CA1155250A - Oxygen-curable mercaptoorganosiloxane compositions catalyzed by metal carbonyl compounds and method of forming higher molecular weight products therefrom - Google Patents

Oxygen-curable mercaptoorganosiloxane compositions catalyzed by metal carbonyl compounds and method of forming higher molecular weight products therefrom

Info

Publication number: CA1155250A
Authority: CA; Canada
Prior art keywords: mercapto; inclusive; weight; functional; oxygen
Prior art date: 1979-12-03
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

CA000365275A

Other languages

English (en)

French (fr)

Inventor

Gary R. Homan

Chi-Long Lee

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.)

Dow Silicones Corp

Original Assignee

Dow Corning Corp

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.)

1979-12-03

Filing date

1980-11-21

Publication date

1983-10-11

1980-11-21 Application filed by Dow Corning Corp filed Critical Dow Corning Corp

1983-10-11 Application granted granted Critical

1983-10-11 Publication of CA1155250A publication Critical patent/CA1155250A/en

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 109
229910052751 metal Inorganic materials 0.000 title claims abstract description 25
239000002184 metal Substances 0.000 title claims abstract description 25
238000000034 method Methods 0.000 title claims description 27
150000001728 carbonyl compounds Chemical class 0.000 title abstract description 9
239000003054 catalyst Substances 0.000 claims abstract description 45
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 34
239000001301 oxygen Substances 0.000 claims abstract description 34
229910052760 oxygen Inorganic materials 0.000 claims abstract description 34
239000000945 filler Substances 0.000 claims abstract description 23
125000005375 organosiloxane group Chemical group 0.000 claims abstract description 22
238000002156 mixing Methods 0.000 claims abstract description 10
230000003197 catalytic effect Effects 0.000 claims abstract description 8
GXQCGPVEDZFCGW-UHFFFAOYSA-N 2,3-dihydro-1h-pyrrolo[3,4-c]pyridine;dihydrochloride Chemical group Cl.Cl.N1=CC=C2CNCC2=C1 GXQCGPVEDZFCGW-UHFFFAOYSA-N 0.000 claims abstract description 6
NBFCJULAAWWTBL-UHFFFAOYSA-N buta-1,3-diene;carbon monoxide;iron Chemical group [Fe].[O+]#[C-].[O+]#[C-].[O+]#[C-].C=CC=C NBFCJULAAWWTBL-UHFFFAOYSA-N 0.000 claims abstract description 5
125000004989 dicarbonyl group Chemical group 0.000 claims abstract description 5
ANHQLUBMNSSPBV-UHFFFAOYSA-N 4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical group C1=CN=C2NC(=O)COC2=C1 ANHQLUBMNSSPBV-UHFFFAOYSA-N 0.000 claims abstract description 4
229910016660 Mn2(CO)10 Inorganic materials 0.000 claims abstract description 4
QFEOTYVTTQCYAZ-UHFFFAOYSA-N dimanganese decacarbonyl Chemical compound [Mn].[Mn].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] QFEOTYVTTQCYAZ-UHFFFAOYSA-N 0.000 claims abstract description 4
229910017147 Fe(CO)5 Inorganic materials 0.000 claims abstract 5
-1 siloxane units Chemical group 0.000 claims description 103
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 7
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 6
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical group [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract description 35
239000000565 sealant Substances 0.000 abstract description 16
229920005989 resin Polymers 0.000 abstract description 13
239000011347 resin Substances 0.000 abstract description 13
239000000499 gel Substances 0.000 abstract description 9
238000000576 coating method Methods 0.000 abstract description 5
125000001424 substituent group Chemical group 0.000 abstract description 5
239000011248 coating agent Substances 0.000 abstract description 3
229940087654 iron carbonyl Drugs 0.000 abstract description 3
239000000047 product Substances 0.000 description 29
125000003396 thiol group Chemical group [H]S* 0.000 description 29
229920000642 polymer Polymers 0.000 description 24
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
125000004122 cyclic group Chemical group 0.000 description 14
229920001971 elastomer Polymers 0.000 description 14
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 12
239000000806 elastomer Substances 0.000 description 12
150000001875 compounds Chemical class 0.000 description 11
239000004205 dimethyl polysiloxane Substances 0.000 description 11
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
229910052742 iron Inorganic materials 0.000 description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
238000009472 formulation Methods 0.000 description 9
238000006116 polymerization reaction Methods 0.000 description 8
239000012530 fluid Substances 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
229910000019 calcium carbonate Inorganic materials 0.000 description 6
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical group [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000000377 silicon dioxide Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000000758 substrate Substances 0.000 description 6
229920001577 copolymer Polymers 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
230000000704 physical effect Effects 0.000 description 5
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 5
IKYAJDOSWUATPI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propane-1-thiol Chemical group CO[Si](C)(OC)CCCS IKYAJDOSWUATPI-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
230000007246 mechanism Effects 0.000 description 4
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
229910052753 mercury Inorganic materials 0.000 description 4
239000002480 mineral oil Substances 0.000 description 4
235000010446 mineral oil Nutrition 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
239000012763 reinforcing filler Substances 0.000 description 4
238000003860 storage Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 3
239000005909 Kieselgur Substances 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
239000000654 additive Substances 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
229910001873 dinitrogen Inorganic materials 0.000 description 3
