JPS6346766B2 - - Google Patents
Info
- Publication number
- JPS6346766B2 JPS6346766B2 JP58162338A JP16233883A JPS6346766B2 JP S6346766 B2 JPS6346766 B2 JP S6346766B2 JP 58162338 A JP58162338 A JP 58162338A JP 16233883 A JP16233883 A JP 16233883A JP S6346766 B2 JPS6346766 B2 JP S6346766B2
- Authority
- JP
- Japan
- Prior art keywords
- polyol
- polyurethane
- component
- aromatic
- weight
- 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.)
- Expired
Links
- 229920005862 polyol Polymers 0.000 claims description 78
- 150000003077 polyols Chemical class 0.000 claims description 71
- 229920002635 polyurethane Polymers 0.000 claims description 46
- 239000004814 polyurethane Substances 0.000 claims description 43
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 229920001228 polyisocyanate Polymers 0.000 claims description 20
- 239000005056 polyisocyanate Substances 0.000 claims description 20
- 125000001931 aliphatic group Chemical group 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 13
- 150000004982 aromatic amines Chemical class 0.000 claims description 12
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 238000005299 abrasion Methods 0.000 claims description 7
- 239000010692 aromatic oil Substances 0.000 claims description 6
- 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 30
- -1 aromatic polyol Chemical class 0.000 description 20
- 239000000047 product Substances 0.000 description 17
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- 239000003921 oil Substances 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 10
- 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 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-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
- 125000002947 alkylene group Chemical group 0.000 description 4
- 238000005452 bending Methods 0.000 description 4
- 230000001588 bifunctional effect Effects 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 239000010734 process oil Substances 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000011256 inorganic filler Substances 0.000 description 3
- 229910003475 inorganic filler Inorganic materials 0.000 description 3
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- 239000004604 Blowing Agent Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229930006000 Sucrose Natural products 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000010687 lubricating oil Substances 0.000 description 2
- 239000010721 machine oil Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 2
- 229910052982 molybdenum disulfide Inorganic materials 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- ICLCCFKUSALICQ-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanato-3-methylphenyl)-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(C=2C=C(C)C(N=C=O)=CC=2)=C1 ICLCCFKUSALICQ-UHFFFAOYSA-N 0.000 description 1
- MQXNNWDXHFBFEB-UHFFFAOYSA-N 2,2-bis(2-hydroxyphenyl)propane Chemical group C=1C=CC=C(O)C=1C(C)(C)C1=CC=CC=C1O MQXNNWDXHFBFEB-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- MIUUNYUUEFHIHM-UHFFFAOYSA-N Bisphenol A bis(2-hydroxypropyl) ether Chemical compound C1=CC(OCC(O)C)=CC=C1C(C)(C)C1=CC=C(OCC(C)O)C=C1 MIUUNYUUEFHIHM-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-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
- 230000009471 action Effects 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- AFYPFACVUDMOHA-UHFFFAOYSA-N chlorotrifluoromethane Chemical compound FC(F)(F)Cl AFYPFACVUDMOHA-UHFFFAOYSA-N 0.000 description 1
- PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000012208 gear oil Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000012774 insulation material Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- 239000010723 turbine oil Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
Description
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ãããDETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel polyurethane composition, and particularly to a hard polyurethane composition having a high heat distortion temperature and excellent friction and abrasion resistance.
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ãŠæ±çšãããŠããã Rigid polyurethane is broadly classified into non-foamed molded products and foamed molded products, and foamed molded products are further classified into high-foamed molded products and low-foamed molded products depending on the foaming rate. Non-foamed molded products and low-foamed molded products are used as engineering resins in various equipment parts and automobile parts, while highly foamed molded products are used mainly as insulation materials, making them a versatile resin that is useful for an extremely wide range of applications. has been done.
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ããŠããã Conventional rigid polyurethanes contain one or more polyfunctional aliphatic or aromatic polyol monomers, polyoxyalkylene polyols, especially polyoxypropylene polyols, or polyfunctional aliphatic or aromatic polyester polyols. A polyol component consisting of a mixture, an aliphatic or aromatic polyisocyanate or a type of polyisocyanate,
or a polyisocyanate component consisting of a mixture thereof in the presence of a catalyst, a blowing agent, etc.
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èããªããšããæ¬ ç¹ãçããã However, these polyurethane molded products generally have poor heat resistance, and when heat distortion temperature (measured according to ASTM D-648) is used as a measure to evaluate heat resistance, conventional polyurethane molded products have a heat distortion temperature of 80 to 100 at most. â was the limit, and it was difficult to exceed 100â with practical strength. On the other hand, heat resistance can be improved by introducing isocyanate groups obtained by trimerizing isocyanates;
At the same time, the resulting molded product becomes extremely brittle and cannot be put to practical use.
