DE69910279T2 - Flüssige spritzgiessbare Silikonelastomere mit Adhäsion ohne Grundierung - Google Patents
Flüssige spritzgiessbare Silikonelastomere mit Adhäsion ohne Grundierung Download PDFInfo
- Publication number
- DE69910279T2 DE69910279T2 DE69910279T DE69910279T DE69910279T2 DE 69910279 T2 DE69910279 T2 DE 69910279T2 DE 69910279 T DE69910279 T DE 69910279T DE 69910279 T DE69910279 T DE 69910279T DE 69910279 T2 DE69910279 T2 DE 69910279T2
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- Germany
- Prior art keywords
- silicone
- liquid injection
- carbon atoms
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- weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 229920002379 silicone rubber Polymers 0.000 title claims description 33
- 239000007788 liquid Substances 0.000 title description 115
- 239000000203 mixture Substances 0.000 claims description 118
- 229920001296 polysiloxane Polymers 0.000 claims description 103
- -1 cationic organic nitrogen compound Chemical class 0.000 claims description 85
- 230000006835 compression Effects 0.000 claims description 59
- 238000007906 compression Methods 0.000 claims description 59
- 229920001971 elastomer Polymers 0.000 claims description 47
- 125000004432 carbon atom Chemical group C* 0.000 claims description 41
- 125000003342 alkenyl group Chemical group 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 239000000758 substrate Substances 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 229920001187 thermosetting polymer Polymers 0.000 claims description 18
- 229920000642 polymer Polymers 0.000 claims description 17
- 150000001768 cations Chemical class 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000000806 elastomer Substances 0.000 claims description 10
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 9
- 150000002830 nitrogen compounds Chemical class 0.000 claims description 8
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 7
- 229920001169 thermoplastic Polymers 0.000 claims description 6
- 125000000962 organic group Chemical group 0.000 claims description 5
- 150000004756 silanes Chemical class 0.000 claims description 5
- GPWPWELMLCKXRP-MDZDMXLPSA-N bis(3-trimethoxysilylpropyl) (e)-but-2-enedioate Chemical compound CO[Si](OC)(OC)CCCOC(=O)\C=C\C(=O)OCCC[Si](OC)(OC)OC GPWPWELMLCKXRP-MDZDMXLPSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000002091 cationic group Chemical group 0.000 claims description 3
- 239000004634 thermosetting polymer Substances 0.000 claims description 3
- VICYBMUVWHJEFT-UHFFFAOYSA-N dodecyltrimethylammonium ion Chemical compound CCCCCCCCCCCC[N+](C)(C)C VICYBMUVWHJEFT-UHFFFAOYSA-N 0.000 claims 1
- ISNICOKBNZOJQG-UHFFFAOYSA-O guanidinium ion Chemical compound C[NH+]=C(N(C)C)N(C)C ISNICOKBNZOJQG-UHFFFAOYSA-O 0.000 claims 1
- 229920000307 polymer substrate Polymers 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims 1
- 238000001746 injection moulding Methods 0.000 description 71
- 238000001723 curing Methods 0.000 description 63
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 58
- 238000002360 preparation method Methods 0.000 description 49
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 48
- 239000000654 additive Substances 0.000 description 47
- 229920002554 vinyl polymer Polymers 0.000 description 41
- 239000000945 filler Substances 0.000 description 40
- 230000000704 physical effect Effects 0.000 description 40
- 239000005060 rubber Substances 0.000 description 37
- 238000002347 injection Methods 0.000 description 32
- 239000007924 injection Substances 0.000 description 32
- 229920005989 resin Polymers 0.000 description 31
- 239000011347 resin Substances 0.000 description 31
- 230000000996 additive effect Effects 0.000 description 29
- 239000000463 material Substances 0.000 description 26
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 150000003254 radicals Chemical class 0.000 description 24
