Monobenzoate analogs useful as plasticizers in plastisol compositions

• US 10,513,595 B2
• Filed: 09/25/2015
• Issued: 12/24/2019
• 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: Arendt, William D., McBride, Emily, Roth, Steven D., Andrews, Jerry
• Primary Examiner(s): Brooks, Kregg T
• Application Number:
  US15/510,880
• Publication Number:
  US 20170253725A1
• Time in Patent Office: 1,551 Days
• CPC Class Codes: C08K 2201/019 the composition being defined by the absence of a certain additive
• CPC Class Codes: C08K 5/0016 Plasticisers
• CPC Class Codes: C08K 5/101 of monocarboxylic acids
• CPC Class Codes: C08L 23/0853 Vinylacetate
• CPC Class Codes: C08L 27/06 Homopolymers or copolymers of vinyl chloride
• CPC Class Codes: C08L 31/04 Homopolymers or copolymers of vinyl acetate
• CPC Class Codes: C08L 33/00 Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
• CPC Class Codes: C09J 11/06 organic
• CPC Class Codes: C09J 123/0853 Vinylacetate
• CPC Class Codes: C09J 131/04 Homopolymers or copolymers of vinyl acetate
• CPC Class Codes: C09J 2301/408 additives as essential feature of the adhesive layer
• CPC Class Codes: C09J 2423/04 Presence of homo or copolymers of ethene
• CPC Class Codes: C09J 2431/00 Presence of polyvinyl acetate

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

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.