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è² ã®å¹æãããªãã€ãã Also, as an engineering resin, P (load
The PV value, which is the product of Kg/cm 2 ) and V (velocity m/min), is
It is said that a value of 800 or more is preferable for a sliding member. However, the current rigid polyurethane made of polyol and polyisocyanate has a PV value of 400 or less, and has the disadvantage that it can only be used under conditions of low speed and low load. Generally, molybdenum disulfide and graphite are used to improve friction and wear resistance, but these compounds have no significant effect on hard polyurethane, but rather improve heat distortion temperature, tensile strength, and bending strength. and reduce impact resistance. In order to improve friction and abrasion resistance, we tried adding various silicone resins, fluorine oligomers, titanium coupling agents, silane coupling agents, encapsulated oil, etc., but none of them had foam-containing, impact resistance, It was found that properties such as tensile strength and bending strength deteriorated. Furthermore, fiber reinforcement had only a negative effect.
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ãšã«ããã The object of the present invention is to have high thermal stability and
Our objective is to provide polyurethane with excellent friction and abrasion resistance, and in particular, to provide a new polyurethane that has a high heat distortion temperature of at least 100°C, which could not be achieved with conventional hard polyurethane, and has practical strength, especially impact resistance. An object of the present invention is to provide a rigid polyurethane composition.
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ãšã«ããã Furthermore, the object of the present invention is to provide a friction-resistant material that can be used at low speeds and high loads, high speeds and low loads, and high speeds and high loads.
An object of the present invention is to provide a hard, wear-resistant polyurethane composition.
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èæ©èæ§ç¡¬è³ªããªãŠã¬ã¿ã³çµæç©ã«ä¿ãã The present invention is a polyurethane composition obtained by the reaction of a polyol component having at least difunctional hydroxyl groups and an at least difunctional polyisocyanate component, wherein the polyol component includes 2,
A mixed polyol consisting of 40 to 80 parts by weight of a propylene oxide adduct of 2-bis(4-hydroxyphenyl)propane and 20 to 60 parts by weight of an aromatic amine-based polyoxyalkylene polyol having a hydroxyl value of 200 to 700 is used. , a friction resistant product characterized by adding an aliphatic or aromatic oil component to the polyol component and/or polyisocyanate component;
It relates to a wear-resistant hard polyurethane composition.
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ããã®ä»è¢«èŠç©çãšããŠæçšã§ããã The hard polyurethane of the present invention can be used in various fields, but is particularly useful as various industrial parts that require heat resistance, friction resistance, and wear resistance, such as sliding material parts and other coatings.
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ãªãŠã¬ã¿ã³ãåŸãããšã«æåãããã®ã§ããã In the present invention, 2,2-bis(4-hydroxyphenyl)propane (2,2-bis{4-(2-hydroxypropoxy)phenyl}propane) having the following structure as one component of the polyol component is used in the present invention. (hereinafter referred to as bisphenol A)
By using a propylene oxide (hereinafter referred to as PO) adduct, we succeeded in obtaining a rigid polyurethane with excellent heat resistance.
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èšãïŒã«ãããŠãé«ããšããç¹åŸŽãçºæ®ããã That is, in the present invention, since the PO adduct of bisphenol A was used as one component of the polyol component, the polyurethane obtained by reacting with polyisocyanate has a high concentration of aromatic rings in the molecular chain and has a rigid molecular structure, so it has a high glass content. Has a transition point. Therefore, it exhibits excellent thermal stability and a high heat distortion temperature (hereinafter referred to as HDT).
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以äžã§ãªããã°ãªããªãã The bisphenol A-PO adduct of the present invention can be obtained by reacting 1 mole of bisphenol A with 2 or more moles of PO using a known method. That is, the above adduct is bisphenol A
2,2-bis{4-(2-
Hydroxypropoxy) phenyl}propane 1
Contained as an ingredient, its content is usually about 40% by weight
The content is preferably about 80% by weight or more. As another component, an adduct containing 3 moles or more of PO per mole of bisphenol A may be contained, usually at most about 60% by weight, preferably at most about 20% by weight. In addition, other components include bisphenol A and PO, which have one or two primary terminal hydroxyl groups.
The adduct of 2 or 3 moles or more is produced as a by-product during the addition reaction, and can be contained in the polyol component in any proportion. However, the amount of unreacted phenolic hydroxyl groups, such as bisphenol A and adducts of 1 mole of PO of bisphenol A, must be 1% by weight or less.
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ã®ã§åŸãããããªãŠã¬ã¿ã³ã®èç±æ§ã¯äœäžããã If the adduct containing 2 moles of PO to 1 mole of bisphenol A is less than 40% by weight, the concentration of the skeleton of bisphenol A as a polyol component decreases, resulting in a decrease in the heat resistance of the resulting polyurethane.
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ãªãªãŒã«ã¯20ã60éééšãæãŸããã Furthermore, in the present invention, at least a bifunctional hydroxyl group with a hydroxyl value of 200 to 200 is added to the polyol as a polyol component.
700, preferably 300 to 500, is used in combination with an aromatic amine-based polyoxyalkylene polyol. Furthermore, the average hydroxyl value of the above mixed polyol component is
200 to 700, preferably 300 to 500, the impact strength of the polyurethane obtained was surprisingly contrary to expectations, and it was found that a synergistic effect of increasing impact strength was obtained without almost reducing the high HDT. Ivy. That is, the impact strength of the polyurethane using the above two types of polyol components in combination is superior to the impact strength of each polyurethane when the above two types of polyol components are used alone. The reason for this has not yet been fully elucidated, but considering that with conventional hard polyurethanes, impact strength tends to decrease when HDT is increased, and it is extremely difficult to increase both HDT and impact strength. ,
The above effects of the present invention are surprising. In view of moldability and physical properties, the polyol component consisting of the bisphenol A-PO adduct is preferably 40 to 80 parts by weight, and the aromatic amine-based polyoxyalkyl polyol is preferably 20 to 60 parts by weight.
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床ãé«ããªãããšãªã©ãæããããã It has also been found that in the present invention, by using the PO adduct of bisphenol A in combination with an aromatic amine-based polyol, not only high HDT and impact strength can be obtained, but also processability, moldability, etc. can be effectively improved. Ivy. The improvement in processability referred to here refers to the reduction in the viscosity of the polyol liquid due to the introduction of the aromatic amine-based polyol, and the improvement in so-called compatibility in which the polyol liquid and the polyisocyanate liquid mix well even at room temperature. Further, since the chemical reaction proceeds due to the moderate autocatalytic action of the aromatic tertiary amine, no catalyst is intentionally required. Therefore, there is no need to add a catalyst to the polyol liquid.
One example is that the polyol liquid has excellent storage stability. Furthermore, improvement in moldability includes increasing the strength of the polyurethane molded product upon demolding due to the introduction of a primary network using at least a bifunctional aromatic amine-based polyol.
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ãŠããªãããªãªãŒã«ã§ããã At least the above bifunctional hydroxyl value 200 to 700,
Preferably 300 to 500 aromatic amine-based polyoxyalkylene polyols are prepared by known methods such as aromatic monoamines such as aniline or 2,4- and 2,6-tolylene diamines (TDA) and so-called crude TDA, 4,4 '-diaminodiphenylmethane and one type of aromatic diamine and aromatic polyamine such as polymethylene polyphenylene polyamine obtained by condensation of aniline and formalin, ortho-, meta- or para-phenylene diamine, meta- or para-xylylene diamine, or Moreover, it is a polyol obtained by adding one or more alkylene oxides such as propylene oxide and ethylene oxide, and substantially no free primary or secondary amine remains.
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ã®ã奜ãŸããã The above-mentioned aromatic amine-based polyols are synthesized at the stage of synthesis to reduce viscosity and improve processability
In addition to aromatic amines, the following aliphatic glycols and the like can be used as co-initiators. For example, polyfunctional aliphatic glycols such as ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, glycerin, trimethylolpropane, glucose, sorbitol, sucrose; aliphatic amines and aliphatic glycols such as ethanolamine, diethanolamine, triethanolamine, ethylenediamine; Examples include alkanolamines, and these co-initiators are preferably used in an equimolar or less amount relative to the aromatic amine.
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ã¯æ¬¡ã®ãããªããªãªãŒã«ãæããããšãã§ããã The present invention uses a PO adduct of bisphenol A and an aromatic amine-based polyol as polyol components,
It is characterized by the fact that the polyurethane obtained by reaction with polyisocyanate has a high HDT.
In addition, although it has excellent processability and moldability, in addition to these polyol components, at least another difunctional polyol with a hydroxyl value of 50 to 1830 must be used in an amount not exceeding 40% by weight based on the total polyol component. processability, such as reducing the viscosity of the polyol component,
It has the effect of improving moldability. Specific examples of the at least difunctional polyol having a hydroxyl value of 50 to 1830 include the following polyols.
(a) å°ãªããšãïŒå®èœæ§ã®æ°Žé
žåºãæããæ°Žé
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䟡50ã850ã®è³éŠæããªãªãŒã«ã(a) An aromatic polyol having a hydroxyl value of 50 to 850 and having at least difunctional hydroxyl groups.
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ããã(a)ã®è³éŠæããªãªãŒã«ã䜵çšããå Ž
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ã®ã奜ãŸããã (a) Hydroquinone, pyrogallol, 4,4'-
Polyol with a hydroxyl value of 250 to 600 obtained by adding an alkylene oxide such as propylene oxide or ethylene oxide to a monocyclic or polycyclic aromatic compound having at least two hydroxyl groups such as isopropylidene diphenol (b) Phthalic acid, isophthalic acid acid, terephthalic acid,
Polyols with a hydroxyl value of 300 to 500 obtained by adding alkylene oxides such as propylene oxide and ethylene oxide to aromatic polybasic acids such as trimellitic acid (c) Metaxylylene glycol, paraxylylene glycol (d) Phthalic acid, isophthalic acid Acid, aromatic dicarboxylic acid such as terephthalic acid, its anhydride or its lower alcohol ester, and/or aliphatic dicarboxylic acid such as adipic acid, succinic acid, etc., and contains ethylene glycol, 1,4-butylene glycol, Aliphatic polyols such as methylolpropane, 1,4-cyclohexanediol, 1,
4-Cyclohexane dimethanol, β, β,
β',β'-tetramethyl-2,4,8,10-tetraoxaspiro(5,5)-undecane-
A polyester polyol with a hydroxyl value of 50 to 450 whose polyol component is an alicyclic polyol such as 3,9-diethanol or the polyols listed in (a), (b), and (c) above. These aromatic polyols in (a) are used in combination. In this case, it is preferable that the amount does not exceed 50% by weight based on the total polyol, and that the average hydroxyl value is 200 to 500.
(b) æ°Žé
žåºäŸ¡800ã1830ã®å€å®èœèèªæã°ãªã³ãŒ
ã«ã(b) Polyfunctional aliphatic glycol with a hydroxyl value of 800 to 1830.
äŸãã°ãšãã¬ã³ã°ãªã³ãŒã«ããžãšãã¬ã³ã°ãª
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以äžã®ç¯å²ã§äœµçšã§ããã Examples include ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, glycerin, and triethanolamine, which can be used in combination in an amount of 10% by weight or less based on the total polyol.
(c) æ°Žé
žåºäŸ¡300ã800ã®å€å®èœèèªæããªãªãŒ
ã«ã(c) A polyfunctional aliphatic polyol with a hydroxyl value of 300 to 800.
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以äžã®ç¯å²ã§äœµçšããã®ã奜ãŸããã For example, a polyol in which one or more alkylene oxides such as propylene oxide and ethylene oxide are added to one or more of sucrose, sorbitol, glucose, pentaerythritol, trimethylolpropane, glycerin, ethylenediamine, diethanolamine, water, etc. , is preferably used in combination in an amount of 40% by weight or less based on the total polyol.
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ãã The polyols listed above are particularly preferred, and other polyols with at least bifunctional hydroxyl value of 50 to 1830 are used based on all polyols.
They can be used in combination within a range not exceeding 40% by weight.
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ãã Prior to the reaction with isocyanates, these polyols have a moisture content of 0.05% or less, preferably
It is necessary to keep it below 0.02%. Also, the polyisocyanates should be sufficiently degassed in advance. If these are neglected, unnecessary foaming will occur during the curing reaction. However, this is of course not the case when obtaining a foam.
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ã奜é©ã«äœ¿çšãããã As the polyisocyanate component of the present invention, various at least difunctional aliphatic, alicyclic, and aromatic polyisocyanates known in the field of polyurethane production can be used, but aromatic polyisocyanates are particularly preferably used. . For example, 4,4'-diphenylmethane diisocyanate (MDI) and carbodiimide-modified MDI (e.g. Nippon Polyurethane Co., Ltd. MTL), polymethylene polyphenyl isocyanate (PAPI), polymeric polyisocyanate (e.g. Sumitomo Bayer Urethane)
44V), 2,4- and 2,6-tolylene diisocyanate (TDI), orthotoluidine diisocyanate (TODI), naphthylene diisocyanate (NDI), xylylene diisocyanate (XDI), and the like are preferably used.
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ã·ã¢ããŒãã€ã³ããã¯ã¹ã¯100ã115ãæãŸããã The polyol component and the polyisocyanate component can be reacted by a one-shot method or a prepolymer method. The reaction between polyol and polyisocyanate is known as isocyanate index.
Preferably, the range is from 100 to 180, particularly preferably from 105 to 160. Outside this range, heat resistance decreases regardless of whether the isocyanate index becomes smaller or larger. Although the cause of this is not clear, it is presumed that it is due to a decrease in the substantial molecular weight of the polymer. In order to lower the coefficient of friction, the isocyanate index is preferably 100 to 115.
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ãããšãã§ããã In the present invention, an aliphatic or aromatic oil component is added to the polyol component and/or polyisocyanate component in order to improve the friction and abrasion resistance of the hard polyurethane obtained above. Aliphatic oils also include alicyclic oils. The above-mentioned aliphatic oil is preferably a lubricating oil specified by JIS, and specific examples thereof include turbine oil, gear oil, machine oil, bearing oil, refrigerating machine oil, and lubricating oil for internal combustion engines. Further, as the aromatic oil, for example, petroleum-based softeners called extender oils or process oils are used, and various softeners such as paraffin-based process oils, naphthenic process oils, aromatic process oils, etc. can be used. Can be done.
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çãèæ©æŠãèæ©èæ§ãåäžãããã In the present invention, the above aliphatic oils or aromatic oils are used alone or as a mixture, and their ISOVG
[Viscosity grade, cSt (mm 2 /s), 40â] is 68 to 1000
is preferable, and 100 to 680 is particularly preferable. In this range, a migration phenomenon occurs in which the oil oozes onto the surface of the polyurethane, and this migration phenomenon produces a grease effect and improves the friction and wear resistance.
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ãèæ©æŠãèæ©èæ§ãä»äžããããšãã§ããã In the present invention, the amount of the oil component added is preferably 1 to 15 parts by weight per 100 parts by weight of polyurethane.
Particularly preferred is 2 to 10 parts by weight. Within this range, friction resistance and abrasion resistance can be improved without reducing the tensile strength, bending strength, impact strength, etc. of the polyurethane obtained. By adding the oil component in this manner, the hard polyurethane of the present invention can be given superior friction and abrasion resistance to polyacetal resin, monomer cast nylon resin, and high-density polyethylene resin.
