CN109503809B - 含有磷化合物的聚氨酯泡沫 - Google Patents
含有磷化合物的聚氨酯泡沫 Download PDFInfo
- Publication number
- CN109503809B CN109503809B CN201811366606.1A CN201811366606A CN109503809B CN 109503809 B CN109503809 B CN 109503809B CN 201811366606 A CN201811366606 A CN 201811366606A CN 109503809 B CN109503809 B CN 109503809B
- Authority
- CN
- China
- Prior art keywords
- polyurethane foam
- phosphate
- groups
- bis
- group
- 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.)
- Active
Links
- 229920005830 Polyurethane Foam Polymers 0.000 title claims abstract description 50
- 239000011496 polyurethane foam Substances 0.000 title claims abstract description 50
- 150000003018 phosphorus compounds Chemical class 0.000 title description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 50
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 41
- 229920000642 polymer Polymers 0.000 claims abstract description 18
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 17
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 17
- 239000004604 Blowing Agent Substances 0.000 claims abstract description 15
- 150000001412 amines Chemical class 0.000 claims abstract description 15
- 239000011541 reaction mixture Substances 0.000 claims abstract description 15
- 239000004970 Chain extender Substances 0.000 claims abstract description 13
- 229920000388 Polyphosphate Polymers 0.000 claims abstract description 12
- 239000001205 polyphosphate Substances 0.000 claims abstract description 12
- 235000011176 polyphosphates Nutrition 0.000 claims abstract description 12
- 239000004971 Cross linker Substances 0.000 claims abstract description 11
- 238000002156 mixing Methods 0.000 claims abstract description 8
- 239000000654 additive Substances 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- -1 N, N-dimethyl-3-aminopropyl Chemical group 0.000 claims description 51
- 229910052757 nitrogen Inorganic materials 0.000 claims description 36
- 150000003077 polyols Chemical class 0.000 claims description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
- 229920005862 polyol Polymers 0.000 claims description 30
- 239000010452 phosphate Substances 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
- 239000000460 chlorine Substances 0.000 claims description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 239000011737 fluorine Substances 0.000 claims description 14
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 13
- 125000001931 aliphatic group Chemical group 0.000 claims description 11
- 239000006260 foam Substances 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 9
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 238000005253 cladding Methods 0.000 claims description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- 239000003063 flame retardant Substances 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- GXVUZYLYWKWJIM-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanamine Chemical compound NCCOCCN GXVUZYLYWKWJIM-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 229940102253 isopropanolamine Drugs 0.000 claims description 4
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 claims description 3
- JZRJVXYQKBRUMY-UHFFFAOYSA-N 2-[bis[3-(dimethylamino)propyl]amino]ethanol Chemical compound CN(C)CCCN(CCO)CCCN(C)C JZRJVXYQKBRUMY-UHFFFAOYSA-N 0.000 claims description 3
- KRPRVQWGKLEFKN-UHFFFAOYSA-N 3-(3-aminopropoxy)propan-1-amine Chemical compound NCCCOCCCN KRPRVQWGKLEFKN-UHFFFAOYSA-N 0.000 claims description 3
- ROBICTHFFIVQEQ-UHFFFAOYSA-N 3-n,3-n,6-n,6-n-tetramethylhexane-1,3,6-triamine Chemical compound CN(C)CCCC(N(C)C)CCN ROBICTHFFIVQEQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 3
- 229940043276 diisopropanolamine Drugs 0.000 claims 2
- 230000000996 additive effect Effects 0.000 claims 1
- 239000012752 auxiliary agent Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229920001281 polyalkylene Polymers 0.000 claims 1
- 235000021317 phosphate Nutrition 0.000 abstract description 27
- 229920002635 polyurethane Polymers 0.000 abstract description 27
- 239000004814 polyurethane Substances 0.000 abstract description 27
- 239000012948 isocyanate Substances 0.000 abstract description 17
- 150000002513 isocyanates Chemical class 0.000 abstract description 17
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract description 9
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 abstract description 8
- 150000003013 phosphoric acid derivatives Chemical class 0.000 abstract description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 24
- 230000032683 aging Effects 0.000 description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 12
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 238000006068 polycondensation reaction Methods 0.000 description 6
- 229920000570 polyether Polymers 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 5
- 239000004114 Ammonium polyphosphate Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 235000011037 adipic acid Nutrition 0.000 description 4
- 229920001276 ammonium polyphosphate Polymers 0.000 description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 229920005906 polyester polyol Polymers 0.000 description 4
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 3
- OWXJKYNZGFSVRC-NSCUHMNNSA-N (e)-1-chloroprop-1-ene Chemical compound C\C=C\Cl OWXJKYNZGFSVRC-NSCUHMNNSA-N 0.000 description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 3
