DE1569497C3 - Verfahren zur Herstellung von Polyurethanschaumstoffen - Google Patents
Verfahren zur Herstellung von PolyurethanschaumstoffenInfo
- Publication number
- DE1569497C3 DE1569497C3 DE1569497A DE1569497A DE1569497C3 DE 1569497 C3 DE1569497 C3 DE 1569497C3 DE 1569497 A DE1569497 A DE 1569497A DE 1569497 A DE1569497 A DE 1569497A DE 1569497 C3 DE1569497 C3 DE 1569497C3
- Authority
- DE
- Germany
- Prior art keywords
- polyamines
- polyol
- mixture
- weight
- production
- 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 20
- 238000004519 manufacturing process Methods 0.000 title claims description 16
- 229920005830 Polyurethane Foam Polymers 0.000 title claims description 15
- 239000011496 polyurethane foam Substances 0.000 title claims description 15
- 229920005862 polyol Polymers 0.000 claims description 43
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 42
- 150000003077 polyols Chemical class 0.000 claims description 41
- 229920000768 polyamine Polymers 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 36
- 239000006260 foam Substances 0.000 claims description 33
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 18
- 150000001412 amines Chemical class 0.000 claims description 16
- 229920005903 polyol mixture Polymers 0.000 claims description 16
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 15
- 239000005056 polyisocyanate Substances 0.000 claims description 15
- 229920001228 polyisocyanate Polymers 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000004814 polyurethane Substances 0.000 claims description 8
- 229920002635 polyurethane Polymers 0.000 claims description 8
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- -1 hydroxyl compound Chemical class 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 239000003380 propellant Substances 0.000 claims description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 150000004982 aromatic amines Chemical class 0.000 claims description 3
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 claims description 3
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 2
- 230000002349 favourable effect Effects 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 229920000570 polyether Polymers 0.000 claims 2
- YCWRFIYBUQBHJI-UHFFFAOYSA-N 2-(4-aminophenyl)acetonitrile Chemical group NC1=CC=C(CC#N)C=C1 YCWRFIYBUQBHJI-UHFFFAOYSA-N 0.000 claims 1
- OHKOAJUTRVTYSW-UHFFFAOYSA-N 2-[(2-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC=C1CC1=CC=CC=C1N OHKOAJUTRVTYSW-UHFFFAOYSA-N 0.000 claims 1
- 239000004604 Blowing Agent Substances 0.000 claims 1
- 239000002131 composite material Substances 0.000 claims 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 239000013638 trimer Substances 0.000 claims 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 17
- GQWWGRUJOCIUKI-UHFFFAOYSA-N 2-[3-(2-methyl-1-oxopyrrolo[1,2-a]pyrazin-3-yl)propyl]guanidine Chemical compound O=C1N(C)C(CCCN=C(N)N)=CN2C=CC=C21 GQWWGRUJOCIUKI-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 230000032683 aging Effects 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 235000011187 glycerol Nutrition 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 239000011574 phosphorus Substances 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- WBJBEMDHFMUSAY-UHFFFAOYSA-N dibutyl phosphono phosphate Chemical compound CCCCOP(=O)(OP(O)(O)=O)OCCCC WBJBEMDHFMUSAY-UHFFFAOYSA-N 0.000 description 3
- 235000019256 formaldehyde Nutrition 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 2
- XOUAQPDUNFWPEM-UHFFFAOYSA-N 2,3,4-tris(hydroxymethyl)phenol Chemical compound OCC1=CC=C(O)C(CO)=C1CO XOUAQPDUNFWPEM-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical compound OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 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
- 239000001294 propane Substances 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 230000008961 swelling Effects 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
- 239000000080 wetting agent Substances 0.000 description 2
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 1
- SQHKJSPPFSVNDF-UHFFFAOYSA-N 1,2,2,3-tetrakis(hydroxymethyl)cyclohexan-1-ol Chemical compound OCC1CCCC(O)(CO)C1(CO)CO SQHKJSPPFSVNDF-UHFFFAOYSA-N 0.000 description 1
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-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
- 101150040471 19 gene Proteins 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 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 1
- HEBKCHPVOIAQTA-QWWZWVQMSA-N D-arabinitol Chemical compound OC[C@@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-QWWZWVQMSA-N 0.000 description 1
- 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 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229930195725 Mannitol Natural products 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 101150109831 SIN4 gene Proteins 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229940091181 aconitic acid Drugs 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 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
- YMLHHVGZNCZRQP-UHFFFAOYSA-N aniline;2-methyloxirane Chemical compound CC1CO1.NC1=CC=CC=C1 YMLHHVGZNCZRQP-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910002114 biscuit porcelain Inorganic materials 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000009970 fire resistant effect Effects 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- AAYGSSGHJGVNSK-UHFFFAOYSA-N hexane-1,3,6-triol Chemical compound OCCCC(O)CCO AAYGSSGHJGVNSK-UHFFFAOYSA-N 0.000 description 1
- 150000004000 hexols Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 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
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- OHQOKJPHNPUMLN-UHFFFAOYSA-N n,n'-diphenylmethanediamine Chemical class C=1C=CC=CC=1NCNC1=CC=CC=C1 OHQOKJPHNPUMLN-UHFFFAOYSA-N 0.000 description 1
- SHDJPKGVCIPPSC-UHFFFAOYSA-N octane-1,4,6-triol Chemical compound CCC(O)CC(O)CCCO SHDJPKGVCIPPSC-UHFFFAOYSA-N 0.000 description 1
- XCWZSWBOSVVZGV-UHFFFAOYSA-N oxolane-2,5-diol Chemical compound OC1CCC(O)O1 XCWZSWBOSVVZGV-UHFFFAOYSA-N 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N para-methylaniline Natural products CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols 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
- C08G18/40—High-molecular-weight compounds
- C08G18/54—Polycondensates of aldehydes
- C08G18/546—Oxyalkylated polycondensates of aldehydes
-
- 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
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
- C08G18/5033—Polyethers having heteroatoms other than oxygen having nitrogen containing carbocyclic 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
- C08G18/65—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
-
- 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
- C08G2110/0016—Foam properties semi-rigid
-
- 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
- C08G2110/0025—Foam properties rigid
-
- 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
- C08G2110/005—< 50kg/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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyethers (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33460063A | 1963-12-30 | 1963-12-30 | |
| US49063265A | 1965-09-27 | 1965-09-27 | |
| US55856166A | 1966-06-20 | 1966-06-20 | |
| US66061467A | 1967-08-15 | 1967-08-15 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1569497A1 DE1569497A1 (de) | 1970-04-09 |
| DE1569497B2 DE1569497B2 (de) | 1973-07-05 |
| DE1569497C3 true DE1569497C3 (de) | 1974-02-07 |
Family
ID=27502499
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1569497A Expired DE1569497C3 (de) | 1963-12-30 | 1964-12-14 | Verfahren zur Herstellung von Polyurethanschaumstoffen |
| DE19661645594 Pending DE1645594A1 (de) | 1963-12-30 | 1966-09-27 | Verfahren zur Herstellung von starren Polyurethanschaumstoffen |
| DE19671719274 Pending DE1719274B2 (de) | 1963-12-30 | 1967-06-20 | Verfahren zur herstellung eines polyurethanschaumstoffes |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661645594 Pending DE1645594A1 (de) | 1963-12-30 | 1966-09-27 | Verfahren zur Herstellung von starren Polyurethanschaumstoffen |
| DE19671719274 Pending DE1719274B2 (de) | 1963-12-30 | 1967-06-20 | Verfahren zur herstellung eines polyurethanschaumstoffes |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US3499009A (en, 2012) |
| JP (2) | JPS4928038B1 (en, 2012) |
| BE (1) | BE657763A (en, 2012) |
| CH (1) | CH484218A (en, 2012) |
| DE (3) | DE1569497C3 (en, 2012) |
| GB (3) | GB1042220A (en, 2012) |
| NL (2) | NL6414735A (en, 2012) |
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3676497A (en) * | 1968-08-06 | 1972-07-11 | Upjohn Co | Process for preparing di(aminophenyl)-methanes |
| US3876570A (en) * | 1971-02-24 | 1975-04-08 | Upjohn Co | Polyurethane foams based on certain alkoxylated cyanoethylated aryl amines |
| US3836424A (en) * | 1972-07-18 | 1974-09-17 | R Grieve | Polyisocyanurate foam articles |
| US3939106A (en) * | 1973-03-20 | 1976-02-17 | Union Carbide Corporation | Energy absorbing polyurethane-polyurea cellular elastomers |
| US4001329A (en) * | 1974-02-25 | 1977-01-04 | Owens-Corning Fiberglas Corporation | Aniline based reaction product |
| US4060439A (en) * | 1974-05-22 | 1977-11-29 | Union Carbide Corporation | Polyurethane foam composition and method of making same |
| US3948825A (en) * | 1974-07-05 | 1976-04-06 | Basf Wyandotte Corporation | Curing agent for use in making cellular polyurethane compositions |
| JPS5212238B2 (en, 2012) * | 1974-10-07 | 1977-04-05 | ||
| US4209609A (en) * | 1977-11-07 | 1980-06-24 | Mobay Chemical Corporation | Toluene diamine initiated polyether polyols |
| US4221877A (en) * | 1978-01-27 | 1980-09-09 | Texaco Development Corp. | Modified diphenylmethane diisocyanates useful in polyurethanes or polyisocyanurates |
| US4243759A (en) * | 1979-12-12 | 1981-01-06 | Mobay Chemical Corporation | Toluene diamine initiated polyether polyols |
| US4562290A (en) * | 1981-12-01 | 1985-12-31 | Basf Wyandotte Corporation | Alkylene oxide adducts of vicinal toluenediamine |
| US4421871A (en) * | 1981-12-01 | 1983-12-20 | Basf Wyandotte Corporation | Propylene oxide adducts of toluenediamine |
| US4391728A (en) * | 1981-12-01 | 1983-07-05 | Basf Wyandotte Corporation | Propylene oxide adducts of toluenediamine |
| DE3208693A1 (de) * | 1982-03-11 | 1983-09-22 | Hoechst Ag, 6230 Frankfurt | Polyol-vormischung zur herstellung von flammwidrigen polyurethanschaumstoffen |
| DE3217816A1 (de) * | 1982-05-12 | 1983-11-17 | Hoechst Ag, 6230 Frankfurt | Teilchenfoermiges mittel zur verminderung der entzuendlichkeit von brennbaren stoffen |
| US4499264A (en) * | 1983-06-27 | 1985-02-12 | Texaco Inc. | Preparation of amino polyols |
| US4469822A (en) * | 1983-07-14 | 1984-09-04 | Basf Wyandotte Corporation | Alkylene oxide adducts of vicinal toluenediamine and co-initiators, useful for rigid polyurethane foams |
| US4569952A (en) * | 1984-05-03 | 1986-02-11 | Mobay Chemical Corporation | Flexible polyurethane foams having improved load bearing characteristics and mixtures useful therein |
| US4542049A (en) * | 1984-08-28 | 1985-09-17 | Ashland Oil, Inc. | Flexibilized polyurethane pipe coating |
| US4664563A (en) * | 1984-09-21 | 1987-05-12 | Basf Corporation | Rigid polyurethane foams with constant or slightly decreasing strain with an increasing stress in compression |
| US4614754A (en) * | 1984-09-21 | 1986-09-30 | Basf Corporation | Rigid polyurethane foams with constant or slightly decreasing strain with an increasing stress in compression |
| US4596685A (en) * | 1984-10-18 | 1986-06-24 | Basf Corporation | Oxyethylated aromatic amines and their use as chain extenders in the preparation of polyurethane-polyurea elastomers |
| US4585807A (en) * | 1985-01-14 | 1986-04-29 | Basf Corporation | Rigid polyurethane foams employing oxyalkylated ethylenediamine |
| US4743628A (en) * | 1986-08-06 | 1988-05-10 | Air Products And Chemicals, Inc. | Polyurethane foams incorporating alkoxylated aromatic diamine and acetylenic glycol |
| US4992484A (en) * | 1987-11-20 | 1991-02-12 | Air Products And Chemicals, Inc. | Polyurethane systems incorporating alkoxylated diethyltoluenediamine |
| DE3829290A1 (de) * | 1988-08-30 | 1990-03-15 | Bayer Ag | Polyetherpolyole auf basis aromatischer di- und/oder polyamine, verfahren zu ihrer herstellung und verwendung fuer polyurethan- und polyisocyanurat-kunststoffe |
| US5397810A (en) * | 1989-07-19 | 1995-03-14 | Mitsui Toatsu Chemicals, Inc. | Polyol, polyurethane resin and utilization thereof |
| JPH0393826A (ja) * | 1989-09-06 | 1991-04-18 | Mitsui Toatsu Chem Inc | 硬質ウレタンフォームの製造法 |
| DE69023138T2 (de) * | 1990-11-02 | 1996-04-04 | Mitsui Toatsu Chemicals | Polyol und seine Verwendung. |
| JP3176058B2 (ja) * | 1990-11-05 | 2001-06-11 | 三井化学株式会社 | ポリオール及びその用途 |
| DE19630787A1 (de) * | 1996-07-31 | 1998-02-05 | Basf Ag | Verfahren zur Herstellung von Polyurethanen mit verbesserter Aushärtung |
| US5872292A (en) * | 1997-01-24 | 1999-02-16 | Bayer Corporation | Stable aromatic amine composition, a process for preparing color stable aromatic amines, and the production of light colored aromatic amine-based polyether polyols |
| US6004482A (en) * | 1997-12-24 | 1999-12-21 | Bayer Corporation | Stable aromatic amine composition, and a process for preparing color stable aromatic amines |
| US6031137A (en) | 1998-05-29 | 2000-02-29 | Bayer Corporation | Stable aromatic amine composition, a process for preparing color stable aromatic amines, and the production of light colored aromatic amine-based polyether polyols |
| DE19916945C1 (de) * | 1999-04-15 | 2000-10-05 | Clariant Gmbh | Aromatische Aldehydharze und ihre Verwendung als Emulsionsspalter |
| DE19916946C1 (de) | 1999-04-15 | 2000-07-27 | Clariant Gmbh | Aromatische Aldehydharze und ihre Verwendung als Emulsionsspalter |
| US6762214B1 (en) * | 2003-03-18 | 2004-07-13 | Bayer Polymers Llc | Process for the production of rigid foams from alkaline polyether polyols |
| US8933188B2 (en) * | 2004-11-12 | 2015-01-13 | Henkel US IP LLC | Low misting laminating adhesives |
| US20060229409A1 (en) * | 2005-04-08 | 2006-10-12 | Ilmenev Pavel E | Method for preparing polyurethane dispersions |
| JP2009057482A (ja) * | 2007-08-31 | 2009-03-19 | Sumika Bayer Urethane Kk | 硬質ポリウレタンフォームの製造方法 |
| EP3284494A1 (en) * | 2009-07-30 | 2018-02-21 | Tandem Diabetes Care, Inc. | Portable infusion pump system |
| US20120232180A1 (en) * | 2011-03-08 | 2012-09-13 | Basf Se | Process for the production of polyurethane rigid foams |
| JP6155201B2 (ja) * | 2011-03-08 | 2017-06-28 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | ポリウレタン硬質発泡体の製造方法 |
| US10818450B2 (en) | 2017-06-14 | 2020-10-27 | Black & Decker Inc. | Paddle switch |
| JP7433314B2 (ja) * | 2018-12-13 | 2024-02-19 | ダウ グローバル テクノロジーズ エルエルシー | 液体洗濯洗剤配合物 |
| EP3894537B1 (en) * | 2018-12-13 | 2022-10-19 | Dow Global Technologies LLC | Cleaning booster |
| CN113980264B (zh) * | 2021-11-30 | 2023-02-28 | 江苏钟山新材料有限公司 | 一种阻燃聚醚多元醇的制备方法及其应用 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR79511E (en, 2012) * | 1963-03-29 | |||
| US2683730A (en) * | 1951-01-17 | 1954-07-13 | Goodyear Tire & Rubber | Polyisocyanates and mixtures thereof |
| IT570070A (en, 2012) * | 1956-04-13 | |||
| NL280259A (en, 2012) * | 1957-05-10 | |||
| IT699971A (en, 2012) * | 1958-08-15 | |||
| US3152188A (en) * | 1960-11-15 | 1964-10-06 | Nalco Chemical Co | Nu-substituted polyalkylene polyamines having 2-hydroxyethyl and mono-secondary-hydroxyl hydrocarbon substituents |
| US3159591A (en) * | 1961-06-28 | 1964-12-01 | Union Carbide Corp | Flame-resistant urethane foams |
| US3175007A (en) * | 1961-08-14 | 1965-03-23 | Dow Chemical Co | Purification of dianilines |
| US3186969A (en) * | 1961-10-09 | 1965-06-01 | Union Carbide Corp | Vicinal epoxide adducts of phenol-aromatic amine-formaldhyde condensation products |
| NL130122C (en, 2012) * | 1962-05-01 |
-
0
- NL NL133349D patent/NL133349C/xx active
-
1964
- 1964-11-25 GB GB47990/64A patent/GB1042220A/en not_active Expired
- 1964-12-14 DE DE1569497A patent/DE1569497C3/de not_active Expired
- 1964-12-17 NL NL6414735A patent/NL6414735A/xx unknown
- 1964-12-21 JP JP39071761A patent/JPS4928038B1/ja active Pending
- 1964-12-23 CH CH1657364A patent/CH484218A/de not_active IP Right Cessation
- 1964-12-30 BE BE657763A patent/BE657763A/xx unknown
-
1965
- 1965-09-27 US US490632A patent/US3499009A/en not_active Expired - Lifetime
-
1966
- 1966-09-03 JP JP41057922A patent/JPS5116480B1/ja active Pending
- 1966-09-07 GB GB40032/66A patent/GB1119390A/en not_active Expired
- 1966-09-27 DE DE19661645594 patent/DE1645594A1/de active Pending
-
1967
- 1967-05-16 GB GB22705/67A patent/GB1147106A/en not_active Expired
- 1967-06-20 DE DE19671719274 patent/DE1719274B2/de active Pending
- 1967-08-15 US US660614A patent/US3423344A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE1719274A1 (de) | 1970-12-03 |
| BE657763A (en, 2012) | 1965-06-30 |
| GB1119390A (en) | 1968-07-10 |
| JPS5116480B1 (en, 2012) | 1976-05-24 |
| JPS4928038B1 (en, 2012) | 1974-07-23 |
| DE1569497B2 (de) | 1973-07-05 |
| DE1569497A1 (de) | 1970-04-09 |
| CH484218A (de) | 1970-01-15 |
| NL6414735A (en, 2012) | 1965-07-01 |
| DE1719274B2 (de) | 1972-08-17 |
| GB1147106A (en) | 1969-04-02 |
| US3423344A (en) | 1969-01-21 |
| NL133349C (en, 2012) | |
| DE1645594A1 (de) | 1970-07-09 |
| GB1042220A (en) | 1966-09-14 |
| US3499009A (en) | 1970-03-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |