Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Processes of preparing a desired or intentional composition...
Reexamination Certificate
2001-03-23
2003-04-15
Sanders, Kriellion A. (Department: 1714)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Processes of preparing a desired or intentional composition...
C524S297000, C424S065000, C424S066000, C424S067000, C424S068000, C549S364000
Reexamination Certificate
active
06548581
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to plastic additives which are useful as nucleating agents and which are especially useful for improving the optical properties of polymeric materials. More particularly, this invention relates to certain bis-halogen-alkyl-benzylidene alditol acetals and polymer compositions thereof which are useful as materials for food or cosmetic containers and packaging. These bis-halogen-alkylbenzylidene alditol acetals are also useful as gelling agents for organic solvents, particularly those used in the preparation of antiperspirant gel sticks.
BACKGROUND OF THE PRIOR ART
All U.S. Patents cited below are herein entirely incorporated by reference.
Numerous attempts have been made to improve the clarity and physical properties of polyolefins by incorporating certain kinds of additives in them. Applications such as the development of plates, sheets, films, containers, and syringes demand clarity or transparency as a necessary property. Commercially available additives fall into two categories termed “melt sensitive” and “melt insensitive”. Melt sensitive additives have melting point which is below or near the normal processing temperatures of polyolefin based resins and include dibenzylidene sorbitol (DBS) systems. Melt insensitive additives do not melt at normal processing temperatures and include sodium benzoate and salts of organic phosphates as examples.
U.S. Pat. No. 4,016,118 to Hamada, et al. teaches that a polyolefin plastic composition containing 0.1% to 0.7% dibenzylidene sorbitol (DBS) as an additive will show improved transparency and reduced molding shrinkage over compositions containing a substituted benzoic acid salt. Additional advancements in sorbitol-based clarification technology have been driven by the need for improved transparency, reduction of plate-out during processing, and improved organoleptic properties. In order to overcome these deficiencies, many derivatives of DBS in which the aromatic rings are substituted with various groups have been proposed.
Mahaffey, in U.S. Pat. No. 4,371,645 discloses a series of dibenzylidene sorbitols having the general formula:
wherein R, R
1
, R
2
, R
3
, and R
4
, are selected from hydrogen, lower alkyl, hydroxy, methoxy, mono- and di-alkylamino, amino, nitro, and halogen, with the proviso that at least one of R
1
, R
2
, R
3
, and R
4
is chlorine or bromine. Effective concentrations of the disclosed substituted DBS derivatives range from 0.01 to about 2 percent by weight of the total composition weight. Further improvements in transparency characteristics are disclosed by Titus, et al. in U.S. Pat. No. 4,808,650. In this patent mono and disubstituted DBS derivatives having the formula:
in which R may be hydrogen or fluorine provide improved clarity applications in polyolefins. Rekers, in U.S. Pat. No. 5,049,605 discloses a series of dibenzylidene sorbitols having the general formula:
in which R
1
and R
2
are independently selected from lower alkyl groups containing 1-4 carbons which together form a carbocyclic ring containing up to 5 carbon atoms. Also disclosed are polyolefin plastics containing the above group of dibenzylidene sorbitols. This patent teaches that these compositions show improved transparency and improved organoleptic properties (desirable taste and odor characteristics) over previous “generations” of sorbitol-based clarifying agents. Videau, in U.S. Pat. No. 5,696,186 discloses substituted DBS derivatives with an alkyl group (methyl, ethyl, or the like) or halogen (fluorine, chlorine, or the like) on the benzene rings for use as nucleation/clarification agents in polyolefins.
Dibenzylidene sorbitol (DBS) derivatives that melt above 240° C. are generally recognized as being less soluble in polyolefins and thus require special processing to effect their dispersion into the polyolefin resin. Typically a higher molding temperature is used to dissolve the additive, but this can lead to decomposition of the additive as exhibited by plateout, yellowing of the resin, and odor generation. To overcome this limitation, mixtures of DBS systems have been used to effect nucleation of polyolefins at molding temperatures<240° C.
