JPH0248008B2 - - Google Patents
Info
- Publication number
- JPH0248008B2 JPH0248008B2 JP58135383A JP13538383A JPH0248008B2 JP H0248008 B2 JPH0248008 B2 JP H0248008B2 JP 58135383 A JP58135383 A JP 58135383A JP 13538383 A JP13538383 A JP 13538383A JP H0248008 B2 JPH0248008 B2 JP H0248008B2
- Authority
- JP
- Japan
- Prior art keywords
- glycol
- diisocyanate
- mol
- properties
- solution
- 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 - Lifetime
Links
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 45
- -1 alkylene glycol Chemical compound 0.000 claims description 29
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 22
- 229920002635 polyurethane Polymers 0.000 claims description 15
- 239000004814 polyurethane Substances 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 229920000642 polymer Polymers 0.000 claims description 12
- 229920001281 polyalkylene Polymers 0.000 claims description 8
- 239000012948 isocyanate Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 150000002513 isocyanates Chemical class 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 16
- 238000011084 recovery Methods 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 10
- VJQHJNIGWOABDZ-UHFFFAOYSA-N 3-methyloxetane Chemical compound CC1COC1 VJQHJNIGWOABDZ-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 8
- 150000002009 diols Chemical class 0.000 description 7
- 150000002334 glycols Chemical class 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 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
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 230000003111 delayed effect Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000012656 cationic ring opening polymerization Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920001515 polyalkylene glycol Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920006264 polyurethane film Polymers 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- XBTRYWRVOBZSGM-UHFFFAOYSA-N (4-methylphenyl)methanediamine Chemical compound CC1=CC=C(C(N)N)C=C1 XBTRYWRVOBZSGM-UHFFFAOYSA-N 0.000 description 1
- QXRRAZIZHCWBQY-UHFFFAOYSA-N 1,1-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1(CN=C=O)CCCCC1 QXRRAZIZHCWBQY-UHFFFAOYSA-N 0.000 description 1
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- XCSYDKNASASYDE-UHFFFAOYSA-N 2-aminoethanol hydrazine Chemical compound C(O)CN.NN XCSYDKNASASYDE-UHFFFAOYSA-N 0.000 description 1
- DXTCRSXRMZSEQP-UHFFFAOYSA-N 2-benzofuran-1,3-dione;pyridine Chemical compound C1=CC=NC=C1.C1=CC=C2C(=O)OC(=O)C2=C1 DXTCRSXRMZSEQP-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-M 2-ethylhexanoate Chemical compound CCCCC(CC)C([O-])=O OBETXYAYXDNJHR-UHFFFAOYSA-M 0.000 description 1
- KTLIZDDPOZZHCD-UHFFFAOYSA-N 3-(2-aminoethylamino)propan-1-ol Chemical compound NCCNCCCO KTLIZDDPOZZHCD-UHFFFAOYSA-N 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 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
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- BXKDSDJJOVIHMX-UHFFFAOYSA-N edrophonium chloride Chemical compound [Cl-].CC[N+](C)(C)C1=CC=CC(O)=C1 BXKDSDJJOVIHMX-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 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
- 150000002596 lactones Chemical class 0.000 description 1
- 239000002649 leather substitute Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 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
Description
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The present invention relates to a method for producing a polyurethane polymer having excellent elastic recovery properties, especially elastic recovery properties at low temperatures. In recent years, thermoplastic segmented polyurethane polymers with a two-phase microstructure of a soft domain consisting of flexible so-called soft segments and a hard domain consisting of rigid paracrystalline so-called hard segments aggregated by hydrogen bonding have been developed. It has attracted attention because it can impart properties suitable for the final purpose by changing its concentration, size, size distribution, etc., and has been developed in various ways. Hard segments usually consist of aromatic or aliphatic diisocyanates bonded to short-chain diols or short-chain diamines, while soft segments include polyoxyalkylene glycols, condensed polyester glycols, lactone polyester glycols, polycarbonate diols, etc. used. Among these soft segment components, polyoxyalkylene glycol is preferred for its low-temperature properties and hydrolysis resistance, polyoxytetramethylene glycol is preferred for its excellent mechanical properties and moisture absorption resistance, and polyurethane polymer as fibers, artificial leather, thermoplastic urethane resin,
