Triamide compounds and compositions comprising the same

Abstract

The triamide compound has the structure of Formula (I) wherein R 1 , R 2 , and R 3 are independently selected from alkyl. The polymeric composition comprises the triamide compound of Formula (I) and a polyolefin polymer. The polymeric composition comprising the triamide compound of Formula (I) exhibits very low haze levels and minimal leaching of the triamide compound.

Description

[0001] This application is a divisional application of Chinese Patent Application No. 202080095912.5 (International Application No. PCT / US2020 / 064958), filed on December 14, 2020, entitled "Triamide Compound and Composition Containing the Triamide Compound", the entire contents of which are incorporated herein by reference. Technical Field

[0002] This application relates to triamide compounds (in particular, triamide derivatives formally derived from 5-aminoisophthalic acid) and compositions comprising said triamide compounds. Background Technology

[0003] Polymer resins are widely used in various fields, especially due to their excellent processing properties, mechanical properties (particularly based on relative weight), and electrical properties. While the polymer itself may possess beneficial properties, additives can be used to further enhance those properties and / or mitigate their drawbacks.

[0004] Polyolefins are a particularly versatile group of polymer resins. Polyolefins are semi-crystalline polymers. Polyolefins, which are allowed to cool relatively slowly (e.g., during the production of molded plastic parts), comprise amorphous regions in which polymer chains are randomly arranged and crystalline regions in which the polymer chains have adopted an ordered configuration. Within these crystalline regions of the polyolefin, the polymer chains are arranged into domains commonly referred to as “crystalline lamellae.” Under normal processing conditions, as the polyolefin polymer cools from its molten state, the crystalline lamellae grow radially in various directions. This radial growth leads to the formation of spherulites, which are spherical semi-crystalline regions composed of multiple crystalline lamellae interrupted by the amorphous regions. The size of the spherulites is influenced by several parameters, and their diameter can range from hundreds of nanometers to millimeters. When the size of the spherulites is significantly larger than the wavelength of visible light, the spherulites will scatter visible light passing through the polymer. This scattering of visible light results in a hazy appearance commonly referred to as “polymer haze” or simply “haze.” While significant levels of polymer haze are acceptable in some applications, in others (e.g., storage containers), consumers require relatively transparent plastics, which necessitates correspondingly low levels of haze.

[0005] Over the years, several methods have been developed to reduce haze in polyolefins. One method that has achieved great commercial success involves the use of clarifying agents. Clarifying agents are additives (usually organic compounds) that, when melt-processed with the polymer, can nucleate the crystals of the cooled polymer and reduce spherulite size or even essentially prevent the formation of these effective light-scattering entities. For example, bis(3,4-dimethylbenzyl)sorbitol has achieved great commercial success for its ability to reduce haze in polypropylene polymers. However, bis(3,4-dimethylbenzyl)sorbitol is not without its limitations. In particular, clarifying agents cannot reduce the haze in polypropylene polymers to levels comparable to those of more transparent polymers such as polystyrene and acrylic resins. The residual haze of polymers clarified with bis(3,4-dimethylbenzyl)sorbitol limits their applications and end uses.

[0006] Other clarifying agents have been developed in an attempt to address the limitations of sorbitol acetals (e.g., bis(3,4-dimethylbenzyl)sorbitol). For example, triamide compounds (e.g., triamide derivatives formally derived from 1,3,5-phenyltriamine, 3,5-diaminobenzoic acid, 5-aminoisophthalic acid, or trimesophthalic acid) initially showed promise because relatively low loadings of these compounds could produce haze levels in polypropylene polymers comparable to those obtained with bis(3,4-dimethylbenzyl)sorbitol. Despite their initial promise, the disclosed triamide compounds still do not produce haze levels comparable to those of more transparent polymers. Furthermore, many of the disclosed triamide compounds may be extracted from the polypropylene to which they are added. These undesirable leaching levels make these triamide compounds unsuitable for food contact and medical applications (i.e., applications where the polymer clarified with the triamide compound comes into contact with food [e.g., food storage or packaging] or is used in medical devices [e.g., syringes]), where industry preferences and / or regulatory requirements necessitate that the additive exhibit minimal leaching from the polymer.

