CH672750A5 - - Google Patents
Download PDFInfo
- Publication number
- CH672750A5 CH672750A5 CH1178/87A CH117887A CH672750A5 CH 672750 A5 CH672750 A5 CH 672750A5 CH 1178/87 A CH1178/87 A CH 1178/87A CH 117887 A CH117887 A CH 117887A CH 672750 A5 CH672750 A5 CH 672750A5
- Authority
- CH
- Switzerland
- Prior art keywords
- catalyst
- reaction mixture
- tin
- mixture according
- curing
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 claims description 142
- 239000000203 mixture Substances 0.000 claims description 95
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 67
- -1 hydroxyl compound Chemical class 0.000 claims description 57
- 150000001412 amines Chemical class 0.000 claims description 54
- 239000012974 tin catalyst Substances 0.000 claims description 46
- 239000011541 reaction mixture Substances 0.000 claims description 44
- 229920005862 polyol Polymers 0.000 claims description 36
- 239000012190 activator Substances 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 29
- 150000003077 polyols Chemical class 0.000 claims description 29
- 229910052797 bismuth Inorganic materials 0.000 claims description 24
- 239000005056 polyisocyanate Substances 0.000 claims description 22
- 229920001228 polyisocyanate Polymers 0.000 claims description 22
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 20
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 18
- 238000006555 catalytic reaction Methods 0.000 claims description 18
- 229960002887 deanol Drugs 0.000 claims description 18
- 239000012972 dimethylethanolamine Substances 0.000 claims description 18
- 239000012948 isocyanate Substances 0.000 claims description 18
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 16
- 239000000758 substrate Substances 0.000 claims description 14
- 150000003512 tertiary amines Chemical class 0.000 claims description 13
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 13
- 235000013824 polyphenols Nutrition 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 10
- 239000008139 complexing agent Substances 0.000 claims description 10
- 150000008442 polyphenolic compounds Chemical class 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 9
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 9
- 150000002576 ketones Chemical class 0.000 claims description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 9
- LPYUENQFPVNPHY-UHFFFAOYSA-N 3-methoxycatechol Chemical compound COC1=CC=CC(O)=C1O LPYUENQFPVNPHY-UHFFFAOYSA-N 0.000 claims description 8
- 239000002738 chelating agent Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 8
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 8
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 7
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 claims description 6
- NIAAGQAEVGMHPM-UHFFFAOYSA-N 4-methylbenzene-1,2-dithiol Chemical compound CC1=CC=C(S)C(S)=C1 NIAAGQAEVGMHPM-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- ULIKDJVNUXNQHS-UHFFFAOYSA-N 2-Propene-1-thiol Chemical compound SCC=C ULIKDJVNUXNQHS-UHFFFAOYSA-N 0.000 claims description 4
- SUNXFMPZAFGPFW-UHFFFAOYSA-N 2-methyl-5-(1-sulfanylpropan-2-yl)cyclohexane-1-thiol Chemical compound SCC(C)C1CCC(C)C(S)C1 SUNXFMPZAFGPFW-UHFFFAOYSA-N 0.000 claims description 4
- DKIDEFUBRARXTE-UHFFFAOYSA-M 3-mercaptopropionate Chemical compound [O-]C(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-M 0.000 claims description 4
- HOASVNMVYBSLSU-UHFFFAOYSA-N 6-ethoxy-3h-1,3-benzothiazole-2-thione Chemical compound CCOC1=CC=C2N=C(S)SC2=C1 HOASVNMVYBSLSU-UHFFFAOYSA-N 0.000 claims description 4
- SMTOKHQOVJRXLK-UHFFFAOYSA-N butane-1,4-dithiol Chemical compound SCCCCS SMTOKHQOVJRXLK-UHFFFAOYSA-N 0.000 claims description 4
- FKDXNKLATUKJAL-UHFFFAOYSA-N dodecane-1,1-dithiol Chemical compound CCCCCCCCCCCC(S)S FKDXNKLATUKJAL-UHFFFAOYSA-N 0.000 claims description 4
- MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 claims description 4
- 229940079877 pyrogallol Drugs 0.000 claims description 4
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 claims description 4
- 229940103494 thiosalicylic acid Drugs 0.000 claims description 4
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 claims description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
- IGOGJHYWSOZGAE-UHFFFAOYSA-N 2,3,5,6-tetrafluorobenzenethiol Chemical compound FC1=CC(F)=C(F)C(S)=C1F IGOGJHYWSOZGAE-UHFFFAOYSA-N 0.000 claims description 3
- JFISFZKKYWLPPP-UHFFFAOYSA-N 4-sulfanyl-3h-1,3-benzothiazole-2-thione Chemical compound C1=CC=C2SC(S)=NC2=C1S JFISFZKKYWLPPP-UHFFFAOYSA-N 0.000 claims description 3
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 claims description 3
- CMKBCTPCXZNQKX-UHFFFAOYSA-N cyclohexanethiol Chemical compound SC1CCCCC1 CMKBCTPCXZNQKX-UHFFFAOYSA-N 0.000 claims description 3
- WQABCVAJNWAXTE-UHFFFAOYSA-N dimercaprol Chemical compound OCC(S)CS WQABCVAJNWAXTE-UHFFFAOYSA-N 0.000 claims description 3
- DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 claims description 2
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims description 2
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 claims description 2
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- NBJODVYWAQLZOC-UHFFFAOYSA-L [dibutyl(octanoyloxy)stannyl] octanoate Chemical compound CCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCC NBJODVYWAQLZOC-UHFFFAOYSA-L 0.000 claims description 2
- NNLOHLDVJGPUFR-UHFFFAOYSA-L calcium;3,4,5,6-tetrahydroxy-2-oxohexanoate Chemical compound [Ca+2].OCC(O)C(O)C(O)C(=O)C([O-])=O.OCC(O)C(O)C(O)C(=O)C([O-])=O NNLOHLDVJGPUFR-UHFFFAOYSA-L 0.000 claims description 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 claims description 2
- RXPAJWPEYBDXOG-UHFFFAOYSA-N hydron;methyl 4-methoxypyridine-2-carboxylate;chloride Chemical compound Cl.COC(=O)C1=CC(OC)=CC=N1 RXPAJWPEYBDXOG-UHFFFAOYSA-N 0.000 claims description 2
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 claims description 2
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical class SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 claims description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 4
- UTBIMNXEDGNJFE-UHFFFAOYSA-N 2,3,6-trimethylpyridine Chemical compound CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 2
- KAJBSGLXSREIHP-UHFFFAOYSA-N 2,2-bis[(2-sulfanylacetyl)oxymethyl]butyl 2-sulfanylacetate Chemical compound SCC(=O)OCC(CC)(COC(=O)CS)COC(=O)CS KAJBSGLXSREIHP-UHFFFAOYSA-N 0.000 claims 1
- YQNVPNRHJFZONU-UHFFFAOYSA-N 2,3-dimethylbutan-2-amine Chemical compound CC(C)C(C)(C)N YQNVPNRHJFZONU-UHFFFAOYSA-N 0.000 claims 1
- PSYGHMBJXWRQFD-UHFFFAOYSA-N 2-(2-sulfanylacetyl)oxyethyl 2-sulfanylacetate Chemical compound SCC(=O)OCCOC(=O)CS PSYGHMBJXWRQFD-UHFFFAOYSA-N 0.000 claims 1
- JJSYPAGPNHFLML-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;3-sulfanylpropanoic acid Chemical compound OC(=O)CCS.OC(=O)CCS.OC(=O)CCS.CCC(CO)(CO)CO JJSYPAGPNHFLML-UHFFFAOYSA-N 0.000 claims 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- DIVTWACHZOQOBF-UHFFFAOYSA-K diacetyloxy(butyl)stannanylium;acetate Chemical compound CCCC[Sn](OC(C)=O)(OC(C)=O)OC(C)=O DIVTWACHZOQOBF-UHFFFAOYSA-K 0.000 claims 1
- PKKGKUDPKRTKLJ-UHFFFAOYSA-L dichloro(dimethyl)stannane Chemical compound C[Sn](C)(Cl)Cl PKKGKUDPKRTKLJ-UHFFFAOYSA-L 0.000 claims 1
- VHJLVAABSRFDPM-ZXZARUISSA-N dithioerythritol Chemical compound SC[C@H](O)[C@H](O)CS VHJLVAABSRFDPM-ZXZARUISSA-N 0.000 claims 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 claims 1
- CRHIAMBJMSSNNM-UHFFFAOYSA-N tetraphenylstannane Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CRHIAMBJMSSNNM-UHFFFAOYSA-N 0.000 claims 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 50
- 238000000576 coating method Methods 0.000 description 47
- 239000008199 coating composition Substances 0.000 description 46
- 239000003973 paint Substances 0.000 description 44
- 229920005989 resin Polymers 0.000 description 37
- 239000011347 resin Substances 0.000 description 37
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 36
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 29
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 27
- 239000011248 coating agent Substances 0.000 description 21
- 238000010438 heat treatment Methods 0.000 description 21
- 239000002904 solvent Substances 0.000 description 19
- 238000012360 testing method Methods 0.000 description 18
- 239000012975 dibutyltin dilaurate Substances 0.000 description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical group CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 16
- 239000000499 gel Substances 0.000 description 16
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 15
- 241000894007 species Species 0.000 description 15
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 14
- 150000002513 isocyanates Chemical class 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 11
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 10
- 239000007921 spray Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 9
- 239000011521 glass Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 150000003335 secondary amines Chemical class 0.000 description 8
- 230000008901 benefit Effects 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 150000003141 primary amines Chemical class 0.000 description 7
- 238000005507 spraying Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000003542 behavioural effect Effects 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 239000003431 cross linking reagent Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 4
- VGEWEGHHYWGXGG-UHFFFAOYSA-N ethyl n-hydroxycarbamate Chemical compound CCOC(=O)NO VGEWEGHHYWGXGG-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229920005906 polyester polyol Polymers 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 229910001868 water Inorganic materials 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- 239000003677 Sheet moulding compound Substances 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 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 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 229920001002 functional polymer Polymers 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000012970 tertiary amine catalyst Substances 0.000 description 3
- 230000001960 triggered effect Effects 0.000 description 3
- SRZXCOWFGPICGA-UHFFFAOYSA-N 1,6-Hexanedithiol Chemical compound SCCCCCCS SRZXCOWFGPICGA-UHFFFAOYSA-N 0.000 description 2
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 2
- OELQSSWXRGADDE-UHFFFAOYSA-N 2-methylprop-2-eneperoxoic acid Chemical compound CC(=C)C(=O)OO OELQSSWXRGADDE-UHFFFAOYSA-N 0.000 description 2
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 2
- HYFWTVWZCZMWEZ-UHFFFAOYSA-N 4-(3-hydroxyphenyl)benzene-1,3-diol Chemical group OC1=CC(O)=CC=C1C1=CC=CC(O)=C1 HYFWTVWZCZMWEZ-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229920005692 JONCRYL® Polymers 0.000 description 2
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000010793 Steam injection (oil industry) Methods 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 150000001253 acrylic acids Chemical class 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000009918 complex formation Effects 0.000 description 2
- 238000010668 complexation reaction Methods 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical group CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- AZIQALWHRUQPHV-UHFFFAOYSA-N prop-2-eneperoxoic acid Chemical compound OOC(=O)C=C AZIQALWHRUQPHV-UHFFFAOYSA-N 0.000 description 2
- 229920003987 resole Polymers 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- QXRRAZIZHCWBQY-UHFFFAOYSA-N 1,1-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1(CN=C=O)CCCCC1 QXRRAZIZHCWBQY-UHFFFAOYSA-N 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-Me3C6H3 Natural products CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical class O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 1
- ICLCCFKUSALICQ-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanato-3-methylphenyl)-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(C=2C=C(C)C(N=C=O)=CC=2)=C1 ICLCCFKUSALICQ-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- KUMMBDBTERQYCG-UHFFFAOYSA-N 2,6-bis(hydroxymethyl)-4-methylphenol Chemical group CC1=CC(CO)=C(O)C(CO)=C1 KUMMBDBTERQYCG-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- GELMWIVBBPAMIO-UHFFFAOYSA-N 2-methylbutan-2-amine Chemical compound CCC(C)(C)N GELMWIVBBPAMIO-UHFFFAOYSA-N 0.000 description 1
- SHIZASOIRBQZSX-UHFFFAOYSA-N 3,6-dimethylbenzene-1,2-dithiol Chemical group CC1=CC=C(C)C(S)=C1S SHIZASOIRBQZSX-UHFFFAOYSA-N 0.000 description 1
- AQIIVEISJBBUCR-UHFFFAOYSA-N 4-(3-phenylpropyl)pyridine Chemical compound C=1C=NC=CC=1CCCC1=CC=CC=C1 AQIIVEISJBBUCR-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- WLHCBQAPPJAULW-UHFFFAOYSA-N 4-methylbenzenethiol Chemical compound CC1=CC=C(S)C=C1 WLHCBQAPPJAULW-UHFFFAOYSA-N 0.000 description 1
- ZCILGMFPJBRCNO-UHFFFAOYSA-N 4-phenyl-2H-benzotriazol-5-ol Chemical compound OC1=CC=C2NN=NC2=C1C1=CC=CC=C1 ZCILGMFPJBRCNO-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- HIYMVNQRCDAUOK-UHFFFAOYSA-L C(C)(=O)OCCCC.C(CCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCC)(=O)[O-].C(CCC)[Sn+2]CCCC Chemical compound C(C)(=O)OCCCC.C(CCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCC)(=O)[O-].C(CCC)[Sn+2]CCCC HIYMVNQRCDAUOK-UHFFFAOYSA-L 0.000 description 1
- 101100161935 Caenorhabditis elegans act-4 gene Proteins 0.000 description 1
- 239000005745 Captan Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VKOUCJUTMGHNOR-UHFFFAOYSA-N Diphenolic acid Chemical compound C=1C=C(O)C=CC=1C(CCC(O)=O)(C)C1=CC=C(O)C=C1 VKOUCJUTMGHNOR-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 229910001335 Galvanized steel Inorganic materials 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- OMRDSWJXRLDPBB-UHFFFAOYSA-N N=C=O.N=C=O.C1CCCCC1 Chemical compound N=C=O.N=C=O.C1CCCCC1 OMRDSWJXRLDPBB-UHFFFAOYSA-N 0.000 description 1
- HDONYZHVZVCMLR-UHFFFAOYSA-N N=C=O.N=C=O.CC1CCCCC1 Chemical compound N=C=O.N=C=O.CC1CCCCC1 HDONYZHVZVCMLR-UHFFFAOYSA-N 0.000 description 1
- JTDWCIXOEPQECG-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCC(C)(C)C Chemical compound N=C=O.N=C=O.CCCCCC(C)(C)C JTDWCIXOEPQECG-UHFFFAOYSA-N 0.000 description 1
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 241000158147 Sator Species 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- JJLKTTCRRLHVGL-UHFFFAOYSA-L [acetyloxy(dibutyl)stannyl] acetate Chemical compound CC([O-])=O.CC([O-])=O.CCCC[Sn+2]CCCC JJLKTTCRRLHVGL-UHFFFAOYSA-L 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical class CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000004808 allyl alcohols Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- JQRRFDWXQOQICD-UHFFFAOYSA-N biphenylen-1-ylboronic acid Chemical compound C12=CC=CC=C2C2=C1C=CC=C2B(O)O JQRRFDWXQOQICD-UHFFFAOYSA-N 0.000 description 1
- JAONZGLTYYUPCT-UHFFFAOYSA-K bismuth subgallate Chemical compound OC(=O)C1=CC(O)=C2O[Bi](O)OC2=C1 JAONZGLTYYUPCT-UHFFFAOYSA-K 0.000 description 1
- 229960000199 bismuth subgallate Drugs 0.000 description 1
- ZREIPSZUJIFJNP-UHFFFAOYSA-K bismuth subsalicylate Chemical compound C1=CC=C2O[Bi](O)OC(=O)C2=C1 ZREIPSZUJIFJNP-UHFFFAOYSA-K 0.000 description 1
- 229960000782 bismuth subsalicylate Drugs 0.000 description 1
