CN1922274A - Polyurethane composition and molded article thereof - Google Patents
Polyurethane composition and molded article thereof Download PDFInfo
- Publication number
- CN1922274A CN1922274A CN 200580005572 CN200580005572A CN1922274A CN 1922274 A CN1922274 A CN 1922274A CN 200580005572 CN200580005572 CN 200580005572 CN 200580005572 A CN200580005572 A CN 200580005572A CN 1922274 A CN1922274 A CN 1922274A
- Authority
- CN
- China
- Prior art keywords
- compound
- carbonatoms
- polyurethane composition
- normal olefine
- weight parts
- 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
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 44
- 239000004814 polyurethane Substances 0.000 title claims abstract description 31
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 31
- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 45
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 20
- -1 urethane compound Chemical class 0.000 claims abstract description 20
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000004593 Epoxy Substances 0.000 claims description 8
- 239000011159 matrix material Substances 0.000 claims description 8
- 238000000465 moulding Methods 0.000 claims description 8
- 239000000539 dimer Substances 0.000 claims description 7
- 239000004711 α-olefin Substances 0.000 claims description 5
- 150000002118 epoxides Chemical class 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract description 6
- 230000007613 environmental effect Effects 0.000 abstract description 5
- 239000005556 hormone Substances 0.000 abstract description 5
- 229940088597 hormone Drugs 0.000 abstract description 5
- 229920005862 polyol Polymers 0.000 abstract description 4
- 150000003077 polyols Chemical class 0.000 abstract description 4
- 125000003700 epoxy group Chemical group 0.000 abstract 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 47
- 239000004902 Softening Agent Substances 0.000 description 37
- 238000012986 modification Methods 0.000 description 25
- 230000004048 modification Effects 0.000 description 25
- 230000000052 comparative effect Effects 0.000 description 22
- 239000003795 chemical substances by application Substances 0.000 description 18
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 17
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 14
- 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 14
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 150000001336 alkenes Chemical class 0.000 description 8
- 238000007598 dipping method Methods 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 8
- 150000002924 oxiranes Chemical class 0.000 description 8
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical group CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 5
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000013008 thixotropic agent Substances 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 235000012204 lemonade/lime carbonate Nutrition 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 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 3
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 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
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N n-alpha-hexadecene Natural products CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 229940095068 tetradecene Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- OCEJORLHBDCNQE-UHFFFAOYSA-N 1-hexan-2-yloxyhexane Chemical compound CCCCCCOC(C)CCCC OCEJORLHBDCNQE-UHFFFAOYSA-N 0.000 description 1
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-AAKVHIHISA-N 2,3-bis[[(z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (z)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(O)CCCCCC)COC(=O)CCCCCCC\C=C/CC(O)CCCCCC ZEMPKEQAKRGZGQ-AAKVHIHISA-N 0.000 description 1
- VRHIASSZFFGDKZ-UHFFFAOYSA-N 2-dodecyl-2-tetradecyloxirane Chemical compound CCCCCCCCCCCCCCC1(CCCCCCCCCCCC)CO1 VRHIASSZFFGDKZ-UHFFFAOYSA-N 0.000 description 1
- FQFQJTCMCMNHFO-UHFFFAOYSA-N 2-hexadecyl-2-tetradecyloxirane Chemical compound CCCCCCCCCCCCCCCCC1(CCCCCCCCCCCCCC)CO1 FQFQJTCMCMNHFO-UHFFFAOYSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- MEUHELKJCGXSBF-UHFFFAOYSA-N 5-methylideneundecane Chemical group CCCCCCC(=C)CCCC MEUHELKJCGXSBF-UHFFFAOYSA-N 0.000 description 1
- ALLHOOZJEFGTPW-UHFFFAOYSA-N 7-methylidenepentadecane Chemical group CCCCCCCCC(=C)CCCCCC ALLHOOZJEFGTPW-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- FTXXNPQBSDVDFS-UHFFFAOYSA-N C(CCCCCCCCC)C(C)OCCCCCCCCCCCC Chemical compound C(CCCCCCCCC)C(C)OCCCCCCCCCCCC FTXXNPQBSDVDFS-UHFFFAOYSA-N 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 210000004899 c-terminal region Anatomy 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000012774 insulation material Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 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 1
- 238000003475 lamination Methods 0.000 description 1
- DSSXKBBEJCDMBT-UHFFFAOYSA-M lead(2+);octanoate Chemical compound [Pb+2].CCCCCCCC([O-])=O DSSXKBBEJCDMBT-UHFFFAOYSA-M 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000003863 metallic catalyst Substances 0.000 description 1
- KPNBUPJZFJCCIQ-LURJTMIESA-N methyl L-lysinate Chemical compound COC(=O)[C@@H](N)CCCCN KPNBUPJZFJCCIQ-LURJTMIESA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920001195 polyisoprene Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 230000003678 scratch resistant effect Effects 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000010454 slate Substances 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Polyurethanes Or Polyureas (AREA)
Abstract
A polyurethane composition comprising a compound and a compound (B). The compound is a urethane compound obtained by reacting a polyisocyanate with 100 parts by weight of a polyol in a ratio of NCO/OH equivalent ratio of more than 0.5 and less than 15; the compound (B) is a compound selected from an epoxy group of a linear olefin compound having 6 or more carbon atoms, an oligomer of a linear olefin compound having 6 or more carbon atoms, or an oligomer of a linear olefin compound having 6 or more carbon atoms, and the amount of the compound (B) is more than 5 parts by weight and less than 400 parts by weight based on 100 parts by weight of the polyol. The composition is a polyurethane composition free from environmental hormone concerns.
