AU622451B2 – Room temperature curable organopolysiloxane composition
– Google Patents
AU622451B2 – Room temperature curable organopolysiloxane composition
– Google Patents
Room temperature curable organopolysiloxane composition
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Info
Publication number
AU622451B2
AU622451B2
AU35875/89A
AU3587589A
AU622451B2
AU 622451 B2
AU622451 B2
AU 622451B2
AU 35875/89 A
AU35875/89 A
AU 35875/89A
AU 3587589 A
AU3587589 A
AU 3587589A
AU 622451 B2
AU622451 B2
AU 622451B2
Authority
AU
Australia
Prior art keywords
room temperature
group
groups
monovalent hydrocarbon
weight parts
Prior art date
1988-06-02
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.)
Ceased
Application number
AU35875/89A
Other versions
AU3587589A
(en
Inventor
Miyoji Fukayama
Masayuki Onishi
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.)
DuPont Toray Specialty Materials KK
Original Assignee
Toray Silicone Co Ltd
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.)
1988-06-02
Filing date
1989-06-01
Publication date
1992-04-09
1989-06-01
Application filed by Toray Silicone Co Ltd
filed
Critical
Toray Silicone Co Ltd
1989-12-07
Publication of AU3587589A
publication
Critical
patent/AU3587589A/en
1992-04-09
Application granted
granted
Critical
1992-04-09
Publication of AU622451B2
publication
Critical
patent/AU622451B2/en
2009-06-01
Anticipated expiration
legal-status
Critical
Status
Ceased
legal-status
Critical
Current
Links
Espacenet
Global Dossier
Discuss
229920001296
polysiloxane
Polymers
0.000
title
claims
description
45
239000000203
mixture
Substances
0.000
title
claims
description
44
125000001183
hydrocarbyl group
Chemical group
0.000
claims
description
30
239000003054
catalyst
Substances
0.000
claims
description
10
230000007062
hydrolysis
Effects
0.000
claims
description
8
238000006460
hydrolysis reaction
Methods
0.000
claims
description
8
125000003396
thiol group
Chemical group
[H]S*
0.000
claims
description
8
UUEWCQRISZBELL-UHFFFAOYSA-N
3-trimethoxysilylpropane-1-thiol
Chemical group
CO[Si](OC)(OC)CCCS
UUEWCQRISZBELL-UHFFFAOYSA-N
0.000
claims
description
6
125000003545
alkoxy group
Chemical group
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claims
description
6
125000004430
oxygen atom
Chemical group
O*
0.000
claims
description
5
229910009257
Y—Si
Inorganic materials
0.000
claims
description
4
125000004966
cyanoalkyl group
Chemical group
0.000
claims
description
4
150000008282
halocarbons
Chemical group
0.000
claims
description
4
125000000962
organic group
Chemical group
0.000
claims
description
4
150000001282
organosilanes
Chemical class
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claims
description
3
210000002837
heart atrium
Anatomy
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claims
1
-1
chloropropyl
Chemical group
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description
15
239000000758
substrate
Substances
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description
13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N
silicon dioxide
Inorganic materials
O=[Si]=O
VYPSYNLAJGMNEJ-UHFFFAOYSA-N
0.000
description
10
238000000034
method
Methods
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description
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VTYYLEPIZMXCLO-UHFFFAOYSA-L
Calcium carbonate
Chemical compound
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VTYYLEPIZMXCLO-UHFFFAOYSA-L
0.000
description
6
RTAQQCXQSZGOHL-UHFFFAOYSA-N
Titanium
Chemical compound
[Ti]
RTAQQCXQSZGOHL-UHFFFAOYSA-N
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description
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238000006482
condensation reaction
Methods
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description
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titanium
Substances
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titanium
Inorganic materials
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description
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metal
Inorganic materials
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description
5
239000002184
metal
Substances
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silane
Inorganic materials
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description
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238000012360
testing method
Methods
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IKYAJDOSWUATPI-UHFFFAOYSA-N
3-[dimethoxy(methyl)silyl]propane-1-thiol
Chemical compound
CO[Si](C)(OC)CCCS
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0.000
description
4
BLRPTPMANUNPDV-UHFFFAOYSA-N
Silane
Chemical compound
[SiH4]
BLRPTPMANUNPDV-UHFFFAOYSA-N
0.000
description
4
239000004205
dimethyl polysiloxane
Substances
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description
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235000013870
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Nutrition
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description
4
229940093858
ethyl acetoacetate
Drugs
0.000
description
4
FFUAGWLWBBFQJT-UHFFFAOYSA-N
hexamethyldisilazane
Chemical compound
C[Si](C)(C)N[Si](C)(C)C
FFUAGWLWBBFQJT-UHFFFAOYSA-N
0.000
description
4
238000005259
measurement
Methods
0.000
description
4
125000002496
methyl group
Chemical group
[H]C([H])([H])*
0.000
description
4
BFXIKLCIZHOAAZ-UHFFFAOYSA-N
methyltrimethoxysilane
Chemical compound
CO[Si](C)(OC)OC
BFXIKLCIZHOAAZ-UHFFFAOYSA-N
0.000
description
4
229920000435
poly(dimethylsiloxane)
Polymers
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description
4
239000000377
silicon dioxide
Substances
0.000
description
4
239000000853
adhesive
Substances
0.000
description
3
230000001070
adhesive effect
Effects
0.000
description
3
125000000217
alkyl group
Chemical group
0.000
description
3
229910052782
aluminium
Inorganic materials
0.000
description
3
XAGFODPZIPBFFR-UHFFFAOYSA-N
aluminium
Chemical compound
[Al]
XAGFODPZIPBFFR-UHFFFAOYSA-N
0.000
description
3
WPPDFTBPZNZZRP-UHFFFAOYSA-N
aluminum copper
Chemical compound
[Al].[Cu]
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0.000
description
3
230000015572
biosynthetic process
Effects
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description
3
229910000019
calcium carbonate
Inorganic materials
0.000
description
3
238000000576
coating method
Methods
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description
3
229920001971
elastomer
Polymers
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description
