CA1310776C - Compositions d'isocyanate modifiees par de l'uree/biuret ou un melange d'uree et de biuret - Google Patents

Compositions d'isocyanate modifiees par de l'uree/biuret ou un melange d'uree et de biuret

Info

Publication number: CA1310776C
Authority: CA; Canada
Prior art keywords: composition; isocyanate; amine; functionality; modified
Prior art date: 1985-08-09
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 - Lifetime

Application number

CA000516752A

Other languages

English (en)

Inventor

Herbert R. Gillis

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.)

Zeneca Inc

Original Assignee

ICI Americas Inc

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.)

1985-08-09

Filing date

1986-08-25

Publication date

1992-11-24

1986-08-25 Application filed by ICI Americas Inc filed Critical ICI Americas Inc

1986-08-25 Priority to CA000516752A priority Critical patent/CA1310776C/fr

1992-11-24 Application granted granted Critical

1992-11-24 Publication of CA1310776C publication Critical patent/CA1310776C/fr

2009-11-24 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 127
150000002513 isocyanates Chemical class 0.000 title claims abstract description 108
239000012948 isocyanate Substances 0.000 title claims abstract description 107
239000004202 carbamide Substances 0.000 title claims abstract description 23
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title claims abstract description 22
OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 title claims abstract description 20
150000001412 amines Chemical class 0.000 claims abstract description 49
238000006243 chemical reaction Methods 0.000 claims abstract description 43
239000005056 polyisocyanate Substances 0.000 claims abstract description 36
229920001228 polyisocyanate Polymers 0.000 claims abstract description 35
239000003795 chemical substances by application Substances 0.000 claims abstract description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
239000002253 acid Substances 0.000 claims abstract description 10
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 8
ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 claims abstract description 8
230000009257 reactivity Effects 0.000 claims abstract description 8
150000007513 acids Chemical class 0.000 claims abstract description 7
239000002841 Lewis acid Substances 0.000 claims abstract description 4
239000002168 alkylating agent Substances 0.000 claims abstract description 4
229940100198 alkylating agent Drugs 0.000 claims abstract description 4
239000007795 chemical reaction product Substances 0.000 claims abstract description 4
150000007517 lewis acids Chemical class 0.000 claims abstract description 4
150000003839 salts Chemical class 0.000 claims abstract 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 claims description 14
229920000570 polyether Polymers 0.000 claims description 14
239000000463 material Substances 0.000 claims description 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
239000004721 Polyphenylene oxide Substances 0.000 claims description 9
125000003277 amino group Chemical group 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 8
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 7
239000004814 polyurethane Substances 0.000 claims description 6
229920002635 polyurethane Polymers 0.000 claims description 6
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 4
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
239000004952 Polyamide Substances 0.000 claims description 2
229920002396 Polyurea Polymers 0.000 claims description 2
229920002647 polyamide Polymers 0.000 claims description 2
229920003226 polyurethane urea Polymers 0.000 claims description 2
229920000768 polyamine Polymers 0.000 description 66
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 47
239000000047 product Substances 0.000 description 34
239000007787 solid Substances 0.000 description 29
239000000126 substance Substances 0.000 description 26
229910052757 nitrogen Inorganic materials 0.000 description 24
239000007788 liquid Substances 0.000 description 21
235000013877 carbamide Nutrition 0.000 description 19
239000002981 blocking agent Substances 0.000 description 18
-1 hydroxy, carboxy Chemical group 0.000 description 18
238000000034 method Methods 0.000 description 17
150000003141 primary amines Chemical class 0.000 description 15
102100030852 Run domain Beclin-1-interacting and cysteine-rich domain-containing protein Human genes 0.000 description 11
101710179516 Run domain Beclin-1-interacting and cysteine-rich domain-containing protein Proteins 0.000 description 11
150000004985 diamines Chemical class 0.000 description 11
229920001451 polypropylene glycol Polymers 0.000 description 11
239000012298 atmosphere Substances 0.000 description 10
239000000499 gel Substances 0.000 description 10
239000004615 ingredient Substances 0.000 description 10
239000007789 gas Substances 0.000 description 9
238000003860 storage Methods 0.000 description 9
238000013019 agitation Methods 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
230000000903 blocking effect Effects 0.000 description 7
229910002092 carbon dioxide Inorganic materials 0.000 description 7
238000002156 mixing Methods 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
238000009472 formulation Methods 0.000 description 6
150000002483 hydrogen compounds Chemical class 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
230000002152 alkylating effect Effects 0.000 description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
239000011521 glass Substances 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000003340 retarding agent Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
239000001361 adipic acid Substances 0.000 description 3
235000011037 adipic acid Nutrition 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
125000005442 diisocyanate group Chemical group 0.000 description 3
239000013020 final formulation Substances 0.000 description 3
150000002334 glycols Chemical class 0.000 description 3
150000004677 hydrates Chemical class 0.000 description 3
229920005862 polyol Polymers 0.000 description 3
150000003077 polyols Chemical class 0.000 description 3
238000010926 purge Methods 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000000758 substrate Substances 0.000 description 3
LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical class C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
230000009471 action Effects 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000012043 crude product Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
239000012467 final product Substances 0.000 description 2
239000006260 foam Substances 0.000 description 2
238000005187 foaming Methods 0.000 description 2
239000003517 fume Substances 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000012535 impurity Substances 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
125000005702 oxyalkylene group Chemical group 0.000 description 2
125000006353 oxyethylene group Chemical group 0.000 description 2
229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 2
238000000926 separation method Methods 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
230000003068 static effect Effects 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
125000003396 thiol group Chemical group [H]S* 0.000 description 2
150000003672 ureas Chemical class 0.000 description 2
DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 1
CQWYAXCOVZKLHY-UHFFFAOYSA-N 1-bromo-2,2-dimethylpropane Chemical compound CC(C)(C)CBr CQWYAXCOVZKLHY-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
239000004604 Blowing Agent Substances 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
101100281516 Caenorhabditis elegans fox-1 gene Proteins 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
239000004970 Chain extender Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
239000009261 D 400 Substances 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
YKFRUJSEPGHZFJ-UHFFFAOYSA-N N-trimethylsilylimidazole Chemical compound C[Si](C)(C)N1C=CN=C1 YKFRUJSEPGHZFJ-UHFFFAOYSA-N 0.000 description 1
IIGAAOXXRKTFAM-UHFFFAOYSA-N N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C Chemical compound N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C IIGAAOXXRKTFAM-UHFFFAOYSA-N 0.000 description 1
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
ZDVDCDLBOLSVGM-UHFFFAOYSA-N [chloro(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(Cl)C1=CC=CC=C1 ZDVDCDLBOLSVGM-UHFFFAOYSA-N 0.000 description 1
230000009102 absorption Effects 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
239000004411 aluminium Chemical class 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 1
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
239000004327 boric acid Substances 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
UCKORWKZRPKRQE-UHFFFAOYSA-N bromo(triethyl)silane Chemical compound CC[Si](Br)(CC)CC UCKORWKZRPKRQE-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
UOKRBSXOBUKDGE-UHFFFAOYSA-N butylphosphonic acid Chemical compound CCCCP(O)(O)=O UOKRBSXOBUKDGE-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000011575 calcium Chemical class 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
235000011116 calcium hydroxide Nutrition 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
ZZBNZZCHSNOXOH-UHFFFAOYSA-N chloro(trimethyl)germane Chemical compound C[Ge](C)(C)Cl ZZBNZZCHSNOXOH-UHFFFAOYSA-N 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
230000001010 compromised effect Effects 0.000 description 1
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XXKOQQBKBHUATC-UHFFFAOYSA-N cyclohexylmethylcyclohexane Chemical compound C1CCCCC1CC1CCCCC1 XXKOQQBKBHUATC-UHFFFAOYSA-N 0.000 description 1
PESYEWKSBIWTAK-UHFFFAOYSA-N cyclopenta-1,3-diene;titanium(2+) Chemical compound [Ti+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 PESYEWKSBIWTAK-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical class C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000000806 elastomer Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000003063 flame retardant Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
229960004275 glycolic acid Drugs 0.000 description 1
239000008241 heterogeneous mixture Substances 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
150000002540 isothiocyanates Chemical class 0.000 description 1
239000012263 liquid product Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
235000011285 magnesium acetate Nutrition 0.000 description 1
239000011654 magnesium acetate Substances 0.000 description 1
229940069446 magnesium acetate Drugs 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [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
BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 1
238000006263 metalation reaction Methods 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
150000003009 phosphonic acids Chemical class 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920005906 polyester polyol Polymers 0.000 description 1
229920006149 polyester-amide block copolymer Polymers 0.000 description 1
229920006324 polyoxymethylene Polymers 0.000 description 1
229920006389 polyphenyl polymer Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000008569 process Effects 0.000 description 1
239000001819 propan-2-yl (E)-3-phenylprop-2-enoate Substances 0.000 description 1
RGACABDFLVLVCT-UHFFFAOYSA-N propan-2-yl 3-phenylprop-2-enoate Chemical compound CC(C)OC(=O)C=CC1=CC=CC=C1 RGACABDFLVLVCT-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000010107 reaction injection moulding Methods 0.000 description 1
230000000979 retarding effect Effects 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000000243 solution Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
150000003606 tin compounds Chemical class 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
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
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
229940029284 trichlorofluoromethane Drugs 0.000 description 1
AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
238000009849 vacuum degassing Methods 0.000 description 1
238000009489 vacuum treatment Methods 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Landscapes

Polyurethanes Or Polyureas (AREA)

CA000516752A 1985-08-09 1986-08-25 Compositions d'isocyanate modifiees par de l'uree/biuret ou un melange d'uree et de biuret Expired - Lifetime CA1310776C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000516752A CA1310776C (fr)	1985-08-09	1986-08-25	Compositions d'isocyanate modifiees par de l'uree/biuret ou un melange d'uree et de biuret

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US76443585A	1985-08-09	1985-08-09
CA000516752A CA1310776C (fr)	1985-08-09	1986-08-25	Compositions d'isocyanate modifiees par de l'uree/biuret ou un melange d'uree et de biuret

Publications (1)

Publication Number	Publication Date
CA1310776C true CA1310776C (fr)	1992-11-24

Family

ID=25671079

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000516752A Expired - Lifetime CA1310776C (fr)	1985-08-09	1986-08-25	Compositions d'isocyanate modifiees par de l'uree/biuret ou un melange d'uree et de biuret

Country Status (1)

Country	Link
CA (1)	CA1310776C (fr)

1986
- 1986-08-25 CA CA000516752A patent/CA1310776C/fr not_active Expired - Lifetime

Legal Events

Date	Code	Title	Description
1995-05-24	MKLA	Lapsed

Publication	Publication Date	Title
CN1042231C (zh)	1999-02-24	聚氨酯泡沫塑料
CA1271775A (fr)	1990-07-17	Derives d'isocyanate renfermant des groupes carbodiimides; methode de preparation et utilisation comme additifs pour les solutions ou les dispersions aqueuses de matieres plastiques
KR100216934B1 (ko)	1999-09-01	카보디이미드 및/ 또는 우레톤 이민 그룹을 함유하는 액체 저장성 유기이소시아네이트의 제조방법 및 폴리우레탄 플라스틱을 제조하기 위한 이의 용도
US4332742A (en)	1982-06-01	Low temperature storage stable liquid diphenylmethane diisocyanates
CA1266055A (fr)	1990-02-20	Prepartion de polyols polyethers-esters a faible teneur en oxyde d'ethylene et a forte teneur en groupes hydroxy primaires
ES2327583T3 (es)	2009-10-30	Composicion preparada a partir de un diisocianato y una monoamina y procedimiento para su preparacion.
CA1212793A (fr)	1986-10-14	Dispersion de polyurees dans les isocyanates organiques
CZ130895A3 (en)	1996-02-14	Polymer modified polyol dispersions and process for preparing thereof
US4761465A (en)	1988-08-02	Difunctional isocyanate-terminated polyoxyalkylene diamine prepolymers and polymer coatings applications
US3954825A (en)	1976-05-04	Biuret polyisocyanates
JPS58145711A (ja)	1983-08-30	重合体を含む芳香族ポリエーテルポリアミンの製造方法
JPS6040112A (ja)	1985-03-02	ポリイソシアネート組成物
GB2264499A (en)	1993-09-01	Polyurea-based dispersions, foams prepared therefrom and a process for the preparation thereof
EP0211630B1 (fr)	1991-07-24	Compositions liquides de polyisocyanate organique contenant des structures d'urée et/ou de biuret
CA1310776C (fr)	1992-11-24	Compositions d'isocyanate modifiees par de l'uree/biuret ou un melange d'uree et de biuret
US4816600A (en)	1989-03-28	Isocyanate compositions obtained from reaction of isocyanates with blocked polamines
CA2059044C (fr)	2003-06-17	Utilisation de n-(aminoalkyl)pyrrolidines comme catalyseurs pour la polyaddition de polyisocyanates
US12129330B2 (en)	2024-10-29	Method for reduction of aldehyde emission in polyurethane comprising materials
CN101903431A (zh)	2010-12-01	多异氰酸酯和聚醚单胺的新型组合物
GB2102825A (en)	1983-02-09	Polymer-modified polyols
US4766239A (en)	1988-08-23	Process for the in situ production of urea group-containing isocyanates in polyols, dispersions or solutions resulting therefrom and use thereof
USRE38415E1 (en)	2004-02-03	Use of N-(aminoalkyl) pyrrolidines as catalysts for the polyisocyanate polyaddition process
US5010160A (en)	1991-04-23	Process for preparing novel diamines
EP0263622B1 (fr)	1992-09-16	Isocyanates modifiés par l'urée
BR122022004369B1 (pt)	2024-01-02	Composição de polímero sililado