CA2627322C - Polyurethane-urea elastomers - Google Patents
Polyurethane-urea elastomers Download PDFInfo
- Publication number
- CA2627322C CA2627322C CA2627322A CA2627322A CA2627322C CA 2627322 C CA2627322 C CA 2627322C CA 2627322 A CA2627322 A CA 2627322A CA 2627322 A CA2627322 A CA 2627322A CA 2627322 C CA2627322 C CA 2627322C
- Authority
- CA
- Canada
- Prior art keywords
- weight
- molecular weight
- isocyanate
- polyurethane
- nco
- 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 - Fee Related
Links
- 229920003226 polyurethane urea Polymers 0.000 title claims abstract description 56
- 229920001971 elastomer Polymers 0.000 title description 13
- 239000000806 elastomer Substances 0.000 title description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 89
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 63
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 57
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 57
- 238000000034 method Methods 0.000 claims abstract description 46
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 33
- 125000003118 aryl group Chemical group 0.000 claims abstract description 31
- 150000004984 aromatic diamines Chemical class 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- 229920005862 polyol Polymers 0.000 claims description 124
- 150000003077 polyols Chemical class 0.000 claims description 124
- 239000000203 mixture Substances 0.000 claims description 97
- -1 aromatic diamine compounds Chemical class 0.000 claims description 64
- 239000012948 isocyanate Substances 0.000 claims description 56
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 55
- 150000002513 isocyanates Chemical class 0.000 claims description 55
- 239000003054 catalyst Substances 0.000 claims description 54
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 39
- 150000003335 secondary amines Chemical group 0.000 claims description 36
- 229920000570 polyether Polymers 0.000 claims description 31
- 229920005906 polyester polyol Polymers 0.000 claims description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 150000002148 esters Chemical class 0.000 claims description 23
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 22
- 150000002894 organic compounds Chemical class 0.000 claims description 21
- PISLZQACAJMAIO-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine Chemical compound CCC1=CC(C)=C(N)C(CC)=C1N PISLZQACAJMAIO-UHFFFAOYSA-N 0.000 claims description 18
- 229920000608 Polyaspartic Chemical group 0.000 claims description 17
- 150000004985 diamines Chemical group 0.000 claims description 17
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 16
- 239000004970 Chain extender Substances 0.000 claims description 15
- 125000003263 primary aromatic amine group Chemical group 0.000 claims description 12
- 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 11
- 229920001610 polycaprolactone Polymers 0.000 claims description 10
- 239000004632 polycaprolactone Substances 0.000 claims description 7
- AZYRZNIYJDKRHO-UHFFFAOYSA-N 1,3-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC(C(C)(C)N=C=O)=C1 AZYRZNIYJDKRHO-UHFFFAOYSA-N 0.000 claims description 5
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 claims description 5
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 claims description 5
- 239000004971 Cross linker Substances 0.000 claims description 5
- 150000004982 aromatic amines Chemical group 0.000 claims description 5
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 claims description 4
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 4
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 claims description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 4
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 claims description 3
- UTNMPUFESIRPQP-UHFFFAOYSA-N 2-[(4-aminophenyl)methyl]aniline Chemical compound C1=CC(N)=CC=C1CC1=CC=CC=C1N UTNMPUFESIRPQP-UHFFFAOYSA-N 0.000 claims description 3
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical class CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 claims description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 3
- 150000003141 primary amines Chemical group 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 24
- 239000007787 solid Substances 0.000 abstract description 17
- 239000000463 material Substances 0.000 abstract description 10
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 abstract description 2
- 238000011417 postcuring Methods 0.000 abstract 1
- 239000004814 polyurethane Substances 0.000 description 32
- 229920002635 polyurethane Polymers 0.000 description 31
- 239000000654 additive Substances 0.000 description 24
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 21
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 150000002009 diols Chemical class 0.000 description 16
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 16
- 239000006082 mold release agent Substances 0.000 description 16
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 150000001991 dicarboxylic acids Chemical class 0.000 description 12
- 229920000728 polyester Polymers 0.000 description 12
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 11
- 239000003999 initiator Substances 0.000 description 11
- 230000003287 optical effect Effects 0.000 description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000003963 antioxidant agent Substances 0.000 description 10
- 235000006708 antioxidants Nutrition 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 229920000515 polycarbonate Polymers 0.000 description 9
- 239000004417 polycarbonate Substances 0.000 description 9
- 239000003381 stabilizer Substances 0.000 description 9
- 230000000996 additive effect Effects 0.000 description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 229940018564 m-phenylenediamine Drugs 0.000 description 8
- 150000005846 sugar alcohols Polymers 0.000 description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- 239000013530 defoamer Substances 0.000 description 7
- 125000005442 diisocyanate group Chemical group 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 150000004072 triols Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 229920002396 Polyurea Polymers 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012963 UV stabilizer Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- 238000005266 casting Methods 0.000 description 6
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 6
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 6
- 230000032050 esterification Effects 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- 150000002334 glycols Chemical class 0.000 description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 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 5
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 235000013877 carbamide Nutrition 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 5
- 239000011976 maleic acid Substances 0.000 description 5
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000002834 transmittance Methods 0.000 description 5
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 229920001730 Moisture cure polyurethane Polymers 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
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