Description
Technical field
The present invention relates to polyurethane composition and molding thereof.
Background technology
Polyurethane composition passes through used polyvalent alcohol, polymeric polyisocyanate, softening agent, other additive appropriate combination, can carry out multiple adjustment to chemistry, physical properties, it is used to the various uses from soft to hard such as tackiness agent, coating, fiber, foam, leatheroid, molding.Phthalate is used in the polyurethane composition as cheap softening agent all the time.
Yet the phthalate of this conduct softening agent use in the past has the suspicion of environmental hormone, and first kind of appointment chemical substance as chemical substance management promotion law (PRTR method) requires it is carried out stringent regulations.
Therefore, people require to develop the cheap and safe softening agent that replaces this phthalate.
For example, as the softening agent of non-phthalate, disclose polyester softening agent (with reference to patent documentation 1).Also disclose the example (with reference to patent documentation 2) that di-acetyl monoacylglycerol ester is used as softening agent.Further disclose polyprotonic acid and have the pure esterification of ehter bond and example (with reference to patent documentation 3) that the compound that obtains uses as softening agent.But all there is the shortcoming of the operability difference after the cooperation in any one in these softening agent.
Patent documentation 1: Japanese kokai publication hei 2-160890 communique
Patent documentation 2: TOHKEMY 2002-129007 communique
Patent documentation 3: TOHKEMY 2002-212534 communique
Summary of the invention
The present invention finishes in view of the above problems, and its purpose is to provide the polyurethane composition and the molding thereof of no environmental hormone suspicion.
In order to achieve the above object, the inventor etc. study intensively repeatedly, found that: if the unsaturated aliphatic hydrocarbon compound that contains at least 1 two key is used as softening agent, then safe, and have and in the past the identical plasticization effect of phthalic ester plasticizer (for example dioctyl phthalate (DOP) (DOP)), thereby finished the present invention.
By the present invention, can provide following polyurethane composition etc.
1, urethanes is characterized by, and contains compound (A) and compound (B), described compound (A) urethane compound that to be the polyvalent alcohol that makes polymeric polyisocyanate and 100 weight parts obtain less than 15 ratio reaction greater than 0.5 in the NCO/OH equivalence ratio; Described compound (B) is that to be selected from carbonatoms be that normal olefine compound, carbonatoms more than 6 is the compound in the epoxy matrix of the oligopolymer of the normal olefine compound more than 6 or the oligopolymer that carbonatoms is the normal olefine compound more than 6, with respect to described polyvalent alcohol 100 weight parts, the use level of described compound (B) for greater than 5 weight parts less than 400 weight parts.
2, as the 1st described polyurethane composition, the carbonatoms of wherein said compound (B) is that the normal olefine compound more than 6 is that carbonatoms is 6～30 alpha-olefin.
3, as the 1st described polyurethane composition, the carbonatoms of wherein said compound (B) is that the normal olefine compound more than 6 is that carbonatoms is 6～18 alpha-olefin.
4, as the 1st described polyurethane composition, the carbonatoms of wherein said compound (B) is that the normal olefine compound more than 6 is that carbonatoms is 6～30 linear internal.
5, as the 1st described polyurethane composition, the carbonatoms of wherein said compound (B) is that the oligopolymer of the normal olefine compound more than 6 is that carbonatoms is dimer～eight aggressiveness of 6～30 normal olefine compound.
6, as the 1st described polyurethane composition, the carbonatoms of wherein said compound (B) is that the epoxy matrix of the oligopolymer of the normal olefine compound more than 6 is that carbonatoms is the dimeric epoxide of 6～30 normal olefine compound.
7, a kind of molding, it claims shape to obtain each the described polyurethane composition in the 1st～6.
By the present invention, can provide the polyurethane composition and the molding thereof of no environmental hormone suspicion.And operability is also excellent after the cooperation of composition of the present invention.
Embodiment
Polyurethane composition of the present invention contains compound (A) and compound (B), wherein, compound (A) urethane compound that to be the polyvalent alcohol that makes polymeric polyisocyanate and 100 weight parts obtain less than 15 ratio reaction greater than 0.5 in the NCO/OH equivalence ratio, compound (B) are that to be selected from carbonatoms be that normal olefine compound, carbonatoms more than 6 is the compound in the epoxy matrix of the oligopolymer of the normal olefine compound more than 6 or the oligopolymer that carbonatoms is the normal olefine compound more than 6.
