CA1159191A - Composes de scellement - Google Patents

Composes de scellement

Info

Publication number: CA1159191A
Authority: CA; Canada
Prior art keywords: poly; polythiol; polyether polyol; sealant; oxyalkylene
Prior art date: 1981-04-09
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.): Expired

Application number

CA000375060A

Other languages

English (en)

Inventor

Rector P. Louthan

Richard C. Doss

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Phillips Petroleum Co

Original Assignee

Phillips Petroleum Co

Priority date (The priority date 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 date listed.)

1981-04-09

Filing date

1981-04-09

Publication date

1983-12-20

1981-04-09 Application filed by Phillips Petroleum Co filed Critical Phillips Petroleum Co

1981-04-09 Priority to CA000375060A priority Critical patent/CA1159191A/fr

1983-12-20 Application granted granted Critical

1983-12-20 Publication of CA1159191A publication Critical patent/CA1159191A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 47
239000000565 sealant Substances 0.000 title claims abstract description 40
239000002253 acid Substances 0.000 claims abstract description 28
229920000642 polymer Polymers 0.000 claims abstract description 27
125000003396 thiol group Chemical class [H]S* 0.000 claims abstract description 19
239000003795 chemical substances by application Substances 0.000 claims abstract description 17
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 16
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims abstract description 10
239000000945 filler Substances 0.000 claims abstract description 8
239000004014 plasticizer Substances 0.000 claims abstract description 6
-1 poly(oxyalkylene) Polymers 0.000 claims description 72
229920005862 polyol Polymers 0.000 claims description 56
150000003077 polyols Chemical class 0.000 claims description 42
229920006295 polythiol Polymers 0.000 claims description 32
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
238000000034 method Methods 0.000 claims description 22
229920000570 polyether Polymers 0.000 claims description 20
239000004721 Polyphenylene oxide Substances 0.000 claims description 16
150000002148 esters Chemical class 0.000 claims description 12
LDTLDBDUBGAEDT-UHFFFAOYSA-N methyl 3-sulfanylpropanoate Chemical compound COC(=O)CCS LDTLDBDUBGAEDT-UHFFFAOYSA-N 0.000 claims description 10
230000032050 esterification Effects 0.000 claims description 9
238000005886 esterification reaction Methods 0.000 claims description 9
238000009472 formulation Methods 0.000 claims description 9
MYWWWNVEZBAKHR-UHFFFAOYSA-N methyl 3-(3-methoxy-3-oxopropyl)sulfanylpropanoate Chemical compound COC(=O)CCSCCC(=O)OC MYWWWNVEZBAKHR-UHFFFAOYSA-N 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
125000005599 alkyl carboxylate group Chemical group 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 7
239000003054 catalyst Substances 0.000 claims description 6
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 5
YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical group O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 claims description 5
239000002318 adhesion promoter Substances 0.000 claims description 3
YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical group [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 claims description 3
150000008117 polysulfides Polymers 0.000 claims description 3
239000003963 antioxidant agent Substances 0.000 claims 3
229920001021 polysulfide Polymers 0.000 claims 2
239000005077 polysulfide Substances 0.000 claims 2
230000003078 antioxidant effect Effects 0.000 claims 1
HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical compound OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 claims 1
VXTYCJJHHMLIBM-UHFFFAOYSA-N carboxysulfanylformic acid Chemical compound OC(=O)SC(O)=O VXTYCJJHHMLIBM-UHFFFAOYSA-N 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract description 11
239000007788 liquid Substances 0.000 abstract description 8
229920001451 polypropylene glycol Polymers 0.000 abstract description 6
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
150000003138 primary alcohols Chemical class 0.000 abstract 1
150000007513 acids Chemical class 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
229910052717 sulfur Inorganic materials 0.000 description 8
239000011593 sulfur Substances 0.000 description 8
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000000463 material Substances 0.000 description 6
229930195733 hydrocarbon Natural products 0.000 description 5
150000002430 hydrocarbons Chemical class 0.000 description 5
238000005809 transesterification reaction Methods 0.000 description 5
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
125000002947 alkylene group Chemical group 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
229910000037 hydrogen sulfide Inorganic materials 0.000 description 4
238000002156 mixing Methods 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 3
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
125000005702 oxyalkylene group Chemical group 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
AQLWLHRHIFTILV-UHFFFAOYSA-N 3-(2-carboxypropyldisulfanyl)-2-methylpropanoic acid Chemical compound OC(=O)C(C)CSSCC(C)C(O)=O AQLWLHRHIFTILV-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical class [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-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
150000002009 diols Chemical class 0.000 description 2
239000011521 glass Substances 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000011707 mineral Substances 0.000 description 2