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elastomer
Substances
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description
3
239000003822
epoxy resin
Substances
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description
3
XYIBRDXRRQCHLP-UHFFFAOYSA-N
ethyl acetoacetate
Chemical compound
CCOC(=O)CC(C)=O
XYIBRDXRRQCHLP-UHFFFAOYSA-N
0.000
description
3
125000001495
ethyl group
Chemical group
[H]C([H])([H])C([H])([H])*
0.000
description
3
239000011521
glass
Substances
0.000
description
3
238000002156
mixing
Methods
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3
125000002347
octyl group
Chemical group
[H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]
0.000
description
3
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Polymers
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description
3
239000004431
polycarbonate resin
Substances
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description
3
229920000647
polyepoxide
Polymers
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description
3
125000001436
propyl group
Chemical group
[H]C([*])([H])C([H])([H])C([H])([H])[H]
0.000
description
3
238000010992
reflux
Methods
0.000
description
3
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sealant
Substances
0.000
description
3
238000003786
synthesis reaction
Methods
0.000
description
3
BSKHPKMHTQYZBB-UHFFFAOYSA-N
2-methylpyridine
Chemical compound
CC1=CC=CC=N1
BSKHPKMHTQYZBB-UHFFFAOYSA-N
0.000
description
2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N
Ethanol
Chemical compound
CCO
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0.000
description
2
XEEYBQQBJWHFJM-UHFFFAOYSA-N
Iron
Chemical compound
[Fe]
XEEYBQQBJWHFJM-UHFFFAOYSA-N
0.000
description
2
CPLXHLVBOLITMK-UHFFFAOYSA-N
Magnesium oxide
Chemical compound
[Mg]=O
CPLXHLVBOLITMK-UHFFFAOYSA-N
0.000
description
2
JUJWROOIHBZHMG-UHFFFAOYSA-N
Pyridine
Chemical compound
C1=CC=NC=C1
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0.000
description
2
ATJFFYVFTNAWJD-UHFFFAOYSA-N
Tin
Chemical compound
[Sn]
ATJFFYVFTNAWJD-UHFFFAOYSA-N
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
YRKCREAYFQTBPV-UHFFFAOYSA-N
acetylacetone
Chemical compound
CC(=O)CC(C)=O
YRKCREAYFQTBPV-UHFFFAOYSA-N
0.000
description
2
238000007259
addition reaction
Methods
0.000
description
2
230000032683
aging
Effects
0.000
description
2
125000003342
alkenyl group
Chemical group
0.000
description
2
125000002947
alkylene group
Chemical group
0.000
description
2
239000011230
binding agent
Substances
0.000
description
2
YHWCPXVTRSHPNY-UHFFFAOYSA-N
butan-1-olate;titanium(4+)
Chemical compound
[Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-]
YHWCPXVTRSHPNY-UHFFFAOYSA-N
0.000
description
2
125000000484
butyl group
Chemical group
[H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H]
0.000
description
2
150000001735
carboxylic acids
Chemical class
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description
2
238000006243
chemical reaction
Methods
0.000
description
2
239000011248
coating agent
Substances
0.000
description
2
KPUWHANPEXNPJT-UHFFFAOYSA-N
disiloxane
Chemical compound
[SiH3]O[SiH3]
KPUWHANPEXNPJT-UHFFFAOYSA-N
0.000
description
2
NKSJNEHGWDZZQF-UHFFFAOYSA-N
ethenyl(trimethoxy)silane
Chemical compound
CO[Si](OC)(OC)C=C
NKSJNEHGWDZZQF-UHFFFAOYSA-N
0.000
description
2
125000004051
hexyl group
Chemical group
[H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])*
0.000
description
2
239000012433
hydrogen halide
Substances
0.000
description
2
229910000039
hydrogen halide
Inorganic materials
0.000
description
2
239000011256
inorganic filler
Substances
0.000
description
2
229910003475
inorganic filler
Inorganic materials
0.000
description
2
125000001997
phenyl group
Chemical group
[H]C1=C([H])C([H])=C(*)C([H])=C1[H]
0.000
description
2
239000004033
plastic
Substances
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description
2
229920003023
plastic
Polymers
0.000
description
2
BASFCYQUMIYNBI-UHFFFAOYSA-N
platinum
Chemical compound
[Pt]
BASFCYQUMIYNBI-UHFFFAOYSA-N
0.000
description
2
239000000126
substance
Substances
0.000
description
2
229910052718
tin
Inorganic materials
0.000
description
2
VXUYXOFXAQZZMF-UHFFFAOYSA-N
titanium(IV) isopropoxide
Chemical compound
CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C
VXUYXOFXAQZZMF-UHFFFAOYSA-N
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
XNWFRZJHXBZDAG-UHFFFAOYSA-N
2-METHOXYETHANOL
Chemical compound
COCCO
XNWFRZJHXBZDAG-UHFFFAOYSA-N
0.000
description
1
125000003903
2-propenyl group
Chemical group
[H]C([*])([H])C([H])=C([H])[H]
0.000
description
1
DCQBZYNUSLHVJC-UHFFFAOYSA-N
3-triethoxysilylpropane-1-thiol
Chemical compound
CCO[Si](OCC)(OCC)CCCS
DCQBZYNUSLHVJC-UHFFFAOYSA-N
0.000
description
1
238000004438
BET method
Methods
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description
1
OTCOSAMIXUWQOA-UHFFFAOYSA-N
COC(OC)(OC)CO[SiH2]C
Chemical compound
COC(OC)(OC)CO[SiH2]C
OTCOSAMIXUWQOA-UHFFFAOYSA-N
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description
1
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Chlorosilane
Substances
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description
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Cross linker
Substances
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Kieselgur
Substances
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description
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BPQQTUXANYXVAA-UHFFFAOYSA-N
Orthosilicate
Chemical compound
[O-][Si]([O-])([O-])[O-]
BPQQTUXANYXVAA-UHFFFAOYSA-N
0.000
description
1
BOTDANWDWHJENH-UHFFFAOYSA-N
Tetraethyl orthosilicate
Chemical compound
CCO[Si](OCC)(OCC)OCC
BOTDANWDWHJENH-UHFFFAOYSA-N
0.000
description
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HCHKCACWOHOZIP-UHFFFAOYSA-N
Zinc
Chemical compound
[Zn]
HCHKCACWOHOZIP-UHFFFAOYSA-N
0.000
description
1
FMRLDPWIRHBCCC-UHFFFAOYSA-L
Zinc carbonate
Chemical compound
[Zn+2].[O-]C([O-])=O
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0.000
description
1
QCWXUUIWCKQGHC-UHFFFAOYSA-N
Zirconium
Chemical compound
[Zr]
QCWXUUIWCKQGHC-UHFFFAOYSA-N
0.000
description
1
UKLDJPRMSDWDSL-UHFFFAOYSA-L
[dibutyl(dodecanoyloxy)stannyl] dodecanoate
Chemical compound
CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC
UKLDJPRMSDWDSL-UHFFFAOYSA-L
0.000
description
1
NBJODVYWAQLZOC-UHFFFAOYSA-L
[dibutyl(octanoyloxy)stannyl] octanoate
Chemical compound
CCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCC
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description
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Substances
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alkoxy alkyl group
Chemical group
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description
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aluminium hydroxide
Chemical compound
[OH-].[OH-].[OH-].[Al+3]
WNROFYMDJYEPJX-UHFFFAOYSA-K
0.000
description
1
PNEYBMLMFCGWSK-UHFFFAOYSA-N
aluminium oxide
Inorganic materials
[O-2].[O-2].[O-2].[Al+3].[Al+3]
PNEYBMLMFCGWSK-UHFFFAOYSA-N
0.000
description
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amines
Chemical class
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description
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antimony
Inorganic materials
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description
1
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antimony atom
Chemical compound
[Sb]
WATWJIUSRGPENY-UHFFFAOYSA-N
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aryl alkyl group
Chemical group
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aryl group
Chemical group
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bead
Substances
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benzyl group
Chemical group
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description
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229910052797
bismuth
Inorganic materials
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description
1
JCXGWMGPZLAOME-UHFFFAOYSA-N
bismuth atom
Chemical compound
[Bi]
JCXGWMGPZLAOME-UHFFFAOYSA-N
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calcium
Substances
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carbon atom
Chemical group
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Substances
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Chemical group
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chlorosilane
Chemical compound
Cl[SiH3]
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compounds
Chemical class
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compromised effect
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condensation
Methods
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condensation
Effects
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construction
Methods
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Chemical group
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cycloalkyl group
Chemical group
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cyclohexyl group
Chemical group
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cyclopentyl group
Chemical group
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decyl group
Chemical group
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dibutyltin dilaurate
Substances
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difluorophenyl group
Chemical group
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description
1
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dimethoxy(dimethyl)silane
Chemical compound
CO[Si](C)(C)OC
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0.000
description
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AHUXYBVKTIBBJW-UHFFFAOYSA-N
dimethoxy(diphenyl)silane
Chemical compound
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Polymers
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esters
Chemical class
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ethenyl-tris(prop-1-en-2-yloxy)silane
Chemical compound
CC(=C)O[Si](OC(C)=C)(OC(C)=C)C=C
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Chemical group
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0.000
description
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ethyl(trimethoxy)silane
Chemical compound
CC[Si](OC)(OC)OC
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Substances
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Proteins
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halogen
Inorganic materials
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description
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halogens
Chemical class
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heat treatment
Methods
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iron
Inorganic materials
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description
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159000000014
iron salts
Chemical class
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description
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239000000395
magnesium oxide
Substances
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manganese
Chemical class
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material
Substances
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metals
Chemical class
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ZWXYOPPJTRVTST-UHFFFAOYSA-N
methyl-tris(prop-1-en-2-yloxy)silane
Chemical compound
CC(=C)O[Si](C)(OC(C)=C)OC(C)=C
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Methods
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naphthyl group
Chemical group
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odor
Nutrition
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organic acids
Chemical class
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description
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organic acids
Nutrition
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organic compounds
Chemical class
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description
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organic solvent
Substances
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Substances
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description
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XGIZTLFJCDBRDD-UHFFFAOYSA-N
phenyl-tris(prop-1-en-2-yloxy)silane
Chemical compound
CC(=C)O[Si](OC(C)=C)(OC(C)=C)C1=CC=CC=C1
XGIZTLFJCDBRDD-UHFFFAOYSA-N
0.000
description
1
125000000286
phenylethyl group
Chemical group
[H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])*
0.000
description
1
125000004344
phenylpropyl group
Chemical group
0.000
description
1
239000004014
plasticizer
Substances
0.000
description
1
229910052697
platinum
Inorganic materials
0.000
description
1
238000006116
polymerization reaction
Methods
0.000
description
1
239000000843
powder
Substances
0.000
description
1
238000002360