Urethane compound (A) is the polymkeric substance that obtains by polyvalent alcohol that contains 2 above hydroxyls (OH) and the condensation reaction that contains the polymeric polyisocyanate of 2 above isocyanate group (NCO).
Ratio reaction less than 15 obtains the polyvalent alcohol that urethane compound (A) makes polymeric polyisocyanate and 100 weight parts greater than 0.5 in the NCO/OH equivalence ratio.The NCO/OH equivalence ratio is 0.5 when following, and polyvalent alcohol and polymeric polyisocyanate reactive little can not obtain polyurethane composition.On the other hand, the NCO/OH equivalence ratio is 15 when above, with the intermiscibility variation of compound (B).
In the present invention, composition is solidified and when making the urethane cures thing, urethane compound (A) uses the material that makes with following method, promptly with respect to polyvalent alcohol 100 weight parts, preferably by the NCO/OH equivalence ratio greater than 0.5 smaller or equal to 2.0, more preferably make polymeric polyisocyanate and polyol reaction by 0.9～1.2 and the material that obtains.
On the other hand, composition is solidified and when making urethane prepolymer, urethane compound (A) uses the material that makes with following method, promptly with respect to polyvalent alcohol 100 weight parts, preferably by the NCO/OH equivalence ratio more than or equal to 2.0 less than 15, more preferably by 2.0～10, further preferably make polymeric polyisocyanate and polyol reaction and the material that obtains by 2.0～8.0.
Thus, control the amount of activity (can with the hydroxyl reaction) isocyanate group of polymeric polyisocyanate according to purpose, thereby make urethane compound (A).
Preferably in nitrogen or dry air air-flow, make polyvalent alcohol and polyurethane reaction a few hours in 70～100 ℃.
Also urethane prepolymer can be solidified and make the urethane cures thing.
Polyvalent alcohol is so long as have the compound bearing active hydrogen that contains of 2 above hydroxyls, and just there is no particular limitation.Generally speaking, preferably use polyether glycol or polyester polyol.
More specifically, for example, polyether glycol can be enumerated at least under the condition of a kind of existence of amines such as ternary alcohols, quaternary ammonium, quadrol such as di-alcoholss such as ethylene glycol, propylene glycol, butyleneglycol, glycerine, TriMethylolPropane(TMP) etc., makes ring-opening polymerizations such as propylene oxide and/or oxyethane and random or segmented copolymer of obtaining etc.
Polyester polyol can be enumerated at ethylene glycol, propylene glycol, 1, under the condition that 4-butyleneglycol, neopentyl glycol etc. exist, makes polycondensation such as hexanodioic acid, sebacic acid, terephthalic acid and the multipolymer that obtains etc.
And then polybutadiene polyvalent alcohol, polyisoprene class polyvalent alcohol and their polyolefins polyvalent alcohols such as hydride also are preferred.
Except above-mentioned substance, can also use sugar ester (ラ system エ ス テ Le) in dihydroxyphenyl propane, the Viscotrol C etc. to contain the low molecular activity hydrogen compound of 2 above hydroxyls.It is that hydroxyl in 100～7000,1 molecule is 2～4 a material that such compound can preferably use molecular weight usually.
Just there is no particular limitation as long as polymeric polyisocyanate contains 2 above isocyanate group.
Specifically can enumerate, except aromatic poly-isocyanate classes such as '-diphenylmethane diisocyanate (MDI), tolylene diisocyanate (TDI), naphthalene diisocyanate, also have ester ring type polymeric polyisocyanate classes such as aliphatic polymeric isocyanate class, hydrogenated diphenyl methane diisocyanate, isophorone diisocyanate, norbornene alkyl diisocyanate, hydrogenated tolylene diisocyanate such as hexamethylene diisocyanate (HDI), lysine methyl ester vulcabond.Wherein, preferably use MDI from aspects such as toxicity and prices.
Compound (B) uses and is selected from the unsaturated aliphatic hydrocarbon that contains two keys more than at least 1, particularly, use compound in the epoxy matrix of oligopolymer of the oligopolymer be selected from the normal olefine compound of carbonatoms more than 6, the normal olefine compound of carbonatoms more than 6 or the normal olefine compound of carbonatoms more than 6.In addition, these compounds can use a kind separately, also can use mixing more than 2 kinds.
The normal olefine compound of carbonatoms more than 6, carbonatoms is preferably 6～30, more preferably 6～18 alpha-olefin.For example, can enumerate 1-hexene, 1-octene, 1-decene, 1-laurylene, 1-tetradecylene, 1-hexadecylene, 1-octadecylene etc.
In addition, preferred 6～30, more preferably 18～24 the linear internal of carbonatoms.For example, preferred 2-octadecylene, 3-octadecylene, 4-octadecylene, 5-octadecylene, 2-icosa alkene, 3-icosa alkene, 4-icosa alkene, 5-icosa alkene etc.At this, internal olefin is the olefin(e) compound that contains two keys outside endways.Internal olefin can be by alkene isomerization reaction etc. obtain.
When containing more than 2 the unsaturated aliphatic hydrocarbon compound of two keys, non-conjugated compound is because excellent in stability and preferred.
The oligopolymer of the normal olefine compound of carbonatoms more than 6 is preferably dimer～eight aggressiveness of normal olefine compound.When nine aggressiveness were above, the viscosity height was not suitable as softening agent sometimes.If consider plasticity and evaporation decrement, more preferably dimer～tetramer together.
In this case, the carbonatoms of normal olefine that forms the oligopolymer of normal olefine compound is preferably 6～30, and more preferably 6～18, more preferably 10～15.The preference of oligopolymer can be enumerated 2-butyl-1-octene, 2-hexyl-1-decene, 2-octyl group-1-laurylene, the 2-decyl-1-tetradecane, 2-dodecyl-1-n-Hexadecane, 2-tetradecyl-1-octadecylene, decene tripolymer, the decene tetramer, laurylene tripolymer, the laurylene tetramer, tetradecene tripolymer, the tetradecene tetramer etc.
The oligopolymer of normal olefine compound (dimer～eight aggressiveness) can have the organo-metallic catalyst of acid catalyst or transition metal to make by coordination.
The epoxy matrix of the oligopolymer of the normal olefine compound of carbonatoms more than 6 can be made the oligopolymer epoxidation of the normal olefine of carbonatoms more than 6 by superoxide such as organic peracids such as peracetic acid, perbenzoic acid, benzoyl peroxide, methylethyl ketone peroxide, hydrogen peroxide etc.
In the present invention, above-mentioned epoxy matrix is preferably the dimeric epoxide of the normal olefine compound of carbonatoms 6～30.Specifically can preferably use 2-butyl-2-hexyl oxyethane, 2-hexyl-2-octyl group oxyethane, 2-decyl-2-octyl group oxyethane, 2-decyl-2-dodecyl oxyethane, 2-dodecyl-2-tetradecyl oxirane, 2-hexadecyl-2-tetradecyl oxirane.
Can also use the polyolefin compound of polypropylene oligopolymer, polybutene oligopolymer and so on.
With respect to polyvalent alcohol 100 weight parts, the use level of compound (B) for greater than 5 weight parts less than 400 weight parts, preferred 10～200 weight parts, more preferably 40～150 weight parts.When 5 weight parts are following, the viscosity height of composition, the operability extreme difference that becomes.On the other hand, when 400 weight parts are above, just do not solidify and to form polyurethane composition.
As required, in the scope of not damaging as the rerum natura of purpose, composition of the present invention can add other additives.The object lesson of additive can be enumerated weighting agent, thixotropic agent, curing promotion catalyzer, adherence imparting agent, antioxidant, tinting material etc.
It is the inorganic filler of 1～500 μ m or the surface treated inorganic filler of these materials that weighting agent specifically can be enumerated particle diameters such as clay, talcum, lime carbonate (heavy lightweight), calcium oxide, silica sand, slate flour, mica powder, aluminum oxide, glass powder, zinc oxide, titanium dioxide, carbon black.Wherein, from economy and processing ease consideration, preferably cooperate water-ground limestone.Further preferably the lime carbonate water ratio is adjusted to the water-ground limestone below 0.1%.1 kind of further more preferably this water-ground limestone or the different material of this lime carbonate more than 2 kinds of cooperation particle diameter.
Thixotropic agent specifically can be enumerated organic thixotropic agent of inorganic thixotropic agent such as SiO 2 powder, asbestos powder, organobentonite, polyvinyl chloride powder, modified poly ester polyalcohols etc.Wherein, preferably just can obtain the SiO 2 powder that big thixotropy is given effect on a small quantity.
Solidify promotion and can enumerate dibutyl tin laurate (DBTDL), lead octoate 36 etc. with catalyzer, the adherence imparting agent can be enumerated couplers such as isocynate silane, Racemic glycidol silane etc.
Can also use hydrochloric acid absorbent, heat-resisting stabilizing agent, weather-proof stablizer, photostabilizer, UV light absorber, surface slip agent, anti, antifogging agent, lubricant, antistatic agent, fire retardant, pigment, dyestuff, dispersion agent, anti-copper poisoning agent, neutralizing agent, whipping agent, softening agent, bubble to prevent fluidity amendments such as agent, linking agent, superoxide, welding strength modifying agent, natural oil, synthetic oil, wax etc.
Methods such as composition of the present invention can be with injection molded, extrusion molding, roll forming, application, foaming, lamination, reel off raw silk from cocoons, punching press, casting are shaped as various molding.
Said composition can also be dissolved, is scattered in the mixed solvent of water, organic solvent, water and organic solvent, more than two kinds in the mixed solvent of organic solvent, form emulsion, be coated with spraying, brushing, roller coat etc., use coating, tackiness agent, paint, scratch resistant dose of 1 liquid type or 2 liquid types etc.
[embodiment]
Followingly further describe the present invention according to embodiment.Every evaluation in the table is following to be carried out.
(1) measurement of hardness of urethane cures thing:, measure with A type hardness tester meter according to JIS K7215-1986.