- 239000003054 catalyst Substances 0.000 description 22
- 239000000377 silicon dioxide Substances 0.000 description 18
- 239000003112 inhibitor Substances 0.000 description 15
- 239000004215 Carbon black (E152) Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 229930195733 hydrocarbon Natural products 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- 229920001577 copolymer Polymers 0.000 description 13
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 13
- 229910052697 platinum Inorganic materials 0.000 description 12
- 235000012239 silicon dioxide Nutrition 0.000 description 12
- 238000011282 treatment Methods 0.000 description 11
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 8
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 7
- 150000004678 hydrides Chemical group 0.000 description 7
- 238000006459 hydrosilylation reaction Methods 0.000 description 7
- 238000000465 moulding Methods 0.000 description 7
- 238000004132 cross linking Methods 0.000 description 6
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 6
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 6
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 6
- 239000004945 silicone rubber Substances 0.000 description 6
- 239000002318 adhesion promoter Substances 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- 239000001099 ammonium carbonate Substances 0.000 description 5
- 235000012501 ammonium carbonate Nutrition 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000011065 in-situ storage Methods 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 241000894007 species Species 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 239000003431 cross linking reagent Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 229910021485 fumed silica Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000007789 sealing Methods 0.000 description 4
- 229920002050 silicone resin Polymers 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Chemical compound Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 description 3
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920006324 polyoxymethylene Polymers 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 125000005372 silanol group Chemical group 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000001721 transfer moulding Methods 0.000 description 3
- IMGVXSGKBGOBPV-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-2,2,3-trimethylcyclohexane Chemical compound CC1CCCC(OOC(C)(C)C)(OOC(C)(C)C)C1(C)C IMGVXSGKBGOBPV-UHFFFAOYSA-N 0.000 description 2
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 229920001807 Urea-formaldehyde Polymers 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000005210 alkyl ammonium group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 229940106691 bisphenol a Drugs 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000007596 consolidation process Methods 0.000 description 2
- 230000008094 contradictory effect Effects 0.000 description 2
- 229910021419 crystalline silicon Inorganic materials 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical class C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- XJWSAJYUBXQQDR-UHFFFAOYSA-M dodecyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)C XJWSAJYUBXQQDR-UHFFFAOYSA-M 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- NYMPGSQKHIOWIO-UHFFFAOYSA-N hydroxy(diphenyl)silicon Chemical class C=1C=CC=CC=1[Si](O)C1=CC=CC=C1 NYMPGSQKHIOWIO-UHFFFAOYSA-N 0.000 description 2
- AAUNBWYUJICUKP-UHFFFAOYSA-N hypoiodite Chemical compound I[O-] AAUNBWYUJICUKP-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000003780 insertion Methods 0.000 description 2
- 230000037431 insertion Effects 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 229960004592 isopropanol Drugs 0.000 description 2