- 229940035437 1,3-propanediol Drugs 0.000 description 3
- DUDKKPVINWLFBI-UHFFFAOYSA-N 1-chlorobut-1-ene Chemical compound CCC=CCl DUDKKPVINWLFBI-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000019826 ammonium polyphosphate Nutrition 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 150000002605 large molecules Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000003014 phosphoric acid esters Chemical class 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 125000001302 tertiary amino group Chemical group 0.000 description 3
- 150000004072 triols Chemical class 0.000 description 3
- KVMPUXDNESXNOH-UHFFFAOYSA-N tris(1-chloropropan-2-yl) phosphate Chemical compound ClCC(C)OP(=O)(OC(C)CCl)OC(C)CCl KVMPUXDNESXNOH-UHFFFAOYSA-N 0.000 description 3
- WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 3
- FCQPNTOQFPJCMF-UHFFFAOYSA-N 1,3-bis[3-(dimethylamino)propyl]urea Chemical compound CN(C)CCCNC(=O)NCCCN(C)C FCQPNTOQFPJCMF-UHFFFAOYSA-N 0.000 description 2
- 229940043375 1,5-pentanediol Drugs 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000002666 chemical blowing agent Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000013016 damping Methods 0.000 description 2
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical compound COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 description 2
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- MGMXGCZJYUCMGY-UHFFFAOYSA-N tris(4-nonylphenyl) phosphite Chemical compound C1=CC(CCCCCCCCC)=CC=C1OP(OC=1C=CC(CCCCCCCCC)=CC=1)OC1=CC=C(CCCCCCCCC)C=C1 MGMXGCZJYUCMGY-UHFFFAOYSA-N 0.000 description 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- ZFDWWDZLRKHULH-UHFFFAOYSA-N 1,2-dimethyl-5,6-dihydro-4h-pyrimidine Chemical compound CN1CCCN=C1C ZFDWWDZLRKHULH-UHFFFAOYSA-N 0.000 description 1
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- GEEGPFGTMRWCID-UHFFFAOYSA-N 1-n,1-n,1-n',1-n'-tetramethylbutane-1,1-diamine Chemical compound CCCC(N(C)C)N(C)C GEEGPFGTMRWCID-UHFFFAOYSA-N 0.000 description 1
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 1
- CVFRFSNPBJUQMG-UHFFFAOYSA-N 2,3-bis(2-hydroxyethyl)benzene-1,4-diol Chemical compound OCCC1=C(O)C=CC(O)=C1CCO CVFRFSNPBJUQMG-UHFFFAOYSA-N 0.000 description 1
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
- BJKRRLWNBFNWNA-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]ethyl carbamate Chemical compound CN(C)CCOCCOC(N)=O BJKRRLWNBFNWNA-UHFFFAOYSA-N 0.000 description 1
- NCUPDIHWMQEDPR-UHFFFAOYSA-N 2-[2-[2-(dimethylamino)ethoxy]ethyl-methylamino]ethanol Chemical compound CN(C)CCOCCN(C)CCO NCUPDIHWMQEDPR-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- IIVBUJGYWCCLNG-UHFFFAOYSA-N 3-(dimethylamino)propylurea Chemical compound CN(C)CCCNC(N)=O IIVBUJGYWCCLNG-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- HHDUMDVQUCBCEY-UHFFFAOYSA-N 4-[10,15,20-tris(4-carboxyphenyl)-21,23-dihydroporphyrin-5-yl]benzoic acid Chemical compound OC(=O)c1ccc(cc1)-c1c2ccc(n2)c(-c2ccc(cc2)C(O)=O)c2ccc([nH]2)c(-c2ccc(cc2)C(O)=O)c2ccc(n2)c(-c2ccc(cc2)C(O)=O)c2ccc1[nH]2 HHDUMDVQUCBCEY-UHFFFAOYSA-N 0.000 description 1
- BRKHZWFIIVVNTA-UHFFFAOYSA-N 4-cyclohexylmorpholine Chemical compound C1CCCCC1N1CCOCC1 BRKHZWFIIVVNTA-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- CQQXCSFSYHAZOO-UHFFFAOYSA-L [acetyloxy(dioctyl)stannyl] acetate Chemical compound CCCCCCCC[Sn](OC(C)=O)(OC(C)=O)CCCCCCCC CQQXCSFSYHAZOO-UHFFFAOYSA-L 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 150000001279 adipic acids Chemical class 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000000022 bacteriostatic agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- NUMHJBONQMZPBW-UHFFFAOYSA-K bis(2-ethylhexanoyloxy)bismuthanyl 2-ethylhexanoate Chemical compound [Bi+3].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O NUMHJBONQMZPBW-UHFFFAOYSA-K 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- FNYKAWJEEWSNEH-UHFFFAOYSA-K bismuth;3,3,5,5-tetramethylhexanoate Chemical compound [Bi+3].CC(C)(C)CC(C)(C)CC([O-])=O.CC(C)(C)CC(C)(C)CC([O-])=O.CC(C)(C)CC(C)(C)CC([O-])=O FNYKAWJEEWSNEH-UHFFFAOYSA-K 0.000 description 1
- ZZUFUNZTPNRBID-UHFFFAOYSA-K bismuth;octanoate Chemical compound [Bi+3].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O ZZUFUNZTPNRBID-UHFFFAOYSA-K 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000005056 compaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- ZHMPXIDAUXCKIQ-UHFFFAOYSA-N cyclohexane-1,2,4-triol Chemical compound OC1CCC(O)C(O)C1 ZHMPXIDAUXCKIQ-UHFFFAOYSA-N 0.000 description 1
- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 description 1
- FSDSKERRNURGGO-UHFFFAOYSA-N cyclohexane-1,3,5-triol Chemical compound OC1CC(O)CC(O)C1 FSDSKERRNURGGO-UHFFFAOYSA-N 0.000 description 1
- RLMGYIOTPQVQJR-UHFFFAOYSA-N cyclohexane-1,3-diol Chemical compound OC1CCCC(O)C1 RLMGYIOTPQVQJR-UHFFFAOYSA-N 0.000 description 1
- VKONPUDBRVKQLM-UHFFFAOYSA-N cyclohexane-1,4-diol Chemical compound OC1CCC(O)CC1 VKONPUDBRVKQLM-UHFFFAOYSA-N 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 1
- PNOXNTGLSKTMQO-UHFFFAOYSA-L diacetyloxytin Chemical compound CC(=O)O[Sn]OC(C)=O PNOXNTGLSKTMQO-UHFFFAOYSA-L 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 239000012971 dimethylpiperazine Substances 0.000 description 1