What (2) ooze out has or not: cured article is placed on the filter paper, have or not to adhere on filter paper by range estimation affirmation softening agent and estimate having or not of oozing out.
(3) viscosimetric analysis: 25 ℃ of viscosity that contain the composition of prepolymer with the Type B rotary viscosity design determining.
(4) intermiscibility: the composition that will the contain prepolymer envelope of packing into has in the bottle of nitrogen, confirms the outward appearance after 1 month, the affirmation intermiscibility.At this moment, will confirm that the average evaluation be not separated is zero, with confirm to have the average evaluation that is separated for *.
(5) NCO/OH equivalence ratio: go out by the NCO content of polymeric polyisocyanate and the OH cubage of polyvalent alcohol.
(6) security: because dioctyl phthalate (DOP) (DOP) exists the suspicion of environmental hormone, chloralkane to contain halogen, therefore all be designated as *.
Embodiment 1
To molecular-weight average is 2800, hydroxyl value is that (bright dipping is emerging to produce the aqueous polyhutadiene of the C-terminal of 46.6 (mg-KOH/g), trade(brand)name: after Poly-bd R-45HT) 100 weight parts carry out processed, with aqueous modification MDI (MDI:4,4 '-'-diphenylmethane diisocyanate) (Japanese Polyurethane industry system, trade(brand)name: 12.6 weight parts (NCO/OH equivalence ratio=1.05) Millionate MTL), (bright dipping is emerging to produce as the 1-tetradecylene of softening agent, trade(brand)name: 50 weight parts リ ニ ア レ Application 14), curing catalysts (dibutyl tin laurate (DBTDL)) 0.05 weight part mixes, the preparation composition, pressurizeed 1 hour in 120 ℃ with heated press, solidified 15 hours at 70 ℃ then, obtain the urethane cures thing.
Embodiment 2～6
As softening agent, (bright dipping is emerging to produce to use the 1-hexadecylene respectively in embodiment 2, trade(brand)name: リ ニ ア レ Application 16), (bright dipping is emerging to produce the dimer of use 1-hexene in embodiment 3, trade(brand)name: ア Le キ レ Application 12, purity is more than 95%), (bright dipping is emerging to produce the dimer of use 1-decene in embodiment 4, trade(brand)name: ア Le キ レ Application 20, purity is more than 95%), (bright dipping is emerging to produce the tripolymer of use 1-decene in embodiment 5, trade(brand)name: ア Le キ レ Application 30, the hydrocarbon content of carbonatoms 30 is more than the 90wt%), (bright dipping is emerging to produce the tetramer of use 1-decene in embodiment 6, trade(brand)name: ア Le キ レ Application 40, the hydrocarbon content of carbonatoms 40 is more than the 90wt%), in addition, experimentize in the same manner, obtain cured article with embodiment 1.
Comparative example 1
Except not adding the softening agent, experimentize in the same manner with embodiment 1, obtain cured article.
Comparative example 2
Except using outside the dioctyl phthalate (DOP) (DOP) (Hiroshima and light (strain) system, special grade chemical), experimentize in the same manner with embodiment 1, obtain cured article.
Comparative example 3
Except using outside the chloralkane (eastern Cao's system, trade(brand)name Toyoparax145), experimentize in the same manner with embodiment 1, obtain cured article.
Comparative example 4
Except the amount with aqueous modification MDI is made as 6.0 weight parts (NCO/OH equivalence ratio=0.5), experimentize in the same manner with embodiment 1.In this comparative example, fail to obtain cured article.
Comparative example 5
Except the amount with softening agent is made as 400 weight parts, experimentize in the same manner with embodiment 1.In this comparative example, fail to obtain cured article.
Embodiment 7
To molecular weight is 3,000 polypropylene glycol (rising sun electrification system, trade(brand)name: after ADK PolyetherG-3000) 100 weight parts carry out processed, the aqueous modification MDI of 15.5 weight parts (NCO/OH equivalence ratio=1.05), 50 weight parts are mixed as リ ニ ア レ Application 14, the 0.05 weight part curing catalysts (DBTDL) of softening agent, the preparation composition, solidified 24 hours at 70 ℃, obtain the urethane cures thing.
Embodiment 8～12
As softening agent, in embodiment 8, use リ ニ ア レ Application 16 respectively, in embodiment 9, use リ ニ ア レ Application 12, in embodiment 10, use ア Le キ レ Application 20, in embodiment 11, use ア Le キ レ Application 30, in embodiment 12, use ア Le キ レ Application 40, in addition, experimentize in the same manner with embodiment 7, obtain cured article.
Comparative example 6
Except not adding the softening agent, experimentize in the same manner with embodiment 7, obtain cured article.
Comparative example 7
Except using outside the dioctyl phthalate (DOP) (DOP) (Hiroshima and light (strain) system, special grade chemical), experimentize in the same manner with embodiment 1, obtain cured article.
Comparative example 8
Except using chloralkane (eastern Cao's system, trade(brand)name: ト ヨ パ ラ Star Network ス 145), experimentize in the same manner, obtain cured article with embodiment 1 as outside the softening agent.