- 239000001361 adipic acid Substances 0.000 description 4
- 235000011037 adipic acid Nutrition 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- VEIOBOXBGYWJIT-UHFFFAOYSA-N cyclohexane;methanol Chemical compound OC.OC.C1CCCCC1 VEIOBOXBGYWJIT-UHFFFAOYSA-N 0.000 description 4
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 239000000543 intermediate Substances 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
- 150000002596 lactones Chemical class 0.000 description 4
- 239000004611 light stabiliser Substances 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- 150000002924 oxiranes Chemical class 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
- 229920000768 polyamine Polymers 0.000 description 4
- 229920006324 polyoxymethylene Polymers 0.000 description 4
- 229920000909 polytetrahydrofuran Polymers 0.000 description 4
- 229920006295 polythiol Polymers 0.000 description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 4
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 229920000805 Polyaspartic acid Polymers 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 229910052797 bismuth Inorganic materials 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- GNGYPJUKIKDJQT-UHFFFAOYSA-N ethyl 4-[(n-methylanilino)methylideneamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N=CN(C)C1=CC=CC=C1 GNGYPJUKIKDJQT-UHFFFAOYSA-N 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000006353 oxyethylene group Chemical group 0.000 description 3
- 108010064470 polyaspartate Proteins 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 2
- 229940058015 1,3-butylene glycol Drugs 0.000 description 2
- 229940035437 1,3-propanediol Drugs 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 description 2
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 2
- IYAZLDLPUNDVAG-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IYAZLDLPUNDVAG-UHFFFAOYSA-N 0.000 description 2
- QEAHTUJZOZSKCY-UHFFFAOYSA-N 2-(hydroxymethyl)-2-methylbutane-1,3-diol Chemical compound CC(O)C(C)(CO)CO QEAHTUJZOZSKCY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- IAXFZZHBFXRZMT-UHFFFAOYSA-N 2-[3-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=CC(OCCO)=C1 IAXFZZHBFXRZMT-UHFFFAOYSA-N 0.000 description 2
- WTPYFJNYAMXZJG-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=C(OCCO)C=C1 WTPYFJNYAMXZJG-UHFFFAOYSA-N 0.000 description 2
- JUKWFOVSARANHP-UHFFFAOYSA-N 2-methylbutane-1,2,3-triol Chemical compound CC(O)C(C)(O)CO JUKWFOVSARANHP-UHFFFAOYSA-N 0.000 description 2
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- VYZKQGGPNIFCLD-UHFFFAOYSA-N 3,3-dimethylhexane-2,2-diol Chemical compound CCCC(C)(C)C(C)(O)O VYZKQGGPNIFCLD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 2
- ZRWNRAJCPNLYAK-UHFFFAOYSA-N 4-bromobenzamide Chemical compound NC(=O)C1=CC=C(Br)C=C1 ZRWNRAJCPNLYAK-UHFFFAOYSA-N 0.000 description 2
- CVSIGCPGGOVWDT-UHFFFAOYSA-N 4-methyl-6-propan-2-ylbenzene-1,3-diamine Chemical compound CC(C)C1=CC(C)=C(N)C=C1N CVSIGCPGGOVWDT-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
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- 125000006267 biphenyl group Chemical group 0.000 description 1
- NSPSPMKCKIPQBH-UHFFFAOYSA-K bismuth;7,7-dimethyloctanoate Chemical compound [Bi+3].CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O NSPSPMKCKIPQBH-UHFFFAOYSA-K 0.000 description 1
- ZOKIXFGMWAHYDQ-UHFFFAOYSA-N but-2-ene-2,3-diol Chemical compound CC(O)=C(C)O ZOKIXFGMWAHYDQ-UHFFFAOYSA-N 0.000 description 1
- LBXDJRWWKSGUOY-UHFFFAOYSA-N butane-1,4-diol;ethane-1,2-diol;hexanedioic acid Chemical compound OCCO.OCCCCO.OC(=O)CCCCC(O)=O LBXDJRWWKSGUOY-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- XXKOQQBKBHUATC-UHFFFAOYSA-N cyclohexylmethylcyclohexane Chemical compound C1CCCCC1CC1CCCCC1 XXKOQQBKBHUATC-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 1
