CA2061592A1 - Dispersions stables de polyhydrazodicarbonamides utiles pour la preparation de produits de polyurethane a capacite amelioree de resistance a une charge - Google Patents

Dispersions stables de polyhydrazodicarbonamides utiles pour la preparation de produits de polyurethane a capacite amelioree de resistance a une charge

Info

Publication number: CA2061592A1
Authority: CA; Canada
Prior art keywords: parts; isocyanate; weight; groups; dispersion
Prior art date: 1991-03-06
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 2061592

Other languages

English (en)

Inventor

Robert P. Yeater

Robin E. Tirpak

Mark A. Koshute

David A. Radovich

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.)

Bayer Corp

Original Assignee

Individual

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.)

1991-03-06

Filing date

1992-02-20

Publication date

1992-09-07

1992-02-20 Application filed by Individual filed Critical Individual

1992-09-07 Publication of CA2061592A1 publication Critical patent/CA2061592A1/fr

Status Abandoned legal-status Critical Current

Links

239000006185 dispersion Substances 0.000 title claims abstract description 63
238000002360 preparation method Methods 0.000 title claims abstract description 14
239000004814 polyurethane Substances 0.000 title abstract description 9
229920002635 polyurethane Polymers 0.000 title abstract description 9
239000000203 mixture Substances 0.000 claims abstract description 34
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 33
150000001875 compounds Chemical class 0.000 claims abstract description 31
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 30
238000000034 method Methods 0.000 claims abstract description 26
238000006243 chemical reaction Methods 0.000 claims abstract description 24
239000012948 isocyanate Substances 0.000 claims abstract description 14
150000002513 isocyanates Chemical class 0.000 claims abstract description 14
229920005830 Polyurethane Foam Polymers 0.000 claims abstract description 7
239000011496 polyurethane foam Substances 0.000 claims abstract description 7
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
150000003606 tin compounds Chemical class 0.000 claims abstract description 5
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical group OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 7
239000000463 material Substances 0.000 claims description 7
125000001931 aliphatic group Chemical group 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 3
239000004604 Blowing Agent Substances 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
229910052739 hydrogen Inorganic materials 0.000 claims 2
239000001257 hydrogen Substances 0.000 claims 2
238000004519 manufacturing process Methods 0.000 abstract description 6
229920000570 polyether Polymers 0.000 description 32
150000003077 polyols Chemical class 0.000 description 22
239000004721 Polyphenylene oxide Substances 0.000 description 21
239000006260 foam Substances 0.000 description 21
229920001228 polyisocyanate Polymers 0.000 description 21
239000005056 polyisocyanate Substances 0.000 description 21
229920005862 polyol Polymers 0.000 description 21
-1 polyesterethers Polymers 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
239000000047 product Substances 0.000 description 16
230000003068 static effect Effects 0.000 description 16
229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 14
150000002429 hydrazines Chemical class 0.000 description 14
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
229920000728 polyester Polymers 0.000 description 10
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 9
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 8
230000000052 comparative effect Effects 0.000 description 8
150000002009 diols Chemical class 0.000 description 8
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 8
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 7
239000003054 catalyst Substances 0.000 description 7
229940043237 diethanolamine Drugs 0.000 description 7
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 7
238000002156 mixing Methods 0.000 description 7
239000007787 solid Substances 0.000 description 7
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000012975 dibutyltin dilaurate Substances 0.000 description 5
238000005187 foaming Methods 0.000 description 5
150000002334 glycols Chemical class 0.000 description 5
229910001887 tin oxide Inorganic materials 0.000 description 5
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
150000001735 carboxylic acids Chemical class 0.000 description 4
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
238000006116 polymerization reaction Methods 0.000 description 4
229920006295 polythiol Polymers 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical class [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
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 3
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 3
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000001361 adipic acid Substances 0.000 description 3
235000011037 adipic acid Nutrition 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000002245 particle Substances 0.000 description 3
229920000768 polyamine Polymers 0.000 description 3
229920000515 polycarbonate Polymers 0.000 description 3
239000004417 polycarbonate Substances 0.000 description 3
229920001296 polysiloxane Polymers 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
150000005846 sugar alcohols Polymers 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
239000012974 tin catalyst Substances 0.000 description 3
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-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
239000004952 Polyamide Substances 0.000 description 2
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-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
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
150000001414 amino alcohols Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
230000008901 benefit Effects 0.000 description 2
PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
150000004985 diamines Chemical class 0.000 description 2
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
239000001530 fumaric acid Substances 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 2
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
150000002596 lactones Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
150000002924 oxiranes Chemical class 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 2
230000000704 physical effect Effects 0.000 description 2
229920000233 poly(alkylene oxides) Polymers 0.000 description 2
229920002647 polyamide Polymers 0.000 description 2
229920002857 polybutadiene Polymers 0.000 description 2
229920006149 polyester-amide block copolymer Polymers 0.000 description 2
229920006324 polyoxymethylene Polymers 0.000 description 2
229920000166 polytrimethylene carbonate Polymers 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
150000003384 small molecules Chemical class 0.000 description 2
239000000243 solution Substances 0.000 description 2
230000000087 stabilizing effect Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
239000012970 tertiary amine catalyst Substances 0.000 description 2
YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 2
229950006389 thiodiglycol Drugs 0.000 description 2
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical class Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical group NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
NIDNOXCRFUCAKQ-UMRXKNAASA-N (1s,2r,3s,4r)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical compound C1[C@H]2C=C[C@@H]1[C@H](C(=O)O)[C@@H]2C(O)=O NIDNOXCRFUCAKQ-UMRXKNAASA-N 0.000 description 1
SCZGZDLUGUYLRV-UHFFFAOYSA-N (2-methylphenyl)hydrazine Chemical compound CC1=CC=CC=C1NN SCZGZDLUGUYLRV-UHFFFAOYSA-N 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 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
KMOUUZVZFBCRAM-UHFFFAOYSA-N 1,2,3,6-tetrahydrophthalic anhydride Chemical compound C1C=CCC2C(=O)OC(=O)C21 KMOUUZVZFBCRAM-UHFFFAOYSA-N 0.000 description 1
FQERLIOIVXPZKH-UHFFFAOYSA-N 1,2,4-trioxane Chemical compound C1COOCO1 FQERLIOIVXPZKH-UHFFFAOYSA-N 0.000 description 1
ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
YCBOYOYVDOUXLH-UHFFFAOYSA-N 1,2-Diethylhydrazine Chemical compound CCNNCC YCBOYOYVDOUXLH-UHFFFAOYSA-N 0.000 description 1
DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 1
GHXZZOARPRFXEH-UHFFFAOYSA-N 1,2-bis(2-methylpropyl)hydrazine Chemical compound CC(C)CNNCC(C)C GHXZZOARPRFXEH-UHFFFAOYSA-N 0.000 description 1
ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
LHYKTQVFLKHQSR-UHFFFAOYSA-N 1-amino-3-methylurea Chemical compound CNC(=O)NN LHYKTQVFLKHQSR-UHFFFAOYSA-N 0.000 description 1
HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
ZEMCGIDMAMIJLF-UHFFFAOYSA-N 1-benzyl-2-phenylhydrazine Chemical compound C=1C=CC=CC=1CNNC1=CC=CC=C1 ZEMCGIDMAMIJLF-UHFFFAOYSA-N 0.000 description 1
OZWDURQLHZCMQG-UHFFFAOYSA-N 1-butyl-2-methylhydrazine Chemical compound CCCCNNC OZWDURQLHZCMQG-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
LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 1
NGSOWKPBNFOQCR-UHFFFAOYSA-N 2-methylpropylhydrazine Chemical compound CC(C)CNN NGSOWKPBNFOQCR-UHFFFAOYSA-N 0.000 description 1
CEZWFBJCEWZGHX-UHFFFAOYSA-N 4-isocyanato-n-(oxomethylidene)benzenesulfonamide Chemical class O=C=NC1=CC=C(S(=O)(=O)N=C=O)C=C1 CEZWFBJCEWZGHX-UHFFFAOYSA-N 0.000 description 1
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
OEGFAAFCIWSUGO-UHFFFAOYSA-L CC([O-])=O.CC([O-])=O.CCC[Sn++]CCC Chemical compound CC([O-])=O.CC([O-])=O.CCC[Sn++]CCC OEGFAAFCIWSUGO-UHFFFAOYSA-L 0.000 description 1
RDRSAQPTVVNVEN-UHFFFAOYSA-L CCC([O-])=O.CCC([O-])=O.CCCCC[Sn++]CCCCC Chemical compound CCC([O-])=O.CCC([O-])=O.CCCCC[Sn++]CCCCC RDRSAQPTVVNVEN-UHFFFAOYSA-L 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004970 Chain extender Substances 0.000 description 1
241000518994 Conta Species 0.000 description 1
239000004971 Cross linker Substances 0.000 description 1
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 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
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125000005397 methacrylic acid ester group Chemical group 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
238000000465 moulding Methods 0.000 description 1
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
150000002829 nitrogen Chemical class 0.000 description 1
CYCFYXLDTSNTGP-UHFFFAOYSA-L octadecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CYCFYXLDTSNTGP-UHFFFAOYSA-L 0.000 description 1
OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
229940049964 oleate Drugs 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
JHRUIJPOAATFRO-UHFFFAOYSA-N oxo(dipropyl)tin Chemical compound CCC[Sn](=O)CCC JHRUIJPOAATFRO-UHFFFAOYSA-N 0.000 description 1
238000012856 packing Methods 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
229960000964 phenelzine Drugs 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
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IYPZRUYMFDWKSS-UHFFFAOYSA-N piperazin-1-amine Chemical compound NN1CCNCC1 IYPZRUYMFDWKSS-UHFFFAOYSA-N 0.000 description 1
PVCOXMQIAVGPJN-UHFFFAOYSA-N piperazine-1,4-diamine Chemical compound NN1CCN(N)CC1 PVCOXMQIAVGPJN-UHFFFAOYSA-N 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
229920001748 polybutylene Polymers 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
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150000003141 primary amines Chemical class 0.000 description 1
KJAQRHMKLVGSCG-UHFFFAOYSA-N propan-2-ylhydrazine Chemical compound CC(C)NN KJAQRHMKLVGSCG-UHFFFAOYSA-N 0.000 description 1
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UKPBXIFLSVLDPA-UHFFFAOYSA-N propylhydrazine Chemical compound CCCNN UKPBXIFLSVLDPA-UHFFFAOYSA-N 0.000 description 1
238000005086 pumping Methods 0.000 description 1
239000011369 resultant mixture Substances 0.000 description 1
150000003335 secondary amines Chemical group 0.000 description 1
DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
150000003349 semicarbazides Chemical class 0.000 description 1
229920002545 silicone oil Polymers 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
MUQNAPSBHXFMHT-UHFFFAOYSA-N tert-butylhydrazine Chemical compound CC(C)(C)NN MUQNAPSBHXFMHT-UHFFFAOYSA-N 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
125000003396 thiol group Chemical group [H]S* 0.000 description 1
KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
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 1
150000004998 toluenediamines Chemical class 0.000 description 1
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
XMHKTINRBAKEDS-UHFFFAOYSA-N trioctyltin Chemical compound CCCCCCCC[Sn](CCCCCCCC)CCCCCCCC XMHKTINRBAKEDS-UHFFFAOYSA-N 0.000 description 1
ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical class OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1

Landscapes

Polyurethanes Or Polyureas (AREA)

CA 2061592 1991-03-06 1992-02-20 Dispersions stables de polyhydrazodicarbonamides utiles pour la preparation de produits de polyurethane a capacite amelioree de resistance a une charge Abandoned CA2061592A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US66539291A	1991-03-06	1991-03-06
US07/665,392		1991-03-06

Publications (1)

Publication Number	Publication Date
CA2061592A1 true CA2061592A1 (fr)	1992-09-07

Family

ID=24669934

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2061592 Abandoned CA2061592A1 (fr)	1991-03-06	1992-02-20	Dispersions stables de polyhydrazodicarbonamides utiles pour la preparation de produits de polyurethane a capacite amelioree de resistance a une charge

Country Status (1)

Country	Link
CA (1)	CA2061592A1 (fr)

1992
- 1992-02-20 CA CA 2061592 patent/CA2061592A1/fr not_active Abandoned

Legal Events

Date	Code	Title	Description
1995-08-20	FZDE	Dead

Publication	Publication Date	Title
JP3106150B2 (ja)	2000-11-06	軟質高分子発泡体の製法
US4042537A (en)	1977-08-16	Process for the production of polyurethane foams
KR100285787B1 (ko)	2001-05-02	미공질 엘라스토머 제조용 반응 물질계
CA1242848A (fr)	1988-10-04	Mousses souples de polyurethane
KR20010022766A (ko)	2001-03-26	굴곡 피로가 개선된 신규한 폴리우레탄 발포체 조성물
JP4907812B2 (ja)	2012-04-04	Ｐｉｐａポリオールの製造方法
US5143942A (en)	1992-09-01	Polyurethanes
US4452924A (en)	1984-06-05	Flexible polyurethane foams having improved load bearing characteristics
EP1511794A2 (fr)	2005-03-09	Polymeres supramoleculaires expanses
US20030236315A1 (en)	2003-12-25	Foamed isocyanate-based polymer having improved hardness properties and process for production thereof
US5342855A (en)	1994-08-30	Stable dispersions of polyhydrazodicarbonamides useful in the preparation of polyurethane products having improved load-bearing capacity
CA1334310C (fr)	1995-02-07	Procede d'obtention de dispersions stables, les dispersions obtenues et leur application a la fabrication industrielle de polyurethanes
JPS63150347A (ja)	1988-06-23	相溶化されたα，ω―アルキレングリコールとポリエーテルポリオールとのブレンドおよびその製法
JPH07165862A (ja)	1995-06-27	軟質ポリウレタンフォームの製造方法
CA1340034C (fr)	1998-09-08	Dispersions stables et methode de preparation
EP0187333B1 (fr)	1993-02-10	Procédé pour la préparation de dispersions de polyurées et/ou polyhydrazodicarbonamides et préparation de polyuréthanes à partir des dites dispersions.
US5332763A (en)	1994-07-26	Stable dispersions and their use in the preparation of polyurethane foams
EP0350644A1 (fr)	1990-01-17	Systèmes de polyurées pour le procédé de moulage réactif par injection ayant des propriétés d'écoulement modifiées
JP4932727B2 (ja)	2012-05-16	Ｐｉｐａポリオールの製造方法
CA2061592A1 (fr)	1992-09-07	Dispersions stables de polyhydrazodicarbonamides utiles pour la preparation de produits de polyurethane a capacite amelioree de resistance a une charge
JPH01110520A (ja)	1989-04-27	耐熱性ポリウレタン尿素エラストマーの製造方法
JPH07196758A (ja)	1995-08-01	強化ポリウレタン用フィラー含有ポリオールおよび該ポリオールを用いた強化ポリウレタンの製造方法