239000003607 modifier Substances 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000758 substrate Substances 0.000 description 2
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
PROQIPRRNZUXQM-UHFFFAOYSA-N (16alpha,17betaOH)-Estra-1,3,5(10)-triene-3,16,17-triol Natural products OC1=CC=C2C3CCC(C)(C(C(O)C4)O)C4C3CCC2=C1 PROQIPRRNZUXQM-UHFFFAOYSA-N 0.000 description 1
ORTVZLZNOYNASJ-UPHRSURJSA-N (z)-but-2-ene-1,4-diol Chemical compound OC\C=C/CO ORTVZLZNOYNASJ-UPHRSURJSA-N 0.000 description 1
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 1
MDJCCLDIFSDFTH-UHFFFAOYSA-N 2-icosyloxirane Chemical compound CCCCCCCCCCCCCCCCCCCCC1CO1 MDJCCLDIFSDFTH-UHFFFAOYSA-N 0.000 description 1
IGMAMGCYKXBOJV-UHFFFAOYSA-N 2-methyl-3-(3-methyldecan-2-yl)oxirane Chemical compound CCCCCCCC(C)C(C)C1OC1C IGMAMGCYKXBOJV-UHFFFAOYSA-N 0.000 description 1
RJCUNTCBNNWRMP-UHFFFAOYSA-N 2-methyloxirane Chemical compound CC1CO1.CC1CO1 RJCUNTCBNNWRMP-UHFFFAOYSA-N 0.000 description 1
IEZTZOYZNAATHP-UHFFFAOYSA-N 2-nonyl-3-undecyloxirane Chemical compound CCCCCCCCCCCC1OC1CCCCCCCCC IEZTZOYZNAATHP-UHFFFAOYSA-N 0.000 description 1
PMNLUUOXGOOLSP-UHFFFAOYSA-M 2-sulfanylpropanoate Chemical compound CC(S)C([O-])=O PMNLUUOXGOOLSP-UHFFFAOYSA-M 0.000 description 1
XGPXSKNQPJTMSR-UHFFFAOYSA-N 3,12-dibutyl-oxacyclotridecane Chemical compound CCCCC1CCCCCCCCC(CCCC)COC1 XGPXSKNQPJTMSR-UHFFFAOYSA-N 0.000 description 1
ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical compound OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 description 1
QZOIDDZFCPPBPM-UHFFFAOYSA-N 3-(2,2-dimethyltetradecyl)oxolane Chemical compound CCCCCCCCCCCCC(C)(C)CC1CCOC1 QZOIDDZFCPPBPM-UHFFFAOYSA-N 0.000 description 1
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
NDVLTZFQVDXFAN-UHFFFAOYSA-N 3-(2-cyanoethylsulfanyl)propanenitrile Chemical compound N#CCCSCCC#N NDVLTZFQVDXFAN-UHFFFAOYSA-N 0.000 description 1
DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 1
FCTXEFOUDMXDPD-UHFFFAOYSA-N 3-sulfanylpropanenitrile Chemical compound SCCC#N FCTXEFOUDMXDPD-UHFFFAOYSA-N 0.000 description 1
JNCIWKGAWRGVEN-UHFFFAOYSA-N 4-[hydroxy-(4-hydroxyphenyl)-phenylmethyl]phenol Chemical compound C1=CC(O)=CC=C1C(O)(C=1C=CC(O)=CC=1)C1=CC=CC=C1 JNCIWKGAWRGVEN-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
241000518994 Conta Species 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
239000004386 Erythritol Substances 0.000 description 1
UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
229920002176 Pluracol® Polymers 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
239000003490 Thiodipropionic acid Substances 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical class [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 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
239000000908 ammonium hydroxide Substances 0.000 description 1
229910001870 ammonium persulfate Inorganic materials 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
229920005601 base polymer Polymers 0.000 description 1
238000009835 boiling Methods 0.000 description 1
FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
IQOBTZHZLGMXBR-UHFFFAOYSA-N cyclododecane-1,3,8-triol Chemical compound OC1CCCCC(O)CC(O)CCCC1 IQOBTZHZLGMXBR-UHFFFAOYSA-N 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
UQLDLKMNUJERMK-UHFFFAOYSA-L di(octadecanoyloxy)lead Chemical class [Pb+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O UQLDLKMNUJERMK-UHFFFAOYSA-L 0.000 description 1
LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
239000000428 dust Substances 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
229940009714 erythritol Drugs 0.000 description 1
235000019414 erythritol Nutrition 0.000 description 1
PROQIPRRNZUXQM-ZXXIGWHRSA-N estriol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H]([C@H](O)C4)O)[C@@H]4[C@@H]3CCC2=C1 PROQIPRRNZUXQM-ZXXIGWHRSA-N 0.000 description 1
229960001348 estriol Drugs 0.000 description 1
239000012530 fluid Substances 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
238000001030 gas--liquid chromatography Methods 0.000 description 1
239000010438 granite Substances 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
150000002432 hydroperoxides Chemical class 0.000 description 1
239000011256 inorganic filler Substances 0.000 description 1
229910003475 inorganic filler Inorganic materials 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
239000011133 lead Substances 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
239000004579 marble Substances 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
OVALYCIUDYJCCC-UHFFFAOYSA-N naphthalene-1,4,5,8-tetrol Chemical compound C1=CC(O)=C2C(O)=CC=C(O)C2=C1O OVALYCIUDYJCCC-UHFFFAOYSA-N 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
INSIURULIZUZHA-UHFFFAOYSA-N oxacyclotridecane Chemical compound C1CCCCCCOCCCCC1 INSIURULIZUZHA-UHFFFAOYSA-N 0.000 description 1
AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
239000000047 product Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000004575 stone Substances 0.000 description 1
235000019303 thiodipropionic acid Nutrition 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000002023 wood Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
239000004246 zinc acetate Chemical class 0.000 description 1
229940098697 zinc laurate Drugs 0.000 description 1
GPYYEEJOMCKTPR-UHFFFAOYSA-L zinc;dodecanoate Chemical class [Zn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O GPYYEEJOMCKTPR-UHFFFAOYSA-L 0.000 description 1
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1

Landscapes

Sealing Material Composition (AREA)

CA000375060A 1981-04-09 1981-04-09 Composes de scellement Expired CA1159191A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000375060A CA1159191A (fr)	1981-04-09	1981-04-09	Composes de scellement

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000375060A CA1159191A (fr)	1981-04-09	1981-04-09	Composes de scellement

Publications (1)

Publication Number	Publication Date
CA1159191A true CA1159191A (fr)	1983-12-20

Family

ID=4119690

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000375060A Expired CA1159191A (fr)	1981-04-09	1981-04-09	Composes de scellement

Country Status (1)

Country	Link
CA (1)	CA1159191A (fr)

1981
- 1981-04-09 CA CA000375060A patent/CA1159191A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2000-12-20	MKEX	Expiry
2023-05-26	MKEX	Expiry	Effective date: 20001220

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US4906707A (en)	1990-03-06	Curable composition of oxyalkylene polymer
CA2050899C (fr)	2001-01-16	Composition polymerisable
JP2993778B2 (ja)	1999-12-27	室温硬化性組成物
WO1999048942A9 (fr)	2001-03-22	Polyurethane et preparation contenant du polyurethane
BRPI0617946A2 (pt)	2011-08-09	polìmero modificado por a-etoxissilano, processo para a preparação e uso do mesmo, composição endurecìvel, bem como uso da mesma
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JPWO1991013928A1 (ja)	1992-03-05	硬化性組成物
US3465057A (en)	1969-09-02	Curable ester compositions
DE69115811T2 (de)	1996-08-08	Härtbare Harzzusammensetzung
WO2009071548A1 (fr)	2009-06-11	Compositions durcissables contenant des polyuréthanes silylés
US4113707A (en)	1978-09-12	Poly(oxyalkylene)-polyester-poly(sulfide)-polythiol prepared by ester interchange
US4267307A (en)	1981-05-12	Sealant compositions
US3817936A (en)	1974-06-18	Poly(oxyalkylene)-polyester-polysulfide cross-linked polymers as sealants
US3850886A (en)	1974-11-26	Neutralized poly(oxyalkylene)-polyester-poly(monosulfide)-polythiol based sealants
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