of the NCO-terminated polyurethane (step a)
- the polyaddition step may be carried out at a temperature below 95 ° C, preferably from 65 ° C to 90 ° C, more preferably from 75 ° C to 85 ° C.
- the polyaddition step can be carried out under anhydrous conditions, for example under a nitrogen atmosphere.
- the polyaddition step may be carried out in amounts of polyisocyanate (s) and of polyol (s) such that the NCO / OH molar ratio is strictly greater than 1, for example between 1, 1 and 2.5, preferably between 1, 5 and 2.2, preferably between 1.60 and 2.0, for example between 1.60 and 1.90, advantageously between 1.60 and 1.85, in particular between 1.7 and 1.85 , so as to advantageously obtain an NCO-terminated polyurethane.
- polyisocyanate (s) and of polyol (s) such that the NCO / OH molar ratio is strictly greater than 1, for example between 1, 1 and 2.5, preferably between 1, 5 and 2.2, preferably between 1.60 and 2.0, for example between 1.60 and 1.90, advantageously between 1.60 and 1.85, in particular between 1.7 and 1.85 , so as to advantageously obtain an NCO-terminated polyurethane.
- the polyaddition step can also be carried out in amounts of polyisocyanate (s) and polyol (s) such that the NCO / OH molar ratio is strictly less than 1, to advantageously lead to an OH-terminated polyurethane.
- the NCO / OH molar ratio corresponds to the molar ratio of the number of isocyanate groups (NCO) to the number of hydroxyl groups (OH) carried respectively by the polyisocyanates and the polyols used.
- the process for preparing the NCO-terminated polyurethane comprises a step ii) subsequent to the aforementioned polyaddition step.
- the process for preparing said NCO-terminated polyurethane comprises:
- polystyrene resin styrene resin
- polystyrene resin styrene resin
- polyol styrene resin
- NCO / OH molar ratio strictly less than 1, preferably less than or equal to 0.9, preferably less than or equal to 0, 8, advantageously less than or equal to 0.7, in particular less than or equal to 0.6, to give an OH-terminated polyurethane
- step ii) a second polyaddition polyaddition step obtained in step i) with a polyisocyanate composition (s), in amounts of polyisocyanate (s) and OH-terminated polyurethane resulting in an NCO / OH molar ratio greater than 1 preferably greater than or equal to 1, 2, advantageously greater than or equal to 1, 5, in particular greater than or equal to 1.7.
- the above-mentioned steps i) and ii) are carried out under anhydrous conditions.
- the molar ratio NCO / OH is strictly greater than 1 in order to obtain an NCO-terminated polyurethane.
- the NCO-terminated polyurethane obtained at the end of step ii) no longer includes terminal OH functions.
- step ii) can be carried out in the presence of a catalyst, the catalyst being preferably catalyst A according to the invention.
- steps i) and ii) is carried out in the presence of tin or tin compounds, such as for example in the presence of tin catalysts.
- the aforementioned catalyst A is selected from the group consisting of:
- organometallic catalysts with the exception of tin catalysts; tertiary amines; and
- organometallic catalysts with the exception of tin catalysts means organometallic catalysts not comprising tin.
- It can be a mixture of catalysts of the same family (for example a mixture of several tertiary amines or a mixture of several organometallic compounds comprising different metal atoms), or a mixture of catalysts of the same family.
- different families for example a mixture of a tertiary amine and an organometallic compound.
- organometallic catalysts means catalysts comprising an organic radical and at least one metal.
- organic radical is understood to mean a radical comprising at least one carbon atom.
- Organometallic compounds may include organometallic compounds (compounds comprising at least one metal-carbon covalent bond), metal alkoxides, metal carboxylates, and metal coordination complexes with organic ligand (s) .
- organic ligand mention may be made of acetylacetonate.
- the metal atom of the organometallic compounds may be any metal atom known to those skilled in the art, with the exception of tin, and may in particular be chosen from aluminum, manganese, silver, nickel and copper, gold, platinum, palladium, ruthenium, rhodium, molybdenum, zinc, cobalt, iron, nickel, bismuth, titanium, or zirconium.
- the metal atom of the organometallic compounds is selected from aluminum, zinc, iron, bismuth, titanium, gold and zirconium.
- the organometallic catalysts may comprise several metal atoms, such as, for example, bismuth and zinc.
- the organometallic catalysts are catalysts based on bismuth and / or zinc.
- bismuth catalyst means a catalyst comprising bismuth. Such a catalyst may therefore comprise other metal atoms in addition to bismuth, such as for example zinc.
- the organometallic catalysts and in particular the bismuth-based catalysts, exclusively comprise bismuth as a metal atom (bismuth catalysts).
- Organometallic compounds (compounds comprising at least one metal-carbon covalent bond) may be carboxylates of organometallic compounds.
- the metal alkoxides may be selected from the group consisting of titanium tetrabutanolate, titanium tetraisopropoxide, zirconium tetrabutanolate, zirconium tetraisopropoxide, bismuth phenolate, and mixtures thereof.
- the metal carboxylates may be those in which the carboxylic acid contains from 2 to 20 carbon atoms, preferably from 4 to 14 carbon atoms.
