Trisamide compounds and compositions comprising the same

Abstract

To provide a composition containing a trisamide compound useful as a transparentizing agent in a polyolefin polymer or the like, the composition exhibiting a very low haze level and minimal extraction of trisamide compounds.SOLUTION: For example, there is provided a composition comprising two or more trisamide compounds, such as N,N-di(cis-4-tert-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide and N,N-di(cis-4-tert-butylcyclohexyl)-5-(cis-4-isopropylcyclohexylcarbonylamino)isophthalamide, in which 60% or more of the alkyl groups attached to the 4-position of the cyclohexanediyl moiety are in the cis position relative to the non-hydrogen substituent attached to the 1-position of the cyclohexanediyl moiety. The polymer composition comprises the above composition and a polyolefin polymer.SELECTED DRAWING: None

Description

[Technical Field]

[0001] This application relates to trisamide compounds (specifically, trisamide derivatives formally derived from 5-aminoisophthalic acid) and compositions containing trisamide compounds. BACKGROUND OF THE INVENTION

[0002] Polymer resins are widely used in a variety of fields due to, among other things, their excellent processability, mechanical properties (especially on a relative weight basis), and electrical properties. While the polymer itself may have beneficial properties, additives may be used to further enhance the properties of the polymer and / or to mitigate its disadvantages.

[0002]

[0003] Polyolefins are a particularly versatile group of polymer resins. Polyolefins are semicrystalline polymers. Polyolefins cooled relatively slowly (such as those encountered during the production of molded plastic parts) contain amorphous regions, where the polymer chains are randomly arranged, and crystalline regions, where the polymer chains are regularly arranged. Within these crystalline regions of polyolefins, the polymer chains are aligned into domains commonly referred to as "crystalline lamellae." Under typical processing conditions, as polyolefin polymers cool from the molten state, the crystalline lamellae grow radially in all directions. This radial growth results in the formation of spherulites, which are spherical, semicrystalline regions composed of multiple crystalline lamellae interrupted by amorphous regions. The size of the spherulites is affected by several parameters and can range from hundreds of nanometers to several millimeters in diameter. When the spherulite size is significantly larger than the wavelength of visible light, the spherulites scatter visible light passing through the polymer. This scattering of visible light results in a cloudy appearance commonly referred to as "polymer haze" or simply "haze." While in some applications a significant level of polymer haze may be acceptable, there are certain applications (e.g., storage containers) where the consumer desires a relatively clear plastic and accordingly low haze levels are required.

[0003]

[0004] Over the years, several approaches have been developed to reduce haze in polyolefins. One approach that has met with considerable commercial success involves the use of clarifying agents. Clarifying agents are additives (often organic compounds) that, when melt-processed with a polymer, nucleate crystallization in the cooling polymer, reducing spherulite size or even substantially preventing the formation of these effective light scatterers. For example, bis(3,4-dimethylbenzylidene) sorbitol has met with considerable commercial success due to its ability to reduce haze in polypropylene polymers. However, bis(3,4-dimethylbenzylidene) sorbitol has not been without its limitations. In particular, clarifying agents cannot reduce haze in polypropylene polymers to levels comparable to those of more transparent polymers, such as polystyrene and acrylic resins. The residual haze of polymers clarified with bis(3,4-dimethylbenzylidene) sorbitol limits the applications and end uses of these polymers.

[0004]

[0005] To address the limitations of sorbitol acetals (e.g., bis(3,4-dimethylbenzylidene)sorbitol), other clarifying agents have been developed. For example, trisamide compounds (e.g., trisamide derivatives formally derived from 1,3,5-benzenetriamine, 3,5-diaminobenzoic acid, 5-aminoisophthalic acid, or trimesic acid) initially showed promise due to the fact that relatively low loadings of such compounds could produce haze levels in polypropylene polymers comparable to those achieved with bis(3,4-dimethylbenzylidene)sorbitol. Despite their initial promise, the disclosed trisamide compounds still fail to produce haze levels comparable to those of more transparent polymers. Furthermore, many of the disclosed trisamide compounds can be extracted from the polypropylene to which they are added. These undesirable levels of extraction make such trisamide compounds less suitable for use in food contact and medical applications (i.e., applications in which the polymer clarified with the trisamide compounds comes into contact with food [e.g., food storage or packaging] or is used in medical devices [e.g., syringes]), where industry preferences and / or regulatory requirements call for additives that exhibit minimal extraction from the polymer.

[0005]

[0006] Therefore, there is a need for clarifying agents that can both produce desirably low haze levels in polyolefin polymers and exhibit minimal extraction from the polyolefin polymers to which they are added. There is also a need for polymer compositions incorporating such clarifying agents that exhibit the desired combination of low haze and minimal extraction of the clarifying agent. Various embodiments described herein seek to provide such clarifying agents and compositions. Brief Summary of the Invention

[0007] In a first aspect, the present invention provides a compound of formula (I)

[0006] [ka]

[0007] [In the formula, R 1 , R 2 , and R 3 are independently selected from the group consisting of alkyl groups.

[0008] In a second aspect, the present invention provides a polymer composition comprising a compound of formula (I) and a polyolefin polymer.

[0009] In a first aspect, the present invention provides a compound of formula (I) below, which is a trisamide derivative formally derived from 5-aminoisophthalic acid. The structure of formula (I) is as follows:

[0010] [ka]

[0011] In formula (I), R 1 , R 2 , and R 3 The groups are independently selected from the group consisting of alkyl groups.

[0012]

[0010] R 1 , R 2 , and R 3 The group can be any suitable alkyl group. In a preferred embodiment, R 1 , R 2 , and R 3 is C1~C 20 Alkyl groups (e.g., C3-C 20 alkyl group), more preferably C1 to C 12 Alkyl groups (e.g., C3-C 12alkyl groups), even more preferably C1-C8 alkyl groups (e.g., C3-C8 alkyl groups), and most preferably C1-C5 alkyl groups (e.g., C2-C5 alkyl groups or C3-C5 alkyl groups). Suitable alkyl groups can be either linear or branched. In a preferred embodiment, R 1 , R 2 , and R 3 At least one of R is a branched alkyl group. 1 , R 2 , and R 3 If only one of R is a branched alkyl group, 3 is preferably a branched alkyl group. 1 , R 2 and R 3 In another embodiment where only one of R 1 is preferably a branched alkyl group. In another preferred embodiment, R 1 , R 2 , and R 3 At least two of R are independently selected branched alkyl groups. 1 and R 2 is preferably an independently selected branched alkyl group. In another such embodiment, R 2 and R 3 is preferably an independently selected branched alkyl group. In yet another preferred embodiment, R 1 , R 2 , and R 3 is an independently selected branched alkyl group. In those embodiments containing a branched alkyl group, the alkyl group can contain any suitable number of carbon atoms, with preferred examples being C3 to C6. 20 Branched alkyl groups, C3-C 12 branched alkyl groups, C3-C8 branched alkyl groups, and C3-C5 branched alkyl groups. Suitable branched alkyl groups preferably contain a branch point located at the alpha or beta carbon relative to the cyclohexanediyl moiety.