- CZEHCTMLBPSXDK-UHFFFAOYSA-L bismuth(2+);7,7-dimethyloctanoate Chemical compound [Bi+2].CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O CZEHCTMLBPSXDK-UHFFFAOYSA-L 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- LUZSPGQEISANPO-UHFFFAOYSA-N butyltin Chemical compound CCCC[Sn] LUZSPGQEISANPO-UHFFFAOYSA-N 0.000 description 1
- 229940117949 captan Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011094 fiberboard Substances 0.000 description 1
- HDVRLUFGYQYLFJ-UHFFFAOYSA-N flamenol Chemical compound COC1=CC(O)=CC(O)=C1 HDVRLUFGYQYLFJ-UHFFFAOYSA-N 0.000 description 1
- 239000005357 flat glass Substances 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000008397 galvanized steel Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical class CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- RCHKEJKUUXXBSM-UHFFFAOYSA-N n-benzyl-2-(3-formylindol-1-yl)acetamide Chemical compound C12=CC=CC=C2C(C=O)=CN1CC(=O)NCC1=CC=CC=C1 RCHKEJKUUXXBSM-UHFFFAOYSA-N 0.000 description 1
- CATWEXRJGNBIJD-UHFFFAOYSA-N n-tert-butyl-2-methylpropan-2-amine Chemical compound CC(C)(C)NC(C)(C)C CATWEXRJGNBIJD-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 125000005474 octanoate group Chemical group 0.000 description 1
- 239000003921 oil Chemical class 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000010957 pewter Substances 0.000 description 1
- 229910000498 pewter Inorganic materials 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 230000004481 post-translational protein modification Effects 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 238000010944 pre-mature reactiony Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010107 reaction injection moulding Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000005496 tempering Methods 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/14—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of germanium, tin or lead
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/089—Reaction retarding agents
-
- 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
- C08G18/1891—Catalysts containing secondary or tertiary amines or salts thereof in vaporous state
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/24—Catalysts containing metal compounds of tin
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US84481086A | 1986-03-27 | 1986-03-27 | |
| US06/931,610 US4788083A (en) | 1986-03-27 | 1986-11-17 | Tin or bismuth complex catalysts and trigger cure of coatings therewith |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH672750A5 true CH672750A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-12-29 |
Family
ID=27126530
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1178/87A CH672750A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1986-03-27 | 1987-03-27 |
Country Status (25)
Families Citing this family (100)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1324857C (en) * | 1987-01-12 | 1993-11-30 | Gary M. Carlson | Stabilized moisture curable polyurethane coatings |
| JPH0832840B2 (ja) * | 1987-09-09 | 1996-03-29 | 三共有機合成株式会社 | カチオン電着塗料用硬化触媒 |
| FR2649711B1 (fr) * | 1989-07-13 | 1993-01-22 | Essilor Int | Compositions de polymeres a base de polythiourethanes pour la fabrication de verres organiques |
| US5154950A (en) * | 1989-12-07 | 1992-10-13 | Miles Inc. | Rapid curing, light stable, two-component polyurethane coating compositions |
| EP0454219A1 (en) * | 1990-04-24 | 1991-10-30 | Akzo N.V. | Polyurethane reaction mixtures and coating compositions therefrom |
| JP2983370B2 (ja) * | 1991-04-16 | 1999-11-29 | 関西ペイント株式会社 | 電着塗料組成物 |
| DE4118850A1 (de) * | 1991-06-07 | 1992-12-10 | Fehrer Gummihaar | Verfahren zur herstellung von weich-polyurethanschaum |
| US5491174A (en) * | 1992-10-09 | 1996-02-13 | The Dow Chemical Company | Process for preparation of polyurethanes utilizing novel catalysts |
| CN1042842C (zh) * | 1993-05-31 | 1999-04-07 | 谭秉彝 | 电解食盐生产氯酸钠的方法 |
| US6001900A (en) * | 1993-07-28 | 1999-12-14 | Elf Atochem North America, Inc. | Metal containing e-coat catalysts optionally with tin catalysts |
| US5718817A (en) * | 1993-07-28 | 1998-02-17 | Elf Atochem North America, Inc. | Catalyst for low temperature cure of blocked isocyanates |
| DE69412231T2 (de) * | 1993-09-22 | 1998-12-10 | Ashland Oil Inc., Columbus, Ohio | Polyurethan-reaktionssystem mit blockierter katalysatorkombination |
| DE69527224T2 (de) * | 1994-04-15 | 2002-10-17 | Ppg Industries Ohio, Inc. | Beschichtungsverfahren |
| US5820925A (en) * | 1994-04-15 | 1998-10-13 | Imperial Chemical Industries Plc. | Coating process |
| US5478790A (en) * | 1994-04-20 | 1995-12-26 | Ashland Oil, Inc. | Blocked tin catalyst system for use with mercapto resin/acrylic resin blends |
| US5587448A (en) * | 1994-12-29 | 1996-12-24 | Minnesota Mining And Manufacturing | Reaction system for producing a polyurethane and method of using same to seal a surface |
| US5698613A (en) * | 1995-02-21 | 1997-12-16 | Mancuso Chemicals Limited | Chemical binder |
| US5646195A (en) * | 1995-03-07 | 1997-07-08 | The Dow Chemical Company | Catalyst for polyurethane carpet backings and carpets prepared therewith |