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ããã Although a catalyst is not particularly required for producing the rigid polyurethane of the present invention, known catalysts such as tertiary amines such as triethylene diamine and organometallic compounds such as dibutyltin dilaurate can also be used. However, isocyanate trimerization catalysts that produce isocyanurate rings are not preferred. It is also possible to obtain an inorganic filler-containing rigid polyurethane by preliminarily mixing the inorganic filler with polyol or polyisocyanate. Examples of inorganic fillers include graphite, silicon carbide, aluminum oxide, and molybdenum disulfide, which are effective in improving hardness, molding shrinkage, friction coefficient, wear resistance, and the like. In the present invention, it is also possible to form a foam by using water, a halogenated hydrocarbon such as trifluorotrichloroethane, or an organic blowing agent such as azobisisobutyronitrile.
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ã©ã®äžæŽ»æ§ã¬ã¹é°å²æ°äžã§è¡ãããšãã§ããã In the present invention, the curing reaction can be carried out, for example, as follows. First, adjust the liquid temperature of the compound to room temperature to 120â.
â, and the temperature of the casting mold is set to 50 to 120â, and the mold is poured, hardened, and demolded. The cured molded product of the present invention is higher than conventional polyurethane molded products even as it is.
Although it has HDT, properties such as impact strength can be improved by further performing heat treatment at a temperature of 140 to 180°C. The heat treatment can be performed in an inert gas atmosphere such as air or nitrogen.
以äžã«åèäŸåã³å®æœäŸãæããŠæ¬çºæã説æ
ããã The present invention will be explained below with reference to reference examples and examples.
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åå¿ããŠåŸãããOH䟡400ã®TDAåºäœããªãªãŒ
ã«50ïœããæãæ··åããªãªãŒã«100ïœåã³ã«ãŒã
ãžã€ããå€æ§MDIïŒæ¥æ¬ããªãŠã¬ã¿ã³ç€Ÿããããª
ãªããŒãMTLãNCOå«æé28.8ïŒ
ïŒ98ïœãããŒ
ã«ãŒäžã§40ç§éãããã©åæ¹ææ©ã§æ¹æãã次ã
ã§ïŒåéç空ãã·ã±ãŒã¿ãŒäžã§è±æ³¡ããããã®æ··
å液ãçŽã¡ã«90âã«å ç±ããå
寞130mmÃ130mmÃ
ïŒmmã®çµç«ãŠåŒã¬ã©ã¹ã¢ãŒã«ãã«æ³šããã¿ã100
âã®ç©ºæ°æ枩槜äžã§30åéåå¿ãããåŸã硬åç©
ãåããåãåºããããã®éæ°æ³¡ã®çºçã¯ã¿ãã
ãªãã€ãã次ãã§160âã®ç©ºæ°æ枩槜äžã§ïŒæé
ç±åŠçãè¡ããç¡çºæ³¡ã®åŒ·éãªç¡¬è³ªããªãŠã¬ã¿ã³
ãåŸããReference Example 1 Propylene oxide adduct of bisphenol A [manufactured by Toho Chiba Chemical Industry Co., Ltd., "Bisol-2P" (approx. 93% of the 2-mole adduct of PO as determined by gas chromatography analysis,
Contains approximately 7% of the 3 molar adduct of PO. OH value 316)]
is heated to 100â and dehydrated under reduced pressure to reduce the moisture content to 0.015.
%. It consists of 50 g of a TDA-based polyol with an OH value of 400 obtained by addition-reacting 50 g of this polyol with 1 mole of 2,4-tolylene diamine (TDA), 5.6 moles of propylene oxide, and 2.6 moles of ethylene oxide, 100 g of a mixed polyol, and carbodiimide modification. 98 g of MDI (Nippon Polyurethane Co., Ltd., "Millionate MTL" NCO content 28.8%) was stirred in a beaker for 40 seconds with a propeller type stirrer, and then defoamed in a vacuum desiccator for 1 minute. This mixture was immediately heated to 90â.Inner dimensions: 130mm x 130mm x
Pour into a 6mm prefabricated glass mold, 100
After reacting for 30 minutes in an air constant temperature bath at â, the cured product was taken out from the mold. During this time, no bubbles were observed. Next, heat treatment was performed for 2 hours in an air constant temperature bath at 160°C to obtain a non-foamed, tough polyurethane.
åŸãããããªãŠã¬ã¿ã³ã®ç±å€åœ¢æž©åºŠãASTMã
D648ã«ããè·é18.6KgïŒcm2ã®æ¡ä»¶äžã§ãæ²ã匟
æ§çãASTMãD790ã«ãããã¢ã€ãŸããè¡æå€
ãASTMãD256ã«ããããããä»ã®æ¡ä»¶äžã§ã
æ©æŠä¿æ°ãæ±æŽããŒã«ããŠã€ã³ç€Ÿè£œã®æ©æŠè©Šéšæ©
ã«ããã也ç¥ç¶æ
ã20ïœïŒminã50KgïŒcm2ã®æ¡ä»¶
äžã§æž¬å®ããã The heat distortion temperature of the obtained polyurethane is determined by ASTM,
The flexural modulus is determined by D648 under a load of 18.6 kg/cm 2 by ASTM, the Izot impact value by D790 is determined by ASTM, and the notched condition is determined by D256.
The coefficient of friction was measured using a friction tester manufactured by Toyo Baldwin under dry conditions at 20 m/min and 50 Kg/cm 2 .
ç±å€åœ¢æž©åºŠ 118â
æ²ã匟æ§ç 27600KgïŒcm2
ã¢ã€ãŸããè¡æå€ 4.0Kgã»cmïŒcm
æ©æŠä¿æ° ÎŒïŒ0.400
PVå€ 200
å®æœäŸ ïŒ
åèäŸïŒã§èª¿è£œããæ··åããªãªãŒã«100ïœãçš
æãããäžæ¹ã«ãŒããžã€ããå€æ§MDIïŒæ¥æ¬ããª
ãŠã¬ã¿ã³ç€ŸãããªãªããŒãMTLããNCOå«æé
28.8ïŒ
ïŒ98ïœã«èèªææ²¹ãšããŠäžžåç³æ²¹è£œROâ
320ã10ïœå ãã80âã«å ç±ããŠæžå§äžã«è±æ°Žã
æ°Žåçã0.014ïŒ
ã«ããããã®äž¡è
ã䜿çšããŠå
èäŸïŒãšåæ§ã«ããŠç¡çºæ³¡ã®åŒ·éãªç¡¬è³ªããªãŠã¬
ã¿ã³ãåŸããHeat deformation temperature 118°C Flexural modulus 27600 Kg/cm 2 Izot impact value 4.0 Kg cm/cm Friction coefficient ÎŒ=0.400 PV value 200 Example 1 100 g of the mixed polyol prepared in Reference Example 1 is prepared. On the other hand, carbodiimide-modified MDI (Japan Polyurethane Co., Ltd. âMillionate MTLâ, NCO content
28.8%) 98g of Maruzen Sekiyu RO as aliphatic oil.
10g of 320 was added, heated to 80°C, and dehydrated under reduced pressure to bring the moisture content to 0.014%. A non-foamed, tough, rigid polyurethane was obtained in the same manner as in Reference Example 1 using both of them.
ç±å€åœ¢æž©åºŠ 113â
æ²ã匟æ§ç 22100KgïŒcm2
ã¢ã€ãŸããè¡æå€ 2.4Kgã»cmïŒcm
æ©æŠä¿æ° ÎŒïŒ0.09
PVå€ 1200
å®æœäŸ ïŒ
ããªã€ãœã·ã¢ããŒããšããŠäœ¿çšããã«ãŒããžã€
ããå€æ§MDIïŒããªãªããŒãMTLïŒ98ïœã«èèª
ææ²¹ïŒäžžåç³æ²¹è£œROâ320ïŒïŒïœåã³è³éŠææ²¹
ïŒå
±åç³æ²¹è£œïŒžâ50FïŒïŒïœãæ·»å ã80âã«å ç±
ããŠæžå§äžã«è±æ°Žãæ°Žåçã0.015ïŒ
ã«ãããã
ãã«åèäŸïŒã®æ··åããªãªãŒã«æå100ïœãæ·»å
ãä»ã¯åèäŸïŒãšåæ§ã«ããŠãç¡çºæ³¡ã®åŒ·éãªç¡¬
質ããªãŠã¬ã¿ã³ãåŸããHeat deformation temperature 113â Flexural modulus 22100Kg/cm 2 Izot impact value 2.4Kgã»cm/cm Friction coefficient ÎŒ=0.09 PV value 1200 Example 2 Aliphatic oil ( 4 g of Maruzen Sekiyu RO-320) and 6 g of aromatic oil (Kyodo Sekiyu X-50F) were added, heated to 80°C, and dehydrated under reduced pressure to bring the moisture content to 0.015%. To this was added 100 g of the mixed polyol component of Reference Example 1, and in the same manner as in Reference Example 1, a non-foamed, tough, rigid polyurethane was obtained.
ç±å€åœ¢æž©åºŠ 108â
æ²ã匟æ§ç 26000KgïŒcm2
ã¢ã€ãŸããè¡æå€ 2.5Kgã»cmïŒcm
æ©æŠä¿æ° ÎŒïŒ0.090
PVå€ 800
æ¯èŒäŸ ïŒ
ããªã¡ãããŒã«ãããã³åºäœã®ããªãªãã·ãã
ãã¬ã³ã°ãªã³ãŒã«ãâ400ãïŒã¢ãã«ç€ŸãOH䟡
391ïŒ100ïœïŒ0.697åœéïŒãšã¹ããžãŠãŒã«44Vâ
20ã®104ïœïŒ0.768åœéïŒãåèäŸïŒãšåæ§ã«ããŠ
åå¿ããïŒãã ãç±åŠçã¯ããªãã€ãïŒãç¡çºæ³¡
ã®ç¡¬è³ªããªãŠã¬ã¿ã³ãåŸããHeat deformation temperature 108â Flexural modulus 26000Kg/cm 2 Izot impact value 2.5Kgã»cm/cm Friction coefficient ÎŒ=0.090 PV value 800 Comparative example 1 Trimethylolpropane-based polyoxypropylene glycol "T-400" (Adeka, OH value
391) 100g (0.697 equivalent) and Sumidyur 44V-
104 g (0.768 equivalent) of 20 was reacted in the same manner as in Reference Example 1 (but without heat treatment) to obtain a non-foamed rigid polyurethane.
ç±å€åœ¢æž©åºŠ 76â
æ²ã匟æ§ç 23800KgïŒcm2
ã¢ã€ãŸããè¡æå€ 3.0Kgã»cmïŒcm
æ©æŠä¿æ° ÎŒïŒ0.500
PVå€ 150
æ¯èŒäŸ ïŒ
åèäŸïŒã§çšããTDAåºäœããªãªãŒã«100ïœãš
ã³ãããŒãMTLïŒ109ïœïŒãçšããŠåèäŸïŒãšå
æ§ã«ããŠåå¿ããç¡çºæ³¡ã®ç¡¬è³ªããªãŠã¬ã¿ã³ãåŸ
ããHeat deformation temperature 76â Bending elastic modulus 23800Kg/cm 2 Izot impact value 3.0Kgã»cm/cm Friction coefficient ÎŒ=0.500 PV value 150 Comparative example 2 Using 100g of TDA base polyol used in Reference example 1 and Coronate MTL (109g) Then, a reaction was carried out in the same manner as in Reference Example 1 to obtain a non-foamed rigid polyurethane.
ç±å€åœ¢æž©åºŠ 102â
æ²ã匟æ§ç 25100KgïŒcm2
ã¢ã€ãŸããè¡æå€ 3.2Kgã»cmïŒcm
æ©æŠä¿æ° ÎŒïŒ0.450
PVå€ 150
æ¯èŒäŸ ïŒ
åèäŸïŒã§çšããTDAåºäœããªãªãŒã«100ïœã
æ¯èŒäŸïŒã§çšããããªãªãŒã«100ïœããžããã«ã
ã³ãžã©ãŠã¬ãŒã0.04ïœãã¢ãã¯ãã«ããªãã«ãªã
ã¡ã¿ã³20ïœãæ··åããããªãªãŒã«æåãšãã¹ããž
ãŠãŒã«44Vâ20ã220ïœçšãåèäŸïŒãšåæ§ã«ã
ãŠïŒãã ãç±åŠçã¯ããªãã€ãïŒãæ¯é0.50ã®ç¡¬
質ããªãŠã¬ã¿ã³çºæ³¡äœãåŸããHeat deformation temperature 102â Flexural modulus 25100Kg/cm 2 Izot impact value 3.2Kgã»cm/cm Friction coefficient ÎŒ=0.450 PV value 150 Comparative example 3 100g of TDA-based polyol used in Reference example 1,
A polyol component prepared by mixing 100 g of the polyol used in Comparative Example 1, 0.04 g of dibutyltin dilaurate, and 20 g of monochlorotrifluoromethane, and 220 g of Sumidyur 44V-20 were used in the same manner as in Reference Example 1 (but without heat treatment), and the specific gravity was determined. A rigid polyurethane foam of 0.50 was obtained.
ç±å€åœ¢æž©åºŠïŒè·é4.6KgïŒcm2ïŒ 83â
æ²ã匟æ§ç 6000KgïŒcm2
æ²ã匷床 184KgïŒcm2
ã¢ã€ãŸããè¡æå€ïŒãããç¡ãïŒ
2.8Kgã»cmïŒcm
æ©æŠä¿æ° ÎŒïŒ1.60
PVå€ 100
æ¯èŒäŸ ïŒ
åèäŸïŒã§çšãããã¹ããšããŒã«ïŒ¡ã®ãããã¬
ã³ãªãã·ãä»å äœïŒBisolâ2PïŒã100âã«å ç±
ããŠæžå§äžã«è±æ°ŽããŠæ°Žåçã0.015ïŒ
ã«ããã
ãã®ããªãªãŒã«50ïœãšãšãã¬ã³ãžã¢ãã³ã«ããã
ã¬ã³ãªãã·ããä»å ããŠåŸãããOH䟡540ïŒå¹³å
ååé415ïŒã®ãšãã¬ã³ãžã¢ãã³åºäœããªãªãŒã«
50ïœããæãæ··åããªãªãŒã«100ïœã«ãèèªææ²¹
ãšããŠäžžåç³æ²¹è£œROâ320ã10ïœå ãã80âã«
å ç±ããŠæžå§äžã«è±æ°ŽããŠæ°Žåçã0.014ïŒ
ã«ã
ãããããããŒã«ãŒã«ç§»ããã«ãŒããžã€ããå€æ§
MDIïŒããªãªããŒãMTLãNCOå«æé28.8ïŒ
ïŒ
117ïœãæ·»å ãããŒã«ãŒäžã§40ç§éãããã©åæ¹
ææ©ã§æ¹æãã次ãã§ïŒåéç空ãã·ã±ãŒã¿ãŒäž
ã§è±æ³¡ããã以äžãåèäŸïŒãšåæ§ã«ããŠç¡¬è³ªã
ãªãŠã¬ã¿ã³ãåŸãŠããã®ç©æ§ãåæ§ã«ããŠæž¬å®ã
ããHeat distortion temperature (load 4.6Kg/cm 2 ) 83â Bending modulus 6000Kg/cm 2 Bending strength 184Kg/cm 2 Izot impact value (without notch)
2.8Kgã»cm/cm Friction coefficient ÎŒ=1.60 PV value 100 Comparative example 4 The propylene oxide adduct of bisphenol A (Bisol-2P) used in Reference Example 1 was heated to 100â and dehydrated under reduced pressure to remove moisture. The rate was set to 0.015%.
