# US 10,370,518 B2 · Plasticizer blends of ketal compounds

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- Number: US 10,370,518 B2
- Document ID: US10370518B2
- Status: Granted
- Kind: B2
- Application number: 15/389,745
- Filed: 2016-12-23
- Published: 2017-04-13
- Granted: 2019-08-06
- Earliest claimed: 2014-01-30
- Assignees: Gfbiochemicals IP Assets B.V.
- Applicants: GFBiochemicals Limited
- Inventors: Dorie J. Yontz; Friederike Stollmaier; Kevin J. Bechtold
- Web page: https://patentgrep.com/patent/US10370518B2

## CPC

- C08K 5/1575: Six-membered rings
- C08J 3/18: Plasticising macromolecular compounds (plasticisers C08K)
- C08K 5/12: of cyclic polycarboxylic acids
- C08K 5/1565: Five-membered rings
- C08J 2327/06: Homopolymers or copolymers of vinyl chloride
- C08K 5/0016: {Plasticisers}
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)

## Abstract

The present invention is directed to formulations including a polymer and a plasticizer composition. The plasticizer composition is a blend of an alkyl ketal ester plasticizer and a second plasticizer selected from a cycloaliphatic compound, an ortho phthalate compound, a terephthalate compound, a benzoate ester compound, and a bio-based compound. The plasticizer composition is at least 10% by weight of the total of the polymer and the plasticizer composition.

## Claims

### Claim 1

A formulation comprising:
a polymer; and
a plasticizer composition wherein the plasticizer composition comprises a blend of
i) a first compound having a structure corresponding to Structure (Ib)
and
ii) a second compound selected from an ortho phthalate compound, a terephthalate compound, a benzoate ester compound, or a bio-based compound; wherein the plasticizer composition is at least 10% by weight of the total of the polymer and the plasticizer composition.

### Claim 2 (depends on 1)

The formulation of claim 1, wherein the second compound is an ortho phthalate compound.

### Claim 3 (depends on 2)

The formulation of claim 2, wherein the ortho phthalate compound has the structure (V):

### Claim 4 (depends on 2)

The formulation of claim 2, wherein the ortho phthalate compound has the structure (III):

### Claim 5 (depends on 1)

The formulation of claim 1, wherein the second compound is a terephthalate compound.

### Claim 6 (depends on 5)

The formulation of claim 5, wherein the terephthalate compound has the structure (VI):

### Claim 7 (depends on 1)

The formulation of claim 1, wherein the second compound is a benzoate ester compound having the structure (IV):

### Claim 8 (depends on 1)

The formulation of claim 1, wherein the polymer is selected from a poly(vinyl chloride), polyhydroxyalkanoate, a poly(lactic acid), a polystyrene, a polyurethane, a polyurea, a polyurea-urethane, a polycarbonate, an acrylic polymer, a styrene-acrylic polymer, a vinyl-acrylic polymer, an ethylene-vinyl acetate polymer, a polyester, a polyamide, a polyether, a polybutadiene, an acrylonitrile-butadiene-styrene copolymer, a styrene-butadiene-styrene copolymer, a polyvinyl acetate, an elastomer, or homopolymers thereof, or random, graft, or block copolymers thereof, or blends or mixtures thereof.

### Claim 9 (depends on 1)

The formulation of claim 1, wherein the polymer comprises a poly(vinyl chloride).

### Claim 10 (depends on 1)

The formulation of claim 1, wherein the formulation is a plastisol.

### Claim 11 (depends on 1)

The formulation of claim 1, wherein the formulation is a dry blend.

### Claim 12 (depends on 1)

The formulation of claim 1, further comprising one or more additives selected from crosslinkers, adjuvants, colorants, antifouling agents, tougheners, solvents, fillers, metal particulates, odor scavenging agents, lubricants, thermal stabilizers, light stabilizers including UV stabilizers, flame retardant additives, pigments, blowing agents, processing aids, impact modifiers, coalescing solvents, antioxidants or a combination of any two or more thereof.

### Claim 13 (depends on 1)

An article comprising the formulation of claim 1.

### Claim 14 (depends on 1)

A process for plasticizing a polymer, the process comprising mixing a polymer and a plasticizing amount of the plasticizer composition of claim 1.

### Claim 15

A plastisol formulation comprising:
an organic polymer; and
a plasticizer composition, wherein the plasticizer composition comprises a blend of
i)
a compound having the Structure (Ib):
and
ii) a second compound selected from
a compound having any of the structures (III-VI):
wherein the plasticizer composition comprises from 1 to 90% of the combined weights of the plasticizer composition and the polymer.

### Claim 16 (depends on 15)

The plastisol formulation of claim 15, wherein the second compound is