preparation method
Methods
0.000
description
1
UMJSCPRVCHMLSP-UHFFFAOYSA-N
pyridine
Natural products
COC1=CC=CN=C1
UMJSCPRVCHMLSP-UHFFFAOYSA-N
0.000
description
1
239000010453
quartz
Substances
0.000
description
1
239000011541
reaction mixture
Substances
0.000
description
1
238000011160
research
Methods
0.000
description
1
150000003839
salts
Chemical class
0.000
description
1
125000005372
silanol group
Chemical group
0.000
description
1
125000004079
stearyl group
Chemical group
[H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]
0.000
description
1
238000004381
surface treatment
Methods
0.000
description
1
150000003512
tertiary amines
Chemical class
0.000
description
1
XNDVYJMKIJRDPF-UHFFFAOYSA-N
tetrakis(prop-1-en-2-yl) silicate
Chemical compound
CC(=C)O[Si](OC(C)=C)(OC(C)=C)OC(C)=C
XNDVYJMKIJRDPF-UHFFFAOYSA-N
0.000
description
1
LFQCEHFDDXELDD-UHFFFAOYSA-N
tetramethyl orthosilicate
Chemical compound
CO[Si](OC)(OC)OC
LFQCEHFDDXELDD-UHFFFAOYSA-N
0.000
description
1
238000003878
thermal aging
Methods
0.000
description
1
239000013008
thixotropic agent
Substances
0.000
description
1
239000011135
tin
Substances
0.000
description
1
150000003606
tin compounds
Chemical class
0.000
description
1
KSBAEPSJVUENNK-UHFFFAOYSA-L
tin(ii) 2-ethylhexanoate
Chemical compound
[Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O
KSBAEPSJVUENNK-UHFFFAOYSA-L
0.000
description
1
150000003609
titanium compounds
Chemical class
0.000
description
1
239000004408
titanium dioxide
Substances
0.000
description
1
125000003944
tolyl group
Chemical group
0.000
description
1
CPUDPFPXCZDNGI-UHFFFAOYSA-N
triethoxy(methyl)silane
Chemical compound
CCO[Si](C)(OCC)OCC
CPUDPFPXCZDNGI-UHFFFAOYSA-N
0.000
description
1
125000002023
trifluoromethyl group
Chemical group
FC(F)(F)*
0.000
description
1
ZNOCGWVLWPVKAO-UHFFFAOYSA-N
trimethoxy(phenyl)silane
Chemical compound
CO[Si](OC)(OC)C1=CC=CC=C1
ZNOCGWVLWPVKAO-UHFFFAOYSA-N
0.000
description
1
LAAPHJLUTMQYKC-UHFFFAOYSA-N
tris(ethenoxy)-methylsilane
Chemical compound
C=CO[Si](C)(OC=C)OC=C
LAAPHJLUTMQYKC-UHFFFAOYSA-N
0.000
description
1
229910052725
zinc
Inorganic materials
0.000
description
1
239000011701
zinc
Substances
0.000
description
1
239000011667
zinc carbonate
Substances
0.000
description
1
229910000010
zinc carbonate
Inorganic materials
0.000
description
1
235000004416
zinc carbonate
Nutrition
0.000
description
1
239000011787
zinc oxide
Substances
0.000
description
1
229910052726
zirconium
Inorganic materials
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
C08K5/00—Use of organic ingredients
C08K5/54—Silicon-containing compounds
C08K5/5406—Silicon-containing compounds containing elements other than oxygen or nitrogen
Description
4. The basic application referred to in paragraph 2 of this Declaration first application made in a Convention country in respect of the invention the subject of the application.
DECLARED day of.
Ma r 10 Q ‘1’ffl V cTT ‘PAMVt T.TMTTED COMMONWEALTH OF AUSTRALIA 6 2 2 4 PATENTS ACT 1952-69 COMPLETE SPECIFICATION
(ORIGINAL)
Class Int. Class Application Number: Lodged: Complete Specification Lodged: Accepted: Published: -Piriority 0 0 Related Art: o ‘6 0 Name of Applicant: Address of Applicant: TORAY SILICONE COMPANY, LTD.
3-16, 2-chome, Nihonbashi-Muromachi, Chuo-Ku, Tokyo, Japan MASAYUKI ONISHI and MIYOJI FUKAYAMA Actual Inventor: o 6 Address for Service: ‘-WW -Watermark Patent Trademark Attorneys 50 QUEEN STREET, MELBOURNE, AUSTRALIA, 3000.
Complete Specification for the invention entitled: ROOM TEMPERATURE CURABLE ORGANOPOLYSILOXANE COMPOSITION i S The following statement is a full description of this invention, including the best method of performing it known to us 1.
I
I
A:
I 4
_JI
ROOM TEMPERATURE-CURABLE ORGANOPOLYSILOXANE COMPOSITION The present invention relates to a room temperature-curable organopolysiloxane composition, and, more particularly, relates to a room temperature-curable organopolysiloxane composition which evidences an S excellent adLiesion for various and diverse substrates while having an excellent storage stability under seal.
o Various types of room temperature-curable o organopolysiloxane compositions which cure to the elastomer at room temperature upon contact with ao atmospheric moisture are already familiar to the art.
Above all, because they are not accompanied by disagreeable odors and do not corrode metal with which they may be in contact, those types which cure with the 0* release of alcohol are used as sealants, adhesives, and coatings for electrical and electronic devices and S.o instruments. However, this type of room temperature-curable organopolysiloxane composition suffers from the problem of a poor adhesion for various substrates, such as glasses, metals, plastics, etc.
Problem to Be Solved by the Invention The present inventors achieved the invention under consideration as the result of extensive research directed at a solution to the aforementioned problem.
The invention takes as its object the introduction of a room temperature-curable organopolysiloxane composition which has both an excellent adhesiveness for various and diverse substrates as well as an excellent storage stability under seal.
i i 41
I
2 The present invention relates to a room temperature-curable organopolysiloxane composition comprising 100 weight parts organopolysiloxane having at least 2 silicon-bonded alkoxy groups in each molecule, and having the general structure
R
6 3-c R8 R 8
R
6 3-c (R70)c-Si-Y-(SiO)nSi-Y-Si(OR7)c I I R8 R8 wherein Rs is a monovalent hydrocarbon group; R7 is a monovalent hydrocarbon group or alkoxy-substituted hydrocarbon group; R8 is a group selected from the group consisting of monovalent hydrocarbon groups, halogenated hydrocarbon groups, and cyanoalkyl groups; Y is an oxygen atom; a is two or three; and a is a positive number 10 which gives a viscosity of 100 to 500,000 centipoise at 0.5 to 15 weight parts organosilane represented by the general formula
R
1 aSi(OR 2 )4.a ;j wherein R1 is a monovalent hydrocarbon group, R2 is a monovalknt hydrocarbon group or S alkoxy-substituted hydrocarbon group, and a is zero or one, or a partial hydrolysis condensate thereof, 0.01 to 15 weight parts mercapto group-containing alkoxysilane S represented by the general formula
R
4 b HS-R3-Si(ORS) 3 .b 4 I wherein R3 is a divalent organic group, R4 and R5 are substituted or unsubstituted ci 20 monovalent hydrocarbon groups, and b is zero or one, or partial hydrolysis condensate thereof, and 0.01 to 10 weight parts curing catalyst.
