JPS62164712A - ポリウレタン - Google Patents
ポリウレタンInfo
- Publication number
- JPS62164712A JPS62164712A JP61299809A JP29980986A JPS62164712A JP S62164712 A JPS62164712 A JP S62164712A JP 61299809 A JP61299809 A JP 61299809A JP 29980986 A JP29980986 A JP 29980986A JP S62164712 A JPS62164712 A JP S62164712A
- Authority
- JP
- Japan
- Prior art keywords
- aromatic diamine
- diaminobenzene
- methyl
- mixture
- aromatic
- 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
- 239000004814 polyurethane Substances 0.000 title claims abstract description 68
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 68
- 239000000203 mixture Substances 0.000 claims abstract description 146
- 150000004984 aromatic diamines Chemical class 0.000 claims abstract description 87
- 239000004970 Chain extender Substances 0.000 claims abstract description 67
- 238000009472 formulation Methods 0.000 claims abstract description 47
- 238000006243 chemical reaction Methods 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 22
- 238000010107 reaction injection moulding Methods 0.000 claims description 52
- 150000001875 compounds Chemical class 0.000 claims description 36
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 36
- 125000003277 amino group Chemical group 0.000 claims description 31
- 229920001228 polyisocyanate Polymers 0.000 claims description 31
- 239000005056 polyisocyanate Substances 0.000 claims description 31
- 238000001879 gelation Methods 0.000 claims description 23
- 238000002156 mixing Methods 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 13
- PISLZQACAJMAIO-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine Chemical group CCC1=CC(C)=C(N)C(CC)=C1N PISLZQACAJMAIO-UHFFFAOYSA-N 0.000 claims description 12
- AOFIWCXMXPVSAZ-UHFFFAOYSA-N 4-methyl-2,6-bis(methylsulfanyl)benzene-1,3-diamine Chemical group CSC1=CC(C)=C(N)C(SC)=C1N AOFIWCXMXPVSAZ-UHFFFAOYSA-N 0.000 claims description 11
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 8
- 238000000465 moulding Methods 0.000 claims description 8
- 230000003068 static effect Effects 0.000 claims description 7
- RQEOBXYYEPMCPJ-UHFFFAOYSA-N 4,6-diethyl-2-methylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(C)=C1N RQEOBXYYEPMCPJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000013329 compounding Methods 0.000 claims description 6
- 238000011417 postcuring Methods 0.000 claims description 6
- 150000004982 aromatic amines Chemical class 0.000 claims description 5
- TXDBDYPHJXUHEO-UHFFFAOYSA-N 2-methyl-4,6-bis(methylsulfanyl)benzene-1,3-diamine Chemical compound CSC1=CC(SC)=C(N)C(C)=C1N TXDBDYPHJXUHEO-UHFFFAOYSA-N 0.000 claims description 4
- JGYUBHGXADMAQU-UHFFFAOYSA-N 2,4,6-triethylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(CC)=C1N JGYUBHGXADMAQU-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- OHQOKJPHNPUMLN-UHFFFAOYSA-N n,n'-diphenylmethanediamine Chemical compound C=1C=CC=CC=1NCNC1=CC=CC=C1 OHQOKJPHNPUMLN-UHFFFAOYSA-N 0.000 claims description 2
- OAZIMFHUVDMOJD-UHFFFAOYSA-N 4,6-diethylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C=C1N OAZIMFHUVDMOJD-UHFFFAOYSA-N 0.000 claims 1
- QBYNWJVTTUAPCT-UHFFFAOYSA-N n,n'-bis(2-chlorophenyl)methanediamine Chemical group ClC1=CC=CC=C1NCNC1=CC=CC=C1Cl QBYNWJVTTUAPCT-UHFFFAOYSA-N 0.000 claims 1
- SPJPZHZTYJKFEZ-UHFFFAOYSA-N n-chloro-4-[[4-(chloroamino)phenyl]methyl]aniline Chemical compound C1=CC(NCl)=CC=C1CC1=CC=C(NCl)C=C1 SPJPZHZTYJKFEZ-UHFFFAOYSA-N 0.000 claims 1