- 239000012705 liquid precursor Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical compound CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 150000003058 platinum compounds Chemical class 0.000 description 2
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 2
- 229920000052 poly(p-xylylene) Polymers 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- 239000012763 reinforcing filler Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- 239000011043 treated quartz Substances 0.000 description 2
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 2
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 description 1
- ZLIMCRGCSZUEQH-BUHFOSPRSA-N (e)-2,3-bis(3-trimethoxysilylpropyl)but-2-enedioic acid Chemical compound CO[Si](OC)(OC)CCC\C(C(O)=O)=C(C(O)=O)\CCC[Si](OC)(OC)OC ZLIMCRGCSZUEQH-BUHFOSPRSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- VIAMIUDTTIDZCA-ODZAUARKSA-N (z)-but-2-enedioic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.OC(=O)\C=C/C(O)=O VIAMIUDTTIDZCA-ODZAUARKSA-N 0.000 description 1
- ROLAGNYPWIVYTG-UHFFFAOYSA-N 1,2-bis(4-methoxyphenyl)ethanamine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CC(N)C1=CC=C(OC)C=C1 ROLAGNYPWIVYTG-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- GUOSQNAUYHMCRU-UHFFFAOYSA-N 11-Aminoundecanoic acid Chemical compound NCCCCCCCCCCC(O)=O GUOSQNAUYHMCRU-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- GQHYXXXFYXNSDV-UHFFFAOYSA-N 2-benzofuran-1,3-dione;2,2-bis(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)CO.C1=CC=C2C(=O)OC(=O)C2=C1 GQHYXXXFYXNSDV-UHFFFAOYSA-N 0.000 description 1
- QLEITUFVKZSFRB-UHFFFAOYSA-N 2-benzofuran-1,3-dione;propane-1,2,3-triol Chemical compound OCC(O)CO.C1=CC=C2C(=O)OC(=O)C2=C1 QLEITUFVKZSFRB-UHFFFAOYSA-N 0.000 description 1
- YVNXBDIBOMELMY-UHFFFAOYSA-N 2h-benzotriazole-5-carboxamide Chemical compound NC(=O)C1=CC=C2N=NNC2=C1 YVNXBDIBOMELMY-UHFFFAOYSA-N 0.000 description 1
- GUOVBFFLXKJFEE-UHFFFAOYSA-N 2h-benzotriazole-5-carboxylic acid Chemical compound C1=C(C(=O)O)C=CC2=NNN=C21 GUOVBFFLXKJFEE-UHFFFAOYSA-N 0.000 description 1
- LDTAOIUHUHHCMU-UHFFFAOYSA-N 3-methylpent-1-ene Chemical compound CCC(C)C=C LDTAOIUHUHHCMU-UHFFFAOYSA-N 0.000 description 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- DJHGAFSJWGLOIV-UHFFFAOYSA-K Arsenate3- Chemical compound [O-][As]([O-])([O-])=O DJHGAFSJWGLOIV-UHFFFAOYSA-K 0.000 description 1
- DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical compound O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 229920001780 ECTFE Polymers 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
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Classifications
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- 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
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
- C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/19—Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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- 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)
- Injection Moulding Of Plastics Or The Like (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32461 | 1998-02-26 | ||
| US09/032,461 US6040366A (en) | 1998-02-27 | 1998-02-27 | Liquid injection molding silicone elastomers having primerless adhesion |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69910279D1 DE69910279D1 (de) | 2003-09-18 |
| DE69910279T2 true DE69910279T2 (de) | 2004-06-09 |
Family
ID=21865084
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69910279T Expired - Lifetime DE69910279T2 (de) | 1998-02-26 | 1999-02-10 | Flüssige spritzgiessbare Silikonelastomere mit Adhäsion ohne Grundierung |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US6040366A (enExample) |
| EP (1) | EP0939101B1 (enExample) |
| JP (2) | JP4727775B2 (enExample) |