- carboxylic acids that may be mentioned include butyric acid, isobutyric acid, caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, iso-stearic acid, abietic acid, neodecanoic acid, 2,2,3,5-tetramethylhexanoic acid, 2,4-dimethyl-2-isopropylpentanoic acid, 2,5-dimethyl-2-ethylhexanoic acid, 2-dimethyloctanoic acid, 2,2-diethylhexanoic acid, and arachidic acid.
- the metal carboxylates may be mono-carboxylates, dicarboxylates, tricarboxylates, or mixtures thereof.
- the metal carboxylates may be selected from the group consisting of zinc-based carboxylates, bismuth-based carboxylates, bismuth-based and zinc-based carboxylates, and mixtures thereof, the metal carboxylates being in particular selected from the group consisting of zinc carboxylates, bismuth carboxylates, bismuth and zinc carboxylates, and mixtures thereof.
- the bismuth carboxylates can be mentioned for example the Borchi KAT ® 320 (CAS Number: 67874-71-9, 2-ethyl hexanoate bismuth), the Borchi KAT ® 315 (CAS Number: 34364-26-6, neodecanoate bismuth) available from BORCHERS, KKAT XK-651 available from KING INDUSTRIES, KK KKAT XC-B221 available from KING INDUSTRIES, and COSCAT 83 (bismuth neodecanoate, neodecanoic acid) available from VERTELLUS.
- the Borchi KAT ® 320 CAS Number: 67874-71-9, 2-ethyl hexanoate bismuth
- the Borchi KAT ® 315 CAS Number: 34364-26-6, neodecanoate bismuth
- COSCAT 83 bismuth neodecanoate, neode
- BORCHI® KAT 0761 (CAS number: 27253-29-8, zinc neodecanoate) available from BORCHERS
- TIB KAT 616 zinc neodecanoate
- TIB KAT 244 bismuth and zinc 2-ethyl hexanoate
- Catalyst A is preferably chosen from metal carboxylates, and more particularly zinc-based carboxylates, bismuth-based carboxylates, bismuth and zinc-based carboxylates, and mixtures thereof.
- catalyst A is selected from bismuth 2-ethyl hexanoate, zinc 2-ethyl hexanoate, bismuth neodecanoate, zinc neodecanoate, zinc and bismuth 2-ethyl hexanoate, and mixtures thereof.
- Metal coordination complex with a (the) ligand (s) organic (s) may be selected from the group consisting of zinc acetylacetonate, titanium acetylacetonate (e.g. commercially available under the name TYZOR ® AA75 with of the company DORF ketal), titanium tetraacetylacetonate, aluminum trisacetylacetonate, aluminum chelates such as, for example, mono- acetylacetonate bis (ethylacetoacetate) (e.g.
- the tertiary amines are selected from the group consisting of triethylamine, tributylamine, N, N-dimethylcyclohexylamine, dimethylbenzylamine, N, N'-dimethylpiperazine, N, N, N, N- tetramethylpropane-1,3-diamine, bis (2-dimethylaminoethyl) ether, 2-dimethylaminoethyl-3-dimethylaminopropyl ether, N-methyl morpholine, N-ethyl morpholine, N-methoxyethyl morpholine, 2, 2'-dimorpholinodiethyl ether (DMDEE), bis (2,6-
- the tertiary amines are selected from 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), 1,5-diazabicyclo [4.3.0] non-5-ene (DBN), 2,2'-dimorpholinodiethyl ether (DMDEE), 1,4-diazabicyclo [2.2.2] octane (DABCO), and mixtures thereof, preferably Catalyst A is 1,4-diazabicyclo [2.2.2] octane ( DABCO) or 2,2'-dimorpholinodiethyl ether (DMDEE).
- DBU 1,8-diazabicyclo [5.4.0] undec-7-ene
- DBN 1,5-diazabicyclo [4.3.0] non-5-ene
- DMDEE 2,2'-dimorpholinodiethyl ether
- DABCO 1,4-diazabicyclo [2.2.2] octane
- DABCO
- catalyst A is not a tertiary amine salt.
- the catalyst A is chosen from organometallic catalysts, in particular from organometallic catalysts based on bismuth and / or zinc, such as, for example, zinc-based carboxylates, carboxylates based on bismuth, bismuth and zinc based carboxylates, or mixtures thereof, and advantageously from zinc carboxylates, bismuth carboxylates, bismuth and zinc carboxylates, and mixtures thereof.
- the total content of catalyst (s) A used in the polyaddition reaction is less than or equal to 250 ppm, advantageously less than or equal to 50 ppm, preferably less than or equal to 20 ppm, in particular less than or equal to at 5 ppm, for example less than or equal to 1 ppm, relative to the total weight of the reagents used in the polyaddition reaction.
- the catalyst A when the catalyst A is selected from tertiary amines, its total content is less than or equal to 100 ppm, preferably less than or equal to 50 ppm, for example less than or equal to 20 ppm, advantageously less than or equal to at 10 ppm, based on the total weight of the reagents used in the polyaddition reaction.
- ppm correspond to “parts per million”, and are mass ppm.
- no step in the process for preparing the NCO-terminated polyurethane uses tin or tin-based compounds, and in particular tin-based catalysts.
- the process according to the invention is carried out in the absence of tin or tin compounds, such as in the absence of tin catalyst.
