CA1146560A - Silanes renfermant des groupements imides - Google Patents

Silanes renfermant des groupements imides

Info

Publication number: CA1146560A
Authority: CA; Canada
Prior art keywords: formula; methyl; atoms; mol; solution
Prior art date: 1978-08-30
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

CA000401795A

Other languages

English (en)

Inventor

Siegfried Wyler

Dieter Lohmann

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.)

BASF Schweiz AG

Original Assignee

Ciba Geigy Investments 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.)

1978-08-30

Filing date

1982-04-27

Publication date

1983-05-17

1978-08-30 Priority claimed from CH915478A external-priority patent/CH641470A5/de

1982-04-27 Application filed by Ciba Geigy Investments Ltd filed Critical Ciba Geigy Investments Ltd

1982-04-27 Priority to CA000401795A priority Critical patent/CA1146560A/fr

1983-05-17 Application granted granted Critical

1983-05-17 Publication of CA1146560A publication Critical patent/CA1146560A/fr

Status Expired legal-status Critical Current

Links

150000004756 silanes Chemical class 0.000 title description 7
125000005462 imide group Chemical group 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 23
239000000460 chlorine Substances 0.000 claims abstract description 15
229910052801 chlorine Inorganic materials 0.000 claims abstract description 15
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
125000004432 carbon atom Chemical group C* 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
229910052710 silicon Inorganic materials 0.000 claims description 7
229910052736 halogen Chemical group 0.000 claims description 6
150000002367 halogens Chemical group 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000002947 alkylene group Chemical group 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 3
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
229920002554 vinyl polymer Polymers 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
239000002318 adhesion promoter Substances 0.000 abstract description 21
229920005989 resin Polymers 0.000 abstract description 5
239000011347 resin Substances 0.000 abstract description 5
229910003480 inorganic solid Inorganic materials 0.000 abstract description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 34
238000000034 method Methods 0.000 description 26
239000000047 product Substances 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
238000002360 preparation method Methods 0.000 description 18
238000009835 boiling Methods 0.000 description 13
239000000203 mixture Substances 0.000 description 13
229910000077 silane Inorganic materials 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000011521 glass Substances 0.000 description 12
239000002904 solvent Substances 0.000 description 12
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 11
229910052757 nitrogen Inorganic materials 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
150000003254 radicals Chemical class 0.000 description 8
239000007858 starting material Substances 0.000 description 8
239000003921 oil Substances 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
239000004744 fabric Substances 0.000 description 5
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
239000000758 substrate Substances 0.000 description 5
239000008096 xylene Substances 0.000 description 5
MFGALGYVFGDXIX-UHFFFAOYSA-N 2,3-Dimethylmaleic anhydride Chemical compound CC1=C(C)C(=O)OC1=O MFGALGYVFGDXIX-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000000853 adhesive Substances 0.000 description 4
230000001070 adhesive effect Effects 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
238000001035 drying Methods 0.000 description 4
125000004433 nitrogen atom Chemical group N* 0.000 description 4
229910000510 noble metal Inorganic materials 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001339 alkali metal compounds Chemical class 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
150000002736 metal compounds Chemical class 0.000 description 3
UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 description 3
239000011707 mineral Substances 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
239000004033 plastic Substances 0.000 description 3
229920003023 plastic Polymers 0.000 description 3
NAQMRYXOGZYLMQ-UHFFFAOYSA-N 1-(2-hydroxyethyl)-3,4-dimethylpyrrole-2,5-dione Chemical compound CC1=C(C)C(=O)N(CCO)C1=O NAQMRYXOGZYLMQ-UHFFFAOYSA-N 0.000 description 2
RXMYQVLYLJDJDW-UHFFFAOYSA-N 2-(3,4-dimethyl-2,5-dioxopyrrol-1-yl)ethyl acetate Chemical compound CC(=O)OCCN1C(=O)C(C)=C(C)C1=O RXMYQVLYLJDJDW-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
ZTWMBHJPUJJJME-UHFFFAOYSA-N 3,4-dimethylpyrrole-2,5-dione Chemical compound CC1=C(C)C(=O)NC1=O ZTWMBHJPUJJJME-UHFFFAOYSA-N 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
229920002430 Fibre-reinforced plastic Polymers 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 2
229910000071 diazene Inorganic materials 0.000 description 2
238000007598 dipping method Methods 0.000 description 2
150000002118 epoxides Chemical class 0.000 description 2
WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 2
239000011151 fibre-reinforced plastic Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
238000005470 impregnation Methods 0.000 description 2
239000004922 lacquer Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
239000000178 monomer Substances 0.000 description 2
150000001451 organic peroxides Chemical class 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
229920000058 polyacrylate Polymers 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
229920002635 polyurethane Polymers 0.000 description 2
239000004814 polyurethane Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000010453 quartz Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
238000007789 sealing Methods 0.000 description 2
231100000489 sensitizer Toxicity 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
LUIFEQXXPNBOHZ-UHFFFAOYSA-N 1,2,3,4-tetramethyl-3,4-bis[2-[methyl(dipropoxy)silyl]ethylcarbamoyl]cyclobutane-1,2-dicarboxylic acid Chemical compound CCCO[Si](C)(OCCC)CCNC(=O)C1(C)C(C)(C(O)=O)C(C)(C(O)=O)C1(C)C(=O)NCC[Si](C)(OCCC)OCCC LUIFEQXXPNBOHZ-UHFFFAOYSA-N 0.000 description 1
ZRZHXNCATOYMJH-UHFFFAOYSA-N 1-(chloromethyl)-4-ethenylbenzene Chemical compound ClCC1=CC=C(C=C)C=C1 ZRZHXNCATOYMJH-UHFFFAOYSA-N 0.000 description 1
IRQIACOKCSCFOC-UHFFFAOYSA-N 1-[3-[dichloro(methyl)silyl]propyl]-3,4-dimethylpyrrole-2,5-dione Chemical compound CC1=C(C)C(=O)N(CCC[Si](C)(Cl)Cl)C1=O IRQIACOKCSCFOC-UHFFFAOYSA-N 0.000 description 1
XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 1
GKFUOUFVGNXLDK-UHFFFAOYSA-N 1-ethenyl-3,4-dimethylpyrrole-2,5-dione Chemical compound CC1=C(C)C(=O)N(C=C)C1=O GKFUOUFVGNXLDK-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
BHCIAYOKDSYJBG-UHFFFAOYSA-N 3,4-dimethyl-1-(3-triethoxysilylpropyl)pyrrole-2,5-dione Chemical compound CCO[Si](OCC)(OCC)CCCN1C(=O)C(C)=C(C)C1=O BHCIAYOKDSYJBG-UHFFFAOYSA-N 0.000 description 1
RMOVXCOVNWNMBF-UHFFFAOYSA-N 3,4-dimethyl-1-(3-trimethoxysilylpropyl)pyrrole-2,5-dione Chemical compound CO[Si](OC)(OC)CCCN1C(=O)C(C)=C(C)C1=O RMOVXCOVNWNMBF-UHFFFAOYSA-N 0.000 description 1
BRCVKJSQFCMTDN-UHFFFAOYSA-N 3,4-dimethyl-1-[2-[methyl(dipropoxy)silyl]ethyl]pyrrole-2,5-dione Chemical compound CCCO[Si](C)(OCCC)CCN1C(=O)C(C)=C(C)C1=O BRCVKJSQFCMTDN-UHFFFAOYSA-N 0.000 description 1
IXOHXQXIAOHTSF-UHFFFAOYSA-N 3,4-dimethylpyrrole-2,5-dione;potassium Chemical compound [K].CC1=C(C)C(=O)NC1=O IXOHXQXIAOHTSF-UHFFFAOYSA-N 0.000 description 1
JXINYJDXYHSHJO-UHFFFAOYSA-N 3,4-dimethylpyrrole-2,5-dione;sodium Chemical compound [Na].CC1=C(C)C(=O)NC1=O JXINYJDXYHSHJO-UHFFFAOYSA-N 0.000 description 1
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 1
YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
229910001369 Brass Inorganic materials 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
QQDJJKORRYUXER-UHFFFAOYSA-N C1(C=CC(N1)=O)=O.C[SiH3] Chemical compound C1(C=CC(N1)=O)=O.C[SiH3] QQDJJKORRYUXER-UHFFFAOYSA-N 0.000 description 1
241000238366 Cephalopoda Species 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
229920000877 Melamine resin Polymers 0.000 description 1
229920000914 Metallic fiber Polymers 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
229920002302 Nylon 6,6 Polymers 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000004642 Polyimide Substances 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
230000032683 aging Effects 0.000 description 1
-1 aliphatic radical Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
239000004411 aluminium Substances 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
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
235000019400 benzoyl peroxide Nutrition 0.000 description 1
239000010951 brass Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000000919 ceramic Substances 0.000 description 1
ATMABMRDZYWJJU-UHFFFAOYSA-L chromium(2+);2-methylprop-2-enoate;chloride Chemical compound [Cl-].[Cr+2].CC(=C)C([O-])=O ATMABMRDZYWJJU-UHFFFAOYSA-L 0.000 description 1
239000002131 composite material Substances 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000011889 copper foil Substances 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
125000004956 cyclohexylene group Chemical group 0.000 description 1
KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 description 1
WDSBEYRPPZYNSN-UHFFFAOYSA-N dicyclohexyloxymethylsilane Chemical compound C1CCCCC1OC([SiH3])OC1CCCCC1 WDSBEYRPPZYNSN-UHFFFAOYSA-N 0.000 description 1
239000000539 dimer Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000000806 elastomer Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000011888 foil Substances 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
239000007849 furan resin Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
230000001678 irradiating effect Effects 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
VHWYCFISAQVCCP-UHFFFAOYSA-N methoxymethanol Chemical compound COCO VHWYCFISAQVCCP-UHFFFAOYSA-N 0.000 description 1
VZSYMWXUKVEIHW-UHFFFAOYSA-N methyl(diphenoxy)silane Chemical compound C=1C=CC=CC=1O[SiH](C)OC1=CC=CC=C1 VZSYMWXUKVEIHW-UHFFFAOYSA-N 0.000 description 1
MEWMVMZALMGUJM-UHFFFAOYSA-N methyl(dipropoxy)silane Chemical compound CCCO[SiH](C)OCCC MEWMVMZALMGUJM-UHFFFAOYSA-N 0.000 description 1
239000005048 methyldichlorosilane Substances 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
239000012764 mineral filler Substances 0.000 description 1
239000011490 mineral wool Substances 0.000 description 1
PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
229920003052 natural elastomer Polymers 0.000 description 1
229920001194 natural rubber Polymers 0.000 description 1
239000004745 nonwoven fabric Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000005011 phenolic resin Substances 0.000 description 1
150000003003 phosphines Chemical class 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
239000005020 polyethylene terephthalate Substances 0.000 description 1
229920001721 polyimide Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920001021 polysulfide Polymers 0.000 description 1
239000005077 polysulfide Substances 0.000 description 1
150000008117 polysulfides Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000000197 pyrolysis Methods 0.000 description 1
230000005855 radiation Effects 0.000 description 1
230000011514 reflex Effects 0.000 description 1
239000002990 reinforced plastic Substances 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
239000004576 sand Substances 0.000 description 1
238000010517 secondary reaction Methods 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000010703 silicon Substances 0.000 description 1
150000003377 silicon compounds Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229920003051 synthetic elastomer Polymers 0.000 description 1
239000005061 synthetic rubber Substances 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
229920001187 thermosetting polymer Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
OZWKZRFXJPGDFM-UHFFFAOYSA-N tripropoxysilane Chemical compound CCCO[SiH](OCCC)OCCC OZWKZRFXJPGDFM-UHFFFAOYSA-N 0.000 description 1
229920006305 unsaturated polyester Polymers 0.000 description 1
239000005050 vinyl trichlorosilane Substances 0.000 description 1

CA000401795A 1978-08-30 1982-04-27 Silanes renfermant des groupements imides Expired CA1146560A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000401795A CA1146560A (fr)	1978-08-30	1982-04-27	Silanes renfermant des groupements imides

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
CH915478A CH641470A5 (de)	1978-08-30	1978-08-30	Imidgruppen enthaltende silane.
CH9154/78-0		1978-08-30
CA000334572A CA1140134A (fr)	1978-08-30	1979-08-28	Silanes contenant des groupes imides
CA000401795A CA1146560A (fr)	1978-08-30	1982-04-27	Silanes renfermant des groupements imides

Publications (1)

Publication Number	Publication Date
CA1146560A true CA1146560A (fr)	1983-05-17

Family

ID=27166380

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000401795A Expired CA1146560A (fr)	1978-08-30	1982-04-27	Silanes renfermant des groupements imides

Country Status (1)

Country	Link
CA (1)	CA1146560A (fr)

1982
- 1982-04-27 CA CA000401795A patent/CA1146560A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2000-05-17	MKEX	Expiry

Publication	Publication Date	Title
CA1140134A (fr)	1983-01-25	Silanes contenant des groupes imides
US4301075A (en)	1981-11-17	N-Substituted imides and bis-imides
EP0099268B1 (fr)	1986-01-22	Procédé de fabrication de polymaléimides
JPS6327357B2 (fr)	1988-06-02
US4565873A (en)	1986-01-21	Silanes containing imide groups
CA1111042A (fr)	1981-10-20	Derives d'acides imidyl-phtaliques modifies au silicium
CN108349861B (zh)	2021-07-20	烯基苯氧基取代的1,1-二苯基乙烯、它们的制备方法和它们的用途
CA1146560A (fr)	1983-05-17	Silanes renfermant des groupements imides
CA2043383C (fr)	2000-02-15	Aminohydrocarbylsilanes steriquement empeches et procede de preparation
US3803196A (en)	1974-04-09	Aliphatically unsaturated organopolysiloxanes
US3701795A (en)	1972-10-31	Aliphatically unsaturated amic acid and silylated amic acid
CA1287439C (fr)	1991-08-06	Melanges renfermant des di- ou des polycyanates et des derives de substitution de bicyclo¬2.2.1\|hept-5-ene-2,3-dicarboximides; leur utilisation
CA1115713A (fr)	1982-01-05	Derives d'acide bis-phtalique modifies au silicium
AU2017362594B2 (en)	2021-06-03	Asymmetrically substituted bis-alkenyl diphenyl ethers, their preparation and use
US5331076A (en)	1994-07-19	Siloxane compounds
US5113004A (en)	1992-05-12	Organosilicon compounds
US4127712A (en)	1978-11-28	Phthalic acid diesters or ester-amides substituted by alkenylamino groups
GB2256194A (en)	1992-12-02	Fluorinated n, n-bis-imides
JPH0474190A (ja)	1992-03-09	メルカプト基を有するシラン
JPH0474189A (ja)	1992-03-09	メルカプト基を有するシラン
HK40003788B (en)	2023-02-17	Asymmetrically substituted bis-alkenyl diphenyl ethers, their preparation and use
HK40003788A (en)	2020-04-17	Asymmetrically substituted bis-alkenyl diphenyl ethers, their preparation and use
JPH02255690A (ja)	1990-10-16	α，ω―ビス（アルキルエチニルアリロイルアミド）オリゴシロキサンおよび耐熱性溶融接着剤