IP Library Granted Patent US 10,513,595
Granted Patent B2
US 10,513,595 · App. 15/510,880 · Granted Dec 24, 2019

Monobenzoate analogs useful as plasticizers in plastisol compositions

Inventors: William D. Arendt (Libertyville, IL); Emily McBride (Kalama, WA); Steven D. Roth (Ridgefield, WA); Jerry Andrews (Woodland, WA)
Assignee: EMERALD KALAMA CHEMICAL, LLC
C08K5/101C09J11/06C09J123/0853C09J131/04C08K5/0016C08K2201/019C09J2205/102C09J2423/04C09J2431/00
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Quick Facts
Patent No.
US 10,513,595
App. No.
15/510,880
Granted
Dec 24, 2019
Kind
B2
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. 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 (15)

1. A plastisol composition comprising polymer particles dispersed in a plasticizer, wherein the plasticizer for dispersing the polymer particles consists of 2-methyl-3-phenylpropyl benzoate, 2-phenylethyl 2-phenylacetate, benzyl 3-phenylpropanoate, or benzyl 2-methyl-3-phenylpropanoate

present in amounts ranging from about 20 parts to about 80 parts per 100 parts by weight of the polymer particles, wherein the plasticizer maintains viscosity stability over time.

2. The plastisol composition of claim 1 , further comprising another plasticizer that is 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 benzoate, a bioplasticizer, a chloroparaffin, a polyester, a hydrocarbon, a hydrocarbon derivative, or mixtures thereof.

3. The plastisol composition of claim 1 , further comprising any of 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.

4. The plastisol composition of claim 1 , further comprising 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.

5. A plastisol composition comprising:

polymer particles dispersed in a plasticizer, wherein the polymer comprises polyvinyl chloride, a polyvinyl chloride copolymer or an acrylic-based polymer;

wherein the plasticizer for dispersing the polymer particles consists of 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 20 parts to about 80 parts per 100 parts by weight of the polymer,

wherein the plasticizer is used alone as a primary plasticizer or as a secondary plasticizer in combination with other plasticizers, and

wherein the plasticizer maintains viscosity stability over time.

6. The plastisol of claim 5 , wherein the acrylic-based polymer comprises polyalkyl methacrylates, aromatic methacrylates, alkyl acrylates, acrylic acids, or styrenated acrylics.

7. The plastisol of claim 5 wherein the plasticizer is present in amounts of about 70 parts per hundred parts by weight of the polymer.

8. An adhesive composition comprising:

a. a polymeric emulsion comprising polyvinyl acetate or vinyl acetate ethylene; and

b. a plasticizer selected from the group consisting of 2-methyl-3-phenylpropyl benzoate, 2-phenylethyl 2-phenylacetate, benzyl 3-phenylpropanoate or benzyl 2-methyl-3-phenylpropanoate, present in amounts ranging from about 1 to about 20%, wet.

Assignments (3)
RELEASE OF SECURITY INTEREST IN PATENTS RECORDED AT R/F 053495/0016 Recorded Aug 3, 2021
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
To: EMERALD KALAMA CHEMICAL, LLC
Reel/Frame 057177/0982 →
SECURITY INTEREST Recorded Aug 14, 2020
From: KALAMA CHEMICAL, LLC
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
Reel/Frame 053495/0016 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 13, 2017
From: ARENDT, WILLIAM D.; MCBRIDE, EMILY; ROTH, STEVEN D.; ANDREWS, JERRY
To: EMERALD KALAMA CHEMICAL, LLC
Reel/Frame 041559/0763 →
Continuity (2)
Provisional Application 62056109 · Sep 26, 2014
Related Publication 20170253725A1 · Sep 7, 2017