Ethylenediamine-based polyol with an OH value of 540 (average molecular weight 415) obtained by adding propylene oxide to 50g of this polyol and ethylenediamine.
To 100 g of a mixed polyol consisting of 50 g, 10 g of RO-320 manufactured by Maruzen Oil was added as an aliphatic oil, heated to 80° C., and dehydrated under reduced pressure to give a moisture content of 0.014%. Transfer this to a beaker and denature it with carbodiimide.
MDI (Millionate MTL, NCO content 28.8%)
117 g was added, stirred in a beaker for 40 seconds with a propeller type stirrer, and then defoamed in a vacuum desiccator for 1 minute. Hereinafter, a rigid polyurethane was obtained in the same manner as in Reference Example 1, and its physical properties were measured in the same manner.
ç±å€åœ¢æž©åºŠ 80â æ²ã匟æ§ç 19260KgïŒcm2 ã¢ã€ãŸããè¡æå€ 3.0Kgã»cmïŒcm æ©æŠä¿æ° ÎŒïŒ0.24 PVå€ 440Heat deformation temperature 80â Flexural modulus 19260Kg/cm 2Izotsu impact value 3.0Kgã»cm/cm Friction coefficient ÎŒ=0.24 PV value 440
Claims (1)
ãŒã«æåãšå°ãªããšãïŒå®èœæ§ã®ããªã€ãœã·ã¢ã
ãŒãæåã®åå¿ã«ããåŸãããããªãŠã¬ã¿ã³ãå«
ãçµæç©ã§ãã€ãŠã該ããªãªãŒã«æåãšããŠïŒïŒ
ïŒâãã¹ïŒïŒâããããã·ããšãã«ïŒãããã³ã®
ãããã¬ã³ãªãã·ãä»å äœã®40ã80éééšåã³æ°Ž
é žåºäŸ¡200ã700ã®è³éŠæã¢ãã³åºäœããªãªãã·ã¢
ã«ãã¬ã³ããªãªãŒã«ã®20ã60éééšãããªãæ··å
ããªãªãŒã«ã䜿çšãã該ããªãªãŒã«æååã³ïŒå
ã¯ããªã€ãœã·ã¢ããŒãæåã«èèªæãããã¯è³éŠ
æã®æ²¹æåãæ·»å ããããšãç¹åŸŽãšããèæ©æŠã
èæ©èæ§ç¡¬è³ªããªãŠã¬ã¿ã³çµæç©ã1 A composition comprising a polyurethane obtained by the reaction of a polyol component having at least a difunctional hydroxyl group and an at least difunctional polyisocyanate component, the polyol component containing 2,
A mixed polyol consisting of 40 to 80 parts by weight of a propylene oxide adduct of 2-bis(4-hydroxyphenyl)propane and 20 to 60 parts by weight of an aromatic amine-based polyoxyalkylene polyol having a hydroxyl value of 200 to 700 is used. , a friction resistant product characterized by adding an aliphatic or aromatic oil component to the polyol component and/or polyisocyanate component;
Abrasion resistant hard polyurethane composition.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP58162338A JPS6053520A (en) | 1983-09-02 | 1983-09-02 | Non-rigid polyurethane having frictional resistance, and wear resistance |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP58162338A JPS6053520A (en) | 1983-09-02 | 1983-09-02 | Non-rigid polyurethane having frictional resistance, and wear resistance |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS6053520A JPS6053520A (en) | 1985-03-27 |
JPS6346766B2 true JPS6346766B2 (en) | 1988-09-19 |
Family
ID=15752651
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP58162338A Granted JPS6053520A (en) | 1983-09-02 | 1983-09-02 | Non-rigid polyurethane having frictional resistance, and wear resistance |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS6053520A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8627658D0 (en) * | 1986-11-19 | 1986-12-17 | Bp Chem Int Ltd | Polyurethane froth foams |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5634721A (en) * | 1979-08-30 | 1981-04-07 | Hitachi Ltd | Rigid polyurethane composition |
-
1983
- 1983-09-02 JP JP58162338A patent/JPS6053520A/en active Granted
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5634721A (en) * | 1979-08-30 | 1981-04-07 | Hitachi Ltd | Rigid polyurethane composition |
Also Published As
Publication number | Publication date |
---|---|
JPS6053520A (en) | 1985-03-27 |
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