The evaluation result of embodiment 1～12, comparative example 1～8 is shown in table 1 and the table 2.
In addition, the ratio of softening agent is a ratio with respect to polyvalent alcohol 100 weight parts in the table.
Table 1
| Embodiment | Comparative example | |||||||||||
| 1 | 2 | 3 | 4 | 5 | 6 | 1 | 2 | 3 | 4 | 5 | ||
| Polyvalent alcohol | R- 45HT | R- 45HT | R- 45HT | R- 45HT | R- 45HT | R- 45HT | R- 45HT | R- 45HT | R- 45HT | R- 45HT | R- 45HT | |
| Polymeric polyisocyanate | Modification MDI | Modification MDI | Modification MDI | Modification MDI | Modification MDI | Modification MDI | Modification MDI | Modification MDI | Modification MDI | Modification MDI | Modification MDI | |
| NCO/OH | 1.05 | 1.05 | 1.05 | 1.05 | 1.05 | 1.05 | 1.05 | 1.5 | 1.05 | 0.5 | 1.05 | |
| Softening agent | Kind | リニア レン 14 | リニア レン 16 | アルキ レン 12 | アルキ レン 20 | アルキ レン 30 | アルキ レン 40 | Do not have | DOP | Chloralkane | リニ アレ ン14 | リニ アレ ン14 |
| Cooperation ratio (weight part) | 50 | 50 | 50 | 50 | 50 | 50 | 0 | 50 | 50 | 50 | 400 | |
| Hardness | 40 | 32 | 43 | 28 | 25 | 24 | 52 | 33 | 35 | - | - | |
| Ooze out | 24 hours | Do not have | Do not have | Do not have | Do not have | Do not have | Do not have | Do not have | Do not have | Do not have | - | - |
| 1 week | Do not have | Do not have | Do not have | Do not have | Do not have | Do not have | Do not have | Do not have | Do not have | - | - | |
| 4 weeks | Do not have | Do not have | Do not have | Do not have | Do not have | Do not have | Do not have | Do not have | Do not have | - | - | |
| Security | ○ | ○ | ○ | ○ | ○ | ○ | ○ | × | × | ○ | ○ | |
Table 2
| Embodiment | Comparative example | |||||||||
| 7 | 8 | 9 | 10 | 11 | 12 | 6 | 7 | 8 | ||
| Polyvalent alcohol | G-3000 | G-3000 | G-3000 | G-3000 | G-3000 | G-3000 | G-3000 | G-3000 | G-3000 | |
| Polymeric polyisocyanate | Modification MDI | Modification MDI | Modification MDI | Modification MDI | Modification MDI | Modification MDI | Modification MDI | Modification MDI | Modification MDI | |
| NCO/OH | 1.05 | 1.05 | 1.05 | 1.05 | 1.05 | 1.05 | 1.05 | 1.05 | 1.05 | |
| Softening agent | Kind | リニア レン14 | リニア レン16 | アルキ レン12 | アルキ レン20 | アルキ レン30 | アルキ レン40 | Do not have | DOP | Chloralkane |
| Cooperation ratio (weight part) | 50 | 50 | 50 | 50 | 50 | 50 | 0 | 50 | 50 | |
| Hardness | 25 | 21 | 26 | 22 | 20 | 19 | 35 | 22 | 24 | |
| Ooze out | 24 hours | Do not have | Do not have | Do not have | Do not have | Do not have | Do not have | Do not have | Do not have | Do not have |
| 1 week | Do not have | Do not have | Do not have | Do not have | Do not have | Do not have | Do not have | Do not have | Do not have | |
| 4 weeks | Do not have | Do not have | Do not have | Do not have | Do not have | Do not have | Do not have | Do not have | Do not have | |
| Security | ○ | ○ | ○ | ○ | ○ | ○ | ○ | × | × | |
Embodiment 13～18
In embodiment 1, use 24 weight parts (NCO/OH equivalence ratio=2.5) 4,4 '-'-diphenylmethane diisocyanate (MDI) replaces aqueous modification MDI, adds softening agent 100 weight parts, the catalyzer shown in the table 3, in nitrogen gas stream in 70 ℃ make its reaction 5 hours, obtain urethane prepolymer.
Embodiment 19～24
To molecular weight is 3,000 polypropylene glycol (rising sun electrification system, ADK Polyether P-3000) after 100 weight parts carries out processed, add the MDI (NCO/OH equivalence ratio=2.5) of 20 weight parts, softening agent 100 weight parts, the catalyzer shown in the table 3, in nitrogen gas stream in 70 ℃ make its reaction 5 hours, obtain urethane prepolymer.
Comparative example 9
Except not adding the softening agent, experimentize in the same manner with embodiment 13, obtain urethane prepolymer.
Comparative example 10
Except using 145 weight parts (NCO/OH equivalence ratio=15) MDI, experimentize in the same manner with embodiment 13, obtain urethane prepolymer.This prepolymer poor with the intermiscibility of リ ニ ア レ Application 14 (リ ニ ア レ Application 14 separates with urethane prepolymer) therefore can not be measured viscosity.
