EP3684760A2 - Novel compositions and methods to produce alkoxylated triazine-arylhydroxy-aldehyde condensates - Google Patents
Novel compositions and methods to produce alkoxylated triazine-arylhydroxy-aldehyde condensatesInfo
- Publication number
- EP3684760A2 EP3684760A2 EP18857763.9A EP18857763A EP3684760A2 EP 3684760 A2 EP3684760 A2 EP 3684760A2 EP 18857763 A EP18857763 A EP 18857763A EP 3684760 A2 EP3684760 A2 EP 3684760A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- formula
- group
- arylhydroxy
- triazine
- compound
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims description 70
- 238000000034 method Methods 0.000 title claims description 17
- -1 alkylene carbonate Chemical compound 0.000 claims abstract description 38
- 150000001875 compounds Chemical class 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 239000004814 polyurethane Substances 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 229920002635 polyurethane Polymers 0.000 claims description 20
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical group OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 239000000178 monomer Substances 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 12
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 12
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 6
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 238000004132 cross linking Methods 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 239000006254 rheological additive Substances 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 description 39
- 239000006260 foam Substances 0.000 description 34
- 150000003077 polyols Chemical class 0.000 description 27
- 238000009472 formulation Methods 0.000 description 26
- 239000012948 isocyanate Substances 0.000 description 21
- 150000002513 isocyanates Chemical class 0.000 description 20
- 238000012360 testing method Methods 0.000 description 17
- 229920000642 polymer Polymers 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000005056 polyisocyanate Substances 0.000 description 14
- 229920001228 polyisocyanate Polymers 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- 239000003063 flame retardant Substances 0.000 description 12
- 229920005830 Polyurethane Foam Polymers 0.000 description 11
- 239000011496 polyurethane foam Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 150000001299 aldehydes Chemical class 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 8
- 229920003986 novolac Polymers 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 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 7
- 229960003742 phenol Drugs 0.000 description 7
- 230000014759 maintenance of location Effects 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 239000011495 polyisocyanurate Substances 0.000 description 5
- 229920000582 polyisocyanurate Polymers 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 5
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 5
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 4
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 235000011181 potassium carbonates Nutrition 0.000 description 4
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000009413 insulation Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229960004889 salicylic acid Drugs 0.000 description 3
- 230000000391 smoking effect Effects 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 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 3
- 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 3
- OWICEWMBIBPFAH-UHFFFAOYSA-N (3-diphenoxyphosphoryloxyphenyl) diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=C(OP(=O)(OC=2C=CC=CC=2)OC=2C=CC=CC=2)C=CC=1)(=O)OC1=CC=CC=C1 OWICEWMBIBPFAH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 239000002981 blocking agent Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 230000001143 conditioned effect Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 229940015043 glyoxal Drugs 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- XMNDMAQKWSQVOV-UHFFFAOYSA-N (2-methylphenyl) diphenyl phosphate Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 XMNDMAQKWSQVOV-UHFFFAOYSA-N 0.000 description 1
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 1
- OTJFQRMIRKXXRS-UHFFFAOYSA-N (hydroxymethylamino)methanol Chemical compound OCNCO OTJFQRMIRKXXRS-UHFFFAOYSA-N 0.000 description 1
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- DTZHXCBUWSTOPO-UHFFFAOYSA-N 1-isocyanato-4-[(4-isocyanato-3-methylphenyl)methyl]-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(CC=2C=C(C)C(N=C=O)=CC=2)=C1 DTZHXCBUWSTOPO-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- VZDIRINETBAVAV-UHFFFAOYSA-N 2,4-diisocyanato-1-methylcyclohexane Chemical compound CC1CCC(N=C=O)CC1N=C=O VZDIRINETBAVAV-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- BNCADMBVWNPPIZ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COCN(COC)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 BNCADMBVWNPPIZ-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-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
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- NAMCDLUESQLMOZ-UHFFFAOYSA-N 6-ethyl-1,3,5-triazine-2,4-diamine Chemical compound CCC1=NC(N)=NC(N)=N1 NAMCDLUESQLMOZ-UHFFFAOYSA-N 0.000 description 1
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
- NGYGUYRBWLUDRP-UHFFFAOYSA-N 6-propyl-1,3,5-triazine-2,4-diamine Chemical compound CCCC1=NC(N)=NC(N)=N1 NGYGUYRBWLUDRP-UHFFFAOYSA-N 0.000 description 1
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 1
- VIZORQUEIQEFRT-UHFFFAOYSA-N Diethyl adipate Chemical compound CCOC(=O)CCCCC(=O)OCC VIZORQUEIQEFRT-UHFFFAOYSA-N 0.000 description 1
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 1
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 1
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
- IXQBIOPGDNZYNA-UHFFFAOYSA-N N=C=O.N=C=O.CC1=CC=CC=C1C1=CC=CC=C1C Chemical compound N=C=O.N=C=O.CC1=CC=CC=C1C1=CC=CC=C1C IXQBIOPGDNZYNA-UHFFFAOYSA-N 0.000 description 1