Considering the preceding in greater detail, the component used by the present invention is the base or principal material of the composition under consideration, and it is essential that it contain at least two silicon-bonded alkoxy groups in each molecule in order to obtain an excellent storage stability. Preferred among such components are straight-chain organopolysiloxanes having the silicon-bonded alkoxy group at the molecular terminals as represented by the general structure i S.iI o0 .o 0 o0 0Q 0 0 0 0 oo 0 0 o oD o D o 0040 00 0 0 00 6000 So00 0 C 00 0 6 8 8 6 R 3-c R R
I
3 c 1 3-c
(R
7 0) -Si-Y-(SiO) Si-Y-Si(OR )c 18 18 R R wherein R 6 is a monovalent hydrocarbon group; R 7 is a monovalent hydrocarbon group or alkoxy-substituted hydrocarbon group; R 8 is a group selected from among monovalent hydrocarbon groups, halogenated hydrocarbon groups, and cyanoalkyl groups; Y is an oxygen atom or a divalent hydrocarbon group; c is one, two, or three; and n is a positive number which gives a viscosity of 20 to 1,000,000 centipoise at 25 0 C. Furthermore, it is also possible to use organopolysiloxane in which such a straight-chain organopolysiloxane comprises the basic structure, but which additionally contains a branched, cyclic, or network portion or moiety.
Considering the above organopolysiloxane represented by general structure examples of the monovalent hydrocarbon groups are alkyl groups such as methyl, ethyl, propyl, butyl, hexyl, octyl, decyl, and octadecyl; cycloalkyl groups such as cyclopentyl and cyclohexyl; alkenyl groups such as vinyl and allyl; aryl groups such as phenyl, tolyl, and naphthyl; and aralkyl groups such as benzyl, phenylethyl, and phenylpropyl. The halogenated hydrocarbon groups are exemplified by chloromethyl, trifluoromethyl, chloropropyl, 3,3,3-trifluoro-propyl, chorophenyl, dibromophenyl, tetrachlorophenyl, and difluorophenyl. Examples of cyanoalkyl groups are beta-cyano-ethyl, gamma-cyanopropyl, and beta-cyanopropyl. The group R 7 is exemplified by alkyl groups such as methyl, ethyl, propyl, butyl, hexyl, and octyl, and by alkoxy-substituted alkyl iI
I
_-7 y v groups such as methoxyethyl, ethoxyethyl, methoxypropyl, 7 8 and methoxybutyl. It is preferred that R and R in each case contain 1 to 3 carbon atoms, and in fact the methyl group is particularly preferred. Y is to be an oxygen atom or a divalent hydrocarbon group, and examples of divalent hydrocarbon groups in this regard are alkylene S.O groups such as -CH 2
CH
2
-CH
2
CH
2
CH
2 -and -CH 2
CH(CH
3 oc The viscosity of component at 25 0 C should a 0 fall within the range of 20 to 1,000,000 cps. Good oo physical properties, and particularly softness and a high o elongation, cannot be imparted to the cured elastomer oo000 a when this value falls below 20 cps. On the other hand, 0 at values in excess of 1,000,000 cps, the composition will have a high viscosity, and its workability during 0o»:o application becomes extremely poor. Accordingly, values 00 0 *00 within the range of 100 to 500,000 cps are particularly preferred.
SO0o The organopolysiloxane comprising component (A) 0 0 o can be prepared by various methods known to the art. For example, when Y in the above general structure is an oxygen atom, synthesis can take the form of condensation between an alkoxy-silane and the corresponding silanol-terminated organopoly-siloxane in the presence or absence of catalyst. Catalysts usable in this regard are amines and the metal salts of carboxylic acids such as the zinc, tin, and iron salts of carboxylic acids. When the condensation reaction is conducted in the absence of catalyst, the reaction mixture is preferably heated to the reflux temperature of the alkoxysilane. When a catalyst is used, synthesis may be carried out by running the condensation reaction within the temperature interval from room temperature to the reflux temperature of the alkoxysilane.
i iH *e The molar ratio between the silanol groups in the organopolysiloxane and the alkoxy groups in the alkoxysilane in this condensation reaction should be at least 1 and preferably falls within the range of 5 to Other condensation reaction methods for the preparation of the organopolysiloxane of component (A) comprise, for example, the reaction of the corresponding silanol-terminated organopolysiloxane and chlorosilane represented by the formula o 2 m 3-m o° wherein R and R are defined as above, and m is zero, O, one, or two in the presence of a hydrogen halide binder such as pyridine, alpha-picoline, or other tertiary amines, as well as the condensation reaction between organopolysiloxane having silicon-bonded halogen at the O o« molecular chain terminals and monovalent alcohol represent by the formula R2OH (R 2 is defined as above) in the presence of a hydrogen halide binder as above.
When Y in the above general structure is an alkylene group, component can be prepared by the .00.o: addition reaction, in the presence of a platinum catalyst, of the corresponding alkenyl-terminated organopolysiloxane and alkoxysilane represented by the formula
R
6
R
3-c H-Si(OR )c 6 j7 wherein R 6 R and c are defined as above, or by the addition reaction of the corresponding SiH-terminated organopolysiloxane and i» S3-c R 9-Si(OR 7 c6 7 wherein R is an alkenyl group and R R and c are defined as above.
Component used by the present invention is n a crosslinker for the composition of the invention under consideration, and it is the essential component for Si
C
converting the composition of the present invention into a rubbery elastic substance by curing. This component comprises organosilane represented by the general formula 1 aSi(OR2 4-a a 2 wherein R is a monovalent hydrocarbon group, R is a monovalent hydrocarbon group or alkoxy-substituted hydrocarbon group, and a is zero or one, with the f monovalent hydrocarbon groups and alkoxy-substituted hydrocarbon groups being exemplified as above or partial I i hydrolysis condensate thereof.
Examples of component are as follows: tetrafunctional alkoxysilanes such as tetramethoxysilane, tetraethoxysilane, and methyl Cellosolve orthosilicate; trifunctional alkoxysilanes such as methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, vinyltrimethoxysilane, phenyltrimethoxysilane, *iad methyltrimethoxyethoxysilane; alkenyloxysilanes such as methyltrivinyloxysilane, t
K
1 i 7 methyltri(isopropenyloxy)silane, vinyltri(isopropenyloxy)silane, phenyltri(isopropenyloxy)silane, and tetra(isopropenyloxy)silane; and their partial hydrolysis condensates. These may be used individually, but it is also allowable to use mixtures of two or more species. Furthermore, the supplementary addition of difunctional alkoxysilane, such as diphenyldimethoxysilane, dimethyldimethoxysilane, etc., is permissible for the purpose of equipping the cured rubbery elastomer with a low modulus.
;I The quantity of addition of component (B) should fall within the range of 0.5 to 15 weight parts and preferably falls within the range of 1 to 10 weight S parts per 100 weight parts component When this quantity of addition is too low, the composition of the present invention will not adequately cure, and during S storage will suffer from an increase in viscosity and will readily gel. An excessive addition leads to slow curing and is uneconomical.
The mercapto group-containing alkoxysilane (or Spartial hydrolysis condensate thereof) comprising component used in the present invention is the crucial component for providing adhesion to various types of substrates.
R in the general formula given above is a divalent organic group, and examples in this regard are methylene, ethylene, propylene, butylene, chloroethylene, fluoroethylene, phenylene,
-CH
2
OCH
2
CH
2
CH
2
-CH
2 CH2OCH2CH 2 -CH2OCH(CH3)CH 2 2. 3 I rrrm~o u~ 8 -CHOC2CH 2
CH
2 OCHCH-, and divalent organic groups comprising combinations of two 4 5 or more of the preceding groups. R and R are substituted or unsubstituted monovalent hydrocarbon groups, and examples in this case are methyl, ethyl, propyl, octyl, phenyl, vinyl, and 3,3,3-trifluoropropyl.
Alkyl and alkoxyalkyl are particularly preferred among these.
Examples of the mercapto group-containing alkoxysilanes under consideration are as follows: V gamma-mercaptopropyltrimethoxysilane, c C gamma-mercaptopropylmethyldimethoxysilane, gamma-mercaptopropyltriethoxysilane, gamma-mercaptobutyltrimethoxysilane, gamma-mercaptobutyltris(methoxyethoxy)silane,
HSCH
2
CH
2 0(CH 2 3 Si(OCH 3 3 C C C HS- -i(OCH2CH3)3
HS
I c, -Si(OCH3)3 i i and HsHHSCH 2
CHOCHCH
2 CH Si(OCH 3 3 0 The addition of component should fall within the range of 0.01 to 15 weight parts and preferably 0.05 to 10 weight parts per 100 weight parts component When too little is added, adhesion to the substrate be,’.mes inadequate from the standpoint of i i 9 addition is economically disadvantageous.
Component is a catalyst which promotes the curing reaction of the composition of the present invention. Operable curing catalysts are the tin, titanium, zirconium, iron, antimony, bismuth, and manganese salts of organic acids, as well as organotitanate esters and organotitanium chelate coo compounds. Concrete examples of useful curing catalysts are tin compounds such as dibutyltin dilaurate, S0, dibutyltin dioctoate, stannous octoate, etc., and titanium compounds such as tetrabutyl titanate, tetraisopropyl titanate, diisopropoxybis(acetylacetone)titanium, diisopropoxybis(ethyl acetoacetate)- .00:0 titanium, etc. The preferred quantity of addition for oo this component is 0.1 to 5 weight parts per 100 weight parts component 0 a0 The composition of the present invention, in oo addition to the preceding components through can also optionally contain microparticulate inorganic filler in order to improve the physical properties of the cured product and improve the flow properties prior to curing.
Here, the quantity of addition should fall within the range of 1 to 200 weight parts and preferably 5 to 100 weight parts per 100 weight parts component Examples of such inorganic fillers are dry-method silicas, wet-method silicas, quartz powder, calcium carbonate, titanium dioxide, diatomaceous earth, aluminum hydroxide, and microparticulate alumina, magnesia, zinc oxide, and zinc carbonate, as well as the preceding after surface treatment with, for example, silane, silazane, polysiloxane with a low degree of polymerization, or organic compounds.
C* t*r In addition, as long as the object of the present invention is not compromised, there is no impediment to the addition of the following to the composition of the present invention: organic solvents, diorganopolysiloxane with trimethylsilylated molecular chain terminals, flame retardants, plasticizers, S thixotropic agents, general adhesion promoters, antimolds, etc.
°o The composition of the present invention is 0oo obtained by mixing components through and the 0 o various optional additives while excluding moisture. The o.0 o 0o obtained composition is then stored as such in a sealed container, and cures to give a rubbery elastic substance upon exposure to atmospheric moisture when applied. It 00’0 can be used as a so-called single-package room 0 0, temperature-curable organopolysiloxane composition.
The present invention will be explained in 000. greater detail through the following illustrative 00 examples. In the examples, comparison examples, and reference examples, parts weight parts in all cases and the viscosity is the value at 25 degrees Centigrade.
EXAMPLE 1 100 Parts alpha,omega-bis(trimethoxysilyl)- Sdimethylpoly siloxane with a viscosity of 15,000 centipoise and 12 parts dry-method silica (surface treated with hexamethyldisilazane, specific surface area 2 =110 m /g by the BET method) were mixed at room temperature for 30 minutes. This was then further mixed at 40 mmHg while heating to 1800C until homogeneous. In order to prepare the room temperature-curable organopolysiloxane compositions reported in Table 1, the following were then mixed to homogeneity into the J 1 1 11 obtained mixture while excluding moisture: 5 parts methyltrimethoxysilane, 1.5 parts diisopropoxybis(ethyl acetoacetate)titanium, and 0.5 parts gamma-mercaptopropyltrimethoxysilane or 0.5 parts gammamercaptopropylmethyldimethoxysilane. The products were then placed in aluminum tubes and stored under seal.
The adhesion of these room temperature-curable S organopolysiloxane compositions to various substrates was t then measured, and the measurement results are reported C in Table 2. Adhesion testing was conducted as follows.
The room temperature-curable organopolysiloxane c, composition as described above was extruded in bead-form (width 15 mm x length 40 mm x thickness 5 cm) on the particular substrate according to the tab adhesion test cI method, and this was cured by standing for 7 days at 20 0
C
S and 55% RH. The obtained cured bead was pulled in order C to separate it from the substrate surface, and the resulting peel surface was examined. The proportion of rupture in the cured layer is reported as the cohesive rupture.
r For comparison, a room temperature-curable organopolysiloxane composition was prepared as above i with the exception that the aforementioned mercapto group-containing alkoxysilane was not used. The result of adhesion measurement on this composition were as reported in Table 2.
TABLE 1 COMPONENT S PRE SENT
INVENTION
Alpha, omega-bis (trijnethoxysilyldimethylpolysiloxane, parts Hexamethyldis ilazane- treated silica, parts Methyltrimethoxysilane, parts Diisopropoxybis (ethylacetoacetate)titanium, parts 100 12 COMPARI SON
EXAMPLE
100 12 1.5 0.5 1.5 Gamma-mercaptopropyltrimethoxysila–e, parts
CD
CD
Ca)
CD,
2.
0 a& 0
CD
(A,
CD
0 Ci,
C=
CD
0- 9t 9 9 9 0 9 9 0u 6 0 0 9 9* 9 9 9 4 4 94 49. 949 9 994 409 4 9 0 0 4 0 *o a a 9.
0004 #609 99 4* 9 0 9 9 TABLE 2
PRESENT
INVENTION
COMPARISON
EXAMPLE SUBSTRATE Aluminum Copper Glass Epoxy resin Polycarbonate resin 100% 100% 100%
I
I 14 EXAMPLE 2 Room temperature-curable organopolysiloxane composition prepared as in Example 1 was extruded from an aluminum tube into a metal mold for sheet molding. A mm-thick sheet was prepared by curing by standing for 7 days at 20 0 C and 55% RH. The physical properties of this sheet were then measured according to JIS K 6301. In c addition, the aforementioned aluminum tube was placed in an oven maintained at 50 0 C, and thermal aging was carried out by allowing this to stand as such for 4 weeks. The S physical properties of the thermally aged room t. temperature-curable organopolysiloxane composition were then measured as above. The various measurement results were as reported in Table 3.
eri For comparison, a room temperature-curable t organopolysiloxane composition was prepared as in Example 1 with the modification that an S alpha,omega-bis(dihydroxy)dimethylpoly-siloxane with a viscosity of 15,000 centipoise was used in place of the alpha,omega-bis(trimethoxysilyl)dimethylpolysiloxane with I r.r a viscosity of 15,000 centipoise of Example 1. The physical properties of this composition were measured as described above, and these results were as reported in Table 3.
I
1
N-«I
$4 *4$4 .4 fl$4$4 $4$4% r $4 4 $4 fin TABLE 3 PRESENT COMPARISON INVENTION EXAMPLE PHYSICAL PROPERTIES Prior to heat aging Hardness (JIS A) Tensile strength, Elongation, (kg/ cm2) 34 31 430 18 12 350 After heat aging Hardness (JIS A) Tensile strength, (kg/cm2) Elongation, 33 measurements could not be 30 conducted due to poor curing 420 -C 16 EXAMPLE 3 A room temperature-curable organopolysiloxane composition was prepared as in Example 1 with the exception that gamma-mercaptopropylmethyldimethoxysilane was used in place of the gamma-mercaptopropyltrimethoxysilane of Example 1. The adhesion or bonding of this S room temperature-curable organopolysiloxane composition e t for various substrates was measured as in Example 1, and S te these results were as reported in Table 4.
r r rI t TABLE 4 S’ ADHESION SUBSTRATE cohesive rupture) Aluminum Copper 100 Glass 100 T Epoxy resin c Polycarbonate resin EXAMPLE 4 Room temperature-curable organopolysiloxane compositions as reported in Table 5 were prepared by the same procedures as in Example 1 and Example 2 with the exception that 100 parts calcium carbonate (average Sparticle diameter 2.2 microns) was used in place of the hexamethyldisilazane-treated silica of Example 1. For comparison, a room temperature-curable organopolysiloxane composition was similarly prepared as reported in Table with the exception that mercapto group-containing silane, component above, was not added. These compositions were subjected to adhesion testing as in Example 1, and these results were as reported in Table 6.
1 1 1 Nn A lan N As r A N ar M a r O a N- A A A An rl ar N nr A TABLE
COMPONENTS
Alpha,omega-bis(trimethoxysilyl)dimethylpolysiloxane, parts Calcium carbonate, parts (average particle diameter 2.2 microns) Methyltrimethoxysilane, parts Diisopropoxybis(ethylacetoacetate)titanium, parts Gamma-mercaptopropyltrimethoxysilane, parts Gamma-mercaptopropylmethyldimethoxysilane, parts
PRESENT
INVENTION
100 100 100 100 5 5 1.5 1.5
COMPARISON
EXAMPLE
100 100 .r -Lr L i -L 1catalyst is used, synthesis may be carried out by running the condensation reaction within the temperature interval from room temperature to the ref lux temperature of the alkoxysilane.