238000004821 distillation Methods 0.000 description 3
239000003517 fume Substances 0.000 description 3
229920001002 functional polymer Polymers 0.000 description 3
239000010410 layer Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000011253 protective coating Substances 0.000 description 3
238000010926 purge Methods 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
229920002554 vinyl polymer Polymers 0.000 description 3
229910002012 Aerosil® Inorganic materials 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000008901 benefit Effects 0.000 description 2
150000001721 carbon Chemical class 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
SKWRXFAMSFJQRS-UHFFFAOYSA-N carbon monoxide;cobalt Chemical compound [Co].[O+]#[C-].[O+]#[C-] SKWRXFAMSFJQRS-UHFFFAOYSA-N 0.000 description 2
230000008859 change Effects 0.000 description 2
239000010941 cobalt Substances 0.000 description 2
229910017052 cobalt Inorganic materials 0.000 description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
238000001723 curing Methods 0.000 description 2
ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
229910001882 dioxygen Inorganic materials 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 2
125000005358 mercaptoalkyl group Chemical group 0.000 description 2
150000002816 nickel compounds Chemical class 0.000 description 2
150000002894 organic compounds Chemical class 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
230000000379 polymerizing effect Effects 0.000 description 2
229920001296 polysiloxane Polymers 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000005060 rubber Substances 0.000 description 2
150000004756 silanes Chemical class 0.000 description 2
229910052710 silicon Inorganic materials 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
102100024133 Coiled-coil domain-containing protein 50 Human genes 0.000 description 1
229920001875 Ebonite Polymers 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
101000910772 Homo sapiens Coiled-coil domain-containing protein 50 Proteins 0.000 description 1
229910018382 Mn(CO)3 Inorganic materials 0.000 description 1
YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
229910018540 Si C Inorganic materials 0.000 description 1
229910004674 SiO0.5 Inorganic materials 0.000 description 1
108091093126 WHP Posttrascriptional Response Element Proteins 0.000 description 1
DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
LVAXPOVMRMFJSK-UHFFFAOYSA-N [Na].OS(=O)=O Chemical compound [Na].OS(=O)=O LVAXPOVMRMFJSK-UHFFFAOYSA-N 0.000 description 1
230000009471 action Effects 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
238000013459 approach Methods 0.000 description 1
150000005840 aryl radicals Chemical group 0.000 description 1
239000010425 asbestos Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
239000012965 benzophenone Substances 0.000 description 1
AXYSDZQJEIAXBL-UHFFFAOYSA-N bis(oxomethylidene)iron Chemical compound O=C=[Fe]=C=O AXYSDZQJEIAXBL-UHFFFAOYSA-N 0.000 description 1
235000008429 bread Nutrition 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
235000015115 caffè latte Nutrition 0.000 description 1
BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000004927 clay Substances 0.000 description 1
229910052570 clay Inorganic materials 0.000 description 1
238000004040 coloring Methods 0.000 description 1
238000010276 construction Methods 0.000 description 1
238000013036 cure process Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
UCJHMXXKIKBHQP-UHFFFAOYSA-N dichloro-(3-chloropropyl)-methylsilane Chemical compound C[Si](Cl)(Cl)CCCCl UCJHMXXKIKBHQP-UHFFFAOYSA-N 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
238000010894 electron beam technology Methods 0.000 description 1
239000008393 encapsulating agent Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000001879 gelation Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
229920000578 graft copolymer Polymers 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
150000002432 hydroperoxides Chemical class 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000003801 milling Methods 0.000 description 1
238000013008 moisture curing Methods 0.000 description 1
229940094933 n-dodecane Drugs 0.000 description 1
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
230000009972 noncorrosive effect Effects 0.000 description 1
HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
IALUUOKJPBOFJL-UHFFFAOYSA-N potassium oxidosilane Chemical compound [K+].[SiH3][O-] IALUUOKJPBOFJL-UHFFFAOYSA-N 0.000 description 1
230000002028 premature Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000010453 quartz Substances 0.000 description 1
230000005855 radiation Effects 0.000 description 1
238000003847 radiation curing Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
229910010271 silicon carbide Inorganic materials 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000002344 surface layer Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
238000012360 testing method Methods 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
238000004448 titration Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000009423 ventilation Methods 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- A—HUMAN NECESSITIES
- A44—HABERDASHERY; JEWELLERY
- A44C—PERSONAL ADORNMENTS, e.g. JEWELLERY; COINS
- A44C5/00—Bracelets; Wrist-watch straps; Fastenings for bracelets or wrist-watch straps
- A44C5/18—Fasteners for straps, chains or the like
- A44C5/20—Fasteners for straps, chains or the like for open straps, chains or the like
- A—HUMAN NECESSITIES
- A44—HABERDASHERY; JEWELLERY
- A44C—PERSONAL ADORNMENTS, e.g. JEWELLERY; COINS
- A44C5/00—Bracelets; Wrist-watch straps; Fastenings for bracelets or wrist-watch straps
- A44C5/18—Fasteners for straps, chains or the like
- A44C5/20—Fasteners for straps, chains or the like for open straps, chains or the like
- A44C5/2019—Hooks
- A44C5/2023—Sliding hooks
- A44C5/2028—Sliding hooks with spring closure means
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Compositions Of Macromolecular Compounds (AREA)
Silicon Polymers (AREA)
Adornments (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)

CA000365275A 1979-12-03 1980-11-21 Oxygen-curable mercaptoorganosiloxane compositions catalyzed by metal carbonyl compounds and method of forming higher molecular weight products therefrom Expired CA1155250A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US099,252		1979-12-03
US06/099,252 US4252932A (en)	1979-12-03	1979-12-03	Oxygen-curable mercaptoorganosiloxane compositions catalyzed by metal carbonyl compounds and method of forming higher molecular weight products therefrom

Publications (1)

Publication Number	Publication Date
CA1155250A true CA1155250A (en)	1983-10-11

Family

ID=22273918

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000365275A Expired CA1155250A (en)	1979-12-03	1980-11-21	Oxygen-curable mercaptoorganosiloxane compositions catalyzed by metal carbonyl compounds and method of forming higher molecular weight products therefrom

Country Status (10)

Country	Link
US (1)	US4252932A (2)
EP (1)	EP0030155B1 (2)
JP (2)	JPS604217B2 (2)
BR (1)	BR8008945A (2)
CA (1)	CA1155250A (2)
DD (1)	DD154995A5 (2)
DE (1)	DE3067047D1 (2)
ES (1)	ES497367A0 (2)
WO (1)	WO1981001565A1 (2)
ZA (1)	ZA807548B (2)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4526954A (en) *	1983-12-28	1985-07-02	Union Carbide Corporation	Organosiloxane polymers and compositions containing same curable upon exposure to gaseous oxygen
US5015717A (en) *	1986-12-22	1991-05-14	Wacker Silicones Corporation	Sulfur-containing organopolysiloxane waxes and a method for preparing the same
JPH01313565A (ja) *	1988-06-10	1989-12-19	Toray Dow Corning Silicone Co Ltd	硬化性オルガノポリシロキサン組成物
US5994456A (en) *	1998-04-09	1999-11-30	Dow Corning Corporation	Compositions comprising mercapto-functional organosilicon compounds
US6632674B1 (en)	1999-03-31	2003-10-14	Industrial Scientific Corporation	Method of testing gas detection instruments and associated apparatus
DE102012004132A1 (de) *	2012-02-29	2013-08-29	Friedrich-Schiller-Universität Jena	Kohlenstoffmonoxid freisetzende Materialien und deren Verwendung
JP7573232B2 (ja)	2020-07-06	2024-10-25	日本表面化学株式会社	化成処理用金属着色液及び金属着色処理方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3445419A (en) *	1966-01-21	1969-05-20	Dow Corning	Room temperature vulcanizable silicones
US4066603A (en) *	1976-03-03	1978-01-03	Dow Corning Corporation	Sulfur containing silicone elastomer and method of preparation
US4151156A (en) *	1976-07-22	1979-04-24	Shin-Etsu Chemical Co., Ltd.	Mercapto group-containing silicone rubber compositions
US4070329A (en) *	1977-01-03	1978-01-24	Dow Corning Corporation	Siloxane elastomer prepared from mercaptoorg anopolysiloxanes
US4070328A (en) *	1977-01-03	1978-01-24	Dow Corning Corporation	Mercaptoorganopolysiloxanes cured to elastomers with peroxides and nitrogen compounds
US4133939A (en) *	1977-12-16	1979-01-09	Dow Corning Corporation	Method for applying a silicone release coating and coated article therefrom

1979
- 1979-12-03 US US06/099,252 patent/US4252932A/en not_active Expired - Lifetime
1980
- 1980-11-21 CA CA000365275A patent/CA1155250A/en not_active Expired
- 1980-11-24 WO PCT/US1980/001598 patent/WO1981001565A1/en not_active Ceased
- 1980-11-24 BR BR8008945A patent/BR8008945A/pt unknown
- 1980-11-24 JP JP81500346A patent/JPS604217B2/ja not_active Expired
- 1980-11-24 JP JP81500344A patent/JPS56501611A/ja active Granted
- 1980-12-02 DE DE8080304330T patent/DE3067047D1/de not_active Expired
- 1980-12-02 ES ES497367A patent/ES497367A0/es active Granted
- 1980-12-02 EP EP80304330A patent/EP0030155B1/en not_active Expired
- 1980-12-03 ZA ZA00807548A patent/ZA807548B/xx unknown
- 1980-12-03 DD DD80225688A patent/DD154995A5/de unknown

Also Published As

Publication number	Publication date
EP0030155A1 (en)	1981-06-10
EP0030155B1 (en)	1984-03-14
WO1981001565A1 (en)	1981-06-11
DD154995A5 (de)	1982-05-05
ES8303477A1 (es)	1983-02-01
BR8008945A (pt)	1981-10-20
DE3067047D1 (en)	1984-04-19
JPS604217B2 (ja)	1985-02-02
US4252932A (en)	1981-02-24
ES497367A0 (es)	1983-02-01
JPS55501089A (2)	1980-12-11
ZA807548B (en)	1981-11-25
JPS56501611A (2)	1981-11-05

Legal Events

Date	Code	Title	Description
2000-10-11	MKEX	Expiry

Publication	Publication Date	Title
KR0135282B1 (ko)	1998-04-22	슬럼프가 없는 투명한 실리콘 봉함재
US4652624A (en)	1987-03-24	Room-temperature-curing silicone sealants
CA1067641A (en)	1979-12-04	Sulfur containing silicone elastomer and method of preparation
US5081172A (en)	1992-01-14	Method to reduce compression set in silanol-containing silicone elastomer bases
US4355121A (en)	1982-10-19	Heat strength curable silicone rubber compositions
EP0361803A2 (en)	1990-04-04	In situ formed titanium chelate catalysts
CA1151339A (en)	1983-08-02	Oxygen-curable mercaptoorganosiloxane compositions possessing rapid surface reaction and method of forming higher molecular weight products therefrom
CA1155250A (en)	1983-10-11	Oxygen-curable mercaptoorganosiloxane compositions catalyzed by metal carbonyl compounds and method of forming higher molecular weight products therefrom
US4239674A (en)	1980-12-16	Oxygen-curable mercaptoorganosiloxane compositions catalyzed by cobaltocene compounds and method of forming higher molecular weight products therefrom
EP0041558B1 (en)	1984-07-04	Oxygen-curable mercaptoorganosiloxane compositions containing both redox and iron carbonyl compounds and method of forming higher molecular weight products therefrom
US5994456A (en)	1999-11-30	Compositions comprising mercapto-functional organosilicon compounds
EP0030801B1 (en)	1984-03-07	Ferrocene catalyzed elastomer formation
US4292422A (en)	1981-09-29	Oxygen-curable mercapto-functional organosilicon-organic compound compositions catalyzed by metal carbonyl compounds and method of forming higher molecular weight products therefrom
US4267296A (en)	1981-05-12	Oxygen-curable mercapto-functional organosilicon-organic compound compositions possessing rapid surface reaction and method of forming higher molecular weight products therefrom
JPH02187488A (ja)	1990-07-23	急速硬化中性シリコーンシーラント
JPS603424B2 (ja)	1985-01-28	メルカプトオルガノポリシロキサンおよびカルボン酸の金属塩を含有する組成物