CA1072975A - Composes sulfures de type organosilicone, procede pour leur production et leur utilisation comme agents facilitant l'adherence - Google Patents

Composes sulfures de type organosilicone, procede pour leur production et leur utilisation comme agents facilitant l'adherence

Info

Publication number: CA1072975A
Authority: CA; Canada
Prior art keywords: compound; formula; sulphur; general formula; radical
Prior art date: 1976-03-02
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.): Expired

Application number

CA246,979A

Other languages

English (en)

Inventor

Claus-Dietrich Seiler

Hans-Joachim Vahlensieck

Jurgen Amort

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.)

Dynamit Nobel AG

Original Assignee

Dynamit Nobel AG

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.)

1976-03-02

Filing date

1976-03-02

Publication date

1980-03-04

1976-03-02 Application filed by Dynamit Nobel AG filed Critical Dynamit Nobel AG

1976-03-02 Priority to CA246,979A priority Critical patent/CA1072975A/fr

1980-03-04 Application granted granted Critical

1980-03-04 Publication of CA1072975A publication Critical patent/CA1072975A/fr

Status Expired legal-status Critical Current

Links

NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims abstract description 14
239000005864 Sulphur Substances 0.000 title claims abstract description 10
150000003961 organosilicon compounds Chemical class 0.000 title claims abstract description 9
238000000034 method Methods 0.000 title claims description 11
239000002318 adhesion promoter Substances 0.000 title abstract description 4
238000004519 manufacturing process Methods 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 21
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 5
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
125000002993 cycloalkylene group Chemical group 0.000 claims abstract description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 4
125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims abstract 3
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 3
229910052760 oxygen Inorganic materials 0.000 claims abstract 3
239000001301 oxygen Substances 0.000 claims abstract 3
238000006243 chemical reaction Methods 0.000 claims description 12
239000003112 inhibitor Substances 0.000 claims description 9
-1 mercapto compound Chemical class 0.000 claims description 9
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 8
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 7
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 5
150000002148 esters Chemical class 0.000 claims description 4
150000003512 tertiary amines Chemical class 0.000 claims description 4
238000005809 transesterification reaction Methods 0.000 claims description 4
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
150000003058 platinum compounds Chemical class 0.000 claims description 2
238000006116 polymerization reaction Methods 0.000 claims 2
125000003545 alkoxy group Chemical group 0.000 claims 1
125000003368 amide group Chemical group 0.000 claims 1
239000007859 condensation product Substances 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
238000002360 preparation method Methods 0.000 claims 1
SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 abstract 1
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 22
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
229960004337 hydroquinone Drugs 0.000 description 11
239000011521 glass Substances 0.000 description 9
229920005989 resin Polymers 0.000 description 9
239000011347 resin Substances 0.000 description 9
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 7
239000000047 product Substances 0.000 description 7
229910000077 silane Inorganic materials 0.000 description 7
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
229920000642 polymer Polymers 0.000 description 6
238000001816 cooling Methods 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000007788 liquid Substances 0.000 description 5
229940063559 methacrylic acid Drugs 0.000 description 5
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
125000003342 alkenyl group Chemical group 0.000 description 4
238000004508 fractional distillation Methods 0.000 description 4
239000004922 lacquer Substances 0.000 description 4
150000004756 silanes Chemical class 0.000 description 4
QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical class CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 4
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 4
239000008096 xylene Substances 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000000921 elemental analysis Methods 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
150000002739 metals Chemical class 0.000 description 3
238000003756 stirring Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
AYTAKQFHWFYBMA-UHFFFAOYSA-N chromium dioxide Chemical compound O=[Cr]=O AYTAKQFHWFYBMA-UHFFFAOYSA-N 0.000 description 2