- SPTUBPSDCZNVSI-UHFFFAOYSA-N N=C=O.N=C=O.COC1=CC=CC=C1C1=CC=CC=C1OC Chemical compound N=C=O.N=C=O.COC1=CC=CC=C1C1=CC=CC=C1OC SPTUBPSDCZNVSI-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- YGCOKJWKWLYHTG-UHFFFAOYSA-N [[4,6-bis[bis(hydroxymethyl)amino]-1,3,5-triazin-2-yl]-(hydroxymethyl)amino]methanol Chemical compound OCN(CO)C1=NC(N(CO)CO)=NC(N(CO)CO)=N1 YGCOKJWKWLYHTG-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- NJYZCEFQAIUHSD-UHFFFAOYSA-N acetoguanamine Chemical compound CC1=NC(N)=NC(N)=N1 NJYZCEFQAIUHSD-UHFFFAOYSA-N 0.000 description 1
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- UFWLHIVKHDCSHZ-UHFFFAOYSA-N chembl1595789 Chemical compound NC1=NC(N)=NC(C=2C(=CC=CC=2)O)=N1 UFWLHIVKHDCSHZ-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229940117916 cinnamic aldehyde Drugs 0.000 description 1
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- KTLIMPGQZDZPSB-UHFFFAOYSA-M diethylphosphinate Chemical compound CCP([O-])(=O)CC KTLIMPGQZDZPSB-UHFFFAOYSA-M 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 229940043276 diisopropanolamine Drugs 0.000 description 1
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-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
- 150000002009 diols Chemical class 0.000 description 1
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000007706 flame test Methods 0.000 description 1
- 229920005570 flexible polymer Polymers 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910001386 lithium phosphate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical compound NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 1
- 229940087646 methanolamine Drugs 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 description 1
- 229960003868 paraldehyde Drugs 0.000 description 1
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005903 polyol mixture Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000004588 polyurethane sealant Substances 0.000 description 1
- ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- ZSKGQVFRTSEPJT-UHFFFAOYSA-N pyrrole-2-carboxaldehyde Chemical compound O=CC1=CC=CN1 ZSKGQVFRTSEPJT-UHFFFAOYSA-N 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical compound N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 description 1
- TWQULNDIKKJZPH-UHFFFAOYSA-K trilithium;phosphate Chemical compound [Li+].[Li+].[Li+].[O-]P([O-])([O-])=O TWQULNDIKKJZPH-UHFFFAOYSA-K 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003739 xylenols 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/64—Condensation products of melamine with aldehydes; Derivatives thereof
-
- 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
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3842—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring
- C08G18/3851—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring containing three nitrogen atoms in the ring
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
- C08G73/0644—Poly(1,3,5)triazines
-
- 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
Definitions
- This invention relates to alkoxylated triazine-arylhydroxy-aldehyde condensate compositions and methods for making these compositions.
- Aromatic polyols are used as cross-linkers for isocyanates and isocyanurates that go into polyurethane and polyisocyanurate-based polymers.
- the largest end use for aromatic polyols is in applications where insulation, flammability, and structural performance are most important.
- halogenated flame retardants are inexpensive, they have been linked to environmental concerns. Accordingly, there remains an opportunity to develop rigid polyurethane foam that has a minimum amount of halogenated flame retardants or eliminate the need to have an additional flame retardant that resists scorching, burning, and smoking, while simultaneously having acceptable physical properties.
- Novolacs are known to the polyurethane industry as aromatic polyols that typically go into rigid polyurethane and polyisocyanurate foam applications.
- the novolac polyol is said to promote intumescence (i.e., swelling) of the rigid polyurethane foam, promotes char, decreases scorch, and decreases flammability of the foam.
- the novolac polyol is also thought to react with isocyanates more quickly than the isocyanates react with water thereby increasing production speed, reducing cost, and allowing the rigid polyurethane foam prepared from a novolac polyol to be used in a wide variety of applications, especially those that require fast foaming times.
- the gel time is typically 10- 25 seconds so the novolac has to mix into the system quickly, which can be a challenge due to the inherent viscosity.
- the urethane bond formed by the reaction of aromatic polyol and isocyanate is reversible at certain temperatures where the aliphatic polyol replaces the aromatic polyol.
- the current polyurethane formulations for applications such as rigid foam require multifunctional polyols as isocyanate reactive chemicals.
- the common ones are carbohydrate-based polyols, which are not very effective when it comes to flame resistance.
- an alkoxylated triazine-arylhydroxy-aldehyde condensate compound is prepared by a process comprising, consisting of, or consisting essentially of: reacting a) a triazine-arylhydroxy-aldehyde condensate; and b) at least one alkylene carbonate optionally in the presence of a catalyst, to form an alkoxylated triazine-arylhydroxy-aldehyde condensate compound.
- Embodiments of the invention are directed to alkoxylated triazine- arylhydroxy-aldehyde condensates, methods for making the alkoxylated triazine- arylhydroxy-aldehyde condensates, and the use of alkoxylated triazine-arylhydroxy- aldehyde condensates in the manufacture of polyurethane and polyisocyanurate resins.
- An alkoxylated triazine-arylhydroxy-aldehyde condensate is formed by reacting a triazine-arylhydroxy-aldehyde condensate with an alkylene carbonate.
- any suitable triazine-arylhydroxy-aldehyde condensate can be used in the reaction with the alkylene carbonate.
- the triazine-arylhydroxy- aldehyde condensate is formed from a reaction mixture of a triazine monomer, an arylhydroxy monomer, and an aldehyde monomer.
