WO2022128763A1 - Mousse de polyuréthane et son procédé de production - Google Patents
Mousse de polyuréthane et son procédé de production Download PDFInfo
- Publication number
- WO2022128763A1 WO2022128763A1 PCT/EP2021/085137 EP2021085137W WO2022128763A1 WO 2022128763 A1 WO2022128763 A1 WO 2022128763A1 EP 2021085137 W EP2021085137 W EP 2021085137W WO 2022128763 A1 WO2022128763 A1 WO 2022128763A1
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- WO
- WIPO (PCT)
- Prior art keywords
- polyurethane foam
- polyol
- blowing agent
- adherend
- composition
- Prior art date
Links
- 229920005830 Polyurethane Foam Polymers 0.000 title claims abstract description 106
- 239000011496 polyurethane foam Substances 0.000 title claims abstract description 106
- 238000004519 manufacturing process Methods 0.000 title claims description 20
- 229920005862 polyol Polymers 0.000 claims abstract description 101
- 150000003077 polyols Chemical class 0.000 claims abstract description 101
- 239000000203 mixture Substances 0.000 claims abstract description 76
- 239000004604 Blowing Agent Substances 0.000 claims abstract description 54
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 44
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 44
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 24
- 125000000524 functional group Chemical group 0.000 claims abstract description 15
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 13
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 12
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 12
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 9
- 239000000853 adhesive Substances 0.000 abstract description 22
- 230000001070 adhesive effect Effects 0.000 abstract description 22
- 239000002994 raw material Substances 0.000 description 44
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 42
- 239000003054 catalyst Substances 0.000 description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 25
- 239000006260 foam Substances 0.000 description 24
- 238000005187 foaming Methods 0.000 description 22
- 239000004721 Polyphenylene oxide Substances 0.000 description 21
- 229920000570 polyether Polymers 0.000 description 21
- -1 polymethylene Polymers 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 239000002666 chemical blowing agent Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
- 229920001971 elastomer Polymers 0.000 description 8
- 239000005060 rubber Substances 0.000 description 8
- 239000011358 absorbing material Substances 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 7
- 229920005906 polyester polyol Polymers 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 229920002635 polyurethane Polymers 0.000 description 6
- 239000004814 polyurethane Substances 0.000 description 6
- 238000007142 ring opening reaction Methods 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 238000007259 addition reaction Methods 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 5
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 4
- 239000012790 adhesive layer Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000010419 fine particle Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- 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 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 125000005702 oxyalkylene group Chemical group 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 229920002857 polybutadiene Polymers 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 3
- 238000005829 trimerization reaction Methods 0.000 description 3
- LKLLNYWECKEQIB-UHFFFAOYSA-N 1,3,5-triazinane Chemical compound C1NCNCN1 LKLLNYWECKEQIB-UHFFFAOYSA-N 0.000 description 2
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 2
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 238000012644 addition polymerization Methods 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000013016 damping Methods 0.000 description 2
- 239000008121 dextrose Substances 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 229940043276 diisopropanolamine Drugs 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 239000011810 insulating material Substances 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- CDOOAUSHHFGWSA-OWOJBTEDSA-N (e)-1,3,3,3-tetrafluoroprop-1-ene Chemical compound F\C=C\C(F)(F)F CDOOAUSHHFGWSA-OWOJBTEDSA-N 0.000 description 1
- LDTMPQQAWUMPKS-OWOJBTEDSA-N (e)-1-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)\C=C\Cl LDTMPQQAWUMPKS-OWOJBTEDSA-N 0.000 description 1
- DMUPYMORYHFFCT-UPHRSURJSA-N (z)-1,2,3,3,3-pentafluoroprop-1-ene Chemical compound F\C=C(/F)C(F)(F)F DMUPYMORYHFFCT-UPHRSURJSA-N 0.000 description 1
- ZUAQTIHDWIHCSV-UPHRSURJSA-N (z)-1,2,3,3-tetrafluoroprop-1-ene Chemical compound F\C=C(/F)C(F)F ZUAQTIHDWIHCSV-UPHRSURJSA-N 0.000 description 1
- NLOLSXYRJFEOTA-UHFFFAOYSA-N 1,1,1,4,4,4-hexafluorobut-2-ene Chemical compound FC(F)(F)C=CC(F)(F)F NLOLSXYRJFEOTA-UHFFFAOYSA-N 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-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
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- ZGDSDWSIFQBAJS-UHFFFAOYSA-N 1,2-diisocyanatopropane Chemical compound O=C=NC(C)CN=C=O ZGDSDWSIFQBAJS-UHFFFAOYSA-N 0.000 description 1
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 1
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- ADQQGJLCEXHTRW-UHFFFAOYSA-N 1-(dimethylamino)hexan-1-ol Chemical compound CCCCCC(O)N(C)C ADQQGJLCEXHTRW-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 description 1
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
- IVJXXQSXKSRPIL-UHFFFAOYSA-N 2,4-bis[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC=C(O)C(CN(C)C)=C1 IVJXXQSXKSRPIL-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 1
- QHTUMQYGZQYEOZ-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)ethanol Chemical compound CN1CCN(CCO)CC1 QHTUMQYGZQYEOZ-UHFFFAOYSA-N 0.000 description 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- YSAANLSYLSUVHB-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]ethanol Chemical compound CN(C)CCOCCO YSAANLSYLSUVHB-UHFFFAOYSA-N 0.000 description 1
- LSYBWANTZYUTGJ-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl-methylamino]ethanol Chemical compound CN(C)CCN(C)CCO LSYBWANTZYUTGJ-UHFFFAOYSA-N 0.000 description 1
- WZCQDYGWGDYQNC-UHFFFAOYSA-N 2-chloro-1,1,1,3,4,4,4-heptafluorobut-2-ene Chemical compound FC(F)(F)C(F)=C(Cl)C(F)(F)F WZCQDYGWGDYQNC-UHFFFAOYSA-N 0.000 description 1
- JRENXZBKMHPULY-UHFFFAOYSA-N 2-chloro-1,1,1,4,4,4-hexafluorobut-2-ene Chemical compound FC(F)(F)C=C(Cl)C(F)(F)F JRENXZBKMHPULY-UHFFFAOYSA-N 0.000 description 1
- MGLZGLAFFOMWPB-UHFFFAOYSA-N 2-chloro-1,4-phenylenediamine Chemical compound NC1=CC=C(N)C(Cl)=C1 MGLZGLAFFOMWPB-UHFFFAOYSA-N 0.000 description 1
- OQISUJXQFPPARX-UHFFFAOYSA-N 2-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C(Cl)=C OQISUJXQFPPARX-UHFFFAOYSA-N 0.000 description 1
- SVNWKKJQEFIURY-UHFFFAOYSA-N 2-methyl-1-(2-methylpropyl)imidazole Chemical compound CC(C)CN1C=CN=C1C SVNWKKJQEFIURY-UHFFFAOYSA-N 0.000 description 1
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 description 1
- FIROAKDNSCQSTG-UHFFFAOYSA-N 3,3-dichloro-3-fluoroprop-1-ene Chemical compound FC(Cl)(Cl)C=C FIROAKDNSCQSTG-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- OMHOXRVODFQGCA-UHFFFAOYSA-N 4-[(4-amino-3,5-dimethylphenyl)methyl]-2,6-dimethylaniline Chemical compound CC1=C(N)C(C)=CC(CC=2C=C(C)C(N)=C(C)C=2)=C1 OMHOXRVODFQGCA-UHFFFAOYSA-N 0.000 description 1
- GZGKPOCYYNKGCV-UHFFFAOYSA-N 5-(dimethylamino)-3-methylpentan-1-ol Chemical compound OCCC(C)CCN(C)C GZGKPOCYYNKGCV-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08G2110/0058—≥50 and <150kg/m3
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- 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
- C08G2350/00—Acoustic or vibration damping material
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- 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
- C08G2380/00—Tyres
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2201/00—Foams characterised by the foaming process
- C08J2201/02—Foams characterised by the foaming process characterised by mechanical pre- or post-treatments
- C08J2201/026—Crosslinking before of after foaming
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2203/00—Foams characterized by the expanding agent
- C08J2203/16—Unsaturated hydrocarbons
- C08J2203/162—Halogenated unsaturated hydrocarbons, e.g. H2C=CF2
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2205/00—Foams characterised by their properties
- C08J2205/08—Semi-flexible foams
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2205/00—Foams characterised by their properties
- C08J2205/10—Rigid foams
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2303/00—Characterised by the use of starch, amylose or amylopectin or of their derivatives or degradation products
- C08J2303/14—Amylose derivatives; Amylopectin derivatives
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
Definitions
- the present invention relates to a polyurethane foam and a method for producing a polyurethane foam, and particularly relates to a polyurethane foam having improved adhesive strength with an adherend.
- Sound absorbing materials, sound insulating materials, damping materials and the like are known as sound suppressors that suppress generation of sound, and polyurethane materials and the like are used.
- Patent Literature 1 JP 2018-70148 A (Patent Literature 1) describes a resonance noise reducing tire comprising an adhesive layer applied to an inside of an inner liner and a sound absorbing material layer attached to the adhesive layer, in which the adhesive layer comprises a polyether containing an alkoxysilane substituent in a main chain not in a terminal, and a polyurethane foam is used for the sound absorbing material layer. Patent Literature 1 describes that it is possible to provide a stable resonance noise reducing tire without detachment of the sound absorbing material even for heat generation and deformation during running by applying an adhesive layer having improved elasticity and adhesive strength between the inner liner of the tire and the sound absorbing material layer.
- Patent Literature 2 JP 2012-117039 A (Patent Literature 2) describes a polyurethane foam obtained by reacting a diol with a diisocyanate, in which a polyether-based diol and a polyester-based diol are mixed and used as the diol.
- Patent Literature 2 describes that it is an object of the invention to improve a disadvantage that an internal space of a pneumatic tire is easily collapsed due to low tensile force and rigidity, and describes that it is possible to provide a pneumatic tire with reduced resonance noise of the internal space and comfortable ride feeling by applying the above polyurethane foam as a sound absorbing material.
- Patent Literature 3 describes a pneumatic tire with a sound suppressor comprising a pneumatic tire and a sound suppressor made of a porous resin foam arranged on an inner surface of a tread of the pneumatic tire, in which the sound suppressor comprises one annular body that extends continuously in the tire circumferential direction, and core density of the sound suppressor, overall density, and maximum height from the inner surface of the tread are specified in specific ranges, and a polyurethane foam is used as the porous resin foam.
- Patent Literature 3 describes that it is possible to provide a pneumatic tire with a sound suppressor that can suppress damage to the sound suppressor and improve sound suppression performance by applying such a sound suppressor to a pneumatic tire.
- Patent Literature 1 JP 2018-70148 A
- Patent Literature 2 JP 2012-117039 A
- Patent Literature 3 JP 2020-19390 A
- the sound suppressor is also often arranged in an environment where it is easily peeled off due to vibration or the like, and there is a problem with durability, thus it is required to improve the adhesive strength with the adherend.
- Patent Literature 1 a method of using an adhesive for improving the adhesive strength is known, but it cannot be said that sufficient studies have been made on improving adhesiveness of the sound suppressor itself.
- an object of the present invention is to provide a polyurethane foam having improved adhesive strength with an adherend.
- the present inventors have intensively studied in order to solve the above problem, and found that, in the production of a flexible or semirigid polyurethane foam, the adhesive strength of the obtained polyurethane foam with an adherend can be improved by using a physical blowing agent as a blowing agent, and sufficient adhesive strength can be exhibited even if it is applied directly to the adherend.