- 150000004985 diamines Chemical class 0.000 abstract description 43
- 238000011049 filling Methods 0.000 abstract description 5
- 239000000047 product Substances 0.000 description 43
- 229920005989 resin Polymers 0.000 description 29
- 239000011347 resin Substances 0.000 description 29
- 229920005862 polyol Polymers 0.000 description 21
- 150000003077 polyols Chemical class 0.000 description 20
- 229920000570 polyether Polymers 0.000 description 19
- 239000012948 isocyanate Substances 0.000 description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 17
- 150000002513 isocyanates Chemical class 0.000 description 17
- 239000004606 Fillers/Extenders Substances 0.000 description 16
- -1 araliphatic Chemical class 0.000 description 16
- 125000003118 aryl group Chemical group 0.000 description 14
- HGXVKAPCSIXGAK-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine;4,6-diethyl-2-methylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(C)=C1N.CCC1=CC(C)=C(N)C(CC)=C1N HGXVKAPCSIXGAK-UHFFFAOYSA-N 0.000 description 13
- 238000002474 experimental method Methods 0.000 description 13
- 239000004721 Polyphenylene oxide Substances 0.000 description 12
- 230000000704 physical effect Effects 0.000 description 12
- 229920000728 polyester Polymers 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- 125000004427 diamine group Chemical group 0.000 description 10
- 229940018564 m-phenylenediamine Drugs 0.000 description 10
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 125000000217 alkyl group Chemical class 0.000 description 7
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 7
- 238000003672 processing method Methods 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 150000001412 amines Chemical group 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- XEOHXAGSQXJEMA-UHFFFAOYSA-N 1-n,3-n,3-n-triethylbenzene-1,3-diamine Chemical compound CCNC1=CC=CC(N(CC)CC)=C1 XEOHXAGSQXJEMA-UHFFFAOYSA-N 0.000 description 4
- 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 4
- IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 description 4
- 125000001118 alkylidene group Chemical group 0.000 description 4
- 238000005576 amination reaction Methods 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000000806 elastomer Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 239000006082 mold release agent Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000011342 resin composition Substances 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical class CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-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
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000012973 diazabicyclooctane Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 125000004708 n-butylthio group Chemical group C(CCC)S* 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical group NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 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
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-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
- 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
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 1
- DAGJULOUFIPTPP-UHFFFAOYSA-N 1-phenylpropane-1,1-diamine Chemical compound CCC(N)(N)C1=CC=CC=C1 DAGJULOUFIPTPP-UHFFFAOYSA-N 0.000 description 1
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- TZFFGICBCZBYDO-UHFFFAOYSA-N 2-ethyl-4-methyl-6-propan-2-ylbenzene-1,3-diamine Chemical compound CCC1=C(N)C(C)=CC(C(C)C)=C1N TZFFGICBCZBYDO-UHFFFAOYSA-N 0.000 description 1
- GAFYTSWTNFTKFJ-UHFFFAOYSA-N 2-methyl-4-propan-2-ylbenzene-1,3-diamine Chemical compound CC(C)C1=CC=C(N)C(C)=C1N GAFYTSWTNFTKFJ-UHFFFAOYSA-N 0.000 description 1
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical class C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- WYFASPGXAKVSBC-UHFFFAOYSA-N 4,6-dicyclopentylbenzene-1,3-diamine Chemical compound NC1=CC(N)=C(C2CCCC2)C=C1C1CCCC1 WYFASPGXAKVSBC-UHFFFAOYSA-N 0.000 description 1
- PMYILJRWFYETBQ-UHFFFAOYSA-N 4-(2-aminoethyl)-2,6-bis(methylsulfanyl)aniline Chemical compound CSC1=CC(CCN)=CC(SC)=C1N PMYILJRWFYETBQ-UHFFFAOYSA-N 0.000 description 1
- JZIRFOSDEONPNA-UHFFFAOYSA-N 4-(2-methylpropyl)-6-propan-2-ylbenzene-1,3-diamine Chemical compound CC(C)CC1=CC(C(C)C)=C(N)C=C1N JZIRFOSDEONPNA-UHFFFAOYSA-N 0.000 description 1
- IZXPXYHPDDSUTR-UHFFFAOYSA-N 4-(methylsulfanylmethyl)benzene-1,3-diamine Chemical compound CSCC1=CC=C(N)C=C1N IZXPXYHPDDSUTR-UHFFFAOYSA-N 0.000 description 1
- YCRAOKVEGACLCK-UHFFFAOYSA-N 4-[(4-amino-3-methylsulfanylphenyl)methyl]-2,6-bis(methylsulfanyl)aniline Chemical compound C1=C(N)C(SC)=CC(CC=2C=C(SC)C(N)=C(SC)C=2)=C1 YCRAOKVEGACLCK-UHFFFAOYSA-N 0.000 description 1
- WGXCSHNHXHXHBS-UHFFFAOYSA-N 4-[(4-amino-3-tert-butyl-5-methylphenyl)methyl]-2-tert-butyl-6-methylaniline Chemical compound CC(C)(C)C1=C(N)C(C)=CC(CC=2C=C(C(N)=C(C)C=2)C(C)(C)C)=C1 WGXCSHNHXHXHBS-UHFFFAOYSA-N 0.000 description 1
- HMNSOADMBBTZCU-UHFFFAOYSA-N 4-[1-[4-amino-3,5-bis(ethylsulfanyl)phenyl]ethyl]-2,6-bis(ethylsulfanyl)aniline Chemical compound CCSC1=C(N)C(SCC)=CC(C(C)C=2C=C(SCC)C(N)=C(SCC)C=2)=C1 HMNSOADMBBTZCU-UHFFFAOYSA-N 0.000 description 1
- PFGGVOPKHDCPQV-UHFFFAOYSA-N 4-[2-[4-amino-3,5-bis(methylsulfanyl)phenyl]propan-2-yl]-2,6-bis(methylsulfanyl)aniline Chemical compound CSC1=C(N)C(SC)=CC(C(C)(C)C=2C=C(SC)C(N)=C(SC)C=2)=C1 PFGGVOPKHDCPQV-UHFFFAOYSA-N 0.000 description 1
- XMLAILXBSMPLFI-UHFFFAOYSA-N 4-[4-amino-3,5-bis(ethylsulfanyl)phenoxy]-2,6-bis(methylsulfanyl)aniline Chemical compound CCSC1=C(N)C(SCC)=CC(OC=2C=C(SC)C(N)=C(SC)C=2)=C1 XMLAILXBSMPLFI-UHFFFAOYSA-N 0.000 description 1
- QKSSKKVHMHRJOV-UHFFFAOYSA-N 4-[4-amino-3,5-bis(ethylsulfanyl)phenyl]sulfanyl-2,6-bis(methylsulfanyl)aniline Chemical compound CCSC1=C(N)C(SCC)=CC(SC=2C=C(SC)C(N)=C(SC)C=2)=C1 QKSSKKVHMHRJOV-UHFFFAOYSA-N 0.000 description 1
- KBGOTVMUFHPSMN-UHFFFAOYSA-N 4-[[4-amino-3,5-bis(ethylsulfanyl)phenyl]methyl]-2,6-bis(ethylsulfanyl)aniline Chemical compound CCSC1=C(N)C(SCC)=CC(CC=2C=C(SCC)C(N)=C(SCC)C=2)=C1 KBGOTVMUFHPSMN-UHFFFAOYSA-N 0.000 description 1
- JYUIECGDBUMGQU-UHFFFAOYSA-N 4-benzyl-2,6-bis(methylsulfanyl)benzene-1,3-diamine Chemical compound CSC1=C(N)C(SC)=CC(CC=2C=CC=CC=2)=C1N JYUIECGDBUMGQU-UHFFFAOYSA-N 0.000 description 1
- FSPSZQKQXYGKSJ-UHFFFAOYSA-N 4-butan-2-yl-6-ethylbenzene-1,3-diamine Chemical compound CCC(C)C1=CC(CC)=C(N)C=C1N FSPSZQKQXYGKSJ-UHFFFAOYSA-N 0.000 description 1
- LRDZQHBXYHWKJA-UHFFFAOYSA-N 4-butan-2-yl-6-propan-2-ylbenzene-1,3-diamine Chemical compound CCC(C)C1=CC(C(C)C)=C(N)C=C1N LRDZQHBXYHWKJA-UHFFFAOYSA-N 0.000 description 1
- JVVNJZKPRKIBLZ-UHFFFAOYSA-N 4-ethylsulfanyl-2-methylsulfanylbenzene-1,3-diamine Chemical compound CCSC1=CC=C(N)C(SC)=C1N JVVNJZKPRKIBLZ-UHFFFAOYSA-N 0.000 description 1
- TVEDFXNIYIAMMO-UHFFFAOYSA-N 4-methyl-2,6-bis(methylsulfanyl)-5-nitrobenzene-1,3-diamine Chemical compound CSC1=C(N)C(C)=C([N+]([O-])=O)C(SC)=C1N TVEDFXNIYIAMMO-UHFFFAOYSA-N 0.000 description 1
- WXTWKTAJDWVZGO-UHFFFAOYSA-N 4-tert-butyl-6-(2-methylpropyl)benzene-1,3-diamine Chemical compound CC(C)CC1=CC(C(C)(C)C)=C(N)C=C1N WXTWKTAJDWVZGO-UHFFFAOYSA-N 0.000 description 1
- LZGHSEZWJLSOSI-UHFFFAOYSA-N 4-tert-butyl-6-ethylbenzene-1,3-diamine Chemical compound CCC1=CC(C(C)(C)C)=C(N)C=C1N LZGHSEZWJLSOSI-UHFFFAOYSA-N 0.000 description 1
- YCPZQHZNPZTIJE-UHFFFAOYSA-N 4-tert-butyl-6-propan-2-ylbenzene-1,3-diamine Chemical compound CC(C)C1=CC(C(C)(C)C)=C(N)C=C1N YCPZQHZNPZTIJE-UHFFFAOYSA-N 0.000 description 1
- RGIVJOYIHZVLFO-UHFFFAOYSA-N 5-bromo-4,6-bis(butylsulfanyl)-2-methylbenzene-1,3-diamine Chemical compound CCCCSC1=C(N)C(C)=C(N)C(SCCCC)=C1Br RGIVJOYIHZVLFO-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000009261 D 400 Substances 0.000 description 1
- 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 1
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- SVWNTXIXBYPFID-UHFFFAOYSA-N N-(ethylaminosulfanyl)ethanamine Chemical class C(C)NSNCC SVWNTXIXBYPFID-UHFFFAOYSA-N 0.000 description 1
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- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 1
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- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
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- 150000001718 carbodiimides Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
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- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- VZSDWRJYMYVVEU-UHFFFAOYSA-N hexa-1,3,4-triene Chemical group CC=C=CC=C VZSDWRJYMYVVEU-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000004988 m-phenylenediamines Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- 239000000594 mannitol Substances 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QTMAORGVJKBZJO-UHFFFAOYSA-N methylsulfanyl(phenyl)methanediamine Chemical compound CSC(N)(N)C1=CC=CC=C1 QTMAORGVJKBZJO-UHFFFAOYSA-N 0.000 description 1
- LHFDSCKKVIUJJV-UHFFFAOYSA-N n-(2-chlorophenyl)methanimine Chemical compound ClC1=CC=CC=C1N=C LHFDSCKKVIUJJV-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012970 tertiary amine catalyst Substances 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 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
- 150000004998 toluenediamines Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/80—Masked polyisocyanates
- C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
- C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
- C08G18/8009—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203
- C08G18/8012—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203 with diols
- C08G18/8019—Masked aromatic polyisocyanates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/6505—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen the low-molecular compounds being compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6523—Compounds of group C08G18/3225 or C08G18/3271 or polyamines of C08G18/38
- C08G18/6529—Compounds of group C08G18/3225 or polyamines of C08G18/38
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2120/00—Compositions for reaction injection moulding processes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/809,563 US4631298A (en) | 1985-12-16 | 1985-12-16 | Mixed diamine chain extender |