- no step in the process for the preparation of the aforementioned composition comprises a step involving the use of tin or tin-based compounds, such as, for example, tin-based catalyst. .
- Step b) can be carried out at a temperature of less than or equal to 50 ° C, preferably 5 to 45 ° C, and more preferably 20 to 30 ° C.
- Step b) is preferably carried out under anhydrous conditions.
- the method according to the invention may comprise additional steps in steps a) and b).
- the method may comprise a step (s) of adding additional compounds, such as for example at least one filler or at least one additive.
- additional compounds may be added before step b) and / or simultaneously in step b), and / or after step b).
- the method may comprise a step c) of mixing the composition resulting from step b) or resulting from a possible step subsequent to step b).
- the method according to the invention is such that:
- catalyst A is chosen from organometallic catalysts with the exception of tin-based catalysts, preferably catalyst A is chosen from organometallic catalysts based on bismuth and / or zinc, such as, for example zinc carboxylates, bismuth carboxylates, bismuth and zinc carboxylates, and mixtures thereof; the crosslinking catalyst B chosen from 2,2'-morpholine diethyl ether (DMDEE), 1,4-diazabicyclo [2.2.2] octane (DABCO), and mixtures thereof.
- DMDEE 2,2'-morpholine diethyl ether
- DABCO 1,4-diazabicyclo [2.2.2] octane
- the method according to the invention is such that:
- Catalyst A is 1,4-diazabicyclo [2.2.2] octane (DABCO);
- the catalyst B selected from 2,2'-morpholine diethyl ether (DMDEE), 1,4-diazabicyclo [2.2.2] octane (DABCO), and mixtures thereof,
- the content of catalyst A being preferably less than 400 ppm, in particular less than or equal to 100 ppm, preferably less than or equal to 50 ppm, for example less than or equal to 20 ppm, advantageously less than or equal to 10 ppm by weight total reagents used in the polyaddition reaction.
- the present invention also relates to a composition
- a composition comprising:
- At least one NCO-terminated polyurethane obtained by a process comprising at least one step of polyaddition of a polyol composition (s) and a polyisocyanate composition (s), in the presence of at least one catalyst A selected in the group consisting of:
- organo-metallic catalysts with the exception of tin catalysts
- catalyst A when catalyst A is chosen from tertiary amines, its total content is less than 400 ppm, preferably less than or equal to 100 ppm, preferably less than or equal to 50 ppm, for example less than or equal to 20 ppm, advantageously less than or equal to 10 ppm, relative to the total weight of the reagents used in the polyaddition reaction.
- Catalyst B is a crosslinking catalyst. It makes it possible in particular to catalyze the crosslinking of the NCO-terminated polyurethane in the presence of water or moisture.
- Water or moisture can be provided by the surface of the support or the surrounding environment, naturally (atmospheric humidity) or controlled (for example, in a thermostatically controlled chamber at a relative humidity between 40% and 70% (preferably at a humidity of approximately 50%) at 23 ° C, or in an oven up to 150 ° C) in contact with the composition according to the invention.
- This crosslinking is reflected in particular by the creation, between the polyurethane polymer chains, of urea type bonds which lead to the formation of a three-dimensional polymeric network.
- Catalyst B may be selected from the group consisting of triethylamine, tributylamine, N, N-dimethylcyclohexylamine, dimethylbenzylamine, N, N'-dimethylpiperazine, N, N, N, N-tetramethylpropane.
- 1,3-diamine bis (2-dimethylaminoethyl) ether, 2-dimethylaminoethyl-3-dimethylaminopropyl ether, N-methyl morpholine, N-ethyl morpholine, N-methoxyethyl morpholine, 2,2 ' dimorpholinodiethyl ether (DMDEE), bis (2,6-dimethylmorpholinoethyl) ether, bis (3,5-dimethylmorpholinoethyl) ether, N, N-dimethylphenylamine, N, N, N, N-tetramethylbutane 1,3-diamine, N, N, N, N-tetramethylpropane-1,3-diamine, N, N, N, N-tetramethylhexane-1,6-diamine, 1-methyl imidazole, 2-methyl-1-vinylimidazole, 1-allylimidazole, 1-phenylimidazole
- the catalyst B is selected from the group consisting of triethylamine, tributylamine, N, N-dimethylcyclohexylamine, dimethylbenzylamine, N, N'-dimethylpiperazine, N, N, N N-tetramethylpropane-1,3-diamine, 2-dimethylaminoethyl-3-dimethylaminopropyl ether, N-methyl morpholine, N-ethyl morpholine, N-methoxyethyl morpholine, 2,2'-dimorpholinodiethyl ether (DMDEE), bis (2,6-dimethylmorpholinoethyl) ether, bis (3,5-dimethylmorpholinoethyl) ether, N, N-dimethylphenylamine, N, N, N, N-tetramethylbutane-1, 3-diamine, N, N, N, N, N-tetramethylpropane-1,3-
- Catalyst B is preferably selected from the group consisting of N-methyl morpholine, N-ethyl morpholine, N-methoxyethyl morpholine, 2,2'-dimorpholinodiethyl ether (DMDEE), bis (2 , 6-dimethylmorpholinoethyl) ether, bis (3,5-dimethylmorpholinoethyl) ether, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU), 1,4-diazabicyclo [2.2.2] octane (DABCO), 1,5-diazabicyclo [4.3.0] non-5-ene (DBN), and mixtures thereof.
