Phosphate ester-modified acrylic polyols

Patent metadata

Field	Value
Publication number	US-10711086-B2
Application number	US-201515517788-A
Country	US
Kind code	B2
Filing date	Oct 7, 2015
Priority date	Oct 8, 2014
Publication date	Jul 14, 2020
Grant date	Jul 14, 2020

Abstract

A composition includes a polyphosphoric acid-modified acrylic polyol, wherein the polyphosphoric acid-modified acrylic polyol has greater than zero, but less than 1.0 wt % modification with polyphosphoric acid.

First claim

What is claimed is:

1. A composition comprising a phosphate ester-modified acrylic polyol and a catalyst, wherein:
after addition of an isocyanate, the composition exhibits a longer pot-life than a composition comprising the reaction product of a non-phosphate ester-modified acrylic polyol;
the catalyst comprises an organotin, organobismuth, organozinc, a metal octoate, or a metal dionate catalyst, wherein the catalyst is present in an amount of from at least 0.06 pHS to about 0.12 pHS;
the phosphate ester-modified acrylic polyol comprises:
greater than zero, but less than 1.0 wt % phosphate modification, wherein the wt % is based on the total weight of the phosphate ester-modified acrylic polyol; and
(option 1) prior to phosphate modification, the phosphate ester-modified acrylic polyol comprises an acrylic polyol comprising polymerized monomers of:
an acrylic, methacrylic, or styrenic monomer, and
an allyl alcohol, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, or a mixture of two or more thereof; or

(option 2) prior to polymerization, the phosphate ester-modified acrylic polyol comprises:
an acrylic, methacrylic, or styrenic monomer and
a hydroxyethylmethacrylate-phosphate monomer;

wherein:
the acrylic, methacrylic, or styrenic monomer of (option 1) or (option 2) comprises acrylic acid, methacrylic acid, methyl methacrylate, ethyl acrylate, ethyl methacrylate, n-propyl acrylate, n-propyl methacrylate, n-butyl acrylate, n-butyl methacrylate, isopropyl acrylate, isopropyl methacrylate, isobutyl acrylate, isobutyl methacrylate, n-amyl acrylate, n-amyl methacrylate, n-hexyl acrylate, n-hexyl methacrylate, isoamyl acrylate, isoamyl methacrylate, trifluoroethyl acrylate, trifluoroethyl methacrylate, benzyl acrylate, benzyl methacrylate, 2-n-butoxyethyl acrylate, 2-n-butoxyethyl methacrylate, 2-chloroethyl acrylate, 2-chloroethyl methacrylate, sec-butyl acrylate, sec-butyl methacrylate, tert-butyl acrylate, tert-butyl methacrylate, 2-ethylbutyl acrylate, 2-ethylbutyl methacrylate, cinnamyl acrylate, cinnamyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate, cyclopentyl acrylate, cyclopentyl methacrylate, 2-ethoxyethyl acrylate, 2-ethoxyethyl methacrylate, furfuryl acrylate, furfuryl methacrylate, hexafluoroisopropyl acrylate, hexafluoroisopropyl methacrylate, 3-methoxybutyl acrylate, 3-methoxybutyl methacrylate, 2-methoxybutyl acrylate, 2-methoxybutyl methacrylate, 2-nitro-2-methylpropyl acrylate, 2-nitro-2-methylpropyl methacrylate, n-octyl-acrylate, n-octyl-methacrylate, 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, 2-phenoxyethyl acrylate, 2-phenoxyethyl methacrylate, 2-phenylethyl acrylate, 2-phenylethyl methacrylate, phenyl acrylate, phenyl methacrylate, propargyl acrylate, propargyl methacrylate, tetrahydrofurfuryl acrylate, tetrahydrofurfuryl methacrylate, tetrahydropyranyl acrylate, tetrahydropyranyl methacrylate, styrene, α-methylstyrene, or a mixture of any two or more thereof.

2. The composition of claim 1 , wherein the phosphate ester-modified acrylic polyol comprises greater than zero, but less than 0.5 wt % phosphate modification.

3. The composition of claim 2 , wherein the phosphate ester-modified acrylic polyol comprises greater than zero, but less than 0.3 wt % phosphate modification.

4. The composition of claim 3 , wherein the phosphate ester-modified acrylic polyol comprises greater than zero, but less than 0.2 wt % phosphate modification.

5. The composition of claim 1 , wherein the phosphate ester-modified acrylic polyol is the reaction product of the acrylic polyol (option 1) and X wt % polyphosphoric acid, based upon the acrylic polyol, wherein 0.01≤X≤1.0.

6. The composition of claim 5 , wherein the reaction product further comprises a residue of an initiator used in the reaction, and wherein the initiator was a dialkyl peroxide, an alkyl peroxy ester, or a free radical, azo-based initiator.

7. The composition of claim 1 further comprising the isocyanate and wherein the isocyanate comprises diphenyl diisocyanate, 1,6-hexamethylenediisocyanate, isophorone diisocyanate, a trimer of isophorone diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, methylene diphenyl diisocyanate, a polymeric methylene diphenyl diisocyanate, methylene bis-cyclohexyldiisocyanate, naphthalene diisocyanate, hydrogenated methylene diphenyl diisocyanate, a trimer of hexamethylenediisocyanate, an allophanate, a biuret, or a mixture of any two or more thereof.

8. The composition of claim 1 , wherein the catalyst comprises triphenylbismuth, dibutyltindilaurate, dibutyltindiacetate, dioctyltindilaurate, zinc octoate, tin ocoate, zirconium dionate, cobalt dionate, or a mixture of any two or more thereof.

9. The composition of claim 1 which exhibits improved adhesion when compared to a composition comprising the reaction product of a non-phosphate ester-modified acrylic polyol.

10. A two-component coating package comprising:
a first component comprising an isocyanate; and
a second component comprising a phosphate ester-modified acrylic polyol; and
a catalyst comprising an organotin, organobismuth, organozinc, a metal octoate, or a metal dionate catalyst, wherein the catalyst is present in an amount from about 0.06 pHS to about 0.12 pHS,
wherein:
after combining the first component and the second component, the two-component coating package exhibits a longer pot-life than a two-component coating package comprising the reaction product of a non-phosphate ester-modified acrylic polyol;
the phosphate ester-modified acrylic polyol comprises:
greater than zero, but less than 1.0 wt % phosphate modification, wherein the wt % is based on the total weight of the phosphate ester-modified acrylic polyol; and
(option 1) prior to phosphate modification, the phosphate ester-modified acrylic polyol comprises an acrylic polyol comprising polymerized monomers of:
an acrylic, methacrylic, or styrenic monomer, and
an allyl alcohol, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, or a mixture of two or more thereof; or

(option 2) prior to polymerization, the phosphate ester-modified acrylic polyol comprises:
an acrylic methacrylic, or styrenic monomer, and a hydroxyethylmethacrylate-phosphate monomer;

wherein:
the acrylic, methacrylic, or styrenic monomer of option 1 or option 2 comprises acrylic acid, methacrylic acid, methyl methacrylate, ethyl acrylate, ethyl methacrylate, n-propyl acrylate, n-propyl methacrylate, n-butyl acrylate, n-butyl methacrylate, isopropyl acrylate, isopropyl methacrylate, isobutyl acrylate, isobutyl methacrylate, n-amyl acrylate, n-amyl methacrylate, n-hexyl acrylate, n-hexyl methacrylate, isoamyl acrylate, isoamyl methacrylate, trifluoroethyl acrylate, trifluoroethyl methacrylate, benzyl acrylate, benzyl methacrylate, 2-n-butoxyethyl acrylate, 2-n-butoxyethyl methacrylate, 2-chloroethyl acrylate, 2-chloroethyl methacrylate, sec-butyl acrylate, sec-butyl methacrylate, tert-butyl acrylate, tert-butyl methacrylate, 2-ethylbutyl acrylate, 2-ethylbutyl methacrylate, cinnamyl acrylate, cinnamyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate, cyclopentyl acrylate, cyclopentyl methacrylate, 2-ethoxyethyl acrylate, 2-ethoxyethyl methacrylate, furfuryl acrylate, furfuryl methacrylate, hexafluoroisopropyl acrylate, hexafluoroisopropyl methacrylate, 3-methoxybutyl acrylate, 3-methoxybutyl methacrylate, 2-methoxybutyl acrylate, 2-methoxybutyl methacrylate, 2-nitro-2-methylpropyl acrylate, 2-nitro-2-methylpropyl methacrylate, n-octyl-acrylate, n-octyl-methacrylate, 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, 2-phenoxyethyl acrylate, 2-phenoxyethyl

Assignees

• Basf Se

Inventors

• Calhoun Eric
• Klots Timothy

Classifications

• C09D185/02

  containing phosphorus · CPC title

• C08F230/02

  containing phosphorus · CPC title

• C09D143/02

  Homopolymers or copolymers of monomers containing phosphorus · CPC title

• C08G18/792

  formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates · CPC title

• C08G79/02 Primary

  a linkage containing phosphorus · CPC title