GB1587046A - Process for the production of filler-reinforced polyurethane elastomers - Google Patents
Process for the production of filler-reinforced polyurethane elastomers Download PDFInfo
- Publication number
- GB1587046A GB1587046A GB16932/78A GB1693278A GB1587046A GB 1587046 A GB1587046 A GB 1587046A GB 16932/78 A GB16932/78 A GB 16932/78A GB 1693278 A GB1693278 A GB 1693278A GB 1587046 A GB1587046 A GB 1587046A
- Authority
- GB
- United Kingdom
- Prior art keywords
- din
- parts
- sulphonate
- group
- filler
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 27
- 230000008569 process Effects 0.000 title claims description 24
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- 229920003225 polyurethane elastomer Polymers 0.000 title claims description 10
- -1 alkali metal cation Chemical class 0.000 claims description 55
- 150000001875 compounds Chemical class 0.000 claims description 46
- 239000000945 filler Substances 0.000 claims description 30
- 229920002635 polyurethane Polymers 0.000 claims description 30
- 239000004814 polyurethane Substances 0.000 claims description 30
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 26
- 229920001228 polyisocyanate Polymers 0.000 claims description 22
- 239000005056 polyisocyanate Substances 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 15
- 239000004970 Chain extender Substances 0.000 claims description 14
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 13
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 10
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims description 10
- 229920005862 polyol Polymers 0.000 claims description 10
- 150000003077 polyols Chemical class 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000002245 particle Substances 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 239000004604 Blowing Agent Substances 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 3
- 239000011256 inorganic filler Substances 0.000 claims description 3
- 239000012766 organic filler Substances 0.000 claims description 3
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 229910018626 Al(OH) Inorganic materials 0.000 claims 1
- 150000002009 diols Chemical class 0.000 description 38
- 239000000203 mixture Substances 0.000 description 29
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 21
- 229920000570 polyether Polymers 0.000 description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- 239000004721 Polyphenylene oxide Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 125000005442 diisocyanate group Chemical group 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 8
- 125000003010 ionic group Chemical group 0.000 description 8
- 230000003993 interaction Effects 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 7
- 150000002513 isocyanates Chemical class 0.000 description 7
- 238000000465 moulding Methods 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- 239000010457 zeolite Substances 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229920001971 elastomer Polymers 0.000 description 6
- 239000000806 elastomer Substances 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 230000006872 improvement Effects 0.000 description 6
- ZFDWWDZLRKHULH-UHFFFAOYSA-N 1,2-dimethyl-5,6-dihydro-4h-pyrimidine Chemical compound CN1CCCN=C1C ZFDWWDZLRKHULH-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 229910021536 Zeolite Inorganic materials 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000002131 composite material Substances 0.000 description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 239000004872 foam stabilizing agent Substances 0.000 description 4
- 150000002334 glycols Chemical class 0.000 description 4
- 229920006295 polythiol Polymers 0.000 description 4
- 239000004800 polyvinyl chloride Substances 0.000 description 4
- 229920000915 polyvinyl chloride Polymers 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical class [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000011248 coating agent 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
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920006324 polyoxymethylene Polymers 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- OMGBIRBWZDOCQQ-YPKPFQOOSA-N (z)-2-(diethylamino)octadec-9-enoic acid Chemical compound CCCCCCCC\C=C/CCCCCCC(C(O)=O)N(CC)CC OMGBIRBWZDOCQQ-YPKPFQOOSA-N 0.000 description 2
- OYWRDHBGMCXGFY-UHFFFAOYSA-N 1,2,3-triazinane Chemical class C1CNNNC1 OYWRDHBGMCXGFY-UHFFFAOYSA-N 0.000 description 2
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-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
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-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
- 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 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 229930195725 Mannitol Natural products 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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229910021502 aluminium hydroxide Inorganic materials 0.000 description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000010425 asbestos Substances 0.000 description 2
- 239000000022 bacteriostatic agent Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 2
- 235000012241 calcium silicate Nutrition 0.000 description 2
- 235000011132 calcium sulphate Nutrition 0.000 description 2
- 239000004568 cement Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000002993 cycloalkylene group Chemical group 0.000 description 2
- VKONPUDBRVKQLM-UHFFFAOYSA-N cyclohexane-1,4-diol Chemical compound OC1CCC(O)CC1 VKONPUDBRVKQLM-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000007046 ethoxylation reaction Methods 0.000 description 2
- 229940093499 ethyl acetate Drugs 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 230000001408 fungistatic effect Effects 0.000 description 2
- 229910001679 gibbsite Inorganic materials 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
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- 229910052806 inorganic carbonate Inorganic materials 0.000 description 1
- 239000010954 inorganic particle Substances 0.000 description 1
- 229910052920 inorganic sulfate Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229940006487 lithium cation Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- ZWRDBWDXRLPESY-UHFFFAOYSA-N n-benzyl-n-ethylethanamine Chemical compound CCN(CC)CC1=CC=CC=C1 ZWRDBWDXRLPESY-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- SZEGKVHRCLBFKJ-UHFFFAOYSA-N n-methyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNC SZEGKVHRCLBFKJ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 125000005474 octanoate group Chemical group 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000011236 particulate material Substances 0.000 description 1
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000005011 phenolic resin Substances 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
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005903 polyol mixture Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000011527 polyurethane coating Substances 0.000 description 1
- 229920003009 polyurethane dispersion Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- QDGHXQFTWKRQTG-UHFFFAOYSA-N pyrimidin-2-ylhydrazine Chemical compound NNC1=NC=CC=N1 QDGHXQFTWKRQTG-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004291 sulphur dioxide Substances 0.000 description 1
- 235000010269 sulphur dioxide Nutrition 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- SYRHIZPPCHMRIT-UHFFFAOYSA-N tin(4+) Chemical class [Sn+4] SYRHIZPPCHMRIT-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical group NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3878—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus
- C08G18/388—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus having phosphorus bound to carbon and/or to hydrogen
-
- 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
- C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
- C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
-
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0008—Foam properties flexible
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0033—Foam properties having integral skins
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0041—Foam properties having specified density
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Polyurethanes Or Polyureas (AREA)
Description
(54) A PROCESS FOR THE PRÖDÚCTION OF FILLER
REINFORCED POLYURETHANE ELASTOMERS
(71) We, BAYER AKTIENGESELLSCHAFT, a body corporate organised under the laws of Germany of 509 Leverkusen, Germany, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:
This invention relates to a process for the production of filler-containing polyurethane elastomers with improved interaction between the filler and the polyurethane. The improvement is obtained by the incorporation of organic compounds containing ionic groups into the polyurethane molecule.
It is often desirable on economic grounds to produce polyurethanes containing relatively large quantities of filler because the reduction in price which can be obtained in this way makes new fields of application possible. Although the increase in the density caused by the filler is a disadvantage in many applications because required weights or dimensions can no longer be attained, the filler polyurethane can nevertheless be adapted to suit the required conditions in cases such as these by foaming, i.e. by using blowing agents in the production of the plastic.
Filler-containing polyurethanes in foamed or solid form are already known.
Thus, the use of fillers for homogeneous polyurethanes is described, for example, in
J. H. Saunders and K. C. Frisch "Polyurethanes, Chemistry and Technology" (1964), Part I, page 343 and Part II, pages 69 et seq, and in Bayer
Kunststofftaschenbuch, 3rd Edition 1963, page 138, and also in the pamphlet published by Bayer AG on Desmoflex (1.9.1967). H. Gruber also reports on this subject in "Polyurethanbeschichtungen im Strassenbau (Polyurethane Coatings in
Road Building)" (Kunststoffe im Bau, Themenheft 9; Verlag: Strassenbau, Chemie,
Technik; 1st Quarter 1968; Verlags-GmbH, Heidelberg).
The use of fillers such as, for example, inorganic carbonates and sulphates,
PVC-powders or even sawdust has adverse consequences on various mechanical properties in conventional processes. In comparison with non-filled polyurethane systems, filled systems show, for example, distinctly reduced elasticity, greater brittleness, a marked tendency towards breakage and an often inadequate tear propagation resistance.
The obejct of the present invention is to reduce the above-mentioned disadvantages of conventional filler-containing polyurethane plastics and, in addition, to provide new composite materials which, in particular, have the advantage of a better interaction between the filler and the polyurethane matrix.
According to the invention, this object is achieved by using hydroxy-functional chain extenders containing anionic groups in the production of the polyurethane.
The advantageous effect of the presence of ionic groups in the chain extender and hence in the polyurethane is presumably largely explained by interactions between the ionic groups and the surfaces of the filler particles which favourably affect adhesion, although this is not intended in any way to limit the scope of the invention. This effect is particularly pronounced in cases where it is desired to join inorganic particles to one another. Because the surfaces of such particles are almost never totally neutral, but generally show a positive or negative charge, direct ionic bonds are either produced by using ionically modified chain extenders, or strong bonds which would appear to be of the order of heterolytic dissociation energies are effected by the interaction of opposite charges on the filler and in the polyurethane binder.
The interaction forces referred to above also occur, although perhaps to a somewhat lesser extent, where organic filler particles are used, particularly- in the case of organic polymers which contain polar or polarisable groups in any form, because polarisation and induction effects are in themselves sufficient to produce significant interactions with the ionic group of the chain extender and, hence, improved adhesion properties. The adhesion between substrate and binder is the most important factor in the quality of a composite material. If the adhesion between the phases is improved, better properties of the composite material in use are obtained.
It has now surprisingly been found that these improvements in properties can be obtained to a particularly large extent'by using the diols containing sulphonate and/or phosphonate groups described in the following.
Accordingly, the present invention relates to a process for the production of a filler-containing polyurethane elastomers Which may be foamed by reacting together
(a) a compound containing at least 2 Zerewitinoff-active hydrogen atoms and having a molecular weight of from 400 to 10,000, preferably from 800 to 6000 and, with particular preference, from 1000 to 4000,
(b) an organic polyisocyanate, optionally
(c) a chain extender having a molecular weight in the range from 32 to 400,
(d) 50 to 500 parts by weight preferably from 75 to 250 parts by weight based on 100 parts by weight of polyurethane solids, of an inorganic or organic filler and optionally
(e) blowing agents, catalysts and other auxiliaries and additives, wherein a polyhydroxyl compound containing at least one sulphonate and/or phosphonate group is used as at least part of component (a) and/or (c) in such a quantity that the polyurethane elastomer contains from 1 to 10% by weight, preferably from 3 to 8% by weight and, with particular preference, from 3.5 to 7% by weight of sulphonate and/or, phosphonate groups based on 100% by weight of the polyurethane solids.
The polyurethane recipe preferably contains from 40 to 91% by weight of non-ionic relatively high molecular weight polyhydroxyl compounds, from 1 to 10% by weight of non-ionic chain extenders, from 1 to 10% by weight of diols containing sulphonate or phosphonate groups and from 7 to 40% by weight of polyisocyanates.
According to the invention, it is preferred to use diols containing sulphonate or phosphonate groups which have a melting point below 1200C. According to the invention, the following compounds are preferred:
(1) sulphonate-group-containing diols corresponding to the formula
in which
A and B which may be the same or different represent difunctional aliphatic hydrocarbon radicals containing from 1 to 6 carbon atoms,
R represents hydrogen, an aliphatic hydrocarbon radical containing from 1 to 4 carbon atoms or a phenyl radical,
X'+' an alkali metal cation or an ammonium group which may be substituted, preferably by C1-C10-al kyl radicals,
n and m which may be the same or different represent integers from 0 to 30, preferably from 0 to 3,
o and p = 0 to 1 and
q is an integer from 0 to 2.
Preferred sulphonate-group-containing diols corrresponding to general formula (I) are those corresponding to the formulae
in which
R represents hydrogen or a methyl group,
n and m which may be the same or different represent integers of from 0 te 3 and
X'+' is as already defined.
As already mentioned, sulphonate-group-containing diols with a melting or softening point below 1200C are used with particular preference in the process according to the invention. In the case where n = m = 0 in compounds of formula (I), this requirement is satisfied particularly when Xttr represents a lithium cation or
an NH4'+)-ion. In cases where it is intended to use sodium or potassium salts of the diols containing sulphonate groups, it is particularly advisable to use those compounds of formulae (Ia), (Ib) and (Ic) in which n and m have a value (on a statistical average) of from 0.8 to 2. Those representatives of the last-mentioned
compounds in which R represents a methyl radical are especially preferred.
The compounds of formula (Ia) are readily produced bylreacting a methylene-1,3-propane diol which may be alkoxylated with a bisulphite Xs HSO3 e in aqueous medium. To this end, the unsaturated diol is dissolved in water, followed by the addition to the resulting solution of an aqueous solution of the bisulphite which has been adjusted beforehand to a pH-value of 7.1 with dilute hydroxide solution X OH. The reaction mixture is stirred at room temperature and, at the same time, the pH-value is kept at 7.0 to 7.1 by the addition of dilute sulphuric acid. The reaction is complete when the pH-value remains constant.
Following acidification to pH 2 to 3, the excess of sulphur dioxide is removed by stirring. The mixture is then neutralised with dilute hydroxide solution X OH and concentrated to dryness. The diol containing sulphonate groups is then extracted with methanol. In this process, it is preferred to use bisulphites X HSO3 and hydroxide solutions X OH in which X represents potassium, sodium, lithium or ammonium. The sulphonate diols thus obtained are readily converted into those in which X represents another component, for example a substituted ammonium
group, by replacing the cation X'+' initially present by a hydrogen ion by means of an ion exchanger, and subsequently neutralising the free acid thus obtained with the required base.
The compounds of formula (Ib) are similarly produced by the addition of bisulphite to 2-butene-1,4-diol which may be alkoxylated.
The compounds of formula (Ic) are similarly produced by the addition of
bisulphite to l-butene-3,4-diol which may be alkoxylated.
The addition df bisulphite to unsaturated diols such as these is described in detail in German Offenlegungsschrift No. 2,417,664.
(2) Sulphonate-group-containing diols corresponding to the general formula
in which
X'+' represents an alkali metal cation or an ammonium group which may be substituted, preferably by C1-C10-alkyl radicals,
n and m which may be the same or different represent integers of 1 to 6 and
p is an integer of- 1 to 4.
Sulphonate-group-containing diols of general formula (II) which are preferably used in the process according to the invention are:
a) those corresponding to the formula
in which Xt+' is as defined above and n and m which may be the same or different represent integers of from 1 to 6, preferably from 3 to 4,
b) those corresponding to the formula
in which
X'+' is as defined above and n and m which may be the same or different represent integers of from 1 to 6, preferably from 2 to 4.
The compounds of formula (IIa) are readily produced by reacting diethanolamine, or the ethoxylation product of diethanolamine, with formaldehyde and then with a bisulphite (HSO3X).
The compounds of formula (IIb) are produced by adding a solution of I mole of butane sulphone in 200 ml of toluene dropwise to a solution of 1 mole of diethanolamine (or its ethoxylation product) in 500 ml of toluene, stirring the resulting solution for 12 hours at 400C and then concentrating it, followed by dissolution in 500 ml of water and conversion into the salt with sodium hydroxide.
M.P.: 143 to 1450C (where m = n = 1).
(3) Sulphonate-group-containing diols corresponding to the general formula
in which
R represents an alkylene radical with 2 to 4 carbon atoms and/or a difunctional aromatic or araliphatic radical containing from 6 to 15 carbon atoms, X'+' represents an alkali metal cation or an ammonium group which may be substituted preferably by C1-C10-alkyl groups,
R' and R2 represent hydrogen and/or the same or different alkyl radicals containing from I to 6 carbon atoms and
n and m which may be the same or different represent integers from I to 6.
Sulphonate-group-containing diols of general formula (III) which are preferably used in the process according to the invention are:
a) those corresponding to the formula
in which
R' and R2 which may be the same or different represent hydrogen or alkyl radicals containing from I to 6 carbon atoms, more especially I to 2 carbon atoms,
X'+' is as defined above and
n and m represent the same or different numbers from I to 6, more especially from 2 to 4;
b) those corresponding to the formula
in which
X'+', R' and R2 are as defined above and
m and n represent the same or different numbers from I to 6, more especially from 2 to 4;
c) those corresponding to the formula
in which X'+', R' and R2 are as defined above and
m and n represent the same or differen-t numbers from 1 to 6, more especially from 2- to 4.
The compounds of formulae(IIIa, b and c) are produced from the corresponding bis-epoxides (reaction products of hydroxyfunctional aromatic and araliphatic compounds and epichlorhydrin or epibromhydrin) and, for example, 2aminoethane sulphonate or 2-methylaminoethane sulphonate or 2butylaminoethane sulphonate in aqueous solution at 20 to 500 C.
(4) Phosphonate-group-containing diols corresponding to the general formula
in which
R represents a hydrogen atom or an alkyl radical with I to 4 carbon atoms or a phenyl radical,
X'+' represents an alkali metal cation, more especially Na'+' or K'+', or an ammonium group which may be substituted preferably by C1-C10-alkyl radicals and
n is an integer from 1 to 4.
Phosphonate-group-containing diols of the above general formula which are preferably used in the process according to the invention are those in which n and R represents hydrogen, methyl or ethyl.
The compounds of formula (IV) are produced for example by dissolving I mole of a 75% phosphorus acid or its alkyl or phenyl ester in approximately 200 ml of water and adding I mole of glycidol dissolved in 75 ml of toluene dropwise to this mixture over a period of 35 minutes at 0 to 100C. The mixture is then stirred for 2 hours at 0 to 100C and for 2.5 hours at room temperature. I Mole of sodium hydroxide solution in 100 ml of water is then added dropwise at 20 to 250C. The organic phase is then separated off from the aqueous phase. The diols containing phosphonate groups used in accordance with the invention are obtained from the aqueous phase in the form of oily compounds.
The above-described diols preferably used in accordance with the invention generally contain from 60 to 700, preferably from 200 to 600, milliequivalents of anionic groups per 100 g.
The use ot diols containing sulphonate groups in the production of aqueous polyurethane dispersions is described in German Offenlegungsschrift No.
2,446,440. However, this has nothing to do with the process according to the invention for the production of polyurethane elastomers which may be foamed.
Neither is there any reference in DOS No. 2,446,440 to the incorporation of fillers into the ionically modified polyurethane.
Starting components suitable for use in the process according to the invention include aliphatic, cycloaliphatic, araliphatic, aromatic and heterocyclic polyisocyanates of the type described for example, by W. Siefken in Justus Liebigs
Annalen der Chemie, 562, pages 75 to 136, for example ethylene diisocyanate; 1,4tetramethylene diisocyanate; 1,6-hexamethylene diisocyanate; 1,1 2-dodecane diisocyanate; cyclobutane- 1 ,3-diisocyanate; cyclohexane-1,3 or 1,4-diisocyanate or a mixture of these isomers; I -isocyanato-3 ,3,5-trimethyl-5-isocyanatomethyl cyclohexane (as described in German Auslegeschrift No. 1,202,785 and U.S. Patent
No. US-PS 3,401,190; 2,4- or 2,6-hexahydrotolylene diisocyanate or a mixture of these isomers; hexahydro-1,3- and/or 1 ,4-phenylene diisocyanate; perhydro-2,4' and/or -4,4'-diphenylmethane diisocyanate; 1,3-and 1,4-phenylene diisocyanate; 2,4- or 2,6-tolylene diisocyanate or a mixture of these isomers; diphenyl methane2,4'- and/or -4,4'-diisocyanate; naphthylene- 1 ,5-diisocyanate; triphenyl methane4,4',4"-triisocyanate; polyphenyl polymethylene polyisocyanates of the type which can be obtained by condensing aniline with formaldehyde, followed by phosgenation, and which are described, for example, in British Patent
Specifications No. 874,430 and 848,671; m- and p-isocyanatophenyl sulphonyl isocyanates according to US-Patent No. 3,454,606; perchlorinated aryl polyisocyanates of the type described, for example, in German Auslegeschrift No.
1,157,602 and US Patent No. 3,277,138; polyisocyanates containing carbodiimide groups of the type described in German Patent Specification No. 1,092,007 and US
Patent No. 3,152,162; diisocyanates of the type described in US Patent
Specification No. 3,492,330; polyisocyanates containing allophanate groups of the type described, for example, in British Patent Specification No. 994,890; Belgian
Patent Specification No. 761,626 and published Dutch Patent Application No.
7,102,524; polyisocyanates containing isocyanurate groups of the type described, for example, in US Patent No. 3,001,973; German Patent Specifications Nos
1,002,789; 1,222,067 and 1,027,394 and German Offenlegungsschrifts 1,929,034 and
2,004,048; polyisocyanates containing urethane groups of the type described, for
example, in Belgian Patent Specification No. 752,261 and US Patent Specification
3,394,164; polyisocyanates containing acylated urea groups according to German
Patent Specification No. 1,230,778; polyisocyanates containing biuret groups of the type described, for example, in German Patent Specification 1,101,394; US Patents
Nos. 3,124,605 and 3,201,372 and British Patent Specification 889,050;
polyisocyanates obtained by telomerisation reactions of the type described, for
example, in US Patent No. 3,654,106; polyisocyanates containing ester groups of the type described, for example, in British Patent Specifications No. 965,474 and
1,072,956; US Patent Specification No. 2,567,763 and German Patent Specification
No. 1,231,688 and the reaction products of the above-mentioned isocyanates with
acetals according to German Patent Specification No. 1,072,385 and polyisocyanates containing polymeric fatty acid radicals according to US Patent
No. 3,455,883.
It is also possible to use the isocyanate-group-containing distillation residues obtained in the production of isocyanates on a commercial scale, which may be in solution in one or more of the aforementioned polyisocyanates. It is also possible to use any mixtures of the aforementioned polyisocyanates.
Particularly preferred isocyanates are polyphenyl-poly-methylene polyisocyanates having a functionality of from 2.0 to 2.5, more especially from 2 to 2.2, of the type obtained by condensing aniline with formaldehyde, followed by phosgenation.
Other starting components which may be used in accordance with the invention are compounds containing at least two isocyanate-reactive hydrogen atoms and having a molecular weight in the range from 400 to 10,000. In addition to compounds containing amino groups, thiol groups or carboxyl groups, compounds of this type are preferably polyhydroxyl compounds, more especially compounds containing from two to eight hydroxyl groups, particularly those with molecular weights in the range from 800 to 10,000, and preferably in the range from 1000 to 6000, for example polyesters, polyethers, polythioethers, polyacetals, polycarbonates, polyhamides and polyester amides containing at least 2, generally 2 to 8, but preferably 2 to 4 hydroxyl groups, of the type commonly used for the production of homogeneous and cellular polyurethanes.
Examples of suitable polyesters containing hydroxyl groups are reaction products of polyhydric, preferably dihydric and, optionally, trihydric alcohols with polybasic, preferably diabasic, carboxylic acids. Instead of the free polycarboxylic acids, the corresponding polycarboxylic acid anhydrides or corresponding polycarboxylic acid esters of lower alcohols or mixtures thereof may also be used for the production of the polyesters. The polycarboxylic acids may be aliphatic, cycloaliphatic, aromatic and/or heterocyclic, and may be substituted, for example by halogen atoms, and/or unsaturated.
Examples of these polycarboxylic acids are succinic acid, adipic acid, suberic acid, azelaic acid, sebacic acid, phthalic acid, isophthalic acid, trimellitic acid, phthalic acid anhydride, tetrahydrophthalic acid anhydride, hexahydrophthalic acid anhydride, tetrachlorophthalic acid anhydride, endomethylene tetrahydrophthalic acid anhydride, glutaric acid anhydride, maleic acid, maleic acid anhydride, fumaric acid, dimeric and trimeric fatty acids, which may be used in admixture with monomeric fatty acids, such as eleic acid, terephthalic acid dimethyl ester and terephthalic acid-bis-glycol ester. Examples of suitable polyhydric alcohols are ethylene glycol, 1,2- and 1,3-propylene glycol, 1,4- and 2,3butylene glycol, 1,6-hexane diol, 1,8-octane diol, neopentyl glycol, cyclohexane dimethanol (1 ,4-bis-hydroxymethylcyclohexane), 2methyl ,3-propanediol, glycerol, trimethylol propane, 1,2,6-hexane triol, 1,2,4-butane triol, trimethylol ethane, pentaerythritol, quinitol, mannitol and sorbitol, methyl glycoside, also diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycols, dipropylene glycol, polypropylene glycols, dibutylene glycol and polybutylene glycols. The polyesters may contain terminal carboxyl groups. Polyesters of lactones, for example E-caprolactone or hydroxy carboxylic acids, for example whydroxy caproic acid, may also be used.
The polyethers containing at least 2, generally 2 to 8 and preferably 2 to 3 hydroxy groups which may be used in accordance with the invention are also known per se and are obtained, for example, by polymerising epoxides such as ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, styrene oxide or epichlorhydrin on their own, for example in the presence of borontrifluoride, or by adding these epoxides, either in admixture or successively, with starter components containing reactive hydrogen atoms such as water, alcohols, ammonia or amines, for example ethylene glycol, 1,3- or 1,2-propylene glycol, trimethylol propane, 4,4'hydroxy diphenyl propane, aniline, ethanolamine or ethylene diamine. Sucrose polyethers of the type described, for example, in German Auslegeschrifts Nos.
1,176,358 and 1,064,938, may also be used in accordance with the invention. In many cases, it is preferred to use polyethers which predominantly contain promary hydroxyl groups (up to 90% by weight, based on all the hydroxyl groups present in the polyether). Polyethers modified by vinyl polymers, of the type formed for example by polymerising styrene and acrylonitrile in the presence of polyethers as described in US Patents Nos. 3,383,351; 3,304,273; 3,523,093 and 3,110,695 and
German Patent No. 1,152,536 are also suitable. Polybutadienes containing hydroxyl groups may also be used.
Among the polythioethers, reference is made in particular to the condensation products of thiodiglycol on its own and/or with other glycols, dicarboxylic acids, formaldehyde, aminocarboxylic acids or amino alcohols. Depending upon the cocomponents, these products include polythio mixed ethers, polythioether esters or polythioether ester amides.
Suitable polyacetals are, for example, those compounds which can be obtained from glycols, such as diethylene glycol, triethylene glycol, 4,4'-dioxethoxy diphenyl dimethyl methane and hexane diol, and formaldehyde. Polyacetals suitable for the purposes of the invention may also be obtained by polymerising cyclic acetals.
Suitable polycarbonates containing hydroxyl groups are those known per se obtainable, for example, by reacting diols such as 1,3-propane diol, 1,4-butane diol and/or 1,6-hexane diol, diethylene glycol, triethylene glycol or tetraethylene glycol, with diaryl carbonates, for example diphenyl carbonate, or phosgene.
Examples of the polyester amides and polyamides are the predominantly linear condensates obtained from polybasic, saturated and unsaturated carboxylic acids and their anhydrides and polyhydric saturated and unsaturated amino alcohols, diamines, polyamines and their mixtures.
Polyhydroxyl compounds already containing urethane or urea groups and optionally modified natural polyols such as castor oil, carbohydrates, e.g. starch, may also be used. Addition products of alkylene oxides with phenol-formaldehyde resins or even with urea-formaldehyde resins may also be used in accordance with the invention.
Representatives of these compounds used in accordance with the invention are described, for example, in High Polymers, Vol. XVI, "Polyurethanes,
Chemistry and Technology", by Saunders-Frisch, Interscience Publishers, New
York, London, Vol. I, 1962, pages 32 to 42 and pages 44 to 54, and Vol. II, 1964, pages 5--6 and 198-1 99, and in Kunststoff-Handbuch, Vol. VII, Vieweg-Hchtlen, Carl Hanser-Verlag, Munich, 1966, for example on pages 45 to 71.
It is of course also possible to use mixtures of the above-mentioned compounds containing at least two isocyanate-reactive hydrogen atoms and having a molecular weight in the range from 400 to 10,000, for example mixtures of polyethers and polyesters.
Other starting components which may be used in accordance with the invention are compounds containing at least two isocyanate-reactive hydrogen atoms and having a molecular weight in the range from 32 to 400. In this case, too, the compounds in question are compounds containing hydroxyl groups and/or amino groups and/or thiol groups and/or carboxyl groups, preferably compounds containing hydroxyl groups and/or amino groups which are used as chain extenders or crosslinkers. These compounds generally contain from 2 to 8 isocyanatereactive hydrogen atoms, preferably 2 or 3 reactive hydrogen atoms.
In this case, too, it is possible to use mixtures of different compounds containing at least two isocyanate-reactive hydrogen atoms and having a molecular weight in the range from 32 to 400.
Examples of compounds such as these are ethylene glycol, 1,2- and 1,3propylene glycol, 1,4- and 2,3-butylene glycol, 1,5-pentane diol, 1,6-hexane diol, 1,8-octane diol, neopentyl glycol, I ,4-bis-hydroxymethyl cyclohexane, 2-methyl1,3-propane diol, glycerol, trimethylol propane, 1,2,6-hexane triol, trimethylol ethane, pentaerythritol, quinitol, mannitol and sorbitol, diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycols having a molecular weight of up to 400, dipropylene glycol, polypropylene glycols having a molecular weight of up to 400, dibutylene glycol, polybutylene glycols having a molecular weight of up to 400, castor oil, 4,4'-dihydroxydiphenyl propane, dihydroxymethyl hydroquinone, 1,4-phenylene-bis-(p-hydroxyethylether), ethanolamine, N-methyl ethanolamine, diethanolamine, N-methyl diethanolamine, triethanolamine, 3aminopropanol, ester diols corresponding to the general formulae HO QCH2)XCOOHCH2)VOH and HO-(CH,),-O-CO-R-CO-O-(CH,),-OH in which
R represents an alkylene or arylene radical containing from 1 to 10, preferably from 2 to 6 carbon atoms,
x = 2-6 and y = 3-5, for example #-hydroxybutyl-#-hydroxycaproic acid ester, #-hydroxyhexyl-γ- hydroxy butyric acid ester, adipic acid-bis-(p-hydroxyethyl)-ester and terephthalic acid-bis-(p-hydroxyethyl)-ester; also diol urethanes corresponding to the general formula
HO-(CH2)x-O-CO-NH-R'-NH-CO-O-(CH2)x-OH in which
R' represents an alkylene, cycloalkylene or arylene radical containing from 2 to 15, preferably 2 to 6, carbon atoms and
x is a number from 2 to 6. for example 1,6-hexamethylene-bis-( -hydroxyethyl-urethane) or 4,4'-diphenyl methane-bis-(#-hydroxybutyl-urethane); diol ureas corresponding to the general formula
in which
R" represents an alkylene, cycloalkylene or arylene radical containing from 2 to 15, preferably 2 to 9, carbon atoms,
R"' represents hydrogen or methyl and
x = 2 or 3. for example 4,4'-diphenyl-methane-bis-( -hydroxyethyl-urea) or the compound
Aliphatic diamines suitable for use in accordance with the invention are, for example, ethylene diamine; 1,4-tetramethylene diamine; 1,11-undecamethylene diamine; 1,12-do-decamethylene diamine and mixtures thereof; 1-amino-3,3,5trimethyl-5-aminomethyl cyclohexane; 2,4- and 2,6-hexahydrotolylene diamine and mixtures thereof; perhydro-2,4'- and -4,4'- hydroxyphthalic acid and 4-aminophthalic acid.
It is also possible to use compounds having a functionality of one with respect to isocyanates as so-called chain terminators in quantities of from 0.01 to 10% by weight, based on polyurethane solids. Monofunctional compounds such as these are, for example, monoamines such as butyl and dibutylamine, octylamine, stearylamine, N-methylstearylamine, pyrrolidine, piperidine and cyclohexylamine, monoalcohols such as butanol, 2-ethyl hexanol, octanol, dodecanol, the various amyl alcohols, cyclohexanol and ethylene glycol monoethyl ether.
However, it is also possible in accordance with the invention to use polyhydroxyl compounds containing high molecular weight polyadducts or polycondensates in finely disperse or dissolved form. Modified polyhydroxyl compounds such as these are obtained by carrying out polyaddition reactions, for example reactions between polyisocyanates and aminofunctional compounds, or polycondensation reactions, for example between formaldehyde and phenols and/or amines, directly in situ in the above-mentioned compounds containing hydroxyl groups. Processes such as these are described, for example, in German
Auslegeschrifts Nos. 1,168,075 and 1,260,142 and German Offenlegungsschrifts
Nos. 2,324,134; 2,423,984; 2,512,385; 2,513,815; 2,550,796; 2,550,797; 2,550,833 and 2,550,862. However, it is also possible, in accordance with US Patent No.
3,969,413 or German Offenlegungsschrift No. 2,550,860, to mix an aqueous polymer dispersion with a polyhydroxyl compound and subsequently to remove the water from the mixture.
In cases where modified polyhydroxyl compounds of the type mentioned above are used as starting component in the polyisocyanate polyaddition process, polyurethane plastics with considerably improved mechanical properties are formed in many cases.
The inorganic or organic particulate materials to be used in the process according to the invention should generally have a particle size of from 0.01 y to 1000 , preferably from 0.1 ju to 200 ,u.
A variety of different solid inorganic or organic substances may be used as fillers, including for example dolomite, calcium carbonate, alumina, asbestos, water glass, silica, sand, talcum, iron oxide, aluminium oxide and oxide hydrates, alkali silicates, zeolites, mixed silicates, calcium silicates, calcium sulphates aluminosilicates, cements, basalt wool, bronze or silicon dioxide powder, polyvinyl chloride, polystyrene, polyethylene, polypropylene, polyacrylonitrile, polybutadiene, polyisoprene, polytetrafluoroethylenes, aliphatic and aromatic polyesters, melamine urea or phenolic resins, nolyacetal resins, polyepoxides, polyhydantoins, polyureas, polyethers, polyurethanes. polyimides, polyamides, poiysulphones, polycarbonates, and of course also any copolymers. Foamed fillers, for example expanded clay or foamed polystyrene, may also be used in accordance with the invention.
Particuiarly preferred materials are chalk, alumina, asbestos, sand, calcium silicates, cements, calcium sulphate, aluminosilicates and barium sulphate.
According to the invention, water and/or readily volatile organic substances may be used as blowing agents. Suitable organic blowing agents are, for example, acetone, ethylacetate, halogen-substituted alkanes, such as methylene chloride, chloroform, ethylidene chloride, monofluorotrichloromethane, chlorodifluoromethane and dichloroditluoromethane, also butane, hexane, heptane or diethyl ether or vinylidene chloride. A blowing effect may also be obtained by adding compounds which decompose at temperatures above room temperature giving off gases, for example nitrogen, for example azo compounds such as azoisobutyronitrile. Other examples of blowing agents and information on the use of blowing agents may be found in Kunststoff-Handbuch, Vol. VII, by
Vieweg und Hochtlen, Carl-Hanser-Verlag, Munich 1966, for example on pages 108 and 109, 453 to 455 and 507 to 510.
In order to control the isocyanate reaction with isocyanate-reactive hydrogen atoms or even with other isocyanate groups in the required sense as a function of time, catalysts are often used in accordance with the invention Suitable catalysts are those known per se, for example tertiary amines such as triethylamine, tributylamine, N-methyl morpholine, N-ethyl morpholine, N-cocomorpholine, N,N,N',N'-tetramethyl ethylene diamine, 1,4-diazabicyclo-(2,2,2)-octane, Nmethyl-N'-dimethylaminoethyl piperazine, N,N-dimethyl benzylamine, bis-(N,Ndiethylaminoethyl)-adipate, N,N-diethylbenzylamine, pentamethyl diethylene triamine, N,N-dimethyl cyclohexylamine, N,N,N',N'-tetramethyl-l,3-butane diamine, N,N-dimethyl-p-phenyl-ethylamine, 1 ,2-dimethyl imidazole, 2-methyl
imidazole, 2,3-dimethyl tetrahydropyrimidine, 2-aminopyridine, 2,6
diaminopyridine and 2-hydrazinopyrimidine.
Tertiary amines containing isocyanate-reactive hydrogen atoms are, for
example, triethanolamine, triisopropanolamine, N-methyl diethanolamine, N-ethyl
diethanolamine, N,N-dimethyl ethanolamine and also their reaction products with alkylene oxides, such as propylene oxide and/or ethylene oxide.
Other suitable catalysts are sila-amines with carbon-silicon bonds of the type
described for example in German Patent Specification No. 1,229,290
(corresponding to US Patent Specification No. 3,620,984), for example 2,2,4 trime'thyl-2-silamorpholine and 1,3-diethylaminomethyl tetramethyl disiloxan6.
Other suitable catalysts are nitrogen-containing. bases, such as tetra
alkylammonium hydroxides and also alkali metal hydroxides such as sodium
hydroxide, alkali metal phenolates, such as sodium phenolate, or alkali metal
alcoholates such as sodium methylate. Hexahydrotriazines may also be used as
catalysts.
Organometallic compounds, more especially organo tin compounds, may also
be used as catalysts in accordance with the invention.
Preferred organo tin compounds are tin(II)salts of carboxylic acids, such as
tin(II)acetate, tin(lI)octoate, tin(II)ethyl hexoate and tin(lI)laurate and the tin(IV)
compounds, for example dibutyl tin oxide, dibutyl tin dichloride, dibutyl tin
diacetate, dibutyl tin dilaurate, dibutyl tin maleate or dioctyl tin diacetate. All of
the above-mentioned catalysts may of course also be used in the form of mixtures.
Other representatives of catalysts suitable for use in accordance with the
invention and information on the way in which the catalysts work may be found in
Kunststoff-Handbuch, Vol. VII, by Vieweg und Höchtlen, Carl-Hanser-Verlag, Munich 1966, for. example on pages 96 to 102.
The catalysts are generally used in a quantity of from about 0.001 to 10% by
weight, based on the quantity of polyisocyanate.
Examples of catalysts which accelerate the reaction of the isocyanate groups
with one another and thus promote for example the uret dione-, isocyanurate- or
carbodiimide-forming reaction, are phbspholfne oxide, potassium acetate,
hexahydrotriazine derivatives and pyridine derivatives.
These catalysts are also generally used in a quantity of from about 0.001 to 10%
by weight, based on the quantity of polyisocyanate.
According to the invention, it is also possible to use surface-active additives,
such as emulsifiers and foam stabilisers. Suitable emulsifiers, are, for example, the
sodium salts of castor oil sulphonates or salts of fatty acids with amines, such as
diethylamine oleate or diethanolamine stearate. Alkali or ammonium salts of
sulphonic acids, for example of dodecyl benzene sulphonic acid or dinaphthyl
methane disulphonic acid, or of fatty acids, such as ricinoleic acid, or of polymeric
fatty acids, may also be used as surface-active additives.
Suitable foam stabilisers are, above all, polyether siloxanes, particularly water soluble types. These compounds generally have a structure in which a copolymer of
ethylene oxide and propylene oxide is attached to a polydimethyl siloxane radical.
Foam stabilisers such as these are described, for example, in US Patent
Specifications Nos. 2,834,748; 2,917,480 and 3,629,308.
According to the invention, it is also possible to use reaction retarders, for
example acid-reacting substances, such as hydrochloric acid or organic acid
halides, also cell regulators known per se, such as paraffins or fatty alcohols or
dimethyl polysiloxanes and also pigments or dyes and flame-proofing agents known per se, for example tris-chloroethyl phosphate, tricresyl phosphate or ammonium
phosphate and polyphosphate, also stabilisers against the effects of ageing and
weathering, plasticisers and fungistatic and bacteriostatic substances.
Further examples of surface-active additives and foam stabilisers which may
be used in accordance with the invention and of cell regulators, reaction retarders, stabilisers, flame-proofing agents, plasticisers, dyes, fillers, fungistatic and
bacteriostatic substances, and information on the use of additives such as these and
the way in which they work may be found in Kunststoff-Handbuch, Vol. VII, by
Vieweg und Höchtlen, Carl-Hanser-Verlag, Munich 1966, for example on pages 103
to 113.
According to the invention, it is preferred to work in the absence of water and
in the absence of the usual organic solvents for polyurethanes, such as for example
toluene, ethylacetate or dimethyl formamide. In order to make the reaction
mixtures anhydrous, the usual drying agents, preferably zeolites, may be added.
In general, an index of from 80 to 150, preferably from 90 to 120 (equivalent ratio of isocyanate to hydroxyl and, optionally, amino groups of about 0.8:1 to 1.5:1, preferably 0.9:1 tQ 1.2:1) is maintained in the production of the polyurethane elastomers.
The composite materials may be produced for example by mixing the described components with one another in one or-several stages in a batch-type or continuous mixer and allowing the resulting mixture to react to completion in moulds or on suitable substrates (generally outside the mixer).
Thl processing temperatures may be in the range from 100C to 1500C, although they are preferably in the range from 20"C to 1100C. In a preferred procedure, the components are combined at room temperature and subsequently heated for 10 minutes at 100 to 1100C.
The mixture of components may also be moulded, cast or injection-moulded in cold or heated moulds and left to harden in these moulds, which may be relief moulds, solid moulds or hollow moulds, optionally by centrifugal casting, at room temperature. The final mixtures are used both in foamed and also in non-foamed form, for example as coating materials for fabrics, for example for the backs of carpets, polyvinyl chloride films or sheeting. Coating may be carried out by the following two methods:
1. The material to be coated is allowed to run onto the liquid, smoothed layer
of polyurethane reaction mixture and the material is passed with the
mixture through a heating channel;
2. the reactive polyurethane mixture is applied to the material to be coated by
means of a knife coater.
In-addition to their suitability as carpet backings or PVC coatings, the filler
containing polyurethane mixtures containing sulphonate and/or phosphonate
groups according to the invention may also be used for the production of foamed
products with or without a homogeneous peripheral layer, for example shoe soles,
as shaped articles having a density of from 0.2 to 1.0 g/cc, more especially from 0.3 to 0.8 g/cc or as lightweight foams having a density of from 0.01 to 0.2 g/cc and preferably from 0.02 to 0.1 g/cc. The filler-containing polurethane elastomers
containing sulphonate and phosphonate groups according to the invention may
also be used for the production of seals (for example for air filters of motor vehicles
or for clay tubes), films or tapes, for coating textiles, for sound-damping purposes
or as coating compositions in the building industry.
The process according to the invention is illustrated by the following
Examples. In order to determine whether the improvement in the mechanical
properties is ultimately due to an emulsifying effect of the sulphonic-acid or
phosphonic-acid-group-containing chain extenders used, this possible influence was
investigated first in an unfilled system which, however, represents the basis of the
filled system and compared with the basic mixture. Comparison Examples A to E
show that no such influence exists. In Comparison Examples F to H and Example I,
the possibility of gn emulsifying effect of the ionically modified chain extenders in
filled system was investigated. The mechanical values do not reveal any such effect.
In the interests of clarity, the values obtained from Example A to H and Example I
are additionally set out in Table I.
The influence on mechanical properties of the ionically modified chain
extenders in filler-containing polyurethane elastomers is presumably based on the
ionic interaction between the filler bound in the polyurethane matrix and the ionic
groups incorporated into the polyurethane matrix. The influence of the
quantitative proportion of ionic elements in filler-containing elastomers is
demonstrated in Examples I and 1 to 10.
