CA1265291A - Polymeres composes d'une oxazoline, d'un polyol et d'un polyisocyanate et procede de preparation - Google Patents

Polymeres composes d'une oxazoline, d'un polyol et d'un polyisocyanate et procede de preparation

Info

Publication number: CA1265291A
Authority: CA; Canada
Prior art keywords: oxazoline; polyol; bis; dimethyl; tetramethylene
Prior art date: 1986-09-22
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

CA000518759A

Other languages

English (en)

Inventor

Peggy A. Blackburn

Anil B. Goel

Timothy A. Tufts

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.)

Ashland LLC

Original Assignee

Ashland Oil 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.)

1986-09-22

Filing date

1986-09-22

Publication date

1990-01-30

1986-09-22 Application filed by Ashland Oil Inc filed Critical Ashland Oil Inc

1986-09-22 Priority to CA000518759A priority Critical patent/CA1265291A/fr

1990-01-30 Application granted granted Critical

1990-01-30 Publication of CA1265291A publication Critical patent/CA1265291A/fr

Status Expired legal-status Critical Current

Links

229920005862 polyol Polymers 0.000 title claims abstract description 35
150000003077 polyols Chemical class 0.000 title claims abstract description 34
IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 title claims abstract description 33
229920001228 polyisocyanate Polymers 0.000 title claims abstract description 25
239000005056 polyisocyanate Substances 0.000 title claims abstract description 25
238000000034 method Methods 0.000 title claims description 28
229920000642 polymer Polymers 0.000 title claims description 13
-1 poly(tetramethylene ether) Polymers 0.000 claims description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
150000002009 diols Chemical class 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 9
CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 7
239000012948 isocyanate Substances 0.000 claims description 7
150000002513 isocyanates Chemical class 0.000 claims description 7
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 6
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 claims description 5
UMWUESWLHCAWKP-UHFFFAOYSA-N 2-[4-(4,4-dimethyl-5h-1,3-oxazol-2-yl)butyl]-4,4-dimethyl-5h-1,3-oxazole Chemical compound CC1(C)COC(CCCCC=2OCC(C)(C)N=2)=N1 UMWUESWLHCAWKP-UHFFFAOYSA-N 0.000 claims description 5
NYEZZYQZRQDLEH-UHFFFAOYSA-N 2-ethyl-4,5-dihydro-1,3-oxazole Chemical group CCC1=NCCO1 NYEZZYQZRQDLEH-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
ZGQBEECCVBUKHE-UHFFFAOYSA-N 2-[3-(4,4-dimethyl-5h-1,3-oxazol-2-yl)propyl]-4,4-dimethyl-5h-1,3-oxazole Chemical compound CC1(C)COC(CCCC=2OCC(C)(C)N=2)=N1 ZGQBEECCVBUKHE-UHFFFAOYSA-N 0.000 claims description 3
OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims description 3
235000020778 linoleic acid Nutrition 0.000 claims description 3
NCUMTEROGQOYDG-UHFFFAOYSA-N 2-[10-(4,4-dimethyl-5h-1,3-oxazol-2-yl)decyl]-4,4-dimethyl-5h-1,3-oxazole Chemical compound CC1(C)COC(CCCCCCCCCCC=2OCC(C)(C)N=2)=N1 NCUMTEROGQOYDG-UHFFFAOYSA-N 0.000 claims description 2
125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 claims description 2
FREPJBZLNPPGDM-UHFFFAOYSA-N 4,4-dimethyl-2-undecyl-5h-1,3-oxazole Chemical group CCCCCCCCCCCC1=NC(C)(C)CO1 FREPJBZLNPPGDM-UHFFFAOYSA-N 0.000 claims description 2
UJZWHHMQORQWGC-UHFFFAOYSA-N 4,4-dimethyl-5h-1,2-oxazole Chemical compound CC1(C)CON=C1 UJZWHHMQORQWGC-UHFFFAOYSA-N 0.000 claims description 2
SPYHJGHRAMENMS-UHFFFAOYSA-N 5-(2-hydroxypentyl)-2,4-dimethyl-5h-1,3-oxazol-4-ol Chemical group CCCC(O)CC1OC(C)=NC1(C)O SPYHJGHRAMENMS-UHFFFAOYSA-N 0.000 claims description 2
125000002877 alkyl aryl group Chemical group 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000005442 diisocyanate group Chemical group 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
UFUAASKHUNQXBP-UHFFFAOYSA-N 2-[2-(4,4-dimethyl-5h-1,3-oxazol-2-yl)ethyl]-4,4-dimethyl-5h-1,3-oxazole Chemical compound CC1(C)COC(CCC=2OCC(C)(C)N=2)=N1 UFUAASKHUNQXBP-UHFFFAOYSA-N 0.000 claims 1
KOAMXHRRVFDWRQ-UHFFFAOYSA-N 4,4-dimethyl-5h-1,3-oxazole Chemical compound CC1(C)COC=N1 KOAMXHRRVFDWRQ-UHFFFAOYSA-N 0.000 claims 1
YDBFJOPKKFFWLD-UHFFFAOYSA-N 4,5-dihydro-1,3-oxazole;2-ethyl-4,5-dihydro-1,3-oxazole Chemical compound C1CN=CO1.CCC1=NCCO1 YDBFJOPKKFFWLD-UHFFFAOYSA-N 0.000 claims 1
238000004519 manufacturing process Methods 0.000 abstract 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000011521 glass Substances 0.000 description 8
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
239000002131 composite material Substances 0.000 description 5
239000000463 material Substances 0.000 description 5
229920000570 polyether Polymers 0.000 description 4
238000006116 polymerization reaction Methods 0.000 description 4
239000000243 solution Substances 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
150000002918 oxazolines Chemical class 0.000 description 3
230000000704 physical effect Effects 0.000 description 3
239000004814 polyurethane Substances 0.000 description 3
229920002635 polyurethane Polymers 0.000 description 3
229920001187 thermosetting polymer Polymers 0.000 description 3
RJWLXGOSIRVRAR-UHFFFAOYSA-N 2,4-dimethylbenzene-1,3-diol Chemical compound CC1=CC=C(O)C(C)=C1O RJWLXGOSIRVRAR-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
229910000831 Steel Inorganic materials 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
239000004744 fabric Substances 0.000 description 2
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
230000003993 interaction Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000011417 postcuring Methods 0.000 description 2
YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
239000010959 steel Substances 0.000 description 2
239000004634 thermosetting polymer Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
GFNDFCFPJQPVQL-UHFFFAOYSA-N 1,12-diisocyanatododecane Chemical compound O=C=NCCCCCCCCCCCCN=C=O GFNDFCFPJQPVQL-UHFFFAOYSA-N 0.000 description 1
OYWRDHBGMCXGFY-UHFFFAOYSA-N 1,2,3-triazinane Chemical compound C1CNNNC1 OYWRDHBGMCXGFY-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
IKYNWXNXXHWHLL-UHFFFAOYSA-N 1,3-diisocyanatopropane Chemical compound O=C=NCCCN=C=O IKYNWXNXXHWHLL-UHFFFAOYSA-N 0.000 description 1
150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
FVLCBDPSQUONII-UHFFFAOYSA-N 1,4-diisocyanato-2,3-dimethylbutane Chemical compound O=C=NCC(C)C(C)CN=C=O FVLCBDPSQUONII-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
CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
SIZPGZFVROGOIR-UHFFFAOYSA-N 1,4-diisocyanatonaphthalene Chemical compound C1=CC=C2C(N=C=O)=CC=C(N=C=O)C2=C1 SIZPGZFVROGOIR-UHFFFAOYSA-N 0.000 description 1
FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 1
DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 description 1
LCVCUJWKJNFDMY-UHFFFAOYSA-N 2,2-diphenylpropane-1,1-diol Chemical compound C=1C=CC=CC=1C(C(O)O)(C)C1=CC=CC=C1 LCVCUJWKJNFDMY-UHFFFAOYSA-N 0.000 description 1
DWVXFVWWARTDCQ-UHFFFAOYSA-N 2-ethylbenzene-1,3-diol Chemical compound CCC1=C(O)C=CC=C1O DWVXFVWWARTDCQ-UHFFFAOYSA-N 0.000 description 1
GSOSWVGCAPGSDU-UHFFFAOYSA-N 3,6-dimethylbenzene-1,2,4-triol Chemical compound CC1=CC(O)=C(C)C(O)=C1O GSOSWVGCAPGSDU-UHFFFAOYSA-N 0.000 description 1
BEJQXBXPRXFJDP-UHFFFAOYSA-N 3-(3,3-dihydroxypropoxy)propane-1,1-diol Chemical class OC(O)CCOCCC(O)O BEJQXBXPRXFJDP-UHFFFAOYSA-N 0.000 description 1
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 1
BQAUXFAQNIKTPW-UHFFFAOYSA-N C=C.C=C.C=C.C=C.N=C=O.N=C=O Chemical compound C=C.C=C.C=C.C=C.N=C=O.N=C=O BQAUXFAQNIKTPW-UHFFFAOYSA-N 0.000 description 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical class CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
238000007605 air drying Methods 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
AAWPAGFROKXNEN-UHFFFAOYSA-N benzene-1,3-diol;prop-1-ene Chemical compound CC=C.OC1=CC=CC(O)=C1 AAWPAGFROKXNEN-UHFFFAOYSA-N 0.000 description 1
230000001588 bifunctional effect Effects 0.000 description 1
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
239000001273 butane Substances 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
VEIOBOXBGYWJIT-UHFFFAOYSA-N cyclohexane;methanol Chemical compound OC.OC.C1CCCCC1 VEIOBOXBGYWJIT-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
229910002804 graphite Inorganic materials 0.000 description 1
239000010439 graphite Substances 0.000 description 1
239000006082 mold release agent Substances 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
229920002857 polybutadiene Polymers 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
239000004417 polycarbonate 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
229920001223 polyethylene glycol Polymers 0.000 description 1
229920006324 polyoxymethylene Polymers 0.000 description 1
229920006389 polyphenyl polymer Polymers 0.000 description 1
229920006295 polythiol Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000010107 reaction injection moulding Methods 0.000 description 1
239000011208 reinforced composite material Substances 0.000 description 1
230000002787 reinforcement Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
125000006850 spacer group Chemical group 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
239000012970 tertiary amine catalyst Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
239000013638 trimer Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Landscapes

Polyurethanes Or Polyureas (AREA)

CA000518759A 1986-09-22 1986-09-22 Polymeres composes d'une oxazoline, d'un polyol et d'un polyisocyanate et procede de preparation Expired CA1265291A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000518759A CA1265291A (fr)	1986-09-22	1986-09-22	Polymeres composes d'une oxazoline, d'un polyol et d'un polyisocyanate et procede de preparation

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000518759A CA1265291A (fr)	1986-09-22	1986-09-22	Polymeres composes d'une oxazoline, d'un polyol et d'un polyisocyanate et procede de preparation

Publications (1)

Publication Number	Publication Date
CA1265291A true CA1265291A (fr)	1990-01-30

Family

ID=4133988

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000518759A Expired CA1265291A (fr)	1986-09-22	1986-09-22	Polymeres composes d'une oxazoline, d'un polyol et d'un polyisocyanate et procede de preparation

Country Status (1)

Country	Link
CA (1)	CA1265291A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN117924682B (zh) *	2024-01-24	2025-03-25	深圳市久信达科技有限公司	耐老化聚乳酸材料的制备方法及耐老化聚乳酸材料

1986
- 1986-09-22 CA CA000518759A patent/CA1265291A/fr not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN117924682B (zh) *	2024-01-24	2025-03-25	深圳市久信达科技有限公司	耐老化聚乳酸材料的制备方法及耐老化聚乳酸材料

Legal Events

Date	Code	Title	Description
1998-01-30	MKLA	Lapsed

Publication	Publication Date	Title
US4562240A (en)	1985-12-31	Bicyclic amide acetal/polyol/polyisocyanate polymers
US3817939A (en)	1974-06-18	Organic carbonate salts as isocyanate trimerization catalysts
JPH0138804B2 (fr)	1989-08-16
KR880001142B1 (ko)	1988-07-01	폴리머 얼로이의 제조방법 및 반응 사출 성형 생성물
US4640969A (en)	1987-02-03	Oxazoline/polyol/polyisocyanate polymers and process
US4558114A (en)	1985-12-10	Polymers derived from polyisocyanates, bicyclic amide acetals and oxazolines
JPS6377917A (ja)	1988-04-08	オキサゾリン／ポリオ−ル／ポリイソシアネ−ト重合体およびその製造方法
US5223598A (en)	1993-06-29	Plural liquid pack type, heat-curable polyisocyanate-polyol-polyepoxy resin composition and process for producing a shaped resin article therefrom
US4614786A (en)	1986-09-30	Stable isocyanate/epoxide prepolymers and thermoset polyurethanes produced therefrom
US3236812A (en)	1966-02-22	Interfacial polymerization of polyurethanes
JPH01156318A (ja)	1989-06-19	固体含量の多い重合体ポリオール及びその製法
US4540767A (en)	1985-09-10	Polymers based on bicyclic amide acetals/polyepoxides/polyisocyanates
US4757123A (en)	1988-07-12	Method for the preparation of rigid cast or transfer molded thermoset polyisocyanurate compositions
CA1299794C (fr)	1992-04-28	Materiau composite a densite elevee, surtout a base de polyisocyanurate
EP0260339B1 (fr)	1991-03-13	Polymères d'oxazoline/polyol/polyisocyanate et procédé
US4897430A (en)	1990-01-30	One Component polyurea
CA1172009A (fr)	1984-08-07	Elastomeres renforces, moules par injection- reaction
US4767796A (en)	1988-08-30	Hard segment containing prepolymers from cycloalkane diols
US4582890A (en)	1986-04-15	Bicyclic amide acetal/polyamine/polyisocyanate polymers
EP0279017A2 (fr)	1988-08-24	Procédé de copolymérisation d'acétals d'amide bicycliques et de polyisocyanates
US4707532A (en)	1987-11-17	Copolymerization of blocked polyisocyanates with bicyclic amide acetals
US4704409A (en)	1987-11-03	Reaction products of polyols with bicyclic amide acetals and their application in polyurethane polymers
US4699968A (en)	1987-10-13	Water as a partial extender in polyurethane formulations
WO1992001009A1 (fr)	1992-01-23	Composition renfermant des alcanolamines et des polyisocyanates
US4600796A (en)	1986-07-15	Reaction products of alkanol amines with bicyclic amide acetals and their application in polyurethane polymers

CA1265291A - Polymeres composes d'une oxazoline, d'un polyol et d'un polyisocyanate et procede de preparation - Google Patents

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