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US3355403A Expired / Lapsed US ⏱️ 0.0 years remaining

Solvent solution of water-insoluble salts of alpha, beta-ethylenically unsaturated carboxylic adducts with fatty acid esters of allyl alcohol-vinyl aromatic copolymers

Assignee: Monsanto Co
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Filing: 1964-12-14
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Granted: 1967-11-28
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Expires: 1984-12-14
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Abstract

Abstract A coating composition comprises a solution of an alkali metal, ammonium or amine salt of an adduct of (a) up to a stoichiometric proportion of an a ,b -ethylenically unsaturated monoor poly-carboxylic acid, an anhydride thereof or a partial ester of such a polycarboxylic acid and (b) an ester of (i) a copolymer of styrene, a substituted styrene or a mixture thereof and allyl alcohol or a substituted allyl alcohol or a mixture thereof and (ii) 0.75 to 1.25 carboxyl equivalents of an ethylenically unsaturated fatty acid or of a mixture of fatty acids with or without non-fatty monobasic acids, said acid or acid mixture having an iodine number of 50 to 220, per hydroxyl equivalent of said copolymer, in a solvent comprising (c) 60 to 90 parts by weight of water and (d) 40 to 10 parts by weight of an ether alcohol <FORM:1124938/C3/1> in which one R is hydrogen and the other is n-propyl or n-butyl, or a mixture of such ether alcohols. Preferably, a styrene/allyl alcohol copolymer containing 5 to 8% by weight of hydroxyl groups is employed. The adduction is preferably carried out in the presence of iodine and an inert organic solvent. The solvent (d) may be present in admixture with other solvents. In the various examples, a maleinized or fumarized adduct of the soya fatty acid ester of a styrene/allyl alcohol copolymer is mixed with dimethylethanolamine, water and sodium hydroxide and then there is added (i) water and 1 - (n - propoxy) - propan - 2 - ol and 2 - (n-propoxy) - propan - 1 - ol or (ii) 2 - (n - propoxy)-propan - 1 - ol, water and 1 - n - butoxyethoxy-2-propanol or (iii) water and 1-(n-propoxy)-propan-2-ol or (iv) butoxyethoxyethanol, 1 - (n - butoxy) - propan - 2 - ol and 2 - (n-butoxy)-propan-1-ol and water or (v) 1-(n-butoxy)-propan-2-ol and water or (vi) 2-(n-butoxy)-propan-1-ol.ALSO:Steel panels are coated with gloss enamel formulations containing as an essential component a solution of an alkali metal, ammonium or amine salt of an adduct of (a) up to a stoichiometric proportion of an a , b -ethylenically unsaturated mono- or poly-carboxylic acid, an anhydride thereof or a partial ester of such a polycarboxylic acid and (b) an ester of (i) a copolymer of styrene, a substituted styrene or a mixture thereof and allyl alcohol or a substituted allyl alcohol or a mixture thereof and (ii) 0.75 to 1.25 carboxyl equivalents of an ethylenically unsaturated fatty acid or of a mixture of fatty acids with or without non-fatty monobasic acids, said acid or acid mixture having an iodine number of 50 to 220, per hydroxyl equivalent of said copolymer, in a solvent comprising (c) 60 to 90 parts by weight of water and (d) 40 to 10 parts by weight of an ether alcohol <FORM:1124938/B1-B2/1> in which one R is hydrogen and the other is n-propyl or n-butyl, or a mixture of such ether alcohols. The acid or mixture of acids of component (ii) has an iodine number of 50 to 200 (ASTM D1467-57T). The adduction is preferably carried out in the presence of iodine and an inert organic solvent. The solvent (d) may be present in admixture with other solvents and from 10 to 100 parts by weight of the salt of the adduct are preferably employed per 100 parts of (c) and (d). In the examples, the sodium and dimethyl ethanolamine salts of a maleinized or fumarized adduct of the soya fatty acid ester of a styrene/allyl alcohol copolymer are mixed with water and one or more of the ether alcohols 2-(n-propoxy)-propan-1-ol 2-(n-butoxy)-propan-1-ol; 1-(n-propoxy)-propan-2-ol and 1-(n-butoxy)-propan-2-ol. Other solvents may also be added. To form the gloss enamel formulations rutile titanium dioxide pigment, optionally talc powder, a solution of a cobalt compound and a calcium-containing drier are added to the salts of the adducts. The coating applied to the steel panels is 0.001" thick.

Inventors

  • 👤 Frank J Hahn

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-03 13:29
CPC Classifications
C; C09; C09D; C09D155/00; C09D155/04; C08; C08F; C08F8/00; C08F8/14; C09D151/00; C09D151/003; C08F2810/00; C08F2810/30

Claims Analysis

Total Claims: 2
Claim 1
Independent Claim 193 words
A COATING COMPOSITON COMPRISING: (A) FROM 10 TO 100 PARTS BY WEIGHT OF A WATER-INSOLUBLE SALT OF AN ADDUCT OF (1) AN ALPHA,BETA-ETHYLENICALLY UNSATURATED CARBOXYLIC COMPOUND AND (2) A FATTY ACID ESTER OF A COPOLYMER OF A STRRENE MONOMER AND AN ALLYL ALCOHOL MONOMER HAVING THE STRUCTURE OF A CO-REACTION PRODUCT OF (A) FROM 0.75 TO 1.25 CARBOXYL EQUIVALENTS OF FATTY ACID AND MIXTURES THEREOF HAVING AN IODINE UNSATURATION NUMBER BY THE ASTM D1467-27T TEST METHOD OF FROM ABOUT 50 TO 220 AND (B) 1.0 HYDROXYL EQUIVALENTS OF A COPOLYMER OF A STYRENE MONOMER AND AN ALLYL ALCOHOL MONOMER, AND (B) 100 PARTS BY WEIGHT OF A SOLVENT MIXTURE COMPRISING (1) FROM 60 TO 90 PARTS BY WEIGHT OF WATER AND (2), CORRESPONDINGLY, FROM 40 TO 10 PARTS BY WEIGHT OF AN ORGANIC COSOLVENT SELECTED FROM THE CLASS CONSISTING OF 2-(N-PROPOXY)-PROPAN-1-OL, 2-(N-BUTOXY)-PROPAN-1-OL, 1-(N-PROPOXY)PROPAN-2-OL, 1-(NBUTOXY)-PROPAN-2-OL, AND MIXTURES THEREOF, SAID STYRENE MONOMER BEING SELECTED FROM THE GROUP CONSISTING OF STYRENE, ALPHA-ALKYL STYRENES, RING-SUBSTITUTED ALKYL STYRENES, ALPHA-ALKYL RING-SUBSTITUTED ALKYL STYRENES, HALO-STYRENES, HALOALKYL STYRENES, AND MIXTURES THEREOF; SAID ALLYL ALCOHOL MONOMER BEING SELECTED FROM THE GROUP CONSISTING OF ALLYL ALCOHOL, METHALLYL ALCOHOL, CHLORALLYL ALCOHOL, AND MIXTURES THEREOF.
Claim 2
Dependent Claim 193 words
A COATING COMPOSITON COMPRISING: (A) FROM 10 TO 100 PARTS BY WEIGHT OF A WATER-INSOLUBLE SALT OF AN ADDUCT OF (1) AN ALPHA,BETA-ETHYLENICALLY UNSATURATED CARBOXYLIC COMPOUND AND (2) A FATTY ACID ESTER OF A COPOLYMER OF A STRRENE MONOMER AND AN ALLYL ALCOHOL MONOMER HAVING THE STRUCTURE OF A CO-REACTION PRODUCT OF (A) FROM 0.75 TO 1.25 CARBOXYL EQUIVALENTS OF FATTY ACID AND MIXTURES THEREOF HAVING AN IODINE UNSATURATION NUMBER BY THE ASTM D1467-27T TEST METHOD OF FROM ABOUT 50 TO 220 AND (B) 1.0 HYDROXYL EQUIVALENTS OF A COPOLYMER OF A STYRENE MONOMER AND AN ALLYL ALCOHOL MONOMER, AND (B) 100 PARTS BY WEIGHT OF A SOLVENT MIXTURE COMPRISING (1) FROM 60 TO 90 PARTS BY WEIGHT OF WATER AND (2), CORRESPONDINGLY, FROM 40 TO 10 PARTS BY WEIGHT OF AN ORGANIC COSOLVENT SELECTED FROM THE CLASS CONSISTING OF 2-(N-PROPOXY)-PROPAN-1-OL, 2-(N-BUTOXY)-PROPAN-1-OL, 1-(N-PROPOXY)PROPAN-2-OL, 1-(NBUTOXY)-PROPAN-2-OL, AND MIXTURES THEREOF, SAID STYRENE MONOMER BEING SELECTED FROM THE GROUP CONSISTING OF STYRENE, ALPHA-ALKYL STYRENES, RING-SUBSTITUTED ALKYL STYRENES, ALPHA-ALKYL RING-SUBSTITUTED ALKYL STYRENES, HALO-STYRENES, HALOALKYL STYRENES, AND MIXTURES THEREOF; SAID ALLYL ALCOHOL MONOMER BEING SELECTED FROM THE GROUP CONSISTING OF ALLYL ALCOHOL, METHALLYL ALCOHOL, CHLORALLYL ALCOHOL, AND MIXTURES THEREOF.

References Cited (Backward Citations)

US3251790A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1970-11-27 1971-05-29 1971-11-28 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1974-11-27 1975-05-29 1975-11-28 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1978-11-27 1979-05-29 1979-11-28 $7700.00 Window Closed / Lapsed

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