Trisamide compounds and compositions containing trisamide compounds

Abstract

To provide clarifying agents that can both produce desirably low haze levels in polyolefin polymers and exhibit minimal extraction from the polyolefin polymer to which they are added and to provide polymer compositions incorporating such clarifying agents and which exhibit the desired combination of low haze and minimal extraction of the clarifying agent.SOLUTION: There are provided trisamide derivatives formally derived from 5-aminoisophthalic acid, for example, N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-n-propylcyclohexylcarbonylamino)isophthalamide.SELECTED DRAWING: None

Description

Technical Field

[0001]

[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 various fields, among other things, due to their excellent processability, mechanical properties (especially on a relative weight basis), and electrical properties. Although the polymer itself may have beneficial properties, additives may also be used to further enhance the properties of the polymer and / or to mitigate disadvantages.

[0002]

[0003] Polyolefins are a particularly versatile group of polymer resins. Polyolefins are semi-crystalline polymers. Relatively slowly cooled polyolefins (such as the cooling that occurs during the manufacture 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 generally aligned in domains called "crystalline lamellae". Under normal processing conditions, as the polyolefin polymer cools from the molten state, the crystalline lamellae grow radially in all directions. This radial growth results in the formation of spherulites, which are spherical semi-crystalline regions composed of multiple crystalline lamellae blocked by amorphous regions. The size of the spherulites is affected by several parameters and can range from several hundred nanometers to several millimeters in diameter. When the spherulite size is much larger than the wavelength of visible light, the spherulites scatter the visible light passing through the polymer. This scattering of visible light results in a cloudy appearance generally referred to as "polymer haze" or simply "haze". In some applications, a fairly high level of polymer haze may be acceptable, but there are certain applications (such as storage containers) where consumers desire relatively transparent plastics, and accordingly, a low haze level is required.

[0003]

[0004] Over the years, several approaches have been developed to reduce haze in polyolefins. One approach that has achieved much commercial success involves the use of clarifying agents. Clarifying agents are additives (often organic compounds) that, when melt processed with a polymer, form nuclei for crystallization of the polymer being cooled, reducing the spherulite size and even substantially preventing the formation of these effective light-scattering objects. For example, bis(3,4-dimethylbenzylidene)sorbitol has achieved much commercial success because it can 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 by bis(3,4-dimethylbenzylidene)sorbitol limits the use and end use of those 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) were initially regarded as promising because the fact that relatively low amounts of such compounds can provide haze levels in polypropylene polymers comparable to those achieved by bis(3,4-dimethylbenzylidene)sorbitol. Despite their initial promise, the disclosed trisamide compounds still cannot provide haze levels comparable to those of more transparent polymers. Furthermore, many of the disclosed trisamide compounds may be extracted from the polypropylene to which they are added. These undesirable levels of extraction render such trisamide compounds less suitable for use in food contact and medical applications (i.e., applications where polymers clarified with trisamide compounds come into contact with food [e.g., food storage or packaging] or are used in medical devices [e.g., syringes]) where additives showing minimal extraction from the polymer are required by industry preferences and / or regulatory requirements.

[0005]

[0006] Accordingly, there is a need for a clarifying agent that can provide both a desirably low haze level in polyolefin polymers and minimal extraction from the polyolefin polymer to which the clarifying agent is added. There is also a need for a polymer composition incorporating such a clarifying agent and showing the desired combination of low haze and minimal extraction of the clarifying agent. The various aspects 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]

Chemical formula

[0007] [wherein, R 1 , R 2 , and R 3 are independently selected from the group consisting of alkyl groups] to provide a compound.

[0008]

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

[0009]

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

[0010]

Chemical formula

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

[0012]

[0010] R 1 , R 2 , and R 3 groups can be any suitable alkyl group. In a preferred embodiment, R 1 , R 2 , and R 3 are C1-C 20 alkyl groups (e.g., C3-C 20 alkyl groups), more preferably C1-C 12 alkyl groups (e.g., C3-C 12(an alkyl group), more preferably a C1-C8 alkyl group (e.g., a C3-C8 alkyl group), and most preferably a C1-C5 alkyl group (e.g., a C2-C5 alkyl group or a C3-C5 alkyl group), and is independently selected from the group consisting of. Suitable alkyl groups can be either straight-chain or branched. In a preferred embodiment, R 1 , R 2 , and R 3 is at least one of which is a branched alkyl group. R 1 , R 2 , and R 3 If only one of them is a branched alkyl group, R 3 is preferably a branched alkyl group. R 1 , R 2 and R 3 In another embodiment where only one of them is a branched alkyl group, R 1 is preferably a branched alkyl group. In another preferred embodiment, R 1 , R 2 , and R 3 are at least two of which are independently selected branched alkyl groups. In one such embodiment, R 1 and R 2 are preferably independently selected branched alkyl groups. In another such embodiment, R 2 and R 3 are preferably independently selected branched alkyl groups. In yet another preferred embodiment, R 1 , R 2 , and R 3 Each of which is an independently selected branched alkyl group. In these embodiments containing a branched alkyl group, the alkyl group can contain any suitable number of carbon atoms, and preferred examples are C3-C 20 branched alkyl group, C3-C 12 branched alkyl group, C3-C8 branched alkyl group, and C3-C5 branched alkyl group. Suitable branched alkyl groups preferably contain a branch point located at the alpha or beta carbon with respect to the cyclohexanediyl moiety.

[0013]

[0011] In a preferred embodiment, R 1 , R 2 , and R 3 are 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 are 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]

[0012] As described above, R1 , R 2 and R 3 At least one of them is preferably a branched alkyl group. Thus, in a preferred embodiment, R 1 , R 2 and R 3 At least one of them 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. In another preferred embodiment, R 1 , R 2 and R 3 At least one of them 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). In a more preferred embodiment, R 1 , R 2 and R 3 At least one of them 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). In yet another preferred embodiment, R1 , R 2 , and R 3 at least one of which 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). In a preferred embodiment, R 3 is a branched alkyl group selected from one of the groups described in this paragraph. In another preferred embodiment, R 2 and R 3 are each a branched alkyl group independently selected from one of the groups described in this paragraph. In yet another preferred embodiment, each of R 1 , R 2 and R 3 is a branched alkyl group independently selected from one of the groups described in this paragraph.

[0015]

[0013] 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-bis(4-n-butylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)isophthalamide; (ix) N,N-bis(4-sec-butylcyclohexyl)-5-(4-sec-butylcyclohexylcarbonylamino)isophthalamide; (x) N,N-bis(4-sec-butylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)isophthalamide; (xi) N,N-bis(4-tert-butylcyclohexyl)-5-(4-n-propylcyclohexylcarbonylamino)isophthalamide; (xii) N,N-bis(4-tert-butylcyclohexyl)-5-(4-isopropylcyclohexylcarbonylamino)isophthalamide; (xiii) N,N-bis(4-tert-butylcyclohexyl)-5-(4-n-butylcyclohexylcarbonylamino)isophthalamide; (xiv) N,N-bis(4-tert-butylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)isophthalamide (xv) N,N-bis(4-tert-butylcyclohexyl)-5-(4-n-pentylcyclohexylcarbonylamino)isophthalamide; (xvi) N,N-bis(4-tert-pentylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)isophthalamide; (xvii) N,N-bis(4-tert-pentylcyclohexyl)-5-(4-tert-pentylcyclohexylcarbonylamino)isophthalamide; and (xviii) selected from the group consisting of these mixtures (i.e., mixtures of any two or more of the aforementioned compounds).

[0016] In another preferred embodiment, the compound is (i) N,N - bis(4 - isopropylcyclohexyl)-5-(4 - tert - butylcyclohexylcarbonylamino)isophthalamide; (ii) N,N - bis(4 - isopropylcyclohexyl)-5-(4 - tert - pentylcyclohexylcarbonylamino)isophthalamide; (iii) N,N - bis(4 - n - butylcyclohexyl)-5-(4 - tert - butylcyclohexylcarbonylamino)isophthalamide; (iv) N,N - bis(4 - sec - butylcyclohexyl)-5-(4 - sec - butylcyclohexylcarbonylamino)isophthalamide; (v) N,N - bis(4 - sec - butylcyclohexyl)-5-(4 - tert - butylcyclohexylcarbonylamino)isophthalamide; (vi) N,N - bis(4 - tert - butylcyclohexyl)-5-(4 - n - propylcyclohexylcarbonylamino)isophthalamide; (vii) N,N - bis(4 - tert - butylcyclohexyl)-5-(4 - isopropylcyclohexylcarbonylamino)isophthalamide; (viii) N,N - bis(4 - tert - butylcyclohexyl)-5-(4 - tert - butylcyclohexylcarbonylamino)isophthalamide; (ix) N,N - bis(4 - tert - pentylcyclohexyl)-5-(4 - tert - butylcyclohexylcarbonylamino)isophthalamide; (x) N,N - bis(4 - tert - pentylcyclohexyl)-5-(4 - tert - pentylcyclohexylcarbonylamino)isophthalamide; and (xi) It is selected from the group consisting of these mixtures (i.e., mixtures of any two or more of the aforementioned 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 is substituted at both the 1- and 4-positions with non-hydrogen substituents (i.e., the R 1 、R 2 、or R 3 groups and the amide-substituted benzene moiety). The non-hydrogen substituents attached to each cyclohexanediyl moiety can be arranged in two different spatial arrangements relative to each other. Both non-hydrogen substituents can be present on the same side of the mean plane of the cyclohexane ring, which corresponds to the cis configuration, or both non-hydrogen substituents can be present on opposite sides of the mean plane of the cyclohexane ring, which corresponds to the trans configuration. Each of the R 1 、R 2 、and R 3 groups can be arranged either cis or trans to the non-hydrogen substituent attached to the 1-position of the corresponding cyclohexanediyl moiety. In a preferred embodiment, R 1 、R 2 、and R 3At least one of the groups is disposed cis to a non-hydrogen substituent attached to the 1-position of the corresponding cyclohexanediyl moiety. In another preferred embodiment, R 1 R 2 and R 3 at least two of the groups are disposed cis to a non-hydrogen substituent attached to the 1-position of the corresponding cyclohexanediyl moiety. In yet another preferred embodiment, R 1 R 2 and R 3 each of the groups is disposed cis to a non-hydrogen substituent attached to the 1-position of the corresponding cyclohexanediyl moiety.

[0019]

[0015] 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 - bis(cis - 4 - n - butylcyclohexyl)-5-(cis - 4 - tert - butylcyclohexylcarbonylamino)isophthalamide; (ix) N,N - bis(cis - 4 - sec - butylcyclohexyl)-5-(cis - 4 - sec - butylcyclohexylcarbonylamino)isophthalamide; (x) N,N - bis(cis - 4 - sec - butylcyclohexyl)-5-(cis - 4 - tert - butylcyclohexylcarbonylamino)isophthalamide; (xi) N,N - bis(cis - 4 - tert - butylcyclohexyl)-5-(cis - 4 - n - propylcyclohexylcarbonylamino)isophthalamide; (xii) N,N - bis(cis - 4 - tert - butylcyclohexyl)-5-(cis - 4 - isopropylcyclohexylcarbonylamino)isophthalamide; (xiii) N,N - bis(cis - 4 - tert - butylcyclohexyl)-5-(cis - 4 - n - butylcyclohexylcarbonylamino)isophthalamide; (xiv) N,N - bis(cis - 4 - tert - butylcyclohexyl)-5-(cis - 4 - tert - butylcyclohexylcarbonylamino)isophthalamide (xv) N,N - bis(cis - 4 - tert - butylcyclohexyl)-5-(cis - 4 - n - pentylcyclohexylcarbonylamino)isophthalamide; (xvi) N,N - bis(cis - 4 - tert - pentylcyclohexyl)-5-(cis - 4 - tert - butylcyclohexylcarbonylamino)isophthalamide; (xvii) N,N - bis(cis - 4 - tert - pentylcyclohexyl)-5-(cis - 4 - tert - pentylcyclohexylcarbonylamino)isophthalamide; and (xviii) It is selected from the group consisting of these mixtures (i.e., mixtures of any two or more of the aforementioned compounds).

[0020] In another preferred embodiment, the compound is (i) N,N - bis(cis - 4 - isopropylcyclohexyl) - 5 - (cis - 4 - tert - butylcyclohexylcarbonylamino)isophthalamide; (ii) N,N - bis(cis - 4 - isopropylcyclohexyl) - 5 - (cis - 4 - tert - pentylcyclohexylcarbonylamino)isophthalamide; (iii) N,N - bis(cis - 4 - n - butylcyclohexyl) - 5 - (cis - 4 - tert - butylcyclohexylcarbonylamino)isophthalamide; (iv) N,N - bis(cis - 4 - sec - butylcyclohexyl) - 5 - (cis - 4 - sec - butylcyclohexylcarbonylamino)isophthalamide; (v) N,N - bis(cis - 4 - sec - butylcyclohexyl) - 5 - (cis - 4 - tert - butylcyclohexylcarbonylamino)isophthalamide; (vi) N,N - bis(cis - 4 - tert - butylcyclohexyl) - 5 - (cis - 4 - n - propylcyclohexylcarbonylamino)isophthalamide; (vii) N,N - bis(cis - 4 - tert - butylcyclohexyl) - 5 - (cis - 4 - isopropylcyclohexylcarbonylamino)isophthalamide; (viii) N,N - bis(cis - 4 - tert - butylcyclohexyl) - 5 - (cis - 4 - tert - butylcyclohexylcarbonylamino)isophthalamide; (ix) N,N - bis(cis - 4 - tert - pentylcyclohexyl) - 5 - (cis - 4 - tert - butylcyclohexylcarbonylamino)isophthalamide; (x) N,N - bis(cis - 4 - tert - pentylcyclohexyl) - 5 - (cis - 4 - tert - pentylcyclohexylcarbonylamino)isophthalamide; and (xi) It is selected from the group consisting of these mixtures (i.e., mixtures of any two or more of the aforementioned 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] This 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 different compounds, and thus, a mixture of two or more isomers constitutes a composition containing a mixture of two or more compounds of formula (I)). In such embodiments, it is preferred that more than 60% of the R 1 , R 2 , and R 3 groups of all the compounds of formula (I) present in the composition are in the cis position relative to the non-hydrogen substituent attached to the 1-position of the corresponding cyclohexanediyl moiety. More preferably, the R 1 , R 2 , and R 3More than about 65% of the base is in the cis position relative to the non-hydrogen substituent bonded to the 1-position of the corresponding cyclohexanediyl moiety. In another preferred embodiment, all of the compounds of formula (I) present in the composition have R 1 , R 2 , and R 3 groups such that more than about 70% of them are in the cis position relative to the non-hydrogen substituent bonded to the 1-position of the corresponding cyclohexanediyl moiety. In yet another preferred embodiment, all of the compounds of formula (I) present in the composition have R 1 , R 2 , and R 3 groups such that more than about 75% of them are in the cis position relative to the non-hydrogen substituent bonded to the 1-position of the corresponding cyclohexanediyl moiety. In another preferred embodiment, all of the compounds of formula (I) present in the composition have R 1 , R 2 , and R 3 groups such that more than about 80% of them are in the cis position relative to the non-hydrogen substituent bonded to the 1-position of the corresponding cyclohexanediyl moiety. In yet another preferred embodiment, all of the compounds of formula (I) present in the composition have R 1 , R 2 , and R 3 groups such that 85% or more of them are in the cis position relative to the non-hydrogen substituent bonded to the 1-position of the corresponding cyclohexanediyl moiety. In another preferred embodiment, all of the compounds of formula (I) present in the composition have R 1 , R 2 , and R 3 groups such that more than about 90% of them are in the cis position relative to the non-hydrogen substituent bonded to the 1-position of the corresponding cyclohexanediyl moiety. In yet another preferred embodiment, all of the compounds of formula (I) present in the composition have R 1 , R 2 , and R 3 groups such that more than about 95% (e.g., more than about 96%, more than about 97%, more than about 98%, or more than about 99%) of them are in the cis position relative to the non-hydrogen substituent bonded to the 1-position of the corresponding cyclohexanediyl moiety.

[0023] In another preferred embodiment of a composition containing a mixture of two or more compounds of formula (I), at least about 60 mol% of the compounds of formula (I) present in the composition are each in the cis position with respect to the non-hydrogen substituent bonded to the 1-position of the corresponding cyclohexanediyl moiety, R 1 , R 2 , and R 3 groups. More preferably, at least about 65 mol% of the compounds of formula (I) present in the composition are each in the cis position with respect to the non-hydrogen substituent bonded to the 1-position of the corresponding cyclohexanediyl moiety, R 1 , R 2 , and R 3 groups. In yet another preferred embodiment, at least about 70 mol% of the compounds of formula (I) present in the composition are each in the cis position with respect to the non-hydrogen substituent bonded to the 1-position of the corresponding cyclohexanediyl moiety, R 1 , R 2 , and R 3 groups. In another preferred embodiment, at least about 75 mol% of the compounds of formula (I) present in the composition are each in the cis position with respect to the non-hydrogen substituent bonded to the 1-position of the corresponding cyclohexanediyl moiety, R 1 , R 2 , and R 3 groups. In yet another preferred embodiment, at least about 80 mol% of the compounds of formula (I) present in the composition are each in the cis position with respect to the non-hydrogen substituent bonded to the 1-position of the corresponding cyclohexanediyl moiety, R 1 , R 2 , and R 3 groups. In another preferred embodiment, at least about 85 mol% of the compounds of formula (I) present in the composition are each in the cis position with respect to the non-hydrogen substituent bonded to the 1-position of the corresponding cyclohexanediyl moiety, R 1 , R 2 , and R 3 groups. In yet another preferred embodiment, at least about 90 mol% of the compounds of formula (I) present in the composition are each in the cis position with respect to the non-hydrogen substituent bonded to the 1-position of the corresponding cyclohexanediyl moiety, R 1 , R 2 , and R 3has a base. In another preferred embodiment, at least about 95 mol% (e.g., at least about 96 mol%, at least about 97 mol%, at least about 98 mol%, or at least about 99 mol%) of the compound of formula (I) present in the composition is in the cis position with respect to the non-hydrogen substituent attached to the 1-position of the corresponding cyclohexanediyl moiety for each of R 1 , R 2 , and R 3 groups.

[0024]

[0018] The compounds of formula (I) can be produced using any suitable method or synthetic process. For example, the compound can be prepared by first reacting the desired 4-alkylcyclohexylamine with 5-nitroisophthaloyl dichloride to form the following intermediate compound of formula (A)

[0025]

Chemical formula

[0026] which can then be hydrogenated using known methods to form the corresponding amine compound of formula (B)

[0027]

Chemical formula

[0028] . The desired compound of formula (I) can then be formed by reacting the amine compound of formula (B) with the desired 4-alkylcyclohexanecarbonyl chloride.

[0029]

[0019] Compounds of formula (I) in which R 1 and R 2 are different can be prepared, for example, by reacting 5-nitroisophthalic acid monoalkyl ester (e.g., 5-nitroisophthalic acid monomethyl ester) with oxalyl chloride to form the following intermediate compound of formula (J)

[0030]

Chemical formula

[0031] [In the formula, R 11 is an alkyl group, for example, a methyl group], can be produced by producing an acid chloride compound. Next, the acid chloride compound of formula (J) is reacted with a desired 4-alkylcyclohexylamine to obtain the following formula (K)

[0032]

Chemical formula

[0033] intermediate compound can be produced. Next, the intermediate compound of formula (K) is saponified with an appropriate base (for example, lithium hydroxide) to obtain the corresponding carboxylate (for example, lithium salt of carboxylic acid) and alcohol (that is, alcohol having the structure R 11 OH, when R 11 is methyl, such methanol). Next, the corresponding carboxylate is hydrolyzed with an appropriate acid (for example, hydrochloric acid) to obtain the following formula (L)

[0034]

Chemical formula

[0035] acid can be produced. Next, the acid of formula (L) is reacted with oxalyl chloride to obtain the following formula (M)

[0036]

Chemical formula

[0037] corresponding acid chloride compound can be obtained. Next, the acid chloride of formula (M) is reacted with a desired 4-alkylcyclohexylamine to obtain the following formula (N)

[0038]

Chemical formula

[0039] An intermediate compound of the formula (N) can be produced. Next, the intermediate compound of the formula (N) is reduced using a known method (for example, hydrogenation) to give the following formula (O)

[0040]

Chemical formula

[0041] The corresponding diamine compound can be produced. Finally, the intermediate compound of the formula (O) is reacted with a desired 4-alkylcyclohexanecarbonyl chloride to obtain the desired compound of the formula (I).

[0042]

[0020] In a second aspect, the present invention provides a polymer composition comprising a compound of the formula (I) and a polymer. In such an aspect, the compound of the formula (I) can be any of the aspects discussed above in connection with the first aspect of the present invention (for example, a composition containing a specific compound or a mixture of compounds).

