Overbased barium complexes of C8 to C10 carboxylic acids

Details Overbased barium complexes of C8 to C10 carboxylic acids Overbased barium complexes of C8 to C10 carboxylic acids

2001-12-06

2003-09-02

McAvoy, Ellen M. (Department: 1764)

Solid anti-friction devices, materials therefor, lubricant or se

Lubricants or separants for moving solid surfaces and...

Organic -co- compound

C524S385000, C524S394000, C524S400000, C524S424000, C106S218000

Reexamination Certificate

active

06613723

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to overbased barium complexes of an isomeric mixture of branched C
8
to C
10
carboxylic acids. More particularly, the present invention relates to overbased barium complexes of an isomeric mixture of branched C
8
carboxylic acids.
2. Description of the Prior Art
U.S. Pat. No. 2,510,035 (Mack) discloses a heat and light stabilized polyvinyl chloride resin containing a stabilizer. The stabilizer includes an alkali earth metal salt of a substituted chain aliphatic carboxylic acid containing from 4 to 16 carbon atoms. However, the stabilizer is a salt, not an overbased barium complex derived from an isomeric mixture of from about C
8
to about C
10
branched carboxylic acids and an isomeric mixture of from about C
10
to about C
15
alcohols.
U.S. Pat. No. 3,147,232 (Norman et al.) describes stabilizers for vinyl chlorides polymers. The stabilizers include a mixture of alcohols, aliphatic monocarboxylic acid having from 12 to 20 carbon atoms and alkaline earth metal compounds such as barium oxide and barium hydroxide. The stabilizer is not derived from an isomeric mixture of from about C
8
to about C
10
branched carboxylic acids.
U.S. Pat. No. 3,194,823 (Le Suer et al.) discloses a process for preparing barium and cadmium containing organic complexes including mixing a monohydric alcohol, aliphatic acid and a metallic base. The aliphatic acid is oleic acid, not an isomeric mixture of from about C
8
to about C
10
branched carboxylic acids.
U.S. Pat. No. 3,274,135 (Norman et al.) discloses barium-cadmium organic complexes as stabilizers for halogen-containing resins. The complex is made by a process including preparing a mixture of an alcohol, such as aliphatic alcohol, an aliphatic monocarboxylic acid compound selected from the group consisting of aliphatic monocarboxylic acids and the barium and cadmium salts thereof, a barium base and a cadmium base. The complexes of the present invention do not have cadmium.
U.S. Pat. No. 3,417,039 (Penneck) teaches stabilizing compositions for chlorine containing polymer. The composition includes metal salts of organic acid containing from 4 to 18 carbon atoms, a polyhydric alcohol containing from 4 to 36 carbon atoms and an organic sulfur bearing compound. The metal can be barium. The complexes of the present invention do not have polyhydric alcohols nor do they have sulfur bearing compounds.
U.S. Pat. No. 4,123,399 (Gay) relates to a stabilizer from PVC including a mixed salt complex, polyol, a beta-diketone and a plasticizer. The complexes of the present invention do not have polyols or a beta-diketones.
U.S. Pat. No. 4,251,451 (Magee et al.) describes a process for producing a mixture of branched and linear carboxylic acid salts. The process includes reacting a mixture of branched and linear alcohols with a caustic of the formula M(OH)
n
to produce a reaction mixture containing carboxylic acid salts of the formula (RCOO)
n
M. M can be barium. R is selected from linear alkyl and branched alkyl groups having up to 19 carbon atoms. This process is a process for producing a mixture of branched and linear carboxylic acid salts, not a process for producing an overbased barium complex derived from an isomeric mixture of from about C
8
to about C
10
branched carboxylic acids and an isomeric mixture of from about C
10
to about C
15
alcohols.
U.S. Pat. No. 4,776,947 (Streck et al.) mentions isotridecanol as placticizer for PVC. The isotridecanol is not part of an overbased barium complex.
U.S. Pat. No. 5,147,917 (Sugarwara et al.) discloses a halogenated resin composition including an overbased alkaline earth metal carboxylate/carbonate complex together with a beta-diketone compound or a metal salt thereof. The overbased alkaline earth metal carboxylate/carbonate can be represented by the following formula: R
2
M
x
CO
3
wherein R includes residue of 2-ethylhexylic acid and M is Ba. The complex is not an overbased barium complex having isotridecanol.
U.S. Pat. No. 5,322,872 (Quinn) relates to compositions of mixed carboxylates used as stabilizers for polymers. The compositions contain barium salt of a carboxylic acid having at least 6 atoms and an oxime complexing agent. The complexes of the present invention do not have an oxime complexing agent.
U.S. Pat. No. 5,830,832 (Benda et al.) describes high basicity calcium carboxylates obtained by carbonating a mixture of branched chain oxo-acids, such as, Cekanoic® acids, and excess calcium in the presence of a volatile solvent. The carboxylates can be used in paints, as lubricants and fuel additives. The overbased barium complexes of the present invention do not have calcium.
U.S. Pat. No. 5,830,935 (Khattar et al.) describes a process for producing light colored basic alkali and alkaline earth metal salts by reacting a basic alkali earth metal compound, an alkyl phenol and/or a carboxylic acid and carbon dioxide to form a reaction product and thereafter post treating the reaction product with a liquid glycidyl ester having a C
7
-C
7
alkyl group to improve color. The compositions described in this patent are light colored basic alkali and alkaline earth metal salts, not complexes, and are derived from oleic acid and phenols, such as, nonyl- and dodecyl phenol.
U.S. Pat. No. 5,859,267 (Khattar et al.) describes the preparation and use of a 34% Ba complex. The barium is stabilized into a liquid by reacting barium hydroxide with a carboxylic acid, such as, oleic acid, and by reacting the resulting mixture with CO
2
in the presence of linear alcohols and nonylphenol. The compositions described in this patent are also derived from oleic acid and nonylphenol. The number of equivalents of carboxylic acid is significantly lower than the number of equivalents of barium, and the unneutralized barium is present as a carbonate formed in situ and stabilized by nonylphenol and alcohol. Nonylphenol is an environmentally toxic material and such products are usually viscous and highly colored and, as a result, when used as additives to polyvinyl chloride polymers, they can impart unwanted color to the polymers, and as such, should be avoided.
None of the above references describe overbased low color products that are suitable for use in stabilizing polyvinyl chloride without the need for a decolorization step.
Accordingly, the present invention provides a highly overbased barium complex of a branched C
8
to C
10
carboxylic acid that has low color and which can be used to stabilize polyvinyl chloride polymers without the need for a decolorization step.
SUMMARY OF THE INVENTION
The present invention provides a process for preparing an overbased barium complex. The process includes the steps of:
heating a mixture of barium hydroxide monohydrate and an isomeric mixture of from about C
10
to about C
15
alcohols in the presence of a solvent, thereby producing a first mixture;
contacting the first mixture and an isomeric mixture of from about C
8
to about C
10
branched carboxylic acids, thereby producing a second mixture which includes unreacted barium hydroxide; and
contacting the second mixture and carbon dioxide, thereby producing the overbased barium complex;
with the proviso that when the barium concentration in the overbased barium complex is 25 wt. % or more, the isomeric mixture of C
8
to about C
10
branched carboxylic acids is substantially free of 2-ethylhexanoic acid.
The isomeric mixture of C
8
to C
10
branched carboxylic acids is preferably an isomeric mixture of C
8
branched carboxylic acids (e.g., Cekanoic® 8 acid, available from ExxonMobil Chemical Company).
The present invention also provides an overbased barium complex prepared by a process which includes the steps of:
heating a mixture of barium hydroxide monohydrate and an isomeric mixture of from about C
10
to about C
15
alcohols in the presence of a solvent, thereby producing a first mixture;
contacting the first mixture and an isomeric mixture of from about C
8
to about C
10
branched carboxylic acids, thereby producing a second mixture which

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