CN103102706A - Polyurethane high-temperature-resistant anti-rutting modifier for road asphalt - Google Patents
Polyurethane high-temperature-resistant anti-rutting modifier for road asphalt Download PDFInfo
- Publication number
- CN103102706A CN103102706A CN2013100360411A CN201310036041A CN103102706A CN 103102706 A CN103102706 A CN 103102706A CN 2013100360411 A CN2013100360411 A CN 2013100360411A CN 201310036041 A CN201310036041 A CN 201310036041A CN 103102706 A CN103102706 A CN 103102706A
- Authority
- CN
- China
- Prior art keywords
- modifier
- small molecules
- polyol
- chainextender
- polyurethane
- Prior art date
- 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.)
- Granted
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- 239000010426 asphalt Substances 0.000 title claims abstract description 82
- 239000003607 modifier Substances 0.000 title claims abstract description 40
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 27
- 239000004814 polyurethane Substances 0.000 title claims abstract description 21
- -1 polymethylene isocyanate Polymers 0.000 claims abstract description 60
- 239000004970 Chain extender Substances 0.000 claims abstract description 38
- 229920005862 polyol Polymers 0.000 claims abstract description 28
- 239000011159 matrix material Substances 0.000 claims abstract description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 239000002253 acid Substances 0.000 claims abstract description 23
- 150000003077 polyols Chemical class 0.000 claims abstract description 23
- 229920000642 polymer Polymers 0.000 claims abstract description 22
- 229920000768 polyamine Polymers 0.000 claims abstract description 19
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 84
- 150000003384 small molecules Chemical class 0.000 claims description 38
- 239000000126 substance Substances 0.000 claims description 30
- 229920002521 macromolecule Polymers 0.000 claims description 24
- 239000005056 polyisocyanate Substances 0.000 claims description 19
- 229920001228 polyisocyanate Polymers 0.000 claims description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 239000003112 inhibitor Substances 0.000 claims description 14
- 230000003647 oxidation Effects 0.000 claims description 14
- 238000007254 oxidation reaction Methods 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 13
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- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 13
- 229920001971 elastomer Polymers 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
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- 229920001577 copolymer Polymers 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 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 8
- 229920002121 Hydroxyl-terminated polybutadiene Polymers 0.000 claims description 7
- 239000004698 Polyethylene Substances 0.000 claims description 7
- 239000006096 absorbing agent Substances 0.000 claims description 7
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 7
- 229920000573 polyethylene Polymers 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 6
- 239000000539 dimer Substances 0.000 claims description 6
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
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- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 3
- 239000005038 ethylene vinyl acetate Substances 0.000 claims description 3
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- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 claims description 3
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 3
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- RUQNFHWKALNWAE-UHFFFAOYSA-N 3-(3-hydroxyphenoxy)propane-1,1-diol Chemical compound OC(CCOC1=CC(O)=CC=C1)O RUQNFHWKALNWAE-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- AMYRSDHRQFEUCF-UHFFFAOYSA-N buta-1,3-diene 2-phenylethenol Chemical compound C=CC=C.OC=CC1=CC=CC=C1 AMYRSDHRQFEUCF-UHFFFAOYSA-N 0.000 claims description 2
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 claims description 2
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- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 150000001993 dienes Chemical class 0.000 abstract description 2
- 125000005442 diisocyanate group Chemical group 0.000 abstract 2
- 239000000463 material Substances 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 7
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- 238000012986 modification Methods 0.000 description 7
- 238000013019 agitation Methods 0.000 description 6
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 6
- 229910052797 bismuth Inorganic materials 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 5
- 150000001718 carbodiimides Chemical class 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- OEOIWYCWCDBOPA-UHFFFAOYSA-N 6-methyl-heptanoic acid Chemical compound CC(C)CCCCC(O)=O OEOIWYCWCDBOPA-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
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- OYBMVMAXKOGYDC-UHFFFAOYSA-N CTPB Chemical compound CCCCCCCCCCCCCCCC1=CC=CC(OCC)=C1C(=O)NC1=CC=C(Cl)C(C(F)(F)F)=C1 OYBMVMAXKOGYDC-UHFFFAOYSA-N 0.000 description 2
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
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- 150000002917 oxazolidines Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003214 poly(methacrylonitrile) Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 238000010998 test method Methods 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
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Landscapes
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
Claims (10)
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CN201310036041.1A CN103102706B (en) | 2013-01-22 | 2013-01-22 | Polyurethane high-temperature-resistant anti-rutting modifier for road asphalt |
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CN201310036041.1A CN103102706B (en) | 2013-01-22 | 2013-01-22 | Polyurethane high-temperature-resistant anti-rutting modifier for road asphalt |
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CN103102706B CN103102706B (en) | 2015-06-10 |
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CN102464892A (en) * | 2010-11-13 | 2012-05-23 | 烟台万华聚氨酯股份有限公司 | Composite polyurethane modifier for road asphalt |
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