- a first aspect of the present invention is a flexible or semirigid polyurethane foam for direct adhesion to an adherend, in which the polyurethane foam is obtained from a composition comprising a polyisocyanate, a polyol and a physical blowing agent, and in which the composition comprises a crosslinking agent having a functional group number of not less than 2 and a molecular weight of 60 to 1000 g/mol in an amount of not less than 3 parts by mass based on 100 parts by mass of the polyol.
- the foam is obtained from a composition which does not contain water as a blowing agent, i.e., the composition contains water at most in residual amounts, for example from other components such as a polyol component.
- the composition is essentially free of water, i.e., the composition contains water only in trace amounts, such as 0.01 parts by mass based on 100 parts by mass of the polyol, for example from other components such as a polyol component.
- the composition does not contain any water.
- the physical blowing agent has a boiling point of at least 15 °C.
- the physical blowing agent is at least one selected from the group consisting of hydrochlorofluorocarbons, hydrofluorocarbons, hydrofluoroolefms, heptane, hexane, pentane, and cyclopentane.
- the composition comprises a physical blowing agent having a boiling point of at least 15 °C and does not contain water as a blowing agent; or the composition comprises a physical blowing agent having a boiling point of at least 15 °C and is essentially free of water; or the composition comprises a physical blowing agent having a boiling point of at least 15 °C and does not contain any water.
- the foam is obtained from a composition comprising a physical blowing agent which is at least one selected from the group consisting of hydrochlorofluorocarbons, hydrofluorocarbons, hydrofluoroolefms, heptane, hexane, pentane, and cyclopentane, and the composition does not contain water as a blowing agent; or the foam is obtained from a composition comprising a physical blowing agent which is at least one selected from the group consisting of hydrochlorofluorocarbons, hydrofluorocarbons, hydrofluoroolefms, heptane, hexane, pentane, and cyclopentane, and the composition is essentially free of water; or the foam is obtained from a composition comprising a physical blowing agent which is at least one selected from the group consisting of hydrochlorofluorocarbons, hydrofluorocarbons, hydrofluoroolefms, heptane, hexane, pen
- residual amounts refer to amounts equal to or less than 0.1 parts by mass based on 100 parts by mass of the polyol.
- trace amounts refer to amounts equal to or less than 0.01 parts by mass based on 100 parts by mass of the polyol.
- the adherend is a pneumatic tire.
- a second aspect of the present invention is a method for producing a polyurethane foam, in which the method comprises a step of directly applying a composition comprising a polyisocyanate, a polyol and a physical blowing agent to an adherend to form a flexible or semirigid polyurethane foam.
- One aspect of the present invention is a polyurethane foam.
- Foam and non-foam are known as polyurethane products, but one embodiment of the present invention relates to a polyurethane foam, from the viewpoint of a sound suppressor for reducing a problematic sound in a place where it is used.
- the polyurethane foam is classified into a flexible foam, a semirigid foam and a rigid foam, and the polyurethane foam of the present invention is preferably a flexible or semirigid polyurethane foam.
- the “flexible polyurethane foam” refers to a urethane foam with a product density of less than 100 kg/m 3 , which is molded using a compounded polyol containing not less than 50% by mass of a polyol having a hydroxyl value of not more than 56 mg KOH/g.
- the “semirigid polyurethane foam” refers to a urethane foam with a product density of not less than 100 kg/m 3 , which is molded using a compounded polyol containing not less than 50% by mass of a polyol having a hydroxyl value of not more than 56 mg KOH/g and not less than 5% by mass of a crosslinking agent having a hydroxyl value of not less than 112 mg KOH/g.
- the “rigid polyurethane foam” refers to a urethane foam, which is molded using a compounded polyol containing not less than 50% by mass of a polyol having a hydroxyl value of 300 to 500 mg KOH/g.
- the density here is an apparent overall density, and can be measured according to JIS K 7222: 2005 as described later.
- the polyurethane foam of the present invention is obtained from a composition comprising a polyisocyanate, a polyol and a physical blowing agent.
- a physical blowing agent as a blowing agent.
- the adhesive strength of the polyurethane foam to the adherend can be improved.
- a chemical blowing agent when used, the adhesion area of the polyurethane foam to the adherend is small because air bubbles are present even in the vicinity of the adhesion interface with the adherend. Therefore, the use of the chemical blowing agent does not provide an effect of improving the adhesive strength as exhibited by the use of the physical blowing agent.
- a foaming reaction using water or the like as a chemical blowing agent a urea bond is formed by a reaction with polyisocyanate. Therefore, when water or the like is used, there is also a problem that it is easily peeled off due to cohesive failure of urea which is a hard segment.
- the polyurethane foam of the present invention since it is possible to provide a polyurethane foam having improved adhesive strength with an adherend, sufficient adhesive strength can be exhibited even if the polyurethane foam is directly applied to the adherend. Therefore, the polyurethane foam of the present invention is preferred as a polyurethane foam for direct adhesion to an adherend.
- the phrase “direct adhesion to an adherend” means that a polyurethane foam is directly adhered to an adherend, and in a more specific embodiment, the polyurethane raw material is foamed by directly applying or injecting the polyurethane raw material to an adherend, whereby a polyurethane foam is directly adhered to an adherend.
- adhesion using means such as an adhesive or a jig for adhering a polyurethane foam and an adherend is excluded from the “direct adhesion to an adherend”.
- the polyurethane foam of the present invention has a peel strength from an adherend of preferably not less than 55 N, and further preferably not less than 70 N.
- the upper limit is not particularly limited, for example, the peel strength from an adherend is not more than 500 N, and preferably not more than 200 N.
- the peel strength of the polyurethane foam to an adherend can be improved by appropriately adjusting the type and amount of blowing agent (specifically, by using a physical blowing agent and increasing the amount of physical blowing agent when used in combination with a chemical blowing agent).
- the peel strength of the polyurethane foam to an adherend is a value measured by the following procedures.
- a reaction mixture solution (raw material composition described later) is applied to a flat rubber sheet and foamed to form a foam with a width of not less than 10 mm.
- a notch is made in the cured polyurethane foam with a width of 10 mm perpendicular to the rubber sheet.
- the polyurethane foam of the present invention uses a remaining portion (core portion) cut from a surface layer portion of the polyurethane foam to a thickness of not less than 2 mm, and has a thickness of 20 mm and an average value of normal incidence sound absorption coefficient at 100 to 5000 Hz of preferably not less than 0.4, and further preferably not less than 0.5.
- the average value of the normal incidence sound absorption coefficient at 100 to 5000 Hz is not more than 1.0.
- the normal incidence sound absorption coefficient of the polyurethane foam is a value measured according to JIS A 1405-2: 2007.
- the incident direction of the sound to be measured was from the upper side in the foaming direction.
- the polyurethane foam of the present invention preferably has an apparent overall density of 30 to 150 kg/m 3 , further preferably 30 to 105 kg/m 3 or 40 to 120 kg/m 3 , more preferably 40 to 105 kg/m 3 , and particularly preferably 50 to 105 kg/m 3 or 50 to 90 kg/m 3 .
- the density of polyurethane foam is measured according to JIS K 7222: 2005.
- composition used for forming the polyurethane foam of the present invention is a composition comprising a polyisocyanate, a polyol and a physical blowing agent, as described above.
- the composition used for forming the polyurethane foam is also referred to as a raw material composition.
- the polyisocyanate used in the raw material composition is a compound having a plurality of isocyanate groups. Examples thereof include aliphatic, alicyclic, aromatic or araliphatic polyisocyanates, and modified products of these polyisocyanates are also included.
- polyisocyanates having a structure such as uretdione, isocyanurate, urethane, urea, allophanate, biuret, carbodiimide, iminooxadiazinedione, oxadiazinetrione, or oxazolidone.
- polyisocyanate an isocyanate group-containing prepolymer obtained by reacting a polyol with a polyisocyanate may be used.
- the polyisocyanates may be used alone or in combination of two or more.
- examples of the aromatic polyisocyanate include phenylene diisocyanate, tolylene diisocyanate, xylylene diisocyanate, diphenylmethane diisocyanate, dimethyldiphenylmethane diisocyanate, triphenylmethane triisocyanate, naphthalene diisocyanate, polymethylene polyphenyl polyisocyanate, and the like.
- Examples of the alicyclic polyisocyanate include cyclohexylene diisocyanate, methylcyclohexylene diisocyanate, isophorone diisocyanate, dicyclohexylmethane diisocyanate, dimethyldicyclohexylmethane diisocyanate, and the like.
- Examples of the aliphatic polyisocyanate include methylene diisocyanate, ethylene diisocyanate, propylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, and the like.
- the polyisocyanate preferably has an isocyanate group content of 20 to 40% by mass, and further preferably 23 to 35% by mass.
- the isocyanate group content is determined according to JIS K 1603-1: 2007.
- the amount of polyisocyanate can be shown by, for example, an isocyanate index.
- the isocyanate index is preferably 70 to 150, more preferably 80 to 120, and further preferably 90 to 110.
- the isocyanate index refers to a value obtained by multiplying 100 by the ratio of the isocyanate group of the polyisocyanate to the total active hydrogen that reacts with an isocyanate group such as polyol.
- the polyol used in the raw material composition is a compound having a plurality of hydroxyl groups, and is preferably a polymeric polyol.
- Specific examples of the polyol include polyether polyols, polyester polyols, polycarbonate polyols, polylactone polyols, polybutadiene polyols, polymer polyols, Mannich polyols, and the like.
- the amount of polyol is appropriately adjusted according to the amount of polyisocyanate, and is, for example, 30 to 70 parts by mass based on 100 parts by mass of the raw material composition.
- the polyols may be used alone or in combination of two or more.
- polyether polyol examples include polyoxyalkylene-based polyols, and the poly oxyalkylene-based polyols can be produced by subjecting an alkylene oxide to a ringopening addition reaction, using a compound having two or more hydroxyl groups, primary amino groups, secondary amino groups, and other active hydrogen-containing groups and the like as starting materials.
- the starting raw materials for the polyoxyalkylene-based polyols include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, 1,4- butanediol, 1,6-hexanediol, neopentyl glycol, glycerin, trimethylolpropane, pentaerythritol, diglycerin, mannose, sucrose, fructose, dextrose and sorbitol, alkanolamines such as ethanolamine, diethanolamine, triethanolamine and methyldiethanolamine, polyvalent amines such as ethylenediamine, tolylenediamine, diethyltoluenediamine, 1,3-propanediamine, 1,6-hexanediamine, isophoronediamine, diethylenetriamine and triethylenepentaamine, polyhydric phenols such as bisphenol A, bisphenol F, resorcinol and hydroquinone,
- alkylene oxide to be subjected to the ring -opening addition reaction in the production of the poly oxyalkylene-based polyol examples include ethylene oxide, propylene oxide, 1,2- butylene oxide, 2,3-butylene oxide, styrene oxide and the like, and these alkylene oxides may be used alone or in combination of two or more.
- polymer polyol examples include those in which polymer fine particles such as polyacrylonitrile fine particles and polystyrene fine particles are dispersed in a polyoxyalkylene- based polyol, and the like.
- Polymer polyol is a kind of polyether polyol because it contains a poly oxyalkylene-based polyol.
- the Mannich polyol can be produced by subjecting phenols, aldehydes, alkanolamines and the like to a condensation reaction, and further, carrying out a ring-opening addition reaction of an alkylene oxide such as ethylene oxide or propylene oxide as necessary.
- Mannich polyol is a kind of polyether polyol because it has a plurality of ether bonds in a molecule.
- polyether polyols examples include polyoxyalkylene-based polyols such as (di)ethylene glycol-based polyether polyols, (di)propylene glycol-based polyether polyols, (di)glycerin-based polyether polyols, trimethylolpropane-based polyether polyols, pentaerythritol- based polyether polyols, sucrose-based polyether polyols, dextrose-based polyether polyols, sorbitol-based polyether polyols, mono(di,tri)ethanolamine-based polyether polyols, ethylenediamine-based polyether polyols, tolylenediamine-based polyether polyols, and bisphenol A-based polyether polyols, obtained by an addition reaction of ethylene oxide and/or propylene oxide, polymer polyols in which polymer fine particles are dispersed in polyoxyalkylene-based polyols, Mannich
- the polyester polyol can be produced by adjusting production conditions of polyester, and examples thereof include polyester polyols having hydroxyl groups at least at both ends of the main chain, and more specifically, linear polyester polyols, slightly branched polyester polyols, and the like.
- the polyester polyols can be prepared by known methods using aliphatic, cycloaliphatic or aromatic dicarboxylic acids, a diol, and optionally polycarboxylic acids and/or a trifunctional or higher functional polyol.
- Polylactone polyol is a homopolymer or copolymer of lactone, and examples thereof include polylactones having hydroxyl groups at least at both ends of the main chain. Specifically, it can be produced by subjecting a lactone such as s-caprolactonc. [3-butyrolactone, y-butyrolactone, y-valerolactone or 5-valerolactone to a ring-opening addition reaction, using a compound having two or more active hydrogen-containing groups as described above for the polyoxyalkylene-based polyol as a starting material.
- Polylactone polyol is a kind of polyester polyol because it has a plurality of ester bonds in a molecule.
- the polycarbonate polyol can be produced by adjusting production conditions of polycarbonate, and examples thereof include polycarbonates having hydroxyl groups at least at both ends of the main chain, and the like.
- examples of the polybutadiene polyol include polybutadiene having hydroxyl groups at least at both ends of the main chain, and the like.
- the polyol has a hydroxyl value of preferably 28 to 112 mg KOH/g, and more preferably 28 to 56 mg KOH/g.
- the hydroxyl value is the number of mg of potassium hydroxide required to neutralize free hydroxyl groups in 1 g of a sample after complete acetylation with carboxylic acid anhydride (for example, phthalic anhydride or acetic anhydride) (see JIS K 1557 2007).
- carboxylic acid anhydride for example, phthalic anhydride or acetic anhydride
- the polyol has a molecular weight of preferably 1500 to 12000 g/mol, preferably 2000 to 8000 g/mol, and more preferably 2000 to 7000 g/mol.
- the polyol when the polyol is a polymer, its molecular weight can be measured as a polystyrene equivalent number average molecular weight measured by gel permeation chromatography.
- the polyol has a functional group number (fin) of preferably 2 to 8, more preferably 2 to
- the functional group number (fh) per molecule of polyol can be calculated by the following calculation formula from the hydroxyl value (OHV) and the number average molecular weight (Mn) of the polyol.
- fii Mn(g/mol) x 0HV(mg KOH/g)/56100
- the physical blowing agent used in the raw material composition include fluorocarbons such as hydrochlorofluorocarbons (HCFCs) and hydrofluorocarbons (HFCs), hydrofluoroolefins (HFOs), hydrocarbons such as heptane, hexane, pentane and cyclopentane, carbon dioxide, and the like.
- fluorocarbons such as hydrochlorofluorocarbons (HCFCs) and hydrofluorocarbons (HFCs), hydrofluoroolefins (HFOs), hydrocarbons such as heptane, hexane, pentane and cyclopentane, carbon dioxide, and the like.
- hydrofluoroolefins and cyclopentane are preferable from the viewpoint of improving adhesive strength with the adherend.
- the blowing agents may be used alone or in combination of two or more.
- the raw material composition preferably comprises cyclopentane as a physical blowing agent.
- the raw material composition preferably comprises a hydrofluoroolefin as a physical blowing agent.
- Hydrofluoroolefins are blowing agents that are preferably used as physical blowing agents that do not fall into the category of fluorocarbons.
- HFOs are olefin compounds containing a fluorine atom, and also include compounds further containing a halogen atom (for example, a chlorine atom) other than fluorine.
- HCFOs hydrochlorofluoroolefins
- HFOs and HCFOs may be distinguished, in the present specification, HFOs include HCFOs as described above.
- the hydrofluoroolefin preferably has 2 to 5 carbon atoms and preferably has 3 to 7 fluorine atoms.
- the molecular weight of the HFO is preferably 100 to 200 g/mol.
- Specific examples of the HFO include 1,2,3,3,3-pentafluoropropene, 1,3,3,3-tetrafluoropropene, 2, 3,3,3- tetrafluoropropene, 1,2,3,3-tetrafluoropropene, 3,3,3-trifluoropropene, 1, 1,1, 4,4,4- hexafluorobutene, l-chloro-3,3,3-trifluoropropene, 2-chloro-3,3,3-trifluoropropene, 3,3-dichloro-3- fluoropropene, 2-chloro- 1,1,1 ,4,4,4-hexafluorobutene, 2-chloro- 1,1, 1 ,3,4,4,4-heptafluorobut
- the amount of the physical blowing agent is preferably 0.5 to 15 parts by mass, and further preferably 3 to 12 parts by mass, based on 100 parts by mass of the raw material composition.
- the raw material composition may comprise a chemical blowing agent together with a physical blowing agent.
- the chemical blowing agent include water, carboxylic acids such as formic acid and acetic acid, and the like.
- the amount of the chemical blowing agent is small even when the chemical blowing agent is used.
- the amount of chemical blowing agent is less than 0.5 parts by mass based on 100 parts by mass of the raw material composition.
- the raw material composition preferably comprises a crosslinking agent.
- a crosslinking agent a compound having a functional group number of not less than 2 and a molecular weight of 60 to 1000 g/mol is preferable.
- the functional group of the crosslinking agent usually refers to a group that is reactive with isocyanate.
- the crosslinking agent has an average functional group number of preferably not less than 2, and more preferably 2 to 3.
- the crosslinking agent has a molecular weight of preferably 60 to 1000 g/mol, and more preferably 60 to 400 g/mol.
- the crosslinking agent include an amine crosslinking agent and a crosslinking agent having a hydroxyl group.
- the crosslinking agent also includes a compound having a plurality of hydroxyl groups, it may correspond to a polyol, but in the present specification, the crosslinking agent is a component that is distinguished from the polyol. Therefore, the polyol in the present specification is a compound having a plurality of hydroxyl groups, but it is also possible to express as a component from which the compound having a functional group number of not less than 2 and a molecular weight of 60 to 1000 g/mol is excluded. [0055]
- the amount of the crosslinking agent is preferably not less than 3 parts by mass, and further preferably 5 to 25 parts by mass based on 100 parts by mass of the polyol.
- the crosslinking agents may be used alone or in combination of two or more.
- amine crosslinking agent examples include aliphatic amines, aromatic amines, and alicyclic amines having a primary or secondary amino group, and the like.
- an aliphatic amine compound having a primary or secondary amino group include alkylamine compounds such as ethylenediamine, m-xylenediamine, 1,4-diaminohexane, butylamine, hexamethylenediamine, diethylenetriamine, triethylenetetramine and dimethylaminopropylamine, alkanolamine compounds such as ethanolamine, N-methylethanolamine, diethanolamine, triethanolamine, isopropanolamine, and diisopropanolamine, hydroxylamine, and the like.
- an aromatic amine compound having a primary or secondary amino group examples include 3,5- diethyl-2,4 (or 2,6)-diaminotoluene (DETDA), 2-chloro-p-phenylenediamine, 3,5-dimethylthio-2,4 (or 2,6)-diaminotoluene, l-trifluoromethyl-3, 5 -diaminobenzene, l-trifluoromethyl-4-chloro-3,5- diaminobenzene, 2,4-toluenediamine, 2,6-toluenediamine, bis(3, 5 -dimethyl -4- aminophenyl)methane, 4,4-diaminodiphenylmethane, and the like.
- DETDA 3,5- diethyl-2,4 (or 2,6)-diaminotoluene
- 2-chloro-p-phenylenediamine 3,5-dimethylthio-2,4 (or 2,6)-diaminotol
- an alicyclic amine compound having a primary or secondary amino group include cycloalkanes having two or more amino groups and/or aminoalkyl groups such as l,3-bis(aminomethyl)cyclohexane and isophoronediamine .
- crosslinking agent having a hydroxyl group examples include ethylene glycol, polyethylene glycol, 1,4-butanediol, neopentyl glycol, 1,6-hexanediol, diethylene glycol, triethylene glycol, dipropylene glycol, triethanolamine, glycerin, sorbitol, sucrose, pentaerythritol, N-alkyldiethanol, bisphenol A-alkylene oxide adducts, glycerin-alkylene oxide adducts, trimethylolpropane-alkylene oxide adducts, pentaerythritol-alkylene oxide adducts, sorbitolalkylene oxide adducts, sucrose-alkylene oxide adducts, aliphatic amine-alkylene oxide adducts, alicyclic amine-alkylene oxide adducts, heterocyclic polyamine-alkylene oxide
- the raw material composition may comprise a catalyst.
- the catalyst include catalysts (foaming catalysts) that promote a reaction between water and polyisocyanate, catalysts (resinification catalysts) that promote a reaction between polyol and polyisocyanate, catalysts (trimerization catalysts) that promote a trimerization reaction of polyisocyanate (that is, formation of an isocyanurate ring), and the like.
- the raw material composition preferably comprises a resinification catalyst.
- foaming catalyst examples include dimorpholine-2,2-diethyl ether, N,N,N',N",N"- pentamethyldiethylenetriamine, bis(dimethylaminoethyl)ether, 2-(2-dimethylaminoethoxy)ethanol, N,N,N'-trimethyl-N'-hydroxyethyl bisaminoethyl ether, and the like.
- resinification catalyst examples include amine catalysts such as triethylenediamine, N,N-dimethylcyclohexylamine, N,N,N',N'-tetramethylethylenediamine,
- amine carbonates synthesized by adding carbonic acid and amine carboxylates synthesized by adding a carboxylic acid such as formic acid or acetic acid may be used.
- trimerization catalyst examples include aromatic compounds such as 2,4,6- tris(dialkylaminoalkyl)hexahydro-S-triazine, l,3,5-tris(N,N-dimethylaminopropyl)hexahydro-S- triazine, 2,4,6-tris(dimethylaminomethyl)phenol and 2,4-bis(dimethylaminomethyl)phenol, alkali metal carboxylates such as potassium acetate, potassium 2-ethylhexanoate and potassium octylate, quaternary ammonium salts of carboxylic acid, or other onium salts, and the like.
- aromatic compounds such as 2,4,6- tris(dialkylaminoalkyl)hexahydro-S-triazine, l,3,5-tris(N,N-dimethylaminopropyl)hexahydro-S- triazine, 2,4,6-tris(dimethylaminomethyl)
- the amount of the catalyst is, for example, 0.1 to 5 parts by mass, and preferably 0.5 to 2.5 parts by mass, based on 100 parts by mass of the raw material composition.
- the catalysts may be used alone or in combination of two or more.
- the raw material composition may comprise a foam stabilizer.
- the foam stabilizer is preferably a surfactant.
- the surfactants include ionic surfactants such as anionic, cationic and amphoteric, and nonionic surfactants, but nonionic surfactants are preferred. Also, specific examples preferably include silicone-based surfactants and fluorine-based surfactants.
- the amount of the foam stabilizer is preferably 0.3 to 5 parts by mass based on 100 parts by mass of the polyol. The foam stabilizers may be used alone or in combination of two or more.
- additives such as flame retardants, coloring agents, fillers, antioxidants, ultraviolet absorbers, heat stabilizers, light stabilizers, plasticizers, fungicides, antibacterial agents, solvents, viscosity-reducing agents, depressurizing agents and separation inhibitors may be appropriately compounded as necessary.
- the raw material composition can be prepared by mixing various components appropriately selected as necessary.
- the raw material composition can be prepared by mixing a polyol component comprising a polyol and a polyisocyanate component composed of a polyisocyanate.
- the physical blowing agent may be contained in the polyol component or the polyisocyanate component, or may be compounded when the polyol component and the polyisocyanate component are mixed.
- the polyol component comprises a polyol, usually comprises a crosslinking agent, a blowing agent, a foam stabilizer and a catalyst, and may comprise additional additives.
- the polyisocyanate component is composed of polyisocyanate, but may further comprise additives such as blowing agents and flame retardants.
- the raw material composition is preferably adjusted so that liquid dripping length thereof exceeds 300 mm.
- liquid dripping length of the raw material composition exceeds 300 mm, wettability of the raw material composition to the adherend is improved, which is advantageous for improving the adhesive strength.
- the liquid dripping length of the raw material composition is measured by the following measurement method.
- An acrylic plate is placed vertically at a position 10 cm away from a discharge position of a high-pressure foaming machine, and the raw material composition is discharged from the high-pressure foaming machine to the acrylic plate at a speed of 120 g/sec for 0.2 seconds to form a discharged product on the acrylic plate.
- Five minutes after the discharge a length from the highest point to the lowest point in the vertical direction of the discharged product on the acrylic plate is measured as the liquid dripping length.
- the polyurethane foam of the present invention can be formed by foaming the above- mentioned raw material composition. Since the raw material composition contains a polyol and a polyisocyanate, it is possible to proceed the reaction by mixing both to form a polyurethane foam.
- the temperature at the time of forming the polyurethane foam is preferably 10 to 30°C.
- the foaming method of the polyurethane foam is not particularly limited, and known foaming means, for example, hand mixing foaming, simple foaming, injection method, floss injection method, spray method, and the like can be used.
- the molding method of the polyurethane foam is not particularly limited, and known molding means, for example, mold molding, slab molding, laminate molding, in-situ foam molding, and the like can be used.
- the polyurethane foam of the present invention is preferred as a product that suppresses generation of sound, like a sound suppressor such as a sound absorbing material, a sound insulating material, or a damping material.
- Examples of the adherend of the polyurethane foam of the present invention include pneumatic tires, vehicle bodies (automobiles and the like) or parts thereof (wheels, especially, rims and the like), heavy machinery, generators, OA equipment, home appliances, building materials, and the like.
- vehicle body parts include vehicle body skeleton members, such as pillars, sills (rocker panels), chassis rails, and the like.
- the polyurethane foam of the present invention is arranged on an inner surface (a surface on the side of space that traps air) of the pneumatic tire, particularly on the inner surface of a tread part.
- the polyurethane foam of the present invention may be arranged on the wheel side, preferably on the rim surface, not on the tire.
- Another aspect of the present invention is a method for producing a polyurethane foam.
- the method for producing a polyurethane of the present invention comprises directly applying a composition comprising a polyisocyanate, a polyol and a physical blowing agent to an adherend to form a flexible or semirigid polyurethane foam.
- the adhesive strength of the obtained polyurethane foam with an adherend can be improved by using a physical blowing agent as a blowing agent.
- the method for producing a polyurethane foam of the present invention is also referred to as the production method of the present invention.
- composition comprising a polyisocyanate, a polyol and a physical blowing agent
- adherend polyurethane foam
- the raw material composition described in the description of the polyurethane foam of the present invention is suitable.
- examples of the “adherend” include pneumatic tires and the like, as described in the description of the polyurethane foam of the present invention.
- the “directly applying” in the production method of the present invention means that the composition used for forming the polyurethane foam is directly applied to the adherend, and an embodiment in which an adhesive is applied on the adherend before applying the composition is excluded. On the other hand, it is possible to clean or wash the surface of the adherend before applying such composition. Examples thereof include degreasing treatment and the like.
- the foaming means described in the description of the polyurethane foam of the present invention can be used, but it is preferable to apply the composition to the adherend by the injection method.
- Polyol al polyether polyol having an average functional group number of 3, a viscosity at 25 °C of 1160 mPa s and a hydroxyl value of 28 mg KOH/g, which is obtained by ring- opening addition polymerization of alkylene oxide
- Polyol a2 polyether polyol having an average functional group number of 2, a viscosity at 25 °C of 850 mPa- s and a hydroxyl value of 28 mg KOH/g, which is obtained by ringopening addition polymerization of alkylene oxide
- Catalyst cl dibutyltin dilaurate manufactured by Tokyo Fine Chemical CO., LTD.
- Catalyst c3 Toyocat ET manufactured by Tosoh Corporation
- Catalyst c4 Dabco 2040 manufactured by Evonik
- Catalyst c5 U-CAT SA102 manufactured by San-Apro Ltd.
- Foam stabilizer dl TEGOSTAB B 8715 LF 2 manufactured by Evonik
- Foam stabilizer d2 TEGOSTAB B 8745 LF 2 manufactured by Evonik
- Blowing agent e2 Solstice (trademark) LBA (HCFO-1233zd) manufactured by Honeywell
- Blowing agent e3 MARUKASOL FH (Cyclopentane) manufactured by Maruzen Petrochemical CO., LTD.
- Polyol components were prepared according to formulation in Table 1. A physical blowing agent and a polyisocyanate component were mixed, and then a polyol component was mixed to prepare a raw material composition. Compounding amounts of the polyol component, the physical blowing agent and the polyisocyanate component are shown in Table 1.
