CA1045285A - Polymere de polyurethanne en particules - Google Patents

Polymere de polyurethanne en particules

Info

Publication number: CA1045285A
Authority: CA; Canada
Prior art keywords: polymer; caprolactone; acrylate; poly; polyurethane polymer
Prior art date: 1973-12-03
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA212,905A

Other languages

English (en)

Other versions

CA212905S (en

Inventor

Frank P. Del Giudice

Richard M. Gerkin

Frank E. Critchfield

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Union Carbide Corp

Original Assignee

Union Carbide Corp

Priority date (The priority date 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 date listed.)

1973-12-03

Filing date

1974-11-04

Publication date

1978-12-26

1974-11-04 Application filed by Union Carbide Corp filed Critical Union Carbide Corp

1978-12-26 Application granted granted Critical

1978-12-26 Publication of CA1045285A publication Critical patent/CA1045285A/fr

Status Expired legal-status Critical Current

Links

229920000642 polymer Polymers 0.000 title claims abstract description 134
238000004519 manufacturing process Methods 0.000 title claims abstract description 11
239000004814 polyurethane Substances 0.000 title claims description 63
229920002635 polyurethane Polymers 0.000 title claims description 57
239000004433 Thermoplastic polyurethane Substances 0.000 claims abstract description 24
239000003795 chemical substances by application Substances 0.000 claims description 81
239000000047 product Substances 0.000 claims description 65
238000000034 method Methods 0.000 claims description 59
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 53
-1 diisocyanate compound Chemical class 0.000 claims description 51
DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 39
239000000178 monomer Substances 0.000 claims description 33
239000003054 catalyst Substances 0.000 claims description 26
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 25
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 22
239000000203 mixture Substances 0.000 claims description 21
229920001610 polycaprolactone Polymers 0.000 claims description 21
229920002803 thermoplastic polyurethane Polymers 0.000 claims description 21
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 18
229920002554 vinyl polymer Polymers 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 16
150000002009 diols Chemical class 0.000 claims description 16
229920000578 graft copolymer Polymers 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 15
239000000470 constituent Substances 0.000 claims description 14
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 13
UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 11
229920001400 block copolymer Polymers 0.000 claims description 11
KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical group [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 claims description 11
229920000728 polyester Polymers 0.000 claims description 10
229920006395 saturated elastomer Polymers 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 10
LVGFPWDANALGOY-UHFFFAOYSA-N 8-methylnonyl prop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C=C LVGFPWDANALGOY-UHFFFAOYSA-N 0.000 claims description 9
239000007787 solid Substances 0.000 claims description 9
229930195733 hydrocarbon Natural products 0.000 claims description 8
150000002430 hydrocarbons Chemical class 0.000 claims description 8
COCLLEMEIJQBAG-UHFFFAOYSA-N 8-methylnonyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C(C)=C COCLLEMEIJQBAG-UHFFFAOYSA-N 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
239000000843 powder Substances 0.000 claims description 7
125000005442 diisocyanate group Chemical group 0.000 claims description 6
239000007788 liquid Substances 0.000 claims description 6
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 5
239000004721 Polyphenylene oxide Substances 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
239000004632 polycaprolactone Substances 0.000 claims description 5
229920001169 thermoplastic Polymers 0.000 claims description 5
229930195734 saturated hydrocarbon Natural products 0.000 claims description 4
239000004416 thermosoftening plastic Substances 0.000 claims description 4
239000004970 Chain extender Substances 0.000 claims description 3
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
239000004615 ingredient Substances 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 2
230000003197 catalytic effect Effects 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims 3
239000007795 chemical reaction product Substances 0.000 claims 3
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims 2
DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical group CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 claims 1
229920003225 polyurethane elastomer Polymers 0.000 abstract description 2
229920001577 copolymer Polymers 0.000 description 42
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 25
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
150000001875 compounds Chemical class 0.000 description 18
229920005862 polyol Polymers 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 14
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 14
GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 13
229940063557 methacrylate Drugs 0.000 description 13
150000003077 polyols Chemical class 0.000 description 13
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 12
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 11
150000002334 glycols Chemical class 0.000 description 9
229940044192 2-hydroxyethyl methacrylate Drugs 0.000 description 8
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
238000006116 polymerization reaction Methods 0.000 description 8
150000002148 esters Chemical class 0.000 description 7
LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 7
150000002596 lactones Chemical class 0.000 description 6
HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 6
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 5
125000002947 alkylene group Chemical group 0.000 description 5
239000000463 material Substances 0.000 description 5
239000002245 particle Substances 0.000 description 5
229920000570 polyether Polymers 0.000 description 5
239000000376 reactant Substances 0.000 description 5
239000007858 starting material Substances 0.000 description 5
OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 4
239000004215 Carbon black (E152) Substances 0.000 description 4
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
239000003999 initiator Substances 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
DMLCMIXRGQUXPR-UHFFFAOYSA-N octadecyl hex-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C=CCCC DMLCMIXRGQUXPR-UHFFFAOYSA-N 0.000 description 4
229940065472 octyl acrylate Drugs 0.000 description 4
ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 4
TWFLXCJGMMOLAY-UHFFFAOYSA-N pentacosyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCOC(=O)C(C)=C TWFLXCJGMMOLAY-UHFFFAOYSA-N 0.000 description 4
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 4
GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 3
IYBOGQYZTIIPNI-UHFFFAOYSA-N 2-methylhexano-6-lactone Chemical compound CC1CCCCOC1=O IYBOGQYZTIIPNI-UHFFFAOYSA-N 0.000 description 3
SPEHEHYVDRYEDX-UHFFFAOYSA-N 3-methyloxan-2-one Chemical compound CC1CCCOC1=O SPEHEHYVDRYEDX-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
239000012948 isocyanate Substances 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
229920001451 polypropylene glycol Polymers 0.000 description 3
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
UGIJCMNGQCUTPI-UHFFFAOYSA-N 2-aminoethyl prop-2-enoate Chemical compound NCCOC(=O)C=C UGIJCMNGQCUTPI-UHFFFAOYSA-N 0.000 description 2
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 2
YGTVWCBFJAVSMS-UHFFFAOYSA-N 5-hydroxypentyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCO YGTVWCBFJAVSMS-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
239000004606 Fillers/Extenders Substances 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
241001163743 Perlodes Species 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
FTWHFXMUJQRNBK-UHFFFAOYSA-N alpha-Methylen-gamma-aminobuttersaeure Natural products NCCC(=C)C(O)=O FTWHFXMUJQRNBK-UHFFFAOYSA-N 0.000 description 2
230000001588 bifunctional effect Effects 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical class C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
150000004985 diamines Chemical class 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
ILHIHKRJJMKBEE-UHFFFAOYSA-N hydroperoxyethane Chemical compound CCOO ILHIHKRJJMKBEE-UHFFFAOYSA-N 0.000 description 2
GJIDOLBZYSCZRX-UHFFFAOYSA-N hydroxymethyl prop-2-enoate Chemical compound OCOC(=O)C=C GJIDOLBZYSCZRX-UHFFFAOYSA-N 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
150000002513 isocyanates Chemical class 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
238000002156 mixing Methods 0.000 description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
150000002978 peroxides Chemical class 0.000 description 2
229920000196 poly(lauryl methacrylate) Polymers 0.000 description 2
229920001481 poly(stearyl methacrylate) Polymers 0.000 description 2
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000000758 substrate Substances 0.000 description 2
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
AXKGIPZJYUNAIW-UHFFFAOYSA-N (4-aminophenyl)methanol Chemical compound NC1=CC=C(CO)C=C1 AXKGIPZJYUNAIW-UHFFFAOYSA-N 0.000 description 1
LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-dichloroethene Chemical compound ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 description 1
125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
VPVXHAANQNHFSF-UHFFFAOYSA-N 1,4-dioxan-2-one Chemical compound O=C1COCCO1 VPVXHAANQNHFSF-UHFFFAOYSA-N 0.000 description 1
ODNVMSBMPXJCDX-UHFFFAOYSA-N 2-(decylamino)ethyl prop-2-enoate Chemical compound CCCCCCCCCCNCCOC(=O)C=C ODNVMSBMPXJCDX-UHFFFAOYSA-N 0.000 description 1
GDDMZUCYXYKPNC-UHFFFAOYSA-N 2-(methylamino)propyl prop-2-enoate Chemical compound CNC(C)COC(=O)C=C GDDMZUCYXYKPNC-UHFFFAOYSA-N 0.000 description 1
GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 1
WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 1
NIONDZDPPYHYKY-UHFFFAOYSA-N 2-hexenoic acid Chemical compound CCCC=CC(O)=O NIONDZDPPYHYKY-UHFFFAOYSA-N 0.000 description 1
229940095095 2-hydroxyethyl acrylate Drugs 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
CJNWCYZELLHABH-UHFFFAOYSA-N 3,3-dimethyloxan-2-one Chemical compound CC1(C)CCCOC1=O CJNWCYZELLHABH-UHFFFAOYSA-N 0.000 description 1
LROFMHLJBOIJHA-UHFFFAOYSA-N 3,3-dimethyloxepan-2-one Chemical compound CC1(C)CCCCOC1=O LROFMHLJBOIJHA-UHFFFAOYSA-N 0.000 description 1
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
NNZJTGAFGUXZSQ-UHFFFAOYSA-N 5-(methylamino)pentyl prop-2-enoate Chemical compound CNCCCCCOC(=O)C=C NNZJTGAFGUXZSQ-UHFFFAOYSA-N 0.000 description 1
INRQKLGGIVSJRR-UHFFFAOYSA-N 5-hydroxypentyl prop-2-enoate Chemical compound OCCCCCOC(=O)C=C INRQKLGGIVSJRR-UHFFFAOYSA-N 0.000 description 1
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
229920001305 Poly(isodecyl(meth)acrylate) Polymers 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 1
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229940048053 acrylate Drugs 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
125000002015 acyclic group Chemical group 0.000 description 1
230000002411 adverse Effects 0.000 description 1
238000007605 air drying Methods 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
QHOTVLWYQNKORC-UHFFFAOYSA-N aminomethyl prop-2-enoate Chemical compound NCOC(=O)C=C QHOTVLWYQNKORC-UHFFFAOYSA-N 0.000 description 1
239000012431 aqueous reaction media Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000001273 butane Substances 0.000 description 1
238000003490 calendering Methods 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
150000001924 cycloalkanes Chemical class 0.000 description 1
125000004956 cyclohexylene group Chemical group 0.000 description 1
238000010908 decantation Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
PNOXNTGLSKTMQO-UHFFFAOYSA-L diacetyloxytin Chemical compound CC(=O)O[Sn]OC(C)=O PNOXNTGLSKTMQO-UHFFFAOYSA-L 0.000 description 1
239000012975 dibutyltin dilaurate Substances 0.000 description 1
239000000539 dimer Substances 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
AFSIMBWBBOJPJG-UHFFFAOYSA-N ethenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=C AFSIMBWBBOJPJG-UHFFFAOYSA-N 0.000 description 1
SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
238000010559 graft polymerization reaction Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
230000003993 interaction Effects 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
238000000465 moulding Methods 0.000 description 1
LJGXNCLPWGNTGE-UHFFFAOYSA-N n-(aminomethyl)prop-2-enamide Chemical compound NCNC(=O)C=C LJGXNCLPWGNTGE-UHFFFAOYSA-N 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
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
125000005474 octanoate group Chemical group 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003921 oil Substances 0.000 description 1
229940049964 oleate Drugs 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
125000005702 oxyalkylene group Chemical group 0.000 description 1
229940059574 pentaerithrityl Drugs 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-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
239000003209 petroleum derivative Substances 0.000 description 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
229920001042 poly(δ-valerolactone) Polymers 0.000 description 1
229920002239 polyacrylonitrile Polymers 0.000 description 1
125000003367 polycyclic group Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
230000002028 premature Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
238000004886 process control Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
230000035939 shock Effects 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
ATZHWSYYKQKSSY-UHFFFAOYSA-N tetradecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)=C ATZHWSYYKQKSSY-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
125000005628 tolylene group Chemical group 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
- C08J3/11—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids from solid polymers
- 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
- C08G18/08—Processes
- C08G18/0838—Manufacture of polymers in the presence of non-reactive compounds
- C08G18/0842—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents
- C08G18/0861—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers
- C08G18/0871—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers the dispersing or dispersed phase being organic
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/12—Powdering or granulating
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes

Landscapes

Chemical & Material Sciences (AREA)
Dispersion Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Manufacturing & Machinery (AREA)
Polyurethanes Or Polyureas (AREA)

CA212,905A 1973-12-03 1974-11-04 Polymere de polyurethanne en particules Expired CA1045285A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US42133173A	1973-12-03	1973-12-03

Publications (1)

Publication Number	Publication Date
CA1045285A true CA1045285A (fr)	1978-12-26

Family

ID=23670072

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA212,905A Expired CA1045285A (fr)	1973-12-03	1974-11-04	Polymere de polyurethanne en particules

Country Status (6)

Country	Link
JP (1)	JPS5087197A (fr)
CA (1)	CA1045285A (fr)
DE (1)	DE2456927A1 (fr)
FR (1)	FR2253036A1 (fr)
GB (1)	GB1486224A (fr)
SE (1)	SE7415083L (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4179479A (en) *	1978-04-20	1979-12-18	Mobay Chemical Corporation	Thermoplastic polyurethane blends containing a processing aid
GB8317354D0 (en) *	1983-06-27	1983-07-27	Ici Plc	Polymer-modified polyols
US4855164A (en) *	1988-02-12	1989-08-08	Ppg Industries, Inc.	Stable multiphase coating compositions
DE3928149A1 (de) *	1989-08-25	1991-02-28	Bayer Ag	Verfahren zur herstellung von polyurethanpulvern
DE3928150A1 (de) *	1989-08-25	1991-02-28	Bayer Ag	Grenzflaechenaktive copolymere und ihre verwendung zur herstellung von polyurethanpulvern

1974
- 1974-11-04 CA CA212,905A patent/CA1045285A/fr not_active Expired
- 1974-12-02 SE SE7415083A patent/SE7415083L/xx unknown
- 1974-12-02 DE DE19742456927 patent/DE2456927A1/de active Pending
- 1974-12-02 JP JP49137095A patent/JPS5087197A/ja active Pending
- 1974-12-02 GB GB52087/74A patent/GB1486224A/en not_active Expired
- 1974-12-16 FR FR7441415A patent/FR2253036A1/fr not_active Withdrawn

Also Published As

Publication number	Publication date
GB1486224A (en)	1977-09-21
JPS5087197A (fr)	1975-07-14
SE7415083L (fr)	1975-06-04
FR2253036A1 (fr)	1975-06-27
DE2456927A1 (de)	1975-06-05

Publication	Publication Date	Title
US4000218A (en)	1976-12-28	Process for preparing particulate polyurethane polymers and the polymers derived therefrom
US4224427A (en)	1980-09-23	Process for preparing hydrogels as spherical beads of large size
US3304273A (en)	1967-02-14	Method of preparing polyurethanes from liquid, stable, reactive, filmforming polymer/polyol mixtures formed by polymerizing an ethylenically unsaturated monomer in a polyol
US3850861A (en)	1974-11-26	Preparation and formulation of polyurethane foams
US4102846A (en)	1978-07-25	Stable dispersions of polymer particles containing sub-particles of a solid modifying agent and process for making same
EP0208734B1 (fr)	1990-12-27	Copolymeres-bloc de polysiloxane-polylactone
CA2019422C (fr)	2000-11-21	Macromeres pour polyols de greffe; polyols ainsi obtenus
US4198330A (en)	1980-04-15	Polyurethane latices modified by a vinyl polymer
JPH0931142A (ja)	1997-02-04	低粘度高分子量ポリオール、その調製方法並びにポリウレタンフォーム製造へのその使用
US5814675A (en)	1998-09-29	Process for the preparation of polyurethane microspheres
CA1095341A (fr)	1981-02-10	Methode de revetement de tissu en matiere textile
US3264234A (en)	1966-08-02	Dispersion polymerisation of monomer in presence of polymeric solvated constituent
CA1045285A (fr)	1978-12-26	Polymere de polyurethanne en particules
CA1060129A (fr)	1979-08-07	Dispersions de copolymeres employant des stabilisants amphipathiques
US3892821A (en)	1975-07-01	Polyesters blended with cyclic ester polymers
JPS6150091B2 (fr)	1986-11-01
US3689593A (en)	1972-09-05	Chain transfer linked urethane graft copolymers
JPH07292034A (ja)	1995-11-07	プロポキシ化アリルアルコールから誘導されるポリマー
US3865898A (en)	1975-02-11	Process for preparing block copolymers with carbamate linkages between a polyvinyl chain and a polymer having active hydrogens
US2880192A (en)	1959-03-31	Rubbery composition comprising a crystalline polyester and a liquid polyester reacted with a diisocyanate
US3859381A (en)	1975-01-07	Crosslinked polyurethanes from polyurethane precursors and vinyl monomers
US4533695A (en)	1985-08-06	Non-aqueous dispersions based on capped stabilizers and reactants comprising polyfunctional monomers II
CA1046691A (fr)	1979-01-16	Particules fines d'uree-urethanne
EP0982330A1 (fr)	2000-03-01	Procédé amélioré pour la préparation de particules sphériques de polyuréthane
US4528317A (en)	1985-07-09	Non-aqueous dispersions based on capped stabilizers and reactants comprising polyfunctional monomers II