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
2003-01-28
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...
C549S364000
Reexamination Certificate
active
06512030
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 asymmetric DBS compounds comprising monofluoro- or mono(trifluoroalkyl)-pendant groups on one ring of the aforementioned DBS and the other ring system cannot be monofluorinated. Such compounds may be added to or incorporated within polymer compositions which may then be utilized within, as merely examples, food or cosmetic containers and packaging. These inventive asymmetric benzylidene sorbitol acetals are also useful as gelling agents for water and 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 through the incorporation of certain kinds of additives. Certain applications require good clarity or transparency characteristics. These include certain types of plastic plates, sheets, films, containers, and syringes that need to exhibit clarity primarily to facilitate identification of articles, etc., stored, wrapped, and/or covered therewith. Such commercially available plastic additives fall into two categories termed “melt sensitive” and “melt insensitive”. Melt sensitive additives possess melting points 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 (e.g., odor, taste, etc.). 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 of the total composition by 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. Videau, in U.S. Patent 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) 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. and PCT Patent Application WO/92/19221 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 di-acetal of an alditol (such as sorbitol, xylitol, and ribitol), said di-acetal of the alditol having the structure (I):
wherein p is 1 or 2, R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
, R
8
, R
9
, and R
10
are independent selected from the group consisting of hydrogen, lower alkyl groups containing 1-4 carbon atoms, lower alkoxy groups, nitro, halogen, or any two adjacent groups may be combined to form a cyclic group; R
1
, R
2
, R
3
, and R
4
are independently selected from the group consisting of hydrogen, lower alkyl groups containing 1-4 carbon atoms, lower alkoxy groups, fluorine, and trifluoroalkyl groups containing 1-4 carbon atoms; with the proviso that either one of R
1
and R
2
or R
3
and R
4
is fluorine or trifluoroalkyl, as defined above, such that if one of said groups is a fluorine or trifluoroalkyl on a first ring system, then no other fluorines are present on the same first ring system, and, if said first ring system has only one fluorine pendant group in the 3- or 4-position, then the other ring system cannot have a single fluorine pendant group; and with a second proviso that if said first ring system comprises a fluorine in the 3- or 4-position, and an alkyl group in the 3- or 4-position, then the other ring system cannot exhibit the same pendant groups in the same positions as said first ring system.
It should be appreciated with regard to the structural formula set forth above that while only the 1,3:2,4 isomer is represented, this structure is provided for convenience only and the invention is not limited to only isomers of the 1,3:2,4 type, but may include any and all other isomers as well so long as the compound contains two aldehyde substitutents on the alditol moiety.
Throughout this specification, the term “asymmetrical” as it pertains to di-acetals of alditols is intended to mean wherein such alditol acetals possess 1,3- and 2,4-acetal linkages derived from different aldehydes.
The diacetals of the present invention are condensation products of alditol, such as sorbitol or xylitol, and at least two different substituted benzaldehydes. In accordance with this invention, specific examples of suitable substituted benzaldehydes include 4-fluorobenzaldehyde, 3-fluorobenzaldehyde, 3-trifluoromethylbenzaldehyde, 4-trifluoromethylbenzaldehyde, 3-trifluoroethylbenzaldehyde, 4-trifluoroethylbenzaldehyde, and the like, to provide the required monofluoro- or mono(trifluoroalkyl)-ring components. In addition to benzaldehyde alone, other suitable substituted benzaldehydes for the other ring of the DBS system include, without limitation, 3,4-dimethylbenzaldehyde, 4-methylbenzaldehyde, 2,4-dimethylbenzaldehyde, 2,4,5-trimethylbenzaldehyde, 2,4-diethylbenzaldehyde, 4-nitrobenzaldehyde, 3-chloro-4-methylbenzaldehyde, 4-chloro-2,3-dimethylbenzaldehyde, 3-chloro-2,4-dimethylbenzaldehyde, 2,4-dichloro-3-methylbenzaldehyde, 4-chloro-3,5-dimethylbenzaldehyde, and 3-chloro-4-methoxybenzaldehyde, and the like. Preferred di-acetals of the present invention include 1,3-O-(4-fluorobenzylidene):2,4-O-(3,4-dimethylbenzylidene) sorbitol, 1,3-O-(3,4-dimethylbenzylidene):2,4-O-(4-fluorobenzylidene) sorbitol, 1,3-O-(3-fluorobenzylidene):2,4-O-(3,4-dimethylbenzylidene) sorbitol, 1,3-O-(3,4-dimethylbenzylidene):2,4-O-(3-fluorobenzylidene) sorbitol, 1,3-O-(3,
Anderson John D.
Dotson Darin L.
Jones Jeffrey R.
Mehl Nathan A.
Milliken & Company
Moyer Terry T.
Parks William S.
Sanders Kriellion A.
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