| US5849864A (en) * | 1996-08-01 | 1998-12-15 | Ashland Chemical Company | Sulfonic acid blocked metal catalysts for amine trigger urethane reactions |
| US5891292A (en) * | 1996-08-05 | 1999-04-06 | Science Research Laboratory, Inc. | Method of making fiber reinforced composites and coatings |
| BR9711862A (pt) * | 1996-10-05 | 2001-08-28 | Tioxide Specialties Ltd | Catalisador, e, processo de cura de uma composição |
| US6545117B1 (en) | 1997-08-07 | 2003-04-08 | Akzo Noble N.V. | Sprayable coating compositions comprising an oxazolidine functional compound, an isocyanate functional compound, and a compound selected from a mercapto and a sulfonic acid functional compound |
| US5972422A (en) * | 1998-05-01 | 1999-10-26 | Basf Corporation | Method for low bake repair of composite color-plus-clear coatings, and compositions for use therein |
| US6045872A (en) * | 1998-05-01 | 2000-04-04 | Basf Corporation | Method for eliminating wrinkling in composite color-plus-clear coatings, and compositions for use therein |
| US5902894A (en) * | 1998-08-26 | 1999-05-11 | Catalytic Distillation Technologies | Process for making dialkyl carbonates |
| DE19840318A1 (de) | 1998-09-04 | 2000-03-09 | Bayer Ag | Reaktivbindemittel mit verlängerter Topfzeit |
| US6190524B1 (en) | 1999-03-26 | 2001-02-20 | Ppg Industries Ohio, Inc. | Organosulfur bismuth compounds and their use in electrodepositable coating compositions |
| US6486090B1 (en) * | 1999-11-04 | 2002-11-26 | 3M Innovative Properties Company | Initiator/hydroxide and initiator/alkoxide complexes, systems comprising the complexes, and polymerized compositions made therewith |
| DE10001222A1 (de) | 2000-01-14 | 2001-08-09 | Basf Coatings Ag | Beschichtung, enthaltend kolloidal verteiltes metallisches Bismut |
| DE60125929T2 (de) * | 2000-05-26 | 2007-11-08 | Akzo Nobel Coatings International B.V. | Photoaktivierbare beschichtungszusammensetzung |
| US6548617B2 (en) | 2000-11-30 | 2003-04-15 | Akzo Nobel N.V. | Coating composition comprising a bicyclo-orthoester-functional compound, an isocyanate-functional compound, and a thiol-functional compound |
| US7005477B1 (en) | 2002-05-16 | 2006-02-28 | Mcp Industries, Inc. | Moisture-curing polyurethane material having a long gel time |
| EP1408062A1 (de) * | 2002-10-08 | 2004-04-14 | Sika Technology AG | Bismutkatalysierte Polyurethanzusammensetzung |
| ES2291434T3 (es) * | 2002-12-23 | 2008-03-01 | Dow Global Technologies Inc. | Composicion reactiva de poliuretano. |
| DE60208403T2 (de) * | 2002-12-23 | 2009-10-01 | Dow Global Technologies, Inc., Midland | Reaktive Polyurethanzusammensetzung |
| US20050038204A1 (en) * | 2003-08-14 | 2005-02-17 | Walters David N. | Increased pot-life urethane coatings |
| CN102408366B (zh) | 2004-02-17 | 2014-04-16 | 切弗朗菲利浦化学公司 | 含硫组合物及其制造方法 |
| US8003748B2 (en) * | 2004-02-17 | 2011-08-23 | Chevron Phillips Chemical Company, Lp | Polythiourethane compositions and processes for making and using same |
| ES2276182T5 (es) * | 2004-03-12 | 2015-04-10 | Dow Global Technologies Llc | Composición adhesiva epoxídica |
| RU2268899C1 (ru) * | 2004-05-05 | 2006-01-27 | Владимир Андреевич Варюхин | Способ получения огнестойкого пенополиуретана |
| US7977446B2 (en) * | 2004-06-16 | 2011-07-12 | E. I. Du Pont De Nemours And Company | Air-activated organotin catalysts for polyurethane synthesis |
| WO2005123862A1 (en) * | 2004-06-18 | 2005-12-29 | Akzo Nobel Coatings International B.V. | Multilayer coating system |
| US7297748B2 (en) * | 2004-08-31 | 2007-11-20 | Rhodia Inc. | Direct to metal polyurethane coating compositions |
| WO2006064035A1 (en) * | 2004-12-15 | 2006-06-22 | Akzo Nobel Coatings International B.V. | Water borne coating composition containing thiol functional compounds |
| AU2006266124B2 (en) * | 2005-06-29 | 2009-11-19 | Saint-Gobain Abrasives, Inc. | High performance resin for abrasive products |
| EP1940992A1 (en) * | 2005-08-16 | 2008-07-09 | Chevron Phillips Chemical Company LP | Mercaptan-hardened epoxy polymer compositions and processes for making and using same |
| AU2006279788A1 (en) | 2005-08-16 | 2007-02-22 | Chevron Phillips Chemical Company Lp | Polymer compositions and processes for making and using same |
| JP2009504865A (ja) * | 2005-08-17 | 2009-02-05 | アクゾ ノーベル コーティングス インターナショナル ビー ヴィ | ポリイソシアネートおよびポリオールを含んでいるコーティング組成物 |
| DE602006013835D1 (de) * | 2005-08-17 | 2010-06-02 | Akzo Nobel Coatings Int Bv | Beschichtungszusammensetzung, enthaltend ein polyisocyanat und ein polyol |
| WO2007034330A2 (en) * | 2005-09-23 | 2007-03-29 | Spectraglass Holdings Pty. Ltd. | Isocyanate prepolymer catalysts and related curing processes |
| US7625992B2 (en) * | 2006-04-18 | 2009-12-01 | E. I. Du Pont De Nemours And Company | Processes for polyurethane polymerization using polysilyl derivatives of germanium and tin as catalysts |
| US8609579B2 (en) * | 2006-10-26 | 2013-12-17 | Ashland Licensing And Intellectual Property Llc | Composition capable of radiation activated catalysis and radiation curable urethane containing the composition |
| US20080099141A1 (en) * | 2006-10-26 | 2008-05-01 | Ashland Inc. | Method of producing flexible laminates |
