IP Library Granted Patent US 10,995,198
Granted Patent B2
US 10,995,198 · App. 16/725,574 · Granted May 4, 2021

Monobenzoate analogs useful as plasticizers in plastisol compositions

Inventors: Emily McBride (Kalama, WA); Steven D. Roth (Ridgefield, WA); Jerry Andrews (Woodland, WA); William D. Arendt (Libertyville, IL)
Assignee: Emerald Kalama Chemical, LLC
C08K5/101C08K5/12C08L27/06C08L33/08C08L33/10
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Quick Facts
Patent No.
US 10,995,198
App. No.
16/725,574
Granted
May 4, 2021
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 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 (13)

1. A plastisol composition comprising: polymer particles dispersed in a plasticizer, wherein the plasticizer contains a primary plasticizer and at least one other plasticizer consisting 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 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 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.

5. 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.

6. 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.

7. 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.

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 Jan 16, 2020
From: MCBRIDE, EMILY; ARENDT, WILLIAM D.; ROTH, STEVEN D.; ANDREWS, JERRY
To: EMERALD KALAMA CHEMICAL, LLC
Reel/Frame 051537/0082 →
Continuity (3)
Continuation In Part 15510880
Provisional Application 62056109 · Sep 26, 2014
Related Publication 20200131332A1 · Apr 30, 2020