IP Library Granted Patent US 9,725,573
Granted Patent B2
US 9,725,573 · App. 14/291,660 · Granted Aug 8, 2017

Monobenzoate useful as a plasticizer in plastisol compositions

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Quick Facts
Patent No.
US 9,725,573
App. No.
14/291,660
Granted
Aug 8, 2017
Kind
B2
Abstract

A unique monobenzoate useful as a plasticizer in polymeric dispersions, such as plastisols and melt compounds. The monobenzoate comprises 3-phenyl propyl benzoate, a benzoate ester heretofore known as a flavoring and fragrance agent, but not previously utilized as a plasticizer in polymeric applications. Depending on the application, the advantages rendered by the use of the inventive monobenzoate include, among other things, excellent solvating properties, low viscosity, viscosity stability, and improved rheology, as well as health, safety and environmental advantages over traditional plasticizers. The monobenzoate may be used alone or in combination with a variety of plasticizers, including but not limited to phthalates, terephthalates, dibenzoates, other monobenzoates, or 1,2-cyclohexane dicarboxylate esters, and mixtures thereof.

Claims (15)

1. A plastisol composition comprising:

a. a polyvinyl chloride (PVC)-based or an acrylic-based polymer dispersion wherein the acrylic-based polymer is a homopolymer or copolymer of polymethacrylate, aromatic methacrylates, alkylacrylates, or acrylic acid; and

b. a plasticizer consisting of 3-phenylpropyl benzoate, wherein the plasticizer provides improved solvation and rheology characteristics and improved gel/fusion temperatures over that achieved with other known high solvating plasticizers used in plastisols.

2. A plasticizer blend for use in plastisol compositions consisting of:

3-phenyl propyl benzoate,

diisononyl-1,2-cyclohexane dicarboxylate, and

a dibenzoate triblend comprising 20 wt. % of 1,2-propylene glycol dibenzoate and 80 wt % of a 4:1 diethylene glycol dibenzoate:dipropylene glycol dibenzoate.

3. The plasticizer blend of claim 2 , wherein the plastisol composition comprises a polyvinyl chloride polymer dispersed in the plasticizer blend.

4. A plasticizer blend for use in plastisol compositions consisting of:

3-phenyl propyl benzoate,

di-2-ethylhexyl terephthalate, and

a dibenzoate triblend comprising 20 wt % of 1,2-propylene glycol dibenzoate and 80 wt. % of a 4:1 diethylene glycol dibenzoate:dipropylene glycol dibenzoate.

5. The plasticizer blend of claim 4 , wherein the plastisol composition comprises a polyvinyl chloride polymer dispersed in the plasticizer blend.

6. A method of plasticizing a polyvinyl chloride (PVC) based-plastisol or an acrylic based-plastisol, comprising the step of:

adding 3-phenylpropyl benzoate to a primary plasticizer selected from the group consisting of di-2-ethylhexyl terephthalate, diisononyl-1,2-cyclohexane dicarboxylate, a dibenzoate triblend comprising 20 wt. % of 1,2-propylene glycol dibenzoate and 80 wt. % of a 4:1 diethylene glycol dibenzoate:dipropylene glycol dibenzoate, and mixtures thereof, wherein the PVC-based plastisol comprises a homopolymer or copolymer of polyvinyl chloride, and wherein the acrylic-based plastisol comprises a homopolymer or copolymer of polymethacrylates, aromatic methacrylates, alkylacrylates, or acrylic acid.

Assignments (7)
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 →
RELEASE OF SECURITY INTEREST IN PATENTS - FIRST LIEN Recorded Aug 14, 2020
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
To: EMERALD KALAMA CHEMICAL, LLC
Reel/Frame 053495/0827 →
RELEASE OF SECURITY INTEREST IN PATENTS - SECOND LIEN Recorded Aug 14, 2020
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
To: EMERALD KALAMA CHEMICAL, LLC
Reel/Frame 053495/0921 →
SECOND LIEN PATENT SECURITY AGREEMENT Recorded Aug 5, 2014
From: EMERALD KALAMA CHEMICAL, LLC
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
Reel/Frame 033472/0738 →
FIRST LIEN PATENT SECURITY AGREEMENT Recorded Aug 5, 2014
From: EMERALD KALAMA CHEMICAL, LLC
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
Reel/Frame 033472/0747 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 30, 2014
From: ARENDT, WILLIAM D.; MCBRIDE, EMILY
To: EMERALD KALAMA CHEMICAL, LLC
Reel/Frame 032997/0613 →