| DE (1) | DE69910279T2 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6663967B1 (en) * | 2000-11-17 | 2003-12-16 | Bryant Rubber Corporation | Moldable silicone elastomers having selective primerless adhesion |
| US7104823B2 (en) * | 2002-05-16 | 2006-09-12 | Homac Mfg. Company | Enhanced separable connector with thermoplastic member and related methods |
| US7104822B2 (en) * | 2002-05-16 | 2006-09-12 | Homac Mfg. Company | Electrical connector including silicone elastomeric material and associated methods |
| US6871838B2 (en) * | 2003-04-03 | 2005-03-29 | B. Braun Medical Inc. | Injection port valve |
| JP4903987B2 (ja) * | 2004-03-19 | 2012-03-28 | 東レ・ダウコーニング株式会社 | 半導体装置の製造方法 |
| JP4684860B2 (ja) * | 2005-11-11 | 2011-05-18 | 信越化学工業株式会社 | 射出成形用付加硬化型液状シリコーンゴム組成物及び該組成物の流動性調整方法並びにシリコーンゴム組成物の射出成形方法 |
| US7867204B2 (en) * | 2006-05-04 | 2011-01-11 | B. Braun Medical Inc. | Needleless access port valves |
| US20070270756A1 (en) * | 2006-05-22 | 2007-11-22 | Peter Peppel | Needleless access port valves |
| US20080176670A1 (en) | 2007-01-19 | 2008-07-24 | Eaton Corporation | Liquid injection molded hand grips |
| CN103588984A (zh) * | 2007-02-22 | 2014-02-19 | 道康宁公司 | 制备导电薄膜的方法和由该方法制得的制品 |
| JP4991881B2 (ja) * | 2007-03-07 | 2012-08-01 | サン−ゴバン パフォーマンス プラスティックス コーポレイション | シリコーン組成物を含有する物品およびそれらの製造方法 |
| WO2008109863A2 (en) * | 2007-03-07 | 2008-09-12 | Saint-Gobain Performance Plastics Corporation | Multi-layer tubes |
| EP2244875A1 (en) * | 2007-12-28 | 2010-11-03 | Saint-Gobain Performance Plastics Corporation | Reinforced tube |
| EP2196503B1 (en) * | 2008-12-12 | 2015-02-18 | Nitto Denko Corporation | Thermosetting silicone resin composition, silicone resin, silicone resin sheet and use thereof |
| JP5566088B2 (ja) * | 2008-12-12 | 2014-08-06 | 日東電工株式会社 | 熱硬化性シリコーン樹脂用組成物 |
| JP5566036B2 (ja) * | 2009-02-02 | 2014-08-06 | 日東電工株式会社 | 熱硬化性シリコーン樹脂用組成物 |
| US20110136985A1 (en) * | 2009-12-09 | 2011-06-09 | Moon Douglas E | Molded article having a mold imparted release layer coating |
| EP3853299B1 (en) * | 2018-09-19 | 2025-08-20 | Dow Silicones Corporation | Aryl scission inhibition in aryl-functionalized polysiloxane |
Family Cites Families (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2803619A (en) * | 1954-12-23 | 1957-08-20 | Dow Corning | Low compression set siloxane elastomers containing a vinyl organosiloxane |
| NL129346C (enExample) * | 1966-06-23 | |||
| US3635743A (en) * | 1969-01-06 | 1972-01-18 | Gen Electric | Reinforcing silica filler |
| US3814730A (en) * | 1970-08-06 | 1974-06-04 | Gen Electric | Platinum complexes of unsaturated siloxanes and platinum containing organopolysiloxanes |
| US3715334A (en) * | 1970-11-27 | 1973-02-06 | Gen Electric | Platinum-vinylsiloxanes |
| US3775452A (en) * | 1971-04-28 | 1973-11-27 | Gen Electric | Platinum complexes of unsaturated siloxanes and platinum containing organopolysiloxanes |
| US3847848A (en) * | 1972-12-04 | 1974-11-12 | Gen Electric | Two-part room temperature vulcanizable silicone rubber compositions |
| US3817910A (en) * | 1973-01-02 | 1974-06-18 | Stauffer Chemical Co | Low compression set siloxane elastomers |
| US3957713A (en) * | 1973-04-13 | 1976-05-18 | General Electric Company | High strength organopolysiloxane compositions |
| US3884866A (en) * | 1973-04-13 | 1975-05-20 | Gen Electric | High strength organopolysiloxane compositions |
| US4162243A (en) * | 1978-05-08 | 1979-07-24 | Dow Corning Corporation | High strength, extrudable silicone elastomer compositions |
| US4256870A (en) * | 1979-05-17 | 1981-03-17 | General Electric Company | Solventless release compositions, methods and articles of manufacture |
| US4427801A (en) * | 1982-04-14 | 1984-01-24 | Dow Corning Corporation | Extrudable silicone elastomer compositions |
| FR2557121B1 (fr) * | 1983-12-21 | 1986-10-10 | Rhone Poulenc Spec Chim | Compositions elastomeriques organopolysiloxaniques vulcanisables a chaud a caracteristiques physiques ameliorees |