- the triazine- arylhydroxy-aldehyde condensate is a novolac.
- the triazine monomer can be a triazine compound or a triazine derivative.
- An example of a triazine compound is melamine and an example of a triazine derivative is a melamine derivative.
- Suitable compounds that can be used as the triazine monomer include compounds selected from the group of aminotriazine, 4-methyl-l,3,5-triazine-2-amine, 2- amino-4,6-dimethyl-l ,3,5-triazine, melamine, hexamethoxymethylmelamine, hexamethylolmelamine, guanamine, acetoguanamine, propioguanamine, butyroguanamine, benzoguanamine, vinylguanamine, 6-(hydroxyphenyl)-2,4-diamino- 1,3, 5 -triazine, and combinations thereof.
- the arylhydroxy monomer can be any suitable aromatic monomer with one or more hydroxyl groups per molecule, such as a monohydroxy, dihydroxy or a trihydroxy benzene. They can be mononuclear or binuclear.
- the arylhydroxy monomer is a phenol monomer compound. Phenol monomer compounds having at least one ortho or para position available for bonding are preferred compounds.
- the phenol monomer compound can be an unsubstituted or substituted compound, for example, with an alkyl group, a phenyl group, a hydroxybenzene group, an alkoxy group, and combinations and subsets thereof.
- the phenol monomer compound can also include compounds having up to about 15 carbon atoms such as up to about 8 carbon atoms.
- arylhydroxy monomers include, but are not limited to phenol, cresols, xylenols, resorcinol, catechol, hydroquinone, naphthols, biphenols, bisphenols, phloroglucinol, pyrogallol or their derivatvies.
- the aldehyde monomer includes compounds having one or more aldehyde functional groups (-CHO) and any compounds yielding aldehydes.
- the aldehyde monomer can be represented by the formula R-CHO, and R can be an aliphatic or aromatic organic functional group.
- the aldehyde monomer can be a dialdehyde such as glyoxal.
- Suitable aldehydes include, but are not limited to compounds selected from the group of formaldehyde, paraformaldehyde, acetaldehyde, i-butyraldehyde (isobutyraldehyde), benzaldehyde, acrolein, crotonaldehyde, salicylaldehyde, 4-hydroxybenzaldehyde, furaldehyde, pyrrolaldehyde, cinnamaldehyde, trioxymethylene, paraldehyde, terephthaldialdehyde, glyoxal, glutaraldehyde and combinations thereof.
- the triazine-arylhydroxy-aldehyde condensate can be comprised of a variety of triazine, arylhydroxy, and aldehyde combinations.
- the condensate is a melamine, phenol, and formaldehyde novolac. Further details about the triazine-arylhydroxy-aldehyde condensate and its preparation can be found in US Patent Nos. 6,239,248 and 9,249,251, which are both herein incorporated by reference.
- the triazine-arylhydroxy-aldehyde condensate is reacted with at least one alkylene carbonate to form the alkoxylated triazine-arylhydroxy-aldehyde condensate.
- the alkylene carbonate can be a variety of alkylene carbonates. Mixtures of alkylene carbonates can also be used.
- the general structure of an alkylene carbonate is represented by Formula I, below:
- Ri and R 2 are each independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a vinyl group, or an alkyl group with 1 to 4 carbon atoms containing a hydroxyl group.
- the alkylene carbonate can also be a six-membered structure, as represented by Formula II, below:
- R 3 , R 4 , and R 5 are each independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a vinyl group, or an alkyl group with 1 to 4 carbon atoms containing a hydroxyl group.
- Ri and R 2 in the product structure generally correspond to the Ri and R 2 groups of Formula I.
- R 3 , Rt, and/or R 5 groups are substituted for the Ri and R 2 groups.
- the alkylene carbonate can be selected from the group consisting of ethylene carbonate, propylene carbonate, and mixtures thereof.
- reaction conditions can include a reaction temperature in the range of from 50°C to 270°C. Any and all temperatures within the range of 50°C to 270°C are incorporated herein and disclosed herein; for example, the reaction temperature can be from 100°C to 200°C, from 140°C to 180°C, or from 160°C to 175°C.
- the reaction conditions can also include a reaction pressure in the range of from 0.01 bar to 100 bar.
- reaction pressure can be from 0.1 bar to 50 bar, from 0.5 bar to 20 bar, or from 1 bar to 10 bar.
- the components can be added together in any suitable manner.
- the reaction can take place in a batch system, a continuous system, a semi- batch system, or a semi-continuous system.
- the alkylene carbonate can be added slowly to molten triazine-arylhydroxy-aldehyde condensate and then reacted until C0 2 evolution has ceased.
- the reaction between the triazine-arylhydroxy-aldehyde condensate and the alkylene carbonate can take place in the presence of a catalyst.
- catalysts include, but are not limited to sodium hydroxide, potassium hydroxide, lithium hydroxide, ammonium hydroxide, magnesium hydroxide, calcium hydroxide, barium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, potassium phosphate, sodium phosphate, and lithium phosphate.
- an organic acid such as oxalic acid, formic acid, acetic acid, trifluoroacetic acid, methane sulfonic acid, salicylic acid, or p-toluenesulfonic acid can be used to neutralize the reaction mixture.
- the alkoxylated triazine-arylhydroxy-aldehyde condensate compound can be represented by Formula III below.
