Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
2000-06-16
2003-04-15
Richter, Johann (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C570S101000, C570S181000
Reexamination Certificate
active
06548705
ABSTRACT:
FIELD OF THE INVENTION
The invention is in the chemical arts. It relates to organic chemistry and, more particularly, to organic compounds.
BRIEF SUMMARY OF THE INVENTION
The invention comprises an organic compound having a nonpolar portion bonded to a polar portion.
The nonpolar portion for the most part is a saturated oligomer of isoprene. It resembles or mimics the basic structure or parts of the basic structure of the hydrocarbon backbone of homopolymers and copolymers of propylene and ethylene. This portion, therefore, tends to be compatible with &agr;-olefin polymer material. selected from the group consisting of homopolymers of propylene, homopolymers of ethylene, and copolymers of propylene and ethylene with or without other &agr;-olefins.
The polar portion of the compound comprises a radical with at least one polar bond. This portion, therefore, tends to be compatible with inorganic substances.
Accordingly, the compound is useful in melt blends of such polymer material and solid inorganic material to make them more compatible with each other. Inorganic solid material is material that consists essentially of an inorganic substance that is normally solid at temperatures from well below room temperature to well above the temperatures at which normally solid propylene and ethylene polymers are subjected in melt processing operations such as compounding and article manufacturing. In some embodiments, the material comprises only one inorganic substance. In other embodiments, the material comprises two or more such substances. Examples of an inorganic substance include fillers, extenders, pigments, antacids, and the like.
DETAILED DESCRIPTION OF THE INVENTION
In the more specific aspects of the invention, the generic compound has the general structural formula:
in which R is H or a normal or branched C
1
-C
4
alkyl, n is 2-17, and R′ is a radical with at least one polar bond. In most embodiments of the compound, R′ is X, COOR″, CN, NR
′′′
2
or NR
′′′
2
·HX with R″ being R
′′′
, NR
′′′
2
, NR
′′′
2
·HX or a monovalent metal cation, R
′′′
being H or a normal or branched C
1
-C
4
alkyl, and X being I, Br, Cl or Fl. In each of NR
′′′
2
or NR
′′′
2
·HX, each R
′′′
can be the same or different. However, in preferred embodiments, R″ is NHR
′′′
·HX. Examples of C
1
-C
4
alkyl are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl and tert-butyl. Examples of a monovalent metal cation include cations of alkali metals of Group 1A of the Periodic Table of the Elements (e.g., Li, Na, K and Rb).
One way to make the generic compound comprises condensing isoprene anionically with a C
1
-C
4
alkyllithium to form an oligomer of 3-18 isoprenoid units with C
1
-C
4
alkyl being a substituent of a methyl carbon of the end isopropyl group of the unsaturated hydrocarbon backbone, and with lithium being anionically attached to the methylene carbon at the other end of the backbone. The oligomer is reacted with either ethylene oxide or carbon dioxide, and then with water, to replace the lithium ion with a hydroxyethyl group or a carboxyl group. In either case the resulting compound is hydrogenated over a Pt or Rh catalyst to saturate the backbone. The saturated, hydroxyethyl substituted compound is halogenated with a hydrogen halide (hydrogen bromide or iodide being preferred because of the ease of reaction) to form a compound of the formula in which R′ is X. This halide compound is reacted with (1) an alkali metal cyanide to obtain a compound in which R′ is CN, and (2) ammonia (or ammonium hydroxide), or a mono- or di(C
1
-C
4
alkyl)amine to obtain a compound in which R′ is NR
′′′
2
. The latter compound is reacted with a hydrogen halide to obtain a compound in which R′ is NR
′′′
2
HX. The saturated, carboxyl substituted compound is reacted with (1) a C
1
-C
4
alcohol to form the compound, an ester, in which R″ is C
1
-C
4
alkyl, (2) ammonia (or ammonium hydroxide), or a mono- or di(C
1
-C
4
alkyl)amine to obtain a compound in which R″ is NR
′′′
2
, and (3) an alkali metal base to give a compound in which R″ is a monovalent metal (alkali metal) cation. Similar to the above, the aminocarboxy compound (in which R″ is NR
′′′
2
) is reacted with a hydrogen halide to obtain a compound in which R″ is NR
′′′
2
HX. All of the reactions described in this paragraph are conventional type reactions, and the general conditions thereof are well known in the art.
A highly preferred embodiment of the compound, and a precursor of other embodiments of the compound is 3,7,1 1-trimethyldodecyl halide. A process for making the embodiment starts with 3,7,11-trimethyldodecatriene-1-ol, a naturally occurring isoprenoid known as farnesol. In the process this chemical is catalytically hydrogenated to 3,7,1 1-trimethyldodecan-1-ol which in turn is halogenated. The resulting halide is reacted as above indicated with respect to the generic halide compound to obtain the various other R′ radicals. Thus, the resulting halide is reacted with a C
1
-C
4
alkyl amine to form C
1
-C
4
alkyl (3,7,11-trimethydodecyl) amine. This amine compound then is reacted with a hydrogen halide to form the quaternary compound 3,7,11-trimethyldodecylamine hydrohalide. This quaternary ammonium compound is a preferred compound because of its higher compatibility, more particularly, affinity, compared to the other, non-quaternary ammonium embodiments of the generic compound, with solid inorganic substances.
As above stated, the generic compound is generally compatible with solid inorganic material and with &agr;-olefin polymer material. However, the degree of compatibility with the solid inorganic material varies from one specific embodiment of the compound to another, depending to a large extent on the composition of the inorganic material and the degree of polarity of R′. Similarly, the degree of compatibility with the &agr;-olefin polymer material varies from one specific embodiment of the compound to another, depending to a large extent on the value of n in the formula. Nevertheless, in each case there is significant enhancement of the compatibility of the particles of solid material with the &agr;-olefin polymer material. In addition, the generic compound tends to be in melted condition at the same temperatures at which such polymer material is molten, and this has a favorable effect on compatibility when finely divided particles of solid inorganic material are admixed with the compound and the polymer material in the melted condition. In general, the more compatible a solid inorganic material is with polymer material, the better are the physical properties of the polymer composition containing the solid inorganic material.
The best mode now contemplated of carrying out the invention is illustrated by the following examples of the synthesis of preferred specific embodiments of the compound of this invention. The invention is not limited to these examples. All percentages or parts are by weight unless otherwise expressly stated.
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Database Caplus on STN, Acc. No. 163:415473, Mayer
Bishop C. Edward
Niyogi Suhas G.
Basell Poliolefine Italia S.p.A.
Davis Brian J.
Richter Johann
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