| US20140276470A1 (en) | 2006-11-07 | 2014-09-18 | Raymond Lareau | Dialysis Catheters with Fluoropolymer Additives |
| US8603070B1 (en) | 2013-03-15 | 2013-12-10 | Angiodynamics, Inc. | Catheters with high-purity fluoropolymer additives |
| DE102006058527A1 (de) * | 2006-12-12 | 2008-06-19 | Bayer Materialscience Ag | Klebstoffe |
| EP2102258B1 (en) | 2006-12-14 | 2016-10-19 | Interface Biologics Inc. | Surface modifying macromolecules with high degradation temperatures and uses thereof |
| US20080214774A1 (en) * | 2007-03-01 | 2008-09-04 | Chevron Phillips Chemical Company, Lp | Thiourethane Compositions and Processes for Making and Using Same |
| ES2397490T3 (es) † | 2007-09-13 | 2013-03-07 | E. I. Du Pont De Nemours And Company | Composición de revestimiento de base acuosa de dos componentes |
| US8318830B2 (en) * | 2007-10-17 | 2012-11-27 | Basf Se | Photolatent catalysts based on organometallic compounds |
| US20090124784A1 (en) * | 2007-11-08 | 2009-05-14 | Brown Chad W | Methods and compounds for curing polythiourethane compositions |
| US20090124762A1 (en) * | 2007-11-08 | 2009-05-14 | Brown Chad W | Methods and systems for the selective formation of thiourethane bonds and compounds formed therefrom |
| DE102008021980A1 (de) * | 2008-05-02 | 2009-11-05 | Bayer Materialscience Ag | Neue Katalysatoren und deren Einsatz bei der Herstellung von Polyurethanen |
| WO2010025398A1 (en) | 2008-08-28 | 2010-03-04 | Interface Biologics Inc. | Thermally stable biuret and isocyanurate based surface modifying macromolecules and uses thereof |
| JP2012506467A (ja) | 2008-10-22 | 2012-03-15 | アクゾ ノーベル コーティングス インターナショナル ビー ヴィ | ポリイソシアナート及びポリオールを含む被覆用組成物 |
| RU2011143809A (ru) | 2009-03-31 | 2013-05-10 | Акцо Нобель Коатингс Интернэшнл Б.В. | Радиационное отверждение покрытий |
| DK2295132T3 (en) | 2009-05-15 | 2016-12-05 | Interface Biologics Inc | Antithrombogenic hollow-fiber membranes, molding material and blood long |
| RU2552980C2 (ru) * | 2009-11-04 | 2015-06-10 | Хантсмэн Интернэшнл Ллс | Жидкая изоцианатная композиция |
| US8240386B2 (en) * | 2009-12-30 | 2012-08-14 | Schlumberger Technology Corporation | Method for treating well bore with polyurethane composition |
| WO2011104224A1 (de) * | 2010-02-26 | 2011-09-01 | Basf Se | Katalysierte granulattemperung für thermoplastische polyurethane |
| US20120178877A1 (en) * | 2011-03-21 | 2012-07-12 | Energyguard Atlantic, Llc, Dba Ener.Co | Thermally conductive nanocomposite coating compositions |
| DE102011007504A1 (de) * | 2011-04-15 | 2012-10-18 | Henkel Ag & Co. Kgaa | PU-Zusammensetzungen mit komplexierten Katalysatoren |
| EP2822983B1 (en) * | 2012-03-07 | 2018-11-21 | Akzo Nobel Coatings International B.V. | Non-aqueous liquid coating composition |
| US9416214B2 (en) | 2012-04-25 | 2016-08-16 | Dow Global Technologies Llc | Polyurethanes made using bismuth thiocarbamate or thiocarbonate salts as catalysts |
| US9340639B2 (en) | 2012-04-25 | 2016-05-17 | Dow Global Technologies Llc | Polyurethanes made using bismuth thiophosphoric acid diester salts as catalysts |
| ES2556409T3 (es) | 2012-08-13 | 2016-01-15 | Tib Chemicals Ag | Catalizadores termolatentes, su preparación y su uso |
| US9206283B1 (en) | 2013-03-15 | 2015-12-08 | Angiodynamics, Inc. | Thermoplastic polyurethane admixtures |
| US8784402B1 (en) | 2013-03-15 | 2014-07-22 | Angiodynamics, Inc. | Catheters with fluoropolymer additives |
| US10166321B2 (en) | 2014-01-09 | 2019-01-01 | Angiodynamics, Inc. | High-flow port and infusion needle systems |
| WO2016054733A1 (en) | 2014-10-06 | 2016-04-14 | Interface Biologics, Inc. | Packaging materials including a barrier film |
| JP6689858B2 (ja) * | 2015-01-13 | 2020-04-28 | ザ・シェファード・ケミカル・カンパニーＴｈｅ Ｓｈｅｐｈｅｒｄ Ｃｈｅｍｉｃａｌ Ｃｏｍｐａｎｙ | 新規ポリウレタン硬化剤 |
| CN109071999B (zh) * | 2016-04-22 | 2021-09-21 | 科思创德国股份有限公司 | 热潜催化的双组分体系 |
| EP3529300A4 (en) | 2016-10-18 | 2020-03-18 | Evonik Canada Inc. | PLASTICIZED PVC BLENDS WITH SURFACE MODIFYING MACROMOLECULES AND ARTICLES MADE THEREFROM |
| US11306174B2 (en) * | 2017-05-08 | 2022-04-19 | Ppg Industries Ohio, Inc. | Curable film-forming compositions demonstrating decreased cure time with stable pot life |
| WO2019002538A1 (de) * | 2017-06-30 | 2019-01-03 | Sika Technology Ag | Zweikomponentige polyurethanzusammensetzung mit einstellbarer topfzeit |
| EP3652229A1 (en) | 2017-07-14 | 2020-05-20 | Fresenius Medical Care Holdings, Inc. | Method for providing surface modifying composition with improved byproduct removal |
| US10773243B2 (en) * | 2017-09-07 | 2020-09-15 | Ppg Industries Ohio, Inc. | Thermolatent catalyst and its use in curable compositions |
| US20190106527A1 (en) * | 2017-10-10 | 2019-04-11 | Allnex Netherlands Bv | Non-aqueous crosslinkable composition |
| CN112839985B (zh) * | 2018-11-09 | 2023-10-20 | 株式会社可乐丽 | 抛光层用聚氨酯、抛光层、抛光垫及抛光层的改性方法 |
| WO2020127484A1 (de) * | 2018-12-21 | 2020-06-25 | Sika Technology Ag | Verfahren für den 3d-druck von zweikomponentigen polyurethanzusammensetzungen |
| KR102225086B1 (ko) * | 2019-04-05 | 2021-03-10 | 효성티앤씨 주식회사 | 폴리에스터 중합 촉매 및 이를 이용한 폴리에스터의 제조방법 |