I 9 -a
I
I
.4
I
01 600 C CC C C C C C cr C C r C f C C C CO C
C’
0 0000- b a 0 00000 %D 0D HO0 z H 14 E- V) z~ 4
E-
4 H La 0 HQ a *GW 0r-i C/2 r- -4P W, -0 1 9 4′ ii -X-j organopolysiloxane and 19 EXAMPLE 100 Parts alpha,omega-bis(methyldimethoxysilyl)dimethyl polysiloxane with a viscosity of 13,000 centipoise and 11 parts dry-method silica with a specific surface area of 200 m 2 /g (BET) were mixed for 30 minutes at room temperature, followed by additional mixing at 40 mmHg to homogeneity. A room temperature-curable organopolysiloxane composition was prepared by mixing the following into this mixture to homogeneity while excluding moisture: 4 parts vinyltrimethoxysilane, 1.5 o ao o parts tetrabutyl titanate, and 0.5 parts gamma-mercaptomethyltrimethoxysilane. This composition was then subjected to adhesion testing as in Example 1, and these results were as reported in Table 7.
O For comparison, a room temperature-curable ,o organopolysiloxane composition was prepared as above with the exception that the 0.5 parts gamma-mercaptopropyltrimethoxysilane was not added. This was also subjected to adhesion testing, and these results were as reported in Table 7.
1 !i S v v 1 As A A A A a *0 0 A A 0 A A A a A A A fleA P A -A A S eq eq A e q I A TABLE 7
PRESENT
INVENTION
COMPARISON
EXAMPLE
SUBSTRATE
Aluminum Copper Glass Epoxy resin Polycarbonate resin 100% 100% 100% 100% 50% 0% 0%
K
-CH
2
UCH
2
CH
2
CH
2
-CH
2
CH
2
OCH
2
CH
2 -CHO2CH(CH 3
)CH
2 2 3 i» 21 Because the room temperature-curable organopolysiloxane composition of the present invention comprises components through and particularly because it contains the organopolysiloxane comprising component and the mercapto group-containing silane or partial hydrolysis condensate thereof comprising component it is characterized by an excellent adhesion or bonding for various substrates and by an excellent storage stability under seal.
9 Accordingly, it can be used as a construction B sealant; as a sealant, adhesive, or anti-moisture coating for electrical and electronic components; and as a coating or adhesive for fibers and fibrous articles, glass articles, metal articles, and plastic articles, t 0 1
Claims (2)
1. A room temperature-curable organopolysiloxane composition comprising 100 weight parts organopolysiloxane having at least 2 silicon-bonded alkoxy groups in each molecule, and having the general structure R 6
3-c R8 R8 R 6 3-c 7 )c R8 R 8 wherein R 6 is a monovalent hydrocarbon group; R7 is a monovalent hydrocarbon group or alkoxy-substituted hydrocarbon group; Rs is a group selected from the group consisting of monovalent hydrocarbon groups, halogenated hydrocarbon groups, and 1. cyanoalkyl groups Y is an oxygen atom; organopoy is two or three; and compo is a positive number which gives a viscosity of 100 to 500,000 centipoise at (AB) 0.5 to 15 weight parts organosilane represented by the general formula alkoxy groups in each molecule, and having the general structure (R)c-Si-Y-Si(OR2)4nSi-Y-Si(OR7 wherein R6 is a monovalent hydrocarbon group, R2 is a monovalent hydrocarbon group or alkoxy-substituted hydrocarbon group, and a is zero or one, or a partial hydrolysis condensate thereof, 0.01 to 15 weight parts mercapto group-containing alkoxysilane S(B) 0.5 to 15 weight parts organosiane represented by the general formula R4b r -a HS-R3-Si(OR)3-b wherein R is a divalent organic group, R4 and Rs are substituted or unsubstituted monovalent hydrocarbon groups, and a is zero or one, or partial hydrolysis condensate thereof, and 0.01 to 10 weight parts curing catalyst. i U.L -v imnuig wuie neUting uo Lou-u unui.i flomogeneuus. LLL order to prepare the room temperature-curable organopolysiloxane compositions reported in Table 1, the following were then mixed to homogeneity into the AM- .4 *1 b 23 2. The room temperature-curable organopolysiloxane composition according to claim 2 in which the mercapto group-containing alkoxysilane is gamma- mercaptopropyltrimethoxysilane or (gamma-mercaptopropyl)melhyldimethoxysilane. DATED THIS 29TH DAY OF JANUARY, 1992 TORAY SILICONE COMPANY. LTD. WATERMARK PATENT TRADEMARK ATTORNEYS THE ATRIUM 290 BURWOOD ROAD HAWTHORN VICTORIA 3122 AUSTRAUA IAS:JC DOC 8: AU3587589.WPC :1 I ii ii 1 U I C C C r C r C C I C C I C C I CC C I IC I C C C C C
AU35875/89A
1988-06-02
1989-06-01
Room temperature curable organopolysiloxane composition
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1988-06-02
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1988-06-02
1988-06-02
Room temperature curable organopolysiloxane composition
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Room temperature curable organopolysiloxane composition
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1988-11-28
1990-03-06
Dow Corning Corporation
Silicone sealants having reduced color
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1989-03-22
Perennator Gmbh
Elastomer-forming compositions
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1990-03-23
1994-12-07
信越化学工業株式会社
Method for producing silicone block polymer
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1990-11-28
2000-11-20
東レ・ダウコーニング・シリコーン株式会社
Room temperature curable organopolysiloxane composition
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1992-03-27
1996-08-20
Heraeus Kulzer Gmbh & Co. Kg
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Toray Dow Corning Silicone Co Ltd
Curable organopolysiloxane composition and method for bonding substrate to adherend using the same
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1988
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1989-12-13
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1989-12-11
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1995-09-07
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1995-08-02
US4973644A
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1990-11-27
CA1330678C
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1994-07-12
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(en)
1995-12-06
AU3587589A
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1989-12-07
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1991-06-19
DE68923658T2
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1996-02-01
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