CA1092591A - Phenol-aldehyde-amine resin/glycol curatives for energy absorbing polyurethanes - Google Patents
Phenol-aldehyde-amine resin/glycol curatives for energy absorbing polyurethanesInfo
- Publication number
- CA1092591A CA1092591A CA289,518A CA289518A CA1092591A CA 1092591 A CA1092591 A CA 1092591A CA 289518 A CA289518 A CA 289518A CA 1092591 A CA1092591 A CA 1092591A
- Authority
- CA
- Canada
- Prior art keywords
- weight
- parts
- aromatic
- diol
- mixture
- 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims description 9
- 239000004814 polyurethane Substances 0.000 title claims description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims description 3
- 229920005989 resin Polymers 0.000 title abstract description 19
- 239000011347 resin Substances 0.000 title abstract description 19
- 229920002635 polyurethane Polymers 0.000 title description 3
- 229920001971 elastomer Polymers 0.000 claims abstract description 27
- 239000000806 elastomer Substances 0.000 claims abstract description 23
- 150000002009 diols Chemical class 0.000 claims abstract description 16
- 230000001413 cellular effect Effects 0.000 claims abstract description 8
- 229920005862 polyol Polymers 0.000 claims description 65
- 150000003077 polyols Chemical class 0.000 claims description 62
- 239000000203 mixture Substances 0.000 claims description 61
- -1 alkylene diol Chemical class 0.000 claims description 45
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 42
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 40
- 230000008569 process Effects 0.000 claims description 35
- 239000011541 reaction mixture Substances 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 22
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 21
- 239000007795 chemical reaction product Substances 0.000 claims description 20
- 239000005056 polyisocyanate Substances 0.000 claims description 16
- 229920001228 polyisocyanate Polymers 0.000 claims description 15
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 13
- 150000004982 aromatic amines Chemical class 0.000 claims description 11
- 239000004604 Blowing Agent Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 229920006311 Urethane elastomer Polymers 0.000 claims description 5
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 5
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 210000003850 cellular structure Anatomy 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 229920003225 polyurethane elastomer Polymers 0.000 abstract description 4
- 229920000642 polymer Polymers 0.000 description 36
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 33
- 150000001875 compounds Chemical class 0.000 description 28
- 238000009472 formulation Methods 0.000 description 28
- 239000012948 isocyanate Substances 0.000 description 25
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 23
- 150000002513 isocyanates Chemical class 0.000 description 23
- 239000003981 vehicle Substances 0.000 description 19
- 239000000463 material Substances 0.000 description 17
- 239000000306 component Substances 0.000 description 15
- 150000003673 urethanes Chemical class 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 150000001299 aldehydes Chemical class 0.000 description 12
- 239000012190 activator Substances 0.000 description 11
- 125000002947 alkylene group Chemical group 0.000 description 11
- 238000007906 compression Methods 0.000 description 11
- 230000006835 compression Effects 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 229940126062 Compound A Drugs 0.000 description 10
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 150000002989 phenols Chemical class 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- 150000004984 aromatic diamines Chemical class 0.000 description 8
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- 229920001400 block copolymer Polymers 0.000 description 7
- 239000006260 foam Substances 0.000 description 7
- 230000009257 reactivity Effects 0.000 description 7
- 230000035945 sensitivity Effects 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 238000009863 impact test Methods 0.000 description 6
- 238000012545 processing Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000004364 calculation method Methods 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- 239000012973 diazabicyclooctane Substances 0.000 description 5
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 4
- 101150064205 ESR1 gene Proteins 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 150000001448 anilines Chemical class 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 235000013824 polyphenols Nutrition 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 229940095050 propylene Drugs 0.000 description 4
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 4
- 239000005060 rubber Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- IQVNEKKDSLOHHK-FNCQTZNRSA-N (E,E)-hydramethylnon Chemical compound N1CC(C)(C)CNC1=NN=C(/C=C/C=1C=CC(=CC=1)C(F)(F)F)\C=C\C1=CC=C(C(F)(F)F)C=C1 IQVNEKKDSLOHHK-FNCQTZNRSA-N 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical class NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 3
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 230000003116 impacting effect Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- RNVCVTLRINQCPJ-UHFFFAOYSA-N ortho-methyl aniline Natural products CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 3
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 3
- DQLGIONSPPKALA-UHFFFAOYSA-N phenylazanium;phenoxide Chemical compound NC1=CC=CC=C1.OC1=CC=CC=C1 DQLGIONSPPKALA-UHFFFAOYSA-N 0.000 description 3
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- HRXZRAXKKNUKRF-UHFFFAOYSA-N 4-ethylaniline Chemical compound CCC1=CC=C(N)C=C1 HRXZRAXKKNUKRF-UHFFFAOYSA-N 0.000 description 2
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
- 101150034533 ATIC gene Proteins 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 239000013536 elastomeric material Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-methyl-PhOH Natural products CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 2
- HMNKTRSOROOSPP-UHFFFAOYSA-N meta-ethylphenol Natural products CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N meta-toluidine Natural products CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-methyl phenol Natural products CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 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 2
- 229940029284 trichlorofluoromethane Drugs 0.000 description 2
- 150000004072 triols Chemical class 0.000 description 2
- DGLFZUBOMRZNQX-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluorocyclobutane Chemical compound FC1(F)CC(F)(F)C1(F)F DGLFZUBOMRZNQX-UHFFFAOYSA-N 0.000 description 1
- WGZYQOSEVSXDNI-UHFFFAOYSA-N 1,1,2-trifluoroethane Chemical compound FCC(F)F WGZYQOSEVSXDNI-UHFFFAOYSA-N 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- RFCAUADVODFSLZ-UHFFFAOYSA-N 1-Chloro-1,1,2,2,2-pentafluoroethane Chemical compound FC(F)(F)C(F)(F)Cl RFCAUADVODFSLZ-UHFFFAOYSA-N 0.000 description 1
- VGVRPFIJEJYOFN-UHFFFAOYSA-N 2,3,4,6-tetrachlorophenol Chemical class OC1=C(Cl)C=C(Cl)C(Cl)=C1Cl VGVRPFIJEJYOFN-UHFFFAOYSA-N 0.000 description 1
- UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical class OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 description 1
- RLEWTHFVGOXXTN-UHFFFAOYSA-N 2,3-diethylphenol Chemical class CCC1=CC=CC(O)=C1CC RLEWTHFVGOXXTN-UHFFFAOYSA-N 0.000 description 1
- VVAKEQGKZNKUSU-UHFFFAOYSA-N 2,3-dimethylaniline Chemical group CC1=CC=CC(N)=C1C VVAKEQGKZNKUSU-UHFFFAOYSA-N 0.000 description 1
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 1
- HRQPPTDGMMGDKC-UHFFFAOYSA-N 2,3-dipropylphenol Chemical class CCCC1=CC=CC(O)=C1CCC HRQPPTDGMMGDKC-UHFFFAOYSA-N 0.000 description 1
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 1
- MYEWQUYMRFSJHT-UHFFFAOYSA-N 2-(2-aminophenyl)sulfonylaniline Chemical class NC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1N MYEWQUYMRFSJHT-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical compound CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical class OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
- HDVUPIFFKAHPJY-UHFFFAOYSA-N 2-butylaniline Chemical compound CCCCC1=CC=CC=C1N HDVUPIFFKAHPJY-UHFFFAOYSA-N 0.000 description 1
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical class CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- FDIPWBUDOCPIMH-UHFFFAOYSA-N 2-decylphenol Chemical class CCCCCCCCCCC1=CC=CC=C1O FDIPWBUDOCPIMH-UHFFFAOYSA-N 0.000 description 1
- MOEFFSWKSMRFRQ-UHFFFAOYSA-N 2-ethoxyphenol Chemical compound CCOC1=CC=CC=C1O MOEFFSWKSMRFRQ-UHFFFAOYSA-N 0.000 description 1
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 1
- FIWYWGLEPWBBQU-UHFFFAOYSA-N 2-heptylphenol Chemical class CCCCCCCC1=CC=CC=C1O FIWYWGLEPWBBQU-UHFFFAOYSA-N 0.000 description 1
- ABMULKFGWTYIIK-UHFFFAOYSA-N 2-hexylphenol Chemical class CCCCCCC1=CC=CC=C1O ABMULKFGWTYIIK-UHFFFAOYSA-N 0.000 description 1
- WCRKLZYTQVZTMM-UHFFFAOYSA-N 2-octadecylphenol Chemical class CCCCCCCCCCCCCCCCCCC1=CC=CC=C1O WCRKLZYTQVZTMM-UHFFFAOYSA-N 0.000 description 1
- MEEKGULDSDXFCN-UHFFFAOYSA-N 2-pentylphenol Chemical class CCCCCC1=CC=CC=C1O MEEKGULDSDXFCN-UHFFFAOYSA-N 0.000 description 1
- WMIQWIJPGVVMII-UHFFFAOYSA-N 3-butylaniline Chemical compound CCCCC1=CC=CC(N)=C1 WMIQWIJPGVVMII-UHFFFAOYSA-N 0.000 description 1
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- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 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
- 125000005628 tolylene group Chemical group 0.000 description 1
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- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
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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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/6505—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen the low-molecular compounds being 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
- 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
- C08G18/544—Polycondensates of aldehydes with nitrogen compounds
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)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US743,613 | 1976-11-22 | ||
| US05/743,613 US4107106A (en) | 1976-11-22 | 1976-11-22 | Phenol-aldehyde-amine resin/glycol curatives for energy absorbing polyurethanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1092591A true CA1092591A (en) | 1980-12-30 |
Family
ID=24989458
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA289,518A Expired CA1092591A (en) | 1976-11-22 | 1977-10-26 | Phenol-aldehyde-amine resin/glycol curatives for energy absorbing polyurethanes |
Country Status (17)
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH624011A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1977-08-05 | 1981-07-15 | Battelle Memorial Institute | |
| DE2964476D1 (en) * | 1978-07-05 | 1983-02-17 | Dow Chemical Co | Process for the preparation of a polyurethane from an organic polyisocyanate or polyisothiocyanate and three different active hydrogen atom containing compounds |
| US4246363A (en) * | 1979-06-18 | 1981-01-20 | The Dow Chemical Company | Reaction injection molded polyurethanes having particular flexural modulus factors and at least two thermal transition temperatures in a particular range |
| US4247655A (en) * | 1979-09-18 | 1981-01-27 | Union Carbide Corporation | Rigid and semiflexible polyurethane foams produced with phenol-aldehyde-amine resins |
| US4269945A (en) * | 1980-01-24 | 1981-05-26 | The Dow Chemical Company | Reaction injection molded polyurethanes employing aliphatic amine chain extenders |
| JPS5844693B2 (ja) * | 1980-03-25 | 1983-10-05 | 旭硝子株式会社 | ポリオ−ルの製造方法 |
| US4281089A (en) * | 1980-09-08 | 1981-07-28 | E. I. Du Pont De Nemours And Company | Polyurethane compositions and process |
| US4495081A (en) * | 1982-07-13 | 1985-01-22 | The Dow Chemical Company | Compositions containing polyether polyols and aliphatic primary amines |
| US4530941A (en) * | 1983-01-26 | 1985-07-23 | The Dow Chemical Company | Reaction injection molded polyurethanes employing high molecular weight polyols |
| US4642320A (en) * | 1983-11-02 | 1987-02-10 | The Dow Chemical Company | Reaction injection molded polyureas employing high molecular weight amine-terminated polyethers |
| US5198475A (en) * | 1990-10-31 | 1993-03-30 | Mitsui Toatsu Chemicals, Inc. | Polyol and utilization thereof |
| 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 |
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| EP0921961B1 (en) | 1996-08-30 | 2001-07-04 | Woodbridge Foam Corporation | Seat, and process, mold and system for production thereof |
| US5882073A (en) * | 1996-08-30 | 1999-03-16 | Woodbridge Foam Corporation | Foam passenger seat having trim cover attachment means |
| US5827547A (en) * | 1996-08-30 | 1998-10-27 | Woodbridge Foam Corporation | Mold for production of a passenger seat |
| US5762842A (en) * | 1996-08-30 | 1998-06-09 | Burchi; Charles R. | Process for seat production |
| US5827546A (en) * | 1996-08-30 | 1998-10-27 | Woodbridge Foam Corporation | System for production of a passenger seat |
| WO2000071382A1 (en) | 1999-05-19 | 2000-11-30 | Woodbridge Foam Corporation | Trim cover attachment system |
| DE10226062A1 (de) * | 2002-06-12 | 2004-01-08 | Ab Elektronik Gmbh | Weitwinkel-Drehwinkelsensor |
| US20090088535A1 (en) * | 2006-02-28 | 2009-04-02 | Dic Corporation | Method of producing phenol resin and method of producing epoxy resin |
| US20100320780A1 (en) * | 2009-06-18 | 2010-12-23 | B Green Innovations, Inc. | Composite vehicle bumper using recycled rubber |
| US9156124B2 (en) * | 2010-07-08 | 2015-10-13 | Nexplanar Corporation | Soft polishing pad for polishing a semiconductor substrate |
| EP3686181B1 (en) | 2013-01-30 | 2024-07-17 | Ecolab USA Inc. | Hydrogen sulfide scavengers |
| WO2016172275A1 (en) | 2015-04-22 | 2016-10-27 | Ecolab Usa Inc. | Development of a novel high temperature stable scavenger for removal of hydrogen sulfide |
| WO2017044248A1 (en) | 2015-09-08 | 2017-03-16 | Ecolab Usa Inc. | Hydrogen sulfide scavengers |
| CN107949625B (zh) | 2015-09-08 | 2020-10-02 | 艺康美国股份有限公司 | 作为硫化氢清除剂的烃溶性/分散性半缩甲醛 |
| WO2018022841A1 (en) | 2016-07-29 | 2018-02-01 | Ecolab Usa Inc. | Antifouling and hydrogen sulfide scavenging compositions |
| WO2019014415A1 (en) | 2017-07-13 | 2019-01-17 | Ecolab USA, Inc. | METHOD FOR REMOVING A COMPOUND CONTAINING SULFUR BY ADDITION OF A COMPOSITION |
| WO2020065561A1 (en) | 2018-09-25 | 2020-04-02 | Proprietect L.P. | Composite foam article |
| WO2020154251A1 (en) | 2019-01-23 | 2020-07-30 | Ecolab Usa Inc. | Complete removal of solids during hydrogen sulfide scavenging operations using a scavenger and a michael acceptor |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3186969A (en) * | 1961-10-09 | 1965-06-01 | Union Carbide Corp | Vicinal epoxide adducts of phenol-aromatic amine-formaldhyde condensation products |
| NL130122C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1962-05-01 | |||
| GB1131885A (en) * | 1966-08-29 | 1968-10-30 | Takeda Chemical Industries Ltd | A process for the production of polyurethane elastomer |
| US3493257A (en) * | 1967-03-22 | 1970-02-03 | Gen Motors Corp | Resilient microcellular foam bumper |
| US3558529A (en) * | 1967-05-03 | 1971-01-26 | Union Carbide Corp | Urethane polymers having improved stiffness-temperature properties |
| US3514144A (en) * | 1967-11-01 | 1970-05-26 | Sterling Alderfer Co | Elastomeric energy dissipating bumper |
| US3823176A (en) * | 1968-05-13 | 1974-07-09 | Basf Wyandotte Corp | Ester-containing amine-based liquid polyols and use in preparation of urethane compositions |
| US3586649A (en) * | 1968-12-12 | 1971-06-22 | Gen Tire & Rubber Co | Polyurethane foam structures with integral skin of improved properties and method of making |
| US3580869A (en) * | 1969-06-03 | 1971-05-25 | Davidson Rubber Co | Microcellular polyurethane foams based on aromatic polyamines and propoxylated aniline |
| US3939106A (en) * | 1973-03-20 | 1976-02-17 | Union Carbide Corporation | Energy absorbing polyurethane-polyurea cellular elastomers |
-
1976
- 1976-11-22 US US05/743,613 patent/US4107106A/en not_active Expired - Lifetime
-
1977
- 1977-10-26 CA CA289,518A patent/CA1092591A/en not_active Expired
- 1977-11-18 AU AU30751/77A patent/AU517340B2/en not_active Expired
- 1977-11-21 AR AR270038A patent/AR221690A1/es active
- 1977-11-21 IT IT29862/77A patent/IT1088893B/it active
- 1977-11-21 MX MX171402A patent/MX147521A/es unknown
- 1977-11-21 JP JP13901677A patent/JPS5364300A/ja active Granted
- 1977-11-21 BR BR7707707A patent/BR7707707A/pt unknown
- 1977-11-21 BE BE182775A patent/BE861011A/xx not_active IP Right Cessation
- 1977-11-21 NL NL7712789A patent/NL7712789A/xx not_active Application Discontinuation
- 1977-11-21 SE SE7713133A patent/SE441007B/sv not_active IP Right Cessation
- 1977-11-21 DE DE2751923A patent/DE2751923C2/de not_active Expired
- 1977-11-21 FR FR7734908A patent/FR2371471A1/fr active Granted
- 1977-11-21 ES ES464327A patent/ES464327A1/es not_active Expired
- 1977-11-21 GB GB48396/77A patent/GB1559245A/en not_active Expired
-
1981
- 1981-06-25 HK HK277/81A patent/HK27781A/xx not_active IP Right Cessation
-
1982
- 1982-12-30 MY MY42/82A patent/MY8200042A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HK27781A (en) | 1981-07-03 |
| BR7707707A (pt) | 1978-07-11 |
| JPS5740852B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-08-31 |
| FR2371471A1 (fr) | 1978-06-16 |
| FR2371471B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-03-05 |
| AU517340B2 (en) | 1981-07-23 |
| SE441007B (sv) | 1985-09-02 |
| BE861011A (fr) | 1978-05-22 |
| AU3075177A (en) | 1979-05-24 |
| IT1088893B (it) | 1985-06-10 |
| MX147521A (es) | 1982-12-13 |
| SE7713133L (sv) | 1978-07-06 |
| US4107106A (en) | 1978-08-15 |
| DE2751923C2 (de) | 1983-10-27 |
| NL7712789A (nl) | 1978-05-24 |
| DE2751923A1 (de) | 1978-05-24 |
| ES464327A1 (es) | 1978-09-01 |
| GB1559245A (en) | 1980-01-16 |
| MY8200042A (en) | 1982-12-31 |
| JPS5364300A (en) | 1978-06-08 |
| AR221690A1 (es) | 1981-03-13 |
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