- R 6 functional group is represented by Formula IV or Formula V.
- the R 7 functional group of Formula III can be a hydrogen atom or represented by Formula IV or Formula VI.
- R 8 and R9 can each independently be a hydrogen atom, an alkyl group with
- Ri and R 2 are independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a vinyl group, or an alkyl group with 1 to 4 carbon atoms containing a hydroxyl group.
- Rio can be a hydrogen atom, an alkyl group with 1 to 10 carbon atoms, an alkyl group with 1 to 10 carbon atoms containing a hydroxyl group, a phenyl group, a vinyl group, a propenyl group, a hydroxyl-containing phenyl group, a pyrrole group, or a furanyl group.
- Rn and R12 are each independently a hydrogen atom, an alkyl group with 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a phenyl group, a hydoxybenzene group, or an alkyl group with 1 to 10 carbon atoms with at least one carbon substituted with i) a hydroxyl group, ii) a hydroxybenzene group or iii) a phenyl group.
- Rn and R12 can jointly form a common aromatic ring with or without a hydroxyl group.
- R 13 and R14 are each independently a hydrogen atom, an alkyl group with 1 to 10 carbon atoms, a vinyl group, a phenyl group, a hydroxyphenyl group, -NH(Formula VI), -N(Formula VI) 2 , -NH(Formula VI), -N((Formula IV)(Formula VI)), -N(Formula VI) 2 , [0036] Ri 5 , R 16 , and R17 are each independently a hydrogen atom, an alkyl group with 1 to 10 carbon atoms, a vinyl group, a phenyl group, a hydroxyphenyl group, - NH(FormulaVI), -N(Formula VI) 2 , -NH(Formula VII), -N(Formula VI)(Formula VII), - N(Formula VII) 2 , or -NH 2 .
- each m is independently from 1 to 10
- each n is independently from 0 to 10
- each x is independently from 1 to 2
- each x' is independently from 0 to 2.
- Monomers depicted by m and n can be arranged in any order, combination, or sub-combination.
- the alkoxylated triazine-arylhydroxy-aldehyde condensates generally have a nitrogen content of from 0.5 weight percent to 40 weight percent, and from 5 weight percent to 15 weight percent in various other embodiments.
- alkoxylated triazine-arylhydroxy-aldehyde condensate is represented by Formula VIII, below:
- Formula XI Another example of the alkoxylated triazine-arylhydroxy-aldehyde condensate is represented by Formula XI, below:
- Formula XIV Another example of the alkoxylated triazine-arylhydroxy-aldehyde condensate is represented by Formula XV, below:
- the alkoxylated triazine-arylhydroxy-aldehyde condensates of this invention generally have a viscosity in a solvent in the range of from about 1 Pascal second to 1,700 Pascal seconds at 25°C. Any and all ranges within 1 to 1,700 Pascal seconds are included herein and disclosed herein, for example, the alkoxylated triazine-arylhydroxy-aldehyde condensates in solvents can have a viscosity in the range of from 10 to 1 ,500 Pascal seconds or from 100 to 1,000 Pascal seconds at 25°C.
- the alkoxylated triazine-arylhydroxy-aldehyde condensates of this invention can be used as polyisocyanate-reactive compounds to make polyurethanes and polyisocyanurate-based polymers.
- a reaction mixture is formed with at least one alkoxylated triazine-arylhydroxy-aldehyde condensate and at least one polyisocyanate.
- polyisocyanates that can be used include, but are not limited to m-phenylene diisocyanate, toluene-2,4-diisocyanate, toluene-2,6-diisocyanate, hexamethylene-1,6- diisocyanate, tetremethylene- 1 ,4-diisocyanate, cyclohexane- 1 ,4-diisocyanate, hexahydrotoluene diisocyanate, naphthylene-l,5-diisocyanate, methoxyphenyl-2,4- diisocyanate, diphenylmethane-4,4' -diisocyanate, 4,4'-biphenylene diisocyanate, 3,3
- the polyisocyanate is diphenylmethane- 4,4'-diisocyanate, diphenylmethane-2,4-diisocyanate, hexamethylene-1 ,6-diisocyanate, isophorone diisocyanate, toluene-2,4-diisocyanate, toluene-2,6-diisocyanate or mixtures thereof.
- Diphenylmethane-4,4 '-diisocyanate, diphenylmethane-2,4-diisocyanate and mixtures thereof are generically referred to as MDI and all can be used.
- Toluene-2,4- diisocyanate, toluene-2,6-diisocyanate and mixtures thereof are generically referred to as TDI and all can be used.
- any of the foregoing polyisocyanates can be modified to include urethane, urea, biuret, carbodiimide, allophonate, uretonimine, isocyanurate, amide, or like linkages.
- modified isocyanates of these types include various urethane group and/or urea group-containing prepolymers and so-called 'liquid MDF products and the like.
- the polyisocyanate can be a blocked isocyanate, where a standard polyisocyanate is prereacted with a blocking agent containing active hydrogen groups, which can then be deblocked at temperatures greater than 40°C (typically in the range of from 100°C to 190°C).
- blocking agents include, but are not limited to ⁇ -caprolactam, phenol, methyl ketone oxime, 1,2,4-triazole, and dimethyl malonate.
- Polyols which can be used in conjunction with the alkoxylated triazine- arylhydroxy-aldehyde condensate include polyether polyols.