| US20220306894A1 (en) * | 2019-08-23 | 2022-09-29 | Basf Coatings Gmbh | Coating material system comprising a mercapto group-containing compound |
| CN114555733B (zh) * | 2019-10-14 | 2024-05-07 | 巴斯夫涂料有限公司 | 基于包含至少一个芳族取代基的含铋催化剂的涂料体系 |
| US20230047357A1 (en) * | 2020-03-25 | 2023-02-16 | Sika Technology Ag | Two-component polyurethane composition with a high degree of hydrophobicity and adjustable pot life |
| EP3960782A1 (de) * | 2020-08-27 | 2022-03-02 | Sika Technology Ag | Polyurethanzusammensetzung geeignet als bodenbeschichtung mit einstellbarer topfzeit |
| EP4288474A1 (de) * | 2021-02-02 | 2023-12-13 | Sika Technology AG | Zweikomponentige polyurethanspachtelmasse mit einstellbarer topfzeit |
| US20220411563A1 (en) | 2021-06-28 | 2022-12-29 | Covestro Llc | Novel dual cure 3d printing resins |
| CN114456352B (zh) * | 2021-12-21 | 2023-11-07 | 四川东树新材料有限公司 | 拉挤用聚氨酯组合料及其应用 |
| US20250145851A1 (en) * | 2022-01-31 | 2025-05-08 | Ppg Industries Ohio, Inc. | Curable coating compositions |
| CN115975586B (zh) * | 2022-12-08 | 2025-01-14 | 湖北回天新材料股份有限公司 | 一种双组分聚氨酯结构胶及其应用 |
Family Cites Families (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3124544A (en) * | 1964-03-10 | Method of stabilizing cellular poly- | ||
| US3124543A (en) * | 1964-03-10 | Method of stabilizing cellular poly- | ||
| NL106889C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1957-09-25 | 1900-01-01 | ||
| BE618837A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1961-06-12 | |||
| US3219589A (en) * | 1961-12-06 | 1965-11-23 | Continental Oil Co | Catalyst systems and methods of making catalysts |
| GB1074645A (en) * | 1965-06-25 | 1967-07-05 | Ici Ltd | Process for the production of polyurethanes |
| US3446780A (en) * | 1965-08-31 | 1969-05-27 | Thiokol Chemical Corp | Mercaptan containing polyurethane compositions,process and cured products thereof |
| NL134732C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1966-08-01 | |||
| DE1768838A1 (de) * | 1967-07-19 | 1972-04-13 | Inst Przemyslu Organiczego | Verfahren zur Herstellung der Merkaptoorganozinnverbindungen |
| DE1805720A1 (de) * | 1967-11-20 | 1969-06-19 | Uniroyal Inc | Verfahren zur Festlegung der Reaktivitaet von Glykol,Diisocyanat bzw. deren Gemischen in vorbestimmter Groessenordnung |
| US3635906A (en) * | 1968-11-12 | 1972-01-18 | Du Pont | Preparation of polyurethanes using organo-tin catalyst and time-lapse modifier |
| GB1332700A (en) * | 1971-11-29 | 1973-10-03 | British Titan Ltd | Stabilised stannous salt compositions |
| US3784521A (en) * | 1972-04-11 | 1974-01-08 | Goodyear Tire & Rubber | Method of accelerating the cure of polyurethanes |
| US3783152A (en) * | 1972-04-27 | 1974-01-01 | Grace W R & Co | N-arylene polycarbamate |
| US3933727A (en) * | 1972-09-26 | 1976-01-20 | Ab Bofors | Method of producing polyurethane-based cores and moulds according to the so-called cold-box procedure |
| US4011181A (en) * | 1973-07-02 | 1977-03-08 | Olin Corporation | Polyurethane foams containing stannous catechol derivatives |
| US3914198A (en) * | 1973-08-29 | 1975-10-21 | Dow Chemical Co | Rapid-setting polyurethanes |
| US4022721A (en) * | 1974-09-26 | 1977-05-10 | Mitsubishi Chemical Industries Ltd. | Process for producing compounds having an oxazolidone ring using a complex of aluminum halide catalyst |
| US3972829A (en) * | 1974-11-07 | 1976-08-03 | Universal Oil Products Company | Method of depositing a catalytically active metallic component on a carrier material |
| US3945981A (en) * | 1974-11-08 | 1976-03-23 | Uniroyal, Inc. | Light stable polyurethane elastomer prepared from aliphatic isocyanate using thio tin organic compound containing sulfur attached to tin as heat activated catalyst |
| US4081429A (en) * | 1976-02-13 | 1978-03-28 | Arnco | Heat-stabilized polyurethane elastomer |
| US4038114A (en) * | 1976-08-20 | 1977-07-26 | The United States Of America As Represented By The Secretary Of The Air Force | Catalyst system for polyurethane propellant compositions |
| GB2029831A (en) * | 1977-12-06 | 1980-03-26 | Camprex Ltd | Triorganotin Salts and their use in Improved Ablative Antifouling Compositions |
| EP0002724A1 (en) * | 1977-12-23 | 1979-07-11 | Mobay Chemical Corporation | Process for the production of elastomeric polyurethane moldings and the product of this process |
| CA1122737A (en) * | 1978-02-21 | 1982-04-27 | Robert A. Laitar | Binder compositions containing phenolic resins and organic phosphate and/or carbonate solvents |
| US4239857A (en) * | 1978-06-29 | 1980-12-16 | Union Carbide Corporation | Process for producing solid or microcellular polyurethane elastomers having improved green strength |
| US4237235A (en) * | 1978-08-21 | 1980-12-02 | Rosalba Mazzucco | Urethanic polymerization by chelating agents acting as catalysts or cocatalysts |
| US4254017A (en) * | 1978-11-13 | 1981-03-03 | M&T Chemicals Inc. | Organotin mercaptoalkanol esters and alkoxides containing sulfide groups |
| US4310454A (en) * | 1979-04-03 | 1982-01-12 | Ciba-Geigy Corporation | Novel organo-tin compounds |
| US4273885A (en) * | 1980-04-01 | 1981-06-16 | Texaco Development Corp. | Novel catalyst system for RIM elastomers |
| GB2088886B (en) * | 1980-10-06 | 1984-07-18 | Mitsubishi Petrochemical Co | Binder composition for foundry molds or cores |
| GB2087908B (en) * | 1980-11-20 | 1984-10-03 | Texaco Development Corp | Stannous halide alcohol complexes and their use in preparing polyurethanes |
| DE3047926C2 (de) * | 1980-12-19 | 1985-05-15 | Th. Goldschmidt Ag, 4300 Essen | Härtbares Klebmittel |
| US4517222A (en) * | 1983-03-10 | 1985-05-14 | Ashland Oil, Inc. | Vaporous amine catalyst spray method of applying a film to a substrate |
| GB2139625B (en) * | 1983-05-03 | 1987-05-13 | Ciba Geigy Ag | Novel organo-tin pvc stabilisers |
-
1986
- 1986-11-17 US US06/931,610 patent/US4788083A/en not_active Expired - Lifetime
-
1987
- 1987-02-11 AU AU68684/87A patent/AU575741B2/en not_active Ceased
- 1987-02-16 GB GB8703528A patent/GB2188327B/en not_active Expired - Lifetime
- 1987-02-23 IN IN154/DEL/87A patent/IN168614B/en unknown
- 1987-03-18 ES ES8700773A patent/ES2004125A6/es not_active Expired
- 1987-03-18 IT IT19749/87A patent/IT1203375B/it active
- 1987-03-23 SE SE8701195A patent/SE466138B/sv not_active IP Right Cessation
- 1987-03-24 DE DE19873709631 patent/DE3709631A1/de active Granted
- 1987-03-25 FR FR878704163A patent/FR2596292B1/fr not_active Expired - Lifetime
- 1987-03-25 MX MX005714A patent/MX168226B/es unknown
- 1987-03-25 BE BE8700306A patent/BE1001374A3/fr not_active IP Right Cessation
- 1987-03-25 DK DK151187A patent/DK167619B1/da not_active IP Right Cessation
- 1987-03-25 NO NO871251A patent/NO169547C/no not_active IP Right Cessation
- 1987-03-25 CA CA000533010A patent/CA1303015C/en not_active Expired - Lifetime
- 1987-03-25 IL IL82003A patent/IL82003A/xx not_active IP Right Cessation
- 1987-03-25 RU SU874202202A patent/RU2024553C1/ru active
- 1987-03-26 NZ NZ219791A patent/NZ219791A/xx unknown
- 1987-03-26 NL NL8700713A patent/NL194044C/nl not_active IP Right Cessation
- 1987-03-26 HU HU871330A patent/HU207745B/hu not_active IP Right Cessation
- 1987-03-26 FI FI871338A patent/FI93849C/fi not_active IP Right Cessation
- 1987-03-26 KR KR1019870002759A patent/KR900005381B1/ko not_active Expired
- 1987-03-26 AT AT0073987A patent/AT398573B/de not_active IP Right Cessation
- 1987-03-26 BR BR8701388A patent/BR8701388A/pt not_active IP Right Cessation
- 1987-03-27 CH CH1178/87A patent/CH672750A5/de not_active IP Right Cessation
- 1987-03-27 CN CN87102399A patent/CN1007256B/zh not_active Expired
-
1990
- 1990-03-30 SE SE9001182A patent/SE504870C2/sv not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH672750A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| EP0065203B1 (de) | Verfahren zur splittersicheren Beschichtung von Glasoberflächen | |
| DE10132938A1 (de) | Nichtwässriges, wärmehärtendes Zweikomponenten-Beschichtungsmittel | |
| ES2127852T3 (es) | Dispersion acuosa de resinas de poliuretano, procedimiento de su preparacion, composiciones de revestimiento que contienen estas y su utilizacion. | |
| DE4111392A1 (de) | Verwendung von bindemittelkombinationen und ein verfahren zur herstellung von beschichtungen | |
| EP0443138A1 (de) | Polyisocyanatgemische, Verfahren zu ihrer Herstellung und ihre Verwendung als Bindemittel für Überzugsmittel oder als Reaktionspartner für gegenüber Isocyanatgruppen oder Carboxylgruppen reaktionsfähige Verbindungen | |
| DE10048615A1 (de) | Nichtwäßriges, wärmehärtendes Zweikomponenten-Beschichtungsmittel | |
| EP0546399A2 (de) | Ether- und Urethangruppen aufweisende Polyisocyanate, ein Verfahren zu ihrer Herstellung und ihre Verwendung | |
| EP0000348A1 (de) | Polyuret-Polyisocyanate, Verfahren zu deren Herstellung, sowie deren Verwendung bei der Herstellung von Polyurethankunststoffen. | |
| DE2131299A1 (de) | Durch Hitzeeinwirkung haertbare Gemische | |
| EP0604814A1 (de) | Aminogruppen aufweisende Polyesterharze | |
| DD270868A5 (de) | Aktivierbare katalysator fuer die umsetzung einer hydroxylverbindung mit einer isocyanatverbindung | |
| DE2315910C3 (de) | Lagerstabile Polyurethan-Einkomponentenlacke | |
| DE19546892A1 (de) | Reaktionslacke zur Herstellung von Überzügen oder Grundierungen | |
| DE3618113C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| AT395248B (de) | Verfahren zur aushaertung einer beschichtung | |
| DE3645025C2 (de) | Verfahren zur Aush{rtung eines ]berzugs aus einer Beschichtungsmasse | |
| DE19537026A1 (de) | Neue Polyesterpolyole und ihre Verwendung als Polyolkomponente in Zweikomponenten-Polyurethanlacken | |
| DE3614839A1 (de) | Verbessertes haertungsverfahren fuer magnettontraeger | |
| EP0615993A1 (de) | Härtungsmittel für Zweikomponenten-Polyurethansysteme, insbesondere Zweikomponenten-Polyurethanlacke, sowie ein Verfahren zu ihrer Herstellung | |
| JPS5927967A (ja) | ウレタン結合含有被覆物の製造方法 | |
| DE3618133A1 (de) | Beschichtungsmassen | |
| DE2028892A1 (de) | Hartbare Zusammensetzung | |
| DE19742720A1 (de) | Bis(alkylamino)alkylether-Verbindungen und ihre Verwendung | |
| DE2435419C3 (de) | Verfahren zur Herstellung von Füllungen und Beschichtungen durch Aushärten von Polyisocyanatmassen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |