CA1093571A - Polyesterpolyols contenant du glutarate et produits de polyurethanne qui en derivent - Google Patents

Polyesterpolyols contenant du glutarate et produits de polyurethanne qui en derivent

Info

Publication number: CA1093571A
Authority: CA; Canada
Prior art keywords: isocyanate; polyester; hydroxyl terminated; acid; tris
Prior art date: 1978-04-04
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

CA300,418A

Other languages

English (en)

Inventor

William H. Cook

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.)

Fabridyne Inc

Original Assignee

Fabridyne 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.)

1978-04-04

Filing date

1978-04-04

Publication date

1981-01-13

1978-04-04 Application filed by Fabridyne Inc filed Critical Fabridyne Inc

1978-04-04 Priority to CA300,418A priority Critical patent/CA1093571A/fr

1981-01-13 Application granted granted Critical

1981-01-13 Publication of CA1093571A publication Critical patent/CA1093571A/fr

Status Expired legal-status Critical Current

Links

JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 title claims abstract description 93
239000000203 mixture Substances 0.000 title claims abstract description 61
239000004814 polyurethane Substances 0.000 title abstract description 41
229920002635 polyurethane Polymers 0.000 title abstract description 32
229920005906 polyester polyol Polymers 0.000 title abstract description 14
229920000728 polyester Polymers 0.000 claims abstract description 180
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 123
238000006243 chemical reaction Methods 0.000 claims abstract description 106
-1 coatings Substances 0.000 claims abstract description 64
229920005862 polyol Chemical group 0.000 claims abstract description 63
150000003077 polyols Chemical group 0.000 claims abstract description 62
239000000806 elastomer Substances 0.000 claims abstract description 50
229920001971 elastomer Polymers 0.000 claims abstract description 47
239000003054 catalyst Substances 0.000 claims abstract description 44
150000002009 diols Chemical group 0.000 claims abstract description 18
239000012948 isocyanate Substances 0.000 claims description 63
238000000034 method Methods 0.000 claims description 62
150000002513 isocyanates Chemical class 0.000 claims description 58
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 54
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 48
239000002253 acid Substances 0.000 claims description 48
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 45
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 43
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 39
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 35
150000004985 diamines Chemical class 0.000 claims description 34
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 33
238000005809 transesterification reaction Methods 0.000 claims description 32
125000004432 carbon atom Chemical group C* 0.000 claims description 31
150000002148 esters Chemical class 0.000 claims description 29
239000000243 solution Substances 0.000 claims description 29
239000007788 liquid Substances 0.000 claims description 28
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 26
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 25
238000010438 heat treatment Methods 0.000 claims description 24
238000004821 distillation Methods 0.000 claims description 23
150000002334 glycols Chemical class 0.000 claims description 22
239000003795 chemical substances by application Substances 0.000 claims description 21
230000000694 effects Effects 0.000 claims description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
125000005442 diisocyanate group Chemical group 0.000 claims description 19
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 19
150000004984 aromatic diamines Chemical class 0.000 claims description 18
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 16
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 15
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 15
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 13
239000004970 Chain extender Substances 0.000 claims description 13
238000012545 processing Methods 0.000 claims description 13
150000003673 urethanes Chemical class 0.000 claims description 13
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 12
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 12
239000007983 Tris buffer Substances 0.000 claims description 12
230000003197 catalytic effect Effects 0.000 claims description 12
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 12
239000001361 adipic acid Substances 0.000 claims description 11
235000011037 adipic acid Nutrition 0.000 claims description 11
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
150000007513 acids Chemical class 0.000 claims description 10
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 10
229920005989 resin Polymers 0.000 claims description 10
239000011347 resin Substances 0.000 claims description 10
239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 9
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 9
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 9
150000002483 hydrogen compounds Chemical class 0.000 claims description 8
230000001737 promoting effect Effects 0.000 claims description 8
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 7
125000006353 oxyethylene group Chemical group 0.000 claims description 7
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 7
RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 claims description 6
OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 claims description 6
VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 claims description 6
ICLCCFKUSALICQ-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanato-3-methylphenyl)-2-methylbenzene Chemical group C1=C(N=C=O)C(C)=CC(C=2C=C(C)C(N=C=O)=CC=2)=C1 ICLCCFKUSALICQ-UHFFFAOYSA-N 0.000 claims description 6
QZWKEPYTBWZJJA-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine-4,4'-diisocyanate Chemical group C1=C(N=C=O)C(OC)=CC(C=2C=C(OC)C(N=C=O)=CC=2)=C1 QZWKEPYTBWZJJA-UHFFFAOYSA-N 0.000 claims description 6
239000005058 Isophorone diisocyanate Substances 0.000 claims description 6
229920006311 Urethane elastomer Polymers 0.000 claims description 6
150000008064 anhydrides Chemical class 0.000 claims description 6
DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 claims description 6
NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 6
229920003225 polyurethane elastomer Polymers 0.000 claims description 6
SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 claims description 5
NPOVTGVGOBJZPY-UHFFFAOYSA-N 1-isocyanato-3-methoxybenzene Chemical compound COC1=CC=CC(N=C=O)=C1 NPOVTGVGOBJZPY-UHFFFAOYSA-N 0.000 claims description 5
238000009833 condensation Methods 0.000 claims description 5
230000005494 condensation Effects 0.000 claims description 5
239000005056 polyisocyanate Substances 0.000 claims description 5
RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 claims description 5
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 5
ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 claims description 4
VZDIRINETBAVAV-UHFFFAOYSA-N 2,4-diisocyanato-1-methylcyclohexane Chemical compound CC1CCC(N=C=O)CC1N=C=O VZDIRINETBAVAV-UHFFFAOYSA-N 0.000 claims description 4
YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
229920001228 polyisocyanate Polymers 0.000 claims description 4
WRRQKFXVKRQPDB-UHFFFAOYSA-N 2-(2-aminophenyl)sulfanylaniline Chemical compound NC1=CC=CC=C1SC1=CC=CC=C1N WRRQKFXVKRQPDB-UHFFFAOYSA-N 0.000 claims description 3
XEZPSTVEIZNGRR-UHFFFAOYSA-N 2-amino-5-[(4-amino-3-methoxycarbonylphenyl)methyl]benzoic acid methyl ester Chemical compound C1=C(N)C(C(=O)OC)=CC(CC=2C=C(C(N)=CC=2)C(=O)OC)=C1 XEZPSTVEIZNGRR-UHFFFAOYSA-N 0.000 claims description 3
WECDUOXQLAIPQW-UHFFFAOYSA-N 4,4'-Methylene bis(2-methylaniline) Chemical compound C1=C(N)C(C)=CC(CC=2C=C(C)C(N)=CC=2)=C1 WECDUOXQLAIPQW-UHFFFAOYSA-N 0.000 claims description 3
IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 claims description 3
LKHVCEWNPKEPBT-UHFFFAOYSA-N 4-[(4-amino-3-methoxyphenyl)methyl]-2-methoxyaniline Chemical compound C1=C(N)C(OC)=CC(CC=2C=C(OC)C(N)=CC=2)=C1 LKHVCEWNPKEPBT-UHFFFAOYSA-N 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000001246 bromo group Chemical group Br* 0.000 claims description 2
ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 claims 18
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims 8
XMUZQOKACOLCSS-UHFFFAOYSA-N [2-(hydroxymethyl)phenyl]methanol Chemical class OCC1=CC=CC=C1CO XMUZQOKACOLCSS-UHFFFAOYSA-N 0.000 claims 6
238000006136 alcoholysis reaction Methods 0.000 claims 6
125000001142 dicarboxylic acid group Chemical group 0.000 claims 5
230000007935 neutral effect Effects 0.000 claims 5
KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 claims 4
150000005690 diesters Chemical class 0.000 claims 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 2
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 2
229920006324 polyoxymethylene Polymers 0.000 claims 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims 1
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
229910052794 bromium Inorganic materials 0.000 claims 1
239000000460 chlorine Substances 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
229960004279 formaldehyde Drugs 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 31
XTDYIOOONNVFMA-UHFFFAOYSA-N dimethyl pentanedioate Chemical compound COC(=O)CCCC(=O)OC XTDYIOOONNVFMA-UHFFFAOYSA-N 0.000 abstract description 12
239000000376 reactant Substances 0.000 abstract description 10
239000000543 intermediate Substances 0.000 abstract description 8
239000006260 foam Substances 0.000 abstract description 5
238000000576 coating method Methods 0.000 abstract description 4
230000002939 deleterious effect Effects 0.000 abstract description 3
239000000853 adhesive Substances 0.000 abstract description 2
230000001070 adhesive effect Effects 0.000 abstract description 2
230000004048 modification Effects 0.000 abstract 1
238000012986 modification Methods 0.000 abstract 1
239000004014 plasticizer Substances 0.000 abstract 1
229920001169 thermoplastic Polymers 0.000 abstract 1
239000004416 thermosoftening plastic Substances 0.000 abstract 1
239000000047 product Substances 0.000 description 59
239000011541 reaction mixture Substances 0.000 description 21
230000008569 process Effects 0.000 description 14
150000001875 compounds Chemical class 0.000 description 13
230000008901 benefit Effects 0.000 description 12
230000002829 reductive effect Effects 0.000 description 12
229960005088 urethane Drugs 0.000 description 12
235000019589 hardness Nutrition 0.000 description 11
238000004519 manufacturing process Methods 0.000 description 11
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 10
238000002156 mixing Methods 0.000 description 9
239000007787 solid Substances 0.000 description 9
IDLCDDZNXSUZGD-UHFFFAOYSA-N bis(2-hydroxyethyl) pentanedioate Chemical compound OCCOC(=O)CCCC(=O)OCCO IDLCDDZNXSUZGD-UHFFFAOYSA-N 0.000 description 8
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 8
239000011521 glass Substances 0.000 description 8
230000000704 physical effect Effects 0.000 description 8
150000003254 radicals Chemical class 0.000 description 8
206010001497 Agitation Diseases 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
230000032683 aging Effects 0.000 description 7
238000013019 agitation Methods 0.000 description 7
239000000539 dimer Substances 0.000 description 7
230000007062 hydrolysis Effects 0.000 description 7
238000006460 hydrolysis reaction Methods 0.000 description 7
150000002500 ions Chemical class 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
229940094938 stannous 2-ethylhexanoate Drugs 0.000 description 7
238000003860 storage Methods 0.000 description 7
IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 7
KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
229940067597 azelate Drugs 0.000 description 6
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
238000005266 casting Methods 0.000 description 6
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 6
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
230000006835 compression Effects 0.000 description 5
238000007906 compression Methods 0.000 description 5
238000001816 cooling Methods 0.000 description 5
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
239000001294 propane Substances 0.000 description 5
239000005297 pyrex Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 4
229920001730 Moisture cure polyurethane Polymers 0.000 description 4
WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 4
125000001931 aliphatic group Chemical group 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
150000007942 carboxylates Chemical class 0.000 description 4
150000001991 dicarboxylic acids Chemical class 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
238000005191 phase separation Methods 0.000 description 4
WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 4
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 4
150000004072 triols Chemical group 0.000 description 4
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
GDPHJJGNQBPAAI-UHFFFAOYSA-N NC(=O)OCC.C(CCCC(=O)O)(=O)O Chemical class NC(=O)OCC.C(CCCC(=O)O)(=O)O GDPHJJGNQBPAAI-UHFFFAOYSA-N 0.000 description 3
CADNMISJDLVPCK-LSDHHAIUSA-N Roccellic acid Chemical compound CCCCCCCCCCCC[C@@H](C(O)=O)[C@H](C)C(O)=O CADNMISJDLVPCK-LSDHHAIUSA-N 0.000 description 3
PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 3
229960004063 propylene glycol Drugs 0.000 description 3
235000013772 propylene glycol Nutrition 0.000 description 3
239000002994 raw material Substances 0.000 description 3
230000036647 reaction Effects 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
230000009467 reduction Effects 0.000 description 3
238000010992 reflux Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
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Landscapes

Polyurethanes Or Polyureas (AREA)

CA300,418A 1978-04-04 1978-04-04 Polyesterpolyols contenant du glutarate et produits de polyurethanne qui en derivent Expired CA1093571A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA300,418A CA1093571A (fr)	1978-04-04	1978-04-04	Polyesterpolyols contenant du glutarate et produits de polyurethanne qui en derivent

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA300,418A CA1093571A (fr)	1978-04-04	1978-04-04	Polyesterpolyols contenant du glutarate et produits de polyurethanne qui en derivent

Publications (1)

Publication Number	Publication Date
CA1093571A true CA1093571A (fr)	1981-01-13

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CA300,418A Expired CA1093571A (fr)	1978-04-04	1978-04-04	Polyesterpolyols contenant du glutarate et produits de polyurethanne qui en derivent

Country Status (1)

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CA (1)	CA1093571A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN117247539A (zh) *	2023-09-28	2023-12-19	中国科学院宁波材料技术与工程研究所	一种超支化聚酯酰胺多元醇及其制备方法和应用

1978
- 1978-04-04 CA CA300,418A patent/CA1093571A/fr not_active Expired

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN117247539A (zh) *	2023-09-28	2023-12-19	中国科学院宁波材料技术与工程研究所	一种超支化聚酯酰胺多元醇及其制备方法和应用
CN117247539B (zh) *	2023-09-28	2024-03-22	中国科学院宁波材料技术与工程研究所	一种超支化聚酯酰胺多元醇及其制备方法和应用

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1998-01-20	MKEX	Expiry

Publication	Publication Date	Title
EP0193872B1 (fr)	1993-03-31	Agents d'allongement de chaîne di(alkylthio)diamine pour élastomères de polyuréthane
KR20190076963A (ko)	2019-07-02	바이오 재생 가능 고성능 폴리에스테르 폴리올
US20070049719A1 (en)	2007-03-01	Process for the production of melt-processable polyurethanes
US3012991A (en)	1961-12-12	Chemical reactions
KR910000858B1 (ko)	1991-02-11	열경화성 성형 조성물 및 그의 제조 방법
US4096129A (en)	1978-06-20	Glutarate-containing polyesterpolyols, methods of preparation and polyurethane compositions derived therefrom
US5093382A (en)	1992-03-03	Preparation of foams using polyfunctional organic acids
US3957753A (en)	1976-05-18	Liquid hydroxy-terminated polyesters
US3775354A (en)	1973-11-27	Polyurethane elastomers based on poly(epsilon-caprolactone)polyols
JPH07149859A (ja)	1995-06-13	芳香族ポリイソシアヌレート樹脂およびその製法
US4384083A (en)	1983-05-17	Thermoplastic adhesive
EP0240196B1 (fr)	1992-10-07	Utilisation de polyamines polymériques pour la préparation de polyuréthane/polyurée ou polyurée.
US7763683B2 (en)	2010-07-27	Polyester polyols, a process for the production thereof and the use thereof
JP3493648B2 (ja)	2004-02-03	２液注型用ポリウレタンエラストマー組成物、及びポリウレタンエラストマーの製造方法
JPH09183826A (ja)	1997-07-15	一体スキン層付ウレタンフォーム成形品の製造方法
CA1093571A (fr)	1981-01-13	Polyesterpolyols contenant du glutarate et produits de polyurethanne qui en derivent
CA1166395A (fr)	1984-04-24	Compositions pour colle au polyurethane
US4006122A (en)	1977-02-01	Polyester-amides prepared from polymalonates and isocyanates
US4322364A (en)	1982-03-30	Modified isocyanate compositions
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