- 229940113120 dipropylene glycol Drugs 0.000 description 1
- PYBNTRWJKQJDRE-UHFFFAOYSA-L dodecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O PYBNTRWJKQJDRE-UHFFFAOYSA-L 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- PLONEVHFXDFSLA-UHFFFAOYSA-N ethyl hexanoate;tin(2+) Chemical compound [Sn+2].CCCCCC(=O)OCC PLONEVHFXDFSLA-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000010097 foam moulding Methods 0.000 description 1
- 239000004872 foam stabilizing agent Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- 150000002311 glutaric acids Chemical class 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 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
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle 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
- 229960004624 perflexane Drugs 0.000 description 1
- ZJIJAJXFLBMLCK-UHFFFAOYSA-N perfluorohexane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZJIJAJXFLBMLCK-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- ADRDEXBBJTUCND-UHFFFAOYSA-N pyrrolizidine Chemical compound C1CCN2CCCC21 ADRDEXBBJTUCND-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000013040 rubber vulcanization Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 150000003752 zinc compounds Chemical class 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
- C08G18/3882—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus having phosphorus bound to oxygen only
- C08G18/3885—Phosphate compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
- C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
-
- 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
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/1808—Catalysts containing secondary or tertiary amines or salts thereof having alkylene polyamine 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
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/1825—Catalysts containing secondary or tertiary amines or salts thereof having hydroxy or primary amino 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
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4072—Mixtures of compounds of group C08G18/63 with other macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/63—Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers
- C08G18/632—Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers onto polyethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/797—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing carbodiimide and/or uretone-imine groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/0014—Use of organic additives
- C08J9/0038—Use of organic additives containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
- C08J9/125—Water, e.g. hydrated salts
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/32—Phosphorus-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0041—Foam properties having specified density
- C08G2110/0066—≥ 150kg/m3
-
- 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
- C08G2110/0083—Foam properties prepared using water as the sole blowing agent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/32—Phosphorus-containing compounds
- C08K2003/321—Phosphates
- C08K2003/322—Ammonium phosphate
- C08K2003/323—Ammonium polyphosphate
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)
- Materials Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
本发明涉及聚氨酯,其通过混合以下组分得到反应混合物、并使所述反应混合物反应以得到聚氨酯泡沫而获得:(a)多异氰酸酯,(b)具有对异氰酸酯具有反应活性的基团的聚合物,(c)包含可结合的胺催化剂的催化剂,(d)磷酸酯、多磷酸盐、膦酸酯和/或亚磷酸酯,以及任选地(e)发泡剂,(f)增链剂和/或交联剂,以及(g)助剂和/或添加剂。本发明还涉及一种制备这种聚氨酯泡沫的方法以及其在汽车内饰中的用途。
Description
本申请是申请日为2013年7月16日,申请号为201380039946.2,发明名称为“含有磷化合物的聚氨酯泡沫”的发明专利申请的分案申请。
本发明涉及聚氨酯泡沫,其通过混合以下组分得到反应混合物、并完成所述反应混合物的反应以得到聚氨酯而获得:(a)多异氰酸酯,(b)具有对异氰酸酯具有反应活性的基团的聚合物,(c)包含可结合的胺催化剂(incorporable amine catalyst)的催化剂,(d)磷酸酯、多磷酸盐、膦酸酯和/或亚磷酸酯,(e)含水的发泡剂,和任选地(f)增链剂和/或交联剂,以及(g)助剂和/或添加剂;其中磷酸酯具有的通式为
(R1-O)3-P=O,
其中三个R1部分相互独立地为有机部分,其包括一个或多个苯基、一个或多个磷酸基团或其酯和/或一个或多个选自以下的原子:氮、氧、氟、氯和溴;多磷酸盐具有的通式为
–[P(O)(O-R‘+)-O]n-,
其中n为2至10000的整数,R‘+为碱金属阳离子或铵阳离子;膦酸酯具有的通式为
(R3)(R2-O)2-P=O,
其中R2部分相互独立地为有机部分,其包括一个或多个选自以下的原子:氮、氧、氟、氯和溴,R3部分为氢或具有1至10个碳原子的芳族、脂族、或脂环族部分,且还可包括杂原子;亚磷酸酯具有的通式为
(R4-O)3-P,
其中R4部分相互独立地为有机部分,其包括一个或多个选自以下的原子:氮、氧、氟、氯和溴。本发明还涉及一种制备这些聚氨酯泡沫的方法以及其在汽车内饰中的用途。
聚氨酯的特点之一是其具有多种广泛可能的用途。这些材料通常尤其用于汽车构造中,例如用于汽车外壳中作为扰流板(spoiler)、车顶元件或弹性元件(springelement),也用于汽车内饰包层中作为车顶包层(roof cladding)、地毯的泡沫底衬、门包层、方向盘、操控按钮以及座垫。用于汽车行业特别是汽车内饰中的聚氨酯,要满足机械性能的严格要求,以及耐老化性的严格要求:在汽车的整个寿命中,重要的特性(如隔音特性、减震特性或阻尼特性)在机械撞击的事件中(例如事故中)必须保留。
汽车中普遍条件是极端的,并加速聚氨酯的老化:温度达到-10℃且更低,以及也高于60℃,在太阳辐射的条件下甚至达到高于100℃。相对湿度可最高达100%。与致密的聚氨酯相比,该情形尤其出现于具有显著增加的表面积的聚氨酯泡沫中。
除了所述温度和湿度的极端条件外,另一个要求为最小限度地排放出由在汽车内饰中使用的聚氨酯产生的易挥发的化合物。这大部分衍生自所使用的易挥发的胺催化剂。为了减少这种排放物,所述易挥发的胺催化剂被可结合的催化剂完全取代或一定程度地取代。这些化合物催化了聚氨酯反应,但与此同时也具有对异氰酸酯基具有反应活性的基团,该催化剂因此牢固地结合到聚氨酯上。然而,所述可结合的催化剂大部分对最终得到的聚氨酯的机械性能有损害,特别是在热老化和湿热老化后,即一类在汽车内饰中经常发生的极端条件下。
阻燃剂在聚氨酯中的用途是已知的:WO 2009065826描述了磷酸烷基酯用于制备整体聚氨酯泡沫(integral polyurethane foam)的用途,特别是用作方向盘的用途。WO2009065826并没有描述可结合的催化剂与磷酸酯结合的用途。
此外,EP 2374843描述了磷酸酯用于改善由聚氨酯制成的电缆护套的抗老化性的用途。在该文献中指定锌化合物和硼化合物作为有效成分。
本发明的一个目的为改善包含可结合的催化剂的聚氨酯泡沫的老化特性,特别是改善热老化特性和湿热老化特性,且对老化后总体机械性能没有任何的实质性损害。
所述目的通过如下获得的聚氨酯泡沫而实现:通过混合(a)多异氰酸酯,(b)具有对异氰酸酯具有反应活性的基团的聚合物,(c)包含可结合的胺催化剂的催化剂,(d)磷酸酯、多磷酸盐、膦酸酯和/或亚磷酸酯,和任选地(e)含水的发泡剂,(f)增链剂和/或交联剂,以及(g)助剂和/或添加剂以形成反应混合物,并完成所述反应混合物的反应以获得聚氨酯,其中磷酸酯具有的通式为
(R1-O)3-P=O,
其中三个R1部分相互独立地为包含一个或多个苯基、一个或多个磷酸基团或其酯和/或一个或多个选自氮、氧、氟、氯和溴的原子的有机部分;多磷酸盐具有的通式为