239000003365 glass fiber Substances 0.000 description 2
125000005395 methacrylic acid group Chemical group 0.000 description 2
VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000000178 monomer Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
229920003048 styrene butadiene rubber Polymers 0.000 description 2
239000000126 substance Substances 0.000 description 2
YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 2
OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
239000004342 Benzoyl peroxide Substances 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
239000004638 Duroplast Substances 0.000 description 1
229920000965 Duroplast Polymers 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
239000002174 Styrene-butadiene Substances 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 1
229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
229920001893 acrylonitrile styrene Polymers 0.000 description 1
238000007605 air drying Methods 0.000 description 1
239000000956 alloy Substances 0.000 description 1
229910045601 alloy Inorganic materials 0.000 description 1
239000004411 aluminium Substances 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
229940045985 antineoplastic platinum compound Drugs 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000010425 asbestos Substances 0.000 description 1
239000011324 bead Substances 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
238000009835 boiling Methods 0.000 description 1
MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
UOUJSJZBMCDAEU-UHFFFAOYSA-N chromium(3+);oxygen(2-) Chemical class [O-2].[O-2].[O-2].[Cr+3].[Cr+3] UOUJSJZBMCDAEU-UHFFFAOYSA-N 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000002131 composite material Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
229910052593 corundum Inorganic materials 0.000 description 1
239000010431 corundum Substances 0.000 description 1
ZXPDYFSTVHQQOI-UHFFFAOYSA-N diethoxysilane Chemical compound CCO[SiH2]OCC ZXPDYFSTVHQQOI-UHFFFAOYSA-N 0.000 description 1
YQGOWXYZDLJBFL-UHFFFAOYSA-N dimethoxysilane Chemical compound CO[SiH2]OC YQGOWXYZDLJBFL-UHFFFAOYSA-N 0.000 description 1
238000003618 dip coating Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000945 filler Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
235000013980 iron oxide Nutrition 0.000 description 1
VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229940063557 methacrylate Drugs 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920001225 polyester resin Polymers 0.000 description 1
239000004645 polyester resin Substances 0.000 description 1
SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000012779 reinforcing material Substances 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
125000005372 silanol group Chemical group 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000011115 styrene butadiene Substances 0.000 description 1
WTGIOQMHIHCSPZ-UHFFFAOYSA-N sulfanylsilicon Chemical class S[Si] WTGIOQMHIHCSPZ-UHFFFAOYSA-N 0.000 description 1
125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
239000011135 tin Substances 0.000 description 1
239000010936 titanium Substances 0.000 description 1
150000003608 titanium Chemical class 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
UCSBCWBHZLSFGC-UHFFFAOYSA-N tributoxysilane Chemical compound CCCCO[SiH](OCCCC)OCCCC UCSBCWBHZLSFGC-UHFFFAOYSA-N 0.000 description 1
QYBKVVRRGQSGDC-UHFFFAOYSA-N triethyl methyl silicate Chemical compound CCO[Si](OC)(OCC)OCC QYBKVVRRGQSGDC-UHFFFAOYSA-N 0.000 description 1
229920006337 unsaturated polyester resin Polymers 0.000 description 1
UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

CA246,979A 1976-03-02 1976-03-02 Composes sulfures de type organosilicone, procede pour leur production et leur utilisation comme agents facilitant l'adherence Expired CA1072975A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA246,979A CA1072975A (fr)	1976-03-02	1976-03-02	Composes sulfures de type organosilicone, procede pour leur production et leur utilisation comme agents facilitant l'adherence

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA246,979A CA1072975A (fr)	1976-03-02	1976-03-02	Composes sulfures de type organosilicone, procede pour leur production et leur utilisation comme agents facilitant l'adherence

Publications (1)

Publication Number	Publication Date
CA1072975A true CA1072975A (fr)	1980-03-04

Family

ID=4105366

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA246,979A Expired CA1072975A (fr)	1976-03-02	1976-03-02	Composes sulfures de type organosilicone, procede pour leur production et leur utilisation comme agents facilitant l'adherence

Country Status (1)

Country	Link
CA (1)	CA1072975A (fr)

1976
- 1976-03-02 CA CA246,979A patent/CA1072975A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-03-04	MKEX	Expiry

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