MONOBENZOATE ANALOGS USEFUL AS PLASTICIZERS IN PLASTISOL COMPOSITIONS

• US 20200131332A1
• Filed: 12/23/2019
• Published: 04/30/2020
• Est. Priority Date: 09/26/2014
• Status: Active Grant

• Current Assignee: Emerald Kalama Chemical, LLC (Lanxess AG)
• Original Assignee: Emerald Kalama Chemical, LLC (Lanxess AG)
• Inventors: MCBRIDE, Emily, ROTH, Steven D., ANDREWS, Jerry, ARENDT, William D.
• Granted Patent: US 10,995,198 B2
• Time in Patent Office: Days
• CPC Class Codes: C08K 5/0016 Plasticisers
• CPC Class Codes: C08K 5/101 of monocarboxylic acids
• CPC Class Codes: C08K 5/12 of cyclic polycarboxylic acids
• CPC Class Codes: C08L 27/06 Homopolymers or copolymers of vinyl chloride
• CPC Class Codes: C08L 33/08 Homopolymers or copolymers of acrylic acid esters
• CPC Class Codes: C08L 33/10 Homopolymers or copolymers of methacrylic acid esters

Abstract

Unique 3-PPB monobenzoate analogs useful as plasticizers in polymeric dispersions, such as plastisols, melt compounds, and adhesives among other applications. The analogs are structurally similar to and/or derived from 3-phenylpropyl benzoate and heretofore were not known for use in industrial applications, particularly not as a plasticizer in polymeric applications including without limitation plastisols and adhesives. Depending on the application, the advantages rendered by the use of the inventive monobenzoate analogs include, among other things, excellent solvating properties and rheology, low viscosity and significantly improved viscosity over time, comparable or improved Tg suppression, set and open times, as well as health, safety and environmental advantages, over traditional plasticizers.

Claims

1. A plastisol composition comprising:

polymer particles dispersed in a plasticizer, wherein the plasticizer contains a primary plasticizer and at least one other plasticizer comprising;

2-methyl-3-phenylpropyl benzoate, 2-phenylethyl 2-phenylacetate, benzyl 3-phenylpropanoate, or benzyl 2-methyl-3-phenyl-propanoate, present in amounts ranging from about 2 to about 20 parts per 100 parts by weight of the polymer particles.

2. The plastisol of claim 1, wherein the polymer comprises polyvinyl chloride homopolymers or copolymers or an acrylic-based polymer.

3. The plastisol of claim 2, wherein the acrylic-based polymer comprises polyalkyl methacrylates, aromatic methacrylates, alkyl acrylates, acrylic acids, or styrenated acrylics.

4. The plastisol composition of claim 1, wherein the total plasticizer content of the plastisol ranges from 20 parts to 80 parts by weight of the polymer particles and wherein the amounts of 2-methyl-3-phenylpropyl benzoate, 2-phenylethyl 2-phenylacetate, benzyl 3-phenylpropanoate, or benzyl 2-methyl-3-phenyl-propanoate range from about 5% to about 20% of the total plasticizer content.

5. The plastisol composition of claim 1, wherein the primary plasticizer comprises a phthalate ester, a phosphate ester, an adipate, an azelate, an oleate, a succinate, a sebacate, a citrate, a trimellitate, a terephthalate ester, a 1,2-cyclohexane dicarboxylate ester, an epoxy plasticizer, a fatty acid ester, a glycol derivative, a sulfonamide, a sulfonic acid ester, a dibenzoate, a bioplasticizer, a chloroparaffin, a polyester, a hydrocarbon, a hydrocarbon derivative, or mixtures thereof.

6. The plastisol composition of claim 1, wherein the plasticizer is further blended with another plasticizer comprising isononyl benzoate, isodecyl benzoate, 2-ethylhexyl benzoate, 2,2,4-trimethyl-1,3-pentanediol diisobutyrate, epoxidized soybean oil, PG disoyate, PG monosoyate, or mixtures thereof.

7. The plastisol of claim 1, wherein the plasticizer is further blended with a solid plasticizer that is sucrose benzoate, dicyclohexyl phthalate, triphenyl phosphate, glycerol tribenzoate, 1,4-cyclohexane dimethanol (CHDM) dibenzoate, pentaerythritol tetrabenzoate, an alkyl glycol ester, or mixtures thereof.

8. A plastisol composition comprising:

(a) polymer particles dispersed in a plasticizer; and

(b) a plasticizer comprising;

(i) at least one plasticizer comprising a phthalate, a 1,2-cyclohexane dicarboxylate, or a dibenzoate plasticizer, or mixtures thereof, and,

(ii) at least one other plasticizer comprising;

2-methyl-3-phenylpropyl benzoate, 2-phenylethyl 2-phenylacetate, benzyl 3-phenylpropanoate, or benzyl 2-methyl-3-phenyl-propanoate,

wherein the total plasticizer content of the plastisol ranges from about 20 to about 80 parts per one hundred parts by weight of polymer particles, and

wherein the 2-methyl-3-phenylpropyl benzoate, 2-phenylethyl 2-phenylacetate, benzyl 3-phenylpropanoate, or benzyl 2-methyl-3-phenyl-propanoate are present in amounts ranging from about 5% to about 20% of the total plasticizer content.