–[P(O)(O-R‘+)-O]n-,
其中n为2至10000的整数,R‘+为碱金属阳离子或铵阳离子;膦酸酯具有的通式为
(R3)(R2-O)2-P=O,
其中R2部分相互独立地为包含一个或多个选自氮、氧、氟、氯和溴的原子的有机部分,R3部分为氢或具有1至10个碳原子的芳族、脂族、或脂环族部分;亚磷酸酯具有的通式为
(R4-O)3-P,
其中R4部分相互独立地为包含一个或多个选自氮、氧、氟、氯和溴的原子的有机部分。
本发明的聚氨酯包括聚氨酯泡沫,特别优选模塑的聚氨酯泡沫。具体而言,本发明的聚氨酯包括整体泡沫,特别是那些根据DIN7726、带有由于成形过程而使外周区域比芯部具有更高密度的整体泡沫。
本发明聚氨酯泡沫的平均密度优选100至800g/L,特别优选150至500g/L,特别是200至400g/L。如果所述泡沫具有表皮,则本文的密度涉及整个泡沫模塑物的平均密度,即整个芯部和外周区域的平均密度。
用于制备本发明的整体聚氨酯泡沫的有机和/或改性的多异氰酸酯(a)包括主要来自现有技术的脂族、脂环族和芳族二或多官能的异氰酸酯(成分a-1),及其任何所需的混合物。其实例为二苯基甲烷4,4’-二异氰酸酯、二苯基甲烷2,4’-二异氰酸酯、二苯基甲烷二异氰酸酯单体的混合物、具有更多环的二苯基甲烷二异氰酸酯同系物(聚合物MDI)、四亚甲基二异氰酸酯、六亚甲基二异氰酸酯(HDI)、异佛尔酮二异氰酸酯(IPDI)、2,4-和/或2,6-甲苯二异氰酸酯(TDI)、以及提到的异氰酸酯的混合物。
优选使用4,4’-MDI。优选使用的4,4’-MDI可包含0至20重量%的2,4’-MDI和少量的、最高达20重量%的被脲基甲酸酯或脲酮亚胺(uretonimine)改性的多异氰酸酯。也可以使用少量的聚亚苯基聚亚甲基多异氰酸酯(聚合物MDI)。所述高官能度的多异氰酸酯的总量不应该超过所使用的异氰酸酯重量的5%。
多异氰酸酯组分(a)优选以多异氰酸酯预聚物的形式使用。所述多异氰酸酯预聚物通过上述多异氰酸酯(a-1)与多元醇(a-2)反应得到预聚物而获得,例如在30至100℃的温度,优选温度约80℃下反应。优选通过使用4,4’-MDI和脲酮亚胺改性的MDI以及市售的基于聚酯的多元醇(例如起始物质为己二酸)或基于聚醚的多元醇(起始物质为环氧乙烷和/或环氧丙烷)制备本发明的预聚物。
多元醇(a-2)为本领域普通技术人员所已知,且记载于例如“Kunststoffhandbuch,Band 7,Polyurethane”[Plastics handbook,第7卷,Polyurethanes],Carl Hanser Verlag,1993第三版,第3.1章。本文优选使用的多元醇(a-2)为下文描述为b)且具有对异氰酸酯具有反应活性的氢原子的高分子量的化合物。特别优选使用聚酯作为多元醇(a-2)。
在制备异氰酸酯预聚物时,任选加入常规的增链剂或交联剂至提到的多元醇中。这些物质在下文中描述为c)。特别优选使用单乙二醇和1,4-丁二醇作为增链剂。
具有至少两个对异氰酸酯基团有反应活性的氢原子的相对高分子量的化合物b),可例如为聚醚醇或聚酯醇。
聚醚醇通过已知的方法制备,例如通过使用碱金属氢氧化物或碱金属醇盐作为催化剂、且添加至少一种包含2至3个反应性氢原子的起始分子的阴离子聚合反应来制备,或通过使用路易斯酸(如五氯化锑或三氟化硼醚化物)、由一种或多种在亚烷基部分具有2至4个碳原子的烯化氧的阳离子聚合反应制备。适合的烯化氧的实例为四氢呋喃、1,3-环氧丙烷、1,2-环氧丁烷、2,3-环氧丁烷,优选环氧乙烷和1,2-环氧丙烷。其它可以使用的催化剂为多金属氰化物化合物,被称为DMC催化剂。烯化氧可以单独使用、交替连贯地使用,或以其混合物的形式使用。优选使用1,2-环氧丙烷和环氧乙烷,其中10至50%用量的环氧乙烷用作环氧乙烷端基封闭("EO帽"),使得最终的多元醇具有超过70%的伯OH端基。
可以使用的起始分子为水或二-或三元醇,例如乙二醇、1,2-或1,3-丙二醇、二乙二醇、二丙二醇、1,4-丁二醇、甘油或三羟甲基丙烷。
聚醚多元醇、优选聚氧丙烯聚氧乙烯多元醇的官能度优选为2至3,其分子量为1000至8000g/mol,优选2000至6000g/mol。
聚酯多元醇可例如由具有2至12个碳原子的有机二羧酸、优选具有4至6个碳原子的脂族二羧酸和具有2至12个、优选具有2至6个碳原子的多元醇、优选二醇来制备。可使用的二羧酸的实例为:琥珀酸、戊二酸、己二酸、辛二酸、壬二酸、癸二酸、十二烷二酸、马来酸、富马酸、邻苯二甲酸、间苯二甲酸、对苯二甲酸。本文二羧酸不仅可以单独使用,而且可以彼此混合使用。也可使用相应的二元羧酸衍生物替代游离的二元羧酸,例如具有1至4个碳原子的醇的二元羧酸酯或二元羧酸酐。优选使用定量比例例如为20至35:35至50:20至32重量份的琥珀酸、戊二酸和己二酸的二羧酸混合物,特别优选使用己二酸。二元醇和多元醇、特别是二醇的实例为:乙二醇、二乙二醇、1,2-丙二醇、1,3-丙二醇、二丙二醇、1,4-丁二醇、1,5-戊二醇、1,6-己二醇、1,10-癸二醇、甘油和三羟甲基丙烷。优选使用乙二醇、二乙二醇、1,4-丁二醇、1,5-戊二醇和1,6-己二醇。其它可以使用的化合物为衍生自内酯(如-己内酯)或羟基羧酸(如-羟基己酸)的聚酯多元醇。
为了制备聚酯多元醇,有机的如芳族和优选脂族的多元羧酸和/或其衍生物以及多元醇,可以在没有催化剂或优选在酯化催化剂存在的条件下,有利地在惰性气体(例如氮气、一氧化碳、氦气、氩气)气氛下,特别在150至250℃,优选180至220℃的熔融温度下,任选地在降低的压力下进行缩聚反应,直到已经达到所期望的酸值,此酸值优选低于10,特别优选低于2。在一个优选的实施方案中,所述酯化混合物在上述温度下并在大气压下进行缩聚反应,直到酸值80至30,优选40至30,然后在压力低于500mbar下、优选50至150mbar进行缩聚反应。可以使用的酯化催化剂为金属形式、金属氧化物形式或金属盐形式的铁催化剂、镉催化剂、钴催化剂、铅催化剂、锌催化剂、锑催化剂、镁催化剂、钛催化剂以及锡催化剂。然而,缩聚反应也可以在稀释剂和/或夹带剂(entrainer)(例如苯、甲苯、二甲苯或氯苯)存在的条件下在液相中进行,稀释剂和/或夹带剂用以通过共沸蒸馏除去缩聚反应产生的水。为了制备聚酯多元醇,有机多元羧酸和/或其衍生物以及多元醇有利地以1:1至1.8,优选1:1.05至1.2的摩尔比进行缩聚反应。
所得的聚酯多元醇优选具有官能度为2至4,特别是2至3,且数均分子量为450至3000g/mol,优选1000至3000g/mol。
其它合适的具有至少两个对异氰酸酯有反应活性的氢原子的相对高分子量的化合物b)为聚合物改性的多元醇,优选聚合物改性的聚酯醇或聚醚醇,特别优选的是接枝聚醚醇或接枝聚酯醇,特别地是接枝聚醚醇。这些为被称为聚合物多元醇的那些,其聚合物含量通常为5至60重量%,优选10至55重量%,特别优选30至55重量%,以及特别地为40至50重量%,该聚合物优选为热塑性聚合物。所述聚合物聚酯醇描述于例如WO 05/098763和EP-A-250 351中,并通常在作为接枝基础的聚酯醇中由合适的烯属单体的自由基聚合而获得,所述烯属单体如苯乙烯、丙烯腈、(甲基)丙烯酸酯、(甲基)丙烯酸和/或丙烯酰胺。侧链通常通过自由基从生长的聚合物链转移到聚酯醇或聚醚醇而形成。除接枝共聚物之外,聚合物多元醇主要包括分散在未改变的聚酯醇或聚醚醇中的烯烃的均聚物。
在一个优选的实施方案中,所用单体包括丙烯腈、苯乙烯、丙烯腈和苯乙烯,且特别优选仅使用苯乙烯。单体任选地在其他单体、大分子单体、慢化剂的存在下使用自由基引发剂(通常为偶氮化合物或过氧化合物)在作为连续相的聚酯醇或聚醚醇中而聚合。此方法描述于例如DE 111 394、US 3 304 273、US 3 383 351、US 3 523 093、DE 1 152 536和DE1 152 537中。
在自由基聚合反应中,大分子单体同时结合至共聚物链上。这得到这样的嵌段共聚物,其分别具有聚酯嵌段或聚醚嵌段,以及具有聚丙烯腈-苯乙烯嵌段,其中它们用作连续相和分散相的边界上的增容剂,并抑制聚合物聚酯醇颗粒附聚。大分子单体的比例通常为1至20重量%,基于制备聚合物多元醇所用的单体的总重量计。
如果相对高分子量的化合物b)包括聚合物多元醇,其优选与其它多元醇一起存在,例如与聚醚醇、聚酯醇或聚醚醇和聚酯醇的混合物。特别优选聚合物多元醇的比例为高于5重量%,基于组分b)的总重量计。例如聚合物多元醇的用量可为7至90重量%,或11至80重量%,基于组分b)的总重量计。特别优选聚合物多元醇包括聚合物聚酯醇或聚合物聚醚醇。
催化剂c)大大地加速了多元醇(b)和任选地增链剂和交联剂(d)以及化学发泡剂(e)与有机的任选地改性的多异氰酸酯(a)的反应。本文的催化剂(c)包括可结合的胺催化剂。这些催化剂具有至少一个、优选1至8、特别优选1至2个对异氰酸酯具有反应活性的基团,该基团优选为OH、NH或NH2基团。可结合的胺催化剂主要用于制备低排放的聚氨酯泡沫,其中它们特别用于汽车内饰领域。这些催化剂为已知的且描述于例如EP1888664中。这些材料包括除了具有对异氰酸酯有反应活性的基团外还优选具有一个或多个叔氨基的化合物。优选可结合催化剂的叔氨基带有至少两个脂肪族烃部分,优选每个部分具有1至10个碳原子,特别优选每个部分具有1至6个碳原子。特别优选的叔氨基带有两个相互独立地选自甲基和乙基的部分、以及还带有其它有机部分。可使用的可结合的催化剂的实例为双(二甲基氨基丙基)脲、双(N,N-二甲基氨基乙氧基乙基)氨基甲酸酯、二甲基氨基丙基脲,N,N,N-三甲基-N-羟乙基双(氨基丙基醚)、N,N,N-三甲基-N-羟乙基双(氨基乙基醚)、二乙基乙醇胺、双(N,N-二甲基-3-氨基丙基)胺、二甲基氨基丙基胺、3-二甲基氨基丙基-N,N-二甲基丙烷-1,3-二胺、二甲基-2-(2-氨基乙氧基乙醇)、以及(1,3-双(二甲基氨基)丙基-2-醇、N,N-双(3-二甲基氨基丙基)-N-异丙醇胺、双(二甲基氨基丙基)-2-羟基乙胺、N,N,N-三甲基-N-(3-氨基丙基)双(氨基乙基)醚、3-二甲基氨基异丙基二异丙醇胺,及其混合物。
除了可结合的胺催化剂,也可用常规催化剂制备聚氨酯。可提及的实例有脒,如2,3-二甲基-3,4,5,6-四氢嘧啶;叔胺,如三乙胺、三丁胺、二甲基苄胺、N-甲基吗啉、N-乙基吗啉、N-环己基吗啉、N,N,N′,N′-四甲基乙二胺、N,N,N′,N′-四甲基丁二胺、N,N,N′,N-四甲基己二胺、五甲基二亚乙基三胺、四甲基二氨基乙基醚、双(二甲基氨基丙基)脲、二甲基哌嗪、1,2-二甲基咪唑、1-氮杂双环[3,3,0]辛烷以及优选1,4-二氮杂双环[2,2,2]辛烷;和链烷醇胺化合物,如三乙醇胺、三异丙醇胺、N-甲基二乙醇胺、N-乙基二乙醇胺和二甲基乙醇胺。也可使用有机金属化合物,优选有机锡化合物如有机羧酸的锡(II)盐,如乙酸锡(II)、辛酸锡(II)、乙基己酸锡(II)和月桂酸锡(II);和有机羧酸的二烷基锡(IV)盐,如二乙酸二丁基锡、二月桂酸二丁基锡、马来酸二丁基锡和二乙酸二辛基锡;以及羧酸铋,如新癸酸铋(III)、2-乙基己酸铋和辛酸铋;或其混合物。有机金属化合物可单独使用或优选与强碱性胺结合使用。当组分(b)包括酯时,优选仅使用胺催化剂。在一个特别优选的实施方案中,所用的催化剂(c)仅包含可结合的催化剂。
组分(d)包含磷酸酯、多磷酸盐、膦酸酯,和/或亚磷酸酯。这些物质的摩尔质量优选至少为350g/mol。同样优选的还有磷酸酯、膦酸酯,和/或亚磷酸酯,其中这些物质具有至少一个对异氰酸酯有反应活性的基团,且该基团例如为OH。
本文所用的磷酸酯包括具有如下通式的磷酸的酯
(R1-O)3-P=O,
其中,三个R1部分相互独立地为包含一个或多个苯基、一个或多个磷酸基团或其酯和/或一个或多个选自氮、氧、氟、氯和溴的原子的有机部分。本文R1部分优选各自相互独立地包含1至20,特别优选2至10,且特别地2至5个碳原子,以及优选具有支链;所述部分优选是脂族的。优选该部分具有氯原子或氧原子,例如以OH端基的形式。R1部分的实例为氯乙烯、氯丙烯、氯丁烯、环氧乙烷、环氧丙烷、环氧丁烷以及优选具有2至10个重复单元的聚乙基环氧烷烃(polyethylalkylene oxide)。