- DMDEE 2,2'-dimorpholinodiethyl ether
- DBU 1,8-diazabicyclo [5.4.0] -7-undecene
- DBU 1,4-diazabicyclo [2.2.2] octane
- catalyst B is selected from 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), 1,5-diazabicyclo [4.3.0] non-5-ene (DBN ), 2,2'-morpholine diethyl ether (DMDEE), 1,4-diazabicyclo [2.2.2] octane (DABCO), and mixtures thereof.
- DBU 1,8-diazabicyclo [5.4.0] undec-7-ene
- DBN 1,5-diazabicyclo [4.3.0] non-5-ene
- DMDEE 2,2'-morpholine diethyl ether
- DABCO 1,4-diazabicyclo [2.2.2] octane
- CMR carcinogenic, mutagenic and reprotoxic
- the catalyst B is selected from diethyl ether-2,2'-morpholine (DMDEE), 1,4-diazabicyclo [2.2.2] octane (DABCO), and mixtures thereof.
- DMDEE diethyl ether-2,2'-morpholine
- DABCO 1,4-diazabicyclo [2.2.2] octane
- the catalyst B may be chosen from DMDEE / DABCO mixtures having a mass ratio ranging from 100/0 to 0/100, preferably from 30/70 to 70/30, and advantageously from 40/60 to 60/40, in particular the ratio being 50/50.
- the total content of catalyst B in the composition may be less than or equal to 1%, preferably less than or equal to 0.8%, preferentially less than or equal to 0.5%, advantageously less than or equal to 0.3%, by example less than or equal to 0.2% by weight relative to the total weight of said composition.
- the total content of catalyst B in the composition may range from 0.001% to 1%, preferably from 0.01% to 0.8%, advantageously from 0.1% to 0.5% by weight relative to the total weight of said composition.
- the total content of catalyst B in the composition may be chosen from one of the following contents: 0.001%, 0.01%, 0.02%, 0.03%, 0.04%, 0.05%, 0, 06%, 0.07%, 0.08%, 0.09%, 0.1%, 0.2%, 0.3%, 0.4%, 0.5%, 0.6%, 0, 7%, 0.8%, 0.9%, or 1% by weight relative to the total weight of said composition, the total content of catalyst B being preferably 0.2% by weight relative to the total weight of said composition.
- the composition may comprise a filler.
- the filler may be chosen from organic fillers, inorganic fillers and mixtures thereof.
- organic filler (s) any organic filler (s) and especially polymeric filler (s) typically used in the field of mastic compositions can be used.
- PVC polyvinyl chloride
- EVA ethylene vinyl acetate
- aramid fibers such as KEVLAR®
- Expandable or unexpandable thermoplastic polymer hollow microspheres can also be used. There may be mentioned hollow microspheres vinylidene chloride / acrylonitrile.
- the average particle size of the filler (s) that can be used is preferably less than or equal to 10 microns, more preferably less than or equal to 3 microns, in order to prevent their sedimentation in the composition according to the invention. during its storage.
- the average particle size is measured for a volume particle size distribution and corresponding to 50% by volume of the analyzed particle sample.
- the average particle size corresponds to the median diameter (D50 or Dv50) which corresponds to the diameter such that 50% of the particles in volume have a size less than said diameter.
- D50 or Dv50 the median diameter
- this value is expressed in micrometers and determined according to the NF ISO 13320-1 (1999) standard by laser diffraction on a MALVERN type apparatus.
- the filler is an inorganic filler.
- mineral filler As examples of mineral filler (s), it is possible to use any mineral filler (s) typically used in the field of surface coating compositions, glues or putty.
- the inorganic fillers may be in the form of particles of various geometry. They may for example be spherical, fibrous, or have an irregular shape.
- the filler is selected from sand, glass beads, glass, quartz, barite, alumina, mica, talc, carbonates, and mixtures thereof.
- the sand which can be used in the present invention preferably has a particle size ranging from 0.1 to 400 ⁇ m, preferably from 1 to 400 ⁇ m, more preferably from 10 to 350 ⁇ m, more preferably from 50 to 300 ⁇ m.
- the glass beads which can be used in the present invention preferably have a particle size ranging from 0.1 to 400 ⁇ m, preferably from 1 to 400 ⁇ m, more preferably from 10 to 350 ⁇ m, more preferably from 50 to 300 ⁇ m.
- the filler is a carbonate filler selected from alkali metal or alkaline earth carbonates, such as, for example, calcium carbonate.
- the fillers may be natural or treated, for example using an organic acid such as stearic acid, or a mixture of organic acids consisting predominantly of stearic acid.
- the total amount of filler may vary from 0.01% to 70% by weight, preferably from 20% to 65%, preferably from 20% to 50%, advantageously from 25% to 40% by weight relative to the total weight of the composition.
- the composition may comprise at least one additive, for example chosen from the group consisting of plasticizers, solvents, pigments, dyes, adhesion promoters, moisture absorbers, UV stabilizers, tackifying resins, solvents antioxidants, flakes, fluorescent materials, rheological additives, fillers, flame retardants, waxes, and mixtures thereof.
- additives for example chosen from the group consisting of plasticizers, solvents, pigments, dyes, adhesion promoters, moisture absorbers, UV stabilizers, tackifying resins, solvents antioxidants, flakes, fluorescent materials, rheological additives, fillers, flame retardants, waxes, and mixtures thereof.
- the aforementioned composition may comprise at least one plasticizing agent in a proportion of 5% to 30% by weight, preferably 10% to 30% by weight, preferably 15% to 25% by weight relative to the total weight of said composition.
- phthalates benzoates
- esters trimethylolpropane esters trimethylolethane esters
- trimethylolmethane esters trimethylolmethane esters
- glycerol esters pentaerythritol esters
- naphthenic mineral oils naphthenic mineral oils
- Phthalates that may be mentioned include, for example, diisononyl phthalate, di-isobutyl phthalate, dioctyl phthalate, dicyclohexyl phthalate, diisooctyl phthalate, diisododecyl phthalate, dibenzyl phthalate and diisodecyl phthalate (for example marketed by BASF under the name denomination PALATINOL TM DIDP), or butylbenzyl phthalate.
- benzoates mention may be made, for example, of neopentylglycol dibenzoate (for example available under the name UNIPLEX® 512 from LANXESS), dipropyleneglycol dibenzoate (for example available under the name BENZOFLEX® 9-88SG from EASTMAN), a mixture of diethylene glycol dibenzoate and dipropylene glycol dibenzoate (for example available under the name K-Flex® 850 S from KALAMA CHEMICAL), or a mixture of diethylene glycol dibenzoate, dipropylene glycol dibenzoate and triethylene glycol dibenzoate (for example, available under the name BENZOFLEX® 2088 from Eastman).
- neopentylglycol dibenzoate for example available under the name UNIPLEX® 512 from LANXESS
- dipropyleneglycol dibenzoate for example available under the name BENZOFLEX® 9-88SG from EASTMAN
- pentaerythritol esters mention may for example be made of pentaerythritol tetravalerate (for example available under the name PEVALEN TM from the company PERSTORP).
- cyclohexanedicarboxylates mention may be made, for example, of diisononyl-1,2-cyclohexanedicarboxylate (for example available under the name HEXAMOLL DINCH® from BASF).
- composition according to the invention may comprise at least one rheological agent.
- a reagent (s) of rheology that may be used, there may be mentioned any rheology agent usually used in the field of adhesive compositions, putty and / or surface coating.
- one or more rheology agents chosen from thixotropic agents, and more preferably from:
- PVC plastisols corresponding to a suspension of PVC in a plasticizer miscible with PVC, obtained in situ by heating at temperatures ranging from 60 ° C to 80 ° C.
- These plastisols can be those described in particular in the book "Polyurethane Sealants", Robert M. Evans, ISBN 087762-998-6, fumed silica,
- urea derivatives resulting from the reaction of an aromatic diisocyanate monomer such as 4,4'-MDI with an aliphatic amine such as butylamine.
- aromatic diisocyanate monomer such as 4,4'-MDI
- aliphatic amine such as butylamine
- - micronized amide waxes such as CRAYVALLAC ® SL, CRAYVALLAC ® SLX, CRAYVALLAC ® SLT marketed by ARKEMA.
- the total content of rheology agent (s) that may be used may vary from 1% to 40% by weight, preferably from 5% to 30% by weight, more preferably from 10% to 25% by weight relative to to the total weight of the composition.
- the solvent is preferably a volatile solvent at 23 ° C.
- the volatile solvent may for example be chosen from volatile alcohols at 23 ° C., such as ethanol or isopropanol.
- the volatile solvent makes it possible, for example, to reduce the viscosity of the composition and to make the composition easier to apply.
- the volatile nature of the solvent allows in particular the seal, obtained after curing of the composition, to no longer contain solvent. Thus, the solvent has, for example, no negative influence on the hardness of the joint.
- a solvent in particular a volatile solvent
- its content is preferably less than or equal to 5% by weight, more preferably less than or equal to 3% by weight, relative to the total weight of the composition.
- the content of solvent (s) in the composition is between 0% and 5% by weight.
- a pigment When a pigment is present in the composition, its content is preferably less than or equal to 3% by weight, more preferably less than or equal to 2% by weight, relative to the total weight of the composition. When present, the pigment may for example represent from 0.1% to 3% by weight or from 0.4% to 2% by weight of the total weight of the composition.
- the pigments can be organic or inorganic pigments.
- the pigment is T1O2, in particular KRONOS® 2059 sold by the company KRONOS.
- the moisture absorber may for example be chosen from hydrolysable, non-polymeric alkoxysilane derivatives having a molecular mass of less than 500 g / mol, preferably chosen from trimethoxysilane and triethoxysilane derivatives. Such an agent can typically extend the shelf life of the composition during storage and transportation prior to use.
- gamma-metacryloxypropyltrimethoxysilane for example available under the trade name SILQUEST® A-174 from the company MOMENTIVE
- methacryloxymethyltrimethoxysilane for example available under the name GENIOSIL® XL33 from WACKER
- vinyltrimethoxysilane isooctyltrimethoxysilane, or phenyltrimethoxysilane.
- a moisture absorber When a moisture absorber is present in the composition, its content is preferably less than or equal to 3% by weight, more preferably less than or equal to 2% by weight relative to the total weight of the composition. When present, the moisture absorber may for example represent from 0.5% to 3% by weight or from 1% to 2% by weight relative to the total weight of the composition.
- the composition may comprise from 0.1% to 3%, preferably from 1% to 3% by weight, of at least one UV stabilizer or antioxidant.
- These compounds are typically introduced to protect the composition from degradation resulting from a reaction with oxygen that is likely to be formed by the action of heat or light.
- These compounds may include primary antioxidants that trap free radicals. Primary antioxidants can be used alone or in combination with other secondary antioxidants or UV stabilizers.
- IRGANOX® 1010 examples include IRGANOX® 1010, IRGANOX® B561, IRGANOX® 245, IRGAFOS® 168, TINUVIN® 328 or TINUVIN TM 770 marketed by BASF.
- the composition may comprise at least one tackifying resin, particularly when the composition is an adhesive composition.
- resin (s) tackifier (s) usable (s) there may be mentioned any tackifying resin usually used in the field of adhesive compositions.
- rosins such as, for example, rosin extracted from pine gum, wood rosin extracted from tree roots
- modified rosins such as, for example, rosin extracted from pine gum, wood rosin extracted from tree roots
- their hydrogenated, dimerized, polymerised or esterified derivatives by monoalcohols or polyols such as glycerol or pentaerythritol
- acrylic resins having in particular a viscosity at 100 ° C. of less than 100 Pa.s;
- copolymers based on natural terpenes such as, for example, styrene / terpene, alpha-methyl styrene / terpene and vinyl toluene / terpene; and
- Such resins are commercially available, and among those of type (i), (ii), (iii) or (iv), there may be mentioned, for example, the following products:
- NORSOLENE® W100 available from the company CRAY VALLEY, obtained by polymerization of alpha-methyl styrene without the action of phenols, having a number-average molecular weight of 900 Da; SYLVAREZ® 510 which is available from the company KRATON having a number average molecular weight of about 1740 Da, the method of obtaining comprises the addition of phenols;
- SYLVALITE® RE 100 which is a rosin pentaerythritol ester available from KRATON, and whose number-average molecular weight is approximately 1700 Da.
- the tackifying resin preferably has a number-average molecular weight ranging from 100 to 6000 g / mol, preferably from 300 to 4000 g / mol, preferably from 500 to 2000 g / mol.
- the number average molecular weights of the tackifying resins can be measured according to methods well known to those skilled in the art, for example by steric exclusion chromatography using a polystyrene type standard.
- the composition may comprise from 5% to 20%, preferably from 5% to 10% by weight of at least one tackifying resin, relative to the total weight of said composition.
- the composition may be an adhesive composition, putty and / or surface coating, especially for the field of construction.
- the composition is devoid of tin or tin-based compounds, in particular tin-based catalysts.
- the total content of catalyst A in the composition may be less than or equal to 1000 ppm, preferably less than or equal to 250 ppm, advantageously less than or equal to 50 ppm, preferably less than or equal to 20 ppm, in particular less than or equal to 5 ppm. , for example less than or equal to 1 ppm, relative to the total weight of the composition.
- the catalyst A when the catalyst A is chosen from tertiary amines, its total content is less than 400 ppm, preferably less than or equal to 100 ppm, preferably less than or equal to 50 ppm, for example less than or equal to 20 ppm. ppm, advantageously less than or equal to 10 ppm, relative to the total weight of the composition.
- the composition does not comprise any catalyst other than the catalysts A and B mentioned above.
- catalyst A is selected from tertiary amines, its nature is different from catalyst B.
- Catalyst A is preferably different from catalyst B.
- the present invention relates to a composition
- a composition comprising:
- At least one NCO-terminated polyurethane obtained by a process comprising at least one step of polyaddition of a polyol composition (s) and a polyisocyanate composition (s), in the presence of at least one catalyst A chosen from organometallic catalysts based on bismuth and / or zinc, such as, for example, bismuth carboxylates, zinc carboxylates, bismuth and zinc carboxylates, and mixtures thereof, and preferably bismuth carboxylates, optionally at least one charge ; and at least one catalyst B selected from tertiary amines, such as, for example, selected from 2,2'-diethyl-2,2'-morpholine ether (DMDEE), 1,4-diazabicyclo [2.2.2] octane (DABCO), and their mixtures.
- a catalyst A chosen from organometallic catalysts based on bismuth and / or zinc, such as, for example, bismuth carboxylates, zinc carboxylate
- the present invention relates to a composition
- a composition comprising:
- At least one NCO-terminated polyurethane obtained by a process comprising at least one step of polyaddition of a polyol composition (s) and a polyisocyanate composition (s), in the presence of at least one catalyst A chosen from tertiary amines, catalyst A being in particular 1,4-diazabicyclo [2.2.2] octane (DABCO);
- At least one catalyst B selected from tertiary amines such as, for example, selected from 2,2'-diethyl-2,2'-morpholine ether (DMDEE), 1,4-diazabicyclo [2.2.2] octane (DABCO), and their mixtures,
- catalyst A being less than 400 ppm, preferably less than or equal to 100 ppm, preferably less than or equal to 50 ppm, for example less than or equal to 20 ppm, advantageously less than or equal to 10 ppm.
- the composition comprises:
- the percentages by weight being expressed relative to the total weight of the composition.
- the composition comprises:
- ком ⁇ онентs from 0% to 40% by weight, preferably from 1% to 40% by weight, preferably from 5% to 30% by weight of at least one additive selected from the group consisting of plasticizers, solvents, pigments, dyes, adhesion promoters, moisture absorbers, UV stabilizers, tackifying resins, solvents, antioxidants, flakes, fluorescent materials, rheological additives, fillers, flame retardants, waxes, and mixtures thereof,
- the percentages by weight being expressed relative to the total weight of the composition.
- composition is preferably stored in an anhydrous environment, for example in a sealed package where the composition is protected from moisture and preferably protected from light.
- the composition is an adhesive, putty, and / or surface coating composition.
- the composition is a putty composition.
- compositions according to the invention are advantageously less toxic and less dangerous for humans and the environment than the existing compositions.
- compositions according to the invention advantageously have a spectrum of varied properties, which allows their use in various applications as an adhesive, surface coating or putty, such as for example in the field of construction or transport.
- compositions according to the invention are advantageously stable in terms of viscosity over long storage periods, and are in fact easy to implement.
- the adhesive, mastic and / or surface coating compositions according to the invention advantageously have good properties of extrusion or coating at ambient temperature through mixing devices and / or application of coatings, adhesive compositions or sealants. .
- compositions according to the invention are advantageously putty compositions having in particular a good compromise between storage stability in terms of viscosity, and mechanical properties and / or adhesion.
- the present invention also relates to the use of a composition as defined above, as an adhesive, putty or surface coating, preferably as putty, for example as a construction mastic.
- the composition can in particular be used to make seals and expansion in buildings, especially between concrete / concrete substrates.
- composition according to the invention may be in single-component form, that is to say that all the components are packaged in the same compartment.
- the composition is preferably ready for use, that is to say that the user (individual or professional) can directly apply the composition to achieve the seal, without having to perform prior mixing.
- between x and y means an interval in which the terminals x and y are included.
- the range “between 10% and 60%” includes the values 10% and 60%.
- DIDP (marketed by BASF): diisodecylphthalate (plasticizer);
- T1O2 (marketed by CRISTAL): titanium dioxide (pigment);
- Ca (OH) 2 (marketed by OMYA): calcium hydroxide ("CO2 scavenger”);
- CaCC 3 (marketed by OMYA) is a calcium carbonate (filler);
- PTSI (marketed by BORCHERS): p-Toluenesulfonyl Isocyanate (Case Number: 4083-64-1) ("H2O scavenger");
- PVC polyvinyl chloride powder (organic load); ISONATE® M125 (marketed by the company DOW): mixture of isomers of MDI containing at least 97% of the 4,4'-MDI isomer (4,4'-diphenylmethylene diisocyanate) having a weight percentage of NCO of 33.6%;
- VORANOL® P2000 polyoxypropylene diol with a number-average molecular weight (Mn) of about 2000 g / mol having a hydroxyl number of about 56 mg KOH / g;
- BORCHI® KAT 315 (marketed by BORCHERS): bismuth neodecanoate (CAS number: 34364-26-6);
- AMICURE ® TEDA (marketed by EVONIK): DAB CO: 1,4-diazabicyclo [2.2.2] octane (CAS number: 280-57-9); JEFFCAT® DMDEE (marketed by HUNTSMAN): 2,2'-dimorpholinodiethylether (CAS number: 6425-39-4).
- a solution A of 17.17% w / w of n-butylamine in 82.83% w / w of DIDP is first prepared, and a solution B of 29.46% w / w of 4,4'- MDI in 70.34% w / w of DIDP.
- the reaction is immediate and the reactor temperature reaches 140 ° C. at the end of manufacture.
- the Brookfield viscosity of the suspension D measured at 23 ° C. is 15 Pa.s.
- ISONATE ® M125 is introduced and the mixture is heated to 40 ° C. Then, a polyoxypropylene triol (having an IOH of 44.5 ⁇ 1.5 mg KOH / g, and a number average molecular weight of about 3780 ⁇ 100 g / mol), Voranol P200, and the solvent ( xylene). The mixture is then heated to 50 ° C with stirring. Then, the catalyst is added. The mixture is then heated with stirring to 85 ° C and maintained at this temperature for 2 hours.
- a polyoxypropylene triol having an IOH of 44.5 ⁇ 1.5 mg KOH / g, and a number average molecular weight of about 3780 ⁇ 100 g / mol
- Voranol P200 Voranol P200
- the solvent xylene
- the mastic compositions were obtained according to the following method:
- composition D (example 1), then dehydrating agent and other additives;
- Mastic compositions C1 to C4 were extruded through an extrusion nozzle 4 mm in diameter at a pressure of 3 bar at constant temperature and hygrometry to evaluate their viscosity.
- the viscosity measurement (in millipascal seconds (mPa.s)) was carried out at 23 ° C. at t0 and t + 3 weeks using a Brookfield RVT viscometer, with a number 5 needle at a rotation speed of 20 revolutions per minute (rpm).
- the extrusion corresponds to the amount in gram of mastic which could be extruded per minute at a piston pressure of 3 bar at 23 ° C.
- the principle of measurement is to stretch in a tensile machine, whose moving jaw moves at a constant speed equal to 100 mm / minute, a standard specimen consisting of the crosslinked composition and to record, at the moment when the rupture occurs of the specimen, the tensile stress applied (in MPa) and the elongation of the specimen (in%).
- the standard test piece is dumbbell-shaped, as shown in the international standard ISO 37 of 2011. The narrow part of the dumbbell used has a length of 20 mm, a width of 4 mm and a thickness of 500 mp ⁇ . 100% elongation module
- the 100% elongation module was measured according to the test in ISO 37 of 201 1.
- the maximum elongation modulus at break is measured according to ISO 37 of 2011.
- compositions having various properties are advantageously obtained, without having to modify the nature of the other ingredients of the compositions.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Polyurethanes Or Polyureas (AREA)
- Sealing Material Composition (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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FR1762601A FR3075213B1 (fr) | 2017-12-20 | 2017-12-20 | Procede de preparation d'une composition comprenant un polyurethane a terminaisons nco |
PCT/FR2018/053398 WO2019122706A1 (fr) | 2017-12-20 | 2018-12-19 | Procede de preparation d'une composition comprenant un polyurethane a terminaisons nco |
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EP3728386A1 true EP3728386A1 (fr) | 2020-10-28 |
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EP18847140.3A Pending EP3728386A1 (fr) | 2017-12-20 | 2018-12-19 | Procede de preparation d'une composition comprenant un polyurethane a terminaisons nco |
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US (1) | US11845830B2 (fr) |
EP (1) | EP3728386A1 (fr) |
JP (1) | JP2021507964A (fr) |
CN (1) | CN111757901A (fr) |
FR (1) | FR3075213B1 (fr) |
WO (1) | WO2019122706A1 (fr) |
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FR3140086A1 (fr) * | 2022-09-28 | 2024-03-29 | Bostik Sa | Polyuréthane(s) ionique(s) éventuellement silylé(s) |
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US3547848A (en) | 1967-11-03 | 1970-12-15 | Armour Ind Chem Co | Thixotropic coating compositions comprising a varnish and a di-substituted urea |
DE19529406A1 (de) * | 1995-08-10 | 1997-02-13 | Henkel Kgaa | Polyurethan-Prepolymer mit NCO-Gruppen |
US6362300B1 (en) * | 2000-07-06 | 2002-03-26 | The Yokohama Rubber Co., Ltd. | Moisture-curable polyurethane compositions |
EP1408062A1 (fr) * | 2002-10-08 | 2004-04-14 | Sika Technology AG | Composition de polyuréthane comprenant un catalyseur à base de Bismuth |
JP2005272525A (ja) * | 2004-03-23 | 2005-10-06 | Tosoh Corp | ポリウレタン樹脂製造用触媒組成物及びポリウレタン樹脂の製造方法 |
DE102006020605A1 (de) * | 2006-05-02 | 2007-11-08 | Bayer Materialscience Ag | Feuchtigkeitshärtende Kleb- und Dichtstoffe |
US9309439B2 (en) * | 2010-07-22 | 2016-04-12 | Construction Research & Technology Gmbh | Sealant and adhesive using green prepolymer |
JP5566360B2 (ja) * | 2010-11-22 | 2014-08-06 | ローム アンド ハース カンパニー | ビス(イソシアナトメチル)シクロヘキサンからのイソシアヌラート組成物および第三級アミン触媒を含むポリウレタンコーティング組成物 |
US9556303B2 (en) * | 2011-02-21 | 2017-01-31 | Honeywell International Inc. | Catalysts for polyurethane foam polyol premixes containing halogenated olefin blowing agents |
FR3015510B1 (fr) * | 2013-12-19 | 2017-05-12 | Bostik Sa | Composition adhesive reticulable a l'humidite et a la chaleur a base de polyurethane et comprenant une faible teneur en monomere isocyanate |
FR3018816B1 (fr) * | 2014-03-19 | 2017-07-28 | Bostik Sa | Prepolymere de polyurethane a terminaisons cyclocarbonate de faible viscosite et son utilisation dans la fabrication d'une composition adhesive multicomposant |
FR3045616B1 (fr) | 2015-12-21 | 2020-07-10 | Bostik Sa | Mastics polyurethane superelastiques |
-
2017
- 2017-12-20 FR FR1762601A patent/FR3075213B1/fr active Active
-
2018
- 2018-12-19 JP JP2020533624A patent/JP2021507964A/ja active Pending
- 2018-12-19 US US16/768,105 patent/US11845830B2/en active Active
- 2018-12-19 CN CN201880082652.0A patent/CN111757901A/zh active Pending
- 2018-12-19 EP EP18847140.3A patent/EP3728386A1/fr active Pending
- 2018-12-19 WO PCT/FR2018/053398 patent/WO2019122706A1/fr unknown
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CN111757901A (zh) | 2020-10-09 |
FR3075213A1 (fr) | 2019-06-21 |
JP2021507964A (ja) | 2021-02-25 |
WO2019122706A1 (fr) | 2019-06-27 |
US20200308337A1 (en) | 2020-10-01 |
US11845830B2 (en) | 2023-12-19 |
FR3075213B1 (fr) | 2020-08-28 |
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