| CA1270973A (en) * | 1985-01-03 | 1990-06-26 | Melvin R. Toub | Self-bonding precious metal catalyzed silicone rubber compositions |
| JPS62197453A (ja) * | 1986-02-25 | 1987-09-01 | Shin Etsu Chem Co Ltd | シリコ−ン組成物 |
| JPH0655895B2 (ja) * | 1989-03-16 | 1994-07-27 | 信越化学工業株式会社 | 硬化性シリコーンゴム組成物 |
| JP2796744B2 (ja) * | 1989-10-31 | 1998-09-10 | 東レ・ダウコーニング・シリコーン株式会社 | 硬化性オルガノポリシロキサンゴム組成物 |
| DE4014310A1 (de) * | 1990-05-04 | 1991-11-07 | Bayer Ag | Siliconelastomere mit vermindertem druckverformungsrest sowie verfahren zu deren herstellung |
| JP3105950B2 (ja) * | 1991-02-20 | 2000-11-06 | 東レ・ダウコーニング・シリコーン株式会社 | オルガノポリシロキサンゴム組成物 |
| US5164461A (en) * | 1991-03-14 | 1992-11-17 | General Electric Company | Addition-curable silicone adhesive compositions |
| US5260364A (en) * | 1992-08-07 | 1993-11-09 | Wacker Silicones Corporation | Silicone rubber having reduced compression set |
| JP3341381B2 (ja) * | 1993-08-09 | 2002-11-05 | 信越化学工業株式会社 | 加熱硬化型シリコーンゴム組成物 |
| US5569688A (en) * | 1993-10-21 | 1996-10-29 | Shin-Etsu Chemical Co., Ltd. | Heat-curable silicone rubber compositions |
| JP3189601B2 (ja) * | 1993-10-21 | 2001-07-16 | 信越化学工業株式会社 | 加熱硬化型シリコーンゴム組成物及びその硬化方法 |
| JP3556259B2 (ja) * | 1993-12-24 | 2004-08-18 | 東レ・ダウコーニング・シリコーン株式会社 | オルガノポリシロキサンエマルジョンおよび該エマルジョンにより処理してなる繊維 |
| JP2937228B2 (ja) * | 1994-07-20 | 1999-08-23 | 矢崎総業株式会社 | コネクタ防水用シール部品 |
| JP3303549B2 (ja) * | 1994-09-08 | 2002-07-22 | 三菱マテリアル株式会社 | 抗微生物性重合体 |
| JP3109404B2 (ja) * | 1994-10-06 | 2000-11-13 | 信越化学工業株式会社 | シリコーンゴムコンパウンドの製造方法 |
| JPH08176446A (ja) * | 1994-12-27 | 1996-07-09 | Shin Etsu Chem Co Ltd | 硬化性シリコーン組成物及びその硬化物 |
| US5486551A (en) * | 1995-01-03 | 1996-01-23 | Dow Corning Corporation | Method for preparing a finely divided, free flowing organosiloxane elastomer base exhibiting reduced compression set following curing |
| US5674966A (en) * | 1995-06-05 | 1997-10-07 | General Electric Company | Low molecular weight liquid injection molding resins having a high vinyl content |
| FR2736060B1 (fr) * | 1995-06-30 | 1998-10-23 | Gen Electric | Compositions a base de silicone elastomere, durcissables par la chaleur, et articles obtenus a partir de ces compositions |
| JP3666156B2 (ja) * | 1995-12-14 | 2005-06-29 | 和光純薬工業株式会社 | シリコン含有ブロックコポリマー |
| DE19614343A1 (de) * | 1996-04-11 | 1997-10-16 | Wacker Chemie Gmbh | Silikonkautschuke mit verbesserter Fellfestigkeit und niedrigem Druckverformungsrest |
| DE19631120A1 (de) * | 1996-08-01 | 1998-02-05 | Wacker Chemie Gmbh | Additionsvernetzte Siliconelastomere mit verringertem Druckverformungsrest |
| US5977220A (en) * | 1997-12-29 | 1999-11-02 | General Electric Company | Process for imparting low compression set to liquid injection moldable silicone elastomers |
| US5998515A (en) * | 1997-12-29 | 1999-12-07 | General Electric Company | Liquid injection molding silicone elastomers having primerless adhesion |
| JPH11339863A (ja) * | 1998-05-29 | 1999-12-10 | Kokusai Electric Co Ltd | 電池パック、その識別方法及び装置 |
-
1998
- 1998-02-27 US US09/032,461 patent/US6040366A/en not_active Expired - Lifetime
-
1999
- 1999-02-10 EP EP99300957A patent/EP0939101B1/en not_active Expired - Lifetime
- 1999-02-10 DE DE69910279T patent/DE69910279T2/de not_active Expired - Lifetime
- 1999-02-22 JP JP04245399A patent/JP4727775B2/ja not_active Expired - Fee Related
-
2010
- 2010-06-02 JP JP2010126939A patent/JP4699560B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH11323134A (ja) | 1999-11-26 |
| EP0939101B1 (en) | 2003-08-13 |
| EP0939101A3 (en) | 1999-09-22 |
| DE69910279D1 (de) | 2003-09-18 |
| JP2010185089A (ja) | 2010-08-26 |
| US6040366A (en) | 2000-03-21 |
| EP0939101A2 (en) | 1999-09-01 |
| JP4727775B2 (ja) | 2011-07-20 |
| JP4699560B2 (ja) | 2011-06-15 |
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| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |