DE69233638T2 - Zweifach stabilisierte mikropartikel - Google Patents
Zweifach stabilisierte mikropartikel Download PDFInfo
- Publication number
- DE69233638T2 DE69233638T2 DE69233638T DE69233638T DE69233638T2 DE 69233638 T2 DE69233638 T2 DE 69233638T2 DE 69233638 T DE69233638 T DE 69233638T DE 69233638 T DE69233638 T DE 69233638T DE 69233638 T2 DE69233638 T2 DE 69233638T2
- Authority
- DE
- Germany
- Prior art keywords
- polymer
- stabilized
- methacrylate
- acrylate
- microc
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000011859 microparticle Substances 0.000 title claims description 43
- 229920000642 polymer Polymers 0.000 claims description 75
- 239000000203 mixture Substances 0.000 claims description 57
- 239000003381 stabilizer Substances 0.000 claims description 57
- 239000000178 monomer Substances 0.000 claims description 35
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 26
- 230000000087 stabilizing effect Effects 0.000 claims description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 20
- 239000007788 liquid Substances 0.000 claims description 19
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 15
- 230000009021 linear effect Effects 0.000 claims description 15
- 239000002245 particle Substances 0.000 claims description 15
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 claims description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 13
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 13
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 13
- 239000000049 pigment Substances 0.000 claims description 12
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 11
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 10
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 10
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 10
- 229920000058 polyacrylate Polymers 0.000 claims description 10
- 229910000077 silane Inorganic materials 0.000 claims description 10
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 claims description 9
- 229920002554 vinyl polymer Polymers 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 238000000576 coating method Methods 0.000 claims description 8
- 229940114072 12-hydroxystearic acid Drugs 0.000 claims description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 7
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 claims description 7
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 7
- 239000004593 Epoxy Substances 0.000 claims description 7
- 239000011248 coating agent Substances 0.000 claims description 7
- 238000012674 dispersion polymerization Methods 0.000 claims description 7
- 229920000578 graft copolymer Polymers 0.000 claims description 7
- 239000012948 isocyanate Substances 0.000 claims description 7
- 150000002513 isocyanates Chemical class 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
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- 238000000518 rheometry Methods 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- 229920000728 polyester Polymers 0.000 claims description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003431 cross linking reagent Substances 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- -1 2-ethylhexyl methyl Chemical group 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- 239000011976 maleic acid Substances 0.000 claims description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 2
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 2
- 229920000196 poly(lauryl methacrylate) Polymers 0.000 claims description 2
- 229920001481 poly(stearyl methacrylate) Polymers 0.000 claims description 2
- 229920005906 polyester polyol Polymers 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 150000003440 styrenes Chemical class 0.000 claims description 2
- CBKJLMZJKHOGEQ-UHFFFAOYSA-N 2-(oxiran-2-yl)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCC1CO1 CBKJLMZJKHOGEQ-UHFFFAOYSA-N 0.000 claims 1
- 229920006243 acrylic copolymer Polymers 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000010410 layer Substances 0.000 description 17
- 238000007792 addition Methods 0.000 description 14
- 239000008199 coating composition Substances 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- 239000011230 binding agent Substances 0.000 description 13
- 239000000306 component Substances 0.000 description 13
- 239000006185 dispersion Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 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 11
- 239000000243 solution Substances 0.000 description 11
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 239000008358 core component Substances 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 5
- 239000004611 light stabiliser Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- BWSZXUOMATYHHI-UHFFFAOYSA-N tert-butyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(C)(C)C BWSZXUOMATYHHI-UHFFFAOYSA-N 0.000 description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000012986 chain transfer agent Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 238000005189 flocculation Methods 0.000 description 3
- 230000016615 flocculation Effects 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000003801 milling Methods 0.000 description 3
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 229960002887 deanol Drugs 0.000 description 2
- 239000012972 dimethylethanolamine Substances 0.000 description 2
- 238000007590 electrostatic spraying Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 238000007342 radical addition reaction Methods 0.000 description 2
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- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical class C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 1
- CGLVZFOCZLHKOH-UHFFFAOYSA-N 8,18-dichloro-5,15-diethyl-5,15-dihydrodiindolo(3,2-b:3',2'-m)triphenodioxazine Chemical compound CCN1C2=CC=CC=C2C2=C1C=C1OC3=C(Cl)C4=NC(C=C5C6=CC=CC=C6N(C5=C5)CC)=C5OC4=C(Cl)C3=NC1=C2 CGLVZFOCZLHKOH-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
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- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 239000004609 Impact Modifier Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000000498 ball milling Methods 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 239000010428 baryte Substances 0.000 description 1
- 229910052601 baryte Inorganic materials 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000010960 cold rolled steel Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
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- 238000009826 distribution Methods 0.000 description 1
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- 238000001035 drying Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
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- 238000001652 electrophoretic deposition Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-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
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- 229910021485 fumed silica Inorganic materials 0.000 description 1
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- 235000019239 indanthrene blue RS Nutrition 0.000 description 1
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
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- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
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- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
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- XTBAPWCYTNCZTO-UHFFFAOYSA-N isoindol-1-one Chemical class C1=CC=C2C(=O)N=CC2=C1 XTBAPWCYTNCZTO-UHFFFAOYSA-N 0.000 description 1
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical class C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
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- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 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
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
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- 150000002979 perylenes Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
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- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
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- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
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- 238000010008 shearing Methods 0.000 description 1
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- 150000004760 silicates Chemical class 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
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- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 229940124543 ultraviolet light absorber Drugs 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/04—Polymerisation in solution
- C08F2/06—Organic solvent
- C08F2/08—Organic solvent with the aid of dispersing agents for the polymer
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Graft Or Block Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81318491A | 1991-12-24 | 1991-12-24 | |
| US813184 | 1991-12-24 | ||
| PCT/US1992/010782 WO1993013111A1 (en) | 1991-12-24 | 1992-12-17 | Dual stabilized microparticles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69233638D1 DE69233638D1 (de) | 2006-08-24 |
| DE69233638T2 true DE69233638T2 (de) | 2007-07-12 |
Family
ID=25211694
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69233638T Expired - Lifetime DE69233638T2 (de) | 1991-12-24 | 1992-12-17 | Zweifach stabilisierte mikropartikel |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5468801A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0618934B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JPH07503981A (cg-RX-API-DMAC7.html) |
| BR (1) | BR9207043A (cg-RX-API-DMAC7.html) |
| CA (1) | CA2125647C (cg-RX-API-DMAC7.html) |
| DE (1) | DE69233638T2 (cg-RX-API-DMAC7.html) |
| TW (1) | TW303372B (cg-RX-API-DMAC7.html) |
| WO (1) | WO1993013111A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996025466A1 (en) * | 1995-02-17 | 1996-08-22 | E.I. Du Pont De Nemours And Company | Crack-resistant one-package coating composition |
| US5985956A (en) * | 1996-02-14 | 1999-11-16 | E. I. Du Pont De Nemours And Company | Crack-resistant one-package coating composition |
| US5770648A (en) * | 1996-10-29 | 1998-06-23 | E. I. Du Pont De Nemours And Company | Pigment dispersions containing aqueous branched polymer dispersant |
| US5955532A (en) * | 1997-07-17 | 1999-09-21 | E. I. Du Pont De Nemours And Company | Aqueous coating composition of a self-stabilized crosslinked latex |
| US5859136A (en) * | 1997-11-03 | 1999-01-12 | E. I. Du Pont De Nemours And Company | Coating composition containing an amine functional dispersed polymer and an isocyanate curing agent |
| JP2000119587A (ja) * | 1998-10-20 | 2000-04-25 | Clariant Polymer Kk | コーティング組成物 |
| ATE295143T1 (de) * | 1999-04-07 | 2005-05-15 | Ciba Sc Holding Ag | Flüssige polymerdispersionen, ihre herstellung und verwendung |
| US6372840B1 (en) | 1999-06-28 | 2002-04-16 | Ppg Industries Ohio, Inc. | Dual stabilized dispersions of gelled polymeric microparticles and coatings produced therefrom |
| US7094369B2 (en) | 2002-03-29 | 2006-08-22 | Scimed Life Systems, Inc. | Processes for manufacturing polymeric microspheres |
| US7131997B2 (en) | 2002-03-29 | 2006-11-07 | Scimed Life Systems, Inc. | Tissue treatment |
| US7462366B2 (en) | 2002-03-29 | 2008-12-09 | Boston Scientific Scimed, Inc. | Drug delivery particle |
| US7053134B2 (en) | 2002-04-04 | 2006-05-30 | Scimed Life Systems, Inc. | Forming a chemically cross-linked particle of a desired shape and diameter |
| AU2003240000A1 (en) | 2002-06-12 | 2003-12-31 | Boston Scientific Limited | Bulking agents |
| US7244784B2 (en) * | 2002-06-14 | 2007-07-17 | Rohm And Haas Company | Aqueous nanoparticle dispersions |
| US7842377B2 (en) | 2003-08-08 | 2010-11-30 | Boston Scientific Scimed, Inc. | Porous polymeric particle comprising polyvinyl alcohol and having interior to surface porosity-gradient |
| US7449236B2 (en) | 2002-08-09 | 2008-11-11 | Boston Scientific Scimed, Inc. | Porous polymeric particle comprising polyvinyl alcohol and having interior to surface porosity-gradient |
| US8012454B2 (en) | 2002-08-30 | 2011-09-06 | Boston Scientific Scimed, Inc. | Embolization |
| US7883490B2 (en) | 2002-10-23 | 2011-02-08 | Boston Scientific Scimed, Inc. | Mixing and delivery of therapeutic compositions |
| US7588825B2 (en) | 2002-10-23 | 2009-09-15 | Boston Scientific Scimed, Inc. | Embolic compositions |
| US7976823B2 (en) | 2003-08-29 | 2011-07-12 | Boston Scientific Scimed, Inc. | Ferromagnetic particles and methods |
| US7901770B2 (en) | 2003-11-04 | 2011-03-08 | Boston Scientific Scimed, Inc. | Embolic compositions |
| US7736671B2 (en) | 2004-03-02 | 2010-06-15 | Boston Scientific Scimed, Inc. | Embolization |
| US8173176B2 (en) | 2004-03-30 | 2012-05-08 | Boston Scientific Scimed, Inc. | Embolization |
| US7311861B2 (en) | 2004-06-01 | 2007-12-25 | Boston Scientific Scimed, Inc. | Embolization |
| US8425550B2 (en) | 2004-12-01 | 2013-04-23 | Boston Scientific Scimed, Inc. | Embolic coils |
| US7858183B2 (en) | 2005-03-02 | 2010-12-28 | Boston Scientific Scimed, Inc. | Particles |
| US7727555B2 (en) | 2005-03-02 | 2010-06-01 | Boston Scientific Scimed, Inc. | Particles |
| US7963287B2 (en) | 2005-04-28 | 2011-06-21 | Boston Scientific Scimed, Inc. | Tissue-treatment methods |
| US9463426B2 (en) | 2005-06-24 | 2016-10-11 | Boston Scientific Scimed, Inc. | Methods and systems for coating particles |
| US8007509B2 (en) | 2005-10-12 | 2011-08-30 | Boston Scientific Scimed, Inc. | Coil assemblies, components and methods |
| US8152839B2 (en) | 2005-12-19 | 2012-04-10 | Boston Scientific Scimed, Inc. | Embolic coils |
| US8101197B2 (en) | 2005-12-19 | 2012-01-24 | Stryker Corporation | Forming coils |
| US7947368B2 (en) | 2005-12-21 | 2011-05-24 | Boston Scientific Scimed, Inc. | Block copolymer particles |
| US7501179B2 (en) | 2005-12-21 | 2009-03-10 | Boston Scientific Scimed, Inc. | Block copolymer particles |
| US8414927B2 (en) | 2006-11-03 | 2013-04-09 | Boston Scientific Scimed, Inc. | Cross-linked polymer particles |
| US20080286724A1 (en) | 2007-05-18 | 2008-11-20 | Ormco Corporation | Orthodontic adhesives |
| US8513321B2 (en) | 2010-11-05 | 2013-08-20 | Ppg Industries Ohio, Inc. | Dual cure coating compositions, methods of coating a substrate, and related coated substrates |
| US8901198B2 (en) | 2010-11-05 | 2014-12-02 | Ppg Industries Ohio, Inc. | UV-curable coating compositions, multi-component composite coatings, and related coated substrates |
| JP2014514367A (ja) * | 2010-11-15 | 2014-06-19 | サン ケミカル コーポレイション | 印刷用インクの凝固特性および耐摩擦性を改善するための組成物および方法 |
| US9434828B2 (en) | 2010-12-08 | 2016-09-06 | Ppg Industries Ohio, Inc. | Non-aqueous dispersions comprising a nonlinear acrylic stabilizer |
| US9346959B2 (en) | 2010-12-08 | 2016-05-24 | Ppg Industries Ohio, Inc. | Non-aqueous dispersions comprising a nonlinear acrylic stabilizer |
| CN104093797A (zh) * | 2011-12-08 | 2014-10-08 | 太阳化学公司 | 含非水分散物的罩印清漆 |
| US20140128508A1 (en) * | 2012-11-06 | 2014-05-08 | Ppg Industries Ohio, Inc. | Non-aqueous dispersions comprising an acrylic polymer stabilizer and an aliphatic polyester stabilized seed polymer |
| KR102458569B1 (ko) | 2017-07-14 | 2022-10-24 | 피피지 인더스트리즈 오하이오 인코포레이티드 | 반응성 작용성 중합체 및 폴리실록산 수지를 포함하는 경화성 필름-형성 조성물, 다층 복합체 코팅 및 이들의 사용 방법 |
| US20200325289A1 (en) * | 2019-04-15 | 2020-10-15 | Ppg Industries Ohio, Inc. | Curable film-forming compositions containing rheology modifiers comprising non-aqueous dispersions |
| US11920023B2 (en) | 2022-04-28 | 2024-03-05 | Rohm And Haas Electronic Materials Llc. | Composite materials for dielectric applications |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3928255A (en) * | 1971-02-22 | 1975-12-23 | Cpc International Inc | Chemically joined, phase separated self-cured hydrophilic thermoplastic graft copolymers and their preparation |
| US4147688A (en) * | 1975-03-19 | 1979-04-03 | Ppg Industries, Inc. | Method of preparing dispersions of gelled polymeric microparticles and products produced thereby |
| NZ186955A (en) * | 1977-04-25 | 1980-10-08 | Ici Ltd | Coating process using a sprayable composition comprising a polyester and polymeric microparticles |
| US4639394A (en) * | 1985-04-01 | 1987-01-27 | Ppg Industries, Inc. | Non-aqueous dispersions prepared with styrene polymer dispersion stabilizers |
| US4849480A (en) * | 1985-10-23 | 1989-07-18 | E. I. Du Pont De Nemours And Company | Crosslinked polymer microparticle |
| US4746714A (en) * | 1986-06-17 | 1988-05-24 | E. I. Du Pont De Nemours And Company | Stabilized acrylic resin |
| US5010140A (en) * | 1989-05-31 | 1991-04-23 | E. I. Du Pont De Nemours And Company | Process for preparing stabilized polymer dispersion |
| JPH0670110B2 (ja) * | 1989-10-13 | 1994-09-07 | 関西ペイント株式会社 | 重合体微粒子の分散液 |
-
1992
- 1992-12-17 JP JP5511717A patent/JPH07503981A/ja active Pending
- 1992-12-17 BR BR9207043A patent/BR9207043A/pt not_active IP Right Cessation
- 1992-12-17 WO PCT/US1992/010782 patent/WO1993013111A1/en not_active Ceased
- 1992-12-17 CA CA002125647A patent/CA2125647C/en not_active Expired - Fee Related
- 1992-12-17 EP EP93901306A patent/EP0618934B1/en not_active Expired - Lifetime
- 1992-12-17 DE DE69233638T patent/DE69233638T2/de not_active Expired - Lifetime
-
1993
- 1993-10-18 TW TW082108705A patent/TW303372B/zh active
-
1994
- 1994-09-22 US US08/310,053 patent/US5468801A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0618934B1 (en) | 2006-07-12 |
| DE69233638D1 (de) | 2006-08-24 |
| WO1993013111A1 (en) | 1993-07-08 |
| JPH07503981A (ja) | 1995-04-27 |
| BR9207043A (pt) | 1995-12-05 |
| US5468801A (en) | 1995-11-21 |
| CA2125647C (en) | 1997-12-30 |
| EP0618934A1 (en) | 1994-10-12 |
| CA2125647A1 (en) | 1993-07-08 |
| TW303372B (cg-RX-API-DMAC7.html) | 1997-04-21 |
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