MXPA00001781A - Process for making graft polyols using t-amyl peroxy free radical initiator - Google Patents
Process for making graft polyols using t-amyl peroxy free radical initiatorInfo
- Publication number
- MXPA00001781A MXPA00001781A MXPA/A/2000/001781A MXPA00001781A MXPA00001781A MX PA00001781 A MXPA00001781 A MX PA00001781A MX PA00001781 A MXPA00001781 A MX PA00001781A MX PA00001781 A MXPA00001781 A MX PA00001781A
- Authority
- MX
- Mexico
- Prior art keywords
- process according
- weight percent
- weight
- free radical
- polyol
- Prior art date
Links
- 229920005862 polyol Polymers 0.000 title claims abstract description 138
- 150000003077 polyols Chemical class 0.000 title claims abstract description 133
- -1 t-amyl peroxy Chemical group 0.000 title claims abstract description 95
- 239000003999 initiator Substances 0.000 title claims abstract description 44
- 238000000034 method Methods 0.000 title claims description 64
- 239000000203 mixture Substances 0.000 claims abstract description 48
- 239000000178 monomer Substances 0.000 claims abstract description 34
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- 230000000379 polymerizing Effects 0.000 claims abstract description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 51
- 239000006185 dispersion Substances 0.000 claims description 42
- 229920005903 polyol mixture Polymers 0.000 claims description 31
- NLHHRLWOUZZQLW-UHFFFAOYSA-N acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 27
- 229920000578 graft polymer Polymers 0.000 claims description 25
- 238000002360 preparation method Methods 0.000 claims description 25
- 229920000570 polyether Polymers 0.000 claims description 20
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 19
- OBETXYAYXDNJHR-UHFFFAOYSA-M 2-ethylhexanoate Chemical compound CCCCC(CC)C([O-])=O OBETXYAYXDNJHR-UHFFFAOYSA-M 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- 239000004815 dispersion polymerization Substances 0.000 claims description 7
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N fumaric acid Chemical class OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-L maleate(2-) Chemical compound [O-]C(=O)\C=C/C([O-])=O VZCYOOQTPOCHFL-UPHRSURJSA-L 0.000 claims description 3
- 125000000864 peroxy group Chemical group O(O*)* 0.000 claims description 3
- IMYCVFRTNVMHAD-UHFFFAOYSA-N 1,1-bis(2-methylbutan-2-ylperoxy)cyclohexane Chemical compound CCC(C)(C)OOC1(OOC(C)(C)CC)CCCCC1 IMYCVFRTNVMHAD-UHFFFAOYSA-N 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- KFAYHALUUVMGDE-UHFFFAOYSA-N pentyl 2-ethylhexanoate Chemical group CCCCCOC(=O)C(CC)CCCC KFAYHALUUVMGDE-UHFFFAOYSA-N 0.000 claims 2
- 229920001228 Polyisocyanate Polymers 0.000 abstract description 10
- 239000003795 chemical substances by application Substances 0.000 abstract description 10
- 239000005056 polyisocyanate Substances 0.000 abstract description 10
- 229920002635 polyurethane Polymers 0.000 abstract description 8
- 239000004814 polyurethane Substances 0.000 abstract description 8
- 150000003254 radicals Chemical class 0.000 description 33
- 125000002947 alkylene group Chemical group 0.000 description 24
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 12
- GOOHAUXETOMSMM-UHFFFAOYSA-N propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Substances OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 229920005830 Polyurethane Foam Polymers 0.000 description 9
- 229920000728 polyester Polymers 0.000 description 9
- 239000011496 polyurethane foam Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000006260 foam Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 230000002779 inactivation Effects 0.000 description 7
- WERYXYBDKMZEQL-UHFFFAOYSA-N 1,4-Butanediol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000000969 carrier Substances 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 150000002894 organic compounds Chemical class 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N (E)-but-2-enedioate;hydron Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N 2-Butanol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- 239000004604 Blowing Agent Substances 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N Maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 229960004063 Propylene glycol Drugs 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 150000008064 anhydrides Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium monoxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 4
- LKVLGPGMWVYUQI-UHFFFAOYSA-L calcium;naphthalene-2-carboxylate Chemical compound [Ca+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 LKVLGPGMWVYUQI-UHFFFAOYSA-L 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 239000003063 flame retardant Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 150000002334 glycols Chemical class 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 238000006317 isomerization reaction Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 230000002194 synthesizing Effects 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N 1,2-ethanediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N [N-]=C=O Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 150000003018 phosphorus compounds Chemical class 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- VMJIDDGLSSJEFK-UHFFFAOYSA-N 1,1,5-trimethyl-3,3-bis(2-methylbutan-2-ylperoxy)cyclohexane Chemical group CCC(C)(C)OOC1(OOC(C)(C)CC)CC(C)CC(C)(C)C1 VMJIDDGLSSJEFK-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N 1,6-Hexanediol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical group CCCCOOCCCC PAOHAQSLJSMLAT-UHFFFAOYSA-N 0.000 description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 1-ethenyl-4-methylbenzene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- JZDHUYKBYNFYAB-UHFFFAOYSA-N 2-(tert-butyldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(C)C JZDHUYKBYNFYAB-UHFFFAOYSA-N 0.000 description 2
- XYDCNXPXPVLOPD-UHFFFAOYSA-N 2-(tert-butyldiazenyl)-4-methoxy-2,4-dimethylpentanenitrile Chemical compound COC(C)(C)CC(C)(C#N)N=NC(C)(C)C XYDCNXPXPVLOPD-UHFFFAOYSA-N 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-Methyl-2-butene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- 231100000716 Acceptable daily intake Toxicity 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N Adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N Allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
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- 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
- YCIMNLLNPGFGHC-UHFFFAOYSA-N Catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
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- CZMRCDWAGMRECN-UGDNZRGBSA-N D-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 2
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- LVHBHZANLOWSRM-UHFFFAOYSA-N Itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical group CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
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- WQGWDDDVZFFDIG-UHFFFAOYSA-N Pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
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- 125000003277 amino group Chemical group 0.000 description 2
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- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
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- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
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- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 1
- PTLIZOFGXLGHSY-UHFFFAOYSA-N dibutylphosphane Chemical compound CCCCPCCCC PTLIZOFGXLGHSY-UHFFFAOYSA-N 0.000 description 1
- 229940042935 dichlorodifluoromethane Drugs 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- VZZJVOCVAZHETD-UHFFFAOYSA-N diethylphosphane Chemical compound CCPCC VZZJVOCVAZHETD-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 229960004419 dimethyl fumarate Drugs 0.000 description 1
- CGBYBGVMDAPUIH-ARJAWSKDSA-L dimethylmaleate(2-) Chemical compound [O-]C(=O)C(/C)=C(/C)C([O-])=O CGBYBGVMDAPUIH-ARJAWSKDSA-L 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- GXBYFVGCMPJVJX-UHFFFAOYSA-N epoxybutene Chemical compound C=CC1CO1 GXBYFVGCMPJVJX-UHFFFAOYSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N ethanolamine Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- NHOGGUYTANYCGQ-UHFFFAOYSA-N ethenoxybenzene Chemical compound C=COC1=CC=CC=C1 NHOGGUYTANYCGQ-UHFFFAOYSA-N 0.000 description 1
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 1
- AFIQVBFAKUPHOA-UHFFFAOYSA-N ethenyl 2-methoxyacetate Chemical compound COCC(=O)OC=C AFIQVBFAKUPHOA-UHFFFAOYSA-N 0.000 description 1
- FFYWKOUKJFCBAM-UHFFFAOYSA-N ethenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC=C FFYWKOUKJFCBAM-UHFFFAOYSA-N 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- GFJVXXWOPWLRNU-UHFFFAOYSA-N ethenyl formate Chemical compound C=COC=O GFJVXXWOPWLRNU-UHFFFAOYSA-N 0.000 description 1
- BLCTWBJQROOONQ-UHFFFAOYSA-N ethenyl prop-2-enoate Chemical compound C=COC(=O)C=C BLCTWBJQROOONQ-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- ZZUKBDJWZXVOQG-UHFFFAOYSA-N ethyl 2,2,2-tribromoacetate Chemical compound CCOC(=O)C(Br)(Br)Br ZZUKBDJWZXVOQG-UHFFFAOYSA-N 0.000 description 1
- SJMLNDPIJZBEKY-UHFFFAOYSA-N ethyl 2,2,2-trichloroacetate Chemical compound CCOC(=O)C(Cl)(Cl)Cl SJMLNDPIJZBEKY-UHFFFAOYSA-N 0.000 description 1
- NIJGVVHCUXNSLL-UHFFFAOYSA-N ethyl 2,2-dibromoacetate Chemical compound CCOC(=O)C(Br)Br NIJGVVHCUXNSLL-UHFFFAOYSA-N 0.000 description 1
- ZFGRMLYEKGWOAC-UHFFFAOYSA-N ethyl 2,3,4-trinitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C([N+]([O-])=O)=C1[N+]([O-])=O ZFGRMLYEKGWOAC-UHFFFAOYSA-N 0.000 description 1
- YBIALGDLTMTDFX-UHFFFAOYSA-N ethyl 4-ethylperoxycarbonylbenzoate Chemical group CCOOC(=O)C1=CC=C(C(=O)OCC)C=C1 YBIALGDLTMTDFX-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical group [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- XVOUMQNXTGKGMA-UHFFFAOYSA-N glutaconic acid Chemical compound OC(=O)CC=CC(O)=O XVOUMQNXTGKGMA-UHFFFAOYSA-N 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 1
- PBZROIMXDZTJDF-UHFFFAOYSA-N hepta-1,6-dien-4-one Chemical compound C=CCC(=O)CC=C PBZROIMXDZTJDF-UHFFFAOYSA-N 0.000 description 1
- SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 description 1
- VPIAKHNXCOTPAY-UHFFFAOYSA-N heptane-1-thiol Chemical compound CCCCCCCS VPIAKHNXCOTPAY-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- KETWBQOXTBGBBN-UHFFFAOYSA-N hex-1-enylbenzene Chemical compound CCCCC=CC1=CC=CC=C1 KETWBQOXTBGBBN-UHFFFAOYSA-N 0.000 description 1
- RYPKRALMXUUNKS-UHFFFAOYSA-N hex-2-ene Chemical compound CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 1
- 239000008079 hexane Substances 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N hexane-1,2,6-triol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- PMBXCGGQNSVESQ-UHFFFAOYSA-N hexane-1-thiol Chemical compound CCCCCCS PMBXCGGQNSVESQ-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical group OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 description 1
- 150000001261 hydroxy acids Chemical group 0.000 description 1
- 230000000977 initiatory Effects 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-M isobutyrate Chemical compound CC(C)C([O-])=O KQNPFQTWMSNSAP-UHFFFAOYSA-M 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- AMIMRNSIRUDHCM-UHFFFAOYSA-N isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- 239000011565 manganese chloride Substances 0.000 description 1
- 235000002867 manganese chloride Nutrition 0.000 description 1
- 229940099607 manganese chloride Drugs 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- NUMHUJZXKZKUBN-UHFFFAOYSA-N methyl 4-ethenylbenzoate Chemical compound COC(=O)C1=CC=C(C=C)C=C1 NUMHUJZXKZKUBN-UHFFFAOYSA-N 0.000 description 1
- OIGSXRLVIQGTAV-UHFFFAOYSA-N methyl ethenesulfonate Chemical compound COS(=O)(=O)C=C OIGSXRLVIQGTAV-UHFFFAOYSA-N 0.000 description 1
- 229940073769 methyl oleate Drugs 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- 229940113083 morpholine Drugs 0.000 description 1
- 101700000038 mpas Proteins 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N n-heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- XWJBRBSPAODJER-UHFFFAOYSA-N octa-1,7-diene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 1
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- JLIDVCMBCGBIEY-UHFFFAOYSA-N pent-1-en-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
- GLOBUAZSRIOKLN-UHFFFAOYSA-N pentane-1,4-diol Chemical compound CC(O)CCCO GLOBUAZSRIOKLN-UHFFFAOYSA-N 0.000 description 1
- GVSZYZPUKJBOJQ-UHFFFAOYSA-N pentyl 2-methylpropaneperoxoate Chemical group CCCCCOOC(=O)C(C)C GVSZYZPUKJBOJQ-UHFFFAOYSA-N 0.000 description 1
- XWYPMOYTTQTLRE-UHFFFAOYSA-N pentyl benzenecarboperoxoate Chemical group CCCCCOOC(=O)C1=CC=CC=C1 XWYPMOYTTQTLRE-UHFFFAOYSA-N 0.000 description 1
- SYOYTIYFEGZNHN-UHFFFAOYSA-N pentyl ethaneperoxoate Chemical group CCCCCOOC(C)=O SYOYTIYFEGZNHN-UHFFFAOYSA-N 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- ZUZSFMQBICMDEZ-UHFFFAOYSA-N prop-1-enylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CC=CC1=CC=CC=C1 ZUZSFMQBICMDEZ-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 description 1
- 239000007962 solid dispersion Substances 0.000 description 1
- 229940013123 stannous chloride Drugs 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static Effects 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- UATJOMSPNYCXIX-UHFFFAOYSA-N symmetric Trinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 UATJOMSPNYCXIX-UHFFFAOYSA-N 0.000 description 1
- GEKDEMKPCKTKEC-UHFFFAOYSA-N tetradecane-1-thiol Chemical compound CCCCCCCCCCCCCCS GEKDEMKPCKTKEC-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin dichloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
- CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- GBEZJXPZURJQOM-UHFFFAOYSA-N tris(1,2-dichloropropyl) phosphate Chemical compound CC(Cl)C(Cl)OP(=O)(OC(Cl)C(C)Cl)OC(Cl)C(C)Cl GBEZJXPZURJQOM-UHFFFAOYSA-N 0.000 description 1
- GTRSAMFYSUBAGN-UHFFFAOYSA-N tris(2-chloropropyl) phosphate Chemical compound CC(Cl)COP(=O)(OCC(C)Cl)OCC(C)Cl GTRSAMFYSUBAGN-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-M valerate Chemical compound CCCCC([O-])=O NQPDZGIKBAWPEJ-UHFFFAOYSA-M 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- LFOXXKXKYHIANI-UHFFFAOYSA-L zinc;7,7-dimethyloctanoate Chemical compound [Zn+2].CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O LFOXXKXKYHIANI-UHFFFAOYSA-L 0.000 description 1
- SXPUVBFQXJHYNS-UHFFFAOYSA-N α-Furil Chemical group C=1C=COC=1C(=O)C(=O)C1=CC=CO1 SXPUVBFQXJHYNS-UHFFFAOYSA-N 0.000 description 1
Abstract
The present invention relates to graft polyols employing a t-amyl peroxy compound as free radical initiator. The novel graft polyols are made by polymerizing at least one monomer in a polyol composition in the presence of a free radical initiator and preferably a chain transfer agent. The resulting graft polyols are in turn useful in reactions with polyisocyanates to make polyurethane products.
Description
"PROCESS FOR ELABORATING GRAIN POLYOLS USING A T-AMIL PEROXY FREE RADICAL INITIATOR"
FIELD OF THE INVENTION
The present invention relates to a process for making graft polyols that employ t-amyl peroxy components as a free radical initiator. These graft polyols are useful for the production of polyurethane foams. The present invention also relates to low viscosity graft polymer dispersions in polyoxyalkylene polyether polyols. More particularly, the invention relates to graft polymer dispersions prepared by a process employing free radical polymerization of an ethylenically unsaturated monomer or a mixture of monomers in a polyol mixture containing an effective amount of non-saturation induced, in where the polymerization is carried out in the presence of a free radical initiator comprising a t-amyl peroxy compound. This improved process yields stable, low viscosity, non-settable graft polymer dispersions.
BACKGROUND OF THE INVENTION The prior art, as demonstrated by US Patent Numbers 3,652,639; 3,875,258; 3,950,317 and the US Re-Expeditions of Patents Numbers 28,715; 29,014 and 33,291, discloses the preparation of graft polymer dispersions, which are useful in the preparation of polyurethanes, by the polymerization of ethylenically unsaturated monomers, in the presence of polyols. The aforementioned patents disclose various methods for preparing graft polymer dispersions. U.S. Patent No. 3,931,092 discloses the preparation of polymer solids, polymerizing in the presence of a free radical initiator and an organic solvent. The concentration of the solvent employed is from about 1 part to 19 parts by weight of the hydroxy-terminated organic compound, which has a double polymerizable carbon bond. U.S. Patent No. 3,953,393 discloses the preparation of graft copolymer dispersions using alkylmecaptan chain transfer agents at concentrations of 0.1 percent to 2 percent by weight, based on the weight of the vinyl monomer. Stable polymer dispersions have found wide commercial use in the preparation of polyurethanes. The use of these dispersions, known commercially as incarbon polyols or polymer, improves the process and, among other properties, the firmness of the polyurethane products, which are expressed
• Frequently as load carriers or module. There have been many attempts to improve products that represent the current state of the art. Efforts have been directed towards increasing the amount of polymer that is dispersed in the polyol, the obvious benefit being that stronger polymers can be produced. They have
• 10 encountered two main obstacles, the viscosities of the resulting dispersions were too high and / or the relatively high levels of acrylonitrile had to be used in the monomer mixtures employed. Furthermore, it would be desirable if the polyols of
Polymers could be prepared which exhibit better stability in terms of less agglomeration. Stability is important for the storage life of the polyols before they are used to make the polyurethane foams, since many
Polymer polyols tend to experience phase separation, if they do not stabilize. The relatively low viscosities and small particle sizes are also important than a good quality polyol to allow it to be easily pumped, in a producing equipment
high volume foam.
U.S. Patent No. 4,148,840 issued to Shah. and U.S. Patent No. 4,242,249 issued to Van Cleve, et al., describe the use of preformed polymer polyols as dispersion stabilizers in the synthesis of SAN dispersion polyols. The North American Patent Number 4, 148,840 describes preformed polymer polyol stabilizers having a viscosity of less than 40,000 cP at 25 ° C. However, these materials are viscous or semi-solid dispersions, which tend to be difficult to work with. U.S. Patent No. 4,172,825 issued to Shook and Golds relates to a process for producing polymer polyols having high polymer contents. The reference describes a process for making polymer polyols using a tertiary butyl peroxide as a free radical initiator. However, the resulting polymer polyols tend to have higher viscosities than those provided by the present invention. The North American Patents Numbers 4,327,005 and
4,334,049 issued to Ramlow et al. Disclose alkylene oxide adducts of styrene / allyl alcohol copolymers as preformed stabilizers for polymer polyols. The stabilizer may take the form of a graft copolymer dispersion or a finely divided solid polymer. In addition, Pizzini et al., In US Patent Number 3,652,639 discloses the use of acrylonitrile graft copolymers and an unsaturated polyol which are homogeneous clear liquids which can be used directly in the preparation of flexible polyurethane foams. The unsaturated polyol is obtained by reacting an organic compound having both non-ethylenic saturation and a hydroxyl, carboxyl or epoxy group with a polyol. A number of additional patents also disclose the use of encapsulated acryloyl unsaturated polyol copolymerized with styrene and acrylonitrile to produce polymer polyols. These patents include U.S. Patent Nos. 4,460,715; 4,477,603; 4,640,935; 4,513,124; 4,394,491 and 4,390,645. More recently, International Publication Number WO87 / 03886 and U.S. Patent No. 4,745,153 disclose the homo- or co-polymerization of vinyl-terminated polyol adducts alone or together with an ethylenically unsaturated monomer or monomer mixture in the presence of a compound containing active hydrogen as a solvent, and its use as preformed dispersants.
None of the related art, as far as is known, either alone or in combination, discloses or suggests that highly stable low viscosity graft polyols can be produced using free radical initiators based on tertiary amyl, particularly in association with the Semi-batch or continuous processes.
COMPENDIUM OF THE INVENTION
The present invention relates to a process for the preparation of graft polymer dispersions. The improved process employs free radical polymerization of at least one ethylenically unsaturated monomer in a polyol mixture containing an effective amount of preferably less than 0.1 mole per mole of the polyol mixture, no induced saturation, wherein the initiator of free radical comprises a tertiary amyl peroxy compound. In addition, it has been found that the improved dispersions can be prepared by employing radical polymerization in a polyether-polyole polyol mixture of polyoxyalkylene polyether containing less than 0.1 mol of non-saturation induced by mol of the polyol mixture, wherein the residue of non-saturation is polyether ester polyol containing isomerized maleate.
Preferably, the tertiary amyl peroxy compound employed is selected from the group consisting of tertiary amyl peroxy (2-ethylhexanoate); 1, 1-bis (tertiary amylperoxy) cydohexane; and mixtures thereof. In addition, the present invention relates to free radical initiators used for the production of graft polyols preferably formed using a continuous graft reactor and with a process for producing the graft polyols, wherein the viscosity properties do not vary greatly from sample in sample.
DETAILED DESCRIPTION OF A PREFERRED MODALITY OF THE
PRESENT INVENTION
In accordance with the improved process for the preparation of the stable graft polymer dispersions which are used for the preparation of polyurethane foams, the improvement comprises carrying out the polymerization of an ethylenically unsaturated monomer or mixtures of monomers in the presence of a effective amount of a free radical initiator, in a mixture of unsaturated polyol containing an effective amount of non-saturation induced, preferably less than 0.1 mol of non-saturation induced per mole of polyol mixture, wherein the free radical initiator comprises a tertiary amyl peroxy compound. In another embodiment of the invention the polymerization of an ethylenically unsaturated monomer or mixture of monomers in the presence of an effective amount of the free radical initiator in a polyol mixture containing non-saturation, which preferably contains less than 0.1 mole of non-saturation per mole of polyol mixture, employs an improved process comprising carrying out the polymerization in a polyol mixture employing as a part of the mixture a polyether polyol prepared by the reaction of a polyoxyalkylene polyether polyol with maleic anhydride and an alkylene oxide. This polyether ester polyol is isomerized by methods well known to those skilled in the art. These include heating, or isomerization catalysts such as morpholine, dibutylamine, diethylamine, diethanolamine, thiols and the like. Polyols that have no induced saturation are referred to below as "macromers". The chain transfer agents can be used as reaction moderators. The polymerization reaction can be carried out at temperatures between 25 degrees centigrade and 180 degrees centigrade, preferably between 80 degrees centigrade and 140 degrees centigrade. In one embodiment of the present invention, the polyol mixture contains less than about 0.1 mole, preferably from about 0.001 to about 0.09 mole, of non-saturation mole of polyol mixture. In general, the polyol mixture has an effective amount of induced saturation which will be defined herein as having from about 0.001 to about 0.2 mol of non-saturation induced by mol of the polyol mixture. The alkylene oxides which can be used for the preparation of the polyether ester polyols include ethylene oxide, propylene oxide, butylene oxide, amylene oxide and mixtures of these oxides. In general, the graft polymer dispersions of this invention have lower viscosities of
20,000 cP at 25 degrees centigrade, preferably viscosities ranging from 2000 to 15,000 cP at 25 degrees centigrade, and a solids content of about tf) 30 percent to about 70 percent, preferably about 40 percent a
about 60 percent, by weight based on the total weight of the polymer dispersion. Of course, as the solids content in the graft polymer dispersion increases, the viscosity of the dispersion will also increase.
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Among these chain transfer agents which may be employed are the following: acetic acid, bromoacetic acid, chloroacetic acid, ethyl dibromoacetate, iodoacetic acid, tribromoacetic acid, ethyl tribromoacetate, trichloroacetic acid, ethyl trichloroacetate, acetone, p-bromophenylacetonitrile, p-nophophenylacetylene, allyl alcohol, 2,4,6-trinitroaniline, p-ethynylanisol, 2,4,6-trinitroanisole, azobenzene, benzaldehyde, p-cyanobenzaldehyde, 2-butylbenzene, bromobenzene, 1,3,5-trinitrobenzene, benzocrisone, ethyl trinitrobenzoate, benzoin, benzonitrile, benzopyrene, tributylborane, 1,4-butanediol, 3,4-epoxy-2-methyl-1-butene, tertiary butyl ether, tertiary butyl isocyanide, 1-phenylbutyne, p cresol, p-bromoeumeno, dibenzonaphthacene, p-dioxane, pentaphenyl ethane, ethanol, 1,1-diphenylethylene, ethylene glycol, ethyl ether, fluorene, N, N-dimethylformamide, 2-heptene, 2-hexene, isobutyraldehyde, bromomalonate Diethyl bromotrichlor methane, dibromoethane, diiodomethane, naphthalene, 1-naphthol, 2-naphthol, methyl oleate, 2,4-triphenyl-1-pentene, 4-methyl-2-pentene, 2,6-diisopropylphenol, phenyl ether, phenylphosphine, diethylphosphine, dibutylphosphine, phosphorus trichloride, 1,1-tribromopropane, dialkyl phthalate, 1,2-propanediol, 3-phosphinopropionitrile, 1-propanol, pyrocatechol, pyrogallol, methyl stearate, -
tetraethylsilane, triethylsilane, dibromostilbene, alpha-bromostyrene, alpha-methylstyrene, tetraphenyl succinonitrile, 2,4,6-trinitrotoluene, p-toluidin, N, N-dimethyl-p-toluidine, alpha-cyano-p-tolunitrile, alpha, alpha'-dibromo-p-xylene, 2,6-xylenol, diethyl zinc, dithiodiacetic acid, ethyl dithiodiacetic acid, 4,4'-dithio-bisanthranilic acid, benzothiol, o-ethoxybenzthiol, 2,2'-dithiobisbenzothiazole, Benzyl sulfide, 1-dodecanethiol, ethanethiol, 1-hexanothiol, 1-naphthalethiol, 2-naphthalethiol, 1-octanotiol, 1-heptanothiol, 2-octanotiol, 1-tetradecanothiol, alpha-toluentiol, isopropanol, 2-butanol, tetrabromide carbon and tertiary dodecyl mercaptan. Preferred chain transfer agents are 2-propanol and 2-butanol. The chain transfer agents used will depend on the monomers or mixtures of specific monomers used and the molar ratios of these mixtures. The concentration of the chain transfer agent employed can vary from 0.1 percent to 30 percent by weight, preferably from 5 percent to 20 percent by weight, based on the weight of the monomer. Representative polyols substantially free of ethylenic unsaturation which can be used in combination with the macromers of the invention are well known to those skilled in the art.
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Frequently they are prepared by the catalytic condensation of an alkylene oxide or mixture of alkylene oxides either simultaneously or in sequence with an organic compound having at least two active hydrogen atoms such as is demonstrated by US Pat. Nos. 1,922,459; 3,190,927; and 3,346,557. Representative polyols include polyhydroxyl-containing polyesters, polyoxyalkylene polyether polyols, polyhydroxy-terminated polyurethane polymers, polyhydroxyl-containing phosphorus compounds and alkylene oxide adducts of the polyhydric polythioethers, polyacetals, aliphatic polyols and thiols, ammonia and amines including aromatic, aliphatic and heterocyclic, and mixtures thereof. The alkylene oxide adducts of the compounds containing 2 or more different groups within the classes defined above, for example, amino-alcohols containing an amino group and a hydroxyl group can also be used. Also, the alkylene oxide adducts of the compounds containing a group of SH and an OH group as well as those containing an amino group and a group of SH can be used. In general, the equivalent weight of the polyols will vary from 100 to 10,000, preferably from 1000 to 3000.
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Any suitable hydroxy-terminated polyester can be used such as those prepared for example from polycarboxylic acids and polyhydric alcohols. Any suitable polycarboxylic acid can be used such as oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, brasilic acid, tapsic acid, maleic acid, fumaric acid, glutaconic acid, alpha-hydromuconic acid, beta-hydromuconic acid, alpha-butyl-alpha-ethylglutaric acid, alpha-beta-diethyl-succinic acid, phthalic acid, terephthalic acid, hemimellitic acid and 1,4-cyclohexanedicarboxylic acid. Any suitable polyhydric alcohol, including both aliphatic and aromatic, can be used such as ethylene glycol, propylene glycol, trimethylene glycol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 1,2-pentanediol, 1,4- pentanediol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, glycerol, 1,1,1-trimethylolpropane, 1,1-trimethylolethane, 1,2,6-hexanetriol, alpha-methylglycoside, pentaerythritol and sorbitol. Included within the term "polyhydric alcohol" are phenol derivatives such as 2,2-bis (4-hydroxyphenyl) propane, commonly known as Bisphenol A.
The hydroxyl-containing polyester can also be a polyester amide such as is obtained by including a certain amount of amine or aminoalcohol in the reagents for the preparation of the polyesters. Therefore, the polyester amides can be obtained by condensing an amino-alcohol such as ethanolamine with the polycarboxylic acids noted above or can be made using the same components that constitute the hydroxyl-containing polyester with only a portion of the components being a diamine such as ethylenediamine. Any suitable polyoxyalkylene polyether polyol can be used such as a polymerization product of an alkylene oxide or a mixture of alkylene oxides with a polyhydric alcohol. Any suitable polyhydric alcohol can be used such as those disclosed above for use in the preparation of the finished hydroxy polyesters. Any alkylene oxide such ethylene oxide, propylene oxide, butylene oxide, amylene oxide and mixtures of these oxides can be used. The polyoxyalkylene polyether polyols can be prepared from other starting materials, such as tetrahydrofuran and mixtures of alkylene oxide-tetrahydrofuran; epihalohydrins such as epichlorohydrin; as well as aralkylene oxides such as styrene oxide. The polyoxyalkylene polyether polyols may have primary or secondary hydroxyl groups. Polyoxyethylene glycol, polyoxypropylene glycol, polyoxybutylene glycol, polytetramethylene glycol, block copolymers, for example, combinations of polyoxypropylene glycols and polyoxyethylene glycols, poly-1,2-oxybutylene and polyoxyethylene glycols, poly-1, 4-glycols, are included among the polyether polyols. oxybutylene and polyoxyethylene, and random copolymer glycols prepared from mixtures of two or more alkylene oxides or by the sequential addition of two or more alkylene oxides. The polyoxyalkylene polyether polyols can be prepared by any known process such as, for example, the process disclosed by Wurtz in 1859 and the Encyclopedia of Chemical Technology, Volume 7, pages 257-262, published by Interscience Publishers, Inc. (1951) or in the North American Patent Number 1,922,459. Preferred polyethers include the alkylene oxide addition products of trimethylolpropane, glycerin, pentaerythritol, sucrose, sorbitol, propylene glycol and 2,2 '- (4,4' -hydroxyphenyl) propane and mixtures thereof having equivalent weights from 100 to 5000. Suitable polyhydric polythioethers which can be condensed with alkylene oxides include the condensation product of thiodiglycol or the reaction product of a dicarboxylic acid as disclosed above for the preparation of polyesters containing hydroxyl with any other suitable thioether glycol. Polyhydroxyl-containing phosphorus compounds that can be used include those compounds disclosed in US Patent Number 3., 639,542. Preferred polyhydroxyl-containing phosphorus compounds are prepared from alkylene oxides and phosphorus acids having an equivalence of P2O5 from about 72 percent to about 95 percent. Suitable polyacetals which can be condensed with alkylene oxides include the reaction product of formaldehyde or other suitable aldehyde with a dihydric alcohol or an alkylene oxide such as those disclosed above. Suitable aliphatic thiols which can be condensed with alkylene oxides include alkanols which contain at least two SH groups such as 1,2-ethanedithiol, 1,2-propanedithiol, 1,3-propanedithiol, and 1,6-hexanediol; alkene thiols such as 2-butene-1, 4-dithiol; and alkyne thiols such as 3-hexyn-l, 6-dithiol.
Suitable amines which can be condensed with alkylene oxides include the aromatic amines such as aniline, o-chloroaniline, p-aminoaniline, 1,5-diaminonaphthalene, methylene dianiline, the condensation products of aniline and formaldehyde, and 2,3- , 2,6-, 3,4-, 2,5- and 2,4-diaminotoluene; aliphatic amines such as methylamine, triisopropanolamine, ethylenediamine, 1,3-diaminopropane, 1,3-diaminobutane and 1,4-diaminobutane. Also, polyols containing ester groups can be used in the present invention. These polyols are prepared by the reaction of an alkylene oxide with an organic dicarboxylic acid anhydride and a compound containing reactive hydrogen atoms. A more comprehensive discussion of these polyols and their method of preparation can be found in U.S. Patent Nos. 3,585,185; 3,639,541 and 3,639,542. The unsaturated polyols or macromers which are employed in the present invention can be prepared by the reaction of any conventional polyol such as those described above with an organic compound having both non-ethylenic saturation and a hydroxyl, carboxyl, anhydride group , isocyanate or epoxy, or other group reactive with an active hydrogen-containing group, or can be prepared using an organic compound having both non-ethylenic saturation and a hydroxyl, carboxyl, anhydride or epoxy group, or other group reactive group containing active hydrogen as a reagent in the preparation of the conventional polyol. Representative of these organic compounds include unsaturated mono- and poly-carboxylic acids and anhydrides such as maleic acid and fumaric acid anhydride, crotonic acid and anhydride, propenyl, succinic anhydride, acrylic acid, acryloyl chloride, hydroxyethyl methacrylate or acrylate and hydrogenated maleic acids and anhydrides, unsaturated polyhydric alcohols such as 2-butene-1,4-diol, glyceroalyl ether, trimethylolpropanoalyl ether, pentaerythritol allyl ether, pentaerythritol vinyl ether, pentaerythritol butyl ether, and 1-butene-3 , -diol, unsaturated epoxides such as l-vinylcyclohexene-3, 4-epoxide, butadiene monoxide, vinylglycidyl ether (1-vinyloxy-2,3-epoxypropane), glycidyl methacrylate and 3-allyloxypropylene oxide ( allylglycidyl). If a polycarboxylic acid or anhydride is used to incorporate non-saturation in the polyols, it is preferred to react the unsaturated polyol with an alkylene oxide, preferably ethylene or propylene oxide, to replace the carboxyl groups with hydroxyl groups before to be employed in the present invention. The amount of alkylene oxide employed is such as to reduce the acid number of the unsaturated polyol to about 5 or less. In one embodiment of the present invention, the malemonated macromers are isomerized at temperatures ranging from 80 degrees centigrade to 120 degrees centigrade for half an hour to three hours in the presence of an effective amount of an isomerization catalyst, which are well known to those persons experts in technique The catalyst is generally employed at concentrations greater than 0.01 weight percent based on the weight of the macromer. When the polyether ester polyol is prepared using the catalyst selected from the group consisting of salts and oxides of the divalent metals, the concentration of the catalyst that can be used ranges from 0.005 percent to 0.5 percent by weight based on the weight of the polyol mixture. The temperatures used range from 75 degrees Celsius to 175 degrees Celsius. The equivalent weight of the polyol used to make the macromer can vary from 1000 to 10,000, preferably from 2000 to 6000. Among the divalent metals that can be employed are zinc acetate, zinc chloride, zinc oxide, zinc neodecanoate, tin chloride, calcium naphthenate, calcium chloride, calcium oxide, calcium acetate, copper naphthenate, cadmium acetate, cadmium chloride, nickel chloride, manganese chloride and manganese acetate. Certain of the catalysts mentioned above such as calcium naphthenate promote or activate the isomerization of the maleate in the fumarate structure during the preparation of the macromer, while others such as zinc chloride, which is an effective catalyst for polymerization, inhibit this isomerization. As mentioned above, the graft polymer dispersions of the invention are prepared by in situ polymerization, in the polyols described above, of an ethylenically unsaturated monomer or a mixture of ethylenically unsaturated monomers. Representative ethylenically unsaturated monomers that can be employed in the present invention include butadiene, isoprene, 1,4-pentadiene, 1,6-hexadiene, 1,7-octadiene, styrene, alpha-methylstyrene, 2-methylstyrene, 3-methylstyrene and 4-methylstyrene, 2,4 dimethylstyrene, ethylstryrene, isopropylstyrene, butylstyrene, phenylstyrene, cyclopentylstyrene, benzylstyrene and the like; substituted styrenes such as cyanostyrene, nitrostyrene, N, N-dimethylaminostyrene, acetoxystyrene, methyl 4-vinylbenzoate, phenoxystyrene, p-vinylphenyl oxide, and the like; the substituted acrylic and acrylic monomers such as acrylonitrile, acrylic acid, methacrylic acid, methyl acrylate, 2-hydroxyethyl acrylate, methyl methacrylate, cyclohexyl methacrylate, benzyl methacrylate, isopropyl methacrylate, octyl methacrylate, methacrylonitrile, alpha-ethoxyacrylate, ethyl, methylaliphathacrylaminoacrylate, butyl acrylate, 2-ethylhexyl acrylate, phenyl acrylate, phenylmethacrylate, N, N-dimethylacrylamide, N, N-dibenzylacrylamide, N-butylacrylamide, methacrylyl formamide, and the like; vinyl esters, vinyl ethers, vinyl ketones, etc., such as vinyl acetate, vinyl butyrate, isopropenyl acetate, vinyl formate, vinyl acrylate, vinyl methacrylate, vinylmethoxyacetate, vinyl benzoate, vinyltoluene, vinylnaphthalene, vinylmethyl ether, vinylethyl ether, vinylpropyl ethers, vinylbutyl ethers, vinyl 2-ethylhexyl ether, vinylphenyl ether, vinyl 2-methoxyethyl ether, methoxybutadiene, vinyl 2-butoxyethyl ether, 3,4-dihydro-1, 2-pyran, 2-butoxy-2-vinyl-oxydiethyl ether, vinylmethyl ketone, vinylethyl ketone, vinyl phosphonates such as vinylphenyl ketone, vinylethyl sulphone, N-methyl-N-vinyl acetamide, N-vinylpyrrolidone, vinyl imidazole, divinyl sulfoxide, divinyl sulfone, sodium vinyl sulfonate, methyl vinyl sulfonate, N-vinyl pyrrole and the like; dimethyl fumarate, dimethyl maleate, maleic acid, crotonic acid, fumaric acid, itaconic acid, monomethyl itaconate, t-butylaminoethyl methacrylate, dimethylaminoethyl methacrylate, glycidyl acrylate, allyl alcohol, glycol monoesters of itaconic acid, pyridine vinyl and similar. Any of the known polymerizable monomers can be used and the compounds mentioned above are illustrative and not restrictive of monomers suitable for use in this invention. Preferably, the monomer is selected from the group consisting of acrylonitrile, styrene and mixtures thereof. The amount of the ethylenically unsaturated monomer employed in the polymerization reaction is generally from 25 percent to 70 percent, preferably from 40 percent to 60 percent, based on the total weight of the product. The polymerization occurs at a temperature between about 25 degrees Celsius and 180 degrees Celsius, preferably from 80 degrees Celsius to 140 degrees Celsius. It is preferred that at least 25 percent to 90 percent by weight, more preferably between about 40 percent and 75 percent by weight of the monomer employed is styrene or 4-methylstyrene. Generally, in the process of the present invention, from about 0.1 weight percent to about 3.0 weight percent, preferably from about 0.3 weight percent to about 1.0 weight percent, of the free radical initiator will be employed. based on the total weight of the monomers used. In the process of the present invention, the free radical initiator comprises a tertiary amyl peroxy compound. Suitable tertiary amyl peroxy compounds include tertiary amyl peroxydecanoate; tertiary amylperoxypivalate, tertiary amyl peroxy ethylhexanoate; 1,1 di (t-amylperoxy) 3,3,5-trimethylcyclohexane; 2.2 [4.4 di (t-amylperoxycyclohexyl) propane]; 1,1 di (t-amylperoxy) cydohexane; t amylperoxy 2 methylbenzoate; 1,1 di (t-amylperoxy) 3,5,5-trimethylcyclohexane; 2,2 di (t-amylperoxy) butane; di t amyldiperoxyazelate; tertiary amyl peroxy isopropyl carbonate; tertiary amyl peroxybenzoate; tertiary amyl peroxyacetate; n-butyl 4,4 di (tertiary peroxyamyl) valerate; diperoxyptalate di and t amyl; di (2-tertiary amyloisopropyl) benzene; 2,5-dimethyl-25 di (tertiary amyl peroxy) hexane; 1,4 di (2-tertiary amyloisopropyl) benzene; tertiary amyl cu lyl peroxide; tertiary amyl peroxide; tertiary amyl hydroperoxide; tertiary amyl peroxydiethyl acetate; tertiary amyl peroxyisobutyrate; tertiary butyl peroxy carbonate 2-ethylhexyl; tertiary amyl peroxy stearyl carbonate; tertiary amyl peroxy (2-ethylhexanoate); and 1,1 bis (tertiary amyl peroxy) cydohexane. These tertiary amyl peroxy compounds can be used either alone or in combination with one another. In a preferred embodiment of the present invention, the free radical initiator is selected from the group consisting of tertiary amyl peroxy (2-ethylhexanoate); 1, 1 bis (tertiary amylperoxy) cydohexane; and mixtures thereof. More preferably, the composition of the free radical initiator of the present invention will include a certain amount of both tertiary amyl peroxy (2-ethylhexanoate) and 1,1-bis (tertiary amyl peroxy) cydohexane peroxy. When used in combination with one another, the weight ratio of tertiary amyl peroxy (2-ethylhexanoate) to 1,1-bis (tertiary amyl peroxy) cyclohexane will generally be in the order of about 1:10 to about 1: 2. , more preferably from about 1: 4 to about 1: 3. To the limited extent that other free radical initiators are used in combination with the tertiary amyl peroxy compounds described above in the process of the present invention, the additional free radical initiators that can be employed are two types of radical free well known vinyl polymerization initiators such as peroxides, persulfates, perborates, percarbonates, azo compounds, etc. These include hydrogen peroxide, dibenzoyl peroxide, acetyl peroxide, benzoyl hydroperoxide, tertiary butyl hydroperoxide, tertiary butyl peroxide, lauroyl peroxide, butyryl peroxide, diisopropylbenzene hydroperoxide, eumenohydroperoxide, paramentane hydroperoxide, peroxide. of diacetyl, di-alpha-cumyl peroxide, dipropyl peroxide, diisopropyl peroxide, isopropyl-t-butyl peroxide, butyl-t-butyl peroxide, difuroyl peroxide, bis (triphenylmethyl) peroxide, bis (p-methoxybenzoyl) peroxide, p-monomethoxybenzoyl peroxide , Ruben Peroxide, Ascaridol, Tertiary Butyl Peroxybenzoate, Diethyl Peroxyterephthalate, Propyl Hydroperoxide, Isopropyl Hydroperoxide, N-Butyl Hydroperoxide, Tertiary Butyl Hydroperoxide, Cyclohexyl Hydroperoxide, Trans Decalin Hydroperoxide, Alpha Methylbenzyl Hydroperoxide, Hydroperoxide alpha methyl ethyl ethylbenzyl, hydroperoxide d tetralin, triphenylmethyl hydroperoxide, diphenylmethyl hydroperoxide, alpha, alpha'-azobis (2-methylheptonitrile), 1,1'-azobis
(cyclohexanecarbonitrile), 4,4'-azobis (4-cyanopentanoic acid), 2,2'-azobis (isobutyronitrile), 1-t-butylazo-1-cyanocyclohexane, persuccinic acid, diisopropyl peroxy-dicarbonate, 2,2'-azobis (2,4-dimethylvaleronitrile) , 2-t-butylazo-2-cyano-4-methoxy-4-methylpentane, 2,2-azobis-2-methylbutanonitrile, 2-t-butylazo-2-cyanobutane, 1-t-amylazo-1-cyanocyclopropane, 2,2'-azobis (2,4-dimethyl-4-methoxivaleronitrile, 2,2'-azobis 2-methylbutyronitrile, 2-t-butylazo-2-cyano-4-methylpentane, 2-t-butylazo-2-isobutyronitrile, to butylperoxyisopropyl carbonate and the like, a mixture of initiators can also be used.
2,2'-azobis (2-methylbutyronitrile), 2,2'-azobis
(isobutyronitrile), 2,2'-azobis (2,4-dimethylvaleronitrile), 2-t-butylazo-2-cyano-4-methoxy-4-methylpentane; 2-t-butylazole-2-cyano-4-methylpentane, 2-t-butylazo-2-cyanobutane and lauroyl peroxide. General descriptions of graft polymer dispersions and processes for preparing graft polymer dispersions are set forth in Reissues of US Patent Nos. 33,291; 4,690,956; 4,689,354; 4,458,038; 4.4550.194; and 4,661,531; the exhibitions of which are incorporated into
• the present by reference. The polyurethane foams employed in the present invention are generally prepared by reacting a graft polymer dispersion with an organic polyisocyanate in the presence of a blowing agent and optionally in the presence of components that
contain additional polyhydroxyl, extension agents
• chain, catalysts, surfactants, stabilizers, colorants, fillers or fillers and pigments. Appropriate processes for the preparation of cellular polyurethane plastics are disclosed in
Reissue of US Patent Number 24,514, the disclosure of which is incorporated herein by reference, along with the appropriate machinery to be used in conjunction therewith. When water is added as the blowing agent, corresponding amounts of water can be used.
excess isocyanate to react with water and produce carbon dioxide. It is possible to continue with the preparation of the polyurethane plastics by means of a prepolymer technique in which an excess of the organic polyisocyanate is reacted in a first step in the polyol of
The present invention for preparing a prepolymer having free isocyanate groups which is then reacted in a second step with sour and / or additional polyol to prepare a foam. Alternatively, the components that can be reacted in a single working step commonly known as the "one operation" technique of preparing the polyurethanes. Also instead of agtua, low boiling point hydrocarbon blowing agents such as pentane, hexane, heptane, pentene and heptene can be used as blowing agents; azo compounds such as azohexahydrobenzodinitrile; halogenated hydrocarbons such as dichlorodifluoromethane, trichlorofluoromethane, dichlorodifluoroethane, vinylidene chloride, and methylene chloride. The organic polyisocyanates that may be employed include aliphatic and cycloaliphatic aromatic polyisocyanates and combinations thereof. Representative of these types are diisocyanates such as m-phenylene diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 2,4- and 2,6-toluene diisocyanate mixtures, hexamethylene diisocyanate, tetramethylene diisocyanate, cyclohexane. 1,4-diisocyanate, hexahydrotoluene diisocyanate (and isomers), naphthalene-1,5-diisocyanate, 1-methoxyphenyl-2,4-diisocyanate, 4,4'-diphenylmethane-diisocyanate, 4,4'-biphenylene-diisocyanate, 3,3'-dimethoxy-4-diisocyanate , 4 'biphenyl, 3,3' dimethyl 4,4 'biphenyl diisocyanate and 3,3' dimethyldiphenylmethane 4,4 'diisocyanate; triisocyanates such as 4,4 ', 4", 4" triphenylmethane triisocyanate, and 2,4,6 toluene triisocyanate; and tetraisocyanates such as 4,4'-dimethyldiphenylmethane 2,2'5,5'-tetraisocyanate and polymeric polyisocyanates such as polymethylene polyphenylene polyisocyanate. Especially useful due to their availability and properties are toluene diisocyanate, 4,4'-diphenylmethane diisocyanate and polymethylene polyphenylene polyisocyanate. The crude polyisocyanates that can also be used in the compositions of the present invention such as crude toluene isocyanate obtained by the phosgenation of a mixture of diamines of toluene or crude diphenylmethane isocyanate obtained by the phosgenation of crude diphenylmethane diamine. Preferred or crude isocyanates are disclosed in U.S. Patent No. 3,215,652. As mentioned above, the graft polyols can be used in conjunction with another polyhydroxy containing component commonly employed in the art. Any of the polyhydroxyl-containing components that are described above for use in the preparation of the graft polyols can be used in the preparation of polyurethane foams useful in the present invention. Chain extension agents that can be employed in the preparation of polyurethane foams include those compounds having at least two functional groups that carry active hydrogen atoms such as water, hydrazine, primary and secondary diamines, amino-alcohols, amino acids , hydroxy acids, glycols or mixtures thereof. A preferred group of chain extension agents includes water, ethylene glycol, 1,4-butanediol primary and secondary diamines which react more readily with the prepolymer than water such as phenylene diamine, 1,4-cyclohexane-bis- (methylamine ), ethylenediamine, diethylenetriamine, N- (2-hydroxypropyl) ethylenediamine, N, N'-di (2-hydroxypropyl) ethylenediamine, piperazine, and 2-methylpiperazine. Any suitable catalyst can be used including tertiary amines such as, for example, triethylenediamine, N-methylmorpholine, N-ethylmorpholine, diethylethanolamine, N-co-morpholine, l-methyl-4-dimethylaminoethylpiperazine, 3-methoxypropimidimethylamine, N, N, N '- trimethyl isopropyl-propylenediamine, 3-diethylaminopropyldiethylamine, dimethylbenzylamine, and the like. Other suitable catalysts are, for example, stannous chloride, dibutyltin di-2-ethylhexanoate, stannous oxide, as well as other organometallic compounds such as those disclosed in U.S. Patent No. 2,846,408. A surfactant is generally necessary for the production of high quality polyurethane foam according to the present invention, since in the absence thereof, the foams are squashed or contain very large unequal cells. Numerous surfactants have been found satisfactory. Nonionic surfactants are preferred. Of these, nonionic surfactants such as well-known silicones have been found particularly desirable. Other surfactants that are able to function even when they are not preferred include polyethylene glycol ethers of long chain alcohols, tertiary amine or alkanolamine salts of the long chain alkyl acid sulfate esters, alkyl sulfonic esters and arylsulfonic acids of I rent. It has been found that when the graft polymer dispersions of the present invention are used in the preparation of polyurethane foam products, a flame retardant compound is preferably incorporated in the foam product to impart flame retardancy. Among the flame retardants that can be used are: pentabromodiphenyl oxide, dibromopropanol, tris (beta-chloropropyl) phosphate, 2,2-bis (bromoethyl) -1, 3-propanediol, tetrakis (2-chloroethyl) ethylene diphosphate, tris ( 2, 3-dibromopropyl) phosphate, tris (beta-chloroethyl) phosphate, tris (1,2-dichloropropyl) phosphate, bis (2-chloroethyl) -2-chloroethylphosphonate, molybdenum trioxide, ammonium molybdate, ammonium phosphate, pentabromodiphenyl oxide, tricresyl phosphate, hexabromocyclododecane and dibromoethyl dibromocyclohexane. The concentrations of the flame retardant compounds that can be used vary from 5 parts to 25 parts per 100 parts of the polyol mixture. The following examples illustrate the nature of the invention and should not be construed as limiting the invention. Unless otherwise indicated, all parts are provided as parts by weight.
EXAMPLES
Polyol At a 30 percent dispersion (1: 1 acrylonitrile / styrene) in Polyol C using 2,2'-azobis (2-methylbutanonitrile).
Polyol B is a propylene oxide initiated with trimethylolpropane, an adduct of ethylene oxide containing an inactivation of ethylene oxide and having a hydroxyl number of 25.
Polyol C is a propylene oxide initiated with trimethylolpropane, an adduct of ethylene oxide containing an inactivation of ethylene oxide and having a hydroxyl number of 35. Polyol D is a 50 percent dispersion (1: 1 acrylonitrile / styrene) in Polyol C using 2, 2'-azobis (2-methylbutanonitrile). Polyol E is a 50 percent dispersion (1: 2 acrylonitrile / styrene) in Polyol C using USP 90 PX. Polyol G is a 45 percent dispersion (1: 2 acrylonitrile / styrene) in Polyol C using USP 90 PX. Polyol H is a propylene oxide starting with glycerin, an adduct of ethylene oxide containing 12.5 weight percent ethylene oxide (hexeric) and an inactivation of propylene oxide, and having a hydroxyl number of 51. Polyol J is a 43 percent dispersion (1: 2 acrylonitrile / styrene) in Polyol H using 2,2'-azobis (2-methylbutanonitrile).
Polyol K is a 50 percent dispersion (1: 2 acrylonitrile / styrene) in Polyol H using USP 90 PX. Polyol L is a 50 percent dispersion (1: 2 acrylonitrile / styrene) in Polyol H using 2,2'-azobis (2-methylbutane-nitrile) and USP 90 PX. Polyol M is a 50 percent dispersion (1: 2 acrylonitrile / styrene) in Polyol H using 2, 2'-azobis (2-methylbutanonitrile) and USP 90 PX. Polyol N is a 50 percent dispersion (1: 1 acrylonitrile / styrene) in Polyol H using 2,2'-azobis (2-methylbutanenitrile) and USP 90 PX. Polyol O is a 50 percent dispersion (1: 1 acrylonitrile / styrene) in Polyol H using 2, 2 'azobis (2-methylbutane).
Polyol P is an adduct of propylene oxide initiated with propylene glycol having a hydroxyl number of 145. Polyol Q is a 60 percent dispersion (45:55 acrylonitrile / styrene) in Polyol P using 2,2'-azobis ( 2-methylbutanonitrile) and USP 90 PX. Polyol R is a 60 percent dispersion (45:55 acrylonitrile / styrene) in Polyol P using 2,2'-azobis (2-methylbutanonitrile) and USP 90 PX. Polyol S is a 60 percent dispersion (45:55 acrylonitrile / styrene) in Polyol P using 2, 2 '-azobis (2-methylbutanonitrile) and USP 90 PX Polyol T is a 60 percent dispersion (45: 55 of acrylonitrile / styrene) in Polyol P using 2, 2'-azobis (2-methylbutanonitrile) and USP 90 PX. Polyol X is a 43 percent dispersion (1: 2 acrylonitrile / styrene) in Polyol H using VAZO 67. Polyol W is a 50 percent dispersion (1: 2 acrylonitrile / styrene) in Polyol H using USP 90 PX. VAZO 67 is a polymerization initiator of 2,2'-azobis (2-methylbutanonitrile) which can be obtained commercially from E.l. DuPont Co. USP 90 PX is 1,1'-bis (t-amylperoxy) cyclohexane, 80 percent solution in 2, 2 ', 4-trimethyl-1,3-pentane diol isobutyrate obtainable from Witco Corporation. LUPERSOL 575 is a tertiary amyl peroxy (2-ethylhexanoate) that can be obtained from Lucidol, Inc. DC-5043 is a silicone surfactant available from Dow Corning Corporation,
DEOA-LF is diethanolamine with 15 percent water obtainable from Union Carbide Corporation,
Dabco 33 LV is a 33 percent solution of trietherotriamine in dipropylene glycol obtainable from Air Products Corporation, Niax Al is an amine catalyst made by Union Carbide Corp. T-12 is an organotin catalyst made by Air Products Corp. AB 100 is a chlorinated phosphate ester flame retardant which can be obtained commercially from Albright & Wilson, Inc. Macromer A is a polyether polyol containing fumarate ester made by reacting an inactivated trimethylolpropane / propylene oxide adduct with 4.8 percent ethylene oxide and a hydroxyl number of 25., with maleic anhydride in the presence of a calcium naphthenate catalyst and inactivation with propylene oxide. A representative procedure for the synthesis is described in US Pat. Number 33,291, Reissue 11, Process A. Macromer B is a polyether polyol containing fumarate ester made by reacting a glycerin / propylene oxide adduct with 25 per cent. one hundred percent of an ethylene oxide structure, 20 percent present as a heteretic, 5 percent as an inactivation, and a hydroxyl number of 25, with maleic anhydride in the presence of a calcium naphthenate catalyst and inactivation with calcium oxide. propylene. A representative procedure for the synthesis is described in US Reissue Issue Number 33,291, column 11, method A. Macromer C is an adduct of 1- (1-isocyanato-1-methylethyl) -3- (1-methylethhenyl) benzene containing polyether polyol made by reacting an adduct of sucrose / propylene oxide of polyether polyol initiated with dipropylene glycol with 5 percent inactivation of ethylene oxide, and a hydroxyl number of 25. A representative procedure for the synthesis is described in U.S. Patent No. 5,093,412. A throughput reactor of 300 milliliter capacity is used to make the graft polyols of the present invention in a continuous base under pressure. The reactor is operated in a complete manner, that is, there is no upper space. Initially, it contains a polyol or graft polyol. In the initiation phase, the material pumped through the reactor is discarded until the desired product is being produced. The reaction mixture consisting of polyol, macromer, monomers, reaction moderator and the free radical initiator enters the reactor from the bottom, is mixed with the material that is already in the reactor at the top through a valve loaded with spring. The pressure in the reactor is maintained from 4.22 to 8.44 kilograms per square centimeter at a reaction temperature of 140 ° C to 160 ° C. After the crude product leaves the reactor, it is no longer under pressure. It is collected and purified in a glass pressure flask from <; 0.1 millimeter of Hg for a minimum of 30 minutes to remove volatile materials such as unreacted monomers. The finished product is stabilized by the addition of antioxidants, cooled and stored in an appropriate container.
Once the desired graft polyols are achieved, several foam samples are prepared as disclosed in Tables 1 to 4 by introducing a polyisocyanate composition at the desired index to the graft polyol composition with certain physical properties such as density, tensile strength, elongation and breaking strength having been analyzed. As shown in Tables 1 to 4, which are presented below, graft polyols employing tertiary amyl peroxy compounds as a free radical initiator in accordance with the teachings of the present invention have lower viscosities and stability of significantly better dispersion when compared to the graft polyols prepared using the tertiary butyl peroxy compounds as the free radical initiator.
-
TABLE 1
1. 8 pounds per cubic foot density foam at 20 percent solids level of the graft polymer
Foam number
Pbw components
Polyol A 65 65
Polyol B 35 35 35 35 35 35 35
Polyol C 25 25 25 25 25
Polyol D 40 40
Poliol E 40 40
Polyol G 40
DC-5043 0.8 0.8 0.8 0.8 0.8
DEOA-LF 1.6 1.6 1.6 1.6 1.6 1.6 1.6
DABCO 33LV 0.12 0.12 0.12 0.12
NIAX A-l 0.04 0.04 0.04 0.04 0.04 0.04 0.0 '
T-12 0.06 0.06 0.06 0.06 0.06 0.06 0.6
AB-100 4.0 4.0 4.0 4.0 4.0 4.0 4.0 Water 3.0 3.0 3.0 3.0 3.0 3.0 3.0
TDI 40.51 40.51 40.51 40.51 40.51 40.51 40.51
TDI index 105 105 105 105 105 105 105
% solids of the graft polymer 20 20 20 20 20 20 20
Properties of the foam:
Density, per cubic foot 1.82 1.76 1.74 1.86 1.75 1.68 1.65
Voltage, Kg / cm2 1.55 1.34 1.48 1.69 1.97 1.34 1.69
Wet aged tension, Kg / cm.2 1.48 1.12 1.55 1.48 1.90 1.55 1.76
Elongation,% 152 127 138 161 146 111 14?
Break, kilograms / centimeter 3.34 2.07 3.68 3.22 3.91 2.76 3.68
TABLE 2
Graft Poly A D G
Ingredients:
Polyol carrier: Polyol C 67 42.39 47.36 47.36
acrylonitrile 15.5 15.94 14.64 14.64
styrene 15.5 31.87 29.27 29.27
type of macromer: A B B B
amount of the macromer 1.24 2.15 1.9? 1.9?
moderator type dodeca- 2- 2- 2-reaction notiol propanol propanol propanol
amount of reaction moderator 0.31 7.17 6.58 6.58
VAZO 67 (free radical initiator) 0.31 0.48 0.09
USP 90 PX (free radical initiator) 0.18 0.09 TABLE 3
Graft Polyol J K L
Ingredients :
Polyol carrier: Polyol H 54. 71 41. 96 41. 96
acrylonitrile 14.33 15.94 15.94
styrene 28.67 31.87 31.87
type of macromer: A A A
number of macromer 1.61 2.87 2.87
type of moderator dodeca- 2- 2-reaction notiol propanol propanol
amount of reaction moderator 0.43 7.17 7.17
VAZO 67 (free radical initiator) 0.25 0.05
USP 90 PX (free radical initiator) 0.19 0.14 TABLE 3 (Continued)
Graft Polyol M N 0
Ingredients :
Polyol carrier: Polyol H 41. 96 41. 96 41. 68
acrylonitrile 15.94 15.94 15.94
styrene 31.87 31.87 31.87
type of macromer: A A A
amount of macromer 2.87 2.87 2.87
type of moderator 2- 2- 2-propanol propanol propanol reaction
amount of reaction moderator 7.17 7.17 7.17
VAZO 67 (free radical initiator) 0.095 0.04 1.48
USP 90 PX (free radical initiator) 0.095 0.15 TABLE 4
Designation of Graft Polyol Q R
Ingredients
Polyol carrier: Polyol P 31.45 31.45 31.45
acrylonitrile 25.34 25.34 25.34
styrene 30.97 30.97 30.97
type of macromer: B B B
amount of macromer 3.3? 3.3? 3.3?
type of moderator 2- 2- 2-propanol propanol propanol reaction
amount of reaction moderator 8.45 8.45 8.45
VAZO 67 (free radical initiator) 0.17 0.17
USP 90 PX (free radical initiator) 0.25 0.25 0.42 TABLE 4 (Continued)
Designation Polyol of Graft W X
Ingredients :
Polyol carrier: Polyol P 31.11 41.94 46.93
acrylonitrile 25.34 15.94 22.35
styrene 30.97 31.87 27.35
type of macromer: B A C
number of macromer 3.38 2.87 2.48
type of moderator 2- 2- 2-propanol propanol butanol / water reaction
amount of reaction moderator 8.45 7.17 9.92 / 0.58
VAZO 67 (free radical initiator) 0.34 0.33
USP 90 PX (free radical initiator) 0.42 0.24 The graft polymer dispersions according to the present invention can also be prepared in a semi-batch reactor. A suitable reactor is provided and subjected to the following procedure. The reagents and levels of them are disclosed in Table 5, which is presented below. After loading the one-liter capacity four-necked RB flask, the reaction mixture is heated to the reaction temperature. The monomer and the polyol mixture are added through a Kenics static mixer for the specified time. After the reaction period the mixture is vacuum stripped for 30 minutes to about 1 millimeter of mercury. The reaction temperature is 125 ° C, the monomer addition time is 210 minutes, the polyol / LUPERSOL 575 addition time is 220 minutes; the reaction time is 30 minutes; and the stirring is carried out at 300 revolutions per minute. As shown in Table 5, which is presented below, graft polyols employing tertiary amyl peroxy compounds as a free radical initiator in accordance with the teachings of the present invention have lower viscosities than those prepared graft polyols. using the tertiary butyl peroxy compound as the free radical initiator. However, as illustrated also, considerably less of the initiator is required when tertiary amyl compounds are employed. While it will be apparent that the preferred embodiments of the invention disclosed are well calculated to satisfy the manifested objects, it will be appreciated that the invention is susceptible to modification, variation and change without deviating from the spirit thereof.
TABLE 5 POLIOL
EXAMPLE MAC (g) food charge - RX MOD AN STY LUPERSOL RX TEMP tion (g) (g) (g) (g) (g) (g) (° c)
1 9. 00 to 171., 0 180.0 b 2,, 40 c 80.0 160.0 1.50 125
2 9. 00 a 171. 0 180.0 b 2. 40 c 80.0 160.0 1.80 125
3 9. 00 a 171. 0 180.0 b 2., 40 c 80.0 160.0 1.20 125
4 9. 00 a 171. 0 180.0 b 2., 40 c 80.0 160.0 1.50 125
9., 00 to 171., 0 180.0 b 1., 20 f 80.0 160.0 1.50 125
6 9,, 00 to 171., 0 180.0 b 2., 40 c 80.0 160.0 0.60 125
7 9., 00 a 171., 0 180.0 b 2,, 40 c 80.0 160.0 0.60 125
8 9., 00 to 171., 0 180.0 b 2., 40 c 80.0 160.0 0.90 125
9 9., 00 to 171., 0 180.0 b 2., 40 f 160.0 80.0 1.20 125
12. .00 a 138. .0 150.0 j 3 .00 c 100.0 200.0 1.50 125 llk 12, .00 a 138, .0 150.0 j 3 .00 f 200.0 100.0 1.50 125
12 9,, 00 to 171, .0 180.0 b 2, .40 c 80.0 160.0 1.50 125
13g 9,, 00 to 171, .0 180.0 b 2,, 40 c 80.0 160.0 1.50 125
14g 9,, 00 to 171,, 0 180.0 b 2, .40 c 80.0 160.0 0.90 125
15g 9, .00 to 171, .0 180.0 b 2, .40 c 80.0 160.0 0.60 125
16g 9, .00 to 171. .0 180.0 b 2, .40 c 80.0 160.0 1.20 125
17g 9,, 00 to 171, .0 180.0 b 2, .40 c 80.0 160.0 1.80 125
18g 9. .00 a 171. .0 180.0 b 2, .40 c 80.0 160.0 1.50 125
19g 12 .00 to 138 .0 150.0 j 3 .00 c 100.0 200.0 1.50 125
20g, k 12 .00 to 138 .0 150.0 j 3 .00 f 200.0 100.0 1.50 125 TABLE 5 (Continued)
ADDITION TIME (MINUTES)
EXAMPLE MON POLIOL VISCOSITY% WEIGHT OF mPas, 25 ° C VINI O
1 210 220 5240 38.64 2 210 220 6160 38.66 3 210 220 5440 38.58 4 210 220 5460 38.34 5 210 220 3860 38.30 6 210 220 3850 37.67 7 210 220 3490 37.02 210 220 4440 37.87
9 240 220 3990 38.96
240 250 3420 48.29
11 k 210 250 2750 49.03 12 210 220 5580 38.86
13 g 210 220 6600 38.50
14 g 210 220 5280 38.27
g 210 220 4220 37.71
16 g 210 220 5100 37.81
17 g 21Q 220 8860 38.50
18 g 210 220 5920 38.76
19 g 240 250 3240 48.35
g, k 240 250 3250 48.78 a) Macromer A. b) Polyol H. c) 1-dodecanethiol. f) bromotrichloromethane. g) tertiary butyl peroxy octoate j) Polyol P. k) solids accumulate on the sides of the flask
Claims (33)
1. A process for the preparation of a stable low viscosity graft polymer dispersion comprising polymerizing in the presence of an effective amount of a free radical iator, at least one ethylenically unsaturated monomer in a polyol mixture containing an effective amount of induced non-saturation, wherein the free radical iator comprises a tertiary amyl peroxy compound.
2. A process according to claim 1, wherein the ethylenically unsaturated monomer is present in an amount of about 25 weight percent to about 70 weight percent based on the total weight of all the components.
3. A process according to claim 1, wherein the ethylenically unsaturated monomer or the monomer mixture is present in an amount of about 40 weight percent to about 60 weight percent based on the total weight of all the components. .
A process according to claim 1, wherein the free radical iator is present in an amount between about 0.1 weight percent to about 3.0 weight percent based on the weight of the ethylenically unsaturated monomer. ? - >
5. A process according to claim 1, wherein the free radical iator 5 is present in an amount between about 0.3 weight percent to about 1.0 weight percent based on the weight of the ethylenically unsaturated monomer.
6. A process according to claim 1, wherein the tertiary amyl peroxy compound 10 is selected from the group consisting of tertiary amyl peroxy (2-ethylhexanoate); 1, 1-bis (tertiary amylperoxy) cydohexane; and a mixture of them.
7. A process according to claim 1, wherein the free radical iator 15 comprises a mixture of peroxy (tertiary amyl 2-ethylhexanoate) and 1,1-bis (tertiary amylperoxy peroxy) cydohexane, wherein, the weight ratio of tertiary amyl (2-ethylhexanoate) -α-fc amyl to 1 , 1-bis (tertiary amyl peroxy) cydohexane is about 1:10 a 20 approximately 1: 2.
8. A process according to claim 1, wherein the weight ratio is from 1: 4 to approximately 1: 3.
9. A process according to claim 1, wherein the polyol mixture is present in an amount of about 30 weight percent to about 75 weight percent based on the total weight of all the components.
A process according to claim 1, wherein the polyol mixture is present in an amount of about 40 weight percent to about 60 weight percent based on the total weight of all the components.
11. A process according to claim 1, wherein the dispersion of the graft polymer has an average viscosity of about 2000 to about 15,000 cP, at 25 ° C and a solids content of about 40 percent to about 60 percent , based on the total weight of the dispersion.
12. A process according to claim 1, wherein the polyol mixture contains from about 0.001 mol to about 0.09 mol of non-saturation per mol of the polyol mixture.
13. A process for the preparation of a graft polymer dispersion of high solids content of stable low viscosity, the process comprising in situ polymerizing at least one ethylenically unsaturated monomer in a polyol mixture containing from 0.001 to 0.09 mol of non-saturation induced by mole of the polyol mixture in the presence of an effective amount of a reaction moderator and a free radical iator, wherein the free radical iator comprises a tertiary amyl peroxy compound.
A process according to claim 13, wherein the ethylenically unsaturated monomer is present in an amount of about 25 weight percent to about 70 weight percent based on the total weight of all the components.
15. A process according to claim 13, wherein the ethylenically unsaturated monomer or monomer mixture is present in an amount of about 40 weight percent to about 60 weight percent based on the total weight of all the components.
16. A process according to claim 13, wherein the free radical initiator is present in an amount of between about 0.1 weight percent to about 3.0 weight percent based on the weight of the ethylenically unsaturated monomer.
17. A process according to claim 13 wherein the free radical initiator is present in an amount of between about 0.3 weight percent to about 1.0 weight percent based on the weight of the ethylenically unsaturated monomer.
18. A process according to claim 13 wherein the tertiary amyl peroxy compound is selected from the group consisting of tertiary amyl peroxy (2-ethylhexanoate); 1, 1-bis (tertiary amylperoxy) cydohexane; and mixtures thereof.
19. A process according to claim 13 wherein the free radical initiator comprises a mixture of tertiary amyl peroxy (2-ethylhexanoate) and 1,1-bis (tertiary amyl peroxy) cydohexane, wherein the weight ratio of tertiary amyl peroxy (2-ethylhexanoate) to 1,1-bis (tertiary amyl peroxy) cydohexane is from about 1:10 to about 1: 2.
20. A process according to claim 19, wherein the weight ratio is from 1: 4 to about 1: 3.
21. A process according to claim 13, wherein the polyol mixture is present in an amount of about 30 weight percent to about 75 weight percent based on the total weight of all the components.
22. A process according to claim 13 wherein the polyol mixture is present in an amount of about 40 weight percent to about 60 weight percent based on the total weight of all the components.
23. A process according to claim 13, wherein the graft polymer dispersion has an average viscosity of from about 2000 to about 15,000 cP at 25 ° C and a solids content of from about 40 percent to about 60 percent, based on the total weight of the dispersion.
24. A process according to claim 13 wherein the monomer is selected from the group consisting of blends of styrene and acrylonitrile.
25. A process according to claim 13, wherein the polyol mixture comprises a macromer containing isomerized maleate.
26. A process according to claim 13, wherein the polyol mixture comprises a macromer prepared from a compound containing unsaturated fumarate.
27. A process for the preparation of a stable low viscosity graft polymer dispersion, the process comprising polymerizing in the presence of a free radical initiator (a) at least one ethylenically unsaturated monomer in (b) a polyol mixture comprising (1) a polyoxyalkylene polyether polyol having an equivalent weight of 100 to 10,000; and (2) a - 5E macromers containing an effective amount of non-saturation induced, wherein the free radical initiator comprises a tertiary amyl peroxy compound. •
28. A process according to claim 27, wherein the ethylenically unsaturated monomer or a monomer mixture is present in an amount of about 40 weight percent to about 60 weight percent based on the total weight of the monomer. all the components •
29. A process according to claim 27, wherein the free radical initiator is present in an amount of between about 0.3 weight percent to about 1.0 weight percent based on the weight of the ethylenically unsaturated monomer.
30. A process according to claim 27, wherein the tertiary amyl peroxy compound is selected from the group consisting of tertiary amyl peroxy (2-ethylhexanoate); 1, 1-bis (tertiary amylperoxy) cydohexane; and a mixture of them.
31. A process according to claim 27, wherein the free radical initiator comprises a mixture of tertiary amyl peroxy (2-ethylhexanoate) and 1,1-bis (tertiary amyl peroxy) cyclohexane, wherein the ratio by weight of peroxy (2-ethylhexanoate) 25 tertiary amyl to 1,1-bis (tertiary amyl peroxy) cydohexane is from about 1: 4 to about 1: 3.
32. A process according to claim 27, wherein the polyol mixture is present in an amount of about 40 weight percent to about 60 weight percent based on the total weight of all the components.
33. A process according to claim 27, wherein the polyol mixture contains from about 0.001 to about 0.09 mol of non-saturation per mole of the polyol mixture.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US09283492 | 1999-04-01 |
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MXPA00001781A true MXPA00001781A (en) | 2001-06-26 |
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