本发明优选的磷酸酯在分子中包含至少两个,优选2至50个,特别优选2至20个磷酸酯基团,其中这些磷酸酯基团通过多官能部分键合,特别是通过二官能部分-R“-。本文R“为具有1至20个,优选2至10个,以及特别地2至5个碳原子的有机部分,其中这些部分可以为直链的或支链的,优选为支链的,且任选地包含一个或多个选自氮、氧、氟、氯和溴的原子。本发明的这些磷酸酯包括例如2,2-双(氯甲基)三亚甲基双(双(2-氯乙基)磷酸酯),三(2-丁氧基乙基)磷酸酯、三(1,3-二氯-2-异丙基)磷酸酯、三(2-氯异丙基)磷酸酯、以及具有环氧乙烷桥的低聚的烷基磷酸酯,例如购于ICL Industrial Products的PNX。
本发明的多磷酸盐为具有如下通式的化合物
–[P(O)(O-R‘+)-O]n-,
其中n为2至10000的整数,R‘+为碱金属阳离子或铵阳离子。任何所需的结构可用作端基,优选如下通式的结构
-O-P(O)(O-R‘+)2,
其中R‘+如上所定义。例如多磷酸铵可用作多磷酸盐。
本发明的膦酸酯为具有如下通式的化合物
(R3)(R2-O)2-P=O,
其中部分R2相互独立地为包含一个或多个选自氮、氧、氟、氯和溴的原子的有机部分,并优选具有支链;部分R3为氢或具有1至10个,优选1至5个,以及特别优选1至3个碳原子的芳族、脂族、或脂环族部分,其中这些部分还可任选地包含杂原子。
本文的部分R2优选各自相互独立地包含1至20个,特别优选2至10个,以及特别地2至5个碳原子。优选的部分包含氯原子或氧原子,例如以OH端基的形式。部分R2的实例为氯乙烯、氯丙烯、氯丁烯、环氧乙烷、环氧丙烷、环氧丁烷以及优选具有2至10个重复单元的聚乙基环氧烷烃。本发明的膦酸酯的实例为二(二乙二醇)甲基膦酸酯。
所用的亚磷酸酯包括如下通式的化合物,
(R4-O)3-P
其中部分R4相互独立地为包含一个或多个选自氮、氧、氟、氯和溴的原子的有机部分。优选的部分包含氯原子或氧原子,例如以OH端基的形式。本文部分R4优选各自相互独立地包含1至20个,特别优选2至10个,以及特别地2至5个碳原子。优选的部分包含氯原子或氧原子,例如以OH端基的形式。具体而言,亚磷酸酯包含OH端基。R4部分的实例为氯乙烯、氯丙烯、氯丁烯、环氧乙烷、环氧丙烷、环氧丁烷以及优选具有2至10个重复单元的聚乙基环氧烷烃。例如三(二丙二醇)亚磷酸酯用作亚磷酸酯。
特别优选的组分(d)为磷酸酯、膦酸酯、和/或亚磷酸酯,更优选地为分子中包含至少两个磷酸酯基团的化合物。实例为2,2-双(氯甲基)三亚甲基双(双(2-氯乙基)磷酸酯)、多磷酸铵、具有环氧乙烷桥的多烷基磷酸酯。优选的还有三(1,3-二氯-2-异丙基)磷酸酯、三(2-氯异丙基)磷酸酯、三(2-丁氧基乙基)磷酸酯、具有环氧乙烷桥的低聚烷基磷酸酯,以及二(二乙二醇)甲基磷酸酯。极特别优选的为2,2-双(氯甲基)三亚甲基双(双(2-氯乙基)磷酸酯)、二(二乙二醇)甲基磷酸酯、三(1,3-二氯-2-异丙基)磷酸酯、具有环氧乙烷桥的低聚烷基磷酸酯,以及多磷酸铵。特别地,优选2,2-双(氯甲基)三亚甲基双(双(2-氯乙基)磷酸酯)和具有环氧乙烷桥的低聚烷基磷酸酯。这些化合物为市售的。
本文组分(d)的比例,基于组分(a)至组分(f)的总重量计,为优选少于3重量%,特别优选0.05至2重量%。更优选0.1至1.5重量%,特别是0.15至1.0重量%,各自基于组分(a)至成分(f)的总重量计。甚至优选比例为0.1至0.4重量%、或特别优选比例为0.15至0.3重量%的组分(d),各自基于组分(a)至成分(f)的总重量计,对于改善热老化是足够的。特别优选的是本发明的聚氨酯包含少于5重量%的通常在聚氨酯泡沫中作为阻燃剂的其它物质,更优选少于2重量%,甚至更优选少于1重量%,且更特别地,不含所述其它物质。
在制备聚氨酯泡沫时还存在发泡剂(e)。所述发泡剂(e)包含水。可使用的发泡剂(e)不仅包含水,还包含已知的具有化学作用和/或物理作用的化合物。化学发泡剂是用以与异氰酸酯反应以形成气体产物的化合物,其实例为水或甲酸。物理发泡剂是在聚氨酯合成的起始材料中已经溶解或乳化且在聚氨酯形成条件下蒸发的化合物。实例为烃、卤代烃,以及其它化合物,如全氟烷烃(如全氟己烷)、氯氟烃;和醚、酯、酮、缩醛及其混合物,如具有4-8个碳原子的脂环族烃;或氟碳化合物,如购自Solvay Fluorides LLC的365mfc。在一个优选的实施方案中,使用的发泡剂为包含至少一种所述发泡剂和水的混合物,且特别地仅有水作为发泡剂。
在一个优选的实施方案中,水的含量为0.1至2重量%,优选0.2至1.5重量%,特别优选0.3至1.2重量%,特别地为0.4至1重量%,基于组分(a)至组分(g)的总重量计。
所用的增链剂和/或交联剂(f)包括摩尔质量优选少于500g/mol,特别优选60-400g/mol的物质,其中增链剂具有2个对异氰酸酯有反应活性的氢原子,交联剂具有3个对异氰酸酯有反应活性的氢原子。这些物质可单独使用或优选以混合物的形式使用。优选使用分子量少于400,特别优选60-300以及特别地为60-150的二元醇和/或三元醇。可使用的增链剂和交联剂的实例为具有2-14个碳原子且优选2-10个碳原子的脂族、脂环族和/或芳脂族(araliphatic)二元醇,如乙二醇、1,3-丙二醇、1,10-癸二醇、1,2-二羟基环己烷、1,3-二羟基环己烷、1,4-二羟基环己烷、二乙二醇、二丙二醇,以及优选1,4-丁二醇、1,6-己二醇和双(2-羟乙基)氢醌;三醇,如1,2,4-三羟基环己烷、1,3,5-三羟基环己烷、甘油和三羟甲基丙烷;和基于环氧乙烷和/或1,2-环氧丙烷及作为起始分子的上文提及的二醇和/或三醇的低分子量羟基化聚环氧烷烃。所用的增链剂(c)特别优选包括单乙二醇、1,4-丁二醇、甘油或其混合物,且特别地为单乙二醇或包含单乙二醇的混合物。
只要增链剂、交联剂或其混合物被使用,它们的用量有利地为1至60重量%,优选1.5至50重量%,特别地为2至40重量%,基于组分(b)和组分(c)的总量计。
助剂和/或添加剂(g)也可任选地加入至反应混合物中以制备聚氨酯泡沫。可提及的实例有表面活性剂、泡沫稳定剂、孔调节剂、脱模剂、橡胶硫化助剂、填料、染料、颜料、水解稳定剂、臭味吸收物质以及抑真菌剂和/或抑细菌剂。这些在制备聚氨酯泡沫中是已知的且经常使用。
本发明还提供一种制备本发明的聚氨酯泡沫的方法,通过混合组分(a)至(d)以及任选地组分(e)至(g)得到反应混合物,然后完成其反应以得到聚氨酯。所述材料优选彼此混合的量为使得多异氰酸酯(a)的NCO基团与组分(b)、(c)和(d)的反应性氢原子的总和的当量比为1:0.8-1:1.25,优选为1:0.9-1:1.15。
本发明优选的整体聚氨酯泡沫优选地借助在封闭的模具(有利地为温度控制模具)中低压或高压技术通过一步法制备。该模具通常由金属构成,例如铝或钢。这些步骤例如描述于Piechota和的"lntegralschaumstoff"[Integral foam],Carl-Hanser-Verlag,Munich,Vienna,1975,或描述于"Kunststoff-handbuch"[Plastics handbook],第7卷,Polyurethane[Polyurethanes],第3版,1993,第7章。
为此,起始组分优选在15至90℃,特别优选在25至55℃的温度下混合,且反应混合物任选地在升高的压力下引入封闭的模具中。该混合可通过搅拌器或螺杆混合器或在称为逆流注射方法(countercurrent injection process)中在高压下机械进行。模具温度有利地为20至160℃,优选30至120℃,特别优选为30至60℃。就本发明而言,本文所用的术语反应混合物为组分(a)至(g)在反应转化率小于90%时的混合物,基于异氰酸酯基团计。
引入模具的反应混合物的用量要使得得到的由整体泡沫制成的模塑物的密度优选为0.08至0.75g/cm3,特别优选为0.15至0.75g/cm3,且特别地为0.25至0.70g/cm3。用于制备本发明的整体聚氨酯泡沫的压实水平为1.1至8.5,优选2.1至7.0。
本发明的聚氨酯泡沫优选用于汽车内饰。本文包含的汽车内饰部件优选例如方向盘、仪表盘、门包层、头枕或操控按钮。此处本发明的聚氨酯泡沫展现了优异的抗老化性能,特别是在140℃7天的热老化性能,或在120℃和相对湿度为100%的高压釜中储存3个周期的(5小时一周期)湿热老化性能。本文中可以看到在最大拉伸应变中的抗张强度上的特别改进。
本文中热老化和湿热老化性能根据DIN EN ISO 2440进行测定。
以下实施例用以对本发明进行示例说明。
起始材料:
多元醇A:OH值为35mg KOH/g且官能度为2.7的聚醚醇,基于环氧乙烷和环氧丙烷,具有84%的环氧丙烷含量和14%的环氧乙烷含量
多元醇B:具有45%固体(苯乙烯-丙烯腈)含量的接枝多元醇在作为载体多元醇的多元醇A中
MEG:单乙二醇
Isopur SA-21050:购自ISL-Chemie的黑色糊料
Polycat 15:购自Air Products的催化剂
Jeffcat ZF-10:购自Huntsman的催化剂
磷化合物
P1:三(1,3-二氯-2-异丙基)磷酸酯
P2:具有环氧乙烷桥的低聚烷基磷酸酯
P3:二(二乙二醇)甲基膦酸酯
P5:异丙基化的三芳基磷酸酯
P6:三(二丙二醇)亚磷酸酯
P7:三(2-丁氧基乙基)磷酸酯
P8:三(2-氯异丙基)磷酸酯,TCPP
P9:磷酸三丁酯(对比)
P10:亚磷酸三丁酯(对比)
P11:三壬基苯基亚磷酸酯,TNPP(对比)
异氰酸酯:NCO含量为27.8的碳二亚胺改性的4,4’-MDI。
混合物A通过混合以下组分来制备:
0.25至2份的磷化合物(见表)
混合物A和异氰酸酯组分以异氰酸酯指数为102彼此混合并装入封闭的模具中,因此得到平均密度为380g/L的模塑物。用于确定测量力学性能值的方法按照以下标准进行。
性能 | 单位 | DIN标准 |
硬度 | Shore A | 53505 |
抗张强度 | MPa | 1798 |
拉伸应变 | % | 1798 |
密度 | g/mm<sup>3</sup> | 845 |
本文中热老化和湿热老化按照DIN EN ISO 2440进行测定。
表1:分别添加注明的浓度的、各自以重量份给出的磷化合物P1至P7(基于混合物A的总重量计)以及不添加磷化合物(对比)的最终整体泡沫在140℃老化7天前后的机械性能。
表2:分别添加注明的浓度的、各自以重量份给出的磷化合物P8至P12(基于混合物A的总重量计)的最终整体泡沫在140℃老化7天前后的机械性能。
表3:分别添加注明浓度的、各自以重量份给出的磷化合物P1至P4(基于混合物A的总重量计)以及不添加磷化合物(对比)的最终整体泡沫在高压釜中在120℃湿热老化3个周期(5个小时一周期)前后的机械性能。
表4:分别添加注明浓度的、各自以重量份给出的磷化合物P9至P12(基于混合物A的总重量计)的最终整体泡沫在高压釜中在120℃湿热老化3个周期(5个小时一周期)前后的机械性能。
以混合物A和异氰酸酯为原料,分别使用0.5重量份的磷化合物P1、P2和P3(基于混合物A的总重量计)以及不使用磷化合物(作为对比)制造方向盘,并将所述方向盘在140℃下老化7天。本文中不含磷化合物的方向盘中的聚氨酯易碎且部分断裂,而根据本发明制备的方向盘的聚氨酯在视觉上没有变化。
Claims (16)
1.一种聚氨酯泡沫,其通过混合以下组分得到反应混合物、并完成所述反应混合物的反应以得到聚氨酯泡沫而获得:
(a)多异氰酸酯,
(b)聚合物多元醇,其包含聚酯醇或聚醚醇,其中聚醚醇的官能度为2至3且分子量为1000至8000g/mol;聚酯醇的官能度为2至4且分子量为450至3000g/mol;
(c)包含可结合的胺催化剂的催化剂,所述可结合的胺催化剂选自N,N,N-三甲基-N-羟乙基双(氨基丙基醚)、双(N,N-二甲基-3-氨基丙基)胺、3-二甲基氨基丙基-N,N-二甲基丙烷-1,3-二胺、二甲基-2-(2-氨基乙氧基乙醇)、以及(1,3-双(二甲基氨基)丙基-2-醇、N,N-双(3-二甲基氨基丙基)-N-异丙醇胺、双(二甲基氨基丙基)-2-羟基乙胺、N,N,N-三甲基-N-(3-氨基丙基)双(氨基乙基)醚、3-二甲基氨基异丙基二异丙醇胺,及其混合物,
(d)磷酸酯、多磷酸盐和/或膦酸酯,
其中组分(d)的比例为0.05-2重量%,基于组分(a)至(f)的总重量计,
(e)含水的发泡剂,
(f)增链剂和/或交联剂,以及
(g)助剂和/或添加剂,
其中催化剂(c)仅为具有对异氰酸酯基具有反应活性的基团的催化剂,
其中磷酸酯具有的通式为
(R1-O)3-P=O,
其中三个R1部分相互独立地为包含一个或多个苯基、一个或多个磷酸基团或其酯,和/或一个或多个氧原子或氯原子的有机部分;或