- the raw material composition prepared according to the above Preparation example of raw material composition> was directly applied to an adherend by a high-pressure foaming machine to form a polyurethane foam.
- the high-pressure foaming machine As the high-pressure foaming machine, a high-pressure foaming machine manufactured by Cannon Corporation was used. Temperatures of the polyol component and the polyisocyanate component were adjusted to the raw material temperature shown in Table 1. Discharge was carried out at a discharge rate of the raw material composition of 120 to 200 g/sec. Discharge was carried out at a discharge pressure of the raw material composition of 13 to 16 MPa.
- Foam evaluation was performed when forming the polyurethane foam according to the above Preparation example of polyurethane foam>.
- the evaluation criteria were “o” when foaming occurred without collapse, and “x” when collapse occurred during foaming.
- the results are shown in Table 1.
- Peel strength of the polyurethane foam was measured according to the following procedures. The results are shown in Table 1. In addition, the measured value was evaluated as o” when it was not less than 55 N and as “x” when it was less than 55 N. 1. Polyurethane foam was directly prepared on a flat rubber sheet according to the above
- a notch was made in the polyurethane foam with a width of 10 mm perpendicular to the rubber sheet.
- the average value obtained by measuring 5 times was defined as the peel strength of the polyurethane foam.
- a surface layer portion of the polyurethane foam prepared according to the above Preparation example of polyurethane foam> was cut to prepare a core portion with a thickness of 20 mm. Subsequently, normal incidence sound absorption coefficient for this core portion was measured according to JIS A 1405-2: 2007, and the average value of the normal incidence sound absorption coefficient at 100 to 5000 Hz was obtained. The incident direction of the sound to be measured was from the upper side in the foaming direction. The evaluation criteria were “o” for not less than 0.4 and “x” for less than 0.4. The results are shown in Table 1.
- An acrylic plate was placed vertically at a position 10 cm away from a discharge position of a high-pressure foaming machine, and the raw material composition prepared according to the above Preparation example of raw material composition> was discharged from the high- pressure foaming machine to the acrylic plate at a speed of 120 g/sec for 0.2 seconds to form a discharged product on the acrylic plate. Five minutes after the discharge, a length from the highest point to the lowest point in the vertical direction of the discharged product on the acrylic plate is measured as the liquid dripping length.
- Example 1 and Example 2 are the flexible or semirigid polyurethane foams obtained from a composition using a physical blowing agent as a blowing agent, and the adhesive strength to the adherend is high as compared to that of the flexible polyurethane foam of Comparative Example 1 obtained from a composition using water as a blowing agent.
- the amount of the crosslinking agent was not sufficient, and the polyurethane foam could not be produced.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Le problème à résoudre décrit par la présente invention est de fournir une mousse de polyuréthane présentant une force d'adhérence améliorée avec une partie à coller. La solution selon l'invention porte sur une mousse de polyuréthane souple ou semi-rigide pour une adhérence directe sur une partie à coller, dans laquelle la mousse de polyuréthane est obtenue à partir d'une composition comprenant un polyisocyanate, un polyol et un agent d'expansion physique, et dans laquelle la composition comprend un agent de réticulation ayant un nombre de groupes fonctionnels supérieur ou égal à 2 et une masse moléculaire de 60 à 1 000 g/mol en une proportion supérieure ou égale à 3 parties en masse par rapport aux 100 parties en masse du polyol.
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JP2020208424A JP2022095229A (ja) | 2020-12-16 | 2020-12-16 | ポリウレタンフォームおよびその製造方法 |
JP2020-208424 | 2020-12-16 | ||
EP21153253.6A EP4032924A1 (fr) | 2021-01-25 | 2021-01-25 | Mousse de polyuréthane et son procédé de production |
EP21153253.6 | 2021-01-25 |
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US20040154718A1 (en) * | 2003-02-06 | 2004-08-12 | Doesburg Van I. | Polyurethane filled tire and method of making same |
JP2012117039A (ja) | 2010-11-30 | 2012-06-21 | Hankook Tire Co Ltd | ポリウレタンフォーム及びこれを含む空気入りタイヤ |
US20150151592A1 (en) * | 2012-06-08 | 2015-06-04 | Compagnie Generale Des Etablissements Michelin | Tyre, the inner wall of which has a layer of specific polyurethane foam |
JP2018070148A (ja) | 2016-10-25 | 2018-05-10 | ハンコック タイヤ カンパニー リミテッド | 共鳴音低減タイヤ |
KR101901399B1 (ko) * | 2016-07-18 | 2018-09-28 | 넥센타이어 주식회사 | 타이어의 제조 방법 및 이를 이용하여 제조된 타이어 |
JP2020019390A (ja) | 2018-08-01 | 2020-02-06 | 住友ゴム工業株式会社 | 制音体付き空気入りタイヤ,及びその製造方法 |
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US20040154718A1 (en) * | 2003-02-06 | 2004-08-12 | Doesburg Van I. | Polyurethane filled tire and method of making same |
JP2012117039A (ja) | 2010-11-30 | 2012-06-21 | Hankook Tire Co Ltd | ポリウレタンフォーム及びこれを含む空気入りタイヤ |
US20150151592A1 (en) * | 2012-06-08 | 2015-06-04 | Compagnie Generale Des Etablissements Michelin | Tyre, the inner wall of which has a layer of specific polyurethane foam |
KR101901399B1 (ko) * | 2016-07-18 | 2018-09-28 | 넥센타이어 주식회사 | 타이어의 제조 방법 및 이를 이용하여 제조된 타이어 |
JP2018070148A (ja) | 2016-10-25 | 2018-05-10 | ハンコック タイヤ カンパニー リミテッド | 共鳴音低減タイヤ |
JP2020019390A (ja) | 2018-08-01 | 2020-02-06 | 住友ゴム工業株式会社 | 制音体付き空気入りタイヤ,及びその製造方法 |
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