The improvement in the mechanical properties of the test specimens, for
example tensile strength or tear propagation resistance, where diols containing
sulphonate or phosphonate groups are used is surprising. Where chain extenders
containing ionic groups are used with chalk as the filler, tensile strength is
increased by around 30 to 60%, tear propagation resistance by around 30 to 35%
and hardness by around 5 to 10%, whilst elongation at break and elasticity remain
substantially constant. In the case of the fillers Al (OH)3 and heavy spar, the
improvement in the properties is not quite so pronounced, although it is still
significant.
The limit of error for the measured values quoted in the Examples amounts to
+ 0.06 MPa in the case of tensile strength and to + 0.1 KN/m in the case of tear
propagation resistance.
An improvement in the mechanical properties can also be obtained where
inorganic fillers are used in combination with diols containing ionic groups.
Example A.
(Comparison Example)
90 parts of a trifunctional polyether polyol having a hydroxyl number of 35 and a molecular weight of 4800, produced from trimethylol propane, propylene oxide and ethylene oxide, 10 parts of dipropylene glycol, 31.6 parts of crude 4,4'diisocyanatodiphenyl methane (isocyanate-content 31%), 3 parts of zeolite and 0.3 part of 2,3-dimethyl tetrahydropyrimidine are mixed over a period of 30 seconds (NCO/OH = 1.1) and the reacting mixture is cast into a preheated mould. After tempering for 10 minutes at 1100C, the elastomeric moulding is removed from the mould. The following mechanical values are obtained:
Tensile strength DIN 53504 2.5 MPa
Elongation at break DIN 53504 184%
Tear propagation resistance DIN 53515 5.0 KN/m
Shore hardness A DIN 53505 54
Elasticity DIN 53512 30%
Example B.
(Comparison Example)
90 parts of the polyether polyol described above, 9.35 parts of dipropylene glycol, 2 parts of a polypropylene glycol having a molecular weight of 415 and a hydroxyl number of 270, 31.6 parts of the above diisocyanate (NCO:OH = 1.1), 3 parts of zeolite and 0.3 part of the above pyrimidine derivative are processed in the same way as in Example A. the following mechanical values are obtained:
Tensile strength DIN 53504 2.41 MPa
Elongation at break DIN 53504 139%
Tear propagation resistance DIN 53515 4.35 KN/m
Shore hardness A DIN 53505 53
Elasticity DIN 53512 37
Example C.
(Comparison Example)
The batch from which the elastomeric moulding is produced is the same as in
Example B (NCO:OH = 1:1). However, the polyether polyol having a molecular weight of 415 and a hydroxyl number of 270 used in Example B is replaced by 2 parts of the sulphonated diol.
the following mechanical values are obtained:
Tensile strength DIN 53504 2.53 MPa
Elongation at break DIN 53504 200%
Tear propagation resistance DIN 53515 5.1 KN/m
Shore hardness A DIN 53505 60
Elasticity DIN 53512 31%
Example D.
(Comparison Example)
The batch from which the elastomeric moulding is produced is the same as in
Example A (NCO+OH = 1.1). However, 2 parts of an emulsifier which does not have any hydrogen atoms that are reactive to isocyanates in the sense of the isocyanatepolyaddition reaction (oleic acid oxyethane sulphonate) are also used.
The following values are obtained:
Tensile strength DIN 53504 2.2 MPa
Elongation at break DIN 53504 148%
Tear propagation resistance DIN 53515 4.0 KN/m
Shore hardness A DIN 53505 56
Elasticity DIN 53512 32%
Example E.
(Comparison Example)
The batch from which the elastomer is produced is the same as in Example D, except that 2 parts of diethylaminooleate are used as emulsifier. The following mechanical values are obtained:
Tensile strength DIN 53504 2.25 MPa
Elongation at break DIN 53504 119%
Tear propagation resistance DIN 53515 5.2 KN/m
Shore hardness A DIN 53505 70
Elasticity DIN 53512 37%
Example F.
(Comparison Example)
The reaction mixture is the same as in Example A, except that 100 parts of chalk are used. The chalk is initially stirred uniformly into the polyol mixture over a period of 15 minutes, after which 31.6 parts of the diisocyanate (NCO:OH = 1.1) are added. The mixture is stirred for 30 seconds at room temperature, subsequently introduced into a pre-heated mould, tempered for 10 minutes at 1 lO0C and the elastomeric moulding removed from the mould. The following mechanical values are obtained:
Tensile strength DIN 53504 2.44 MPa
Elongation at break DIN 53504 1.10% Tear propagation resistance DIN 93515 6.35 KN/m
Shore hardness A DIN 53505 75
Elasticity DIN 53512 22%
Example G.
(Comparison Example)
Example D is repeated using 100 parts of chalk (NCO:OH = 1.1). The following mechanical values are obtained:
Tensile strength DIN 53504 2.16 MPa
Elongation at break DIN 53504 1.18%
Tear propagation resistance DIN 53515 6.2 KN/m
Shore hardness A DIN 53505 65
Elasticity DIN 53512 26%
Example H.
(Comparison Example)
Example B is repeated using 100 parts of chalk (NCO:OH = 1.1).
The following mechanical values are obtained:
Tensile strength DIN 53504 2.3 MPa
Elongation at break DIN 53504 117%
Tear propagation resistance DIN 53515 5.99 KN/m
Shore hardness A DIN 53505 75
Elasticity DIN 53512 31%
Example I.
(according to the invention)
Example C is repeated using 100 parts of chalk (NCO:OH = 1.1). The following mechanical values are obtained:
Tensile strength DIN 53504 3.25 MPa
Elongation at break DIN 53504 105%
Tear propagation resistance DIN 53515 9.28 KN/m
Shore hardness A DIN 53505 75
Elasticity DIN 53512 27%
Example 1.
(Comparison Test)
Example F is repeated using 100 parts of Al(OH)3 instead of the chalk (NCO:OH = 1.1). The following mechanical values are obtained:
Tensile strength DIN 53504 2.28 MPa
Elongation at break DIN 53504 98%
Tear propagation resistance DIN 53515 6.67 KN/m
Shore hardness A DIN 53505 77
Elasticity DIN 53512 28%
Example 2.
(according to the invention)
Example I is repeated using 100 parts of Al(OH)3 instead of the chalk (NCO:OH = 1.1). The following mechanical values are obtained:
Tensile strength DIN 53504 2.57 MPa
Elongation at break DIN 53504 86%
Tear propagation resistance DIN 53515 8.31 KN/m
Shore hardness A DIN 53505 75
Elasticity DIN 53512 26%
Example 3.
(Comparison Test)
Example F is repeated using 100 parts of heavy spar instead of the chalk (NCO:OH = 1.1). The following mechanical values are obtained:
Tensile strength DIN 53504 2.48 MPa
Elongation at break DIN 53504 90%
Tear propagation resistance DIN 53515 5.79 KN/m
Shore hardness A DIN 53505 75
Elasticity DIN 53512 28%
Example 4.
(according to the invention)
Example I is repeated using 100 parts of heavy spar instead of the chalk (NCO:OH = 1.1). The following mechanical values are obtained:
Tensile strength DIN 53504 2.85 MPa
Elongation at break DIN 53504 93%
Tear propagation resistance DIN 53515 7.78 KN/m
Shore hardness A DIN 53505 75
Elasticity DIN 53512 26%
Example 5.
(according to the invention)
Example I is repeated using 5 parts of the diol containing sulphonate groups described in Example C and 8.38 parts of dipropylene glycol (NCO:OH = 1.1). The following mechanical values are obtained:
Tensile strength DIN 53504 3.81 MPa
Elongation at break DIN 53504 104%
Tear propagation resistance DIN 53515 10.79 KN/m
Shore hardness A DIN 53505 81
Elasticity DIN 53512 27%
Example 6.
(according to the invention)
Example I is repeated using 10 parts of the diol containing sulphonate groups described in Example C and 6.75 parts of dipropylene glycol (NCO:OH = 1.1). The following mechanical values are obtained:
Tensile strength DIN 53504 3.6 MPa
Elongation at break DIN 53504 97%
Tear propagation resistance DIN 53515 9.38 N
Shore hardness A DIN 53505 86
Elasticity DIN 53512 30%
Example 7.
(according to the invention)
Example I is repeated using 1 part of the diol containing sulphonate groups described in Example C and 9.67 parts of dipropylene glycol (NCO:OH = 1.1). The following mechanical values are obtained:
Tensile strength DIN 53504 3.15 MPa
Elongation at break DIN 53504 94%
Tear propagation resistance DIN 53515 9.48 N
Shore hardness A DIN 53505 80
Elasticity DIN 53512 27%
Example 8.
(according to the invention)
Example 2 is repeated using I part of the diol containing sulphonate groups described in Example C and 9.67 parts of dipropylene glycol. The following mechanical values are obtained:
Tensile strength DIN 53504 2.37 MPa
Elongation at break DIN 53504 90%
Tear propagation resistance DIN 53515 7.79 KN/m
Shore hardness A DIN 53505 75
Elasticity DIN 53512 26%
Example 9.
(according to the invention)
Example 2 is repeated using 5 parts of the diol containing sulphonate groups described in Example C and 8.38 parts of dipropylene glycol. The following values are obtained:
Tensile strength DIN 53504 3.25 MPa
Elongation at break DIN 53504 85%
Tear propagation resistance DIN 53515 9.40 KN/m
Shore hardness A DIN 53505 81
Elasticity DIN 53512 28%
Example 10.
(according to the invention)
Example 4 is repeated using 5 parts of the diol containing sulphonate groups described in Example C and 8.38 parts of dipropylene glycol. The following values are obtained:
Tensile strength DIN 53504 3.49 MPa
Elongation at break DIN 53504 104%
Tear propagation resistance DIN 53515 9.59 KN/m
Shore hardness A DIN 53505 76
Elasticity DIN 53512 26%
Example 11.
(according to the invention)
90 parts of the trifunctional polyether polyol having an OH-number of 35 of
Example A are thoroughly mixed for 15 minutes at room temperature with 8.78 parts of dipropylene glycol, 2 parts of a sulphonate-group-containing diol corresponding to the formula
3 parts of zeolite, 0.3 part of 2,3-dimethyl tetrahydropyrimidine and 100 parts of chalk, followed by the addition of 31.6 parts of the diisocyanate described in
Example A. After stirring for 30 seconds, the mixture is poured into a preheated mould. After tempering for 10 minutes at 1100 C, the moulding is removed from the mould and tested for its mechanical properties. The following mechanical values are obtained:
Tensile strength DIN 53504 3.34 MPa
Elongation at break DIN 53504 109%
Tear propagation resistance DIN 53515 9.67 KN/m
Shore hardness A DIN 53505 87
Elasticity DIN 53512 26%
Example 12.
(according to the invention)
90 parts of the polyether polyol used in Example 7 were mixed with 8.98 parts of dipropylene glycol, 2 parts of a sulphonate-group-containing diol corresponding to the formula
3 parts of zeolite, 0.3 part of the catalyst mentioned in Example 11 and 100 parts of chalk, and the resulting mixture subsequently stirred for 30. seconds with 31.6 parts of the diisocyanate used in Example A. The moulding obtained has the following mechanical values:
Tensile strength DIN 53504 2.91 MPa
Elongation at break DIN 53504 124%
Tear propagation resistance DIN 53515 8.82 KN/m
Shore hardness A DIN 53505 84
Elasticity DIN 53512 25%
Example 13.
(according to the invention)
Example 12 is repeated using 9.5 parts of dipropylene glycol and 2.5 parts of a bisulphonate corresponding to the formula
The following mechanical values are obtained:
Tensile strength DIN 53504 3.79 MPa
Elongation at break DIN 53504 114%
Tear propagation resistance DIN 53515 10.03 KN/m
Shore hardness A DIN 53505 89
Elasticity DIN 53512 20%
Example 14.
(according to the invention)
Example 2 is repeated using 9.7 parts of dipropylene glycol and 2.5 parts of a diol containing two sulphonate groups and corresponding to the formula
The following mechanical values are obtained:
Tensile strength DIN 53504 3.27 MPa
Elongation at break DIN 53504 129%
Tear propagation resistance DIN 53515 9. I I KN/m
Shore hardness A DIN 53505 84
Elasticity DIN 53512 23%
Example 15.
(according to the invention)
Example 12 is repeated using 9.2 parts of dipropylene glycol and 2 parts of a diol containing one phosphonate group and corresponding to the formula
The following mechanical values are obtained:
Tensile strength DIN 53504 2.87 MPa
Elongation at break DIN 53504 148%
Tear propagation resistance DIN 53515 7.42 KN/m
Shore hardness A DIN 53505 81
Elasticity DIN 53512 24%
Example 16.
(Comparison Test)
82 parts of the trifunctional polyether glycol of Example A are mixed for 15 minutes at room temperature with 18 parts of dipropylene glycol, 30 parts of benzyl butyl phthalate, 0.5 part of 2,3-dimethyl tetrahydropyrimidine and 50 parts of PVC powder (particle size: 0.55 y), the resulting mixture is stirred for 30 seconds with 64.3 parts of a reaction product of 4,4'-diisocyanatodiphenyl methane with tripropylene glycol (NCO-content 23%) (NCO:OH = 1.1), the reacting mixture is introduced into a preheated mould, tempered for 10 minutes at 1100C and the moulding produced is removed from the mould. The following mechanical values are obtained:
Tensile strength DIN 53504 3.9 MPa
Elongation at break DIN 53504 322%
Tear propagation resistance DIN 53515 16.7 KN/m
Shore hardness A DIN 53505 84
Elasticity DIN 53512 10% Example 17.
(according to the invention)
Example 16 is repeated using 17.67 parts of dipropylene glycol and 1 part of the chain extender containing sulphonate groups used in Example C (NCO:OH
1.1). The following mechanical values are obtained:
Tensile strength DIN 53504 3.9 MPa
Elongation at break DIN 53504 205%
Tear propagation resistance DIN 53515 20.8 KN/m
Shore hardness A DIN 53505 83
Elasticity DIN 53512 10% Example 18.
(according to the invention)
Example 16 is repeated using 17 parts of dipropylene glycol and 3 parts of the chain extender containing ionic groups of Example C.
Tensile strength DIN 53504 3.94 MPa
Elongation at break DIN 53504 224%
Tear propagation resistance DIN 53515 23.8 KN/m
Shore hardness A DIN 53505 84
Elasticity DIN 53512 11
Example 19.
(according to the invention)
Example 16 is repeated using 16.3 parts of dipropylene glycol and 5 parts of the sulphonated diol of Example C:
Tensile strength DIN 53504 4.60 MPa
Elongation at break DIN 53504 160%
Tear propagation resistance DIN 53515 27.8 KN/m
Shore hardness A DIN 53505 91
Elasticity DIN 53512 15%
Example 20.
(according to the invention)
Example 16 is repeated using 14.8 parts of dipropylene glycol and 10 parts of the sulphonated diol of Example C:
Tensile strength DIN 53504 5.64 MPa
Elongation at break DIN 53504 110% Tear propagation resistance DIN 53515 28.1 KN/m
Shore hardness A DIN 53505 94
Elasticity DIN 53512 19%
Example 21.
(Comparison Test)
Example 16 is repeated using 50 parts of polystyrene powder as filler (particle size < 0.8 ,u) (NCO/OH = 1.1). The following mechanical values are obtained:
Tensile strength DIN 53504 3.25 MPa
Elongation at break DIN 53504 301%
Tear propagation resistance DIN 53515 14.72 KN/m
Shore hardness A DIN 53505 83
Elasticity DIN 53512 11% Example 22.
(according to the invention)
Example 18 is repeated using 50 parts of polystyrene powder (NCO/OH = 1.1).
The following mechanical values are obtained:
Tensile strength DIN 53504 3.67 MPa
Elongation at break i DIN 53504 324%
Tear propagation resistance DIN 53515 22.6 KN/m
Shore hardness A DIN 53505 84
Elasticity DIN 53512 12%
Example 23.
(Comparison Test)
Example 16 is repeated using 50 parts of polyethylene powder as filler (particle size 0.5 ,u) (NCO/OH = 1.1). The following values are obtained:
Tensile strength DIN 53504 3.84 MPa
Elongation at break DIN 53504 335%
Tear propagation resistance DIN 53515 14.22 KN/m
Shore hardness A DIN 53505 81
Elasticity DIN 53512 13%
Example 24.
(according to the invention)
Example 18 is repeated using 50 parts of polyethylene powder (NCO/OH = 1.1). The following mechanical values are obtained:
Tensile strength DIN 53504 4.01 MPa
Elongation at break DIN 53504 232%
Tear propagation resistance DIN 53505 21.5 KN/m Shore hardness A DIN 53505 82
Elasticity DIN 53512 13 TABLE I Synoptic Table of the mechanical values of the unfilled elastomers by comparison with filled elastomers.
Example A B C D E F G H I Parts of polyether, OHnumber 35 90 90 90 90 90 90 90 90 90 Parts of dipropylene glycol 10 9.35 9.35 10 10 10 10 9.35 9.35 Parts of diisocyanate 31.6 31.6 31.6 31.6 31.6 31.6 31.6 31.6 31.6 Parts of polyether, OHnumber 270 - 2 - - - - - 2 Parts of ionically modified diol - - 2 - - - - - 2 Parts of oleic acid oxythane - - - 2 - - 2 - sulphonate Parts of diethylaminooleate - - - - 2 - - - Parts of 2,3-dimethyl tetrahydropyrimidine 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 Parts of zeolite 3 3 3 3 3 3 3 3 3 Parts of chalk - - - - - 100 100 100 100 Tensile strength (MPa) 2.5 2.41 2.53 2.2 2.25 2.44 2.16 2.3 3.25 Elongation at break (%) 184 139 200 148 119 110 118 117 105 Tear propagation resistance (KN/m) 5.0 4.35 5.1 4.0 5.2 6.35 6.2 5.99 9.28 Shore hardness A 54 53 60 56 70 75 65 75 75 Elasticity (%) 30 37 31 32 37 22 26 31 27 TABLE II Mechanical values of filler-containing elastomers in dependence upon the quantity of ionically modified diol used.
Examples
Parts of polyether (OH-number 35)
Parts of dipropylene glycol
Parts of diisocyanate
Parts of ionically modified diol
Parts of 2,3-dimethyl tetrahydropyrimidine
Parts of zeolite
Parts of chalk
Parts of Al(OH)3
Parts of heavy spar
Tensile strength (MPa)
Elongation at break (%)
Tear propagation resistance (KN/m)
Shore hardness A
Elasticity (%) I 1 2 3 4 5 6 7 8 9 10 F 90 90 90 90 90 90 90 90 90 90 90 90 9.35 10 9.35 10 9.35 8.35 6.75 9.76 9.76 8.38 8.38 10 31.6 31.6 31.6 31.6 31.6 31.6 31.6 31.6 31.6 31.6 31.6 31.6 2 - 2 - 2 5 10 1 1 5 5 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 3 3 3 3 3 3 3 3 3 3 3 3 100 - - - - 100 100 100 - - - 100 - 100 100 - - - - - 100 100 - - - - 100 100 - - - - - 100 3.25 2.28 2.57 2.48 2.85 3.81 3.6 3.15 2.37 3.25 3.49 2.44 105 98 86 90 93 104 97 94 90 85 104 110 9.28 6.67 8.31 5.79 7.78 10.79 9.38 9.48 7.79 9.40 9.59 6.35 75 77 75 75 75 81 86 80 75 81 76 75 27 28 26 28 26 27 30 27 26 28 26 22
Claims (8)
1. A process for the production of an optionally foamed filler-containing polyurethane elastomer by reacting together (a) a compound containing at least 2 Zerewitinoff-active hydrogen atoms and
having a molecular weight of from 400 to 10,D00, (b) an organic polyisocyanate, optionally (c) a chain extender having a molecular weight of from 32 to 400, (d) 50 to 500 parts by weight, based on 100 parts by weight of polyurethane solids,
of an organic or inorganic filler and optionally (e) blowing agents, catalysts and other auxiliaries and additives, wherein a polyhydroxyl compound containing at least one sulphonate and/or phosphonate group is used as at least part of component (a) and/or (c) in such a quantity that the polyurethane elastomer contains from I to-10% by weight of sulphonate and/or phosphonate groups based on 100% by weight of polyurethane solids.
2. A process as claimed in Claim 1, wherein the sulphonate-group-containing polyol used correspond to the general formula
in which
A and B which may be the same or different represent difunctional aliphatic hydrocarbon radicals containing from I to 6 carbon atoms,
R represents hydrogen, an aliphatic hydrocarbon radical containing from I to 4 carbon atoms or a phenyl radical,
X'+' represents an alkali metal cation or an ammonium group, which may be substituted,
n and m which may be the same or different are integers from 0 to 30,
o and p = 0 or 1 and
q is an integer from 0 to 2.
3. A process as claimed in Claim 1, wherein the sulphonate-group-containing polyol used corresponds to the general formula
in which
X'+' represents an alkali metal cation or an ammonium group which may be substituted and
n and m which may be the same or different are integers from I to 6 and
p is an integer from 1 to 4.
4. A process as claimed in Claim 1, wherein the sulphonate-group-containing polyol used corresponds to the general formula
in which
R represents an alkylene radical containing from 2 to 4 carbon atoms and/or a difunctional aromatic or araliphatic radical containing from 6 to 15 carbon atoms,
X'+' represents an alkali metal cation or an ammonium group, which may be substituted, R1 and R2 represent hydrogen and/or the same or different alkyl radicals containing from I to 6 carbon atoms and
m and n which may be the same or different are integers from I to 6.
5. A process as claimed in Claim 1, wherein the phosphonate-group-containing polyol used corresponds to the general formula
in which
R represents a hydrogen atom or an alkyl radical containing from 1 to 4 carbon atoms or a phenyl radical, X'+' represents an alkali metal cation or an ammonium group which may be substituted and
n is an integer from 1 to 4.
6. A process as claimed in Claims 1 to 5, wherein the sulphonate- or phosphonate-group-containing polyhydroxyl compound used contains from 60 to 70 milliequivalents per 100 g of anionic groups.
7. A process as claimed in Claims I to 6, wherein a filler having a particle diameter of from 0.01 y to 1000y is used.
8. A process as claimed in Claims I to 7, wherein a CaCO,--, BaSO4- or Al(OH)3-powder and/or a polyvinyl chloride-, polyethylene- or polystyrenegranulate is used as the filler component.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19772719372 DE2719372A1 (en) | 1977-04-30 | 1977-04-30 | PROCESS FOR THE PRODUCTION OF FILLER-REINFORCED POLYURETHANE ELASTOMERS |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1587046A true GB1587046A (en) | 1981-03-25 |
Family
ID=6007724
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB16932/78A Expired GB1587046A (en) | 1977-04-30 | 1978-04-28 | Process for the production of filler-reinforced polyurethane elastomers |
Country Status (5)
Country | Link |
---|---|
BE (1) | BE866523A (en) |
DE (1) | DE2719372A1 (en) |
FR (1) | FR2388856A1 (en) |
GB (1) | GB1587046A (en) |
IT (1) | IT1104192B (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0175927A2 (en) * | 1984-08-21 | 1986-04-02 | Tosoh Corporation | Process for producing elastomeric polyurethane foams of reduced weight |
WO2018111806A1 (en) * | 2016-12-15 | 2018-06-21 | Dow Global Technologies Llc | Polyurethane product with sulfur-containing polyol |
CN112250820A (en) * | 2020-10-21 | 2021-01-22 | 盐城市恒丰海绵有限公司 | Sinking-bottom expanded polyurethane with high tearing property and preparation method thereof |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3531660A1 (en) * | 1985-09-05 | 1987-03-12 | Bayer Ag | MOLDED PLASTICS BASED ON POLYURETHANE, A METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FOOTWEAR |
US4738992A (en) * | 1985-12-09 | 1988-04-19 | Minnesota Mining And Manufacturing Company | Hydrophilic polyurethane/polyurea sponge |
JP2584672B2 (en) * | 1989-04-28 | 1997-02-26 | 富士写真フイルム株式会社 | Photosensitive composition |
JPH0372515A (en) * | 1989-05-10 | 1991-03-27 | Asahi Glass Co Ltd | Production of rigid foam |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1570615C3 (en) * | 1965-10-16 | 1975-05-28 | Bayer Ag, 5090 Leverkusen | Process for the production of dispersible polyurethanes |
-
1977
- 1977-04-30 DE DE19772719372 patent/DE2719372A1/en not_active Withdrawn
-
1978
- 1978-04-28 IT IT49129/78A patent/IT1104192B/en active
- 1978-04-28 BE BE187231A patent/BE866523A/en not_active IP Right Cessation
- 1978-04-28 FR FR7812749A patent/FR2388856A1/fr active Pending
- 1978-04-28 GB GB16932/78A patent/GB1587046A/en not_active Expired
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0175927A2 (en) * | 1984-08-21 | 1986-04-02 | Tosoh Corporation | Process for producing elastomeric polyurethane foams of reduced weight |
EP0175927B1 (en) * | 1984-08-21 | 1992-07-01 | Tosoh Corporation | Process for producing elastomeric polyurethane foams of reduced weight |
WO2018111806A1 (en) * | 2016-12-15 | 2018-06-21 | Dow Global Technologies Llc | Polyurethane product with sulfur-containing polyol |
CN110023366A (en) * | 2016-12-15 | 2019-07-16 | 陶氏环球技术有限责任公司 | Use the polyurethane products of sulfur-bearing polyalcohol |
CN110023366B (en) * | 2016-12-15 | 2022-04-01 | 陶氏环球技术有限责任公司 | Polyurethane products using sulfur-containing polyols |
CN112250820A (en) * | 2020-10-21 | 2021-01-22 | 盐城市恒丰海绵有限公司 | Sinking-bottom expanded polyurethane with high tearing property and preparation method thereof |
Also Published As
Publication number | Publication date |
---|---|
BE866523A (en) | 1978-10-30 |
IT7849129A0 (en) | 1978-04-28 |
IT1104192B (en) | 1985-10-21 |
DE2719372A1 (en) | 1978-11-02 |
FR2388856A1 (en) | 1978-11-24 |
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PS | Patent sealed [section 19, patents act 1949] | ||
PCNP | Patent ceased through non-payment of renewal fee |