[0013] In a preferred embodiment, R 1 , R 2 , and R 3 is independently selected from the group consisting of n-propyl, isopropyl, n-butyl, sec-butyl (i.e., butan-2-yl or 1-methylpropyl), isobutyl (i.e., 2-methylpropyl), tert-butyl (i.e., 1,1-dimethylethyl), n-pentyl, tert-pentyl (i.e., 2-methylbutan-2-yl or 1,1-dimethylpropyl), neopentyl (i.e., 2,2-dimethylpropyl), isopentyl (i.e., 3-methylbutyl), sec-pentyl (i.e., pentan-2-yl or 1-methylbutyl), sec-isopentyl (i.e., 3-methylbutan-2-yl or 1,2-dimethylpropyl), pentan-3-yl (i.e., 1-ethylpropyl), and 2-methylbutyl. In a more preferred embodiment, R 1 , R 2 , and R 3 is independently selected from the group consisting of n-propyl, isopropyl, n-butyl, sec-butyl (i.e., butan-2-yl or 1-methylpropyl), isobutyl (i.e., 2-methylpropyl), tert-butyl (i.e., 1,1-dimethylethyl), tert-pentyl (i.e., 2-methylbutan-2-yl or 1,1-dimethylpropyl), sec-pentyl (i.e., pentan-2-yl or 1-methylbutyl), sec-isopentyl (i.e., 3-methylbutan-2-yl or 1,2-dimethylpropyl), and pentan-3-yl (i.e., 1-ethylpropyl). In yet another preferred embodiment, R 1 , R 2 , and R 3 are independently selected from the group consisting of n-propyl, isopropyl, n-butyl, isobutyl (i.e., 2-methylpropyl), tert-butyl (i.e., 1,1-dimethylethyl), and tert-pentyl (i.e., 2-methylbutan-2-yl or 1,1-dimethylpropyl).

[0014] As mentioned above, R1 , R 2 and R 3 At least one of R is preferably a branched alkyl group. 1 , R 2 and R 3 is selected from the group consisting of isopropyl, sec-butyl (i.e., butan-2-yl or 1-methylpropyl), isobutyl (i.e., 2-methylpropyl), tert-butyl (i.e., 1,1-dimethylethyl), tert-pentyl (i.e., 2-methylbutan-2-yl or 1,1-dimethylpropyl), neopentyl (i.e., 2,2-dimethylpropyl), isopentyl (i.e., 3-methylbutyl), sec-pentyl (i.e., pentan-2-yl or 1-methylbutyl), sec-isopentyl (i.e., 3-methylbutan-2-yl or 1,2-dimethylpropyl), pentan-3-yl (i.e., 1-ethylpropyl), and 2-methylbutyl. 1 , R 2 and R 3 is selected from the group consisting of isopropyl, sec-butyl (i.e., butan-2-yl or 1-methylpropyl), isobutyl (i.e., 2-methylpropyl), tert-butyl (i.e., 1,1-dimethylethyl), tert-pentyl (i.e., 2-methylbutan-2-yl or 1,1-dimethylpropyl), sec-pentyl (i.e., pentan-2-yl or 1-methylbutyl), sec-isopentyl (i.e., 3-methylbutan-2-yl or 1,2-dimethylpropyl), and pentan-3-yl (i.e., 1-ethylpropyl). 1 , R 2 and R 3 In yet another preferred embodiment, at least one of R is selected from the group consisting of isopropyl, isobutyl (i.e., 2-methylpropyl), tert-butyl (i.e., 1,1-dimethylethyl), and tert-pentyl (i.e., 2-methylbutan-2-yl or 1,1-dimethylpropyl).1 , R 2 , and R 3 At least one of R is selected from the group consisting of tert-butyl (i.e., 1,1-dimethylethyl) and tert-pentyl (i.e., 2-methylbutan-2-yl or 1,1-dimethylpropyl). 3 is a branched alkyl group selected from one of the groups described in this paragraph. 2 and R 3 are each a branched alkyl group independently selected from one of the groups described in this paragraph. 1 , R 2 and R 3 is a branched alkyl group independently selected from one of the groups described in this paragraph.

[0015] In a preferred embodiment, the compound is (i) N,N-di(4-isopropylcyclohexyl)-5-(4-n-propylcyclohexylcarbonylamino)isophthalamide; (ii) N,N-di(4-isopropylcyclohexyl)-5-(4-isopropylcyclohexylcarbonylamino)isophthalamide; (iii) N,N-di(4-isopropylcyclohexyl)-5-(4-n-butylcyclohexylcarbonylamino)isophthalamide; (iv) N,N-di(4-isopropylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)isophthalamide; (v) N,N-di(4-isopropylcyclohexyl)-5-(4-n-pentylcyclohexylcarbonylamino)isophthalamide; (vi) N,N-di(4-isopropylcyclohexyl)-5-(4-tert-pentylcyclohexylcarbonylamino)isophthalamide; (vii) N,N-di(4-n-butylcyclohexyl)-5-(4-n-butylcyclohexylcarbonylamino)isophthalamide; (viii) N,N-di(4-n-butylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)isophthalamide; (ix) N,N-di(4-sec-butylcyclohexyl)-5-(4-sec-butylcyclohexylcarbonylamino)isophthalamide; (x) N,N-di(4-sec-butylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)isophthalamide; (xi) N,N-di(4-tert-butylcyclohexyl)-5-(4-n-propylcyclohexylcarbonylamino)isophthalamide; (xii) N,N-di(4-tert-butylcyclohexyl)-5-(4-isopropylcyclohexylcarbonylamino)isophthalamide; (xiii) N,N-di(4-tert-butylcyclohexyl)-5-(4-n-butylcyclohexylcarbonylamino)isophthalamide; (xiv) N,N-di(4-tert-butylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)isophthalamide (xv) N,N-di(4-tert-butylcyclohexyl)-5-(4-n-pentylcyclohexylcarbonylamino)isophthalamide; (xvi) N,N-di(4-tert-pentylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)isophthalamide; (xvii) N,N-di(4-tert-pentylcyclohexyl)-5-(4-tert-pentylcyclohexylcarbonylamino)isophthalamide; and (xviii) selected from the group consisting of mixtures thereof (i.e., mixtures of any two or more of the foregoing compounds).

[0016] In another preferred embodiment, the compound is (i) N,N-di(4-isopropylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)isophthalamide; (ii) N,N-di(4-isopropylcyclohexyl)-5-(4-tert-pentylcyclohexylcarbonylamino)isophthalamide; (iii) N,N-di(4-n-butylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)isophthalamide; (iv) N,N-di(4-sec-butylcyclohexyl)-5-(4-sec-butylcyclohexylcarbonylamino)isophthalamide; (v) N,N-di(4-sec-butylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)isophthalamide; (vi) N,N-di(4-tert-butylcyclohexyl)-5-(4-n-propylcyclohexylcarbonylamino)isophthalamide; (vii) N,N-di(4-tert-butylcyclohexyl)-5-(4-isopropylcyclohexylcarbonylamino)isophthalamide; (viii) N,N-di(4-tert-butylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)isophthalamide; (ix) N,N-di(4-tert-pentylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)isophthalamide; (x) N,N-di(4-tert-pentylcyclohexyl)-5-(4-tert-pentylcyclohexylcarbonylamino)isophthalamide; and (xi) mixtures thereof (i.e., mixtures of any two or more of the foregoing compounds).

[0017] In one preferred embodiment, the compound of formula (I) is N,N-di(4-tert-butylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-di(4-tert-butylcyclohexyl)-5-(4-isopropylcyclohexylcarbonylamino)isophthalamide. In yet another preferred embodiment, the compound of formula (I) is N,N-di(4-tert-butylcyclohexyl)-5-(4-n-butylcyclohexylcarbonylamino)isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-di(4-tert-pentylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)isophthalamide. In yet another preferred embodiment, the compound of formula (I) is N,N-di(4-tert-butylcyclohexyl)-5-(4-n-propylcyclohexylcarbonylamino)isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-di(4-isopropylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)isophthalamide. In yet another preferred embodiment, the compound of formula (I) is N,N-di(4-tert-pentylcyclohexyl)-5-(4-tert-pentylcyclohexylcarbonylamino)isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-di(4-isopropylcyclohexyl)-5-(4-n-butylcyclohexylcarbonylamino)isophthalamide. In yet another preferred embodiment, the compound of formula (I) is N,N-di(4-isopropylcyclohexyl)-5-(4-n-pentylcyclohexylcarbonylamino)isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-di(4-tert-butylcyclohexyl)-5-(4-n-pentylcyclohexylcarbonylamino)isophthalamide. In yet another preferred embodiment, the compound of formula (I) is N,N-di(4-isopropylcyclohexyl)-5-(4-tert-pentylcyclohexylcarbonylamino)isophthalamide.In another preferred embodiment, the compound of formula (I) is N,N-di(4-isopropylcyclohexyl)-5-(4-n-propylcyclohexylcarbonylamino)isophthalamide. In yet another preferred embodiment, the compound of formula (I) is N,N-di(4-n-butylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-di(4-n-butylcyclohexyl)-5-(4-n-butylcyclohexylcarbonylamino)isophthalamide. In yet another preferred embodiment, the compound of formula (I) is N,N-di(4-sec-butylcyclohexyl)-5-(4-sec-butylcyclohexylcarbonylamino)isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-di(4-sec-butylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)isophthalamide.

[0018] As can be seen in formula (I), each cyclohexanediyl moiety contains non-hydrogen substituents (i.e., R 1 , R 2 , or R 3 The non-hydrogen substituents attached to each cyclohexanediyl moiety can be arranged in two different spatial configurations relative to each other. Both non-hydrogen substituents can be on the same side of the mean plane of the cyclohexane ring, which corresponds to a cis configuration, or both non-hydrogen substituents can be on opposite sides of the mean plane of the cyclohexane ring, which corresponds to a trans configuration. R 1 , R 2 , and R 3 Each of the groups can be positioned either cis or trans relative to the non-hydrogen substituent attached to the 1-position of the corresponding cyclohexanediyl moiety. 1 , R 2 , and R 3At least one of the groups is positioned cis to the non-hydrogen substituent attached to the 1-position of the corresponding cyclohexanediyl moiety. 1 , R 2 , and R 3 At least two of the groups are positioned cis to the non-hydrogen substituent attached to the 1-position of the corresponding cyclohexanediyl moiety. 1 , R 2 , and R 3 Each of the groups is positioned cis to the non-hydrogen substituent attached to the 1-position of the corresponding cyclohexanediyl moiety.

[0019] In a preferred embodiment, the compound is (i) N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-n-propylcyclohexylcarbonylamino)isophthalamide; (ii) N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-isopropylcyclohexylcarbonylamino)isophthalamide; (iii) N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-n-butylcyclohexylcarbonylamino)isophthalamide; (iv) N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide; (v) N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-n-pentylcyclohexylcarbonylamino)isophthalamide; (vi) N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-tert-pentylcyclohexylcarbonylamino)isophthalamide; (vii) N,N-di(cis-4-n-butylcyclohexyl)-5-(cis-4-n-butylcyclohexylcarbonylamino)isophthalamide; (viii) N,N-di(cis-4-n-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide; (ix) N,N-di(cis-4-sec-butylcyclohexyl)-5-(cis-4-sec-butylcyclohexylcarbonylamino)isophthalamide; (x) N,N-di(cis-4-sec-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide; (xi) N,N-di(cis-4-tert-butylcyclohexyl)-5-(cis-4-n-propylcyclohexylcarbonylamino)isophthalamide; (xii) N,N-di(cis-4-tert-butylcyclohexyl)-5-(cis-4-isopropylcyclohexylcarbonylamino)isophthalamide; (xiii) N,N-di(cis-4-tert-butylcyclohexyl)-5-(cis-4-n-butylcyclohexylcarbonylamino)isophthalamide; (xiv) N,N-di(cis-4-tert-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide (xv) N,N-di(cis-4-tert-butylcyclohexyl)-5-(cis-4-n-pentylcyclohexylcarbonylamino)isophthalamide; (xvi) N,N-di(cis-4-tert-pentylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide; (xvii) N,N-di(cis-4-tert-pentylcyclohexyl)-5-(cis-4-tert-pentylcyclohexylcarbonylamino)isophthalamide; and (xviii) selected from the group consisting of mixtures thereof (i.e., mixtures of any two or more of the foregoing compounds).

[0020] In another preferred embodiment, the compound is (i) N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide; (ii) N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-tert-pentylcyclohexylcarbonylamino)isophthalamide; (iii) N,N-di(cis-4-n-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide; (iv) N,N-di(cis-4-sec-butylcyclohexyl)-5-(cis-4-sec-butylcyclohexylcarbonylamino)isophthalamide; (v) N,N-di(cis-4-sec-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide; (vi) N,N-di(cis-4-tert-butylcyclohexyl)-5-(cis-4-n-propylcyclohexylcarbonylamino)isophthalamide; (vii) N,N-di(cis-4-tert-butylcyclohexyl)-5-(cis-4-isopropylcyclohexylcarbonylamino)isophthalamide; (viii) N,N-di(cis-4-tert-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide; (ix) N,N-di(cis-4-tert-pentylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide; (x) N,N-di(cis-4-tert-pentylcyclohexyl)-5-(cis-4-tert-pentylcyclohexylcarbonylamino)isophthalamide; and (xi) mixtures thereof (i.e., mixtures of any two or more of the foregoing compounds).

[0021] In one preferred embodiment, the compound of formula (I) is N,N-di(cis-4-tert-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-di(cis-4-tert-butylcyclohexyl)-5-(cis-4-isopropylcyclohexylcarbonylamino)isophthalamide. In yet another preferred embodiment, the compound of formula (I) is N,N-di(cis-4-tert-butylcyclohexyl)-5-(cis-4-n-butylcyclohexylcarbonylamino)isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-di(cis-4-tert-pentylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide. In yet another preferred embodiment, the compound of formula (I) is N,N-di(cis-4-tert-butylcyclohexyl)-5-(cis-4-n-propylcyclohexylcarbonylamino)isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide. In yet another preferred embodiment, the compound of formula (I) is N,N-di(cis-4-tert-pentylcyclohexyl)-5-(cis-4-tert-pentylcyclohexylcarbonylamino)isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-n-butylcyclohexylcarbonylamino)isophthalamide. In yet another preferred embodiment, the compound of formula (I) is N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-n-pentylcyclohexylcarbonylamino)isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-di(cis-4-tert-butylcyclohexyl)-5-(cis-4-n-pentylcyclohexylcarbonylamino)isophthalamide.In yet another preferred embodiment, the compound of formula (I) is N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-tert-pentylcyclohexylcarbonylamino)isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-n-propylcyclohexylcarbonylamino)isophthalamide. In yet another preferred embodiment, the compound of formula (I) is N,N-di(cis-4-n-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-di(cis-4-n-butylcyclohexyl)-5-(cis-4-n-butylcyclohexylcarbonylamino)isophthalamide. In yet another preferred embodiment, the compound of formula (I) is N,N-di(cis-4-sec-butylcyclohexyl)-5-(cis-4-sec-butylcyclohexylcarbonylamino)isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-di(cis-4-sec-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide.

[0022]

[0016] The present application also encompasses compositions containing one or more compounds of formula (I), for example, compositions containing a mixture of two or more compounds of formula (I) (in this context, cis and trans isomers are considered to be different compounds, and therefore a mixture of two or more isomers constitutes a composition containing a mixture of two or more compounds of formula (I)). In such embodiments, the R 1 , R 2 , and R 3 Preferably, 60% or more of the R groups are cis to the non-hydrogen substituent attached to the 1-position of the corresponding cyclohexanediyl moiety. More preferably, the R groups of all compounds of formula (I) present in the composition are cis to the non-hydrogen substituent attached to the 1-position of the corresponding cyclohexanediyl moiety. 1 , R 2 , and R 3In another preferred embodiment, at least about 65% of the R groups are cis to the non-hydrogen substituent attached to the 1-position of the corresponding cyclohexanediyl moiety. 1 , R 2 , and R 3 In yet another preferred embodiment, at least about 70% of the R groups are cis to the non-hydrogen substituent attached to the 1-position of the corresponding cyclohexanediyl moiety. 1 , R 2 , and R 3 In another preferred embodiment, at least about 75% of the R groups are cis to the non-hydrogen substituent attached to the 1-position of the corresponding cyclohexanediyl moiety. 1 , R 2 , and R 3 In yet another preferred embodiment, at least about 80% of the R groups are cis to the non-hydrogen substituent attached to the 1-position of the corresponding cyclohexanediyl moiety. 1 , R 2 , and R 3 In another preferred embodiment, at least 85% of the R groups are cis to the non-hydrogen substituent attached to position 1 of the corresponding cyclohexanediyl moiety. 1 , R 2 , and R 3 In yet another preferred embodiment, at least about 90% of the R groups are cis to the non-hydrogen substituent attached to the 1-position of the corresponding cyclohexanediyl moiety. 1 , R 2 , and R 3 About 95% or more (e.g., about 96% or more, about 97% or more, about 98% or more, or about 99% or more) of the groups are cis to the non-hydrogen substituent attached to the 1-position of the corresponding cyclohexanediyl moiety.

[0023] In another preferred embodiment of the composition containing a mixture of two or more compounds of formula (I), about 60 mole percent or more of the compounds of formula (I) present in the composition have R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 1 , R 2 , and R 3 More preferably, about 65 mole percent or more of the compounds of formula (I) present in the composition have R groups each cis to the non-hydrogen substituent attached to the 1-position of the corresponding cyclohexanediyl moiety. 1 , R 2 , and R 3 In yet another preferred embodiment, about 70 mole % or more of the compounds of formula (I) present in the composition have R groups each cis to the non-hydrogen substituent attached to the 1-position of the corresponding cyclohexanediyl moiety. 1 , R 2 , and R 3 In another preferred embodiment, about 75 mole % or more of the compounds of formula (I) present in the composition have R groups each cis to the non-hydrogen substituent attached to the 1-position of the corresponding cyclohexanediyl moiety. 1 , R 2 , and R 3 In yet another preferred embodiment, about 80 mole % or more of the compounds of formula (I) present in the composition have R groups each cis to the non-hydrogen substituent attached to the 1-position of the corresponding cyclohexanediyl moiety. 1 , R 2 , and R 3 In another preferred embodiment, about 85 mole % or more of the compounds of formula (I) present in the composition have R groups each cis to the non-hydrogen substituent attached to the 1-position of the corresponding cyclohexanediyl moiety. 1 , R 2 , and R 3 In yet another preferred embodiment, about 90 mole % or more of the compounds of formula (I) present in the composition have R groups each cis to the non-hydrogen substituent attached to the 1-position of the corresponding cyclohexanediyl moiety. 1 , R 2 , and R 3In another preferred embodiment, about 95 mol % or more (e.g., about 96 mol % or more, about 97 mol % or more, about 98 mol % or more, or about 99 mol % or more) of the compounds of Formula (I) present in the composition have R groups that are each cis to the non-hydrogen substituent attached to the 1-position of the corresponding cyclohexanediyl moiety. 1 , R 2 , and R 3 It has a group.

[0024] The compounds of formula (I) can be prepared using any suitable method or synthetic process. For example, the compounds can be prepared by first reacting the desired 4-alkylcyclohexylamine with 5-nitroisophthaloyl dichloride to form the compound of formula (A):

[0025] [ka]

[0026] The intermediate compound of formula (A) can then be hydrogenated using known methods to produce the compound of formula (B):

[0027] [ka]

[0028] The amine compound of formula (B) can then be reacted with the desired 4-alkylcyclohexanecarbonyl chloride to produce the desired compound of formula (I).

[0029]

[0019] R 1 and R 2 The compound of formula (I) having a different structure can be prepared, for example, by reacting a 5-nitroisophthalic acid monoalkyl ester (e.g., 5-nitroisophthalic acid monomethyl ester) with oxalyl chloride to obtain a compound of formula (J):

[0030] [ka]

[0031] [In the formula, R 11 where the alkyl group is an alkyl group, such as a methyl group. The acid chloride compound of formula (J) can then be reacted with the desired 4-alkylcyclohexylamine to produce the compound of formula (K):

[0032] [ka]

[0033] The intermediate compound of formula (K) can then be saponified with a suitable base (e.g., lithium hydroxide) to produce the corresponding carboxylic acid salt (e.g., lithium salt of carboxylic acid) and alcohol (i.e., structure R 11 Alcohols with OH, R 11 When is methyl, such a methanol can be obtained. The corresponding carboxylic acid salt can then be hydrolyzed with an appropriate acid (e.g., hydrochloric acid) to give the following formula (L):

[0034] [ka]

[0035] The acid of formula (L) can then be reacted with oxalyl chloride to produce an acid of formula (M):

[0036] [ka]

[0037] The acid chloride of formula (M) can then be reacted with the desired 4-alkylcyclohexylamine to give the corresponding acid chloride compound of formula (N):

[0038] [ka]

[0039] The intermediate compound of formula (N) can then be reduced using known methods (e.g., hydrogenation) to produce an intermediate compound of formula (O):

[0040] [ka]

[0041] Finally, the intermediate compound of formula (O) can be reacted with the desired 4-alkylcyclohexanecarbonyl chloride to give the desired compound of formula (I).

[0042] In a second aspect, the present invention provides a polymer composition comprising a compound of formula (I) and a polymer. In such an aspect, the compound of formula (I) may be any of the aspects discussed above in relation to the first aspect of the invention (e.g., a composition containing a particular compound or mixture of compounds).

[0043] The polymer composition can include any suitable polymer. Preferably, the polymer is a thermoplastic polymer, such as a polyolefin, polyester, polyamide, polylactic acid, polycarbonate, acrylic polymer, or a mixture thereof. More preferably, the polymer is a polyolefin polymer, such as a polypropylene polymer, a polyethylene polymer, a polymethylpentene polymer (e.g., poly(4-methyl-1-pentene)), a polybutylene polymer, a poly(vinylcyclohexane) polymer, and a mixture thereof. In a preferred embodiment, the polymer is a polypropylene polymer. More preferably, the polymer is selected from the group consisting of polypropylene homopolymers (e.g., atactic polypropylene homopolymer, isotactic polypropylene homopolymer, and syndiotactic polypropylene homopolymer), polypropylene copolymers (e.g., polypropylene random copolymers), polypropylene impact copolymers, and mixtures thereof. Suitable polypropylene copolymers include, but are not limited to, random copolymers prepared from the polymerization of propylene in the presence of a comonomer selected from the group consisting of ethylene, but-1-ene (i.e., 1-butene), and hex-1-ene (i.e., 1-hexene). In such polypropylene random copolymers, the comonomer can be present in any suitable amount, but is typically present in an amount of less than about 10% by weight (e.g., from about 1 to about 7% by weight). Suitable polypropylene impact copolymers include, but are not limited to, those produced by the addition of a copolymer selected from the group consisting of ethylene-propylene rubber (EPR), ethylene propylene-diene monomer (EPDM), polyethylene, and plastomer to a polypropylene homopolymer or polypropylene random copolymer. In such polypropylene impact copolymers, the copolymer can be present in any suitable amount, but is typically present in an amount of from about 5 to about 25% by weight.In a preferred embodiment, the polymer composition comprises a polyolefin polymer selected from the group consisting of a polypropylene homopolymer, a polypropylene random copolymer, and mixtures thereof. More preferably, the polymer composition comprises a polypropylene random copolymer.

[0044] The polymer composition of the present invention can contain any suitable amount of the compound of formula (I) described above. In a preferred embodiment, the polymer composition comprises at least 0.001 wt. % of the compound of formula (I), based on the total weight of the composition. In another preferred embodiment, the polymer composition comprises at least 0.002 wt. %, at least 0.003 wt. %, at least 0.004 wt. %, at least 0.005 wt. %, at least 0.01 wt. %, at least 0.02 wt. %, at least 0.03 wt. %, at least 0.04 wt. %, at least 0.05 wt. %, at least 0.1 wt. %, at least 0.3 wt. %, at least 0.5 wt. %, at least 1 wt. %, at least 5 wt. %, or at least 10 wt. % of the compound of formula (I), based on the total weight of the composition. In another embodiment, the polymer composition preferably comprises less than 99 wt. % of the compound of formula (I), based on the total weight of the composition. In another preferred embodiment, the polymer composition comprises less than 95 wt%, less than 80 wt%, less than 50 wt%, less than 25 wt%, less than 10 wt%, less than 5 wt%, less than 2 wt%, less than 1 wt%, less than 0.5 wt%, less than 0.2 wt%, less than 0.1 wt%, or less than 0.07 wt% of a compound of formula (I), based on the total weight of the composition. In a series of particularly preferred embodiments, the polymer composition comprises 0.001 wt % to 0.5 wt % (e.g., 0.01 wt % to 0.5 wt % or 0.05 wt % to 0.5 wt %), 0.001 wt % to 0.2 wt % (e.g., 0.01 wt % to 0.2 wt % or 0.05 wt % to 0.2 wt %), 0.001 wt % to 0.1 wt % (e.g., 0.01 wt % to 0.1 wt % or 0.05 wt % to 0.1 wt %), or 0.001 wt % to 0.07 wt % (e.g., 0.01 wt % to 0.07 wt %) of the compound of formula (I), relative to the total weight of the composition. As noted above, the polymer composition of the present invention can comprise multiple compounds of formula (I). In those embodiments in which the polymer composition comprises multiple trisamide compounds of formula (I), each trisamide compound can be present in an amount that falls within one of the ranges recited above, or the combined amount of all of the trisamide compounds can fall within one of the ranges recited above.

[0045] The polymer compositions described herein can contain other polymer additives in addition to the compound of formula (I). Suitable additional polymer additives include, but are not limited to, antioxidants (e.g., phenolic antioxidants, phosphite antioxidants, and combinations thereof), antiblocking agents (e.g., amorphous silica and diatomaceous earth), pigments (e.g., organic and inorganic pigments) and other colorants (e.g., dyes and polymeric colorants), fillers and reinforcing agents (e.g., glass, glass fiber, talc, calcium carbonate, and magnesium oxysulfate whiskers), nucleating agents, clarifying agents, acid scavengers (metal salts of fatty acids, e.g., metal salts of stearic acid), polymer processing additives (e.g., polymer processing additives for fluoropolymers), polymer crosslinking agents, slip agents (e.g., fatty acid amide compounds derived from the reaction of a fatty acid with ammonia or an amine-containing compound), fatty acid ester compounds (e.g., fatty acid ester compounds derived from the reaction of a fatty acid with a hydroxyl-containing compound, e.g., glycerin, diglycerol, and combinations thereof), and combinations of the foregoing.

[0046] The polymer compositions described herein can be produced by any suitable method. For example, a polyolefin composition can be produced by simple mixing (e.g., high shear or high intensity mixing) of a polyolefin polymer, a compound of Formula (I), and any additional optional ingredients. Alternatively, an additive composition comprising a compound of Formula (I) and any additional optional ingredients (e.g., those described above) can be preblended to provide a preblend composition. This preblend composition can then be mixed with a polymer to produce the polymer composition described above. The polymer composition can be provided in any form suitable for use in further processing to produce an article. For example, the polymer composition can be provided in the form of a powder (e.g., a free-flowing powder), flakes, pellets, prills, tablets, agglomerates, etc.

[0047] The polymer compositions described herein are believed to be useful for producing thermoplastic articles. The polymer compositions can be formed into the desired thermoplastic article by any suitable technique, such as injection molding, injection rotomolding, blow molding (e.g., injection blow molding or injection stretch blow molding), extrusion (e.g., sheet extrusion, film extrusion, cast film extrusion, or foam extrusion), extrusion blow molding, thermoforming, rotomolding, film blowing (blown film), film casting (cast film), and the like.

[0048] The polymer compositions described herein can be used to manufacture any suitable article or product, including, but not limited to, medical devices (e.g., pre-filled syringes for retort applications, intravenous supply containers, and blood collection devices), food packaging, liquid containers (e.g., containers for beverages, medications, personal care compositions, shampoos, etc.), clothing cases, microwaveable items, shelving, cabinet doors, machine parts, automotive parts, sheet, pipe, tubing, rotational molded parts, blow molded parts, films, fibers, etc.

[0049] The polymer compositions of the present invention have been found to exhibit a highly desirable combination of low haze and low extractability of the trisamide compounds of formula (I). Polymer compositions (e.g., polypropylene random copolymer compositions) containing compounds of formula (I) generally exhibit haze levels at least 15% lower than those exhibited by polymer compositions containing structurally similar trisamide compounds not encompassed by formula (I). Furthermore, polymer compositions containing specific compounds of formula (I) have been found to exhibit haze levels that are one order of magnitude lower than those exhibited by more transparent polymers, such as polystyrene and acrylic polymers. As noted above, these polymer compositions also exhibit exceptionally good (i.e., low) extraction of the compounds of formula (I) from the polymer compositions. In fact, polymer compositions containing specific compounds of formula (I) have been found to exhibit extractable levels that are one to two orders of magnitude lower than those exhibited by polymer compositions containing structurally similar trisamide compounds not encompassed by formula (I). It is believed that these properties exhibited by the polymer compositions of the present invention make them particularly well suited for use in the manufacture of thermoplastic articles or products requiring low haze levels and low extractables, such as articles and products for food contact and medical applications.

[0050] The following examples further illustrate the above-described subject matter but, of course, should not be construed as in any way limiting its scope.

[0051] Example 1 This example illustrates the synthesis of the trisamide compounds of the present invention (ie, the trisamide compounds of formula (I)).

[0052]

[0030] 16.00 g (64.51 mmol) of 5-nitroisophthaloyl dichloride was added to 400 mL of dry tetrahydrofuran (THF) under an inert atmosphere. 12 mL of dry pyridine was also added, and the solution was cooled to 25°C using a water bath. Next, 22.44 g (144.5 mmol) of cis-4-tert-butylcyclohexylamine was added to the solution, followed by 200 mL of anhydrous THF. The solution was stirred at room temperature for 23 hours. The THF was then removed by rotary evaporation, and 300 mL of methanol was added to the crude product. The methanol / product slurry was added to 2.5 L of stirred deionized (DI) water. The resulting mixture was stirred for 15 minutes, and the solid was collected by suction filtration. The collected solid was rinsed with 200 mL of DI water, after which the solid was slurried in DI water (2 x 1500 mL x 20 min) and collected by filtration. The crude product was then slurried in methanol (3 x 700 mL x 60 min) and collected by suction filtration. The isolated solid was then dried in a vacuum oven at 85°C for 23 hours. The reaction yielded 27.52 g (87.8%) of a fine white powder, which was N,N-bis(cis-4-(tert-butyl)cyclohexyl)-5-nitroisophthalamide.

[0053]

[0031] 13.50 g (27.80 mmol) of N,N-bis(cis-4-(tert-butyl)cyclohexyl)-5-nitroisophthalamide was hydrogenated in a THF / MeOH mixture (1000 mL / 300 mL) with 0.96 g of Pd / C (10 wt%). A 2 L Parr reactor was closed and purged with nitrogen four times and with hydrogen five times while stirring. The hydrogenation was carried out at 40°C and 90 psig hydrogen pressure for 24 hours. The reaction mixture was transferred to a flask under an inert atmosphere and filtered through a Whatman binder-free glass microfiber filter (2.7 μm) to remove the catalyst from the reaction mass. The THF / MeOH solvent mixture was removed by rotary evaporation, and the solid was slurried in diethyl ether (200 mL) for 1 hour and collected by suction filtration. Additional solid was collected from the diethyl ether filtrate. The combined solids were dried for 8 hours in a vacuum oven at 65° C. Hydrogenation gave 12.27 g (96.8%) of 5-amino-N,N-bis(cis-4-(tert-butyl)cyclohexyl)isophthalamide.

[0054]

[0032] 6.08 g (13.34 mmol) of the 5-amino-N,N-bis(cis-4-(tert-butyl)cyclohexyl)isophthalamide obtained above was added to 600 mL of dry tetrahydrofuran (THF) under an inert atmosphere. 1.3 mL of dry pyridine was added, and the solution was cooled to 15°C using an ice-water bath. Next, 2.98 g (14.7 mmol) of cis-4-tert-butylcyclohexanecarboxylic acid chloride was added. The reaction mixture was stirred at 15°C for 0.5 hours and then at 21°C for 21 hours. Approximately 400 mL was removed by rotary evaporation, after which 150 mL of acetone was added to the reaction slurry and stirred for 15 minutes. The reaction slurry was then added to a beaker containing 3000 mL of DI water with stirring. After complete addition of the slurry, the system was stirred for 10 minutes, and the product was collected by suction filtration. The solid was rinsed with 200 mL of DI water and reslurried in 1600 mL of an 80 / 20 solution of DI water / MeOH for 15 minutes. The solid was then collected by suction filtration. The crude product was reslurried in 300 mL of isopropyl alcohol for 1 hour and collected by suction filtration. The resulting solid was dried in a vacuum oven at 95°C for 17 hours. The reaction yielded 7.54 g (90.8%) of N,N-di(cis-4-tert-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide.

[0055] Example 2 This example illustrates the synthesis of the trisamide compounds of the present invention (ie, the trisamide compounds of formula (I)).

[0056]

[0034] 13.50 g (54.45 mmol) of 5-nitroisophthaloyl dichloride was added to 500 mL of dry THF under an inert atmosphere. 10.2 mL of dry pyridine was also added, and the solution was cooled to 25°C using a water bath. Next, 18.60 g (119.8 mmol) of cis-4-sec-butylcyclohexylamine was added to the solution, followed by 200 mL of anhydrous THF. The solution was stirred at room temperature for 23 hours. The THF was then removed by rotary evaporation, and 300 mL of IPA was added to the crude product. The IPA / product slurry was added to 2.8 L of stirred DI water. The resulting mixture was stirred for 20 minutes, and the solid was collected by suction filtration. The collected solid was rinsed with 1000 mL of DI water, after which the solid was slurried in 250 mL of IPA at 5°C for 60 minutes and collected by filtration. The crude product was then rinsed with 100 mL of diethyl ether at −78° C. The isolated solid was then dried in a vacuum oven at 85° C. for 23 hours. The reaction yielded 22.57 g (85.4%) of a fine white powder, which was N,N-bis(cis-4-(sec-butyl)cyclohexyl)-5-nitroisophthalamide.

[0057]

[0035] 22.57 g (46.47 mmol) of the N,N-bis(cis-4-(sec-butyl)cyclohexyl)-5-nitroisophthalamide obtained above was hydrogenated in a THF / MeOH mixture (1000 mL / 300 mL) using 1.60 g of Pd / C (10 wt %). A 2 L Parr reactor was closed and purged with nitrogen four times and with hydrogen five times while stirring. The hydrogenation was carried out at 40 °C and 90 psig hydrogen pressure for 24 h. The reaction mixture was transferred to a flask under an inert atmosphere and filtered through a Whatman binder-free glass microfiber filter (2.7 μm) to remove the catalyst from the reaction mass. The THF / MeOH solvent mixture was removed by rotary evaporation, and the solid was slurried in IPA (200 mL) for 45 minutes and filtered. The collected solid was then rinsed with 75 mL of diethyl ether at -78 °C. Additional solids were collected from the diethyl ether filtrate. The combined solids were dried in a vacuum oven at 45° C. for 18 hours. The reaction yielded 19.45 g (91.8%) of 5-amino-N,N-bis(cis-4-(sec-butyl)cyclohexyl)isophthalamide.

[0058] 9.64 g (21.16 mmol) of the 5-amino-N,N-bis(cis-4-(sec-butyl)cyclohexyl)isophthalamide obtained above was added to 900 mL of dry tetrahydrofuran (THF) under an inert atmosphere. 2.1 mL of dry pyridine was added, and the solution was cooled to 15°C using an ice-water bath. Next, 4.72 g (23.28 mmol) of cis-4-tert-butylcyclohexanecarboxylic acid chloride was added. The reaction mixture was stirred at 15°C for 0.5 hours and then at 21°C for 21 hours. Approximately 600 mL was removed by rotary evaporation, after which 150 mL of acetone was added to the reaction slurry and stirred for 15 minutes. The reaction slurry was then added to a beaker containing 2500 mL of DI water with stirring. After complete addition of the slurry, the system was stirred for 10 minutes, and the product was collected by suction filtration. The solid was rinsed with 200 mL of DI water and reslurried in 1200 mL of a 75 / 25 solution of DI water / IPA for 90 minutes. The solid was then collected by suction filtration. The crude product was reslurried in 300 mL of IPA at 5°C for 30 minutes and collected by suction filtration. The resulting solid was dried in a vacuum oven at 110°C for 17 hours. The reaction yielded 12.65 g (96.1%) of N,N-di(cis-4-sec-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide.

[0059] Example 3 This example illustrates the production of a polymer composition according to the present invention and the properties of such a polymer composition.

[0060] Twenty trisamide compounds were initially synthesized according to the general procedure described above and shown in Examples 1 and 2. These trisamide compounds are listed below in Table 1. To simplify comparison of the various compounds, the trisamide compounds all had similar cis content.

[0061] [Table 1]

[0062] Polymer compositions were prepared by compounding each trisamide compound with a 12 MFR polypropylene random copolymer (SA849 RCP manufactured by LyondellBasell). Each trisamide compound (i.e., compounds 1-20) was gravimetrically added to polymer pellets (0.80 grams of powder additive per 1000 grams of additive / polymer mixture, yielding 800 ppm of trisamide compound) and then mixed in a Henschel high-intensity mixer. The resulting mixture was melt-compounded at 260°C in a Deltaplast single-screw compounding extruder with a screw diameter of 25 mm and a length / diameter ratio of 30:1. The extrudate (in the form of strands) of each sample was cooled in a water bath and subsequently pelletized. The melt-blended polymer composition was then injection molded using a 40-ton Arburg Allrounder 221K injection molding machine at a flat profile barrel temperature of 260°C and 100 bar back pressure to produce plaques measuring approximately 51 mm x 76 mm and having a thickness of 0.76 mm. After aging for 24 hours, the plaque dimensions were verified with a micrometer.

[0063] The percent haze of the plaques (including a control plaque made without the trisamide compound) was then measured using BYK-Gardner Haze-Guard Plus according to ASTM standard D1103-92.

[0064] The plaques were also tested using a set of conditions to determine the amount of trisamide compound extracted. Specifically, extractions were performed at 100°C for 2 hours using a 550 mL stainless steel vessel lined with Teflon and with a stainless steel lid. A glass spacer was used to ensure separation of the polymer samples during the migration test. Extractions were performed using a 25% ethanol solution. The ethanol was anhydrous grade. Water was obtained by deionization using an ion-exchange purification system. Dual migration tests in solvent were performed using two plaques immersed in 250 mL of solvent. Control plaques were also prepared without the trisamide compound and extracted using the conditions described above. Aliquots (approximately 1 mL) were removed from the extraction solvent after each heating period into vials for LC analysis.

[0065] A 1000 ppm solution of each trisamide compound was prepared by dissolving 0.100 g in NMP, and dilutions were made with 100% ethanol. These solutions were used to obtain calibration plots for each trisamide compound. A Water ACQUITY UPLC with a Phenomenex Kinetex (2.6 μm particle size) analytical column and both PDA and MS detectors was used as the LC system. The column temperature was 40°C. The mobile phase used was methanol and water. The flow rate was set at 0.4 mL / min. The sample injection volume ranged from 1 to 5 μL. The mass spectrometer was operated in single ion recording (SIR) mode using an SQD2 detector. The wavelength of the PDA detector was set at 200 to 800 nm. Each trisamide compound was identified by comparison of its retention time with the corresponding peak in the standard solution, as well as by its MS and UV spectra. Quantitation was performed using the calibration plots of external standards. The limit of detection (LOD) was determined by extrapolation to a signal-to-noise ratio of 3:1.

[0066] The results of the haze and extraction measurements are shown below in Table 2. In the column for the amount extracted, the designation "ND" means "not detected" and indicates that the amount (if any) of extracted trisamide compound could not be quantified because the measurement did not return a signal above the limit of detection (LOD) noted above.

[0067] [Table 2]

[0068] As can be seen from the data in Table 2, R 1 , R 2 , and R 3 The polymer compositions prepared using the trisamide compounds of formula (I) in which each is an alkyl group (i.e., the polymer compositions prepared using compounds 2 to 18) are 1 , R 2 , and R 3 The compositions prepared using trisamide compounds in which at least one of the R groups is a non-alkyl group (i.e., polymer compositions prepared using compounds 1, 19, and 20) exhibited a desirable combination of low haze and extractability. 1 , R 2 and R 3 The difference in extraction levels is even more pronounced when the group is an alkyl group having two or more carbon atoms (e.g., a C or higher alkyl). 1 , R 2 and R 3 When at least one of the groups was a branched alkyl group, haze and extractable levels were consistently lower, and desirable performance generally increased with increasing number of branched alkyl groups.

[0069]

[0045] Based on the above, the inventors believe that the trisamide compounds of the present invention are exceptionally superior due to their highly desirable combination of low haze and low extractables. Polymer compositions made with such trisamide compounds will be suitable for a wide range of applications requiring polymer compositions exhibiting low haze and extractable levels, such as food contact and medical device applications.

[0070]

[0046] All references, including publications, patent applications, and patents, cited herein are incorporated by reference to the same extent as if each reference was individually and specifically indicated to be incorporated by reference and were set forth in its entirety herein.

[0071]

[0047] In the context of describing the subject matter of this application (particularly in the context of the claims below), the use of the terms "a," "an," and "the" and similar referents should be construed to encompass both the singular and the plural, unless otherwise indicated herein or clearly contradicted by context. The terms "comprising," "having," "including," and "containing" should be construed as open-ended terms (i.e., meaning "including, but not limited to"), unless otherwise noted. The recitation of ranges of values ​​herein is merely intended to serve as a shorthand method of individually referring to each separate value falling within the range, unless otherwise indicated herein, and each separate value is incorporated herein as if it were individually listed herein. All methods described herein can be performed in any suitable order, unless otherwise indicated herein or clearly contradicted otherwise by context. The use of any and all examples or exemplary language (e.g., "for example") provided herein is intended merely to better clarify the subject matter of the present application and does not limit the scope of the subject matter unless otherwise claimed. No language herein should be construed as indicating any non-claimed element as essential to the practice of the subject matter described herein.

[0072] Preferred embodiments of the subject matter of this application are described herein, including the best mode known to the inventors for carrying out the claimed subject matter. Variations of these preferred embodiments may become apparent to those of skill in the art upon reading the foregoing description. The inventors expect that skilled artisans will utilize these variations as appropriate, and the inventors intend that the subject matter described herein may be practiced otherwise than as specifically described herein. Accordingly, this disclosure includes all modifications and equivalents of the subject matter recited in the claims appended hereto as permitted by applicable law. Furthermore, any combination of the above-described elements in all possible variations thereof is encompassed by this disclosure unless otherwise indicated herein or otherwise clearly contradicted by context.

Claims

1. Formula (I) 【Chemical 1】 [In the formula, R １ , R ２ , and R ３ are independently selected from the group consisting of alkyl groups.

2. R １ , R ２ , and R ３ But C １ ~C ８ 2. The compound of claim 1, wherein each of the groups is independently selected from the group consisting of alkyl groups.

3. R １ , R ２ , and R ３ 3. The compound of claim 1 or claim 2, wherein at least one of the following groups is a branched alkyl group:

4. R ３ The compound of claim 3 , wherein is a branched alkyl group.

5. R １ , R ２ , and R ３ 5. The compound of claim 3 or claim 4, wherein at least two of are branched alkyl groups.

6. R １ , R ２ , and R ３ The compound of claim 5 , wherein each of is a branched alkyl group.

7. The compound is N,N-di(4-isopropylcyclohexyl)-5-(4-n-propylcyclohexylcarbonylamino)isophthalamide; N,N-di(4-isopropylcyclohexyl)-5-(4-isopropylcyclohexylcarbonylamino)isophthalamide; N,N-di(4-isopropylcyclohexyl)-5-(4-n-butylcyclohexylcarbonylamino)isophthalamide; N,N-di(4-isopropylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)isophthalamide; N,N-di(4-isopropylcyclohexyl)-5-(4-n-pentylcyclohexylcarbonylamino)isophthalamide; N,N-di(4-isopropylcyclohexyl)-5-(4-tert-pentylcyclohexylcarbonylamino)isophthalamide; N,N-di(4-n-butylcyclohexyl)-5-(4-n-butylcyclohexylcarbonylamino)isophthalamide; N,N-di(4-n-butylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)isophthalamide; N,N-di(4-sec-butylcyclohexyl)-5-(4-sec-butylcyclohexylcarbonylamino)isophthalamide; N,N-di(4-sec-butylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)isophthalamide; N,N-di(4-tert-butylcyclohexyl)-5-(4-n-propylcyclohexylcarbonylamino)isophthalamide; N,N-di(4-tert-butylcyclohexyl)-5-(4-isopropylcyclohexylcarbonylamino)isophthalamide; N,N-di(4-tert-butylcyclohexyl)-5-(4-n-butylcyclohexylcarbonylamino)isophthalamide; N,N-di(4-tert-butylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)isophthalamide; N,N-di(4-tert-butylcyclohexyl)-5-(4-n-pentylcyclohexylcarbonylamino)isophthalamide; N,N-di(4-tert-pentylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)isophthalamide; N,N-di(4-tert-pentylcyclohexyl)-5-(4-tert-pentylcyclohexylcarbonylamino)isophthalamide; 10. The compound of claim 1 selected from the group consisting of: and mixtures thereof.

8. The compound of claim 7, wherein the compound is N,N-di(4-tert-butylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)isophthalamide.

9. The compound of claim 7, wherein the compound is N,N-di(4-tert-butylcyclohexyl)-5-(4-isopropylcyclohexylcarbonylamino)isophthalamide.

10. The compound of claim 7, wherein the compound is N,N-di(4-tert-butylcyclohexyl)-5-(4-n-butylcyclohexylcarbonylamino)isophthalamide.

11. The compound of claim 7, wherein the compound is N,N-di(4-tert-pentylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)isophthalamide.

12. 8. The compound of claim 7, wherein the compound is N,N-di(4-tert-butylcyclohexyl)-5-(4-n-propylcyclohexylcarbonylamino)isophthalamide.

13. The compound of claim 7, wherein the compound is N,N-di(4-isopropylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)isophthalamide.

14. The compound of claim 7, wherein the compound is N,N-di(4-tert-pentylcyclohexyl)-5-(4-tert-pentylcyclohexylcarbonylamino)isophthalamide.

15. The compound of claim 7, wherein the compound is N,N-di(4-isopropylcyclohexyl)-5-(4-n-butylcyclohexylcarbonylamino)isophthalamide.

16. The compound of claim 7, wherein the compound is N,N-di(4-isopropylcyclohexyl)-5-(4-n-pentylcyclohexylcarbonylamino)isophthalamide.

17. The compound of claim 7, wherein the compound is N,N-di(4-tert-butylcyclohexyl)-5-(4-n-pentylcyclohexylcarbonylamino)isophthalamide.

18. The compound of claim 7, wherein the compound is N,N-di(4-isopropylcyclohexyl)-5-(4-tert-pentylcyclohexylcarbonylamino)isophthalamide.

19. The compound of claim 7, wherein the compound is N,N-di(4-isopropylcyclohexyl)-5-(4-n-propylcyclohexylcarbonylamino)isophthalamide.

20. The compound of claim 7, wherein the compound is N,N-di(4-n-butylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)isophthalamide.

21. The compound of claim 7, wherein the compound is N,N-di(4-n-butylcyclohexyl)-5-(4-n-butylcyclohexylcarbonylamino)isophthalamide.

22. The compound of claim 7, wherein the compound is N,N-di(4-sec-butylcyclohexyl)-5-(4-sec-butylcyclohexylcarbonylamino)isophthalamide.

23. The compound of claim 7, wherein the compound is N,N-di(4-sec-butylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)isophthalamide.

24. (a) a compound according to any one of claims 1 to 23; (b) a polyolefin polymer; A polymer composition comprising:

25. 25. The polymer composition of claim 24, wherein the polyolefin polymer is a polypropylene polymer.

26. 26. The polymer composition of claim 25, wherein the polyolefin polymer is selected from the group consisting of polypropylene homopolymer, polypropylene random copolymer, and mixtures thereof.

27. 27. The polymer composition of claim 26, wherein the polyolefin polymer is a polypropylene random copolymer.

28. 28. The polymer composition of any one of claims 24 to 27, wherein said compound of formula (I) is present in said composition in an amount of about 0.001 wt% or greater, based on the total weight of said polymer composition.

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