- Suitable initiator compounds include, but are not limited to alkylene glycols, glycol ethers, glycerine, trimethylolpropane, sucrose, glucose, fructose, ethylene diamine, hexamethylene diamine, diethanolamine, monoethanolamine, piperazine, aminoethylpiperazine, diisopropanolamine, monoisopropanolamine, methanol amine, dimethanol amine, and toluene diamine.
- Polyester polyols can also be used as part of the isocyanate-reactive compound.
- Polyester polyols include reaction products of polyols, usually diols, with polycarboxylic acids or their anhydrides, usually dicarboxylic acids or dicarboxylic acid anhydrides.
- the polycarboxylic acids or anhydrides can be aliphatic, cycloaliphatic, aromatic, and/or heterocyclic.
- Mannich base polyols which are synthesized from Mannich bases, can also be used as part of the isocyanate-reactive compound.
- the alkoxylated triazine-arylhydroxy-aldehyde condensate is present in the isocyanate-reactive compound in a range of from about 5 weight percent to about 50 weight percent. Any and all ranges between 5 and 50 weight percent are included herein and disclosed herein; for example, the alkoxylated triazine-arylhydroxy- aldehyde condensate can be present in the isocyanate-reactive compound in a range of from 5 weight percent to 35 weight percent, from 15 weight percent to 25 weight percent, or from 9 weight percent to 21 weight percent.
- the alkoxylated triazine-arylhydroxy-aldehyde condensate can also act as a catalyst. Therefore, no extra catalyst is necessary for the reaction of the alkoxylated triazine-arylhydroxy-aldehyde condensate and polyisocyanate compound.
- the polyisocyanate and alkoxylated triazine-arylhydroxy-aldehyde condensate mixture can also include a catalyst.
- catalysts include, but are not limited to tertiary amines such as dimethylbenzylamine, 1,8- diaza(5,4,0)undecane-7, pentamethyldiethylenetriamine, dimethylcyclohexylamine, and triethylene diamine.
- Potassium salts such as potassium acetate and potassium octoate can also be used as catalysts.
- the alkoxylated triazine-arylhydroxyl- aldehyde condensate can also act as a catalyst.
- the alkoxylated triazine-arylhydroxy-aldehyde condensate also contains a diluent.
- diluents include, but are not limited to polyglycols such as ethylene glycol, glycerol, or diethylene glycol, etherified polyglycols such as monomethyl ether of ethylene glycol or dimethyl ether of ethylene glycol, and dibasic esters of acids such as diethyl adipate, dimethyl adipate, diethyl succinate, or dimethyl succinate. Mixtures of any of these diluents can also be used.
- additional materials can be present during the reaction of the polyisocyanate compound with the alkoxylated triazine- arylhydroxy- aldehyde condensate.
- these materials include but are not limited to surfactants, blowing agents, cell openers, fillers, pigments and/or colorants, desiccants, reinforcing agents, biocides, preservatives, antioxidants, flame retardants, and the like.
- the flame retardant is can be a phosphorus- containing flame retardant.
- phosphorus-containing flame retardants include, but are not limited to triethyl phosphate (TEP), triphenyl phosphate (TPP), trischloropropylphosphate, dimethylpropanephosphate, resorcinol bis(diphenylphosphate) (RDP), bisphenol A diphenyl phosphate (BADP), and tricresyl phosphate (TCP), dimethyl methylphosphonate (DMMP), diphenyl cresyl phosphate and aluminium diethyl phosphinate.
- TEP triethyl phosphate
- TPP triphenyl phosphate
- RDP resorcinol bis(diphenylphosphate)
- BADP bisphenol A diphenyl phosphate
- TCP tricresyl phosphate
- DMMP dimethyl methylphosphonate
- DMMP diphenyl cresyl
- the relative amounts of polyisocyanate and alkoxylated triazine arylhydroxy aldehyde condensate are selected to produce a polymer.
- the ratio of these components is generally referred to as the 'isocyanate index' which means 100 times the ratio of isocyanate groups to isocyanate-reactive groups provided by the alkoxylated triazine-arylhydroxy- aldehyde condensate.
- the isocyanate index is generally at least 50 and can be up to 1000 or more.
- Rigid polymers such as structural polyurethanes and rigid foams are typically made using an isocyanate index of from 90 to 200. When flexible or semi-flexible polymers are prepared, the isocyanate index is generally from 70 to 125. Polymers containing isocyanurate groups are often made at isocyanate indices of at least 150, up to 600 or more.
- the polyisocyanate compound and the alkoxylated triazine- arylhydroxy-aldehyde condensate are mixed and cured.
- the curing step is achieved by subjecting the reaction mixture to conditions sufficient to cause the polyisocyanate compound and alkoxylated triazine-arylhydroxy-aldehyde condensate to react to form the polymer.
- the polymer formed by the process of this invention can generally have a burn rate in the range of from 50 percent to 60 percent lower than a polyurethane composition that was not prepared with an alkoxylated triazine-arylhydroxy-aldehyde condensate.
- the polymer can also have a weight retention after burning in the range of from 70 percent to 115 percent higher than a polyurethane composition that was not prepared with an alkoxylated triazine-arylhydroxy-aldehyde condensate.
- the polymer can have a compressive strength at yield in the range of from 25 percent to 60 percent higher than a polyurethane composition that was not prepared with an alkoxylated triazine- arylhydroxy-aldehyde condensate.
- polymers can be made in accordance with the invention through the proper selection of particular alkoxylated-triazine-arylhydroxy-aldehyde condensates, particular polyisocyanates, the presence of optional materials as described below, and reaction conditions.
- the process of the invention can be used to produce polyurethane and/or polyisocyanurate polymers of various types, including rigid polyurethane foams, sealants and adhesives (including moisture-curable types), hot-melt powders, wood binders, cast elastomers, flexible or semi-flexible reaction injection molded parts, rigid structural composites, flexible polyurethane foams, binders, cushion and/or unitary backings for carpet and other textiles, semi-flexible foams, pipe insulation, automotive cavity sealing, automotive noise and/or vibration dampening, microcellular foams such as shoe soles, tire fillers and the like. These polymers can then be used to manufacture articles.
- compositions were prepared using methods described in US Patent
- Example 10 The alkoxylated triazine-arylhydroxy-aldehyde condensate from Example 3 was flaked and fed into a grinding mill and an amount of methylene diphenyl diisocyanate was also fed to achieve a desired isocyanate ratio of 1 : 1 based on the hydroxyl equivalent weight of the triazine-arylhydroxy-aldehyde condensate.
- the composition was ground to a mesh size of 50-100% through 200 mesh.
- the powdered composition was cured above the melting point or softening point of the resulting mixture to yield a cross-linked polyurethane.
- Example 10 Example 10:
- Example 4 were dissolved in 20 grams of triethyl phosphate and 10 grams of ethylene glycol to yield a viscous solution with an approximate hydroxyl equivalent weight of 98. This mixture was further formulated with cyclopentane as a surfactant and emulsified. A polymeric isocyanate was added to achieve a specific isocyanate ratio of 1 : 1 and then mixed to create a polyurethane foam.
- An ARES-G2 rheometer (TA Instruments) equipped with stainless steel parallel plates was operated under rotational mode to determine the viscosities of the formulation from Example 3 at 150°C, 140°C, and 130°C.
- the viscosity was determined from a "zero-shear" approximation in which the viscosity is measured as a function of shear rate (0.1-100 1/s).
- the zero shear viscosity was determined by averaging the viscosity in the Newtonian region, which is approximately 1-100 1/s.
- Ten data points were measured for every magnitude change of shear rate such as 10 points between 0.1 and 1 1/s. The lower temperature was determined when the materials exhibited non-Newtonian behavior such as shear thinning.
- an alkoxylated triazine-arylhydroxy- aldehyde condensate can be used as a rheology modifier for polyurethane crosslinking systems.
- Example 12 Effect of Introducing Alkoxylated Triazine-Arylhydroxy- Aldehyde Condensate Into a typical PU Formulation for Rigid Foams
- Test Formulations #1 and #2 were prepared using the two formulations shown in Table 5, below.
- the alkoxylated triazine-arylhydroxy-aldehyde condensate of the current invention was mixed into the reference carbohydrate-based aliphatic polyol (Reference Polyol #1) at a 80:20 ratio of Reference Polyol #1 to the ethoxylated condensate from Example 3 along with other components listed in the Table, at 100°C in a cup at 2200 RPM using Speed Mixer DAC 400 FV.
- Reference Formulation #1 Reference Polyol #1 was blended with other components in the same manner as described above.
- Test Formulation #2 Reference Polyol #1 was blended with a conventional aromatic-based polyol and the ethoxylated condensate of Example 3.
- Foams were prepared using a high-torque mixer (CRAFSTMAN 10-Inch
- Dabco ® 33LV an amine catalyst available from Evonik.
- Niax A-l a catalyst available from Momentive Performance Materials.
- Rubinate® M a polymeric MDI isocyanate, available from Huntsman.
- the second set of five specimens are conditioned in an air circulating oven for 168 ⁇ 2 h at 70 ⁇ 2 °C, and then cooled in a desiccator for at least 4 hours at room temperature prior to testing.
- 6 specimens are cut prior to testing from foam aged at room conditions (ambient temperature and humidity) for a minimum of 7 days after preparation of the foam.
- Table 6 shows properties of foams prepared using three different formulations.
- One reference formulation used a carbohydrate-based aliphatic polyol.
- the two test formulations (#3 and #4) are prepared from various amounts of the carbohydrate- based aliphatic polyol, a conventional aromatic-based polyol, and the ethoxylated triazine- arylhydroxy-aldehyde condensate of Example 3. These formulations were prepared as described in Example 12, above.
- foams prepared from the alkoxylated triazine- arylhydroxy-aldehyde condensate provided slower burn rates, higher weight retentions, and good mechanical properties.
- the compressive strength at yield and the compressive strength at maximum load significantly increased with the introduction of the alkoxylated triazine- arylhydroxy-aldehyde condensate into the formulation.
- the compressive strength is dependent on the foam density.
- this increase in the compressive strength with introduction of alkoxylated triazine-arylhydroxy-aldehyde condensate into the formulation is much greater than the possible effect of an increase in the foam density.
- polymers prepared with alkoxylated triazine-arylhydroxy-aldehyde condensates have cream times that are about 4 to 19 percent lower, gel times that are about 35 to 42 percent lower, rise times that are about 23 to 34 percent lower, and tack-free times that are about 32 to 43 percent lower than the reference formulation that was not prepared with an alkoxylated triazine-arylhydroxy-aldehyde condensate.
- foams prepared from the alkoxylated triazine-arylhydroxy- aldehyde condensate have higher reactivites than the foam prepared from the reference formulation.
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US15/713,583 US10435503B2 (en) | 2017-09-22 | 2017-09-22 | Compositions for polyurethane applications |
US15/713,577 US10118905B1 (en) | 2017-09-22 | 2017-09-22 | Compositions and methods to produce Alkoxylated triazine-arylhydroxy-aldehyde condensates |
PCT/US2018/051761 WO2019060422A2 (en) | 2017-09-22 | 2018-09-19 | Novel compositions and methods to produce alkoxylated triazine-arylhydroxy-aldehyde condensates |
Publications (2)
Publication Number | Publication Date |
---|---|
EP3684760A2 true EP3684760A2 (en) | 2020-07-29 |
EP3684760A4 EP3684760A4 (en) | 2021-11-10 |
Family
ID=65809844
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP18857763.9A Pending EP3684760A4 (en) | 2017-09-22 | 2018-09-19 | Novel compositions and methods to produce alkoxylated triazine-arylhydroxy-aldehyde condensates |
EP18857994.0A Pending EP3684830A4 (en) | 2017-09-22 | 2018-09-19 | Novel compositions for polyurethane applications |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP18857994.0A Pending EP3684830A4 (en) | 2017-09-22 | 2018-09-19 | Novel compositions for polyurethane applications |
Country Status (3)
Country | Link |
---|---|
EP (2) | EP3684760A4 (en) |
CN (2) | CN111094257A (en) |
WO (2) | WO2019060422A2 (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3833699A4 (en) * | 2018-07-24 | 2022-08-03 | Bakelite UK Holding Ltd. | Novel compositions and methods to produce alkoxylated triazine-arylhydroxy-aldehyde condensates |
CN112638972B (en) * | 2018-07-24 | 2023-05-30 | 巴克莱特英国控股有限公司 | Novel compositions and methods for producing alkoxylated triazine-arylhydroxy-aldehyde condensates |
CN111848919A (en) * | 2020-08-07 | 2020-10-30 | 宁波耀众模塑科技有限公司 | Flame retardant for polyurethane foaming product |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3265668A (en) * | 1963-04-05 | 1966-08-09 | Pittsburgh Plate Glass Co | Reaction products of amino-s-triazine and alkylene carbonates |
US3399151A (en) * | 1963-04-25 | 1968-08-27 | Olin Mathieson | Polyurethane foam prepared from an oxyalkylated polyamino-1, 3, 5-triazine-organic polyisocyanate reaction product |
US3497465A (en) * | 1966-11-28 | 1970-02-24 | Hooker Chemical Corp | Low temperature-stable polyurethane foams and compositions containing derivatives of phenol-aldehyde resins useful for preparing said polyurethanes |
DE2807744A1 (en) * | 1978-02-23 | 1979-09-06 | Basf Ag | METHOD FOR MANUFACTURING MODIFIED AMINOPLASTIC RESINS |
JPS56133333A (en) * | 1980-03-25 | 1981-10-19 | Asahi Glass Co Ltd | Preparation of polyol for raw material of rigid polyurethane foam |
US4487852A (en) * | 1983-10-25 | 1984-12-11 | Texaco Inc. | Modified Mannich condensates and manufacture of rigid polyurethane foam with alkoxylation products thereof |
JPS61189277A (en) * | 1985-02-15 | 1986-08-22 | Idemitsu Kosan Co Ltd | Triazine derivative, production thereof, and herbicide containing said derivative as active component |
US5059670A (en) * | 1990-04-27 | 1991-10-22 | Arco Chemical Technology, Inc. | Thermosettable compositions containing alkoxylated aromatic compounds |
DE10136321C1 (en) * | 2001-07-26 | 2002-12-12 | Agrolinz Melamin Gmbh Linz | Polymer derived from triazine derivatives for production of semi finished products and molding materials, films, fibers, microcapsules in the automobile, domestic products, electrical technology, and electronics industries |
DE10313200A1 (en) * | 2003-03-19 | 2004-10-07 | Ami-Agrolinz Melamine International Gmbh | Prepregs for fiber composites of high strength and elasticity |
JP2008239865A (en) * | 2007-03-28 | 2008-10-09 | Dic Corp | Thermosetting polyurethane resin composition |
US9249251B2 (en) * | 2010-08-17 | 2016-02-02 | Hexion Inc. | Compositions and methods to produce triazine-arylhydroxy-aldehyde condensates with improved solubility |
PL3209730T3 (en) * | 2014-10-21 | 2022-05-23 | Momentive Performance Materials Inc. | Rigid polyurethane foams comprising modified phenolic resins additives |
WO2017160362A1 (en) * | 2016-03-17 | 2017-09-21 | Huntsman Petrochemical Llc | Metal salts of aminio acid triazines as polyurethane and polyisocyanurate catalysts |
US10118905B1 (en) * | 2017-09-22 | 2018-11-06 | Hexion Inc. | Compositions and methods to produce Alkoxylated triazine-arylhydroxy-aldehyde condensates |
-
2018
- 2018-09-19 CN CN201880061050.7A patent/CN111094257A/en active Pending
- 2018-09-19 EP EP18857763.9A patent/EP3684760A4/en active Pending
- 2018-09-19 WO PCT/US2018/051761 patent/WO2019060422A2/en unknown
