Trisamide compounds and compositions containing trisamide compounds

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]

[0001] This application relates to trisamide compounds (specifically, trisamide derivatives formally derived from 5-aminoisophthalic acid) and compositions comprising trisamide compounds. Background of the Invention

[0002] Polymer resins are widely used in various fields due to their excellent processability, mechanical properties (especially on a relative weight basis), and electrical properties. While polymers themselves may possess beneficial properties, additives may be used to further enhance the polymer's properties and / or mitigate its drawbacks.

[0002]

[0003] Polyolefins are a particularly versatile group of polymer resins. Polyolefins are semi-crystalline polymers. When polyolefins are cooled relatively slowly (for example, during the manufacturing of molded plastic parts), they contain amorphous regions where polymer chains are randomly arranged and crystalline regions where 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 normal processing conditions, as the polyolefin polymer cools from a 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 obscured by amorphous regions. The size of the spherulites is influenced by several parameters and can range from several hundred nanometers to several millimeters in diameter. If the spherulite size is considerably larger than the wavelength of visible light, the spherulites scatter visible light passing through the polymer. This scattering of visible light produces a cloudy appearance commonly referred to as "polymer haze" or simply "haze." While a considerable level of polymer haze may be acceptable for some applications, there are specific uses where consumers desire relatively transparent plastics (e.g., storage containers), and therefore require lower haze levels.

[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 clearing agents. Clearing agents are additives (often organic compounds) that, when melt-processed with a polymer, form nuclei for crystallization of 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 achieved much commercial success because it can reduce haze in polypropylene polymers. However, bis(3,4-dimethylbenzylidene)sorbitol was not without its limitations. In particular, clearing agents cannot reduce the haze in polypropylene polymers to a level comparable to that of more transparent polymers, such as polystyrene and acrylic resins. The residual haze in polymers cleared with bis(3,4-dimethylbenzylidene)sorbitol limits the applications and end uses of those polymers.

[0004]

[0005] To address the limitations of sorbitol acetals (e.g., bis(3,4-dimethylbenzylidene)sorbitol), other clearing 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 seen as promising due to the fact that relatively low amounts of such compounds could result in haze levels in polypropylene polymers comparable to those achieved by bis(3,4-dimethylbenzylidene)sorbitol. Despite their initial prospects, the disclosed trisamide compounds still fail to produce haze levels comparable to those of more clear 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 where the trisamide-cleared polymer comes into contact with food [e.g., food storage or packaging] or in medical devices [e.g., syringes]) where industrial preferences and / or regulatory requirements demand additives that exhibit minimal extraction from the polymer.

[0005]

[0006] Therefore, there is a need for a clearing agent that can both provide a desirable low haze level in polyolefin polymers and exhibit minimal extraction from the polyolefin polymer to which the clearing agent is added. There is also a need for polymer compositions that incorporate such a clearing agent and exhibit the desired combination of low haze and minimal extraction of the clearing agent. The various embodiments described herein aim to provide such clearing agents and compositions. Brief summary of the invention

[0007] In a first embodiment, the present invention relates to 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.] A compound is provided.

[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] The 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 12A C1-C8 alkyl group (e.g., a C3-C8 alkyl group) is independently selected from the group consisting of alkyl groups, more preferably C1-C5 alkyl groups (e.g., C2-C5 alkyl groups or C3-C5 alkyl groups). A suitable alkyl group may be linear or branched. In a preferred embodiment, R 1 , R 2 , and R 3 At least one of them is a branched alkyl group. 1 , R 2 , and R 3 If only one of them is a branched alkyl group, then R 3 R is preferably a branched alkyl group. 1 , R 2 and R 3 In another embodiment, R 1 is preferably a branched alkyl group. In another preferred embodiment, R 1 , R 2 , and R 3 At least two of these are independently selected branched alkyl groups. In one such embodiment, R 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 Each of these 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, a preferred example being C3-C3. 20 Branched alkyl groups, C3~C 12 These are branched alkyl groups, C3-C8 branched alkyl groups, and C3-C5 branched alkyl groups. A suitable branched alkyl group preferably contains a branch point located at the alpha or beta carbon relative to the cyclohexanediyl moiety.

[0013]

[0011] 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., butane-2-yl or 1-methylpropyl), isobutyl (i.e., 2-methylpropyl), tert-butyl (i.e., 1,1-dimethylethyl), n-pentyl, tert-pentyl (i.e., 2-methylbutane-2-yl or 1,1-dimethylpropyl), neopentyl (i.e., 2,2-dimethylpropyl), isopentyl (i.e., 3-methylbutyl), sec-pentyl (i.e., pentane-2-yl or 1-methylbutyl), sec-isopentyl (i.e., 3-methylbutane-2-yl or 1,2-dimethylpropyl), pentane-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., butane-2-yl or 1-methylpropyl), isobutyl (i.e., 2-methylpropyl), tert-butyl (i.e., 1,1-dimethylethyl), tert-pentyl (i.e., 2-methylbutane-2-yl or 1,1-dimethylpropyl), sec-pentyl (i.e., pentane-2-yl or 1-methylbutyl), sec-isopentyl (i.e., 3-methylbutane-2-yl or 1,2-dimethylpropyl), and pentane-3-yl (i.e., 1-ethylpropyl). In yet another preferred embodiment, R 1 , R 2 , and R 3 The compound is 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. Therefore, 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., butane-2-yl or 1-methylpropyl), isobutyl (i.e., 2-methylpropyl), tert-butyl (i.e., 1,1-dimethylethyl), tert-pentyl (i.e., 2-methylbutane-2-yl or 1,1-dimethylpropyl), neopentyl (i.e., 2,2-dimethylpropyl), isopentyl (i.e., 3-methylbutyl), sec-pentyl (i.e., pentane-2-yl or 1-methylbutyl), sec-isopentyl (i.e., 3-methylbutane-2-yl or 1,2-dimethylpropyl), pentane-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 these 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 these 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 Each of these is a branched alkyl group independently selected from one of the groups described in this paragraph. In yet another preferred embodiment, R 1 , R 2 and R 3 Each of these 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-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 these mixtures (i.e., mixtures of any two or more of the compounds described above).

[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) Selected from the group consisting of these mixtures (i.e., mixtures of any two or more of the compounds described above).

[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 yet 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 yet 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 yet 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 yet 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 yet 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]

[0014] As can be seen in formula (I), each cyclohexanediyl moiety has a non-hydrogen substituent at both the 1st and 4th positions (i.e., R 1 , R 2 , or R 3 It is substituted with a group and an amide-substituted benzene moiety. 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 the cis configuration, or both non-hydrogen substituents can be on opposite sides of the mean plane of the cyclohexane ring, which corresponds to the trans configuration. 1 , R 2 , and R 3 Each group can be positioned either cis or trans relative to the non-hydrogen substituent bonded 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 positioned cis relative to the non-hydrogen substituent bonded 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 positioned cis relative to the non-hydrogen substituent bonded to the 1-position of the corresponding cyclohexanediyl moiety. In yet another preferred embodiment, R 1 , R 2 , and R 3 Each group is positioned in the cis position relative to the non-hydrogen substituent bonded 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-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 these mixtures (i.e., mixtures of any two or more of the compounds described above).

[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) Selected from the group consisting of these mixtures (i.e., mixtures of any two or more of the compounds described above).

[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 yet 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 yet 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 yet 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 yet 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 regard, 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 bonded to the 1-position of the corresponding cyclohexanediyl moiety. More preferably, the R 1 、R 2 、and R 3At least about 65% of the groups 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 at least 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 at least 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 at least 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 at least 85% 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 at least 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 at least about 95% (e.g., at least about 96%, at least about 97%, at least about 98%, or at least 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]

[0017] In another preferred embodiment of a composition containing a mixture of two or more compounds of formula (I), about 60 mol% or more of the compounds of formula (I) present in the composition are R atoms in the cis position relative to the nonhydrogen substituent bonded at position 1 of the corresponding cyclohexanediyl moiety. 1 , R 2 , and R 3 It has a group. More preferably, about 65 mol% or more of the compound of formula (I) present in the composition has R groups at the cis position relative to the nonhydrogen substituent bonded at position 1 of the corresponding cyclohexanediyl moiety. 1 , R 2 , and R 3 It has a group. In yet another preferred embodiment, about 70 mol% or more of the compound of formula (I) present in the composition is R at the cis position relative to the nonhydrogen substituent bonded at position 1 of the corresponding cyclohexanediyl moiety. 1 , R 2 , and R 3 It has a group. In another preferred embodiment, about 75 mol% or more of the compound of formula (I) present in the composition is R at the cis position relative to the nonhydrogen substituent bonded at position 1 of the corresponding cyclohexanediyl moiety. 1 , R 2 , and R 3 It has a group. In yet another preferred embodiment, about 80 mol% or more of the compound of formula (I) present in the composition is R at the cis position relative to the nonhydrogen substituent bonded at position 1 of the corresponding cyclohexanediyl moiety. 1 , R 2 , and R 3 It has a group. In another preferred embodiment, about 85 mol% or more of the compound of formula (I) present in the composition is R at the cis position relative to the nonhydrogen substituent bonded at position 1 of the corresponding cyclohexanediyl moiety. 1 , R 2 , and R 3 It has a group. In yet another preferred embodiment, about 90 mol% or more of the compound of formula (I) present in the composition is R at the cis position relative to the nonhydrogen substituent bonded at position 1 of the corresponding cyclohexanediyl moiety. 1 , R 2 , and R 3It has a group. In 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 compound of formula (I) present in the composition is R at the cis position relative to the nonhydrogen substituent bonded at position 1 of the corresponding cyclohexanediyl moiety. 1 , R 2 , and R 3 It has a base.

[0024]

[0018] Compounds of formula (I) can be produced by any suitable method or synthetic process. For example, the compound can be produced by first reacting the desired 4-alkylcyclohexylamine with 5-nitroisophthaloyl dichloride to obtain the compound of formula (A) below.

[0025] [ka]

[0026] It can be produced by generating an intermediate compound of the following. Next, the intermediate compound of formula (A) is hydrogenated using a known method to obtain the following formula (B).

[0027] [ka]

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

[0029]

[0019] R 1 and R 2 Compounds of formula (I) that differ from the following are obtained by reacting monoalkyl 5-nitroisophthalate (e.g., monomethyl 5-nitroisophthalate) with oxalyl chloride to form the compound of formula (J) below.

[0030] [ka]

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

[0032] [ka]

[0033] An intermediate compound of formula (K) can then be produced. Next, the intermediate compound of formula (K) is saponified with a suitable base (e.g., lithium hydroxide) to obtain the corresponding carboxylate salt (e.g., lithium salt of carboxylic acid) and alcohol (i.e., structure R 11 Alcohols containing OH, R 11 If is methyl, then methanol can be obtained. Next, the corresponding carboxylate salt is hydrolyzed with a suitable acid (for example, hydrochloric acid) to obtain the following formula (L)

[0034] [ka]

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

[0036] [ka]

[0037] The corresponding acid chloride compound of formula (M) can then be obtained by reacting the acid chloride of formula (M) with a desired 4-alkylcyclohexylamine to obtain the following formula (N).

[0038] [ka]

[0039] An intermediate compound of formula (N) can be produced. Next, the intermediate compound of formula (N) can be reduced using a known method (e.g., hydrogenation) to obtain the following formula (O).

[0040] [ka]

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

[0042]

[0020] In a second embodiment, the present invention provides a polymer composition comprising a compound of formula (I) and a polymer. In such an embodiment, the compound of formula (I) may be any of the embodiments discussed above in relation to 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 may contain any suitable polymer. Preferably, the polymer is a thermoplastic polymer, such as polyolefins, polyesters, polyamides, polylactic acid, polycarbonates, acrylic polymers, or mixtures thereof. More preferably, the polymer is a polyolefin polymer, such as 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 homopolymer, isotactic polypropylene homopolymer, and syndiotactic polypropylene homopolymer), polypropylene copolymers (e.g., polypropylene random copolymer), polypropylene impact copolymer, and mixtures thereof. Suitable polypropylene copolymers include, but are not limited to, random copolymers produced by polymerization of propylene in the presence of a comonomer selected from the group consisting of ethylene, buta-1-ene (i.e., 1-butene), and hexa-1-ene (i.e., 1-hexene). In such polypropylene random copolymers, the comonomer may be present in any suitable amount, but is typically present in amounts less than about 10% by weight (e.g., 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 may be present in any suitable amount, but is typically present in amounts about 5 to about 25% by weight.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 may contain any appropriate 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, based on the total weight of the composition, a compound of formula (I) in an amount of 0.001% to 0.5% by weight (e.g., 0.01% to 0.5% by weight or 0.05% to 0.5%), 0.001% to 0.2% by weight (e.g., 0.01% to 0.2% by weight or 0.05% to 0.2%), 0.001% to 0.1% by weight (e.g., 0.01% to 0.1% by weight or 0.05% to 0.1%), or 0.001% to 0.07% by weight (e.g., 0.01% to 0.07%). As described above, the polymer composition of the present invention may contain a plurality of compounds of formula (I). In these embodiments, where the polymer composition comprises multiple trisamide compounds of formula (I), each trisamide compound may be present in an amount that falls within one of the ranges listed above, or the combined amount of all trisamide compounds may fall within one of the ranges listed above.

[0045]

[0023] The polymer compositions described herein may 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 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, clearing agents, acid scavenging agents (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 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, e.g., glycerin, diglycerol, and combinations thereof), and combinations thereof.

[0046]

[0024] The polymer compositions described herein can be produced by any suitable method. For example, a polyolefin composition can be produced by a simple mixture (e.g., a high-shear or high-strength mixture) of a polyolefin polymer, a compound of formula (I), and any additional optional components. Alternatively, a pre-blended composition can be provided by pre-blending an additive composition containing a compound of formula (I) and any additional optional components (e.g., those described above). This pre-blended composition can then be mixed with a polymer to produce the polymer compositions described above. The polymer compositions can be provided in any form suitable for use in further processing for manufacturing articles. For example, the polymer compositions can be provided in the form of powder (e.g., free-flowing powder), flakes, pellets, spheres, tablets, agglomerates, and the like.

[0047]

[0025] The polymer compositions described herein are considered useful for manufacturing thermoplastic articles. The polymer compositions can be molded into 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]

[0026] 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., pre-filled 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.), clothing cases, microwave-safe articles, shelf materials, cabinet doors, machine parts, automotive parts, sheets, pipes, tubes, rotationally molded parts, blow-molded parts, films, fibers, and the like.

[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 trisamide compounds of formula (I). Polymer compositions containing compounds of formula (I) (e.g., polypropylene random copolymer compositions) generally exhibit a haze level at least 15% lower than that shown 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 a haze level of an order of magnitude lower, comparable to that shown by more transparent polymers, such as polystyrene and acrylic polymers. As described above, these polymer compositions also exhibit exceptionally good (i.e., low) extraction of compounds of formula (I) from polymer compositions. In fact, polymer compositions containing specific compounds of formula (I) have been found to exhibit an extraction level one to two orders of magnitude lower than that shown by polymer compositions containing structurally similar trisamide compounds not encompassed by formula (I). These properties demonstrated by the polymer compositions of the present invention suggest that the polymer compositions are particularly well suited for use in the manufacture of thermoplastic articles or products requiring low haze levels and low extractability, such as articles and products for food contact and medical applications.

[0050]

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

[0051] Example 1

[0029] This example demonstrates 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-butylcyclohexylamine was added to the solution, followed by 200 mL of anhydrous THF. The solution was stirred at room temperature for 23 hours. Then, 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. After rinsing the collected solid with 200 mL of DI water, the solid was then made into a slurry with DI water (2 × 1500 mL × 20 mins) and collected by filtration. Next, the crude product was made into a slurry in methanol (3 × 700 mL × 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 four times with nitrogen and five times with hydrogen while stirring. 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 reactants. The THF / MeOH solvent mixture was removed by rotary evaporation, and the solids were slurryed in diethyl ether (200 mL) for 1 hour and collected by suction filtration. Further solids were collected from the diethyl ether filtrate. The combined solids were dried in a vacuum oven at 65°C for 8 hours. Hydrogenation yielded 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 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 stirred at 21°C for 21 hours. Approximately 400 mL was removed by rotary evaporation, and then 150 mL of acetone was added to the reaction slurry and stirred for 15 minutes. 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 minutes, and the product was collected by suction filtration. The solid was rinsed with 200 mL of DI water and then slurryed again in 1600 mL of DI water / MeOH 80 / 20 solution for 15 minutes. The solid was then collected by suction filtration. The crude product was slurryed again 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

[0033] This example demonstrates 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. Then, 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 solids were collected by suction filtration. After rinsing the collected solids with 1000 mL of DI water, the solids were then allowed to form a slurry in 250 mL of IPA at 5°C for 60 minutes and collected by filtration. Next, the crude product was 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 above-mentioned N,N-bis(cis-4-(sec-butyl)cyclohexyl)-5-nitroisophthalamide) was hydrogenated in a THF / MeOH mixture (1000 mL / 300 mL) with 1.60 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. 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 reactants. The THF / MeOH solvent mixture was removed by rotary evaporation, and the solids were slurryed in IPA (200 mL) for 45 minutes and filtered. Next, the collected solids were rinsed with 75 mL of diethyl ether at -78 °C. Further solid material was 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]

[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 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 stirred at 21°C for 21 hours. Approximately 600 mL was removed by rotary evaporation, and then 150 mL of acetone was added to the reaction slurry and stirred for 15 minutes. Next, the reaction slurry was added to a beaker containing 2500 mL of DI water while stirring. Once the slurry was completely added, 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 then slurryed again in 1200 mL of a 75 / 25 DI water / IPA solution for 90 minutes. The solid was then collected by suction filtration. The crude product was slurryed again 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

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

[0060]

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

[0061] [Table 1]

[0062]

[0039] The polymer compositions were prepared by compounding each trisamide compound with 12MFR polypropylene random copolymer (SA849 RCP from LyondellBasell). The trisamide compounds (i.e., compounds 1-20) were each added to the polymer pellets by gravimetric measurement (0.80 grams of powdered additive per 1000 grams of additive / polymer mixture yielded 800 ppm of trisamide compound), and then mixed in a Henschel high-strength mixer. The resulting mixtures were 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 extruded products (in the form of strands) of each sample were cooled in a water bath and then pelletized. Next, the molten 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 a plaque with 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 percentage haze of plaques (including control plaques prepared without the use of trisamide compounds) was measured using BYK-Gardner Haze-Guard Plus in accordance with ASTM standard D1103-92.

[0064]

[0041] Plaques were also tested using a predetermined set of conditions to determine the amount of trisamide compound extracted. In particular, 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. Glass spacers were used to ensure the separation of polymer samples during the migration test. Extraction was performed using a 25% ethanol solution. The ethanol was anhydrous grade. Water was obtained by deionization using an ion exchange purification system. A double migration test in solvent was performed using two plaques immersed in 250 mL of solvent. A control plaque was also prepared without the trisamide compound and extracted using the conditions described above. Aliquots (approximately 1 mL) were taken out of the extraction solvent and placed in vials 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 dilutions were prepared with 100% ethanol. Calibration plots for each trisamide compound were obtained using these solutions. A Water ACQUITY UPLC with both PDA and MS detectors was used as the LC instrument, with a Phenomenex Kinetex (particle size 2.6 μm) as the analytical column. The column temperature was 40°C. The mobile phases used were methanol and water. The flow rate was set to 0.4 mL / min. The sample injection volume was 1-5 μL. The mass spectrometer was used in single-ion recording (SIR) mode with an SQD2 detector. The wavelength in the PDA detector was set to 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 performed using calibration plots of external standards. The limit of detection (LOD) was determined by extrapolation to a 3:1 signal-to-noise ratio.

[0066]

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

[0067] [Table 2]

[0068]

[0044] As can be seen from the data in Table 2, R 1 , R 2 , and R 3 A polymer composition prepared using a trisamide compound of formula (I) in which each of the elements is an alkyl group (i.e., a polymer composition prepared using compounds 2 to 18) is R 1 , R 2 , and R 3 Compared to compositions prepared using trisamide compounds in which at least one of the trisamide compounds is a non-alkyl group (i.e., polymer compositions prepared using compounds 1, 19, and 20), the trisamide compounds showed a desirable combination of low haze and extraction. 1 , R 2 and R 3 When the group is an alkyl group having two or more carbon atoms (for example, an alkyl group with three or more carbon atoms), the difference in extraction levels is even more pronounced. Furthermore, R 1 , R 2 and R 3 When at least one of the elements was a branched alkyl group, haze and extraction levels were consistently lower, and the desired performance generally increased further with increasing numbers of branched alkyl groups.

[0069]

[0045] Based on the above, the inventors believe that the trisamide compounds of the present invention are particularly superior due to their highly desirable combination of low haze and low extraction. Polymer compositions prepared using 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 and extraction levels.

[0070]

[0046] All references cited herein, including publications, patent applications, and patents, are incorporated herein by reference to the same extent as each reference is specifically indicated by reference and is included in whole herein.

[0071]

[0047] In the context describing the subject matter of this application (and in particular in the context of the following claims), the use of the terms “a,” “an,” and “the,” and similar reference subjects, should be interpreted as encompassing both singular and plural, unless otherwise indicated herein or unless clearly inconsistent with the context. The terms “comprising,” “having,” “including,” and “containing” should be interpreted as unrestricted terms unless otherwise noted (i.e., “including, but not limited to these”). The enumeration of ranges of values ​​herein is intended merely as a simple way to refer individually to each distinct value contained within the range, unless otherwise indicated herein, and each distinct value is incorporated herein as if it were enumerated individually. All methods described herein may be carried out in any suitable order, unless otherwise indicated herein or unless clearly inconsistent with the context. The use of any examples or illustrative terms provided herein (e.g., “For example”) is intended solely to better illustrate the subject matter of this application and, unless otherwise claimed, does not limit the scope of the subject matter. No term in this specification should be construed as indicating any unclaimed 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 modes 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 by reading the preceding description. The inventors expect that those skilled in the art will utilize these variations as needed, and the inventors intend that the subject matter described herein will be carried out in ways other than those specifically described herein. Accordingly, this disclosure includes, to the extent permitted by applicable law, all modifications and equivalents of the subject matter enumerated in the claims attached herein. Furthermore, any combination of the elements described herein in all possible variations thereof is encompassed herein unless otherwise indicated herein or unless otherwise clearly inconsistent with the context.

Claims

1. Equation (I) 【Chemistry 1】 A composition comprising two or more compounds, [In the formula, R １ , R ２ , and R ３ Each of the R1, R2, and R3 groups of the compound of formula (I) present in the composition is independently selected from the group consisting of alkyl groups, and at least 60% of the R1, R2, and R3 groups of all the compounds present in the composition are in the cis position relative to the nonhydrogen substituent bonded to the 1 position of the corresponding cyclohexanediyl moiety.

2. R in each compound of formula (I) １ , R ２ , and R ３ However, C １ ~C ８ The composition according to claim 1, independently selected from the group consisting of alkyl groups.

3. R in each compound of formula (I) １ , R ２ , and R ３ The composition according to claim 2, wherein at least one of is a branched alkyl group.

4. R in each compound of formula (I) ３ The composition according to claim 3, wherein the alkyl group is a branched alkyl group.

5. R in each compound of formula (I) １ , R ２ , and R ３ The composition according to claim 3, wherein at least two of them are branched alkyl groups.

6. R in each compound of formula (I) １ , R ２ , and R ３ The composition according to claim 5, wherein the alkyl group is a branched alkyl group.

7. The composition according to claim 1, wherein 75% or more of the R1, R2, and R3 groups of all the compounds of formula (I) present in the composition are located at the cis position relative to the non-hydrogen substituent bonded to the 1 position of the corresponding cyclohexanediyl moiety.

8. The composition according to claim 7, wherein 95% or more of the R1, R2, and R3 groups of all the compounds of formula (I) present in the composition are located at the cis position relative to the non-hydrogen substituent bonded to the 1 position of the corresponding cyclohexanediyl moiety.

9. The composition according to claim 1, wherein one compound of formula (I) is N,N-di(cis-4-tert-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide.

10. The composition according to claim 1, wherein one compound of formula (I) is N,N-di(cis-4-tert-butylcyclohexyl)-5-(cis-4-isopropylcyclohexylcarbonylamino)isophthalamide.

11. The composition according to claim 1, wherein one compound of formula (I) is N,N-di(cis-4-tert-butylcyclohexyl)-5-(cis-4-n-butylcyclohexylcarbonylamino)isophthalamide.

12. The composition according to claim 1, wherein one compound of formula (I) is N,N-di(cis-4-tert-pentylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide.

13. The composition according to claim 1, wherein one compound of formula (I) is N,N-di(cis-4-tert-butylcyclohexyl)-5-(cis-4-n-propylcyclohexylcarbonylamino)isophthalamide.

14. The composition according to claim 1, wherein one compound of formula (I) is N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide.

15. The composition according to claim 1, wherein one compound of formula (I) is N,N-di(cis-4-tert-pentylcyclohexyl)-5-(cis-4-tert-pentylcyclohexylcarbonylamino)isophthalamide.

16. The composition according to claim 1, wherein one compound of formula (I) is N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-n-butylcyclohexylcarbonylamino)isophthalamide.

17. The composition according to claim 1, wherein one compound of formula (I) is N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-n-pentylcyclohexylcarbonylamino)isophthalamide.

18. The composition according to claim 1, wherein one compound of formula (I) is N,N-di(cis-4-tert-butylcyclohexyl)-5-(cis-4-n-pentylcyclohexylcarbonylamino)isophthalamide.

19. The composition according to claim 1, wherein one compound of formula (I) is N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-tert-pentylcyclohexylcarbonylamino)isophthalamide.

20. The composition according to claim 1, wherein one compound of formula (I) is N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-n-propylcyclohexylcarbonylamino)isophthalamide.

21. The composition according to claim 1, wherein one compound of formula (I) is N,N-di(cis-4-n-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide.

22. The composition according to claim 1, wherein one compound of formula (I) is N,N-di(cis-4-n-butylcyclohexyl)-5-(cis-4-n-butylcyclohexylcarbonylamino)isophthalamide.

23. The composition according to claim 1, wherein one compound of formula (I) is N,N-di(cis-4-sec-butylcyclohexyl)-5-(cis-4-sec-butylcyclohexylcarbonylamino)isophthalamide.

24. The composition according to claim 1, wherein one compound of formula (I) is N,N-di(cis-4-sec-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide.

25. The composition according to claim 1, wherein one compound of formula (I) is N,N-di(cis-4-isopropylcyclohexyl)-5-(cis-4-isopropylcyclohexylcarbonylamino)isophthalamide.

26. (a) A composition according to any one of claims 1 to 25, (b) Polyolefin polymer and A polymer composition containing the following:

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

28. The polymer composition according to claim 27, wherein the polyolefin polymer is selected from the group consisting of polypropylene homopolymers, polypropylene random copolymers, and mixtures thereof.

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

30. The polymer composition according to claim 26, wherein the total amount of the compound of formula (I) present in the polymer composition is 0.001% by weight or more relative to the total weight of the polymer composition.

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

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

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