Japanese Patent No. 2[1990]-12259 discloses the use of asymmetric DBS systems derived from alkoxy and alkyl substituted benzaldehydes as nucleating agents for polyolefins. Japanese Patent No. 3[1991]-292383 discloses the use of asymmetric diacetals derived from a substituted benzaldehyde and aliphatic aldehydes as gelling agents and nucleating agents for polyolefin resins. U.S. Pat. No. 5,015,684 to Kobayashi, et al. teaches that an asymmetric DBS system derived from benzaldehyde and mono, di, or tri-alkyl substituted benzaldehydes are useful as nucleating agents for polyolefins. Preferred examples claimed within this patent are derived from benzaldehyde and 2,4-dimethylbenzaldehyde or 4-methylbenzaldehyde (p-tolualdehyde). Japanese Patent No. 2[1990]-59832 teaches the preparation and use of pure asymmetric dibenzylidene sorbitol and xylitol systems as gelling agents and nucleating agents. Japanese Patent 7[1995]-286066 discloses the use of asymmetric DBS derivatives derived from 3,4-dimethylbenzaldehyde and various alkyl-substituted or alkoxy-substituted benzaldehydes such as tetralin aldehyde as nucleating agents for polyolefins. Japanese Patent No. 8[1996]-27323 teaches that mixtures of symmetrical DBS systems with organic phosphate salts or amide derivatives provide improved transparency in polyolefins.
Dibenzylidene sorbitol (DBS) is a well known gelling agent for a variety solvent systems as disclosed in U.S. Pat. No. 4,154,816, Roehl et al.; U.S. Pat. No. 4,816,261, Luebbe et al.; and U.S. Pat. No. 4,743,444 to McCall. U.S. Pat. No. 5,609,855 to Oh et al. band W.O. Pat. No. 9219221 to Juneja et al. disclose that di(meta-fluorobenzylidene) sorbitol and di(meta-chlorobenzylidene) sorbitol are extremely useful as gelling agents in the preparation of antiperspirant gel sticks. These two respective DBS systems form effective hard gels and show improved gel stability in the acidic environment of antiperspirant formulations.
DETAILED DESCRIPTION OF THE INVENTION
According to the present invention, a polyolefin plastic composition having improved transparency is provided which comprises a polymer selected from aliphatic polyolefins and copolymers containing at least one aliphatic olefin and one or more ethylenically unsaturated comonomers and at least one nucleating agent conforming to the following Formula (I)
wherein R is selected from hydrogen, lower alkyl groups containing 1-4 carbon atoms, lower alkoxy groups, and fluorine; R
1
, and R
2
, are selected from lower alkyl groups containing 1-4 carbon atoms, lower alkoxy groups, and halogens; R
3
, and R
4
are selected from lower alkyl groups containing 1-4 carbon atoms and which together may form a carbocyclic ring containing up to 6 carbon atoms, lower alkoxy groups, halogens, and hydrogen; with the proviso that only one of R
1
and R
2
is halogen; and p is 0 or 1.
The individual compounds as defined for Structure (I) are inventive compounds alone as well, broadly stated as asymmetric alditol di-acetal compounds comprising at least two arylidene components wherein one of said benzylidene components at least possesses one halogen pendant group in either the 3- or 4-position and one pendant group selected from lower alkyl and lower alkoxy in the 3- or 4-position.
However, as noted above, the compounds conforming with Structure (I), above, may also be utilized individually within the target polyolefin formulations or combined in some manner and in any proportions as well. More particularly, it is contemplated that reaction product mixtures of isomeric compounds confirming to Structure (I) as well as other dibenzylidene alditol compounds will be formed during production of the desired asymmetric compounds of this invention. It is important to note that the reaction necessary to produce the desired asymmetric diacetals requires the utilization of
Anderson John D.
Dotson Darin L.
Jones Jeffrey R.
Mehl Nathan A.
Sheppard Shawn R.
Milliken & Company
Moyer Terry T.
Parks William S.
Sanders Kriellion A.
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