CA2193252C - Methodes pour obtenir des polyether-polyols faiblement insatures - Google Patents

Methodes pour obtenir des polyether-polyols faiblement insatures Download PDF

Info

Publication number: CA2193252C
Authority: CA; Canada
Prior art keywords: polyether; weight percent; block; oxide; polyol
Prior art date: 1995-12-29
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 - Fee Related

Application number

CA 2193252

Other languages

English (en)

Other versions

CA2193252A1 (fr

Inventor

Curtis J. Reichel

Thomas L. Fishback

Gladys M. Aviles

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 Corp

Original Assignee

BASF 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.)

1995-12-29

Filing date

1996-12-17

Publication date

2004-07-06

1996-12-17 Application filed by BASF Corp filed Critical BASF Corp

1997-06-30 Publication of CA2193252A1 publication Critical patent/CA2193252A1/fr

2004-07-06 Application granted granted Critical

2004-07-06 Publication of CA2193252C publication Critical patent/CA2193252C/fr

2016-12-17 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

229920000570 polyether Polymers 0.000 title claims abstract description 233
229920005862 polyol Polymers 0.000 title claims abstract description 157
150000003077 polyols Chemical class 0.000 title claims abstract description 157
239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 126
238000000034 method Methods 0.000 title claims description 78
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims abstract description 137
239000003999 initiator Substances 0.000 claims abstract description 93
239000003054 catalyst Substances 0.000 claims abstract description 90
125000002947 alkylene group Chemical group 0.000 claims abstract description 67
150000001875 compounds Chemical class 0.000 claims abstract description 63
238000004519 manufacturing process Methods 0.000 claims abstract description 54
125000005702 oxyalkylene group Chemical group 0.000 claims abstract description 49
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 82
239000000203 mixture Substances 0.000 claims description 68
125000006353 oxyethylene group Chemical group 0.000 claims description 51
-1 polyoxypropylene Polymers 0.000 claims description 49
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 48
239000012948 isocyanate Substances 0.000 claims description 35
150000002513 isocyanates Chemical class 0.000 claims description 35
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 claims description 21
MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 claims description 14
HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 claims description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
229920001451 polypropylene glycol Polymers 0.000 claims description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
150000004703 alkoxides Chemical class 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 1
239000000565 sealant Substances 0.000 description 56
229920001971 elastomer Polymers 0.000 description 50
239000000806 elastomer Substances 0.000 description 50
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 49
238000006243 chemical reaction Methods 0.000 description 40
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
239000000853 adhesive Substances 0.000 description 34
230000001070 adhesive effect Effects 0.000 description 34
229910052757 nitrogen Inorganic materials 0.000 description 27
150000002009 diols Chemical class 0.000 description 26
235000011118 potassium hydroxide Nutrition 0.000 description 25
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 23
238000002360 preparation method Methods 0.000 description 21
229920000642 polymer Polymers 0.000 description 16
150000004072 triols Chemical class 0.000 description 15
239000004970 Chain extender Substances 0.000 description 14
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 14
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 13
230000002209 hydrophobic effect Effects 0.000 description 13
239000000243 solution Substances 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
125000000746 allylic group Chemical group 0.000 description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 description 12
239000000047 product Substances 0.000 description 12
239000004615 ingredient Substances 0.000 description 11
230000008569 process Effects 0.000 description 11
238000012360 testing method Methods 0.000 description 11
230000002829 reductive effect Effects 0.000 description 10
229920002635 polyurethane Polymers 0.000 description 9
239000004814 polyurethane Substances 0.000 description 9
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
229910052751 metal Inorganic materials 0.000 description 8
239000002184 metal Substances 0.000 description 8
229910052792 caesium Inorganic materials 0.000 description 7
239000005056 polyisocyanate Substances 0.000 description 7
229920001228 polyisocyanate Polymers 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
239000011575 calcium Substances 0.000 description 6
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
239000000945 filler Substances 0.000 description 6
229920003225 polyurethane elastomer Polymers 0.000 description 6
230000009467 reduction Effects 0.000 description 6
238000006722 reduction reaction Methods 0.000 description 6
239000003039 volatile agent Substances 0.000 description 6
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
235000011054 acetic acid Nutrition 0.000 description 5
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 5
230000001419 dependent effect Effects 0.000 description 5
235000011187 glycerol Nutrition 0.000 description 5
230000000379 polymerizing effect Effects 0.000 description 5
238000012545 processing Methods 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000003381 stabilizer Substances 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
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
229920005830 Polyurethane Foam Polymers 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
238000013019 agitation Methods 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
230000008901 benefit Effects 0.000 description 4
230000015556 catabolic process Effects 0.000 description 4
238000006731 degradation reaction Methods 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
150000004679 hydroxides Chemical class 0.000 description 4
BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 4
150000007524 organic acids Chemical class 0.000 description 4
239000011496 polyurethane foam Substances 0.000 description 4
238000010926 purge Methods 0.000 description 4
230000009257 reactivity Effects 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000011734 sodium Substances 0.000 description 4
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
235000011121 sodium hydroxide Nutrition 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
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
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 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
150000004984 aromatic diamines Chemical class 0.000 description 3
229910052788 barium Inorganic materials 0.000 description 3
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
235000013877 carbamide Nutrition 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000004927 clay Substances 0.000 description 3
238000007872 degassing Methods 0.000 description 3
238000009826 distribution Methods 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
239000006260 foam Substances 0.000 description 3
150000002483 hydrogen compounds Chemical class 0.000 description 3
239000011261 inert gas Substances 0.000 description 3
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
235000005985 organic acids Nutrition 0.000 description 3
230000000704 physical effect Effects 0.000 description 3
239000004014 plasticizer Substances 0.000 description 3
229940095050 propylene Drugs 0.000 description 3
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000007787 solid Substances 0.000 description 3
229910052712 strontium Inorganic materials 0.000 description 3
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
230000008961 swelling Effects 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
238000004448 titration Methods 0.000 description 3
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-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
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
229920000265 Polyparaphenylene Polymers 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 2
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
239000006096 absorbing agent Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
150000003868 ammonium compounds Chemical class 0.000 description 2
229910052787 antimony Inorganic materials 0.000 description 2
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
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229910017052 cobalt Inorganic materials 0.000 description 2
239000010941 cobalt Substances 0.000 description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
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125000005442 diisocyanate group Chemical group 0.000 description 2
HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 description 2
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238000010438 heat treatment Methods 0.000 description 2
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
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229910052759 nickel Inorganic materials 0.000 description 2
125000002524 organometallic group Chemical group 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
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229910052701 rubidium Inorganic materials 0.000 description 2
IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 2
150000003335 secondary amines Chemical group 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
238000001179 sorption measurement Methods 0.000 description 2
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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 2
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
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125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 1
ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 description 1
GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 1
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WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 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
150000002736 metal compounds Chemical class 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical group OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000013008 moisture curing Methods 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
XFLSMWXCZBIXLV-UHFFFAOYSA-N n,n-dimethyl-2-(4-methylpiperazin-1-yl)ethanamine Chemical compound CN(C)CCN1CCN(C)CC1 XFLSMWXCZBIXLV-UHFFFAOYSA-N 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
150000002924 oxiranes Chemical group 0.000 description 1
VPPWQRIBARKZNY-UHFFFAOYSA-N oxo(diphenyl)tin Chemical compound C=1C=CC=CC=1[Sn](=O)C1=CC=CC=C1 VPPWQRIBARKZNY-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
230000035699 permeability Effects 0.000 description 1
125000005498 phthalate group Chemical class 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
229920002857 polybutadiene Polymers 0.000 description 1
229920001610 polycaprolactone Polymers 0.000 description 1
229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000011253 protective coating Substances 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
238000010107 reaction injection moulding Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000001846 repelling effect Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
239000004576 sand Substances 0.000 description 1
150000005619 secondary aliphatic amines Chemical class 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000014347 soups Nutrition 0.000 description 1
239000004575 stone Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003871 sulfonates Chemical class 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
239000004753 textile Substances 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
239000012974 tin catalyst Substances 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
150000004998 toluenediamines Chemical class 0.000 description 1
GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000004078 waterproofing Methods 0.000 description 1
238000005303 weighing Methods 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
229910052726 zirconium Inorganic materials 0.000 description 1

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Polyethers (AREA)

CA 2193252 1995-12-29 1996-12-17 Methodes pour obtenir des polyether-polyols faiblement insatures Expired - Fee Related CA2193252C (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date
US941295P	1995-12-29	1995-12-29
US60/009,412		1995-12-29
US75457596A	1996-11-21	1996-11-21
US08/754,575		1996-11-21

Publications (2)

Publication Number	Publication Date
CA2193252A1 CA2193252A1 (fr)	1997-06-30
CA2193252C true CA2193252C (fr)	2004-07-06

Family

ID=32684385

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2193252 Expired - Fee Related CA2193252C (fr)	1995-12-29	1996-12-17	Methodes pour obtenir des polyether-polyols faiblement insatures

Country Status (1)

Country	Link
CA (1)	CA2193252C (fr)

1996
- 1996-12-17 CA CA 2193252 patent/CA2193252C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2193252A1 (fr)	1997-06-30
MX9606314A (es)	1997-10-31

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Date	Code	Title	Description
2000-12-08	EEER	Examination request
2016-01-28	MKLA	Lapsed	Effective date: 20151217

Publication	Publication Date	Title
US6103850A (en)	2000-08-15	Sealants made using low unsaturation polyoxyalkylene polyether polyols
KR100259667B1 (ko)	2000-06-15	경질 열가소성 폴리우레탄 탄성중합체 및 이의 제조방법
US5136010A (en)	1992-08-04	Polyurethane elastomers and polyurea elastomers made using high functionality, low unsaturation level polyols prepared with double metal cyanide catalysts
US5096993A (en)	1992-03-17	Thermoplastic polyurethane elastomers and polyurea elastomers made using low unsaturation level polyols prepared with double metal cyanide catalysts
US4985491A (en)	1991-01-15	Polyurethane sealants made using high molecular weight polyols prepared with double metal cyanide catalysts
US5116931A (en)	1992-05-26	Thermoset polyurethane elastomers and polyurea elastomers made using high functionality, low unsaturation level polyols prepared with double metal cyanide catalysts
US5185420A (en)	1993-02-09	Thermoplastic polyurethane elastomers and polyurea elastomers made using low unsaturation level polyols prepared with double metal cyanide catalysts
US5266681A (en)	1993-11-30	Process and composition for providing double metal cyanide catalyzed polyols having enhanced reactivity
CA2204426C (fr)	2009-07-14	Compositions d'ether de polytetramethyleneglycols et de polyoxyalkylene-polyether-polyols, peu insaturees
EP0573206B1 (fr)	1998-08-26	Compositions de polyuréthane durcissant à l'humidité et une méthode pour les préparer par durcissement des prépolymères ayant des groupes terminaux isocyanates
EP0372561A2 (fr)	1990-06-13	Composition de résine durcissable par l'humidité
US6040413A (en)	2000-03-21	Composition of polytetramethylene ether glycols and polyoxy alkylene polyether polyols having a low degree of unsaturation
EP0781791B1 (fr)	1998-07-22	Polyétherpolyol de polyoxyalkylène avec un faible taux d'insaturation
CA2193252C (fr)	2004-07-06	Methodes pour obtenir des polyether-polyols faiblement insatures
CN1200740A (zh)	1998-12-02	聚四亚甲基醚二醇和具有低不饱和度的聚氧化烯聚醚多醇的组合物
US5357038A (en)	1994-10-18	Process and composition for providing double metal cyanide catalyzed polyols having enhanced reactivity
MXPA96006467A (en)	1997-06-01	Low insaturac polioxylquylene polyethyl polyoles
MXPA96006314A (en)	1998-07-03	Method for manufacturing polyolet polyoles from bajainsaturac
MXPA96006468A (en)	2000-08-01	Fabricated sealant compounds using low insaturac polioxylycylene polyethylene polyetholes
US6077926A (en)	2000-06-20	Physical properties of sealants using polyols with reduced unsaturation
MXPA96006266A (en)	2002-07-25	Isocyanate or hydroxyl terminated prepolymers made with low unsaturation polyoxyalkylene polyether polyols
WO2008074907A1 (fr)	2008-06-26	Nouveaux polyols réactifs
US20060281894A1 (en)	2006-12-14	Method of forming polyetherols in the presence of aluminum phosphate catalysts
CA2193254A1 (fr)	1997-06-30	Polyoxyalkylene-polyether-polyols faiblement insatures
JPH07206965A (ja)	1995-08-08	ポリウレタン系硬化性組成物