Used for cast elastomers. It is true that among polyoxyalkylene glycols, polyoxytetramethylene glycol imparts excellent properties to polyurethane polymers as mentioned above, but due to the crystallization tendency of polyoxytetramethylene glycol, it has elastic properties that function as a soft segment. In particular, low-temperature properties such as elastic recovery at low temperatures are not necessarily satisfied, and it is currently desired to improve elastic recovery even at room temperature. The present inventors have conducted intensive research to solve these problems, and have found that when a specific polyalkylene ether diol having a side chain methyl group is used as a soft segment component, excellent low-temperature properties and elastic recovery properties can be obtained. The present invention was achieved by discovering that a polyurethane polymer having the following properties can be obtained. That is, the present invention provides a method for producing a polyurethane polymer from an organic polyfunctional isocyanate and a polyoxyalkylene glycol in the presence or absence of two or more active hydrogen-containing compounds of low molecular weight. The purpose of the present invention is to produce a polyurethane polymer characterized in that at least 10% by weight of the polyalkylene ether diol represented by the following formula (2) is used. HOâ(A-Oâ) n â(BâOâ) o H () (However, if the repeating unit is
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ãã€ã«ã ã®æ§èœãæ¯èŒããŠæ¬¡ã«ç€ºãã[Formula] B is -CH 2 -CH 2 -CH 2 -CH 2 -, m and n are positive values satisfying m+n=6 to 140 and m/n=10/90 to 100/0 (molar ratio). (number) Next, the present invention will be explained in detail. The organic polyfunctional isocyanate used in the present invention is not particularly limited, and any organic diisocyanate or organic triisocyanate that is normally used to obtain a polyurethane polymer can be used. That is, the aromatic diisocyanates include 2,6-tolylene diisocyanate, 2,4-tolylene diisocyanate, 4,
4'-diphenylmethane diisocyanate, 1,5
- Naphthalene diisocyanate, m-xylylene diisocyanate, p-xylylene diisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, tolidine isocyanate, etc. are used. Further, if some degree of crosslinking is required, a small amount of organic triisocyanate such as triphenylmethane triisocyanate or tris(isocyanate phenyl) thiophosphate may be used in combination. As the aliphatic diisocyanate, 1,6-hexamethylene diisocyanate,
1,10-decamethylene diisocyanate, isophorone diisocyanate, bis(isocyanatomethyl)cyclohexane, dicyclohexylmethane diisocyanate, trimethylhexamethylene diisocyanate, lysine diisocyanate, etc. are used. Examples of low molecular weight compounds having two or more active hydrogens include water, ethylenediamine, propylene diamine, phenylene diamine, diphenylmethane diamine, and bifunctional low molecular weight compounds.
Aliphatic or aromatic diamines such as xylene diamine, diols such as ethylene glycol, propylene glycol, butylene glycol, and other ethanolamine hydrazine can be used. These compounds are usually used as chain extenders, and some If cross-linking is required, trifunctional materials such as trimethylolpropane, glycerin, or N,N,N',N'-tetrakis (2-
Tetrafunctional compounds such as (hydroxypropyl) ethylenediamine are used in small amounts as crosslinking agents. Polyoxyalkylene glycols include polyethylene glycol, poly(1,2 and 1,3
-propylene glycol, polyoxytetramethylene glycol, polyoxyhexamethylene glycol, and random or block copolymer glycols obtained from ethylene oxide and propylene oxide or ethylene oxide and tetrahydrofuran. Further, at least 10% by weight, preferably 20% by weight or more of this polyoxyalkylene glycol is a specific polyalkylene ether diol having a side chain methyl group and represented by the above formula (). This particular polyalkylene ether diol can be easily obtained by cationic ring-opening polymerization or cationic ring-opening polymerization of 3-methyloxetane or 3-methyloxetane and tetrahydrofuran, and details regarding its production can be found in Japanese Patent Application No. 57-8610 and This is stated in the specifications of Japanese Patent Application No. 57-8611. That is, it can be obtained by adding perchloric acid and acetic anhydride or perchloric acid and fuming sulfuric acid to a mixed system of 3-methyloxetane or 3-methyloxetane and tetrahydrofuran, or using a super strong acid such as fluorosulfonic acid as a polymerization initiator. The reaction product is saponified to obtain a terminal diol. In the case of a copolymer of 3-methyloxetane and tetrahydrofuran, the 2-methyl-1,3-propylene units and 1,4-tetramethylene units may be distributed randomly or in blocks, and the state of these distributions depends on the copolymerization method and conditions. However, the sum of m and n shown in formula () is approximately 6.
up to 140, preferably between about 9 and 100, and the m/n ratio is 10/90 to 100/0 (molar ratio)
must be satisfied. If the sum of m and n is less than 6, the molecular weight as a soft segment component will be too small and the function of the soft domain will be insufficient, and if it is larger than 140, the handling properties and reactivity during polyurethane production, especially the tendency for phase separation, will deteriorate. It is not desirable in terms of appearance etc. Also, the m/n ratio is good when m is large and approaches 100, that is, a homopolymer of 3-methyloxetane, but it is 10/n.