| US809563 | 1985-12-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62164712A true JPS62164712A (ja) | 1987-07-21 |
| JPH0513962B2 JPH0513962B2 (enExample) | 1993-02-23 |
Family
ID=25201627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61299809A Granted JPS62164712A (ja) | 1985-12-16 | 1986-12-16 | ポリウレタン |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4631298A (enExample) |
| EP (1) | EP0228190B1 (enExample) |
| JP (1) | JPS62164712A (enExample) |
| AT (1) | ATE61061T1 (enExample) |
| CA (1) | CA1269477A (enExample) |
| DE (1) | DE3677738D1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003511116A (ja) * | 1999-10-01 | 2003-03-25 | スポルディング、スポーツ、ワールドワイド、インク | 高速化学反応により生成された成分を含むゴルフボール及びその製造方法。 |
| JP2009520066A (ja) * | 2005-12-15 | 2009-05-21 | バイエル・マテリアルサイエンス・リミテッド・ライアビリティ・カンパニー | イソホロンジイソシアネートのイソシアヌレートおよびそのプレポリマーに基づくｒｉｍエラストマー |
Families Citing this family (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3378055D1 (en) * | 1982-09-17 | 1988-10-27 | Ici Plc | Polyurea dispersions in organic isocyanates |
| DE3782076T2 (de) * | 1986-03-26 | 1993-04-15 | Ici Plc | Verwendung von polymerpolyaminen fuer die herstellung von polyurethan/polyharnstoffen oder polyharnstoffen. |
| US4806615A (en) * | 1987-06-01 | 1989-02-21 | Texaco Inc. | Reaction injection molded elastomers prepared from amine terminated polyethers, a blend of an aromatic amine terminated chain extender, a substituted acyclic aliphatic amine terminated chain extender and an aromatic polyisocyanate |
| DE3732726A1 (de) * | 1987-09-29 | 1989-04-06 | Bayer Ag | Verfahren zur herstellung von polyurethanharnstoff-elastomeren |
| US4948861A (en) * | 1987-12-09 | 1990-08-14 | Uop | N,N'-dialkylphenylenediamines as curing agents in polyurethane and polyurea manufacture by reaction injection molding |
| US4897430A (en) * | 1988-10-31 | 1990-01-30 | Texaco Chemical Company | One Component polyurea |
| US5141967A (en) * | 1989-07-28 | 1992-08-25 | Miles Inc. | Process for the preparation of polyurea-polyurethane elastomers |
| US5124426A (en) * | 1989-09-26 | 1992-06-23 | Texaco Chemical Company | Sprayable polyurea elastomer made from reaction of isocyanate compound with amine terminated polyether and di(methylthio)toluene diamine and diethyltoluene diamine chain extenders |
| US5002806A (en) * | 1990-01-11 | 1991-03-26 | Ashland Oil, Inc. | Curative for structural urethane adhesive |
| US5059634A (en) * | 1990-02-09 | 1991-10-22 | Resin Design International Corp. | High flexual modulus polyurethane polymers and rim processes employing said polymers |
| US5219973A (en) * | 1990-12-07 | 1993-06-15 | Miles Inc. | Polyurea rim systems |
| US5166299A (en) * | 1991-09-09 | 1992-11-24 | Ethyl Corporation | Polyurethanes comprising the reaction product of an isocyanate prepolymer and isomers of di(methylthio)-diaminotoluene |
| US5143942A (en) * | 1991-10-28 | 1992-09-01 | Ethyl Corporation | Polyurethanes |
| US5166115A (en) * | 1991-10-28 | 1992-11-24 | Brown William R | Polyurethanes |
| FR2696344B1 (fr) * | 1992-10-02 | 1994-11-25 | Oreal | Utilisation en teinture des fibres kératiniques de métaphénylènediamines soufrées et nouvelles métaphénylènediamines soufrées. |
| US5418260A (en) * | 1993-10-04 | 1995-05-23 | Ecp Enichem Polimeri Netherlands, B.V. | Process for the production of polyurethane articles from uretonimine based compositions and ethylene oxide rich polyether polyols |
| US5422414A (en) * | 1993-10-04 | 1995-06-06 | Ecp Enichem Polimeri Netherlands B.V. | Modified polyurea-polyurethane systems endowed with improved processability |
| US5502147A (en) * | 1993-12-21 | 1996-03-26 | Bayer Corporation | Aliphatic rim elastomers |
| US6197242B1 (en) | 1994-06-17 | 2001-03-06 | Bayer Corporation | Injection molding fibers embedded in polyurethane with hindered amine |
| US5688590A (en) * | 1995-08-21 | 1997-11-18 | Bayer Corporation | High heat resistant molded parts produced by structural reaction injection molding |
| US6793864B1 (en) * | 1997-02-26 | 2004-09-21 | Dunlop Sports | Polyurethane material for two and three piece golf balls |
| US7244384B1 (en) | 1998-02-04 | 2007-07-17 | Taylormade-Adidas Golf Company | Method for manufacturing two and three piece golf balls constructed from polyurethane material |
| US7223181B2 (en) * | 1998-02-04 | 2007-05-29 | Taylormade-Adidas Golf Company | Polyurethane material for two and three piece golf balls and method |
| US5962619A (en) * | 1998-03-16 | 1999-10-05 | Arco Chemical Technology, L.P. | Process for making clear polyurethane/urea elastomers |
| US6291019B1 (en) | 1998-06-18 | 2001-09-18 | Mackinac Investors, Llc | Method for damping noise, vibration and harshness of a substrate |
| US6174984B1 (en) * | 1999-06-14 | 2001-01-16 | Uniroyal Chemical Company, Inc. | Clear, resilient polyurethane elastomers |
| US6530849B2 (en) | 1999-09-15 | 2003-03-11 | Uniroyal Chemical Company, Inc. | Low cost, resilient, shear resistant polyurethane elastomers for golf ball covers |
| US6309313B1 (en) | 1999-09-15 | 2001-10-30 | Uniroyal Chemical Company, Inc. | Low cost, resilient, shear resistant polyurethane elastomers for golf ball covers |
| US6719646B2 (en) | 2000-01-25 | 2004-04-13 | Dunlop Slazenger Sports | Polyurethane covered three-piece golf ball |
| BR0114127A (pt) | 2000-09-11 | 2003-07-22 | Dow Global Technologies Inc | Método de dispositivo para preparar suporte de pneu |
| AU2001291290B2 (en) | 2000-09-11 | 2006-06-15 | The Dow Chemical Company | Run flat tire support |
| EP1404732B1 (en) | 2001-06-15 | 2007-07-25 | Huntsman Petrochemical Corporation | Synergistic amine chain-extenders in polyurea spray elastomers |
| US6699957B2 (en) | 2002-02-01 | 2004-03-02 | Uniroyal Chemical Company, Inc. | Resilient, shear resistant polyurethane compositions for golf ball covers |
| US6787626B2 (en) * | 2002-05-31 | 2004-09-07 | Callaway Golf Company | Thermosetting polyurethane material for a golf ball cover |
| US7244802B2 (en) * | 2002-05-31 | 2007-07-17 | Callaway Golf Company | Thermosetting polyurethane material for a golf ball |
| US20030224876A1 (en) * | 2002-05-31 | 2003-12-04 | Callaway Golf Company | Thermosetting polyurethane material for a golf ball cover |
| US6762273B2 (en) * | 2002-05-31 | 2004-07-13 | Callaway Golf Company | Thermosetting polyurethane material for a golf ball cover |
| US6765080B2 (en) | 2002-06-06 | 2004-07-20 | Bayer Corporation | High performance RIM elastomers and a process for their production |
| US7121961B2 (en) * | 2004-04-07 | 2006-10-17 | Callaway Golf Company | Low volume cover for a golf ball |
| US7060777B1 (en) * | 2004-12-07 | 2006-06-13 | Callaway Golf Company | Polyurethane material for a golf ball cover |
| US7101952B2 (en) * | 2004-12-08 | 2006-09-05 | Callaway Golf Company | Polyurethane material for a golf ball cover |
| US20060178497A1 (en) * | 2005-02-04 | 2006-08-10 | Clemson University And Thordon Bearings, Inc. | Implantable biomedical devices including biocompatible polyurethanes |
| US8076518B2 (en) | 2005-03-28 | 2011-12-13 | Albemarle Corporation | Chain extenders |
| KR101264458B1 (ko) * | 2005-03-28 | 2013-05-21 | 알베마를 코포레이션 | 디이민 및 2 차 디아민 |
| US7964695B2 (en) * | 2005-03-28 | 2011-06-21 | Albemarle Corporation | Chain extenders |
| CA2630407A1 (en) * | 2005-12-30 | 2007-07-12 | Albemarle Corporation | Diamines having reduced color |
| EA200870135A1 (ru) * | 2005-12-30 | 2009-12-30 | Альбемарл Корпорейшн | Смеси диаминов, имеющие ослабленный цвет |
| US20070225393A1 (en) * | 2006-03-27 | 2007-09-27 | Arnold Allen R Jr | Crosslinkers for minimizing deterioration of polyurethane foams |
| JP2010515811A (ja) * | 2007-01-10 | 2010-05-13 | アルベマール・コーポレーシヨン | 反応射出成形および噴霧システムのための組成物 |
| JP5588343B2 (ja) * | 2007-07-20 | 2014-09-10 | インヴィスタ テクノロジーズ エスアエルエル | ポリウレタンフォームボールの改良された製造 |
| US20120035001A1 (en) | 2009-04-30 | 2012-02-09 | Dow Global Technologies Llc | Castable polyurea compositions for golf ball covers |
| CN102918073B (zh) | 2010-03-31 | 2014-12-10 | 陶氏环球技术有限责任公司 | 具有改善抗冲击性和光学性质的聚氨酯组合物 |
| EP2426157A1 (en) * | 2010-09-02 | 2012-03-07 | Lonza Ltd. | Diamine compositions and use thereof |
| WO2015189045A1 (en) * | 2014-06-11 | 2015-12-17 | Basf Se | Polyurethane compound for producing an integrated insulation component |
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| JPS546257A (en) * | 1977-06-15 | 1979-01-18 | Kasai Kk | Folding type baby car |
| JPS5832629A (ja) * | 1981-08-21 | 1983-02-25 | Asahi Glass Co Ltd | ポリアリ−レン・エチニレンの製造方法 |
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- 1986-11-28 DE DE8686309333T patent/DE3677738D1/de not_active Expired - Lifetime
- 1986-11-28 EP EP86309333A patent/EP0228190B1/en not_active Expired - Lifetime
- 1986-11-28 AT AT86309333T patent/ATE61061T1/de not_active IP Right Cessation
- 1986-12-16 JP JP61299809A patent/JPS62164712A/ja active Granted
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| JPS546257A (en) * | 1977-06-15 | 1979-01-18 | Kasai Kk | Folding type baby car |
| JPS5832629A (ja) * | 1981-08-21 | 1983-02-25 | Asahi Glass Co Ltd | ポリアリ−レン・エチニレンの製造方法 |
| JPS60181118A (ja) * | 1984-02-09 | 1985-09-14 | エアー．プロダクツ．アンド．ケミカルス．インコーポレーテツド | ポリウレタン尿素エラストマーの製造方法 |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003511116A (ja) * | 1999-10-01 | 2003-03-25 | スポルディング、スポーツ、ワールドワイド、インク | 高速化学反応により生成された成分を含むゴルフボール及びその製造方法。 |
| JP4796255B2 (ja) * | 1999-10-01 | 2011-10-19 | キャラウェイ・ゴルフ・カンパニ | 高速化学反応により生成された成分を含むゴルフボール及びその製造方法。 |
| JP2009520066A (ja) * | 2005-12-15 | 2009-05-21 | バイエル・マテリアルサイエンス・リミテッド・ライアビリティ・カンパニー | イソホロンジイソシアネートのイソシアヌレートおよびそのプレポリマーに基づくｒｉｍエラストマー |
| KR101360649B1 (ko) * | 2005-12-15 | 2014-02-07 | 바이엘 머티리얼싸이언스 엘엘씨 | 이소포론 디이소시아네이트의 이소시아누레이트 및 그의예비중합체를 기재로 하는 ｒｉｍ 엘라스토머 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0228190A3 (en) | 1988-01-13 |
| EP0228190B1 (en) | 1991-02-27 |
| EP0228190A2 (en) | 1987-07-08 |
| JPH0513962B2 (enExample) | 1993-02-23 |
| US4631298A (en) | 1986-12-23 |
| ATE61061T1 (de) | 1991-03-15 |
| DE3677738D1 (de) | 1991-04-04 |
| CA1269477A (en) | 1990-05-22 |
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