Comparative example 11
Except the amount with softening agent is made as 5 weight parts, experimentize in the same manner with embodiment 13, obtain urethane polymers.This prepolymer demonstrates the high viscosity that can not measure its viscosity with rotational viscosimeter.
Comparative example 12
Except not adding the softening agent, experimentize in the same manner with embodiment 19, obtain urethane prepolymer.
The evaluation result of embodiment 13～24, comparative example 9～12 is shown in table 3 and the table 4.
Table 3
| Embodiment | Comparative example | |||||||||
| 13 | 14 | 15 | 16 | 17 | 18 | 9 | 10 | 11 | ||
| Polyvalent alcohol | R-45HT | R-45HT | R-45HT | R-45HT | R-45HT | R-45HT | R-45HT | R-45HT | R-45HT | |
| Polymeric polyisocyanate | MDI | MDI | MDI | MDI | MDI | MDI | MDI | MDI | MDI | |
| NCO/OH | 2.5 | 2.5 | 2.5 | 2.5 | 2.5 | 2.5 | 2.5 | 15 | 2.5 | |
| Softening agent | Kind | リニア レン14 | リニア レン16 | アルキ レン12 | アルキ レン20 | アルキ レン30 | アルキ レン40 | Do not have | リニア レン14 | リニア レン14 |
| Cooperation ratio (polymerization amount) | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 5 | |
| Viscosity (Pas) | 80 | 65 | 85 | 60 | 64 | 72 | 200 | Can't measure | Can't measure | |
| Intermiscibility | ○ | ○ | ○ | ○ | ○ | ○ | - | × | - | |
Table 4
| Embodiment | Comparative example | |||||||
| 19 | 20 | 21 | 22 | 23 | 24 | 12 | ||
| Polyvalent alcohol | P-3000 | P-3000 | P-3000 | P-3000 | P-3000 | P-3000 | P-3000 | |
| Polymeric polyisocyanate | MDI | MDI | MDI | MDI | MDI | MDI | MDI | |
| NCO/OH | 2.5 | 2.5 | 2.5 | 2.5 | 2.5 | 2.5 | 2.5 | |
| Softening agent | Kind | リニアレ ン14 | リニアレ ン16 | アルキレ ン12 | アルキレ ン20 | アルキレ ン30 | アルキレ ン40 | Do not have |
| Cooperation ratio (polymerization amount) | 100 | 100 | 100 | 100 | 100 | 100 | 100 | |
| Viscosity (Pas) | 40 | 33 | 42 | 27 | 31 | 36 | 90 | |
| Intermiscibility | ○ | ○ | ○ | ○ | ○ | ○ | - | |
Embodiment 25
Except using the dimeric epoxide of 1-decene (2-decyl-2-octyl group oxyethane, bright dipping is emerging to produce, ア Le キ レ Application 20 epoxide), to experimentize in the same manner, obtain cured article with embodiment 1 as outside the softening agent.Composition and evaluation result are shown in Table 5.The ratio of softening agent is the ratio with respect to polyvalent alcohol 100 weight parts in the table.
Table 5
| Embodiment 25 | ||
| Polyvalent alcohol | R-45HT | |
| Polymeric polyisocyanate | Modification MDI | |
| Softening agent | Kind | ア Le キ レ Application 20 epoxide |
| Cooperation ratio (weight part) | 50 | |
| Hardness | 29 | |
| Ooze out | 24 hours | Do not have |
| 1 week | Do not have | |
| 4 weeks | Do not have | |
| Security | ○ | |
Embodiment 26
In the urethane prepolymer (コ ロ ネ one ト 4076, Japanese Polyurethane system) of 100 weight parts, add the ア Le キ レ Application 20 of 100 weight parts as softening agent.Estimate the viscosity (mensuration temperature: 75 ℃) and the intermiscibility of this composition.The composition and the evaluation result of composition are shown in Table 6.
Softening agent ratio in the table is the ratio with respect to 100 weight part polyvalent alcohols.
Table 6
| Embodiment | Comparative example | |||||||||
| 26 | 27 | 28 | 29 | 30 | 31 | 13 | 14 | 151 | ||
| The kind of prepolymer | コ ロ ネ one ト 4076 | コ ロ ネ one ト 4076 | コ ロ ネ one ト 4090 | コ ロ ネ one ト 4090 | コ ロ ネ one ト 4191 | コ ロ ネ one ト 4191 | コ ロ ネ one ト 4076 | コ ロ ネ one ト 4090 | コ ロ ネ one ト 4191 | |
| Softening agent | Kind | アルキ レン20 | ア Le キ レ Application 20 epoxide | アルキ レン20 | ア Le キ レ Application 20 epoxide | アルキ レン20 | ア Le キ レ Application 20 epoxide | - | - | - |
| Cooperation ratio (polymerization amount) | 100 | 100 | 100 | 100 | 100 | 100 | - | - | - | |
| Viscosity (Pas) | 1000 | 1100 | 490 | 500 | 200 | 210 | 300 | 1100 | 600 | |
| Intermiscibility | ○ | ○ | ○ | ○ | ○ | ○ | - | - | - | |
Embodiment 27～31
Except being made as the prescription shown in the table 6, experimentize in the same manner with embodiment 26.Evaluation result is as shown in table 6.
コ ロ ネ one ト 4090,4191 (trade(brand)name) is the urethane prepolymer of Japanese Polyurethane system.
Comparative example 13～15
Urethane prepolymer used in embodiment 26,28 and 30 is measured kinetic viscosity.The results are shown in the table 6.
Industrial applicability
Polyurethane composition of the present invention, can be preferred for the purposes field of non-foaming polyurethane resin, for example tackiness agent, coating, water-resisting agent, permeability-reducing admixture, lagging material, cold insulation material, cosmetics material, sealing material, magnetic conduct adhesive, cushioning material, leatheroid, foam, fiber etc.Particularly preferred purposes is tackiness agent, coating, water-resisting agent, permeability-reducing admixture.
Claims (7)
1. polyurethane composition, said composition contains compound (A) and compound (B), described compound (A) urethane compound that to be the polyvalent alcohol that makes polymeric polyisocyanate and 100 weight parts obtain less than 15 ratio reaction greater than 0.5 in the NCO/OH equivalence ratio; Described compound (B) is that to be selected from carbonatoms be that normal olefine compound, carbonatoms more than 6 is the compound in the epoxy matrix of the oligopolymer of the normal olefine compound more than 6 or the oligopolymer that carbonatoms is the normal olefine compound more than 6, with respect to described polyvalent alcohol 100 weight parts, the use level of described compound (B) for greater than 5 weight parts less than 400 weight parts.
2. polyurethane composition as claimed in claim 1, the carbonatoms of wherein said compound (B) are that the normal olefine compound more than 6 is that carbonatoms is 6～30 alpha-olefin.
3. polyurethane composition as claimed in claim 1, the carbonatoms of wherein said compound (B) are that the normal olefine compound more than 6 is that carbonatoms is 6～18 alpha-olefin.
4. polyurethane composition as claimed in claim 1, the carbonatoms of wherein said compound (B) are that the normal olefine compound more than 6 is that carbonatoms is 6～30 linear internal.
5. polyurethane composition as claimed in claim 1, the carbonatoms of wherein said compound (B) are that the oligopolymer of the normal olefine compound more than 6 is that carbonatoms is dimer～eight aggressiveness of 6～30 normal olefine compound.
6. polyurethane composition as claimed in claim 1, the carbonatoms of wherein said compound (B) are that the epoxy matrix of the oligopolymer of the normal olefine compound more than 6 is that carbonatoms is the dimeric epoxide of 6～30 normal olefine compound.
7. molding, it is shaped each the described polyurethane composition in the claim 1～6 and obtains.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2004043973 | 2004-02-20 | ||
| JP043973/2004 | 2004-02-20 | ||
| JP181161/2004 | 2004-06-18 |
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|---|---|---|---|
| CNA200810168862XA Division CN101397403A (en) | 2004-02-20 | 2005-02-09 | Polyurethane composition and molded article thereof |
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| Publication Number | Publication Date |
|---|---|
| CN1922274A true CN1922274A (en) | 2007-02-28 |
| CN100487052C CN100487052C (en) | 2009-05-13 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2005800055728A Expired - Fee Related CN100487052C (en) | 2004-02-20 | 2005-02-09 | Polyurethane composition and molded article thereof |
| CNA200810168862XA Pending CN101397403A (en) | 2004-02-20 | 2005-02-09 | Polyurethane composition and molded article thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA200810168862XA Pending CN101397403A (en) | 2004-02-20 | 2005-02-09 | Polyurethane composition and molded article thereof |
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| Country | Link |
|---|---|
| CN (2) | CN100487052C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102844479A (en) * | 2009-10-26 | 2012-12-26 | 英威达技术有限公司 | Polyurethane elastic yarn and production method thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105970343A (en) * | 2016-06-17 | 2016-09-28 | 浙江华峰氨纶股份有限公司 | Preparation method of low-modulus elastic polyurethane fibers with high recovery ratio |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3943090A1 (en) * | 1989-12-27 | 1991-07-04 | Henkel Kgaa | MOISTURIZING POLYURETHANEAS MASSES WITH IMPROVED PROPERTIES |
| JP3573983B2 (en) * | 1998-11-26 | 2004-10-06 | サンスター技研株式会社 | Two-part sealant composition |
-
2005
- 2005-02-09 CN CNB2005800055728A patent/CN100487052C/en not_active Expired - Fee Related
- 2005-02-09 CN CNA200810168862XA patent/CN101397403A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102844479A (en) * | 2009-10-26 | 2012-12-26 | 英威达技术有限公司 | Polyurethane elastic yarn and production method thereof |
| CN102844479B (en) * | 2009-10-26 | 2014-11-05 | 英威达技术有限公司 | Polyurethane elastic yarn and production method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN100487052C (en) | 2009-05-13 |
| CN101397403A (en) | 2009-04-01 |
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