CN117603056A - 一种浅色聚氨酯固化剂的制备方法 - Google Patents
一种浅色聚氨酯固化剂的制备方法 Download PDFInfo
- Publication number
- CN117603056A CN117603056A CN202311632198.0A CN202311632198A CN117603056A CN 117603056 A CN117603056 A CN 117603056A CN 202311632198 A CN202311632198 A CN 202311632198A CN 117603056 A CN117603056 A CN 117603056A
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- China
- Prior art keywords
- light
- hydroxylamine
- curing agent
- chloroaniline
- moca
- 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
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 22
- 239000004814 polyurethane Substances 0.000 title claims abstract description 22
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 claims abstract description 44
- 241001112258 Moca Species 0.000 claims abstract description 44
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 29
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 claims abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 22
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 claims abstract description 20
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 18
- 239000011574 phosphorus Substances 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 15
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000003860 storage Methods 0.000 claims abstract description 12
- 238000005406 washing Methods 0.000 claims abstract description 11
- 235000010388 propyl gallate Nutrition 0.000 claims abstract description 10
- 239000000473 propyl gallate Substances 0.000 claims abstract description 10
- 229940075579 propyl gallate Drugs 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 238000001816 cooling Methods 0.000 claims abstract description 9
- 239000007788 liquid Substances 0.000 claims abstract description 9
- 238000006482 condensation reaction Methods 0.000 claims abstract description 6
- 150000002443 hydroxylamines Chemical class 0.000 claims abstract description 6
- 239000011541 reaction mixture Substances 0.000 claims abstract description 5
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 4
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 4
- -1 hydroxylamine compound Chemical class 0.000 claims description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 claims description 12
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 9
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 8
- 239000012074 organic phase Substances 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- VFPFQHQNJCMNBZ-UHFFFAOYSA-N ethyl gallate Chemical compound CCOC(=O)C1=CC(O)=C(O)C(O)=C1 VFPFQHQNJCMNBZ-UHFFFAOYSA-N 0.000 claims description 6
- 229940074391 gallic acid Drugs 0.000 claims description 6
- 235000004515 gallic acid Nutrition 0.000 claims description 6
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 6
- 239000012071 phase Substances 0.000 claims description 5
- 150000008301 phosphite esters Chemical class 0.000 claims description 5
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 claims description 4
- ODHYIQOBTIWVRZ-UHFFFAOYSA-N n-propan-2-ylhydroxylamine Chemical compound CC(C)NO ODHYIQOBTIWVRZ-UHFFFAOYSA-N 0.000 claims description 4
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 claims description 4
- YBMTWYWCLVMFFD-UHFFFAOYSA-N 3-methylbutyl 3,4,5-trihydroxybenzoate Chemical compound CC(C)CCOC(=O)C1=CC(O)=C(O)C(O)=C1 YBMTWYWCLVMFFD-UHFFFAOYSA-N 0.000 claims description 3
- 239000004262 Ethyl gallate Substances 0.000 claims description 3
- 235000019277 ethyl gallate Nutrition 0.000 claims description 3
- 239000008098 formaldehyde solution Substances 0.000 claims description 3
- 239000011259 mixed solution Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- XZZWOTQMUOIIFX-UHFFFAOYSA-N 1-(2-diphenoxyphosphanyloxypropoxy)propan-2-yl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC(C)COCC(C)OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 XZZWOTQMUOIIFX-UHFFFAOYSA-N 0.000 claims description 2
- PZRWFKGUFWPFID-UHFFFAOYSA-N 3,9-dioctadecoxy-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCCCCCCCCCCCC)OCC21COP(OCCCCCCCCCCCCCCCCCC)OC2 PZRWFKGUFWPFID-UHFFFAOYSA-N 0.000 claims description 2
- 229920001174 Diethylhydroxylamine Polymers 0.000 claims description 2
- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical compound CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims description 2
- PAZXUKOJTOTKBK-UHFFFAOYSA-N n,n-dibutylhydroxylamine Chemical compound CCCCN(O)CCCC PAZXUKOJTOTKBK-UHFFFAOYSA-N 0.000 claims description 2
- VMESOKCXSYNAKD-UHFFFAOYSA-N n,n-dimethylhydroxylamine Chemical compound CN(C)O VMESOKCXSYNAKD-UHFFFAOYSA-N 0.000 claims description 2
- ZKXYINRKIDSREX-UHFFFAOYSA-N n,n-dipropylhydroxylamine Chemical compound CCCN(O)CCC ZKXYINRKIDSREX-UHFFFAOYSA-N 0.000 claims description 2
- RRUADNNEIGVWSQ-UHFFFAOYSA-N n-ethyl-n-methylhydroxylamine Chemical compound CCN(C)O RRUADNNEIGVWSQ-UHFFFAOYSA-N 0.000 claims description 2
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 claims description 2
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 claims description 2
- WHAFDJWJDDPMDO-UHFFFAOYSA-N trimethyl(phenyl)phosphanium Chemical compound C[P+](C)(C)C1=CC=CC=C1 WHAFDJWJDDPMDO-UHFFFAOYSA-N 0.000 claims description 2
- IUURMAINMLIZMX-UHFFFAOYSA-N tris(2-nonylphenyl)phosphane Chemical compound CCCCCCCCCC1=CC=CC=C1P(C=1C(=CC=CC=1)CCCCCCCCC)C1=CC=CC=C1CCCCCCCCC IUURMAINMLIZMX-UHFFFAOYSA-N 0.000 claims description 2
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 abstract description 18
- 230000008569 process Effects 0.000 abstract description 18
- 230000008859 change Effects 0.000 abstract description 9
- 238000002845 discoloration Methods 0.000 description 23
- 238000003786 synthesis reaction Methods 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000002245 particle Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 238000009472 formulation Methods 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 230000002401 inhibitory effect Effects 0.000 description 7
- 150000004982 aromatic amines Chemical group 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 4
- 235000003891 ferrous sulphate Nutrition 0.000 description 4
- 239000011790 ferrous sulphate Substances 0.000 description 4
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 4
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical group OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 150000004984 aromatic diamines Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Chemical group O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
- 235000011150 stannous chloride Nutrition 0.000 description 3
- 239000001119 stannous chloride Substances 0.000 description 3
- DRGIDRZFKRLQTE-UHFFFAOYSA-N 2-chloroaniline;hydron;chloride Chemical compound Cl.NC1=CC=CC=C1Cl DRGIDRZFKRLQTE-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical group OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920003225 polyurethane elastomer Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- HGXVKAPCSIXGAK-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine;4,6-diethyl-2-methylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(C)=C1N.CCC1=CC(C)=C(N)C(CC)=C1N HGXVKAPCSIXGAK-UHFFFAOYSA-N 0.000 description 1
- AGJBKFAPBKOEGA-UHFFFAOYSA-M 2-methoxyethylmercury(1+);acetate Chemical compound COCC[Hg]OC(C)=O AGJBKFAPBKOEGA-UHFFFAOYSA-M 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
- 239000005711 Benzoic acid Substances 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- RJTANRZEWTUVMA-UHFFFAOYSA-N boron;n-methylmethanamine Chemical compound [B].CNC RJTANRZEWTUVMA-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000032798 delamination Effects 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229940075933 dithionate Drugs 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical group [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229960002089 ferrous chloride Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- MGJURKDLIJVDEO-UHFFFAOYSA-N formaldehyde;hydrate Chemical compound O.O=C MGJURKDLIJVDEO-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical group [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical group [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- UOULCEYHQNCFFH-UHFFFAOYSA-M sodium;hydroxymethanesulfonate Chemical compound [Na+].OCS([O-])(=O)=O UOULCEYHQNCFFH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical group OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/78—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton from carbonyl compounds, e.g. from formaldehyde, and amines having amino groups bound to carbon atoms of six-membered aromatic rings, with formation of methylene-diarylamines
-
- 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
- C08G18/3802—Low-molecular-weight compounds having heteroatoms other than oxygen having halogens
- C08G18/3814—Polyamines
Landscapes
- Chemical & Material Sciences (AREA)
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Abstract
一种浅色聚氨酯固化剂的制备方法,由邻氯苯胺、甲醛在盐酸催化下进行缩合反应时加入羟胺类化合物,缩合反应得到浅黄色反应混合物,在90~105℃中和分液后,油相经水洗、除水后加入含磷化合物和没食子酸酯,冷却造粒后得到浅色且储存稳定的MOCA产品。本发明在反应初期加入盐酸羟胺,得到浅色的MOCA产品,在MOCA凝固前,加入三苯基膦和没食子酸丙酯复配的变色抑制剂,抑制或延缓储存过程的颜色变化。
Description
技术领域
本发明属于有机化工合成技术领域,涉及一种浅色聚氨酯固化剂的制备方法。
背景技术
3,3'-二氯-4,4'-二苯基甲烷二胺(MOCA)是一种用于聚氨酯弹性体体系的芳香族胺类扩链剂,性价比高。由MOCA为固化剂的浇注型聚氨酯弹性体主要用于生产各种耐磨弹性制品以及防水涂料、胶黏剂等,广泛应用于机械、电子电器、交通运输、土木建筑、体育休闲等工业和民用领域。MOCA作为一种重要助剂,其色泽会影响到弹性体聚氨酯制品的色泽。
与醇类化合物相比,芳香族胺类化合物更容易变色,在生产和存储过程中,如果接触光和空气颜色会逐渐变深,由无色变成浅黄色、黄色、琥珀色、深褐色直至黑色,影响产品质量和下游应用,所以几十年来,为了抑制芳香族胺类的变色,已经有不少抑制芳香族胺变色的化合物被报道,这些延缓颜色变化的稳定剂可称作为变色抑制剂,见于报道的有硼氢化钠、硼氢化钾、硼烷-二甲胺络合物、硫化钠、硫氢化钠、连二硫酸盐、连二亚硫酸盐、亚硫酸盐、亚硫酸氢盐、硫代硫酸盐、水合肼、含游离伯氨基的烷基取代肼、甲醛亚硫酸氢钠、氯化亚锡、硫酸亚铁、氯化亚铁、氢化铝锂、氢化铝钠、抗坏血酸、甲酸、乙酸、苯甲酸、氢氧化钠、氢氧化锂、二甲苯基双胍、邻甲苯基双胍、N-乙酰乙酰苯胺、二烷基二硫代氨基甲酸钠、N-烷基环丙胺、N-烷基吡咯、抗氧剂BHT、2,4-二甲基-6-叔丁基苯酚、抗氧剂264、磷酸酯、亚磷酸酯、膦化合物、光稳定剂等,它们或多或少可延长颜色变深的时间。但是对于不同的芳香族胺,这些变色抑制剂的效果不一样,对于合成浅色且储存稳定的MOCA适用的不多;有的变色抑制剂只是在短期内抑制颜色变深有效果,不宜用作储存稳定剂;有的芳胺体系在变色抑制剂如果用量低则抑制变色的时间短,用量较大的情况下效果变好,甚至用量需高达0.5%以上,这就会影响产品的纯度;有的变色抑制剂含金属离子,可能对后续聚氨酯材料的生产有影响。杜邦公司在专利US3393239中介绍,加0.01%~1%的碱金属氢氧化物如NaOH、KOH或LiOH可抑制MOCA熔融变色,但是在MOCA和聚醚多元醇配制的固化剂组合物中引入碱性物质和金属离子对反应体系可能产生明显的催化作用,使异氰酸酯基发生三聚反应,缩短可操作时间,且影响制品性能。CN100579953C介绍在MOCA、DETDA、DMTDA和MEMDA等芳香族二胺中添加亚磷酸酯、芳烷基膦、水合肼中的一种或两种以上可延长浅色时间,对MOCA熔融后颜色变深抑制有效果,没有研究合成过程的颜色抑制,且残留水合肼对后续制备聚氨酯有影响。CN1906151B介绍用膦化合物作为包括MOCA在内的芳香族二胺的热稳定剂,但该专利只介绍了产品的热熔融稳定性,没有介绍生产过程芳香族胺的颜色稳定性,且用量相对较高。CN105037178提出的4种物质组合抗氧剂技术对于MOCA的生产和储存不适用,没达到较优效果。
所以,针对现有的MOCA生产工艺,研究抑制其变色的方法,使产品在较长时间储存和运输过程中延缓变色,甚至基本上不变色变质,对产品的生产、储存和应用都具有重要意义。
发明内容
本发明的目的在于提供一种浅色聚氨酯固化剂的制备方法。
为实现上述目的及其他相关目的,本发明提供的技术方案是:一种浅色聚氨酯固化剂的制备方法,由邻氯苯胺、甲醛在盐酸催化下进行缩合反应时加入羟胺类化合物,缩合反应得到浅黄色反应混合物,在90~105℃中和分液后,油相经水洗、除水后加入含磷化合物和没食子酸酯,冷却造粒后得到浅色且储存稳定的MOCA产品。。
优选的技术方案为:所述羟胺类化合物为盐酸羟胺、羟胺、二甲基羟胺、二乙基羟胺、 二丙基羟胺、异丙基羟胺、二丁基羟胺、甲基乙基羟胺、N-异丙基羟胺、N,N-二烷基羟胺和N,N-二羟烷基羟胺中的至少一种;羟胺类化合物加入量为邻氯苯胺的质量的0.2%~1.0%。
优选的技术方案为:所述含磷化合物为膦化合物和亚磷酸酯中的至少一种;膦化合物为三苯基膦、三甲苯基膦、三丁基膦、三(对-甲基苯基)膦和三 (壬基苯基)膦中的至少一种;亚磷酸酯为亚磷酸三苯酯、亚磷酸三丁酯、亚磷酸三(壬基苯)酯、二亚磷酸二硬脂基季戊四醇酯、二亚磷酸季戊四醇二辛醇酯、亚磷酸三(2,4-二叔丁基苯基)酯、亚磷酸三(壬基苯)酯、四苯基二丙二醇二亚磷酸酯中的至少一种;含磷化合物用量为50~200ppm。
优选的技术方案为:没食子酸酯为没食子酸丙酯、没食子酸乙酯和没食子酸异戊酯中的至少一种,用量为10~100ppm。
优选的技术方案为:盐酸与邻氯苯胺的摩尔比为1.1~1.5∶1;甲醛与邻氯苯胺的摩尔比0.49~0.53∶1。
优选的技术方案为:在水、羟胺类化合物和盐酸组成的混合液中加入邻氯苯胺,然后加入甲醛溶液,温度控制在30~50℃,接着升温至75-85℃,再在80~95℃阶梯升温反应2~3小时,维持95~103℃加入氢氧化钠水溶液中和至pH值为8~9,静置待液体分层,倾析分离掉水相,有机相用95~100℃水洗涤,抽真空除去水分和残留邻氯苯胺,再加入含磷化合物和没食子酸酯,溶解均匀后冷却造粒。
由于上述技术方案运用,本发明与现有技术相比具有的优点是:
采用本发明的方法后,不仅在合成过程中MOCA熔融液的颜色维持微黄至浅黄色,而且MOCA固体颗粒的颜色浅,MOCA在120℃的熔融液可维持24h不明显变色,MOCA颗粒储存12个月外观颜色及其熔融液颜色或其有机溶液的颜色没有明显变深,仍可维持浅黄色~黄色。
具体实施方式
以下由特定的具体实施例说明本发明的实施方式,熟悉此技术的人士可由本说明书所揭露的内容轻易地了解本发明的其他优点及功效。
实施例1:一种浅色聚氨酯固化剂的制备方法
在反应容器内加入300份水、150份30%盐酸溶液和1份盐酸羟胺,搅拌均匀,加入127.6份邻氯苯胺搅拌0.5小时,40~60℃加入41份37%甲醛溶液,1小时后温度升到90℃,此时为均相状态,90~95℃保温2个小时,形成MOCA盐酸盐稀浆状物,然后维持95℃缓慢加入168份31%NaOH水溶液,在100℃左右激烈搅拌10~15分钟,静置分层,倾析分离掉含盐水相(另处理,并蒸发成工业盐回收利用),底层有机相用各80份95~100℃热水激烈搅拌下洗涤(分出水相)2次,有机相加热到120℃真空脱水,然后加入加入0.025份亚磷酸三苯酯和0.02份没食子酸丙酯,搅拌10分钟溶解均匀,将过滤得到微黄色至浅黄色的MOCA熔融液(熔点102~104℃)冷却结晶,得到白色至微黄色MOCA颗粒130份。
比较例1:
采用实施例1的配方和合成工艺,未添加亚磷酸三苯酯和没食子酸丙酯。初始产物熔融液和颗粒颜色与实施例1基本相同。
比较例2:
采用实施例1的配方和合成工艺,用3份硫酸亚铁替代盐酸羟胺,未添加亚磷酸三苯酯和没食子酸丙酯。初始产物熔融液为浅黄色,MOCA颗粒浅黄绿色。
比较例3:
采用实施例1的配方和合成工艺,亚磷酸三苯酯提前在分层后添加。
比较例4:
采用实施例1的配方和合成工艺,后添加的变色抑制剂为0.03%三苯基膦。
比较例5:
采用实施例1的配方和合成工艺,后添加的变色抑制剂为0.015%没食子酸丙酯。
实施例2:一种浅色聚氨酯固化剂的制备方法
采用实施例1的配方和合成工艺,变色抑制剂用量也与实施例相同,只是磷化合物换用亚磷酸酯类辅助抗氧剂168。初始产物熔融液和颗粒颜色与实施例1基本相同。
实施例3:一种浅色聚氨酯固化剂的制备方法
采用实施例1的配方和合成工艺,变色抑制剂用量也与实施例相同,只是磷化合物换用三苯基膦。初始产物熔融液和颗粒颜色与实施例1基本相同。
实施例4:一种浅色聚氨酯固化剂的制备方法
采用实施例1的配方和合成工艺,磷化合物换用0.01%三苯基膦,没食子酸丙酯用量降低为0.01%。初始产物熔融液和颗粒颜色与实施例1基本相同。
实施例5:一种浅色聚氨酯固化剂的制备方法
采用实施例3的配方和合成工艺,三苯基膦用量增加到0.04%,没食子酸丙酯用量降低到0.01%。初始产物熔融液和颗粒颜色与实施例1基本相同。
颜色稳定性试验:
(1)热稳定性试验是将MOCA在120℃熔融,熔融稳定性是将玻璃瓶装的MOCA熔融液在120℃烘箱中放置24小时后评价;
(2)UV加速光照试验是将MOCA溶解在丙酮中得到50%MOCA溶液,装在带透明盖的无色石英玻璃瓶(或透明塑料瓶)中,在一装有50W LED紫外灯的烘箱中分别在3小时和8小时取出检测色度。各样品与灯管的距离相同。
(3)储存试验,将MOCA颗粒摊铺在φ10cm培养皿,放在靠窗位置,让自然光照射在样品上,观察3个月后颗粒上表层的色泽。
颜色评价方法:将MOCA溶解在丙酮中配成50%的丙酮溶液装在比色管中,采用Lovibond微电脑全自动色度分析测定仪PFXi 995/P测Gardner色度;熔融液、溶液和MOCA颗粒的颜色采取目测方法。
变色抑制剂对MOCA色度的影响见下表。
实施例6:一种浅色聚氨酯固化剂的制备方法
一种浅色3,3'-二氯-4,4'-二苯基甲烷二胺(MOCA)的生产方法,由邻氯苯胺、甲醛在盐酸催化下进行缩合反应时加入羟胺类变色抑制剂,经过一系列反应,得到浅黄色反应混合物,在90℃中和分液后,油相中经水洗、除水后加入少量变色抑制剂含磷化合物和没食子酸酯,冷却造粒,得到浅色且储存稳定的MOCA产品。
优选的实施方式为,加入的羟胺类化合物包括盐酸羟胺、羟胺等,加入量为邻氯苯胺的0.2%(质量分数,下同)。
优选的实施方式为,含磷化合物为三苯基膦和三甲苯基膦按照1:1的质量比例构成的混合物,用量为50ppm。
优选的实施方式为,在熔融液态MOCA中加入的没食子酸酯为没食子酸丙酯、没食子酸乙酯按照1:2的质量比例构成的混合物,用量为100ppm。
优选的实施方式为, MOCA的合成原料配方是:盐酸与邻氯苯胺的摩尔比范围在1.1∶1;甲醛与邻氯苯胺的摩尔比0.49∶1。
优选的实施方式为,MOCA的基本合成工艺步骤为:在含羟胺的邻氯苯胺盐酸盐水溶液中1小时内缓慢加入甲醛水溶液,温度控制在30℃,并在1小时内缓慢升温至80℃,再在80℃阶梯升温反应2小时,维持95℃加入氢氧化钠水溶液中和至pH值为8,静置待液体分层,倾析分离掉水相,有机相用95℃水洗涤,抽真空除去水分和残留邻氯苯胺,再加入少量含磷化合物和没食子酸酯,溶解均匀后冷却造粒。
实施例7:一种浅色聚氨酯固化剂的制备方法
本发明提出了制备浅色MOCA,并在较长时间内抑制其颜色变深的方法。主要包括两个方面,一是在生产过程消除导致变色的因素,抑制氧化,以获得浅色产品,二是在产品中添加少量复配变色抑制剂,利用协同效应在较低用量下,明显延缓产品颜色变深的速度。
为了解决合成因素导致的MOCA产品颜色深的问题,通氮气保护是一种办法,但不可避免合成过程颜色仍有一定程度变深的倾向。有的合成技术将氯化亚锡、氯化亚铁、硫酸亚铁、亚硫酸氢钠这些具有还原性的变色抑制剂与邻氯苯胺盐酸盐混合,可消除反应体系的溶解氧和空气中氧气的影响,但是因为水溶性还原性离子在中和除盐过程中大部分被除去,MOCA有机相基本上不含还原性物质,产品在后处理过程容易变色。
本发明采用常规的MOCA生产工艺合成MOCA,与现有技术不同之处在于,首先在混合原料体系添加一种防止反应物反应过程中颜色变深的还原性有机物——羟胺类化合物,与亚硫酸盐、氯化亚锡、硫酸亚铁等相比,本发明采用的羟胺既可以去除反应体系的游离氧,起到色稳定作用,羟胺化合物可以与甲醛反应,并且可连接到苯环上而不产生不容易分离的杂质,残留的羟胺可在一定时间内仍有抑制颜色变深的效果。并且,针对热态产物遇到空气容易变色的问题,在后处理工序添加少量的含抗氧剂在内防止芳香族二胺产物变色的物质,以防止后处理过程的变色,并且抑制产品储存过程的颜色变深。
加入的羟胺类化合物包括盐酸羟胺、羟胺等,加入量为邻氯苯胺的1.5%(质量分数,下同)。
含磷元素的变色抑制剂为三苯基膦与亚磷酸三(2,4-二叔丁基苯基)酯按照2:1的质量比例构成的混合物,用量为150ppm。
没食子酸酯为没食子酸异戊酯,用量为100ppm。
以上的变色抑制剂大多数有工业品。
以质量分数计,含磷化合物和没食子酸酯的总量为MOCA的0.1%以下。
MOCA的基本合成步骤包括:(一)35℃在水、羟胺和盐酸溶液的混合液中加入邻氯苯胺,使邻氯苯胺与盐酸反应形成盐酸盐而溶解于水中或形成低黏度浆状物;(二)在1小时内缓慢加入甲醛水溶液,温度控制在50℃,并在1小时内缓慢升温至80℃,再在95℃反应3小时;(三)在热的反应体系加入氢氧化钠水溶液中和,先倾析分离掉水相,用热水洗涤有机相2次,真空脱除残留水分;(四)在热态的MOCA中添加含磷化合物及没食子酸酯复配的变色抑制剂,混合均匀,冷却造粒,包装。
盐酸与邻氯苯胺的摩尔比范围在1.5∶1。
甲醛与邻氯苯胺的摩尔比0.53∶1。
在反应混合物加入很少的变色抑制剂,可防止在分液、水洗等过程中高温产物的颜色变化,并且所加入的膦和亚磷酸酯化合物是非水溶性的,水洗过程损失较少,并且为了保持抗变色效果,由含磷化合物和没食子酸酯组成的复配变色抑制剂一般在MOCA造粒前添加。基于含苯环的磷酸酯几乎不溶于热水的原因,也可把膦或亚磷酸酯先添加到分层得到的有机相中,有利于延缓产物储存过程的变色。
以上所述者仅为用以解释本发明之较佳实施例,并非企图具以对本发明做任何形式上之限制,是以,凡有在相同之发明精神下所作有关本发明之任何修饰或变更,皆仍应包括在本发明意图保护之范畴。
Claims (6)
1.一种浅色聚氨酯固化剂的制备方法,其特征在于:由邻氯苯胺、甲醛在盐酸催化下进行缩合反应时加入羟胺类化合物,缩合反应得到浅黄色反应混合物,在90~105℃中和分液后,油相经水洗、除水后加入含磷化合物和没食子酸酯,冷却造粒后得到浅色且储存稳定的MOCA产品。
2.根据权利要求1所述的浅色聚氨酯固化剂的制备方法,其特征在于:所述羟胺类化合物为盐酸羟胺、羟胺、二甲基羟胺、二乙基羟胺、 二丙基羟胺、异丙基羟胺、二丁基羟胺、甲基乙基羟胺、N-异丙基羟胺、N,N-二烷基羟胺和N,N-二羟烷基羟胺中的至少一种;羟胺类化合物加入量为邻氯苯胺的质量的0.2%~1.0%。
3.根据权利要求1所述的浅色聚氨酯固化剂的制备方法,其特征在于:所述含磷化合物为膦化合物和亚磷酸酯中的至少一种;膦化合物为三苯基膦、三甲苯基膦、三丁基膦、三(对-甲基苯基)膦和三 (壬基苯基)膦中的至少一种;亚磷酸酯为亚磷酸三苯酯、亚磷酸三丁酯、亚磷酸三(壬基苯)酯、二亚磷酸二硬脂基季戊四醇酯、二亚磷酸季戊四醇二辛醇酯、亚磷酸三(2,4-二叔丁基苯基)酯、亚磷酸三(壬基苯)酯、四苯基二丙二醇二亚磷酸酯中的至少一种;含磷化合物用量为50~200ppm。
4.根据权利要求1所述的浅色聚氨酯固化剂的制备方法,其特征在于:没食子酸酯为没食子酸丙酯、没食子酸乙酯和没食子酸异戊酯中的至少一种,用量为10~100ppm。
5.根据权利要求4所述的浅色聚氨酯固化剂的制备方法,其特征在于:盐酸与邻氯苯胺的摩尔比为1.1~1.5∶1;甲醛与邻氯苯胺的摩尔比0.49~0.53∶1。
6.根据权利要求1所述的浅色聚氨酯固化剂的制备方法,其特征在于:在水、羟胺类化合物和盐酸组成的混合液中加入邻氯苯胺,然后加入甲醛溶液,温度控制在30~50℃,接着升温至75-85℃,再在80~95℃阶梯升温反应2~3小时,维持95~103℃加入氢氧化钠水溶液中和至pH值为8~9,静置待液体分层,倾析分离掉水相,有机相用95~100℃水洗涤,抽真空除去水分和残留邻氯苯胺,再加入含磷化合物和没食子酸酯,溶解均匀后冷却造粒。
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