CA1205249A - Systemes monocomposant de polyurethane, stable en stockage et durcissant en milieu humide - Google Patents

Systemes monocomposant de polyurethane, stable en stockage et durcissant en milieu humide

Info

Publication number: CA1205249A
Authority: CA; Canada
Prior art keywords: product; carbon atoms; radical; acid; aliphatic
Prior art date: 1983-02-24
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000439375A

Other languages

English (en)

Inventor

Uwe Bueltjer

Heinrich Horacek

Wolfgang Druschke

Gernot Franzmann

Erhard Klahr

Hans-Juergen Foerster

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 SE

Original Assignee

BASF SE

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.)

1983-02-24

Filing date

1983-10-20

Publication date

1986-05-27

1983-10-20 Application filed by BASF SE filed Critical BASF SE

1986-05-27 Application granted granted Critical

1986-05-27 Publication of CA1205249A publication Critical patent/CA1205249A/fr

Status Expired legal-status Critical Current

Links

239000004814 polyurethane Substances 0.000 title claims abstract description 19
229920002635 polyurethane Polymers 0.000 title claims abstract description 17
238000013008 moisture curing Methods 0.000 title claims abstract description 15
239000000203 mixture Substances 0.000 claims abstract description 23
-1 aromatic carboxylic acids Chemical class 0.000 claims abstract description 22
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
229920001730 Moisture cure polyurethane Polymers 0.000 claims abstract description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 12
239000012948 isocyanate Substances 0.000 claims abstract description 8
239000003377 acid catalyst Substances 0.000 claims abstract description 6
150000002513 isocyanates Chemical class 0.000 claims abstract description 6
150000007933 aliphatic carboxylic acids Chemical class 0.000 claims abstract description 5
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims abstract description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
239000001301 oxygen Substances 0.000 claims abstract description 4
229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
239000000047 product Substances 0.000 claims description 19
229920005862 polyol Polymers 0.000 claims description 12
150000003077 polyols Chemical class 0.000 claims description 12
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 11
239000005056 polyisocyanate Substances 0.000 claims description 10
229920001228 polyisocyanate Polymers 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 6
125000001931 aliphatic group Chemical group 0.000 claims description 6
239000005711 Benzoic acid Substances 0.000 claims description 5
235000010233 benzoic acid Nutrition 0.000 claims description 5
239000004970 Chain extender Substances 0.000 claims description 4
150000004705 aldimines Chemical group 0.000 claims description 4
239000000945 filler Substances 0.000 claims description 4
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 4
ZVFDTKUVRCTHQE-UHFFFAOYSA-N Diisodecyl phthalate Chemical group CC(C)CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC(C)C ZVFDTKUVRCTHQE-UHFFFAOYSA-N 0.000 claims description 3
239000007795 chemical reaction product Substances 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
239000000463 material Substances 0.000 abstract description 5
238000000576 coating method Methods 0.000 abstract description 3
239000011248 coating agent Substances 0.000 abstract description 2
238000005266 casting Methods 0.000 abstract 1
238000007789 sealing Methods 0.000 abstract 1
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 8
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
150000001875 compounds Chemical class 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
125000005442 diisocyanate group Chemical group 0.000 description 5
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 5
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
239000004721 Polyphenylene oxide Substances 0.000 description 4
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
235000011187 glycerol Nutrition 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
229920000570 polyether Polymers 0.000 description 4
YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-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
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
150000004984 aromatic diamines Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000001723 curing Methods 0.000 description 3
150000004985 diamines Chemical class 0.000 description 3
238000004821 distillation Methods 0.000 description 3
NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
238000000034 method Methods 0.000 description 3
229920005906 polyester polyol Polymers 0.000 description 3
229920006324 polyoxymethylene Polymers 0.000 description 3
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
229940113165 trimethylolpropane Drugs 0.000 description 3
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
239000005058 Isophorone diisocyanate Substances 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
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000001361 adipic acid Substances 0.000 description 2
235000011037 adipic acid Nutrition 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
150000001414 amino alcohols Chemical class 0.000 description 2
CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
150000004292 cyclic ethers Chemical class 0.000 description 2
150000001991 dicarboxylic acids Chemical class 0.000 description 2
150000002009 diols Chemical class 0.000 description 2
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
239000003999 initiator Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
229920000515 polycarbonate Polymers 0.000 description 2
239000004417 polycarbonate Substances 0.000 description 2
229920006149 polyester-amide block copolymer Polymers 0.000 description 2
229920000166 polytrimethylene carbonate Polymers 0.000 description 2
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
238000000926 separation method Methods 0.000 description 2
TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
150000003457 sulfones Chemical class 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
LWBHHRRTOZQPDM-UHFFFAOYSA-N undecanedioic acid Chemical compound OC(=O)CCCCCCCCCC(O)=O LWBHHRRTOZQPDM-UHFFFAOYSA-N 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
FQERLIOIVXPZKH-UHFFFAOYSA-N 1,2,4-trioxane Chemical compound C1COOCO1 FQERLIOIVXPZKH-UHFFFAOYSA-N 0.000 description 1
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-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
QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 1
ALLSOOQIDPLIER-UHFFFAOYSA-N 2,3,4-trichlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C(Cl)=C1Cl ALLSOOQIDPLIER-UHFFFAOYSA-N 0.000 description 1
PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
GXVUZYLYWKWJIM-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanamine Chemical compound NCCOCCN GXVUZYLYWKWJIM-UHFFFAOYSA-N 0.000 description 1
HOLGXWDGCVTMTB-UHFFFAOYSA-N 2-(2-aminophenyl)aniline Chemical group NC1=CC=CC=C1C1=CC=CC=C1N HOLGXWDGCVTMTB-UHFFFAOYSA-N 0.000 description 1
OHKOAJUTRVTYSW-UHFFFAOYSA-N 2-[(2-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC=C1CC1=CC=CC=C1N OHKOAJUTRVTYSW-UHFFFAOYSA-N 0.000 description 1
IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
POTQBGGWSWSMCX-UHFFFAOYSA-N 3-[2-(3-aminopropoxy)ethoxy]propan-1-amine Chemical compound NCCCOCCOCCCN POTQBGGWSWSMCX-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
CSIVUWBDBJMXDY-UHFFFAOYSA-N 4-(4-aminocyclohexyl)cyclohexan-1-amine Chemical group C1CC(N)CCC1C1CCC(N)CC1 CSIVUWBDBJMXDY-UHFFFAOYSA-N 0.000 description 1
DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
125000003172 aldehyde group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 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
239000004202 carbamide Substances 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
239000003431 cross linking reagent Substances 0.000 description 1
VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 1
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
150000004658 ketimines Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
NVSOSQNIJKZFBR-UHFFFAOYSA-N n'-[2-(ethylamino)ethyl]ethane-1,2-diamine Chemical compound CCNCCNCCN NVSOSQNIJKZFBR-UHFFFAOYSA-N 0.000 description 1
HYWYRSMBCFDLJT-UHFFFAOYSA-N nimesulide Chemical compound CS(=O)(=O)NC1=CC=C([N+]([O-])=O)C=C1OC1=CC=CC=C1 HYWYRSMBCFDLJT-UHFFFAOYSA-N 0.000 description 1
229960000965 nimesulide Drugs 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
150000003022 phthalic acids Chemical class 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000004848 polyfunctional curative Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920005903 polyol mixture Polymers 0.000 description 1
230000005855 radiation Effects 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
150000003504 terephthalic acids Chemical class 0.000 description 1
UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000009974 thixotropic effect Effects 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
229960004319 trichloroacetic acid Drugs 0.000 description 1
150000004072 triols Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2190/00—Compositions for sealing or packing joints

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Polyurethanes Or Polyureas (AREA)

CA000439375A 1983-02-24 1983-10-20 Systemes monocomposant de polyurethane, stable en stockage et durcissant en milieu humide Expired CA1205249A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19833306373 DE3306373A1 (de)	1983-02-24	1983-02-24	Feuchtigkeitshaertendes, lagerstabiles einkomponenten-polyurethansystem
DEP3306373.7		1983-02-24

Publications (1)

Publication Number	Publication Date
CA1205249A true CA1205249A (fr)	1986-05-27

Family

ID=6191659

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000439375A Expired CA1205249A (fr)	1983-02-24	1983-10-20	Systemes monocomposant de polyurethane, stable en stockage et durcissant en milieu humide

Country Status (2)

Country	Link
CA (1)	CA1205249A (fr)
DE (1)	DE3306373A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4720535A (en) *	1986-03-11	1988-01-19	Basf Aktiengesellschaft	Moisture tempered, storage stable single component polyurethane systems and their application
US8816037B2 (en)	2007-03-27	2014-08-26	Sika Technology Ag	Asymmetric dialdimine-containing polyurethane composition

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3624924A1 (de) *	1986-07-23	1988-01-28	Basf Ag	Feuchtigkeitshaertende, lagerstabile einkomponenten-polyurethansysteme und deren verwendung
DE3716479A1 (de) *	1987-05-16	1988-11-24	Elastogran Gmbh	Verfahren zur herstellung von ueberzuegen aus polyurethan-einkomponenten-systemen und wasserdampf
EP0375318A3 (fr) *	1988-12-21	1991-01-23	MITSUI TOATSU CHEMICALS, Inc.	Dérivés de polyaldimines
DE4311923A1 (de) *	1993-04-10	1994-10-13	Huels Chemische Werke Ag	Zweikomponentig zu verarbeitende Beschichtungszusammensetzung zur Herstellung von PUR-Elastomeren
US5444117A (en) *	1994-02-09	1995-08-22	Bayer Corporation	Coating compositions containing polyisocyanates and aldimines which have improved storage stability
EP1384709A1 (fr) *	2002-07-26	2004-01-28	Sika Technology AG	Polyaldimines
EP1384735A1 (fr) *	2002-07-26	2004-01-28	Sika Technology AG	Composition de polyuréthane contenant un polyaldimine
EP4229032B1 (fr) *	2020-10-19	2025-11-05	Sika Technology AG	Mélange d'aldimine cycloaliphatique
US20230323009A1 (en) *	2020-10-19	2023-10-12	Sika Technology Ag	Moisture-curing polyurethane composition

1983
- 1983-02-24 DE DE19833306373 patent/DE3306373A1/de not_active Withdrawn
- 1983-10-20 CA CA000439375A patent/CA1205249A/fr not_active Expired

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4720535A (en) *	1986-03-11	1988-01-19	Basf Aktiengesellschaft	Moisture tempered, storage stable single component polyurethane systems and their application
US8816037B2 (en)	2007-03-27	2014-08-26	Sika Technology Ag	Asymmetric dialdimine-containing polyurethane composition
US9290608B2 (en)	2007-03-27	2016-03-22	Sika Technology Ag	Asymmetric dialdimine-containing polyurethane composition

Also Published As

Publication number	Publication date
DE3306373A1 (de)	1984-08-30

Legal Events

Date	Code	Title	Description
2003-10-20	MKEX	Expiry

Publication	Publication Date	Title
US4469831A (en)	1984-09-04	Moisture-curing, storage stable, single-component polyurethane systems
KR840000523B1 (ko)	1984-04-17	합성 중합체의 제조방법
CA1205249A (fr)	1986-05-27	Systemes monocomposant de polyurethane, stable en stockage et durcissant en milieu humide
CA1332020C (fr)	1994-09-13	Systemes de polyurethane a composante unique, se conservant bien et traites a l'humidite, et leur application
KR100461621B1 (ko)	2005-10-21	폴리우레탄수지
US4365051A (en)	1982-12-21	Polyurethane prepared from diamine and prepolymer
KR20080055978A (ko)	2008-06-19	이소시아네이트 단량체 함량이 낮은 반응성 폴리우레탄-열용융 접착제
KR19980024882A (ko)	1998-07-06	성능이 개선된 경화성 실란 엔드 캡핑된(endcapped) 조성물
SK9462002A3 (en)	2002-11-06	Adhesion promoters for monomer-free reactive polyurethanes
JP2026048905A (ja)	2026-03-17	低遊離ポリウレタンプレポリマー組成物
CA2493600A1 (fr)	2004-02-12	Compositions de polyurethanne contenant une polyaldimine
CA2628322A1 (fr)	2007-04-05	Aldimines comprenant des groupes reactifs qui presentent de l'hydrogene actif et utilisation de celles-ci
US4254272A (en)	1981-03-03	Aromatic diamines and polyurethanes cured thereby
US4222955A (en)	1980-09-16	3,5-Diamino-4-tert.-alkylbenzonitriles
JPH04283214A (ja)	1992-10-08	ポリエーテルウレタン尿素アミン類の製造方法およびその用途
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DE3133769A1 (de)	1983-03-10	Feuchtigkeitshaertendes, lagerstabiles einkomponenten-polyurethansystem
KR930006250B1 (ko)	1993-07-09	반응성 조성물
US9238617B2 (en)	2016-01-19	Polyureas made from aminocrotonates
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JP2744322B2 (ja)	1998-04-28	ポリイソシアナートの製造方法