If the proportion of 3-methyloxetane units in the copolymer is less than 90, that is, less than 10 mol%, the distribution of side chain methyl groups becomes too small, and crystallinity of the polyoxytetramethylene block based on tetrahydrofuran appears, which is the objective. This is not preferable because the low-temperature properties and elastic recovery functions are impaired. For the same reason, the polyalkylene ether diol according to the present invention can be used in combination with other polyalkylene glycols such as polytetramethylene glycol, but the polyalkylene ether diol according to the present invention (formula ()) is at least 10% by weight. It should preferably be used in an amount of 20% by weight or more.
The polyalkylene glycol that can be used in combination is not particularly limited, but polyethylene glycol, polypropylene glycol, random or block copolymers obtained from ethylene oxide and propylene oxide or ethylene oxide and tetrahydrofuran are undesirable because they have too high hydrophilicity, and Poly-1,2 containing alcohol
-Propylene glycol is not preferred because of its low reactivity in polyurethanization. In general, polytetramethylene glycol gives good results because it is easily available on the market. Next is the polyurethanization reaction, which involves the so-called one-shot method in which the reaction components are reacted all at once, or the polyalkylene ether diol of the present invention or a mixture with other polyoxyalkylene glycols to first produce a prepolymer with isocyanate ends and chain extension. A so-called prepolymer method can be used in which low-molecular diols, diamines, etc. are reacted as agents, and anisole, chlorobenzene, o-dichlorobenzene,
The reaction may be carried out in a solution state using a solvent such as -methylpentanone-2, dimethylformamide, or N,N-dimethylacetamide. Furthermore, in order to promote the reaction between the active hydrogen compound and the isocyanate group, tertiary amines such as triethylamine, dimethylethanolamine, 1,8-diazabicyclo[5.4.0]-7-undecene, morpholine derivatives, or dibutyltin are added. Dilaurylate, stannous 2-ethylcaproate, dibutyltin-
Organometallic compounds such as di(2-ethylhexoate) can be used as catalysts. Next, the content of the present invention will be specifically explained with reference to Examples. Note that the hydroxyl values shown in the Examples are values measured by the phthalic anhydride-pyridine method, and the acid values are also values obtained by the direct neutralization titration method of a pyridine solution. Tensile strength and elongation properties are determined from a press sheet with a thickness of approximately 1 mm.
Punch out JIS-compliant dumbbell-shaped test pieces, 23â, 65
The humidity was adjusted for 10 days or more under %RH conditions and then measured using a Tensilon universal tensile tester at a crosshead speed of 50 mm/min. Tensile strength at break, tensile elongation at break,
The tensile yield strength, 100% modulus, and 300% modulus are values determined from the obtained stress-strain curve.
In addition, the instantaneous elastic recovery rate and the delayed elastic recovery rate are determined by attaching a marked line at a distance a to the dumbbell-shaped test piece.
Stretch it to 200% and hold it in this stretched state for 5 minutes, then remove the stress and make it into a free state, then immediately measure the distance between the gauge lines b, and then measure the distance between the gauge lines c again 10 minutes after the stress has been removed. It was measured and calculated from the following formula. Instantaneous elastic recovery rate = 2a-b/a x 100% Delayed elastic recovery rate = 2a-c/a x 100% Example 1 First, a method for producing polyether diol used in the present invention will be described. 6.8 ml of acetic anhydride was added to 100 ml of anhydrous 3-methyloxetane obtained by adding metallic sodium to 3-methyloxetane, which had been dehydrated and dried overnight after adding fresh caustic potash pellets, and then distilled after reflux dehydration. It was cooled to -70°C using cryogen. 2.8 ml of 70% perchloric acid was added dropwise to this system over about 20 minutes with vigorous stirring. After the dropwise addition was completed, stirring was continued for about 1 hour at -70°C, and then the temperature was gradually raised to room temperature over about 1 hour. During this time, the reaction was conducted under a dry nitrogen atmosphere to avoid contact with the atmosphere to prevent moisture absorption. Seal the post-reaction system at room temperature.
