Compositions: coating or plastic – Coating or plastic compositions – O-containing organic compound
Reexamination Certificate
1999-06-24
2001-05-15
Lambkin, Deborah C. (Department: 1626)
Compositions: coating or plastic
Coating or plastic compositions
O-containing organic compound
C106S211100, C162S158000, C162S168100, C162S169000, C162S175000, C162S179000, C549S255000
Reexamination Certificate
active
06231659
ABSTRACT:
BACKGROUND
Heretofore, certain alkenyl succinic anhydrides have been developed for use as paper sizing agents. If the ultimate treated paper is for indirect food usage, regulations in the United States require that 95 wt % of the olefins used in forming the alkenyl succinic anhydride must be in the C
16
to C
20
range. One typical commercial product sold for such use is an alkenyl succinic anhydride in which the alkenyl group is derived from a mixture of internal olefins composed on a weight basis of approximately 4% C
14
, 50% C
16
, 45.5% C
18
, and 0.5% C
20
olefins. This olefin mixture is also used as a component of certain drilling fluids. Another commercially used mixture of alkenyl succinic anhydrides is formed from an internal olefin mixture consisting essentially of C
16
and C
18
olefins.
Various other alkenyl succinic anhydrides have been proposed for use as paper sizing agents. See, for example, U.S. Pat. Nos. 3,102,064; 3,821,069; 4,431,826; 4,576,680; 5,114,538; and 5,246,491; EP published application 0 169 250 A1; and Japan Kokai 57-154495.
Commercial processes for producing olefins typically produce a range of olefins of differing molecular weights. Use of distillation enables the resultant gross mixtures of olefins to be divided into various carbon number fractions to thereby provide olefins for specified end use applications. Typically C
6
and C
8
olefins find commercial application as comonomers in the manufacture of olefin polymers. C
8
and C
10
olefins are used in the production of synthetic lubricants, while C
12
olefins are very useful in the manufacture of synthetic household detergents and surface active agents. And as noted above, olefin mixtures highly enriched in C
16
and C
18
olefins are of commercial utility as raw materials for the synthesis of paper sizing agents and as components of drilling fluids.
It would be of considerable benefit if new, useful olefin mixtures could be developed that would make possible more efficient utilization of olefins for which relatively small utilities currently exist. If this could be accomplished, current market demands for olefins could continue to be efficiently served by present and projected manufacturing facilities while at the same time making more efficient use of hydrocarbon feedstocks to such facilities and product outputs from such facilities.
This invention is deemed to make possible the fulfillment of the foregoing objective.
SUMMARY OF THE INVENTION
Pursuant to this invention there are provided both new sizing agents and new olefin mixtures useful in producing such sizing agents. More particularly, one embodiment of this invention makes it possible to provide new sizing agents with properties rendering them useful in the manufacture of a variety of products, such as paper, cardboard, wall board, gypsum board, and like materials. In another of its embodiments this invention provides new olefin mixtures which are especially adapted for use as raw materials for the manufacture of such sizing agents. Moreover, other potential applications exist for various new compositions of this invention.
Thus, in accordance with one of its embodiments this invention provides a mixture of alkenyl succinic anhydrides in which the alkenyl groups have in the range of about 6 to about 40 carbon atoms, and in which at least 97 wt % (preferably at least 98 wt %) of the alkenyl groups are bifurcated on the alpha carbon atom into two branches neither of which has less than two carbon atoms, said mixture being further characterized in that:
A) from about 20 to about 50% of the alkenyl succinic anhydrides that are bifurcated on the alpha carbon atom, have only one methyl or methylene group thereon, and the remainder of the alkenyl succinic anhydrides that are bifurcated on the alpha carbon atom have two straight chain branches emanating from the alpha carbon atom;
B) the alkenyl succinic anhydrides present in the mixture are composed of at least 3 (and preferably at least 4) alkenyl succinic anhydrides that differ from each other in the number of carbon atoms in the respective alkenyl groups, each of these at least 3 (or preferably at least 4) alkenyl succinic anhydrides being present in said mixture in an amount of at least 5 wt % based on the total weight of said mixture of alkenyl succinic anhydrides;
C) the alkenyl succinic anhydrides present in the mixture contain no more than about 50 wt % (preferably no more than about 40 wt %) based on the total weight of the alkenyl succinic anhydrides, of any specific alkenyl succinic anhydride;
D) the alkenyl succinic anhydrides present in the mixture contain no more than about 50 wt % (preferably no more than about 40 wt %) based on the total weight of the alkenyl succinic anhydrides, of any two or more alkenyl succinic anhydride isomers having the same number of carbon atoms in their alkenyl groups;
E) the alkenyl succinic anhydrides present in the mixture are proportioned such that the average number of carbon atoms in the alkenyl groups thereof is in the range of about 16 to about 22 (preferably in the range of about 16 to about 20) carbon atoms per molecule; and
F) the mixture of alkenyl succinic anhydrides has a viscosity at 25° C. in the range of about 80 to about 220 centistokes.
Such mixtures can be formed by reaction of the appropriate mixture of olefins with maleic anhydride at a suitable temperature at which the so-called “ene” reaction occurs (e.g., 250° C.). The mixture of olefins used to make the alkenyl succinic anhydrides (and thus the alkenyl groups of the mixture of alkenyl succinic anhydrides produced) can have odd numbers of carbon atoms or even numbers of carbon atoms, or can be mixtures of odd and even numbered olefins and alkenyl groups. Alkenyl succinic anhydrides produced from olefin mixtures in which all olefin components, or substantially all olefin components (e.g., at least about 95 wt % of the olefins) are even numbered olefins, are preferred.
Alternatively, the alkenyl succinic anhydrides mixtures of this invention can be prepared by blending together in appropriate proportions two or more preformed alkenyl succinic anhydrides in which the alkenyl groups differ from each other such that the resultant blend conforms to the requirements of the mixtures of this invention.
Mixtures of alkenyl succinic anhydrides as described above wherein the components thereof have in the range of about 12 to about 30 carbon atoms in their respective alkenyl groups are preferred. More preferred are mixtures of alkenyl succinic anhydrides as described above wherein the components thereof have in the range of about 14 to about 26 carbon atoms. Mixtures of alkenyl succinic anhydrides as described above wherein the mixture contains, if any, no more than a total of about 50 wt % (and even more preferably no more than about 10 wt %) of alkenyl succinic anhydrides in which the alkenyl groups contain 16, 17 or 18 carbon atoms are particularly preferred from the cost-effectiveness standpoint. In fact, it has been found possible to effectively utilize mixtures of alkenyl succinic anhydrides which are essentially devoid of alkenyl groups containing 15, 16, 17, 18, or 19 carbon atoms, i.e., such mixtures contain, if any, no more than trace amounts, say 2% at most, of alkenyl groups containing 15 to 19 carbon atoms.
Preferably, the mixtures of alkenyl succinic anhydrides of this invention are further characterized in that at least about 70 wt % of the alkenyl groups have the olefinic double bond in the two or higher position.
The various mixtures described above can be in admixture with relatively small amounts of one or more saturated aliphatic hydrocarbons. The amount of such saturated aliphatic hydrocarbon content, when present, will typically be up to about 5 wt % (more usually up to about 2 wt %) based on the total weight of the alkenyl succinic anhydrides and the saturated aliphatic hydrocarbon(s) present in the composition.
Particularly preferred is a mixture of alkenyl succinic anhydrides as described above wherein (1) from about 20 to about 80 wt % of the alkenyl s
Free Michelle R.
Goins Dixie E.
Hu Patrick C.
Legloahec Valerie N.
Albemarle Corporation
Lambkin Deborah C.
Pippenger Phillip M.
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