[0043]

[0021] 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, polyethylene polymer, polymethylpentene polymer (e.g., poly(4-methyl-1-pentene)), polybutylene polymer, poly(vinylcyclohexane) polymer, and mixtures 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 homopolymers, isotactic polypropylene homopolymers, and syndiotactic polypropylene homopolymers), polypropylene copolymers (e.g., polypropylene random copolymers), polypropylene impact copolymers, and mixtures thereof. Suitable polypropylene copolymers include, but are not limited to, random copolymers made 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 typically is present in an amount of less than about 10 wt% (e.g., about 1 to about 7 wt%). 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 plastomers to a polypropylene homopolymer or polypropylene random copolymer. In such polypropylene impact copolymers, the copolymer can be present in any suitable amount, but typically is present in an amount of about 5 to about 25 wt%.In a preferred embodiment, the polymer composition comprises a polyolefin polymer selected from the group consisting of polypropylene homopolymers, polypropylene random copolymers, and mixtures thereof. More preferably, the polymer composition comprises a polypropylene random copolymer.

[0044]

[0022] 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 contains at least 0.001% by weight of the compound of formula (I) based on the total weight of the composition. In another preferred embodiment, the polymer composition contains at least 0.002% by weight, at least 0.003% by weight, at least 0.004% by weight, at least 0.005% by weight, at least 0.01% by weight, at least 0.02% by weight, at least 0.03% by weight, at least 0.04% by weight, at least 0.05% by weight, at least 0.1% by weight, at least 0.3% by weight, at least 0.5% by weight, at least 1% by weight, at least 5% by weight, or at least 10% by weight of the compound of formula (I) based on the total weight of the composition. In another embodiment, the polymer composition preferably contains less than 99% by weight of the compound of formula (I) based on the total weight of the composition. In another preferred embodiment, the polymer composition contains less than 95% by weight, less than 80% by weight, less than 50% by weight, less than 25% by weight, less than 10% by weight, less than 5% by weight, less than 2% by weight, less than 1% by weight, less than 0.5% by weight, less than 0.2% by weight, less than 0.1% by weight, or less than 0.07% by weight of the compound of formula (I) based on the total weight of the composition. In a series of particularly preferred embodiments, the polymer composition contains 0.001% to 0.5% by weight (for example, 0.01% to 0.5% by weight or 0.05% to 0.5% by weight), 0.001% to 0.2% by weight (for example, 0.01% to 0.2% by weight or 0.05% to 0.2% by weight), 0.001% to 0.1% by weight (for example, 0.01% to 0.1% by weight or 0.05% to 0.1% by weight), or 0.001% to 0.07% by weight (for example, 0.01% to 0.07% by weight) of the compound of formula (I) based on the total weight of the composition. As described above, the polymer composition of the present invention can contain a plurality of compounds of formula (I). In these embodiments where the polymer composition contains a plurality of trisamide compounds of formula (I), each trisamide compound can be present in an amount within one of the ranges listed above, or the combined amount of all trisamide compounds can be within one of the ranges listed above.

[0045]

[0023] The polymer compositions described herein can contain other polymer additives in addition to the compounds of formula (I). Suitable additional polymer additives include antioxidants (e.g., phenolic antioxidants, phosphite antioxidants, and combinations thereof), antiblocking agents (e.g., amorphous silica and diatomaceous earth), pigments (e.g., organic pigments and inorganic pigments) and other colorants (e.g., dyes and polymer colorants), fillers and reinforcing agents (e.g., glass, glass fibers, 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 of fluoropolymers), polymer crosslinking agents, slip agents (e.g., fatty acid amide compounds derived from the reaction of fatty acids with ammonia or amine-containing compounds), fatty acid ester compounds (e.g., fatty acid ester compounds derived from the reaction of fatty acids with hydroxyl-containing compounds such as glycerin, diglycerol, and combinations thereof), and combinations of the foregoing, but are not limited thereto.

[0046]

[0024] 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 components. Alternatively, an additive composition containing a compound of formula (I) and any additional optional components (e.g., those described above) can be pre-blended to provide a pre-blended composition. This pre-blended 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 further processing to manufacture articles. For example, the polymer composition can be provided in the form of a powder (e.g., a free-flowing powder), flakes, pellets, granules, tablets, agglomerates, etc.

[0047] The polymer compositions described herein are considered useful for manufacturing thermoplastic articles. The polymer compositions can be formed into the desired thermoplastic articles by any suitable technique, such as injection molding, injection rotational molding, 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, rotational molding, film blowing (inflation film), film casting (cast film), etc.

[0048] The polymer compositions described herein can be used to manufacture any suitable article or product. Suitable products include, but are not limited to, medical devices (e.g., prefilled syringes for retort use, intravenous supply containers, and blood collection devices), food packaging, liquid containers (e.g., containers for beverages, drugs, personal care compositions, shampoos, etc.), garment cases, microwaveable articles, shelf materials, cabinet doors, machine parts, automotive parts, sheets, pipes, tubes, rotational molding parts, blow molding parts, films, fibers, etc.

[0049]

[0027] The polymer compositions of the present invention have been found to exhibit a highly desirable combination of low haze and low extraction of the trisamide compounds of formula (I). Polymer compositions containing a compound of formula (I) (e.g., a polypropylene random copolymer composition) generally exhibit a haze level that is at least 15% lower than the haze levels exhibited by polymer compositions containing structurally similar trisamide compounds not encompassed by formula (I). Furthermore, it has been found that polymer compositions containing certain compounds of formula (I) exhibit single-digit haze levels comparable to those exhibited by more transparent polymers, such as polystyrene and acrylic polymers. As described above, these polymer compositions also exhibit extremely good (i.e., low) extraction of the compounds of formula (I) from the polymer compositions. Indeed, it has been found that polymer compositions containing certain compounds of formula (I) exhibit extraction levels that are one to two orders of magnitude lower than the extraction levels exhibited by polymer compositions containing structurally similar trisamide compounds not encompassed by formula (I). Due to these properties exhibited by the polymer compositions of the present invention, the polymer compositions are considered to be particularly well-suited for use in the manufacture of thermoplastic articles or products that require low haze levels and low extraction, such as articles and products for food contact and medical applications.

[0050]

[0028] The following examples further illustrate the above-described subject matter, but should of course not be construed as limiting the scope in any way.

[0051] Example 1

[0029] This example shows the synthesis of the trisamide compound of the present invention (i.e., the trisamide compound 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-butylcyclohexyl-amine was added to the solution, followed by 200 mL of anhydrous THF. The solution was stirred at room temperature for 23 hours. Thereafter, the THF was 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 washed with 200 mL of DI water and then the solid was slurried with DI water (2 × 1500 mL × 20 minutes) and collected by filtration. Next, the crude product was slurried in methanol (3 × 700 mL × 60 minutes) and collected by suction filtration. Next, the isolated solid was dried in a vacuum oven at 85 °C for 23 hours. The reaction gave 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) using 0.96 g of Pd / C (10 wt%). A 2 L Parr reactor was closed and purged four times with nitrogen and five times with hydrogen while stirring. The hydrogenation was carried out at 40 °C and a hydrogen pressure of 90 psig 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 in a vacuum oven at 65 °C for 8 hours. 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-butylcyclohexanecarbonyl chloride was added. The reaction mixture was stirred at 15 °C for 0.5 h and then at 21 °C for 21 h. Approximately 400 mL was removed by rotary evaporation, and then 150 mL of acetone was added to the reaction slurry and stirred for 15 min. Next, the reaction slurry was added to a beaker containing 3000 mL of DI water while stirring. Once the slurry was completely added, the system was stirred for 10 min and the product was collected by suction filtration. The solid was washed with 200 mL of DI water and slurried again in 1600 mL of an 80 / 20 solution of DI water / MeOH for 15 min. Next, the solid was collected by suction filtration. The crude product was slurried again in 300 mL of isopropyl alcohol for 1 h and collected by suction filtration. The resulting solid was dried in a vacuum oven at 95 °C for 17 h. 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

[0033] This example shows the synthesis of the trisamide compound of the present invention (i.e., the trisamide compound 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. Thereafter, the THF was 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 washed with 1000 mL of DI water and then the solid was slurried in 250 mL of IPA at 5 °C for 60 minutes and collected by filtration. Next, the crude product was washed with 100 mL of diethyl ether at -78 °C. Next, the isolated solid was 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 using 1.60 g of Pd / C (10 wt%) in a THF / MeOH mixture (1000 mL / 300 mL). A 2 L Parr reactor was closed, purged four times with nitrogen and five times with hydrogen while stirring. The hydrogenation was carried out at 40 °C and a hydrogen pressure of 90 psig 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 IPA (200 mL) for 45 minutes and filtered. Next, the collected solid was washed with 75 mL of diethyl ether at -78 °C. Further solid was collected from the diethyl ether filtrate. The combined solids were dried in a vacuum oven at 45 °C for 18 hours. The reaction gave 19.45 g (91.8%) of 5-amino-N,N-bis(cis-4-(sec-butyl)cyclohexyl)isophthalamide.

[0058]

[0036] 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-butylcyclohexanecarbonyl chloride was added. The reaction mixture was stirred at 15 °C for 0.5 h and then at 21 °C for 21 h. Approximately 600 mL was removed by rotary evaporation and then 150 mL of acetone was added to the reaction slurry and stirred for 15 min. Next, the reaction slurry was added to a beaker containing 2500 mL of DI water with stirring. Once the slurry was completely added, the system was stirred for 10 min and the product was collected by suction filtration. The solid was rinsed with 200 mL of DI water and slurried again in 1200 mL of a 75 / 25 solution of DI water / IPA for 90 min. Next, the solid was collected by suction filtration. The crude product was slurried again in 300 mL of IPA at 5 °C for 30 min and collected by suction filtration. The resulting solid was dried in a vacuum oven at 110 °C for 17 h. The reaction gave 12.65 g (96.1%) of N,N-di(cis-4-sec-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide.

[0059] Example 3

[0037] This example shows the production of the polymer composition according to the present invention and the properties of such polymer compositions.

[0060]

[0038] According to the basic procedures described above and shown in Examples 1 and 2, 20 trisamide compounds were first synthesized. These trisamide compounds are listed in Table 1 below. To simplify the comparison of the various compounds, all the trisamide compounds had a similar cis content.

[0061]

Table 1

[0062]

[0039] The polymer compositions were prepared by compounding each trisamide compound into a 12 MFR polypropylene random copolymer (SA849 RCP from LyondellBasell). The trisamide compounds (i.e., Compounds 1 - 20) were each added by weight measurement to the polymer pellets (0.80 grams of powder additive per 1000 grams of additive / polymer mixture to obtain 800 ppm of the 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 having 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. Next, the melt-compounded polymer composition was injection-molded using a 40-ton ARBURG ALLROUNDER 221K injection molding machine at a barrel temperature of 260 °C with a flat profile and a back pressure of 100 bar to produce plaques having dimensions of approximately 51 mm x 76 mm and a thickness of 0.76 mm. After aging for 24 hours, the plaque dimensions were verified with a micrometer.

[0063]

[0040] Next, the percent haze of the plaques (including control plaques made without the trisamide compound) was measured using a BYK-Gardner Haze-Guard Plus in accordance with ASTM standard D1103-92.

[0064]

[0041] The plaque was also tested using a predetermined set of conditions to determine the amount of the extracted trisamide compound. In particular, the extraction was carried out at 100 °C for 2 hours using a 550 mL stainless steel container lined with Teflon® and having a stainless steel lid. A glass spacer was used to ensure separation of the polymer sample during the migration test. The extraction was carried out using a 25% ethanol solution. The ethanol was of anhydrous grade. The water was deionized using an ion exchange purification system. The double migration test in the solvent was carried out using two plaques immersed in 250 mL of the solvent. A control plaque was also prepared without using the trisamide compound and extracted using the conditions described above. An aliquot (about 1 mL) was taken from the extraction solvent into a vial for LC analysis after each heating time.

[0065]

[0042] A 1000 ppm solution of each trisamide compound was prepared by dissolving 0.100 g in NMP, and the dilutions were prepared in 100% ethanol. Using these solutions, calibration plots were obtained for each trisamide compound. A Waters ACQUITY UPLC was used as the LC apparatus, with a Phenomenex Kinetex (particle size 2.6 μm) as the analytical column and both a PDA and an MS as detectors. The column temperature was 40 °C. The mobile phases used were methanol and water. The flow rate was set at 0.4 mL / min. The sample injection volume was 1 - 5 μL. The mass spectrometer was used in single ion recording (SIR) mode using an SQD2 detector. The wavelength in the PDA detector was set from 200 - 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. Quantification was carried out using a calibration plot of an external standard. The limit of detection (LOD) was determined by extrapolation to a signal-to-noise ratio of 3:1.

[0066]

[0043] The results of the haze and extraction measurements are shown in Table 2 below. In the column of the extracted amount, the indication of "N.D." means "not detected", indicating that the measurement did not return a signal exceeding the above detection limit (LOD), and thus the amount of the trisamide compound extracted (if any) could not be quantified.

[0067]

Table 2

[0068]

[0044] As can be seen from the data in Table 2, the polymer compositions prepared using the trisamide compounds of formula (I) in which R 1 、R 2 、and R 3 are each an alkyl group (i.e., the polymer compositions prepared using Compounds 2 to 18) showed a desirable combination of low haze and extraction as compared with the compositions prepared using the trisamide compounds in which at least one of R 1 、R 2 、and R 3 is a non-alkyl group (i.e., the polymer compositions prepared using Compounds 1, 19, and 20). When the R 1 、R 2 and R 3 groups of the trisamide compound are alkyl groups having two or more carbon atoms (e.g., alkyl of C3 or higher), the difference in the extraction level is even more significant. Further, when at least one of R 1 、R 2 and R 3 is a branched alkyl group, the haze and extraction levels are consistently lower, and the desirable performance generally became higher as the number of branched alkyl groups increased.

[0069]

[0045] From the above, the inventors believe that the trisamide compounds of the present invention are particularly excellent due to their highly desirable combination of low haze and low extraction. Polymer compositions made with such trisamide compounds would be suitable for a wide range of applications (e.g., food contact and medical device applications) that require polymer compositions exhibiting low haze levels and extraction levels.

[0070]

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

[0071]

[0047] The terms "a," "an," and "the," and similar referents used in the context of describing the subject matter of this application (especially in the context of the following claims) are to be construed to include both the singular and the plural unless otherwise indicated herein or clearly contradicted by the context. The terms "comprising," "having," "including," and "containing" are to 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 convenient method of referring individually to each separate value falling within the range, and each separate value is hereby incorporated herein as if it were individually recited herein. All methods described herein can be performed in any suitable order unless otherwise indicated herein or otherwise clearly contradicted by the context. The use of any and all examples, or exemplary language (e.g., "such as") provided herein is merely intended to better illuminate the subject matter of this application and does not limit the scope of the subject matter unless otherwise claimed. No term in this specification is to be construed as indicating any non-claimed element as essential to the practice of the subject matter described herein.

[0072]

[0048] 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 skilled in the art upon reading the foregoing description. The inventors expect those skilled in the art to utilize these variations as appropriate, and the inventors intend for the subject matter recited herein to 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. Further, any combination of the above-described elements in all possible variations thereof is included by this disclosure unless otherwise indicated herein or otherwise clearly contradicted by context.

Claims

1. Formula (I) 【Chemistry 1】 [In the formula, R １ , R ２ , and R ３ is independently selected from the group consisting of alkyl groups; R １ , R ２ , and R ３ at least one of the groups is positioned cis relative to the non-hydrogen substituent attached to the 1-position of the corresponding cyclohexanediyl moiety.

2. R １ , R ２ , and R ３ 2. The compound of claim 1, wherein at least two of the groups are positioned cis relative to a non-hydrogen substituent attached to the 1-position of the corresponding cyclohexanediyl moiety.

3. R １ , R ２ , and R ３ 3. The compound of claim 2, wherein each of the groups is positioned cis relative to the non-hydrogen substituent attached to the 1-position of the corresponding cyclohexanediyl moiety.

4. R １ , R ２ , and R ３ But, C １ ~C ８ 4. The compound of claim 3, wherein each of the groups is independently selected from the group consisting of alkyl groups.

5. R １ , R ２ , and R ３ The compound of claim 4, wherein at least one of the following is a branched alkyl group:

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

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

8. R １ , R ２ , and R ３ The compound of claim 7, wherein each of is a branched alkyl group.

9. The compound is N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-n-propylcyclohexylcarbonylamino)isophthalamide; N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-isopropylcyclohexylcarbonylamino)isophthalamide; N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-n-butylcyclohexylcarbonylamino)isophthalamide; N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide; N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-n-pentylcyclohexylcarbonylamino)isophthalamide; N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-tert-pentylcyclohexylcarbonylamino)isophthalamide; N,N-di(cis-4-n-butylcyclohexyl)-5-(cis-4-n-butylcyclohexylcarbonylamino)isophthalamide; N,N-di(cis-4-n-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide; N,N-di(cis-4-sec-butylcyclohexyl)-5-(cis-4-sec-butylcyclohexylcarbonylamino)isophthalamide; N,N-di(cis-4-sec-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide; N,N-di(cis-4-tert-butylcyclohexyl)-5-(cis-4-n-propylcyclohexylcarbonylamino)isophthalamide; N,N-di(cis-4-tert-butylcyclohexyl)-5-(cis-4-isopropylcyclohexylcarbonylamino)isophthalamide; N,N-di(cis-4-tert-butylcyclohexyl)-5-(cis-4-n-butylcyclohexylcarbonylamino)isophthalamide; N,N-di(cis-4-tert-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide; N,N-di(cis-4-tert-butylcyclohexyl)-5-(cis-4-n-pentylcyclohexylcarbonylamino)isophthalamide; N,N-di(cis-4-tert-pentylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide; N,N-di(cis-4-tert-pentylcyclohexyl)-5-(cis-4-tert-pentylcyclohexylcarbonylamino)isophthalamide; 4. The compound of claim 3 selected from the group consisting of:

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

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

12. The compound of claim 9, wherein the compound is N,N-di(cis-4-tert-butylcyclohexyl)-5-(cis-4-n-butylcyclohexylcarbonylamino)isophthalamide.

13. The compound of claim 9, wherein the compound is N,N-di(cis-4-tert-pentylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide.

14. 10. The compound of claim 9, wherein the compound is N,N-di(cis-4-tert-butylcyclohexyl)-5-(cis-4-n-propylcyclohexylcarbonylamino)isophthalamide.

15. 10. The compound of claim 9, wherein the compound is N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide.

16. The compound of claim 9, wherein the compound is N,N-di(cis-4-tert-pentylcyclohexyl)-5-(cis-4-tert-pentylcyclohexylcarbonylamino)isophthalamide.

17. The compound of claim 9, wherein the compound is N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-n-butylcyclohexylcarbonylamino)isophthalamide.

18. The compound of claim 9, wherein the compound is N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-n-pentylcyclohexylcarbonylamino)isophthalamide.

19. The compound of claim 9, wherein the compound is N,N-di(cis-4-tert-butylcyclohexyl)-5-(cis-4-n-pentylcyclohexylcarbonylamino)isophthalamide.

20. The compound of claim 9, wherein the compound is N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-tert-pentylcyclohexylcarbonylamino)isophthalamide.

21. The compound of claim 9, wherein the compound is N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-n-propylcyclohexylcarbonylamino)isophthalamide.

22. The compound of claim 9, wherein the compound is N,N-di(cis-4-n-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide.

23. The compound of claim 9, wherein the compound is N,N-di(cis-4-n-butylcyclohexyl)-5-(cis-4-n-butylcyclohexylcarbonylamino)isophthalamide.

24. The compound of claim 9, wherein the compound is N,N-di(cis-4-sec-butylcyclohexyl)-5-(cis-4-sec-butylcyclohexylcarbonylamino)isophthalamide.

25. The compound of claim 9, wherein the compound is N,N-di(cis-4-sec-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide.

26. (a) a compound according to any one of claims 1 to 25; (b) a polyolefin polymer; 1. A polymer composition comprising:

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

28. 28. The polymer composition of claim 27, wherein the polyolefin polymer is selected from the group consisting of polypropylene homopolymer, polypropylene random copolymer, and mixtures thereof.

29. 30. The polymer composition of claim 28, wherein the polyolefin polymer is a polypropylene random copolymer.

30. 27. The polymer composition of claim 26, wherein said compound of formula (I) is present in said composition in an amount of 0.001 wt. % or more, based on the total weight of said polymer composition.

31. 31. The polymer composition of claim 30, wherein said compound of formula (I) is present in said composition in an amount ranging from 0.001% to 0.5% by weight relative to the total weight of said polymer composition.

32. 32. The polymer composition of claim 31, wherein said compound of formula (I) is present in said composition in an amount ranging from 0.01% to 0.2% by weight relative to the total weight of said polymer composition.

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