It was left for 50 hours. The reaction system became a colorless and transparent viscous liquid. Add about 100ml of pure water to stop the reaction,
The mixture was heated to about 90° C. for about 1 hour while stirring to remove unreacted monomers. After removing the aqueous layer, 200 ml of 1/2N caustic potassium ethanol solution was added, and the mixture was heated and stirred at about 90°C for 2 hours to effect saponification. Ethanol was distilled off, ether was added to make an ether solution, activated carbon and activated clay were added, and the mixture was left to stand for several hours. After the solid content was separated and the ether was distilled off, about 67 g (yield 79.5%) of poly(oxy-2-methylpropylene) glycol was obtained in the form of a colorless and transparent viscous liquid. This product has a hydroxyl value of 100.9mgKOH/g and an acid value of 1.2mg.
KOH/g, number average molecular weight determined from hydroxyl value
It was 1112. Next, polyurethanization was attempted using the obtained poly(oxy-2-methylpropylene) glycol. That is, 20.0 g (0.0180 mol) of poly(oxy-2-methylpropylene) glycol is
Using a ml flask, the mixture was first heated to 100° C. with stirring, and then dehydrated and dried for 1 hour under reduced pressure to about 2 mmHg. The contents were returned to normal pressure with dry nitrogen, and after the temperature had fallen to room temperature, 50 ml of N,N-dimethylacetamide was added and dissolved with stirring. Add 9.0 g (0.0360 mol) of diphenylmethane diisocyanate to this solution.
was dissolved in 50 ml of N,N-dimethylacetamide (partially suspended), and then 1,8
0.05 ml of a 4% N,N-dimethylacetamide solution of -diazabicyclo[5.4.0]-7-undecene (hereinafter abbreviated as DBU) was added and stirred at room temperature for 3 hours. 1.08g of ethylenediamine in this solution
(0.0180 mol) in N,N-dimethylacetamide
A solution dissolved in 25 ml was added dropwise over about 20 minutes, and the reaction was further continued at room temperature for 2 hours. Polyurethane was obtained by adding the reaction product to a large amount of pure water to precipitate the polymer, washing it alternately with water and methanol, and drying it in a vacuum dryer at 60°C for about 10 hours. This polyurethane was dissolved again in N,N-dimethylacetamide, adjusted to a concentration of 10%, and then casted into a glass plate with a silicone mold release agent baked on.
After air drying, water washing, and drying, casting was repeated to produce a film with a predetermined thickness. Comparative Example 1 20 g (0.0199 mol) of poly(oxytetramethylene) glycol with a number average molecular weight of 1003, 9.98 g (0.0399 mol) of diphenylmethane diisocyanate,
A polyurethane film was prepared in the same manner as in Example 1 from 1.20 g (0.0199 mol) of ethylenediamine. The performance of the polyurethane films obtained in Example 1 and Comparative Example 1 will be compared and shown below.
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ã«ã¡ã¿ã³ãžã€ãœã·ã¢ããŒã8.8ïœïŒ0.0352ã¢ã«ïŒ
ããå®æœäŸïŒãšåæ§ã«ããŠããªãŠã¬ã¿ã³ãåŸãã
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ã®ç©æ§å€ã次ã«ç€ºãã[Table] Example 1 is superior to Comparative Example 1 in instantaneous and delayed elastic recovery rates at room temperature and bending recovery rate at low temperatures. Example 2 24.5 g of 3-methyloxetane-tetrahydrofuran (20:80 weight ratio) copolymerized diol with a hydroxyl value of 67.8 and a number average molecular weight of 1656 determined from the hydroxyl value
(0.0148 mol) to 1.8 g of 1,4-butanediol
(0.0200 mol) was added and stirred at about 3 mmHg and 130° C. for 1 hour to simultaneously dry and mix. Continued
While stirring at 130° C., 18 g (0.0348 mol) of diphenylmethane diisocyanate was added in powder form little by little to the reaction system over about 1 hour. After stirring was continued for an additional 4 hours, no increase in the viscosity of the system was observed, so the reaction product was taken out, allowed to cool to room temperature, and then a 1 mm thick press sheet was prepared. Comparative Example 2 24.5 g (0.0163 mol) of polyoxytetramethylene glycol with a number average molecular weight of 1500, 1.7 g (0.0189 mol) of 1,4-butanediol, and 8.8 g (0.0352 mol) of diphenylmethane diisocyanate.
Polyurethane was obtained in the same manner as in Example 2. The physical property values of the polyurethanes obtained in Example 2 and Comparative Example 2 are shown below.
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åŒåŒµç Žæ䌞床 890ïŒ
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300ïŒ
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[Table] Example 3 2.13 g (0.00127 mol) of poly(oxy-2-methyl-1,3-propylene) glycol with a number average molecular weight of 1682 determined from the hydroxyl value and poly(oxy-2-methyl-1,3-propylene) glycol with a number average molecular weight of 1003 determined from the hydroxyl value in the same manner. Oxytetramethylene glycol 7.87g (0.00785mol) 3
Drying and mixing were performed for 1 hour under stirring at 120° C. and mmHg. Add 20 ml of N,N-dimethylacetamide to make a solution Diphenylmethane diisocyanate 4.56
A solution (partial suspension) prepared by adding 40 ml of N,N-dimethylacetamide to G. g (0.01822 mol) was added to the glycol solution. Next, 4%N of DBU,
0.05 ml of N-dimethylacetamide solution was added as a catalyst, and the reaction was carried out at room temperature for about 3 hours. N,N- in which 1.24 g (0.0911 mol) of p-xylene diamine was dissolved in the thus obtained prepolymer solution.
Dimethylacetamide solution was added to the system in about 20 minutes. The reaction was further carried out at room temperature for about 3 hours, and the reaction solution was poured into a large amount of pure water to precipitate the polymer.
As in Example 1, a 1 mm thick sheet was prepared by washing and drying using the solution casting method, and its physical properties were evaluated. Tensile strength at break 255Kgf/ cm2 Tensile elongation at break 890% 100% modulus 80Kgf/ cm2 300% modulus 152Kgf/ cm2 Instant elastic recovery rate 82.0% Delayed elastic recovery rate 95.0%
Claims (1)
ãã¬ã³ã°ãªã³ãŒã«ããäœååéã®ïŒååã¯ïŒå以
äžã®æŽ»æ§æ°ŽçŽ å«æååç©ã®ååšäžåã¯éååšäžã§
ããªãŠã¬ã¿ã³éåäœã補é ããã«ãããã該ããª
ãªãã·ã¢ã«ãã¬ã³ã°ãªã³ãŒã«ã®å å°ããšã10éé
ïŒ ä»¥äžã¯äžèšïŒïŒåŒã§è¡šããããããªã¢ã«ãã¬
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ãªãŠã¬ã¿ã³éåäœã®è£œé æ³ã HOâïŒïŒ¡ââïŒnâïŒïŒ¢ââïŒo ïŒïŒ ïŒäœããç¹°è¿ãåäœã
ãåŒãâãCH2âCH2âCH2 âCH2ââãã§ãããã¯
ãåŒãã¯âCH2âCH2âCH2 âCH2âã§ïœãšïœã¯ïœïŒïœïŒïŒãªãã140ã§ã
ïœïŒïœïŒ10ïŒ90ã100ïŒïŒïŒã¢ã«æ¯ïŒãæºè¶³ããæ£
ã®æ°ïŒ[Claims] 1. In producing a polyurethane polymer from an organic polyfunctional isocyanate and a polyoxyalkylene glycol in the presence or absence of two or more active hydrogen-containing compounds of low molecular weight, the polyoxyalkylene glycol A method for producing a polyurethane polymer, characterized in that at least 10% by weight of the alkylene glycol is a polyalkylene ether diol represented by the following formula (). HO-(A-O-) n -(B-O-) o H () (However, the repeating unit is [Formula]-[CH 2 -CH 2 -CH 2 -CH 2 -O-], and A is [formula] B is âCH 2 âCH 2 âCH 2 âCH 2 â, m and n are m+n=6 to 140,
m/n = 10/90 to 100/0 (a positive number that satisfies the molar ratio)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP58135383A JPS6026021A (en) | 1983-07-25 | 1983-07-25 | Production of polyurethane polymer |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP58135383A JPS6026021A (en) | 1983-07-25 | 1983-07-25 | Production of polyurethane polymer |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS6026021A JPS6026021A (en) | 1985-02-08 |
JPH0248008B2 true JPH0248008B2 (en) | 1990-10-23 |
Family
ID=15150419
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP58135383A Granted JPS6026021A (en) | 1983-07-25 | 1983-07-25 | Production of polyurethane polymer |
Country Status (1)
Country | Link |
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JP (1) | JPS6026021A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS62158428U (en) * | 1986-03-31 | 1987-10-08 |
-
1983
- 1983-07-25 JP JP58135383A patent/JPS6026021A/en active Granted
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JPS6026021A (en) | 1985-02-08 |
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