CA1067233A - Methode de fabrication d'emails a base d'eau, sans agent tensio-actif - Google Patents

Methode de fabrication d'emails a base d'eau, sans agent tensio-actif

Info

Publication number: CA1067233A
Authority: CA; Canada
Prior art keywords: water; polymer; parts; solution; weight
Prior art date: 1974-06-03
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

CA251,359A

Other languages

English (en)

Inventor

Mo-Fung Cheung

Ray A. Dickie

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.)

Ford Motor Company of Canada Ltd

Original Assignee

Ford Motor Company of Canada Ltd

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.)

1974-06-03

Filing date

1976-04-28

Publication date

1979-11-27

1974-06-03 Priority claimed from US476115A external-priority patent/US3926888A/en

1975-05-30 Priority claimed from CA228,423A external-priority patent/CA1071789A/fr

1976-04-28 Application filed by Ford Motor Company of Canada Ltd filed Critical Ford Motor Company of Canada Ltd

1976-04-28 Priority to CA251,359A priority Critical patent/CA1067233A/fr

1979-11-27 Application granted granted Critical

1979-11-27 Publication of CA1067233A publication Critical patent/CA1067233A/fr

Status Expired legal-status Critical Current

Links

XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 92
238000004519 manufacturing process Methods 0.000 title claims abstract description 4
210000003298 dental enamel Anatomy 0.000 title abstract description 18
229920000642 polymer Polymers 0.000 claims abstract description 151
239000003973 paint Substances 0.000 claims abstract description 60
239000000178 monomer Substances 0.000 claims abstract description 54
239000000203 mixture Substances 0.000 claims abstract description 48
150000001412 amines Chemical class 0.000 claims abstract description 34
239000003381 stabilizer Substances 0.000 claims abstract description 34
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 20
229920001577 copolymer Polymers 0.000 claims abstract description 20
239000003431 cross linking reagent Substances 0.000 claims abstract description 16
229920003180 amino resin Polymers 0.000 claims abstract description 14
239000000243 solution Substances 0.000 claims description 92
238000000034 method Methods 0.000 claims description 43
239000004908 Emulsion polymer Substances 0.000 claims description 36
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
239000003960 organic solvent Substances 0.000 claims description 17
239000006185 dispersion Substances 0.000 claims description 11
239000008346 aqueous phase Substances 0.000 claims description 9
239000000839 emulsion Substances 0.000 claims description 9
239000007864 aqueous solution Substances 0.000 claims description 8
229920001002 functional polymer Polymers 0.000 claims description 6
229920000877 Melamine resin Polymers 0.000 claims description 5
229920001807 Urea-formaldehyde Polymers 0.000 claims description 3
230000006872 improvement Effects 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
239000004094 surface-active agent Substances 0.000 abstract description 14
230000015572 biosynthetic process Effects 0.000 abstract description 6
230000035945 sensitivity Effects 0.000 abstract description 3
230000008030 elimination Effects 0.000 abstract description 2
238000003379 elimination reaction Methods 0.000 abstract description 2
230000000087 stabilizing effect Effects 0.000 abstract description 2
229920000126 latex Polymers 0.000 description 46
239000000463 material Substances 0.000 description 45
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ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 32
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 22
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CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 19
238000007720 emulsion polymerization reaction Methods 0.000 description 19
238000002360 preparation method Methods 0.000 description 19
-1 e.g. Chemical compound 0.000 description 18
238000009472 formulation Methods 0.000 description 17
229910001870 ammonium persulfate Inorganic materials 0.000 description 16
238000006116 polymerization reaction Methods 0.000 description 16
239000000376 reactant Substances 0.000 description 15
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 13
239000012986 chain transfer agent Substances 0.000 description 13
239000002904 solvent Substances 0.000 description 13
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239000003999 initiator Substances 0.000 description 12
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SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 10
238000000576 coating method Methods 0.000 description 10
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GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 8
239000002585 base Substances 0.000 description 8
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 8
229920005989 resin Polymers 0.000 description 8
239000011347 resin Substances 0.000 description 8
GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 7
229920003270 Cymel® Polymers 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
125000004356 hydroxy functional group Chemical group O* 0.000 description 7
239000000049 pigment Substances 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
239000000470 constituent Substances 0.000 description 6
238000010992 reflux Methods 0.000 description 6
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
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VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 5
150000001408 amides Chemical group 0.000 description 5
239000012736 aqueous medium Substances 0.000 description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000011248 coating agent Substances 0.000 description 5
239000006184 cosolvent Substances 0.000 description 5
239000003995 emulsifying agent Substances 0.000 description 5
239000003505 polymerization initiator Substances 0.000 description 5
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 4
229910000831 Steel Inorganic materials 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
235000020354 squash Nutrition 0.000 description 4
239000010959 steel Substances 0.000 description 4
239000002562 thickening agent Substances 0.000 description 4
239000004408 titanium dioxide Substances 0.000 description 4
POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
150000005215 alkyl ethers Chemical class 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000008199 coating composition Substances 0.000 description 3
229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 3
XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 3
229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000000945 filler Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
230000002209 hydrophobic effect Effects 0.000 description 3
239000007788 liquid Substances 0.000 description 3
DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 description 3
JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000012429 reaction media Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
229920003169 water-soluble polymer Polymers 0.000 description 3
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
ZRKMQKLGEQPLNS-UHFFFAOYSA-N 1-Pentanethiol Chemical compound CCCCCS ZRKMQKLGEQPLNS-UHFFFAOYSA-N 0.000 description 2
FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 2
PRFSAQZQEVZPEZ-UHFFFAOYSA-N 2-(hydroxymethyl)-n-(2-methylpropoxy)prop-2-enamide Chemical compound CC(C)CONC(=O)C(=C)CO PRFSAQZQEVZPEZ-UHFFFAOYSA-N 0.000 description 2
LUOPFCDZQGKIDO-UHFFFAOYSA-N 2-(hydroxymethyl)prop-2-enamide Chemical class NC(=O)C(=C)CO LUOPFCDZQGKIDO-UHFFFAOYSA-N 0.000 description 2
GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
BNCADMBVWNPPIZ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COCN(COC)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 BNCADMBVWNPPIZ-UHFFFAOYSA-N 0.000 description 2
QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 2
PBMWEQHOZPTUQQ-UHFFFAOYSA-N 4-hydroxy-2-methylbut-2-enamide Chemical class NC(=O)C(C)=CCO PBMWEQHOZPTUQQ-UHFFFAOYSA-N 0.000 description 2
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
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229910019142 PO4 Inorganic materials 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
239000004721 Polyphenylene oxide Chemical group 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
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239000003377 acid catalyst Substances 0.000 description 2
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230000003213 activating effect Effects 0.000 description 2
238000013019 agitation Methods 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229910052936 alkali metal sulfate Inorganic materials 0.000 description 2
238000000498 ball milling Methods 0.000 description 2
230000008901 benefit Effects 0.000 description 2
WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
UZILCZKGXMQEQR-UHFFFAOYSA-N decyl-Benzene Chemical compound CCCCCCCCCCC1=CC=CC=C1 UZILCZKGXMQEQR-UHFFFAOYSA-N 0.000 description 2
238000009826 distribution Methods 0.000 description 2
WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000011790 ferrous sulphate Substances 0.000 description 2
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238000000227 grinding Methods 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 2
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
238000003801 milling Methods 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 2
235000021317 phosphate Nutrition 0.000 description 2
230000000704 physical effect Effects 0.000 description 2
229920000570 polyether Chemical group 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
230000008569 process Effects 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
238000006479 redox reaction Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000004576 sand Substances 0.000 description 2
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
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HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical compound CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 0.000 description 1
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 1
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229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 1
XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 1
229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 1
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
ZACVGCNKGYYQHA-UHFFFAOYSA-N 2-ethylhexoxycarbonyloxy 2-ethylhexyl carbonate Chemical compound CCCCC(CC)COC(=O)OOC(=O)OCC(CC)CCCC ZACVGCNKGYYQHA-UHFFFAOYSA-N 0.000 description 1
WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
FEWFXBUNENSNBQ-UHFFFAOYSA-N 2-hydroxyacrylic acid Chemical class OC(=C)C(O)=O FEWFXBUNENSNBQ-UHFFFAOYSA-N 0.000 description 1
RPBWMJBZQXCSFW-UHFFFAOYSA-N 2-methylpropanoyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(=O)C(C)C RPBWMJBZQXCSFW-UHFFFAOYSA-N 0.000 description 1
SEILKFZTLVMHRR-UHFFFAOYSA-N 2-phosphonooxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOP(O)(O)=O SEILKFZTLVMHRR-UHFFFAOYSA-N 0.000 description 1
DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 1
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NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
239000004342 Benzoyl peroxide Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
239000004640 Melamine resin Substances 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
229930040373 Paraformaldehyde Natural products 0.000 description 1
KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
239000003945 anionic surfactant Substances 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
BUMBHRYBYOQTFV-UHFFFAOYSA-N butyl prop-2-enoate;ethyl prop-2-enoate Chemical compound CCOC(=O)C=C.CCCCOC(=O)C=C BUMBHRYBYOQTFV-UHFFFAOYSA-N 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
230000008859 change Effects 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
BSVQJWUUZCXSOL-UHFFFAOYSA-N cyclohexylsulfonyl ethaneperoxoate Chemical compound CC(=O)OOS(=O)(=O)C1CCCCC1 BSVQJWUUZCXSOL-UHFFFAOYSA-N 0.000 description 1
229960002887 deanol Drugs 0.000 description 1
XJOBOFWTZOKMOH-UHFFFAOYSA-N decanoyl decaneperoxoate Chemical compound CCCCCCCCCC(=O)OOC(=O)CCCCCCCCC XJOBOFWTZOKMOH-UHFFFAOYSA-N 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
239000012972 dimethylethanolamine Substances 0.000 description 1
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
229940043264 dodecyl sulfate Drugs 0.000 description 1
KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000013020 final formulation Substances 0.000 description 1
229960004279 formaldehyde Drugs 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
230000009477 glass transition Effects 0.000 description 1
LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 1
LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229940102253 isopropanolamine Drugs 0.000 description 1
150000004668 long chain fatty acids Chemical class 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
150000007974 melamines Chemical class 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
238000010944 pre-mature reactiony Methods 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
238000007665 sagging Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
238000002791 soaking Methods 0.000 description 1
RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
238000005507 spraying Methods 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 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
229910052719 titanium Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
229910001428 transition metal ion Inorganic materials 0.000 description 1
238000005292 vacuum distillation Methods 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

Landscapes

Paints Or Removers (AREA)

CA251,359A 1974-06-03 1976-04-28 Methode de fabrication d'emails a base d'eau, sans agent tensio-actif Expired CA1067233A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA251,359A CA1067233A (fr)	1974-06-03	1976-04-28	Methode de fabrication d'emails a base d'eau, sans agent tensio-actif

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US476115A US3926888A (en)	1974-06-03	1974-06-03	Method of making aqueous coating compositions of acrylic polymer latex, acrylic polymer solution, aminoplast and acrylic stabilizer polymer
CA228,423A CA1071789A (fr)	1974-06-03	1975-05-30	Methode pour produire un email a base aqueuse, exempt de solvant
CA251,359A CA1067233A (fr)	1974-06-03	1976-04-28	Methode de fabrication d'emails a base d'eau, sans agent tensio-actif

Publications (1)

Publication Number	Publication Date
CA1067233A true CA1067233A (fr)	1979-11-27

Family

ID=27163984

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA251,359A Expired CA1067233A (fr)	1974-06-03	1976-04-28	Methode de fabrication d'emails a base d'eau, sans agent tensio-actif

Country Status (1)

Country	Link
CA (1)	CA1067233A (fr)

1976
- 1976-04-28 CA CA251,359A patent/CA1067233A/fr not_active Expired

Publication	Publication Date	Title
US3919154A (en)	1975-11-11	Aqueous coating composition of acrylic polymer latex, acrylic polymer solution and aminoplast and method of making
US3926888A (en)	1975-12-16	Method of making aqueous coating compositions of acrylic polymer latex, acrylic polymer solution, aminoplast and acrylic stabilizer polymer
US3928273A (en)	1975-12-23	Method of making organic solvent free aqueous coating compositions of acrylic polymer latex, water soluble emulsion-polymerized acrylic polymer, and aminoplast
US4062823A (en)	1977-12-13	Hybrid water-based enamels with partially crosslinked latexes
US4151143A (en)	1979-04-24	Surfactant-free polymer emulsion coating composition and method for preparing same
US9012027B2 (en)	2015-04-21	Aqueous emulsion
US3953643A (en)	1976-04-27	Method for coating and product
US4487859A (en)	1984-12-11	Self-curing water dispersed polymers
US5266361A (en)	1993-11-30	Preparation of a multilayer coating
US4740546A (en)	1988-04-26	Aqueous dispersion of vinyl copolymer resin
US4304701A (en)	1981-12-08	Aqueous acrylic polymer dispersions
US4215028A (en)	1980-07-29	Thermosetting resin, and its production and use
US20070244238A1 (en)	2007-10-18	Polymer dispersions, process for the preparation thereof and the use thereof
US4329266A (en)	1982-05-11	Water-dispersed coating composition comprising an acrylic graft polymer containing carboxyl groups, hydroxyl and/or amide groups
USRE31936E (en)	1985-07-02	Dispersing paint pigments
CA1071789A (fr)	1980-02-12	Methode pour produire un email a base aqueuse, exempt de solvant
GB1574721A (en)	1980-09-10	Process for preparing aqueous copolymer emulsions
JPH0224310A (ja)	1990-01-26	尿素基を含有し且つエチレン性不飽和単量体を基礎とする分散物重合体、その製造方法およびその用途
EP1294816A1 (fr)	2003-03-26	Composition de liant aqueuse
JPH0678497B2 (ja)	1994-10-05	水性塗料組成物
CA1203034A (fr)	1986-04-08	Resilles cationiques pour l'emploi en thermoplastique thermodurcissement
US6218456B1 (en)	2001-04-17	Anticorrosion binders comprising phosphate or phosphonate groups
EP0103118A1 (fr)	1984-03-21	Couche d'impression intermédiaire à teneur en solides élevée basée sur t-butyl acrylate et styrène
CA1067233A (fr)	1979-11-27	Methode de fabrication d'emails a base d'eau, sans agent tensio-actif
JPS6411674B2 (fr)	1989-02-27