CA1152709A - Compositions renfermant des composes cycliques fluoro-silicies pour le traitement des fibres - Google Patents

Compositions renfermant des composes cycliques fluoro-silicies pour le traitement des fibres

Info

Publication number: CA1152709A
Authority: CA; Canada
Prior art keywords: component; silicon; atom; units; radicals
Prior art date: 1981-04-08
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

CA000374941A

Other languages

English (en)

Inventor

Yoshinobu Koda

Isao Ona

Atsushi Takeda

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.)

1981-04-08

Filing date

1981-04-08

Publication date

1983-08-30

1981-04-08 Application filed by Toray Silicone Co Ltd filed Critical Toray Silicone Co Ltd

1981-04-08 Priority to CA000374941A priority Critical patent/CA1152709A/fr

1983-08-30 Application granted granted Critical

1983-08-30 Publication of CA1152709A publication Critical patent/CA1152709A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 40
239000000835 fiber Substances 0.000 title claims abstract description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 22
229920001296 polysiloxane Polymers 0.000 claims abstract description 17
229930195733 hydrocarbon Natural products 0.000 claims abstract description 13
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 12
239000003054 catalyst Substances 0.000 claims abstract description 7
238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 7
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 27
229910052710 silicon Inorganic materials 0.000 claims description 17
125000004122 cyclic group Chemical group 0.000 claims description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 13
229920006136 organohydrogenpolysiloxane Polymers 0.000 claims description 9
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 5
238000009833 condensation Methods 0.000 claims description 5
230000005494 condensation Effects 0.000 claims description 5
ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 3
239000012975 dibutyltin dilaurate Substances 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
239000007788 liquid Substances 0.000 claims description 3
238000002156 mixing Methods 0.000 claims description 3
XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 claims description 2
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 2
TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 2
239000004094 surface-active agent Substances 0.000 claims description 2
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical class [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract description 7
238000006482 condensation reaction Methods 0.000 abstract 1
-1 polysiloxane Polymers 0.000 description 29
239000003921 oil Substances 0.000 description 20
239000004744 fabric Substances 0.000 description 15
239000002657 fibrous material Substances 0.000 description 15
239000000243 solution Substances 0.000 description 11
238000000034 method Methods 0.000 description 10
150000003254 radicals Chemical class 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
235000015067 sauces Nutrition 0.000 description 4
239000002904 solvent Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
239000004745 nonwoven fabric Substances 0.000 description 3
125000004430 oxygen atom Chemical group O* 0.000 description 3
229910000077 silane Inorganic materials 0.000 description 3
210000002268 wool Anatomy 0.000 description 3
XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
240000008415 Lactuca sativa Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
238000004132 cross linking Methods 0.000 description 2
239000003431 cross linking reagent Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
229920005645 diorganopolysiloxane polymer Polymers 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
239000012530 fluid Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
229920000126 latex Polymers 0.000 description 2
239000004816 latex Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
229920000728 polyester Polymers 0.000 description 2
235000012045 salad Nutrition 0.000 description 2
150000004756 silanes Chemical class 0.000 description 2
235000013555 soy sauce Nutrition 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
238000005406 washing Methods 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
240000006240 Linum usitatissimum Species 0.000 description 1
235000004431 Linum usitatissimum Nutrition 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
229920000459 Nitrile rubber Polymers 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
229920000297 Rayon Polymers 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
230000002730 additional effect Effects 0.000 description 1
229940072049 amyl acetate Drugs 0.000 description 1
PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
239000010425 asbestos Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
ZCGHEBMEQXMRQL-UHFFFAOYSA-N benzyl 2-carbamoylpyrrolidine-1-carboxylate Chemical compound NC(=O)C1CCCN1C(=O)OCC1=CC=CC=C1 ZCGHEBMEQXMRQL-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 1
229940043232 butyl acetate Drugs 0.000 description 1
150000001734 carboxylic acid salts Chemical class 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000004205 dimethyl polysiloxane Substances 0.000 description 1
235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
230000000694 effects Effects 0.000 description 1
229940093499 ethyl acetate Drugs 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
238000007654 immersion Methods 0.000 description 1
239000012784 inorganic fiber Substances 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
ZUBZATZOEPUUQF-UHFFFAOYSA-N isopropylhexane Natural products CCCCCCC(C)C ZUBZATZOEPUUQF-UHFFFAOYSA-N 0.000 description 1
238000005461 lubrication Methods 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Substances 0.000 description 1
SGGOJYZMTYGPCH-UHFFFAOYSA-L manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 SGGOJYZMTYGPCH-UHFFFAOYSA-L 0.000 description 1
229940017219 methyl propionate Drugs 0.000 description 1
YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
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 1
125000000962 organic group Chemical group 0.000 description 1
239000011368 organic material Substances 0.000 description 1
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
229940090181 propyl acetate Drugs 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002964 rayon Substances 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
238000007761 roller coating Methods 0.000 description 1
229910052990 silicon hydride Inorganic materials 0.000 description 1
229920005573 silicon-containing polymer Polymers 0.000 description 1
239000010454 slate Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
229920003048 styrene butadiene rubber Polymers 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000012209 synthetic fiber Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical class O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
239000013638 trimer Substances 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
239000002759 woven fabric Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1

Landscapes

Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

CA000374941A 1981-04-08 1981-04-08 Compositions renfermant des composes cycliques fluoro-silicies pour le traitement des fibres Expired CA1152709A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000374941A CA1152709A (fr)	1981-04-08	1981-04-08	Compositions renfermant des composes cycliques fluoro-silicies pour le traitement des fibres

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000374941A CA1152709A (fr)	1981-04-08	1981-04-08	Compositions renfermant des composes cycliques fluoro-silicies pour le traitement des fibres

Publications (1)

Publication Number	Publication Date
CA1152709A true CA1152709A (fr)	1983-08-30

Family

ID=4119677

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000374941A Expired CA1152709A (fr)	1981-04-08	1981-04-08	Compositions renfermant des composes cycliques fluoro-silicies pour le traitement des fibres

Country Status (1)

Country	Link
CA (1)	CA1152709A (fr)

1981
- 1981-04-08 CA CA000374941A patent/CA1152709A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2000-08-30	MKEX	Expiry

Publication	Publication Date	Title
US3876459A (en)	1975-04-08	Treatment of fibres
US4419391A (en)	1983-12-06	Method of imparting improved touch to a fabric
CA1100263A (fr)	1981-05-05	Traduction non-disponible
CA1167585A (fr)	1984-05-15	Substances a base de polysiloxane a groupements organofonctionnels pour le traitement de fibres
CA1244604A (fr)	1988-11-15	Methode de traitement de materiaux a l'aide de composes d'organopolysiloxane
CA1197257A (fr)	1985-11-26	Preparation d'un sel d'ammonium quaternaire de siloxane
CA1188463A (fr)	1985-06-11	Traitement de fibres textiles
US4417024A (en)	1983-11-22	Fluorosilicone-containing compositions for the treatment of fibers
US5300239A (en)	1994-04-05	Water-repellent and oil-repellent treatment
CA2066897C (fr)	2002-05-21	Agent de traitement de fibres
US5126389A (en)	1992-06-30	Silicone rubber composition for treatment of fiber structures
CA1041707A (fr)	1978-11-07	Procede de traitement des fibres
CA1245668A (fr)	1988-11-29	Organopolysiloxannes et leur utilisation pour le traitement des fibres
KR940008993B1 (ko)	1994-09-28	자기가교성 아미노실록산 에멀젼의 제조방법
JPH04106157A (ja)	1992-04-08	撥水，撥油性処理剤
US4421783A (en)	1983-12-20	Process for coating substrates
US3418162A (en)	1968-12-24	Composition of waterproof agent and process for manufacture of waterproof cloth using the same
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US4355149A (en)	1982-10-19	Cyclofluorosilicone-containing compositions for the treatment of fibers
CA1134986A (fr)	1982-11-02	Polymeres d'organosilicium
CA1152709A (fr)	1983-08-30	Compositions renfermant des composes cycliques fluoro-silicies pour le traitement des fibres
JPS584114B2 (ja)	1983-01-25	羊毛を防縮加工するための調製剤
JP2863585B2 (ja)	1999-03-03	繊維用撥水剤
CA1177997A (fr)	1984-11-13	Compositions a base de fluorosilicone pour le traitement des fibres
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