- 2018-09-19 CN CN201880061043.7A patent/CN111108136B/en active Active
- 2018-09-19 WO PCT/US2018/051766 patent/WO2019060426A1/en unknown
- 2018-09-19 EP EP18857994.0A patent/EP3684830A4/en active Pending
Also Published As
Publication number | Publication date |
---|---|
EP3684830A1 (en) | 2020-07-29 |
WO2019060426A1 (en) | 2019-03-28 |
WO2019060422A2 (en) | 2019-03-28 |
CN111094257A (en) | 2020-05-01 |
WO2019060422A3 (en) | 2019-05-02 |
EP3684760A4 (en) | 2021-11-10 |
CN111108136B (en) | 2023-03-21 |
EP3684830A4 (en) | 2021-08-11 |
CN111108136A (en) | 2020-05-05 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US11028219B2 (en) | Compositions for polyurethane applications | |
US10118905B1 (en) | Compositions and methods to produce Alkoxylated triazine-arylhydroxy-aldehyde condensates | |
EP2231742B1 (en) | Thermally insulating isocyanate-based foams | |
CN111108136B (en) | Compositions for polyurethane applications | |
EP3044247B1 (en) | Pipa based combustion-modified polyurethane foam | |
US10640475B2 (en) | Compositions and methods to produce alkoxylated triazine-arlhydroxy-aldehyde condensates | |
EP1603961A1 (en) | Low amine emission polyurethane foam | |
JP7083906B2 (en) | Polyol composition and polyurethane foam | |
US20190144674A1 (en) | Alkoxylation of lignins | |
US10604614B2 (en) | Compositions and methods to produce alkoxylated triazine-arylhydroxy-aldehyde condensates | |
US8318829B2 (en) | Methylene bis(cyclohexylamine)-initiated polyols and rigid polyurethane foam made therefrom | |
WO2019099405A1 (en) | Alkoxylated lignin for polyurethane applications | |
KR102581917B1 (en) | Novel compositions and methods for preparing alkoxylated triazine-arylhydroxy-aldehyde condensates | |
EP0116310B1 (en) | Halogenated phenolic polyols and rigid cellular compositions made therefrom | |
US20190144595A1 (en) | Alkoxylated lignin for polyurethane applications | |
JP2020535254A (en) | Manufacture of polyurethane foam | |
KR102574985B1 (en) | Novel compositions and methods for preparing alkoxylated triazine-arylhydroxy-aldehyde condensates | |
JPH02292321A (en) | Fiber-reinforced rigid polyurethane foam and polyol component for it | |
EP0364156B1 (en) | Closed cell rigid polyurethane foam laminates | |
US20110077314A1 (en) | 1,3- or 1,4-bis(aminomethyl)cyclohexane-initiated polyols and rigid polyurethane foam made therefrom | |
US4555530A (en) | Halogenated phenolic polyols and rigid cellular compositions made therefrom | |
JP3531220B2 (en) | Manufacturing method of rigid foam synthetic resin | |
JP2023002957A (en) | Polyether polyol, method for producing the same, composition for hard polyurethane foam, hard polyurethane foam and method for producing the same | |
CN117003978A (en) | Preparation method and application of bio-based polymer polyol |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE |
|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE |
|
17P | Request for examination filed |
Effective date: 20200422 |
|
AK | Designated contracting states |
Kind code of ref document: A2 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
AX | Request for extension of the european patent |
Extension state: BA ME |
|
DAV | Request for validation of the european patent (deleted) | ||
DAX | Request for extension of the european patent (deleted) | ||
RIC1 | Information provided on ipc code assigned before grant |
Ipc: C07D 251/18 20060101AFI20210514BHEP Ipc: C07D 251/64 20060101ALI20210514BHEP Ipc: C07D 317/38 20060101ALI20210514BHEP Ipc: C08K 5/3462 20060101ALI20210514BHEP Ipc: C08G 14/10 20060101ALI20210514BHEP Ipc: C08G 14/12 20060101ALI20210514BHEP Ipc: C08G 18/54 20060101ALI20210514BHEP |
|
A4 | Supplementary search report drawn up and despatched |
Effective date: 20211013 |
|
RIC1 | Information provided on ipc code assigned before grant |
Ipc: C08G 18/54 20060101ALI20211007BHEP Ipc: C08G 14/12 20060101ALI20211007BHEP Ipc: C08G 14/10 20060101ALI20211007BHEP Ipc: C08K 5/3462 20060101ALI20211007BHEP Ipc: C07D 317/38 20060101ALI20211007BHEP Ipc: C07D 251/64 20060101ALI20211007BHEP Ipc: C07D 251/18 20060101AFI20211007BHEP |
|
RAP1 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: BAKELITE UK HOLDING LTD. |
|
111Z | Information provided on other rights and legal means of execution |
Free format text: AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR Effective date: 20221020 |
|
111Z | Information provided on other rights and legal means of execution |
Free format text: AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR Effective date: 20221020 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: EXAMINATION IS IN PROGRESS |
|
17Q | First examination report despatched |
Effective date: 20240214 |