CA1293085C - Elastomeres renfermant des groupes polyamide et polyuree lies; methode de preparation d'articles moules, elastiques et non cellulaires, a partir de ces elastomeres - Google Patents

Elastomeres renfermant des groupes polyamide et polyuree lies; methode de preparation d'articles moules, elastiques et non cellulaires, a partir de ces elastomeres

Info

Publication number: CA1293085C
Authority: CA; Canada
Prior art keywords: groups; molecular weight; din; percent; group
Prior art date: 1988-03-21
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

CA000562006A

Other languages

English (en)

Inventor

Guenter Matzke

Peter Horn

Hans Ulrich Schmidt

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.)

1988-03-21

Filing date

1988-03-21

Publication date

1991-12-10

1988-03-21 Application filed by BASF SE filed Critical BASF SE

1988-03-21 Priority to CA000562006A priority Critical patent/CA1293085C/fr

1991-12-10 Application granted granted Critical

1991-12-10 Publication of CA1293085C publication Critical patent/CA1293085C/fr

2008-12-10 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 50
239000000806 elastomer Substances 0.000 title claims abstract description 45
229920001971 elastomer Polymers 0.000 title claims abstract description 44
238000002360 preparation method Methods 0.000 title claims abstract description 28
229920002396 Polyurea Polymers 0.000 title claims abstract description 27
229920002647 polyamide Polymers 0.000 title claims abstract description 23
239000004952 Polyamide Substances 0.000 title claims abstract description 22
230000001413 cellular effect Effects 0.000 title abstract description 21
239000000203 mixture Substances 0.000 claims abstract description 83
239000005056 polyisocyanate Substances 0.000 claims abstract description 37
229920001228 polyisocyanate Polymers 0.000 claims abstract description 32
229920000343 polyazomethine Polymers 0.000 claims abstract description 25
239000003054 catalyst Substances 0.000 claims abstract description 22
238000006243 chemical reaction Methods 0.000 claims abstract description 21
150000002576 ketones Chemical class 0.000 claims abstract description 17
229920000768 polyamine Polymers 0.000 claims abstract description 15
125000003118 aryl group Chemical class 0.000 claims abstract description 14
150000001299 aldehydes Chemical class 0.000 claims abstract description 11
239000007795 chemical reaction product Substances 0.000 claims abstract description 5
-1 alkyl radical Chemical class 0.000 claims description 45
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
125000003277 amino group Chemical group 0.000 claims description 23
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 22
125000004432 carbon atom Chemical group C* 0.000 claims description 20
150000004658 ketimines Chemical group 0.000 claims description 19
125000001931 aliphatic group Chemical group 0.000 claims description 18
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 16
150000004984 aromatic diamines Chemical class 0.000 claims description 13
229920005862 polyol Polymers 0.000 claims description 12
238000005516 engineering process Methods 0.000 claims description 10
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 9
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 6
150000001718 carbodiimides Chemical class 0.000 claims description 6
JGYUBHGXADMAQU-UHFFFAOYSA-N 2,4,6-triethylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(CC)=C1N JGYUBHGXADMAQU-UHFFFAOYSA-N 0.000 claims description 5
PISLZQACAJMAIO-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine Chemical compound CCC1=CC(C)=C(N)C(CC)=C1N PISLZQACAJMAIO-UHFFFAOYSA-N 0.000 claims description 5
VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 claims description 5
239000004604 Blowing Agent Substances 0.000 claims description 5
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 4
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 4
229940043265 methyl isobutyl ketone Drugs 0.000 claims description 4
238000007906 compression Methods 0.000 claims description 3
230000006835 compression Effects 0.000 claims description 3
RQEOBXYYEPMCPJ-UHFFFAOYSA-N 4,6-diethyl-2-methylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(C)=C1N RQEOBXYYEPMCPJ-UHFFFAOYSA-N 0.000 claims 4
239000000306 component Substances 0.000 description 50
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
238000009472 formulation Methods 0.000 description 12
150000001875 compounds Chemical class 0.000 description 10
238000002156 mixing Methods 0.000 description 10
HGXVKAPCSIXGAK-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine;4,6-diethyl-2-methylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(C)=C1N.CCC1=CC(C)=C(N)C(CC)=C1N HGXVKAPCSIXGAK-UHFFFAOYSA-N 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
239000007788 liquid Substances 0.000 description 9
150000003077 polyols Chemical class 0.000 description 9
230000000704 physical effect Effects 0.000 description 8
238000001816 cooling Methods 0.000 description 7
230000000875 corresponding effect Effects 0.000 description 7
238000002329 infrared spectrum Methods 0.000 description 7
238000010992 reflux Methods 0.000 description 7
150000003839 salts Chemical class 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
229910052751 metal Chemical class 0.000 description 6
239000002184 metal Chemical class 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
230000009257 reactivity Effects 0.000 description 6
230000002829 reductive effect Effects 0.000 description 6
239000002904 solvent Substances 0.000 description 6
HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
229920002635 polyurethane Polymers 0.000 description 5
239000004814 polyurethane Substances 0.000 description 5
238000012545 processing Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
239000011256 inorganic filler Substances 0.000 description 4
239000012948 isocyanate Substances 0.000 description 4
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
150000002513 isocyanates Chemical class 0.000 description 4
239000000463 material Substances 0.000 description 4
239000012766 organic filler Substances 0.000 description 4
229920003023 plastic Polymers 0.000 description 4
239000004033 plastic Substances 0.000 description 4
238000010107 reaction injection moulding Methods 0.000 description 4
239000012744 reinforcing agent Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
238000012644 addition polymerization Methods 0.000 description 3
125000002947 alkylene group Chemical group 0.000 description 3
150000004985 diamines Chemical class 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
FJJYHTVHBVXEEQ-UHFFFAOYSA-N dimethylpropionaldehyde Natural products CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 3
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 3
239000000945 filler Substances 0.000 description 3
239000003063 flame retardant Substances 0.000 description 3
150000002334 glycols Chemical class 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
239000003999 initiator Substances 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 3
238000000465 moulding Methods 0.000 description 3
238000010422 painting Methods 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
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 3
HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
UJBOOUHRTQVGRU-UHFFFAOYSA-N 3-methylcyclohexan-1-one Chemical compound CC1CCCC(=O)C1 UJBOOUHRTQVGRU-UHFFFAOYSA-N 0.000 description 2
KZTROCYBPMKGAW-UHFFFAOYSA-N 4-[[4-amino-3,5-di(propan-2-yl)phenyl]methyl]-2,6-di(propan-2-yl)aniline Chemical compound CC(C)C1=C(N)C(C(C)C)=CC(CC=2C=C(C(N)=C(C(C)C)C=2)C(C)C)=C1 KZTROCYBPMKGAW-UHFFFAOYSA-N 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
229920000877 Melamine resin Polymers 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
239000004721 Polyphenylene oxide 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
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 2
YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
239000003513 alkali Substances 0.000 description 2
229910001854 alkali hydroxide Inorganic materials 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
150000001447 alkali salts Chemical class 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-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
ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
230000006378 damage Effects 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
125000005442 diisocyanate group Chemical group 0.000 description 2
150000002009 diols Chemical class 0.000 description 2
ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical class C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
239000006260 foam Substances 0.000 description 2
239000004872 foam stabilizing agent Substances 0.000 description 2
239000003365 glass fiber Substances 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
229910003475 inorganic filler Inorganic materials 0.000 description 2
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
238000012693 lactam polymerization Methods 0.000 description 2
150000003951 lactams Chemical class 0.000 description 2
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
230000036961 partial effect Effects 0.000 description 2
XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
235000021317 phosphate Nutrition 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
238000006116 polymerization reaction Methods 0.000 description 2
229920001296 polysiloxane Polymers 0.000 description 2
WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 2
229960003656 ricinoleic acid Drugs 0.000 description 2
FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 2
239000007858 starting material Substances 0.000 description 2
230000002195 synergetic effect Effects 0.000 description 2
WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
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 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical class NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
ZFMRPEFNWRGSDW-UHFFFAOYSA-N (2,2-dimethyl-3-oxopropyl) 2-methoxyacetate Chemical compound COCC(=O)OCC(C)(C)C=O ZFMRPEFNWRGSDW-UHFFFAOYSA-N 0.000 description 1
BYYPPVMBDPUHHR-UHFFFAOYSA-N (2-methyl-1-oxopropan-2-yl) acetate Chemical compound CC(=O)OC(C)(C)C=O BYYPPVMBDPUHHR-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
LPMBTLLQQJBUOO-KTKRTIGZSA-N (z)-n,n-bis(2-hydroxyethyl)octadec-9-enamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)N(CCO)CCO LPMBTLLQQJBUOO-KTKRTIGZSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
ZFDWWDZLRKHULH-UHFFFAOYSA-N 1,2-dimethyl-5,6-dihydro-4h-pyrimidine Chemical compound CN1CCCN=C1C ZFDWWDZLRKHULH-UHFFFAOYSA-N 0.000 description 1
GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 1
FCQPNTOQFPJCMF-UHFFFAOYSA-N 1,3-bis[3-(dimethylamino)propyl]urea Chemical compound CN(C)CCCNC(=O)NCCCN(C)C FCQPNTOQFPJCMF-UHFFFAOYSA-N 0.000 description 1
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
GEEGPFGTMRWCID-UHFFFAOYSA-N 1-n,1-n,1-n',1-n'-tetramethylbutane-1,1-diamine Chemical compound CCCC(N(C)C)N(C)C GEEGPFGTMRWCID-UHFFFAOYSA-N 0.000 description 1
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical class NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
RZEWIYUUNKCGKA-UHFFFAOYSA-N 2-(2-hydroxyethylamino)ethanol;octadecanoic acid Chemical compound OCCNCCO.CCCCCCCCCCCCCCCCCC(O)=O RZEWIYUUNKCGKA-UHFFFAOYSA-N 0.000 description 1
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Landscapes

Polyurethanes Or Polyureas (AREA)

CA000562006A 1988-03-21 1988-03-21 Elastomeres renfermant des groupes polyamide et polyuree lies; methode de preparation d'articles moules, elastiques et non cellulaires, a partir de ces elastomeres Expired - Lifetime CA1293085C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000562006A CA1293085C (fr)	1988-03-21	1988-03-21	Elastomeres renfermant des groupes polyamide et polyuree lies; methode de preparation d'articles moules, elastiques et non cellulaires, a partir de ces elastomeres

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000562006A CA1293085C (fr)	1988-03-21	1988-03-21	Elastomeres renfermant des groupes polyamide et polyuree lies; methode de preparation d'articles moules, elastiques et non cellulaires, a partir de ces elastomeres

Publications (1)

Publication Number	Publication Date
CA1293085C true CA1293085C (fr)	1991-12-10

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CA000562006A Expired - Lifetime CA1293085C (fr)	1988-03-21	1988-03-21	Elastomeres renfermant des groupes polyamide et polyuree lies; methode de preparation d'articles moules, elastiques et non cellulaires, a partir de ces elastomeres

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CA (1)	CA1293085C (fr)

1988
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Legal Events

Date	Code	Title	Description
2007-12-10	MKLA	Lapsed

Publication	Publication Date	Title
US4789691A (en)	1988-12-06	Elastomers containing polyamide groups and polyurea groups in bonded form, as well as a process for the preparation of elastic, non-cellullar molded articles from these elastomers
US4774264A (en)	1988-09-27	Process for the production of elastic molded articles
CA1328704C (fr)	1994-04-19	Procede pour la preparation d'articles moules elastiques, non cellulaires ou cellulaires, a base de polyurethane ou de polyurethane-polyuree
US5219973A (en)	1993-06-15	Polyurea rim systems
CA1266743A (fr)	1990-03-13	Articles moules en polyuree de polyurethane optionnellement alveolaire, a caracteristique de demoulage amelioree, et leur preparation
JPH07103211B2 (ja)	1995-11-08	ウレタン基を有するポリ尿素エラストマーの製造方法
JP2592724B2 (ja)	1997-03-19	反応射出成形用ポリウレア樹脂組成物
KR100247881B1 (ko)	2000-04-01	우레탄 그룹을 함유하는 폴리우레아 탄성중합체의 제조방법
US5364852A (en)	1994-11-15	Preparation of compact or cellular elastomers containing urethane and urea groups, and moldings produced therefrom
KR100264939B1 (ko)	2000-09-01	형성 성분으로서 n-퍼에톡실화된 폴리옥시알킬렌 폴리아민의 존재하에 우레탄기 또는 우레탄과 우레아기를 결합상태로 함유하는 탄성 엘라스토머를 제조하는 방법
EP0438696B1 (fr)	1994-11-02	Procédé de préparation d'articles moulés élastiques compacts ou cellulaires à base d'élastomères contenant des groupes N-substitués urée et amide, de tels élastomères et des mélanges de polyoxyalkylène-polyamines, contenant des polyazométhines, appropriés à ce procédé
CA2033444C (fr)	2002-10-15	Production de moulages elastiques compacts ou alveolaires a base d'elastomeres renfermant des groupements de n-benzyluree lies, les elastomeres de ce type et les n-benzylpolyoxyalkylene-polyamines compatible pour cet usage
CA1293085C (fr)	1991-12-10	Elastomeres renfermant des groupes polyamide et polyuree lies; methode de preparation d'articles moules, elastiques et non cellulaires, a partir de ces elastomeres
JP2640363B2 (ja)	1997-08-13	ポリウレタン尿素エラストマーの製造方法
CA1245413A (fr)	1988-11-29	Preparation de pieces moulees en polyurethane- polyuree facultativement cellulaire a l'aide de 2,4- et (ou) 2,6-toluene diisocyanates renfermant le groupe urethane et le groupeisocyanurate
US5153235A (en)	1992-10-06	Production of elastic, compact or cellular moldings based on elastomers containing N-benzylurea groups in bound form, elastomers of this type, and N-benzylpolyoxyalkylene-polyamines which are suitable for this purpose
CA1266945A (fr)	1990-03-20	Preparation d'elastomeres de polyurethane denses ou alveolaires resistant aux tres hautes temperatures
EP0379916B1 (fr)	1993-04-28	Prépolymères à base de polyétherester et les elastomères à partir de ceux-ci
CA2064310A1 (fr)	1992-10-23	Agents de demoulage et utilisation en production d'articles moules
US5239038A (en)	1993-08-24	Cyclohexanedimethanoladipate based prepolymers and reaction injection molded products made therefrom
CA2051236A1 (fr)	1992-03-27	Systeme pour polyuree moulee par injection et reaction
CA2064311A1 (fr)	1992-10-23	Agents de demoulage et utilisation en production d'articles moules
JPS63132920A (ja)	1988-06-04	弾性エラストマ−成形物