其中磷酸酯在分子中包含至少两个磷酸酯基团,其中这些磷酸酯基团通过多官能部分键合,其中多官能部分为直链的或支链的,且包含一个或多个选自氮、氧、氟、氯和溴的原子;
多磷酸盐具有的通式为
–[P(O)(O-R‘+)-O]n-,
其中n为2至10000的整数,R‘+为碱金属阳离子或铵阳离子;
膦酸酯具有的通式为
(R3)(R2-O)2-P=O,
其中R2部分相互独立地为包含一个或多个选自氮、氧、氟、氯和溴的原子的有机部分,R3部分为氢或具有1至10个碳原子的芳族、脂族、或脂环族部分;
其中包含少于1重量%的除组分(d)之外的其它阻燃剂;
其中所述多异氰酸酯(a)的NCO基团与组分(b)、(c)和(d)的反应性氢原子的总和的当量比为1:0.8-1:1.25;且
其中所述聚氨酯泡沫为整体泡沫。
2.根据权利要求1的聚氨酯泡沫,其中所述磷酸基团为带有环氧乙烷的多烷基磷酸酯。
3.根据权利要求1的聚氨酯泡沫,其中所述磷酸酯和/或膦酸酯包含对异氰酸酯基有反应活性的基团。
4.根据权利要求1的聚氨酯泡沫,其中所述磷酸酯和/或膦酸酯包含OH基团。
5.根据权利要求1或3的聚氨酯泡沫,其中只用水作为发泡剂(e)。
6.根据权利要求1的聚氨酯泡沫,其中组分(d)包括分子中具有至少两个磷酸酯基团的化合物。
7.根据权利要求1的聚氨酯泡沫,其中所述聚氨酯泡沫为平均密度为100至850g/L的聚氨酯泡沫。
8.根据权利要求7的聚氨酯泡沫,其中所述聚氨酯泡沫为模塑的聚氨酯泡沫。
9.根据权利要求8的聚氨酯泡沫,其中所述模塑的聚氨酯泡沫的平均密度为150至500g/L。
10.根据权利要求1的聚氨酯泡沫,其中所述聚氨酯泡沫为汽车内饰部件。
11.根据权利要求10的聚氨酯泡沫,其中所述汽车内饰部件为方向盘、仪表盘、内部门包层、头枕或操控按钮。
12.根据权利要求1的聚氨酯泡沫,其不包含其它阻燃剂。
13.根据权利要求1的聚氨酯泡沫,其中聚酯醇的官能度为2至3且分子量为1000至3000g/mol。
14.一种制备聚氨酯泡沫的方法,通过混合以下组分得到反应混合物,并完成所述反应混合物的反应以得到聚氨酯泡沫:
(a)多异氰酸酯,
(b)聚合物多元醇,其包含聚酯醇或聚醚醇,其中聚醚醇的官能度为2至3且分子量为1000至8000g/mol;聚酯醇的官能度为2至4且分子量为450至3000g/mol;
(c)包含可结合的胺催化剂的催化剂,所述可结合的胺催化剂选自N,N,N-三甲基-N-羟乙基双(氨基丙基醚)、双(N,N-二甲基-3-氨基丙基)胺、3-二甲基氨基丙基-N,N-二甲基丙烷-1,3-二胺、二甲基-2-(2-氨基乙氧基乙醇)、以及(1,3-双(二甲基氨基)丙基-2-醇、N,N-双(3-二甲基氨基丙基)-N-异丙醇胺、双(二甲基氨基丙基)-2-羟基乙胺、N,N,N-三甲基-N-(3-氨基丙基)双(氨基乙基)醚、3-二甲基氨基异丙基二异丙醇胺,及其混合物,
(d)磷酸酯、多磷酸盐和/或膦酸酯,
其中组分(d)的比例为0.05-2重量%,基于组分(a)至(f)的总重量计,
(e)含水的发泡剂,
(f)增链剂和/或交联剂,以及
(g)助剂和/或添加剂
其中催化剂(c)仅为具有对异氰酸酯基具有反应活性的基团的催化剂,
其中磷酸酯具有的通式为
(R1-O)3-P=O,
其中三个R1部分相互独立地为包含一个或多个苯基、一个或多个磷酸基团或其酯,和/或一个或多个氧原子或氯原子的有机部分;或
其中磷酸酯在分子中包含至少两个磷酸酯基团,其中这些磷酸酯基团通过多官能部分键合,其中多官能部分为直链的或支链的,且包含一个或多个选自氮、氧、氟、氯和溴的原子;
多磷酸盐具有的通式为
–[P(O)(O-R‘+)-O]n-,
其中n为2至10000的整数,R‘+为碱金属阳离子或铵阳离子;
膦酸酯具有的通式为
(R3)(R2-O)2-P=O,
其中R2部分相互独立地为包含一个或多个选自氮、氧、氟、氯和溴的原子的有机部分,R3部分为氢或具有1至10个碳原子的芳族、脂族、或脂环族部分;
其中包含少于1重量%的除组分(d)之外的其它阻燃剂;
其中所述多异氰酸酯(a)的NCO基团与组分(b)、(c)和(d)的反应性氢原子的总和的当量比为1:0.8-1:1.25;且
其中所述聚氨酯泡沫为整体泡沫。
15.根据权利要求14的方法,其中所述磷酸基团为带有环氧乙烷的多烷基磷酸酯。
16.根据权利要求1至13中任一项的聚氨酯泡沫在汽车内饰中的用途。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP12178308.8 | 2012-07-27 | ||
EP12178308.8A EP2690118A1 (de) | 2012-07-27 | 2012-07-27 | Polyurethane enthaltend Phosphorverbindungen |
CN201380039946.2A CN104507991A (zh) | 2012-07-27 | 2013-07-16 | 含有磷化合物的聚氨酯泡沫 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201380039946.2A Division CN104507991A (zh) | 2012-07-27 | 2013-07-16 | 含有磷化合物的聚氨酯泡沫 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN109503809A CN109503809A (zh) | 2019-03-22 |
CN109503809B true CN109503809B (zh) | 2021-08-06 |
Family
ID=48793254
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201380039946.2A Pending CN104507991A (zh) | 2012-07-27 | 2013-07-16 | 含有磷化合物的聚氨酯泡沫 |
CN201811366606.1A Active CN109503809B (zh) | 2012-07-27 | 2013-07-16 | 含有磷化合物的聚氨酯泡沫 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201380039946.2A Pending CN104507991A (zh) | 2012-07-27 | 2013-07-16 | 含有磷化合物的聚氨酯泡沫 |
Country Status (5)
Country | Link |
---|---|
EP (2) | EP2690118A1 (zh) |
JP (2) | JP2015524499A (zh) |
KR (1) | KR102149805B1 (zh) |
CN (2) | CN104507991A (zh) |
WO (1) | WO2014016167A1 (zh) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2690118A1 (de) * | 2012-07-27 | 2014-01-29 | Basf Se | Polyurethane enthaltend Phosphorverbindungen |
CZ2015375A3 (cs) | 2015-06-03 | 2016-12-14 | Borcad Cz S.R.O. | Polyurethanová pěna se sníženou hořlavostí, sníženým vývojem kouře a nízkou toxicitou kouře |
EP3495404A1 (de) | 2017-12-07 | 2019-06-12 | Basf Se | Polyurethanschaum |
EP3560970A1 (de) * | 2018-04-25 | 2019-10-30 | Covestro Deutschland AG | Offenzelliger polyurethanhartschaum und dessen verwendung |
CN109369956B (zh) * | 2018-09-21 | 2020-07-31 | 浙江万盛股份有限公司 | 一种聚氨酯泡沫复合阻燃剂及其制备方法 |
Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2006698A1 (en) * | 1988-12-28 | 1990-06-28 | Manfred Genz | Process for the preparation of flame resistant, elastic polyurethane flexible foams while using at least one polyoxyalkylene polyamide and melamine |
CA2006697A1 (en) * | 1988-12-28 | 1990-06-28 | Heinz-Dieter Lutter | Process for the preparation of flame resistant, elastic polyurethane flexible foams and low viscosity melamine polyether polyol dispersions therefor |
US5124367A (en) * | 1990-07-03 | 1992-06-23 | Imperial Chemical Industries Plc | Fire retardant compositions comprising dispersion of fire retardant in isocyanate-reactive compound with fatty acid ester and/or amide as dispersing agent |
CA2216777A1 (en) * | 1996-10-18 | 1998-04-18 | Bernhard Naber | Production of tough polyurethane integral foams having improved tear propagation resistance, elongation at break and tensile strength |
EP0913415A1 (de) * | 1997-10-31 | 1999-05-06 | Südzucker Aktiengesellschaft Mannheim/Ochsenfurt | Polyurethane mit Kohlenhydratbausteinen |
EP1127908A1 (de) * | 2000-02-22 | 2001-08-29 | HILTI Aktiengesellschaft | Zweikomponenten-Ortschaumsystem und dessen Verwendung zum Ausschäumen von Öffnungen zum Zwecke des Brandschutzes |
CN1912001A (zh) * | 2005-08-11 | 2007-02-14 | 中国石油天然气集团公司 | 低腐蚀阻燃性聚氨酯组合料及制造方法 |
JP2008208264A (ja) * | 2007-02-27 | 2008-09-11 | Inoac Corp | 軟質ポリウレタン発泡体 |
JP2008266451A (ja) * | 2007-04-20 | 2008-11-06 | Inoac Corp | 軟質ポリウレタンフォーム |
CN101831168A (zh) * | 2010-05-14 | 2010-09-15 | 上海克络蒂材料科技发展有限公司 | 一种高阻燃的聚氨酯硬泡外墙保温材料及其制备方法 |
CN102060975A (zh) * | 2010-11-23 | 2011-05-18 | 无锡双象化学工业有限公司 | 室内门用硬泡聚氨酯组合料的制备方法 |
JP2015524499A (ja) * | 2012-07-27 | 2015-08-24 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | リン化合物を含むポリウレタンフォーム |
