CA1114829A - Polyethersiloxanes termines par des groupements acrylonitriles - Google Patents

Polyethersiloxanes termines par des groupements acrylonitriles

Info

Publication number: CA1114829A
Authority: CA; Canada
Prior art keywords: acrylonitrile; foam; grams; reaction; average
Prior art date: 1975-10-30
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

CA359,066A

Other languages

English (en)

Inventor

Bernard Kanner

Bela Prokai

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.)

Union Carbide Corp

Original Assignee

Union Carbide Corp

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.)

1975-10-30

Filing date

1980-08-26

Publication date

1981-12-22

1975-10-30 Priority claimed from US05/627,251 external-priority patent/US4043951A/en

1980-08-26 Application filed by Union Carbide Corp filed Critical Union Carbide Corp

1980-08-26 Priority to CA359,066A priority Critical patent/CA1114829A/fr

1981-12-22 Application granted granted Critical

1981-12-22 Publication of CA1114829A publication Critical patent/CA1114829A/fr

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims abstract description 51
239000000203 mixture Substances 0.000 claims description 131
-1 alkylene radical Chemical class 0.000 claims description 110
125000004432 carbon atom Chemical group C* 0.000 claims description 22
RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical group [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims 1
229920000642 polymer Polymers 0.000 abstract description 108
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract description 33
239000003063 flame retardant Substances 0.000 abstract description 27
RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 abstract description 21
238000002360 preparation method Methods 0.000 abstract description 9
230000001413 cellular effect Effects 0.000 abstract description 6
239000006260 foam Substances 0.000 description 118
239000000047 product Substances 0.000 description 98
238000006243 chemical reaction Methods 0.000 description 80
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 76
235000013350 formula milk Nutrition 0.000 description 74
239000011541 reaction mixture Substances 0.000 description 70
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 69
239000004094 surface-active agent Substances 0.000 description 63
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 52
229920000570 polyether Polymers 0.000 description 52
229920005862 polyol Polymers 0.000 description 52
239000004721 Polyphenylene oxide Substances 0.000 description 51
239000003054 catalyst Substances 0.000 description 50
150000003077 polyols Chemical class 0.000 description 48
229920001296 polysiloxane Polymers 0.000 description 46
239000000376 reactant Substances 0.000 description 42
239000000306 component Substances 0.000 description 39
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
101150065749 Churc1 gene Proteins 0.000 description 34
102100038239 Protein Churchill Human genes 0.000 description 34
229910052697 platinum Inorganic materials 0.000 description 34
229920000728 polyester Polymers 0.000 description 34
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
238000000034 method Methods 0.000 description 33
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 32
229960005088 urethane Drugs 0.000 description 32
125000002887 hydroxy group Chemical group [H]O* 0.000 description 31
239000001257 hydrogen Substances 0.000 description 30
229910052739 hydrogen Inorganic materials 0.000 description 30
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 25
238000004458 analytical method Methods 0.000 description 24
150000001412 amines Chemical class 0.000 description 23
229920005906 polyester polyol Polymers 0.000 description 23
229920001228 polyisocyanate Polymers 0.000 description 22
239000005056 polyisocyanate Substances 0.000 description 22
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 21
239000000706 filtrate Substances 0.000 description 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 21
238000002390 rotary evaporation Methods 0.000 description 21
125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 21
239000000243 solution Substances 0.000 description 21
239000002253 acid Substances 0.000 description 20
238000009472 formulation Methods 0.000 description 18
239000012530 fluid Substances 0.000 description 17
SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 16
239000007788 liquid Substances 0.000 description 16
239000011496 polyurethane foam Substances 0.000 description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 15
229920005830 Polyurethane Foam Polymers 0.000 description 15
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 14
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 14
150000003254 radicals Chemical class 0.000 description 14
239000007858 starting material Substances 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
239000004604 Blowing Agent Substances 0.000 description 13
150000002500 ions Chemical class 0.000 description 13
238000004519 manufacturing process Methods 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 12
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 12
125000002947 alkylene group Chemical group 0.000 description 12
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
238000005227 gel permeation chromatography Methods 0.000 description 12
150000007513 acids Chemical class 0.000 description 11
125000000217 alkyl group Chemical group 0.000 description 11
238000005187 foaming Methods 0.000 description 11
229910052710 silicon Inorganic materials 0.000 description 11
239000003381 stabilizer Substances 0.000 description 11
238000003756 stirring Methods 0.000 description 11
229910020447 SiO2/2 Inorganic materials 0.000 description 10
239000002904 solvent Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
239000003377 acid catalyst Substances 0.000 description 9
239000000460 chlorine Substances 0.000 description 9
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
238000006459 hydrosilylation reaction Methods 0.000 description 8
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 8
239000012948 isocyanate Substances 0.000 description 8
150000002513 isocyanates Chemical class 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
229910020485 SiO4/2 Inorganic materials 0.000 description 7
230000002378 acidificating effect Effects 0.000 description 7
150000002334 glycols Chemical class 0.000 description 7
239000000463 material Substances 0.000 description 7
229920002635 polyurethane Polymers 0.000 description 7
239000004814 polyurethane Substances 0.000 description 7
239000000523 sample Substances 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
239000000654 additive Substances 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 6
229940051250 hexylene glycol Drugs 0.000 description 6
125000001261 isocyanato group Chemical group *N=C=O 0.000 description 6
239000002736 nonionic surfactant Substances 0.000 description 6
125000006353 oxyethylene group Chemical group 0.000 description 6
229910052698 phosphorus Inorganic materials 0.000 description 6
239000011574 phosphorus Substances 0.000 description 6
239000010703 silicon Substances 0.000 description 6
239000011734 sodium Substances 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
239000000126 substance Substances 0.000 description 6
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
239000005977 Ethylene Substances 0.000 description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
125000004429 atom Chemical group 0.000 description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
125000005442 diisocyanate group Chemical group 0.000 description 5
239000007789 gas Substances 0.000 description 5
229910052736 halogen Inorganic materials 0.000 description 5
150000002367 halogens Chemical class 0.000 description 5
229930195733 hydrocarbon Natural products 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
125000004430 oxygen atom Chemical group O* 0.000 description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
239000003340 retarding agent Substances 0.000 description 5
150000005846 sugar alcohols Polymers 0.000 description 5
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 5
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
239000004215 Carbon black (E152) Substances 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
125000001931 aliphatic group Chemical group 0.000 description 4
239000002585 base Substances 0.000 description 4
238000007664 blowing Methods 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 4
238000010828 elution Methods 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
239000004872 foam stabilizing agent Substances 0.000 description 4
150000002430 hydrocarbons Chemical class 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
238000002156 mixing Methods 0.000 description 4
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
229920005573 silicon-containing polymer Polymers 0.000 description 4
239000000600 sorbitol Substances 0.000 description 4
230000000087 stabilizing effect Effects 0.000 description 4
239000003784 tall oil Substances 0.000 description 4
238000012360 testing method Methods 0.000 description 4
RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 4
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
150000003673 urethanes Chemical class 0.000 description 4
239000008096 xylene Substances 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000007983 Tris buffer Substances 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
125000000129 anionic group Chemical group 0.000 description 3
239000003945 anionic surfactant Substances 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
238000011088 calibration curve Methods 0.000 description 3
150000001735 carboxylic acids Chemical class 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
125000004093 cyano group Chemical group *C#N 0.000 description 3
238000007278 cyanoethylation reaction Methods 0.000 description 3
239000000539 dimer Substances 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
125000001183 hydrocarbyl group Chemical group 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
239000000178 monomer Substances 0.000 description 3
150000002894 organic compounds Chemical class 0.000 description 3
125000005702 oxyalkylene group Chemical group 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
150000002989 phenols Chemical class 0.000 description 3
238000012545 processing Methods 0.000 description 3
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
229920005989 resin Chemical class 0.000 description 3
239000011347 resin Chemical class 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 3
229940113165 trimethylolpropane Drugs 0.000 description 3
ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 2
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
KXCSSLSUIHCPQH-UHFFFAOYSA-N 1-isocyanato-3-(3-isocyanatopropoxy)propane Chemical compound O=C=NCCCOCCCN=C=O KXCSSLSUIHCPQH-UHFFFAOYSA-N 0.000 description 2
CHUGKEQJSLOLHL-UHFFFAOYSA-N 2,2-Bis(bromomethyl)propane-1,3-diol Chemical compound OCC(CO)(CBr)CBr CHUGKEQJSLOLHL-UHFFFAOYSA-N 0.000 description 2
BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 description 2
HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 2
241000331231 Amorphocerini gen. n. 1 DAD-2008 Species 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
QHWKHLYUUZGSCW-UHFFFAOYSA-N Tetrabromophthalic anhydride Chemical compound BrC1=C(Br)C(Br)=C2C(=O)OC(=O)C2=C1Br QHWKHLYUUZGSCW-UHFFFAOYSA-N 0.000 description 2
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
125000002015 acyclic group Chemical group 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
230000002411 adverse Effects 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
125000000732 arylene group Chemical group 0.000 description 2
238000009835 boiling Methods 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical class OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
125000002091 cationic group Chemical group 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
238000002845 discoloration Methods 0.000 description 2
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230000007935 neutral effect Effects 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
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150000002825 nitriles Chemical class 0.000 description 1
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229920003986 novolac Polymers 0.000 description 1
BCCOBQSFUDVTJQ-UHFFFAOYSA-N octafluorocyclobutane Chemical compound FC1(F)C(F)(F)C(F)(F)C1(F)F BCCOBQSFUDVTJQ-UHFFFAOYSA-N 0.000 description 1
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150000002943 palmitic acids Chemical class 0.000 description 1
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125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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229920002239 polyacrylonitrile Polymers 0.000 description 1
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239000004645 polyester resin Substances 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
239000002952 polymeric resin Substances 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
229920001843 polymethylhydrosiloxane Polymers 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
239000011148 porous material Substances 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
FQLQNUZHYYPPBT-UHFFFAOYSA-N potassium;azane Chemical compound N.[K+] FQLQNUZHYYPPBT-UHFFFAOYSA-N 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
239000001294 propane Substances 0.000 description 1
YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000000979 retarding effect Effects 0.000 description 1
WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
229960003656 ricinoleic acid Drugs 0.000 description 1
FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
150000004756 silanes Chemical class 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
239000002002 slurry Substances 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
HJHVQCXHVMGZNC-JCJNLNMISA-M sodium;(2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoate Chemical compound [Na+].O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C([O-])=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C HJHVQCXHVMGZNC-JCJNLNMISA-M 0.000 description 1
241000894007 species Species 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
238000003860 storage Methods 0.000 description 1
150000003442 suberic acids Chemical class 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
KCNSDMPZCKLTQP-UHFFFAOYSA-N tetraphenylen-1-ol Chemical class C12=CC=CC=C2C2=CC=CC=C2C2=CC=CC=C2C2=C1C=CC=C2O KCNSDMPZCKLTQP-UHFFFAOYSA-N 0.000 description 1
239000004753 textile Substances 0.000 description 1
229910001887 tin oxide Inorganic materials 0.000 description 1
QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical class [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 1
125000005628 tolylene group Chemical group 0.000 description 1
PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
229940087291 tridecyl alcohol Drugs 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1
239000013638 trimer Substances 0.000 description 1
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
150000004072 triols Chemical class 0.000 description 1
JZZBTMVTLBHJHL-UHFFFAOYSA-N tris(2,3-dichloropropyl) phosphate Chemical compound ClCC(Cl)COP(=O)(OCC(Cl)CCl)OCC(Cl)CCl JZZBTMVTLBHJHL-UHFFFAOYSA-N 0.000 description 1
SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1

Landscapes

Silicon Polymers (AREA)

CA359,066A 1975-10-30 1980-08-26 Polyethersiloxanes termines par des groupements acrylonitriles Expired CA1114829A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA359,066A CA1114829A (fr)	1975-10-30	1980-08-26	Polyethersiloxanes termines par des groupements acrylonitriles

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US627,251		1975-10-30
US05/627,251 US4043951A (en)	1975-10-30	1975-10-30	Acrylonitrile-capped polyether-siloxane
CA263,739A CA1090800A (fr)	1975-10-30	1976-10-20	Polyethersiloxanes termines par l'acrylonitrile
CA359,066A CA1114829A (fr)	1975-10-30	1980-08-26	Polyethersiloxanes termines par des groupements acrylonitriles

Publications (1)

Publication Number	Publication Date
CA1114829A true CA1114829A (fr)	1981-12-22

Family

ID=27164707

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA359,066A Expired CA1114829A (fr)	1975-10-30	1980-08-26	Polyethersiloxanes termines par des groupements acrylonitriles

Country Status (1)

Country	Link
CA (1)	CA1114829A (fr)

1980
- 1980-08-26 CA CA359,066A patent/CA1114829A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-12-22	MKEX	Expiry

Publication	Publication Date	Title
US3980688A (en)	1976-09-14	Polysiloxane-polyoxyalkylene block copolymers
CA1169200A (fr)	1984-06-12	Emploi de substances a base d'organosiloxane comme stabilisateurs des mousses souples de polyesters- polyurethanne
US3686254A (en)	1972-08-22	Siloxane-polyoxyalkylene block copolymers
US4025456A (en)	1977-05-24	Polysiloxane-polyoxyalkylene block copolymers
US5472987A (en)	1995-12-05	Surfactant composition for flexible polyurethane foam
US3846462A (en)	1974-11-05	Organosilicone polymers
US3796676A (en)	1974-03-12	Organosilicone polymeric foam stabilizer composition and polyester urethane foam produced therewith
US3384599A (en)	1968-05-21	Siloxane-polyol compositions and process therefor
CA1076574A (fr)	1980-04-29	Copolymeres de polysiloxane-polyoxyalcylene modifies par des groupements morpholino; leur emploi comme stabilisants de mousses
US4031044A (en)	1977-06-21	Polyether based, high resilient polyurethane foam
US3793300A (en)	1974-02-19	Flexible polyester urethane foams using liquid siloxane-oxyalkylene polymeric foam stabilizers
CA1055508A (fr)	1979-05-29	Polymeres de type organosilicone a groupes sulfolanyles
US3887601A (en)	1975-06-03	Organosilicone polymers
US4107068A (en)	1978-08-15	Acrylonitrile-capped polyether-siloxanes
US3793360A (en)	1974-02-19	Organosilicone polymers
US3954824A (en)	1976-05-04	Organosilicone polymers and polyester urethane foam produced therewith
US3833512A (en)	1974-09-03	Solution compositions of organo-silicone polymers
US3979419A (en)	1976-09-07	Cyano-ether polysiloxane-polyoxyalkylene copolymers
CA1114829A (fr)	1981-12-22	Polyethersiloxanes termines par des groupements acrylonitriles
CA1075256A (fr)	1980-04-08	Polymeres d'organosilicone et mousse de polyetherurethanne qui en derive
US4014825A (en)	1977-03-29	Tertiary alcohol-bearing organosilicone polymers
US4058493A (en)	1977-11-15	Polyester urethane foam produced with cyano-ether polysiloxane-polyoxyalkylene copolymers
US4016000A (en)	1977-04-05	Organosilicone polymer solutions
US4031042A (en)	1977-06-21	Organosilicone polymers and polyester urethane foam produced therewith
US4045381A (en)	1977-08-30	Organosilicone polymers