- PNOXNTGLSKTMQO-UHFFFAOYSA-L diacetyloxytin Chemical compound CC(=O)O[Sn]OC(C)=O PNOXNTGLSKTMQO-UHFFFAOYSA-L 0.000 description 1
- 125000004427 diamine group Chemical group 0.000 description 1
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical group C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
- PYBNTRWJKQJDRE-UHFFFAOYSA-L dodecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O PYBNTRWJKQJDRE-UHFFFAOYSA-L 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- OYQYHJRSHHYEIG-UHFFFAOYSA-N ethyl carbamate;urea Chemical compound NC(N)=O.CCOC(N)=O OYQYHJRSHHYEIG-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 238000009775 high-speed stirring Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000004955 hydroxyethylimidazoles Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical class [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- QBYNWJVTTUAPCT-UHFFFAOYSA-N n,n'-bis(2-chlorophenyl)methanediamine Chemical group ClC1=CC=CC=C1NCNC1=CC=CC=C1Cl QBYNWJVTTUAPCT-UHFFFAOYSA-N 0.000 description 1
- CDZOGLJOFWFVOZ-UHFFFAOYSA-N n-propylaniline Chemical compound CCCNC1=CC=CC=C1 CDZOGLJOFWFVOZ-UHFFFAOYSA-N 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920003225 polyurethane elastomer Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000003340 retarding agent Substances 0.000 description 1
- 239000005336 safety glass Substances 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 1
- 229910000080 stannane Inorganic materials 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- AFNRRBXCCXDRPS-UHFFFAOYSA-N tin(ii) sulfide Chemical class [Sn]=S AFNRRBXCCXDRPS-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical compound NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 0.000 description 1
- 238000009849 vacuum degassing 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
-
- 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
- C08G18/4277—Caprolactone and/or substituted caprolactone
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
-
- 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
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/260,104 US20070100112A1 (en) | 2005-10-27 | 2005-10-27 | Polyurethane-urea elastomers |
| US11/260,104 | 2005-10-27 | ||
| PCT/US2006/041362 WO2007050542A1 (en) | 2005-10-27 | 2006-10-23 | Polyurethane-urea elastomers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2627322A1 CA2627322A1 (en) | 2007-05-03 |
| CA2627322C true CA2627322C (en) | 2014-12-30 |
Family
ID=37695304
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2627322A Expired - Fee Related CA2627322C (en) | 2005-10-27 | 2006-10-23 | Polyurethane-urea elastomers |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20070100112A1 (enExample) |
| EP (1) | EP1943283B1 (enExample) |
| JP (1) | JP5398263B2 (enExample) |
| KR (1) | KR101296535B1 (enExample) |
| CN (2) | CN101300283A (enExample) |
| BR (1) | BRPI0617862A2 (enExample) |
| CA (1) | CA2627322C (enExample) |
| ES (1) | ES2541423T3 (enExample) |
| RU (1) | RU2440376C9 (enExample) |
| TW (1) | TWI401265B (enExample) |
| WO (1) | WO2007050542A1 (enExample) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7964695B2 (en) | 2005-03-28 | 2011-06-21 | Albemarle Corporation | Chain extenders |
| AU2006332494A1 (en) * | 2005-12-30 | 2007-07-12 | Albemarle Corporation | Blends of diamines having reduced color |
| EP2102265A1 (en) | 2007-01-10 | 2009-09-23 | Albermarle Corporation | Formulations for reaction injection molding and for spray systems |
| EP2095832A1 (de) * | 2008-02-28 | 2009-09-02 | Bayer MaterialScience AG | Polyharnstoff-Systeme und deren Anwendung als postoperative Adhäsionsbarrieren, Filme und Verbundteile. |
| US7824288B2 (en) * | 2008-03-08 | 2010-11-02 | The Gates Corporation | Polyurethane power transmission belt |
| WO2010030544A1 (en) * | 2008-09-12 | 2010-03-18 | Dow Global Technologies Inc. | Coating formulations and compositions based on polyamines, polyols and polyisocyanates, and processes of preparing and of using the same |
| WO2011000771A2 (de) * | 2009-06-29 | 2011-01-06 | Basf Se | Poröse gele auf basis von aromatischem polyharnstoff |
| CN102472363A (zh) * | 2009-07-02 | 2012-05-23 | 盖茨公司 | 改善的用于齿动力传动带的织物和带 |
| US8372939B1 (en) | 2009-08-17 | 2013-02-12 | Polyplexx, Llc | Transparent polyurethanes |
| ES2381528T3 (es) * | 2009-12-12 | 2012-05-29 | Bayer Materialscience Ag | Sistema de material compuesto de adhesivo para cubrir, cerrar o pegar tejido celular |
| TWI465473B (zh) * | 2009-12-17 | 2014-12-21 | Albemarle Corp | 塗料組合物 |
| US20130240019A1 (en) * | 2012-03-14 | 2013-09-19 | Ppg Industries Ohio, Inc. | Coating-encapsulated photovoltaic modules and methods of making same |
| FR2990060B1 (fr) * | 2012-04-25 | 2015-02-27 | Commissariat Energie Atomique | Module solaire photovoltaique a architecture specifique |
| KR101448349B1 (ko) * | 2012-07-30 | 2014-10-08 | 코오롱인더스트리 주식회사 | 친환경 하이브리드 폴리우레아 조성물 |
| CN103289559A (zh) * | 2013-06-19 | 2013-09-11 | 江苏海晟涂料有限公司 | 一种高速列车专用涂料及其制备方法 |
| US9500445B2 (en) * | 2013-09-10 | 2016-11-22 | The United States Of America As Represented By The Secretary Of The Army | Multi-layer matrix composite having improved energy absorption, dissipation and shock wave mitigation capabilities |
| US20150166717A1 (en) | 2013-12-17 | 2015-06-18 | Bayer Materialscience Llc | Polyurethaneureas or polyureas |
| US9994666B2 (en) | 2013-12-17 | 2018-06-12 | Covestro Llc | Polyurethane/polyureas |
| WO2016006605A1 (ja) * | 2014-07-08 | 2016-01-14 | 三井化学株式会社 | 光学材料用重合性組成物およびその用途 |
| WO2016063884A1 (ja) * | 2014-10-21 | 2016-04-28 | 株式会社カネカ | 変性ポリアスパラギン酸エステルおよび硬化性樹脂組成物 |
| US9714363B2 (en) * | 2014-12-23 | 2017-07-25 | Super Skin Systems, Inc. | Silicone polyurea |
| US20160230041A1 (en) * | 2015-02-10 | 2016-08-11 | Milspray Llc | Transparent Structural Fortification Composite |
| US11059746B2 (en) | 2015-08-10 | 2021-07-13 | America as represented by the Secretary of the Army | Thermoplastic cycloaliphatic polyamide matrix resins for next-generation energy absorbing applications |
| CN105111404A (zh) * | 2015-08-27 | 2015-12-02 | 厦门明睐科技有限公司 | 一种聚氨酯弹性体的制备方法 |
| US11041043B2 (en) * | 2016-02-12 | 2021-06-22 | Evonik Operations Gmbh | Polycarbamide resins for metal coating applications |
| EP3433294B1 (en) * | 2016-03-22 | 2021-09-01 | Lubrizol Advanced Materials, Inc. | Melt processable thermoplastic polyurethane-urea elastomers |
| CN105713168B (zh) * | 2016-05-04 | 2018-08-28 | 中国科学院福建物质结构研究所 | 一种聚氨酯预聚体及其制备方法 |
| CN107573483B (zh) * | 2016-07-04 | 2022-06-17 | 科思创德国股份有限公司 | 可固化为聚硫氨酯的组合物、聚硫氨酯及其应用 |
| CN107686548B (zh) * | 2017-08-22 | 2021-12-10 | 山西省建筑科学研究院 | 水性纯聚脲的制备方法 |
| US20210002510A1 (en) * | 2018-02-11 | 2021-01-07 | Covestro Deutschland Ag | Coating composition |
| KR101943964B1 (ko) * | 2018-04-16 | 2019-01-30 | 윤정운 | 아민기를 함유한 이민계 조성물 및 그 제조방법, 아민기를 함유한 이민계 조성물을 포함하는 탄성체 수지 조성물 |
| US11492440B2 (en) * | 2018-07-27 | 2022-11-08 | Axalta Coating Systems Ip Co., Llc | Clearcoat compositions and methods of forming clearcoat compositions |
| KR101992921B1 (ko) * | 2018-12-28 | 2019-06-25 | 지혜경 | 폴리우레탄용 사슬 연장제 조성물 |
| US11827788B2 (en) | 2019-10-07 | 2023-11-28 | Covestro Llc | Faster cure polyaspartic resins for faster physical property development in coatings |
| CN110845685B (zh) * | 2019-12-12 | 2021-11-09 | 中国科学院长春应用化学研究所 | 一种修补汽车仪表板聚氨酯泡沫的聚天门冬氨酸酯聚脲基修补材料、其制备方法及修补方法 |
| CN110903457A (zh) * | 2019-12-12 | 2020-03-24 | 山东一诺威聚氨酯股份有限公司 | 一种用于制作快速脱模耐高温透明模特材料的聚氨酯弹性体及其制备方法 |
| EP4107202A1 (en) * | 2020-02-18 | 2022-12-28 | DDP Specialty Electronic Materials US, LLC | Polyurethane adhesive for bonding crosslinked rubber |
| KR102209863B1 (ko) * | 2020-05-12 | 2021-01-28 | 김진영 | 미끄럼방지 수지조성물 및 이를 이용한 미끄럼방지 포장재 |
| EP3913008A1 (de) * | 2020-05-20 | 2021-11-24 | Sika Technology Ag | Polyharnstoffzusammensetzung mit niedrigem gehalt an monomeren diisocyanaten |
| CN112341916A (zh) * | 2020-10-14 | 2021-02-09 | 西南科技大学 | 一种耐伽玛射线辐照聚脲材料及其制备方法 |
| CN114409864B (zh) * | 2020-10-28 | 2023-12-19 | 万华化学集团股份有限公司 | 聚氨酯或聚氨酯-脲的水分散体及其制备方法和用途 |
| JP7653296B2 (ja) * | 2021-05-07 | 2025-03-28 | アイシーケイ株式会社 | ２液常温硬化型手塗り用ウレタン防水材組成物 |
| KR102444382B1 (ko) * | 2021-05-25 | 2022-09-19 | 주식회사 빅스 | 우수한 세탁 내구성과 투습도를 갖는 섬유코팅용 폴리우레탄 수지의 제조방법 및 이를 이용한 섬유코팅 원단 |
| CN119331211B (zh) * | 2024-12-19 | 2025-06-03 | 山东一诺威聚氨酯股份有限公司 | 抗压、抗剪切的高速公路桥梁支座用聚氨酯材料及其制备方法 |
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| US6258917B1 (en) * | 1996-05-21 | 2001-07-10 | Simula, Inc. | Extrudable thermoplastic elastomeric urea-extended polyurethane |
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| US6174984B1 (en) * | 1999-06-14 | 2001-01-16 | Uniroyal Chemical Company, Inc. | Clear, resilient polyurethane elastomers |
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| JP3905409B2 (ja) * | 2002-04-10 | 2007-04-18 | タレックス光学工業株式会社 | 光学レンズ成型用ポリウレタン樹脂組成物および耐衝撃性合成樹脂レンズ |
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| US6939939B2 (en) * | 2003-02-24 | 2005-09-06 | Younger Mfg. | Polyurea/urethane optical material and method for making it |
-
2005
- 2005-10-27 US US11/260,104 patent/US20070100112A1/en not_active Abandoned
-
2006
- 2006-10-23 CN CNA2006800404827A patent/CN101300283A/zh active Pending
- 2006-10-23 ES ES06817312.9T patent/ES2541423T3/es active Active
- 2006-10-23 RU RU2008120558/04A patent/RU2440376C9/ru not_active IP Right Cessation
- 2006-10-23 WO PCT/US2006/041362 patent/WO2007050542A1/en not_active Ceased
- 2006-10-23 KR KR1020087009928A patent/KR101296535B1/ko not_active Expired - Fee Related
- 2006-10-23 CA CA2627322A patent/CA2627322C/en not_active Expired - Fee Related
- 2006-10-23 BR BRPI0617862-6A patent/BRPI0617862A2/pt not_active IP Right Cessation
- 2006-10-23 JP JP2008537853A patent/JP5398263B2/ja not_active Expired - Fee Related
- 2006-10-23 CN CN201310488712.8A patent/CN103554414A/zh active Pending
- 2006-10-23 EP EP06817312.9A patent/EP1943283B1/en not_active Not-in-force
- 2006-10-26 TW TW095139448A patent/TWI401265B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES2541423T3 (es) | 2015-07-20 |
| JP5398263B2 (ja) | 2014-01-29 |
| RU2008120558A (ru) | 2009-12-10 |
| JP2009513782A (ja) | 2009-04-02 |
| KR101296535B1 (ko) | 2013-08-13 |
| CN103554414A (zh) | 2014-02-05 |
| EP1943283B1 (en) | 2015-04-08 |
| TWI401265B (zh) | 2013-07-11 |
| WO2007050542A1 (en) | 2007-05-03 |
| RU2440376C9 (ru) | 2013-01-20 |
| RU2440376C2 (ru) | 2012-01-20 |
| US20070100112A1 (en) | 2007-05-03 |
| KR20080069973A (ko) | 2008-07-29 |
| TW200732364A (en) | 2007-09-01 |
| CA2627322A1 (en) | 2007-05-03 |
| CN101300283A (zh) | 2008-11-05 |
| BRPI0617862A2 (pt) | 2011-08-09 |
| EP1943283A1 (en) | 2008-07-16 |
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| EEER | Examination request | ||
| MKLA | Lapsed |
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