Family Cites Families (51)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL259615A (zh) | 1960-01-05 | |||
GB1022434A (en) | 1961-11-28 | 1966-03-16 | Union Carbide Corp | Improvements in and relating to polymers |
US3523093A (en) | 1961-11-28 | 1970-08-04 | Paul Stamberger | Method of producing polyurethanes by reacting polyisocyanate with a preformed polymer resulting from polymerization of ethylenically unsaturated monomers |
US3304273A (en) | 1963-02-06 | 1967-02-14 | Stamberger Paul | Method of preparing polyurethanes from liquid, stable, reactive, filmforming polymer/polyol mixtures formed by polymerizing an ethylenically unsaturated monomer in a polyol |
DE1152536B (de) | 1962-03-30 | 1963-08-08 | Bayer Ag | Verfahren zur Herstellung Urethangruppen enthaltender Schaumstoffe |
DE1152537B (de) | 1962-06-02 | 1963-08-08 | Bayer Ag | Verfahren zur Herstellung von homogenen, Urethangruppen aufweisenden Kunststoffen |
US3580869A (en) * | 1969-06-03 | 1971-05-25 | Davidson Rubber Co | Microcellular polyurethane foams based on aromatic polyamines and propoxylated aniline |
US3846348A (en) * | 1969-11-13 | 1974-11-05 | Cincinnati Milacron Inc | High impact, fire retardant, rigid polyurethane foam compositions having high resistance to boiling water and products therefrom |
US3849349A (en) * | 1971-05-12 | 1974-11-19 | K Frisch | Polyisocyanurate foam and process for producing the same |
BE786681A (fr) * | 1971-07-26 | 1973-01-25 | Stauffer Chemical Co | Polyphosphites de polyalkylene glycol-alkyle |
JPS515358A (zh) * | 1974-07-02 | 1976-01-17 | Mitsui Toatsu Chemicals | |
LU74540A1 (zh) * | 1976-03-12 | 1977-09-27 | ||
US4111828A (en) * | 1977-01-03 | 1978-09-05 | Monsanto Company | Storage stable polyol mixture |
DE2842582A1 (de) * | 1978-09-29 | 1980-08-21 | Bischofsheim Chemie Anlagen | Verfahren zur herstellung von geschaeumten oder nicht geschaeumten massen |
US4338408A (en) | 1981-07-20 | 1982-07-06 | Texaco Inc. | Polyurethanes using bis(aminoethyl)ether derivatives as catalysts |
US4895879A (en) * | 1984-08-17 | 1990-01-23 | The Dow Chemical Company | Internal mold release compositions |
DE3435070A1 (de) | 1984-09-25 | 1986-04-03 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von gegebenenfalls geschaeumten polyurethanen, die mit einem anderen werkstoff verbunden oder konfektioniert worden sind |
ES8800697A1 (es) | 1986-06-10 | 1987-12-01 | Hoocker Sa | Procedimiento para la obtencion de dispersiones de polimeros en poliesteres hidroxilados. |
JPH0288617A (ja) * | 1988-09-26 | 1990-03-28 | Toyota Motor Corp | 塩化ビニル表皮一体成形用ウレタン組成物 |
JPH0739456B2 (ja) * | 1991-07-03 | 1995-05-01 | 東ソー株式会社 | ポリウレタン製造用アミン触媒組成物及びポリウレタンの製造法 |
DE69122574T2 (de) * | 1990-07-30 | 1997-02-20 | Tosoh Corp | Aminkatalysator zur Herstellung von Polyurethanschäumen und Verfahren zur Herstellung dieser Schäume |
DE4030515A1 (de) * | 1990-09-27 | 1992-04-02 | Bayer Ag | Neue urethane, ein verfahren zu ihrer herstellung und ihre verwendung als katalysatoren fuer das isocyanat-polyadditionsverfahren |
US5175228A (en) * | 1991-12-09 | 1992-12-29 | Gencorp Inc. | Two-component primerless urethane-isocyanurate adhesive compositions having high temperature resistance |
US5324754A (en) * | 1992-12-14 | 1994-06-28 | Basf Corporation | Lithium-based salts in flexible foams |
EP0635527B1 (en) | 1993-07-22 | 1999-01-27 | Nisshinbo Industries, Inc. | Use of a halogen-free trialkyl phosphate in a process for producing polyisocyanurate foams |
JPH08217846A (ja) * | 1995-02-09 | 1996-08-27 | Bridgestone Corp | 低汚染性・難燃性ポリウレタンフォーム |
JPH10265540A (ja) * | 1997-03-26 | 1998-10-06 | Nippon Polyurethane Ind Co Ltd | 硬質ポリウレタンフォーム用組成物、及び該組成物を用いた硬質ポリウレタンフォームの製造方法 |
US5830926A (en) * | 1997-12-17 | 1998-11-03 | Basf Corporation | Flame retardant polyurethane foams |
JP3991422B2 (ja) * | 1998-03-02 | 2007-10-17 | 東ソー株式会社 | ポリオール組成物、難燃性ポリウレタン樹脂組成物及びそれらの製造法 |
JP2000159855A (ja) * | 1998-11-26 | 2000-06-13 | Mitsui Chemicals Inc | ポリウレタンフォームの製造方法 |
BR0208765A (pt) | 2001-04-01 | 2005-01-04 | Dow Global Technologies Inc | Espuma de poliuretano rìgidas |
ATE373691T1 (de) * | 2002-05-20 | 2007-10-15 | Great Lakes Chemical Corp | Mischungen von (alkylsubstituierten) triarylphosphatestern mit phosphor enthaltenden flammschutzmitteln für polyurethanschaumstoffe |
US20050009939A1 (en) | 2003-02-21 | 2005-01-13 | Woodbridge Foam Corporation | Isocyanate-based foam having improved anti-yellowing properties and process for production thereof |
US20060135634A1 (en) | 2003-03-11 | 2006-06-22 | Giuliano Guidetti | Low amine emission polyurethane foam |
WO2005098763A2 (de) | 2004-04-06 | 2005-10-20 | Giesecke & Devrient Gmbh | Vorrichtung und verfahren zur bearbeitung von banknoten |
JP4532161B2 (ja) * | 2004-04-27 | 2010-08-25 | 株式会社イノアックコーポレーション | ヘッドレスト用ポリウレタンフォーム及びヘッドレスト |
US20060258762A1 (en) * | 2005-05-13 | 2006-11-16 | Dobransky Michael A | Hydrocarbon or hydrofluorocarbon blown ASTM E-84 class I rigid polyurethane foams |
DE102005024144A1 (de) * | 2005-05-23 | 2006-11-30 | Basf Ag | Verfahren zur Herstellung von viskoelastischen Polyurethan-Weichschaumstoffen |
DE102005041763A1 (de) * | 2005-09-01 | 2007-03-08 | Basf Ag | Polyisocyanurat Hartschaum und Verfahren zur Herstellung |
DE102005041765A1 (de) * | 2005-09-01 | 2007-04-19 | Basf Ag | Polyurethan Hartschaum und Verfahren zur Herstellung |
ES2298026B1 (es) * | 2006-03-27 | 2009-08-17 | Synthesia Española S.A. | Nuevas composiciones de polioles y uso de las mismas. |
JP5014827B2 (ja) * | 2007-02-16 | 2012-08-29 | 株式会社イノアックコーポレーション | 軟質ポリウレタンフォーム |
US8535476B2 (en) * | 2007-08-01 | 2013-09-17 | Dow Global Technologies Llc | Heat bonding polyurethane foams |
WO2009065826A1 (de) | 2007-11-19 | 2009-05-28 | Basf Se | Verwendung von chlorierten kohlenwasserstoffen und chorierten alkylphosphaten bei der herstellung von polyurethanintegralschaumstoffen |
JP5232600B2 (ja) * | 2008-10-29 | 2013-07-10 | ベック株式会社 | ポリオール組成物 |
EP2403887A1 (en) * | 2009-03-05 | 2012-01-11 | Dow Global Technologies LLC (formerly Known As Dow Global Technologies Inc.) | Polyols from hppo and polyurethane products made therefrom |
ES2443834T3 (es) * | 2009-07-09 | 2014-02-20 | Bayer Intellectual Property Gmbh | Procedimiento para la fabricación de materiales de espuma de poliuretano ignífugos con buenas propiedades de uso a largo plazo |
DE102009029089A1 (de) | 2009-09-02 | 2011-03-03 | Evonik Goldschmidt Gmbh | Phosphorarme Laminieradditive mit geringer Emission, verbesserter Anfangshaftung und verbesserter Hydrolysestabilität |
CN102079804B (zh) * | 2009-11-27 | 2013-04-03 | 上海东大聚氨酯有限公司 | 制备聚氨酯硬质泡沫的组合聚醚及组合物,及其使用方法 |
EP2374843A1 (de) | 2010-04-07 | 2011-10-12 | Nexans | Alterungsbeständige Polyurethanmischung |
CN101851993B (zh) * | 2010-05-14 | 2012-05-23 | 上海克络蒂材料科技发展有限公司 | 一种防火阻燃的聚氨酯外墙保温系统材料 |
-
2012
- 2012-07-27 EP EP12178308.8A patent/EP2690118A1/de not_active Ceased
-
2013
- 2013-07-16 JP JP2015523493A patent/JP2015524499A/ja active Pending
- 2013-07-16 CN CN201380039946.2A patent/CN104507991A/zh active Pending
- 2013-07-16 EP EP13737252.0A patent/EP2877511B2/de active Active
- 2013-07-16 WO PCT/EP2013/064999 patent/WO2014016167A1/de active Application Filing
- 2013-07-16 KR KR1020157005374A patent/KR102149805B1/ko active IP Right Grant
- 2013-07-16 CN CN201811366606.1A patent/CN109503809B/zh active Active
-
2018
- 2018-03-02 JP JP2018037423A patent/JP6703025B2/ja active Active
Patent Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2006698A1 (en) * | 1988-12-28 | 1990-06-28 | Manfred Genz | Process for the preparation of flame resistant, elastic polyurethane flexible foams while using at least one polyoxyalkylene polyamide and melamine |
CA2006697A1 (en) * | 1988-12-28 | 1990-06-28 | Heinz-Dieter Lutter | Process for the preparation of flame resistant, elastic polyurethane flexible foams and low viscosity melamine polyether polyol dispersions therefor |
US5124367A (en) * | 1990-07-03 | 1992-06-23 | Imperial Chemical Industries Plc | Fire retardant compositions comprising dispersion of fire retardant in isocyanate-reactive compound with fatty acid ester and/or amide as dispersing agent |
CA2216777A1 (en) * | 1996-10-18 | 1998-04-18 | Bernhard Naber | Production of tough polyurethane integral foams having improved tear propagation resistance, elongation at break and tensile strength |
EP0913415A1 (de) * | 1997-10-31 | 1999-05-06 | Südzucker Aktiengesellschaft Mannheim/Ochsenfurt | Polyurethane mit Kohlenhydratbausteinen |
EP1127908A1 (de) * | 2000-02-22 | 2001-08-29 | HILTI Aktiengesellschaft | Zweikomponenten-Ortschaumsystem und dessen Verwendung zum Ausschäumen von Öffnungen zum Zwecke des Brandschutzes |
CN1912001A (zh) * | 2005-08-11 | 2007-02-14 | 中国石油天然气集团公司 | 低腐蚀阻燃性聚氨酯组合料及制造方法 |
JP2008208264A (ja) * | 2007-02-27 | 2008-09-11 | Inoac Corp | 軟質ポリウレタン発泡体 |
JP2008266451A (ja) * | 2007-04-20 | 2008-11-06 | Inoac Corp | 軟質ポリウレタンフォーム |
CN101831168A (zh) * | 2010-05-14 | 2010-09-15 | 上海克络蒂材料科技发展有限公司 | 一种高阻燃的聚氨酯硬泡外墙保温材料及其制备方法 |
CN102060975A (zh) * | 2010-11-23 | 2011-05-18 | 无锡双象化学工业有限公司 | 室内门用硬泡聚氨酯组合料的制备方法 |
JP2015524499A (ja) * | 2012-07-27 | 2015-08-24 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | リン化合物を含むポリウレタンフォーム |
Also Published As
Publication number | Publication date |
---|---|
JP2015524499A (ja) | 2015-08-24 |
JP2018111826A (ja) | 2018-07-19 |
KR102149805B1 (ko) | 2020-08-31 |
CN109503809A (zh) | 2019-03-22 |
CN104507991A (zh) | 2015-04-08 |
EP2877511A1 (de) | 2015-06-03 |
KR20150040996A (ko) | 2015-04-15 |
JP6703025B2 (ja) | 2020-06-03 |
EP2877511B1 (de) | 2016-09-14 |
EP2877511B2 (de) | 2024-03-27 |
WO2014016167A1 (de) | 2014-01-30 |
EP2690118A1 (de) | 2014-01-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6703025B2 (ja) | リン化合物を含むポリウレタンフォーム | |
US6331577B1 (en) | Process for producing elastic polyurethane moldings with compact surfaces and cellular cores | |
CN106459366B (zh) | 基于聚氨酯的密实弹性体模制部件 | |
EP3063201B1 (en) | Low density polyurethane microcellular elastomer | |
US10266635B2 (en) | Polyurethane foams comprising phosphorus compounds | |
CN106459367B (zh) | 具有降低的醛排放的聚氨酯 | |
JP2015507513A (ja) | 高反発弾性・低圧縮永久ひずみの低密度ポリウレタン製の靴底または靴底部材 | |
KR101554757B1 (ko) | 내부 이형제로서 디알킬 시클로헥산디카르복실레이트를 포함하는 인테그랄 폴리우레탄 폼 | |
KR20160027080A (ko) | 가수분해 저항성 폴리우레탄 몰딩 | |
CN114127147B (zh) | 聚氨酯组合物、用所述聚氨酯组合物制备的产品和所述产品的制备方法 | |
US9713884B2 (en) | Dimensionally stable polyurethane molded bodies having low density | |
US20140073712A1 (en) | Polyurethanes comprising halogen compounds | |
CN107428908B (zh) | 具有优异的低温挠性的聚氨酯模制体 | |
CN106029730B (zh) | 由聚酯聚氨酯组成的耐水解聚氨酯模制品 | |
KR20200145584A (ko) | 고탄성연질폴리우레탄폼개발 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |