CA2193253A1 - Prepolymeres a base de polyoxyalkylene-polyether-polyols faiblement insatures, termines par un groupe isocyanate ou hydroxyle - Google Patents

Prepolymeres a base de polyoxyalkylene-polyether-polyols faiblement insatures, termines par un groupe isocyanate ou hydroxyle

Info

Publication number: CA2193253A1
Authority: CA; Canada
Prior art keywords: block; groups; polyether; unsaturation; prepolymer
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.): Abandoned

Application number

CA 2193253

Other languages

English (en)

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

1997-06-30

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

1997-06-30 Publication of CA2193253A1 publication Critical patent/CA2193253A1/fr

Status Abandoned legal-status Critical Current

Links

229920000570 polyether Polymers 0.000 title claims abstract description 213
229920005862 polyol Polymers 0.000 title claims abstract description 154
150000003077 polyols Chemical class 0.000 title claims abstract description 153
239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 129
239000012948 isocyanate Substances 0.000 title claims abstract description 27
150000002513 isocyanates Chemical class 0.000 title claims abstract description 27
125000002887 hydroxy group Chemical group [H]O* 0.000 title claims abstract description 21
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims abstract description 73
239000003999 initiator Substances 0.000 claims abstract description 67
125000002947 alkylene group Chemical group 0.000 claims abstract description 65
239000000203 mixture Substances 0.000 claims abstract description 58
-1 oxypropylene groups Chemical group 0.000 claims abstract description 57
150000001875 compounds Chemical class 0.000 claims abstract description 54
125000005702 oxyalkylene group Chemical group 0.000 claims abstract description 47
150000002009 diols Chemical class 0.000 claims abstract description 39
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims abstract description 27
239000005056 polyisocyanate Substances 0.000 claims abstract description 6
229920001228 polyisocyanate Polymers 0.000 claims abstract description 5
125000006353 oxyethylene group Chemical group 0.000 claims description 30
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 8
239000007795 chemical reaction product Substances 0.000 claims description 3
230000007812 deficiency Effects 0.000 claims 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 84
239000003054 catalyst Substances 0.000 description 71
239000000565 sealant Substances 0.000 description 46
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 44
238000000034 method Methods 0.000 description 40
241000282320 Panthera leo Species 0.000 description 33
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
239000000853 adhesive Substances 0.000 description 32
230000001070 adhesive effect Effects 0.000 description 32
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
229910052757 nitrogen Inorganic materials 0.000 description 28
235000011118 potassium hydroxide Nutrition 0.000 description 28
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 23
HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 17
229920000642 polymer Polymers 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 15
150000004072 triols Chemical class 0.000 description 15
229910052792 caesium Inorganic materials 0.000 description 14
229920001971 elastomer Polymers 0.000 description 14
239000000806 elastomer Substances 0.000 description 14
239000000047 product Substances 0.000 description 14
RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical group CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 13
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 13
238000012360 testing method Methods 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
150000002500 ions Chemical class 0.000 description 12
239000000243 solution Substances 0.000 description 12
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 11
230000008569 process Effects 0.000 description 11
239000002253 acid Substances 0.000 description 10
230000002829 reductive effect Effects 0.000 description 10
125000000746 allylic group Chemical group 0.000 description 8
229910052751 metal Inorganic materials 0.000 description 8
239000002184 metal Substances 0.000 description 8
MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 7
239000004970 Chain extender Substances 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
239000006260 foam Substances 0.000 description 6
125000004435 hydrogen atom Chemical group [H]* 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
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
239000000945 filler Substances 0.000 description 5
230000009467 reduction Effects 0.000 description 5
239000002904 solvent Substances 0.000 description 5
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
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 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
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
150000004703 alkoxides Chemical class 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
235000013877 carbamide Nutrition 0.000 description 4
235000011187 glycerol Nutrition 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
238000004519 manufacturing process Methods 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
229920001451 polypropylene glycol Polymers 0.000 description 4
229910052700 potassium Inorganic materials 0.000 description 4
239000011591 potassium Substances 0.000 description 4
230000009257 reactivity Effects 0.000 description 4
229910052708 sodium Inorganic materials 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
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 3
YFONKFDEZLYQDH-OPQQBVKSSA-N N-[(1R,2S)-2,6-dimethyindan-1-yl]-6-[(1R)-1-fluoroethyl]-1,3,5-triazine-2,4-diamine Chemical compound C[C@@H](F)C1=NC(N)=NC(N[C@H]2C3=CC(C)=CC=C3C[C@@H]2C)=N1 YFONKFDEZLYQDH-OPQQBVKSSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
238000013019 agitation Methods 0.000 description 3
125000000217 alkyl group Chemical group 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
230000008901 benefit Effects 0.000 description 3
239000004305 biphenyl Substances 0.000 description 3
239000004202 carbamide 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
239000010949 copper Substances 0.000 description 3
AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 3
HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 description 3
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
239000007789 gas Substances 0.000 description 3
150000004679 hydroxides Chemical class 0.000 description 3
239000011261 inert gas Substances 0.000 description 3
230000014759 maintenance of location Effects 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
238000010926 purge Methods 0.000 description 3
150000003839 salts Chemical class 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
150000003512 tertiary amines Chemical class 0.000 description 3
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
241001136792 Alle Species 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
241000736839 Chara Species 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
229920000265 Polyparaphenylene Polymers 0.000 description 2
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-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
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
125000000129 anionic group Chemical group 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
OIPMQULDKWSNGX-UHFFFAOYSA-N bis[[ethoxy(oxo)phosphaniumyl]oxy]alumanyloxy-ethoxy-oxophosphanium Chemical compound [Al+3].CCO[P+]([O-])=O.CCO[P+]([O-])=O.CCO[P+]([O-])=O OIPMQULDKWSNGX-UHFFFAOYSA-N 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000011575 calcium Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
125000002091 cationic group Chemical group 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
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
229910052802 copper Inorganic materials 0.000 description 2
238000004132 cross linking Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
239000012975 dibutyltin dilaurate Substances 0.000 description 2
238000009826 distribution Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000002118 epoxides Chemical group 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
150000002483 hydrogen compounds Chemical class 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
229920005906 polyester polyol Polymers 0.000 description 2
229920000582 polyisocyanurate Polymers 0.000 description 2
239000011495 polyisocyanurate Substances 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
229910052701 rubidium Inorganic materials 0.000 description 2
IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
238000003860 storage Methods 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
230000008961 swelling Effects 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
229910001887 tin oxide Inorganic materials 0.000 description 2
IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 2
SYRHIZPPCHMRIT-UHFFFAOYSA-N tin(4+) Chemical class [Sn+4] SYRHIZPPCHMRIT-UHFFFAOYSA-N 0.000 description 2
239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 1
229940058015 1,3-butylene glycol Drugs 0.000 description 1
125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
RZTDESRVPFKCBH-UHFFFAOYSA-N 1-methyl-4-(4-methylphenyl)benzene Chemical group C1=CC(C)=CC=C1C1=CC=C(C)C=C1 RZTDESRVPFKCBH-UHFFFAOYSA-N 0.000 description 1
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
CVFRFSNPBJUQMG-UHFFFAOYSA-N 2,3-bis(2-hydroxyethyl)benzene-1,4-diol Chemical compound OCCC1=C(O)C=CC(O)=C1CCO CVFRFSNPBJUQMG-UHFFFAOYSA-N 0.000 description 1
STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
AGIBHMPYXXPGAX-UHFFFAOYSA-N 2-(iodomethyl)oxirane Chemical compound ICC1CO1 AGIBHMPYXXPGAX-UHFFFAOYSA-N 0.000 description 1
WHNBDXQTMPYBAT-UHFFFAOYSA-N 2-butyloxirane Chemical compound CCCCC1CO1 WHNBDXQTMPYBAT-UHFFFAOYSA-N 0.000 description 1
NPRYHWFMGPYJIY-UHFFFAOYSA-N 2-cyclohexyloxirane Chemical compound C1OC1C1CCCCC1 NPRYHWFMGPYJIY-UHFFFAOYSA-N 0.000 description 1
SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 1
AAMHBRRZYSORSH-UHFFFAOYSA-N 2-octyloxirane Chemical compound CCCCCCCCC1CO1 AAMHBRRZYSORSH-UHFFFAOYSA-N 0.000 description 1
BPPVUXSMLBXYGG-UHFFFAOYSA-N 4-[3-(4,5-dihydro-1,2-oxazol-3-yl)-2-methyl-4-methylsulfonylbenzoyl]-2-methyl-1h-pyrazol-3-one Chemical compound CC1=C(C(=O)C=2C(N(C)NC=2)=O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 BPPVUXSMLBXYGG-UHFFFAOYSA-N 0.000 description 1
GJEZBVHHZQAEDB-UHFFFAOYSA-N 6-oxabicyclo[3.1.0]hexane Chemical compound C1CCC2OC21 GJEZBVHHZQAEDB-UHFFFAOYSA-N 0.000 description 1
208000004998 Abdominal Pain Diseases 0.000 description 1
240000000662 Anethum graveolens Species 0.000 description 1
101100188551 Arabidopsis thaliana OCT2 gene Proteins 0.000 description 1
XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
241000726103 Atta Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241001091551 Clio Species 0.000 description 1
208000002881 Colic Diseases 0.000 description 1
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238000002360 preparation method Methods 0.000 description 1
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239000000454 talc Substances 0.000 description 1
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
239000012974 tin catalyst Substances 0.000 description 1
239000010936 titanium Substances 0.000 description 1
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OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
238000004448 titration Methods 0.000 description 1
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 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
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
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Landscapes

Polyethers (AREA)

CA 2193253 1995-12-29 1996-12-17 Prepolymeres a base de polyoxyalkylene-polyether-polyols faiblement insatures, termines par un groupe isocyanate ou hydroxyle Abandoned CA2193253A1 (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date
US930495P	1995-12-29	1995-12-29
US60/009,304		1995-12-29
US75468396A	1996-11-21	1996-11-21
US08/754,683		1996-11-21

Publications (1)

Publication Number	Publication Date
CA2193253A1 true CA2193253A1 (fr)	1997-06-30

Family

ID=26679308

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2193253 Abandoned CA2193253A1 (fr)	1995-12-29	1996-12-17	Prepolymeres a base de polyoxyalkylene-polyether-polyols faiblement insatures, termines par un groupe isocyanate ou hydroxyle

Country Status (1)

Country	Link
CA (1)	CA2193253A1 (fr)

1996
- 1996-12-17 CA CA 2193253 patent/CA2193253A1/fr not_active Abandoned

Legal Events

Date	Code	Title	Description
2000-12-08	EEER	Examination request
2005-05-30	FZDE	Dead

Publication	Publication Date	Title
US6103850A (en)	2000-08-15	Sealants made using low unsaturation polyoxyalkylene polyether polyols
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
EP0416819B1 (fr)	1996-05-22	Elastomères de polyurées aliphatiques pour pulvérisation
KR100259667B1 (ko)	2000-06-15	경질 열가소성 폴리우레탄 탄성중합체 및 이의 제조방법
US5185420A (en)	1993-02-09	Thermoplastic polyurethane elastomers and polyurea elastomers made using low unsaturation level polyols prepared with double metal cyanide catalysts
US5068304A (en)	1991-11-26	Moisture-curable resin composition
US4581470A (en)	1986-04-08	Novel polyols and uses thereof
US5266681A (en)	1993-11-30	Process and composition for providing double metal cyanide catalyzed polyols having enhanced reactivity
EP0420420A2 (fr)	1991-04-03	Elastomère de polyurée pulvérisable et coulable
US5998574A (en)	1999-12-07	Compositions of polytetramethylene ether glycols and polyoxy alkylene polyether polyols having a low degree of unsaturation
EP0139212B2 (fr)	1992-03-25	Compositions de polyols compatibles
US4448905A (en)	1984-05-15	Alcohol substituted amides as chain extenders for polyurethanes
EP0564453B1 (fr)	1997-05-21	Polymeres de polyurethane a module de flexion eleve et procedes de moulage reactif par injection employant lesdits polymeres
US6040413A (en)	2000-03-21	Composition of polytetramethylene ether glycols and polyoxy alkylene polyether polyols having a low degree of unsaturation
US5122548A (en)	1992-06-16	Elastomeric polyisocyanate-based polymers from polyoxyalkylene polyols containing internal polyoxyethylene blocks
EP0420426A2 (fr)	1991-04-03	Elastomère de polyurée pulvérisable et coulable
EP0781791B1 (fr)	1998-07-22	Polyétherpolyol de polyoxyalkylène avec un faible taux d'insaturation
CA2193253A1 (fr)	1997-06-30	Prepolymeres a base de polyoxyalkylene-polyether-polyols faiblement insatures, termines par un groupe isocyanate ou hydroxyle
CA2193252C (fr)	2004-07-06	Methodes pour obtenir des polyether-polyols faiblement insatures
CA2193254A1 (fr)	1997-06-30	Polyoxyalkylene-polyether-polyols faiblement insatures
MXPA96006467A (en)	1997-06-01	Low insaturac polioxylquylene polyethyl polyoles
MXPA96006314A (en)	1998-07-03	Method for manufacturing polyolet polyoles from bajainsaturac
CA2258617C (fr)	2006-10-31	Elastomeres de polyurethanne/uree durcis a chaud et a l'humidite dotes de proprietes physiques accrues
MXPA96006468A (en)	2000-08-01	Fabricated sealant compounds using low insaturac polioxylycylene polyethylene polyetholes