CA1111191A - Process for the manufacture of soluble copolymers which contain hydroxyl groups and can be crosslinked with organic polyisocyanates - Google Patents
Process for the manufacture of soluble copolymers which contain hydroxyl groups and can be crosslinked with organic polyisocyanatesInfo
- Publication number
- CA1111191A CA1111191A CA279,556A CA279556A CA1111191A CA 1111191 A CA1111191 A CA 1111191A CA 279556 A CA279556 A CA 279556A CA 1111191 A CA1111191 A CA 1111191A
- Authority
- CA
- Canada
- Prior art keywords
- weight
- alpha
- copolymer
- employed
- mixture
- 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
Links
- 229920001577 copolymer Polymers 0.000 title claims abstract description 116
- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 44
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 40
- 238000000034 method Methods 0.000 title claims abstract description 30
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title claims description 54
- 239000004922 lacquer Substances 0.000 claims abstract description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000000758 substrate Substances 0.000 claims abstract description 15
- 239000000306 component Substances 0.000 claims description 64
- 239000002253 acid Substances 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 44
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 34
- 238000000576 coating method Methods 0.000 claims description 33
- 150000007513 acids Chemical class 0.000 claims description 31
- 239000002904 solvent Substances 0.000 claims description 31
- -1 glycidyl ester Chemical class 0.000 claims description 28
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 26
- 239000007795 chemical reaction product Substances 0.000 claims description 26
- 239000008096 xylene Substances 0.000 claims description 26
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 21
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 19
- 239000011248 coating agent Substances 0.000 claims description 19
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 19
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 16
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 15
- 238000002844 melting Methods 0.000 claims description 15
- 230000008018 melting Effects 0.000 claims description 15
- 239000007787 solid Substances 0.000 claims description 15
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 12
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 claims description 10
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 10
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 7
- 239000000047 product Substances 0.000 claims description 7
- 230000032050 esterification Effects 0.000 claims description 6
- 238000005886 esterification reaction Methods 0.000 claims description 6
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 5
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 claims description 5
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229940102838 methylmethacrylate Drugs 0.000 claims 5
- 239000003505 polymerization initiator Substances 0.000 claims 3
- 238000006116 polymerization reaction Methods 0.000 claims 2
- MQMQIKFILCJRGL-UHFFFAOYSA-N C(O)C(NC1=NC(=NC(=N1)N(OC)OC)N(OC)OC)CO Chemical compound C(O)C(NC1=NC(=NC(=N1)N(OC)OC)N(OC)OC)CO MQMQIKFILCJRGL-UHFFFAOYSA-N 0.000 claims 1
- UPVQHMDPVGJSDU-UHFFFAOYSA-N [[4-amino-6-[hydroxymethyl(trimethoxymethyl)amino]-1,3,5-triazin-2-yl]-(hydroxymethyl)amino]methanol Chemical compound COC(OC)(OC)N(CO)C1=NC(N)=NC(N(CO)CO)=N1 UPVQHMDPVGJSDU-UHFFFAOYSA-N 0.000 claims 1
- 238000007334 copolymerization reaction Methods 0.000 claims 1
- 239000011230 binding agent Substances 0.000 abstract description 16
- 239000000049 pigment Substances 0.000 abstract description 11
- 238000001035 drying Methods 0.000 abstract description 4
- 229920000642 polymer Polymers 0.000 abstract description 4
- 238000007790 scraping Methods 0.000 abstract description 4
- 239000004745 nonwoven fabric Substances 0.000 abstract description 3
- 229910052799 carbon Inorganic materials 0.000 abstract description 2
- 239000003973 paint Substances 0.000 abstract description 2
- 235000013350 formula milk Nutrition 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 7
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 238000012545 processing Methods 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 229910000831 Steel Inorganic materials 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 238000004383 yellowing Methods 0.000 description 3
- 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
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- 241000905957 Channa melasoma Species 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N Methyl ethyl ketone Natural products CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- 239000005967 1,4-Dimethylnaphthalene Substances 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- FRQQKWGDKVGLFI-UHFFFAOYSA-N 2-methylundecane-2-thiol Chemical compound CCCCCCCCCC(C)(C)S FRQQKWGDKVGLFI-UHFFFAOYSA-N 0.000 description 1
- AOSPVUKRNAQARI-UHFFFAOYSA-N 2-n-(trimethoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COC(OC)(OC)NC1=NC(N)=NC(N)=N1 AOSPVUKRNAQARI-UHFFFAOYSA-N 0.000 description 1
- HCGFUIQPSOCUHI-UHFFFAOYSA-N 2-propan-2-yloxyethanol Chemical compound CC(C)OCCO HCGFUIQPSOCUHI-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- LJXPVOCJSZDFDA-UHFFFAOYSA-N 4-methylpentan-2-one;toluene Chemical compound CC(C)CC(C)=O.CC1=CC=CC=C1 LJXPVOCJSZDFDA-UHFFFAOYSA-N 0.000 description 1
- NKFIBMOQAPEKNZ-UHFFFAOYSA-N 5-amino-1h-indole-2-carboxylic acid Chemical compound NC1=CC=C2NC(C(O)=O)=CC2=C1 NKFIBMOQAPEKNZ-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- GNEQMRHYROMOAG-UHFFFAOYSA-N C(O)C(ON(C1=NC(=NC(=N1)NOC)N=C)OC)(CO)CO Chemical compound C(O)C(ON(C1=NC(=NC(=N1)NOC)N=C)OC)(CO)CO GNEQMRHYROMOAG-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102100024133 Coiled-coil domain-containing protein 50 Human genes 0.000 description 1
- 229920008712 Copo Polymers 0.000 description 1
- 239000001293 FEMA 3089 Substances 0.000 description 1
- 101000910772 Homo sapiens Coiled-coil domain-containing protein 50 Proteins 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 208000012641 Pigmentation disease Diseases 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000003700 epoxy group Chemical group 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
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 210000004905 finger nail Anatomy 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229940063557 methacrylate Drugs 0.000 description 1
- 229940063559 methacrylic acid Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000001038 titanium pigment Substances 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
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D125/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Coating compositions based on derivatives of such polymers
- C09D125/02—Homopolymers or copolymers of hydrocarbons
- C09D125/04—Homopolymers or copolymers of styrene
- C09D125/08—Copolymers of styrene
- C09D125/14—Copolymers of styrene with unsaturated esters
-
- 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
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
- C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/625—Polymers of alpha-beta ethylenically unsaturated carboxylic acids; hydrolyzed polymers of esters of these acids
- C08G18/6258—Polymers of alpha-beta ethylenically unsaturated carboxylic acids; hydrolyzed polymers of esters of these acids the acid groups being esterified with polyhydroxy compounds or epoxy compounds during or after polymerization
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyurethanes Or Polyureas (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2626900A DE2626900C2 (de) | 1976-06-16 | 1976-06-16 | Verfahren zur Herstellung von hydroxylgruppenenthaltenden Mischpolymerisaten |
| DEP2626900.1 | 1976-06-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1111191A true CA1111191A (en) | 1981-10-20 |
Family
ID=5980640
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA279,556A Expired CA1111191A (en) | 1976-06-16 | 1977-05-31 | Process for the manufacture of soluble copolymers which contain hydroxyl groups and can be crosslinked with organic polyisocyanates |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4145513A (ref) |
| JP (1) | JPS5349092A (ref) |
| BE (1) | BE851788A (ref) |
| CA (1) | CA1111191A (ref) |
| DE (1) | DE2626900C2 (ref) |
| FR (1) | FR2355035A1 (ref) |
| GB (1) | GB1583663A (ref) |
| IT (1) | IT1080653B (ref) |
| NL (1) | NL182148C (ref) |
| SE (1) | SE7706896L (ref) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2858096C2 (de) * | 1978-11-29 | 1985-04-04 | Synthopol Chemie Dr. rer. pol. Koch & Co, 2150 Buxtehude | Reaktionslacke und Einbrennlacke auf der Basis von hydroxylgruppentragenden Copolymerisaten sowie Verfahren zur Herstellung von Überzügen |
| DE2858105C2 (de) * | 1978-11-29 | 1985-03-28 | Synthopol Chemie Dr. rer. pol. Koch & Co, 2150 Buxtehude | Reaktionslacke und Einbrennlacke auf der Basis von hydroxylgruppentragenden Copolymerisaten sowie Verfahren zur Herstellung von Überzügen |
| DE2851613C2 (de) * | 1978-11-29 | 1983-04-28 | Synthopol Chemie Dr. rer. pol. Koch & Co, 2150 Buxtehude | Verfahren zur Herstellung von in organischen Lösungsmitteln löslichen hydroxylgruppentragenden Copolymerisaten |
| DE2851615C2 (de) * | 1978-11-29 | 1990-05-31 | Synthopol Chemie Dr. rer. pol. Koch & Co, 2150 Buxtehude | Verfahren zur Herstellung von in organischen Lösungsmitteln löslichen hydroxylgruppentragenden Copolymerisaten und deren Verwendung |
| DE2851614C2 (de) * | 1978-11-29 | 1983-06-01 | Synthopol Chemie Dr. rer. pol. Koch & Co, 2150 Buxtehude | Verfahren zur Herstellung von in organischen Lösungsmitteln löslichen hydroxylgruppentragenden Copolymerisaten |
| FR2452500A1 (fr) * | 1979-03-27 | 1980-10-24 | Corona Peintures | Copolymeres vinyliques hydroxyles solubles pour vernis et laques et procede de preparation |
| DE2942327A1 (de) * | 1979-10-19 | 1981-05-14 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von oh-gruppen enthaltenden copolymerisaten |
| DE3019959A1 (de) * | 1980-05-24 | 1981-12-03 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von hydroxylgruppenhaltigen copolymerisaten und deren verwendung |
| US4452948A (en) * | 1980-09-10 | 1984-06-05 | The International Paint Company Limited | Coating composition comprising a hydroxy component, an anhydride component and a catalyst |
| DE3036694A1 (de) * | 1980-09-29 | 1982-06-03 | Hoechst Ag, 6000 Frankfurt | Gummielastische, ethylenisch ungesaettigte polyurethane und dieselben enthaltendes durch strahlung polymerisierbares gemisch |
| DE3128062A1 (de) * | 1981-07-16 | 1983-02-03 | Hoechst Ag, 6000 Frankfurt | Waessrige copolymerisat-dispersionen, verfahren zu ihrer herstellung und verwendung der dispersionen |
| DE3226131A1 (de) * | 1982-07-13 | 1984-01-19 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von ueberzuegen |
| DE3322830A1 (de) * | 1983-06-24 | 1985-01-03 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von ueberzuegen |
| DE3322829A1 (de) * | 1983-06-24 | 1985-01-03 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von ueberzuegen |
| US4818796A (en) * | 1987-05-13 | 1989-04-04 | Ppg Industries, Inc. | Polymers prepared by polymerizing alpha, beta-ethylenically unsaturated acids and epoxy compounds |
| US4988766A (en) * | 1987-05-13 | 1991-01-29 | Ppg Industries, Inc. | Polymers prepared by polymerizing alpha, beta-ethylenically unsaturated acids and epoxy compounds and crosslinked products therefrom |
| US4798746A (en) * | 1987-08-24 | 1989-01-17 | Ppg Industries, Inc. | Basecoat/clearcoat method of coating utilizing an anhydride additive in the thermoplastic polymer-containing basecoat for improved repairability |
| US4798745A (en) * | 1987-08-24 | 1989-01-17 | Ppg Industries, Inc. | Non-yellowing coating composition based on a hydroxy component and an anhydride component and utilization in a process of coating |
| DE3740774A1 (de) * | 1987-12-02 | 1989-06-15 | Herberts Gmbh | Bindemittel, verfahren zu dessen herstellung und dessen verwendung in klaren oder pigmentierten ueberzugsmitteln |
| DK0408858T3 (da) * | 1989-05-19 | 1994-04-11 | Basf Corp | Copolymerer til anvendelse til overtræk med ringe indhold af flygtige organiske bestanddele og højt faststofindhold |
| US5135516A (en) * | 1989-12-15 | 1992-08-04 | Boston Scientific Corporation | Lubricious antithrombogenic catheters, guidewires and coatings |
| US5843089A (en) * | 1990-12-28 | 1998-12-01 | Boston Scientific Corporation | Stent lining |
| DE4326656A1 (de) * | 1993-08-09 | 1995-02-16 | Hoechst Ag | Hydroxylgruppen enthaltende Copolymerisate, ihre Herstellung und ihre Verwendung in festkörperreichen Beschichtungsmitteln |
| DE4442769A1 (de) * | 1994-12-01 | 1996-06-05 | Hoechst Ag | Niedermolekulare funktionelle Copolymerisate, Verfahen zu ihrer Herstellung und ihre Verwendung |
| DE19515919A1 (de) * | 1995-05-02 | 1996-11-07 | Hoechst Ag | Neue niedermolekulare OH-funktionelle Copolymerisate mit hoher Seitenkettenverzweigung, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
| DE19545634A1 (de) | 1995-12-07 | 1997-06-12 | Bayer Ag | Festkörperreiche Bindemittelkombinationen |
| DE19628444A1 (de) * | 1996-07-15 | 1998-01-22 | Bayer Ag | Neue festkörperreiche 2 K-PUR-Bindemittelkombinationen |
| US6136443A (en) | 1997-07-11 | 2000-10-24 | Ppg Industries Ohio, Inc. | Acid etch resistant film-forming compositions and composite coating compositions |
| US6458885B1 (en) | 1998-05-29 | 2002-10-01 | Ppg Industries Ohio, Inc. | Fast drying clear coat composition |
| DE19955129A1 (de) | 1999-11-17 | 2001-05-23 | Bayer Ag | Neue, festkörperreiche Bindemittelkombinationen und deren Verwendung |
| US6755824B2 (en) | 2002-04-15 | 2004-06-29 | Uab Research Foundation | Platelet inhibitor eluting ablation catheter |
| EP2574647A1 (en) | 2011-09-30 | 2013-04-03 | Cytec Austria GmbH | Aqueous coating compositions |
| EP2628755A1 (en) * | 2012-02-14 | 2013-08-21 | Cytec Technology Corp. | Aminoplast Crosslinker Resin Compositions, Process for their Preparation, and Method of Use |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3694415A (en) * | 1970-07-15 | 1972-09-26 | Kiyoshi Honda | Coating resinous composition |
| US3689308A (en) * | 1970-12-21 | 1972-09-05 | Ford Motor Co | Unsaturated polyester-hydroxy functional,graded-rubber paint and process |
| US3998768A (en) * | 1974-12-24 | 1976-12-21 | E. I. Du Pont De Nemours And Company | Thermosetting powder coating composition of a blend of acrylic polymers having different glass transition temperatures and a blocked polyisocyanate cross-linking agent |
-
1976
- 1976-06-16 DE DE2626900A patent/DE2626900C2/de not_active Expired
- 1976-12-09 NL NLAANVRAGE7613688,A patent/NL182148C/xx not_active IP Right Cessation
-
1977
- 1977-01-28 JP JP916277A patent/JPS5349092A/ja active Pending
- 1977-02-21 FR FR7704891A patent/FR2355035A1/fr active Granted
- 1977-02-24 BE BE175231A patent/BE851788A/xx not_active IP Right Cessation
- 1977-05-16 GB GB20474/77A patent/GB1583663A/en not_active Expired
- 1977-05-20 US US05/798,997 patent/US4145513A/en not_active Expired - Lifetime
- 1977-05-31 CA CA279,556A patent/CA1111191A/en not_active Expired
- 1977-06-15 IT IT24699/77A patent/IT1080653B/it active
- 1977-06-15 SE SE7706896A patent/SE7706896L/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7613688A (nl) | 1977-12-20 |
| BE851788A (fr) | 1977-06-16 |
| DE2626900B1 (de) | 1977-08-18 |
| US4145513A (en) | 1979-03-20 |
| NL182148C (nl) | 1988-01-18 |
| FR2355035A1 (fr) | 1978-01-13 |
| JPS5349092A (en) | 1978-05-04 |
| DE2626900C2 (de) | 1978-04-13 |
| SE7706896L (sv) | 1977-12-17 |
| NL182148B (nl) | 1987-08-17 |
| IT1080653B (it) | 1985-05-16 |
| GB1583663A (en) | 1981-01-28 |
| FR2355035B1 (ref) | 1982-03-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |