Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From carboxylic acid or derivative thereof
Reexamination Certificate
1999-06-24
2001-05-01
Hampton-Hightower, P. (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From carboxylic acid or derivative thereof
C528S342000, C528S345000, C528S363000, C525S418000, C525S419000, C525S420000, C525S422000, C524S600000, C524S602000, C162S158000, C162S164100, C162S164600, C162S168100, C162S168200, C162S175000, C162S180000, C162S181800, C162S184000, C162S185000, C162S202000, C162S205000
Reexamination Certificate
active
06225437
ABSTRACT:
BACKGROUND
It has been proposed heretofore to use certain imide-containing compounds or certain imide-containing polymers as sizing agents for paper and similar products. However, two other types of sizing agents have achieved widespread commercial acceptance in the marketplace for this use. These are certain alkenyl ketene dimers, and certain alkenyl succinic anhydrides such as 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.
Among the excellent properties of the alkenyl succinic anhydride paper sizing agents such as that described above are that it has high reactivity toward cellulose, and that it imparts an antiskidding property to sized papers. Unfortunately the anhydride is reactive to water and this can detract somewhat from realization of the full potential of sizing effectiveness inherent in the product.
It would be of considerable benefit if new, non-polymeric sizing agents could be found that have higher hydrolytic stability than alkenyl succinic anhydride paper sizing agents, and that possess beneficial performance capabilities as paper sizing agents. In addition, it would be of advantage to find paper sizing agents that are equally efficacious when used either as internal sizing agents or external sizing agents.
This invention is deemed to fulfill the foregoing objectives.
SUMMARY OF THE INVENTION
Pursuant to this invention there are provided new sizing agents for cellulosic products with properties rendering them useful in the manufacture of a variety of products, such as paper, cardboard, wall board, gypsum board, and like materials. Moreover, other potential applications exist for various new compositions of this invention.
Thus, in accordance with one of its embodiments, this invention provides one or a mixture of alkenyl and/or alkyl succinimides formed from one or a mixture of alkenyl or alkyl succinic anhydrides and at least one aliphatic amine having one or two primary amino groups in the molecule, said alkenyl and/or alkyl succinimide being characterized in that:
a) each alkenyl or alkyl group of such succinimide contains in the range of about 12 to about 30 carbon atoms, and is bifurcated on its alpha carbon atom into two branches neither of which contains less than 2 carbon atoms, one such branch being free of any side chain, and the other such branch either being free of any side chain or containing at most one methyl or methylene side chain; and
b) the succinimide has a viscosity at 80° C. of less than about 100 centistokes.
Preferred aliphatic amines used in forming the above succinimide(s) are alkyl or alkenyl primary monoamines, alpha omega alkylene diamines, alkylene polyamines having two terminal primary amino groups and at least one internal secondary amino group, and alkylene polyamines having one terminal primary amino group and at least one secondary or tertiary amino group.
The succinimides of this invention can be composed of one single compound meeting the above requirements, or they can be a mixture of two or more compounds meeting the above requirements. When the succinimides of this invention are in the form of a mixture, the mixture can differ in various respects. In one embodiment, the mixture can differ only in the chain lengths of the alkenyl and/or alkyl groups in the respective molecules. In another embodiment the mixture can be made from a mixture of two or more species of one type of amine (e.g., a mixture of, say, C
16
and C
18
alkyl or alkenyl monoamines, or a mixture of, say, ethylene diamine and hexamethylene diamine, or a mixture of, say, diethylene triamine, triethylene tetramine, and tetraethylene pentamine). In still another embodiment the mixture can be made from a mixture of at least two different types of amines (e.g., a mixture, say, of a monoamine and a polyamine, or a mixture of an alkylene polyamine and a polyalkylene polyamine).
In a preferred embodiment the succinimides of this invention comprise at least one alkenyl or alkyl succinimide in which (i) there are from 1 to 2 imidized alkenyl or alkyl succinic moieties per molecule, (ii) the alkenyl or alkyl group of each such moiety contains in the range of about 12 to about 30 carbon atoms, (iii) each such alkenyl or alkyl group is bifurcated on its alpha carbon atom into two branches neither of which contains less than 2 carbon atoms, one such branch being free of any side chain, and the other such branch either being free of any side chain or containing at most one methyl or methylene side chain, (iv) the imidizing moiety of the succinimide has one of the formulas (1) through (5) as follows:
>N—R
1
(1)
>N—C
2
H
4
NH(C
2
H
4
NH)
n
R
2
(2)
>N—R
3
—NH
2
(3)
>N—C
2
H
4
NH(C
2
H
4
NH)
n
C
2
H
4
—N< (4)
>N—R
3
—N< (5)
where R
1
is (a) an alkyl group or (b) an olefinically unsaturated aliphatic hydrocarbon group having therein from 1 to 3 olefinic double bonds, said group (a) or (b) having in the range of 2 to about 20 (preferably 4 to about 18) carbon atoms, R
2
is a hydrogen atom or an alkyl group, n is an integer in the range of 0 to 5, and R
2
has a total number of carbon atoms in the range of 2 to about 15, and R
3
is an alkylene group having from 2 to about 10 carbon atoms, and (v) the succinimide has a viscosity at 80° C. of less than about 100 centistokes. Of these succinimides, those in which the imidizing moiety is of Formula (1) are preferred. Also preferred are those of which the imidizing moiety is of Formula (4).
In one preferred embodiment the succinimide(s) described above is one or a mixture of such compounds which is a solid at room temperature (e.g., in the range of about 20 to about 25° C.) and which has a melting temperature in the range of about 30 to about 100° C.
The succinimides of this invention can be formed by reaction of the appropriate internal olefin or mixture of appropriate internal olefins with maleic anhydride at a suitable temperature at which the so-called “ene” reaction occurs (e.g., 250° C.). The resultant alkenyl succinic anhydride is then reacted with a suitable amine or mixture of amines to produce the succinimide. Such a reaction is sometimes referred to as an “imidization reaction”. To produce the corresponding alkyl succinimide(s), either the alkenyl succinic anhydride(s) or the alkenyl succinimide(s) is/are subjected to hydrogenation under a pressurized hydrogen atmosphere in the presence of a suitable catalyst such as palladium on charcoal.
The olefin(s) used to make the alkenyl succinic anhydride(s), and thus the alkenyl group(s) of both the alkenyl succinic anhydride(s) and the alkenyl succinimide(s), can have odd numbers of carbon atoms or even numbers of carbon atoms, or can be mixtures of odd and even numbers of carbon atoms. Alkenyl succinimides ultimately 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.
Individual alkenyl or alkyl succinimides meeting the above requirements and which have in the range of about 14 to about 26 carbon atoms in the alkenyl or alkyl group are preferred. Particularly preferred are individual alkenyl or alkyl succinimide that meet these requirements and have in the range of about 16 to about 22 carbon atoms in the alkenyl or alkyl group.
Mixtures of alkenyl and/or alkyl succinimides as described above wherein the components thereof have in the range of about 12 to about 30 carbon atoms in their respective alkenyl and/or alkyl groups, and that have an average number of carbon atoms in the range of about 14 to about 26 are preferred. More preferred are mixtures of alkenyl and/or alkyl succinimides as described above wherein the components thereof have in the range of about 12 to about 30 carbon atoms in their respective alkenyl and/or alkyl groups, and that have an average number of carbon atoms in the range of about
Hu Patrick C.
Legloahec Valerie N.
Albemarle Corporation
Hampton-Hightower P.
Pippenger Philip M.
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