[0007] Therefore, there remains a need for clarifying agents that can produce the desired low haze levels in polyolefin polymers while exhibiting minimal leaching from the polyolefin polymers to which they are added. There also remains a need for polymer compositions that incorporate such clarifying agents and exhibit the desired combination of low haze and minimal clarifying agent leaching. The various embodiments described herein seek to provide such clarifying agents and compositions. Summary of the Invention

[0008] In a first embodiment, the present invention provides a compound of formula (I).

[0009] (I)

[0010]

[0011] Where R 1 R 2 and R 3 It is independently selected from alkyl groups.

[0012] In a second embodiment, the present invention provides a polymer composition comprising a compound of formula (I) and a polyolefin polymer. Detailed Implementation

[0013] In a first embodiment, the present invention provides a compound of formula (I), which is a triamide derivative formally derived from 5-aminoisophthalic acid. The structure of formula (I) is as follows:

[0014] (I)

[0015]

[0016] In formula (I), group R 1 R 2 and R 3 It is independently selected from alkyl groups.

[0017] Group R 1 R 2 and R 3 It can be any suitable alkyl group. In a preferred embodiment, R 1 R 2 and R 3 Independently selected from C1-C 20 Alkyl (e.g., C3-C) 20 Alkyl), more preferably C1-C 12 Alkyl (e.g., C3-C) 12 Alkyl groups, more preferably C1-C8 alkyl groups (e.g., C3-C8 alkyl groups), and most preferably C1-C5 alkyl groups (e.g., C2-C5 alkyl groups or C3-C5 alkyl groups). Suitable alkyl groups can be either linear or branched. In a preferred embodiment, R... 1 R 2 and R 3 At least one of them is a branched alkyl group. If R 1 R 2 and R 3 Only one of them is a branched alkyl group, R 3 Preferably, it is a branched alkyl group. Wherein R... 1 R 2 and R 3 In another embodiment where only one of the alkyl groups is a branched alkyl group, R 1 Preferably, it is a branched alkyl group. In another preferred embodiment, R 1 R 2 and R3 At least two of them are independently selected branched alkyl groups. In one such embodiment, R 1 and R 2 Preferably, it is an independently selected branched alkyl group. In another such embodiment, R 2 and R 3 Preferably, the branched alkyl group is selected independently. In another preferred embodiment, R 1 R 2 and R 3 Each of these is an independently selected branched alkyl group. In those embodiments containing branched alkyl groups, the alkyl group may contain any suitable number of carbon atoms, with preferred examples being C3-C4. 20 Branched alkyl groups, C3-C 12 Branched alkyl groups, C3-C8 branched alkyl groups, and C3-C5 branched alkyl groups. Suitable branched alkyl groups preferably contain a branching point located on the α-carbon or β-carbon relative to the cyclohexane diel moiety.

[0018] In the preferred embodiment, R 1 R 2 and R 3 Independently selected from n-propyl, isopropyl, n-butyl, sec-butyl (i.e., butyl-2-yl or 1-methylpropyl), isobutyl (i.e., 2-methylpropyl), tert-butyl (i.e., 1,1-dimethylethyl), n-pentyl, tert-pentyl (i.e., 2-methylbut-2-yl or 1,1-dimethylpropyl), neopentyl (i.e., 2,2-dimethylpropyl), isopentyl (i.e., 3-methylbutyl), sec-pentyl (i.e., pent-2-yl or 1-methylbutyl), sec-isopentyl (i.e., 3-methylbut-2-yl or 1,2-dimethylpropyl), pent-3-yl (i.e., 1-ethylpropyl), and 2-methylbutyl. In a more preferred embodiment, R 1 R 2 and R 3 Independently selected from n-propyl, isopropyl, n-butyl, sec-butyl (i.e., butyl-2-yl or 1-methylpropyl), isobutyl (i.e., 2-methylpropyl), tert-butyl (i.e., 1,1-dimethylethyl), tert-pentyl (i.e., 2-methylbutyl-2-yl or 1,1-dimethylpropyl), sec-pentyl (i.e., pentyl-2-yl or 1-methylbutyl), sec-isopentyl (i.e., 3-methylbutyl-2-yl or 1,2-dimethylpropyl), and pentyl-3-yl (i.e., 1-ethylpropyl). In another preferred embodiment, R 1 R 2 and R 3 It is independently selected from n-propyl, isopropyl, n-butyl, isobutyl (i.e., 2-methylpropyl), tert-butyl (i.e., 1,1-dimethylethyl) and tert-pentyl (i.e., 2-methylbut-2-yl or 1,1-dimethylpropyl).

[0019] As mentioned above, R 1 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 isopropyl, sec-butyl (i.e., butyl-2-yl or 1-methylpropyl), isobutyl (i.e., 2-methylpropyl), tert-butyl (i.e., 1,1-dimethylethyl), tert-pentyl (i.e., 2-methylbutyl-2-yl or 1,1-dimethylpropyl), neopentyl (i.e., 2,2-dimethylpropyl), isopentyl (i.e., 3-methylbutyl), sec-pentyl (i.e., pent-2-yl or 1-methylbutyl), sec-isopentyl (i.e., 3-methylbutyl-2-yl or 1,2-dimethylpropyl), pent-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 isopropyl, sec-butyl (i.e., butyl-2-yl or 1-methylpropyl), isobutyl (i.e., 2-methylpropyl), tert-butyl (i.e., 1,1-dimethylethyl), tert-pentyl (i.e., 2-methylbutyl-2-yl or 1,1-dimethylpropyl), sec-pentyl (i.e., pentyl-2-yl or 1-methylbutyl), sec-isopentyl (i.e., 3-methylbutyl-2-yl or 1,2-dimethylpropyl), and pentyl-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 isopropyl, isobutyl (i.e., 2-methylpropyl), tert-butyl (i.e., 1,1-dimethylethyl), and tert-pentyl (i.e., 2-methylbut-2-yl or 1,1-dimethylpropyl). In another preferred embodiment, R 1 R 2 and R 3 At least one of them is selected from tert-butyl (i.e., 1,1-dimethylethyl) and tert-pentyl (i.e., 2-methylbut-2-yl or 1,1-dimethylpropyl). In a preferred embodiment, R 3 It is a branched alkyl group selected from one of the groups listed in this paragraph. In another preferred embodiment, R 2 and R 3 Each is a branched alkyl group independently selected from one of the groups listed in this paragraph. In another preferred embodiment, R 1 R 2 and R 3 Each of the groups listed in this paragraph is a branched alkyl group independently selected from one of the groups listed in this paragraph.

[0020] In a preferred embodiment, the compound is selected from:

[0021] (i)N,N-bis(4-isopropylcyclohexyl)-5-(4-n-propylcyclohexylcarbonylamino)-isophthalamide;

[0022] (ii) N,N-bis(4-isopropylcyclohexyl)-5-(4-isopropylcyclohexylcarbonylamino)-isophthalamide;

[0023] (iii) N,N-bis(4-isopropylcyclohexyl)-5-(4-n-butylcyclohexylcarbonylamino)-isophthalamide;

[0024] (iv) N,N-bis(4-isopropylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)-isophthalamide;

[0025] (v)N,N-bis(4-isopropylcyclohexyl)-5-(4-n-pentylcyclohexylcarbonylamino)-isophthalamide;

[0026] (vi)N,N-bis(4-isopropylcyclohexyl)-5-(4-tert-pentylcyclohexylcarbonylamino)-isophthalamide;

[0027] (vii)N,N-bis(4-n-butylcyclohexyl)-5-(4-n-butylcyclohexylcarbonylamino)-isophthalamide;

[0028] (viii) N,N-bis(4-n-butylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)-isophthalamide;

[0029] (ix)N,N-Di(4-sec-butylcyclohexyl)-5-(4-sec-butylcyclohexylcarbonylamino)-isophthalamide;

[0030] (x)N,N-Di(4-sec-butylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)-isophthalamide;

[0031] (xi)N,N-Di(4-tert-butylcyclohexyl)-5-(4-n-propylcyclohexylcarbonylamino)-isophthalamide;

[0032] (xii)N,N-Di(4-tert-butylcyclohexyl)-5-(4-isopropylcyclohexylcarbonylamino)-isophthalamide;

[0033] (xiii)N,N-Di(4-tert-butylcyclohexyl)-5-(4-n-butylcyclohexylcarbonylamino)-isophthalamide;

[0034] (xiv)N,N-Di(4-tert-butylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)-isophthalamide;

[0035] (xv)N,N-Di(4-tert-butylcyclohexyl)-5-(4-n-pentylcyclohexylcarbonylamino)-isophthalamide;

[0036] (xvi)N,N-Di(4-tert-pentylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)-isophthalamide;

[0037] (xvii)N,N-bis(4-tert-pentylcyclohexyl)-5-(4-tert-pentylcyclohexylcarbonylamino)-isophthalamide; and

[0038] (xviii) Mixtures of them (i.e., mixtures of two or more of the aforementioned compounds).

[0039] In another preferred embodiment, the compound is selected from:

[0040] (i)N,N-bis(4-isopropylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)-isophthalamide;

[0041] (ii) N,N-bis(4-isopropylcyclohexyl)-5-(4-tert-pentylcyclohexylcarbonylamino)-isophthalamide;

[0042] (iii) N,N-bis(4-n-butylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)-isophthalamide;

[0043] (iv) N,N-bis(4-sec-butylcyclohexyl)-5-(4-sec-butylcyclohexylcarbonylamino)-isophthalamide;

[0044] (v)N,N-bis(4-sec-butylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)-isophthalamide;

[0045] (vi) N,N-bis(4-tert-butylcyclohexyl)-5-(4-n-propylcyclohexylcarbonylamino)-isophthalamide;

[0046] (vii)N,N-Di(4-tert-butylcyclohexyl)-5-(4-isopropylcyclohexylcarbonylamino)-isophthalamide;

[0047] (viii)N,N-bis(4-tert-butylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)-isophthalamide;

[0048] (ix)N,N-Di(4-tert-pentylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)-isophthalamide;

[0049] (x)N,N-bis(4-tert-pentylcyclohexyl)-5-(4-tert-pentylcyclohexylcarbonylamino)-isophthalamide; and

[0050] (xi) Mixtures of them (i.e., mixtures of two or more of the aforementioned compounds).

[0051] In one preferred embodiment, the compound of formula (I) is N,N-bis(4-tert-butylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)-isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-bis(4-tert-butylcyclohexyl)-5-(4-isopropylcyclohexylcarbonylamino)-isophthalamide. In yet another preferred embodiment, the compound of formula (I) is N,N-bis(4-tert-butylcyclohexyl)-5-(4-n-butylcyclohexylcarbonylamino)-isophthalamide. In yet another preferred embodiment, the compound of formula (I) is N,N-bis(4-tert-pentylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)-isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-bis(4-tert-butylcyclohexyl)-5-(4-n-propylcyclohexylcarbonylamino)-isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-bis(4-isopropylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)-isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-bis(4-tert-pentylcyclohexyl)-5-(4-tert-pentylcyclohexylcarbonylamino)-isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-bis(4-isopropylcyclohexyl)-5-(4-n-butylcyclohexylcarbonylamino)-isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-bis(4-isopropylcyclohexyl)-5-(4-n-pentylcyclohexylcarbonylamino)-isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-bis(4-tert-butylcyclohexyl)-5-(4-n-pentylcyclohexylcarbonylamino)-isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-bis(4-isopropylcyclohexyl)-5-(4-tert-pentylcyclohexylcarbonylamino)-isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-bis(4-isopropylcyclohexyl)-5-(4-n-propylcyclohexylcarbonylamino)-isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-bis(4-n-butylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)-isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-bis(4-n-butylcyclohexyl)-5-(4-n-butylcyclohexylcarbonylamino)-isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-bis(4-sec-butylcyclohexyl)-5-(4-sec-butylcyclohexylcarbonylamino)-isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-bis(4-sec-butylcyclohexyl)-5-(4-tert-butylcyclohexylcarbonylamino)-isophthalamide.

[0052] As can be seen in formula (I), each cyclohexane dimethyl moiety is substituented at both the 1- and 4-positions by non-hydrogen substituents (i.e., R). 1 R 2 Or R 3 The non-hydrogen substituents attached to each cyclohexane dimethyl moiety can be arranged in two different spatial configurations relative to each other. The two non-hydrogen substituents can be located on the same side of the mean plane of the cyclohexane ring, corresponding to the cis configuration; or the two non-hydrogen substituents can be located on opposite sides of the mean surface of the cyclohexane ring, corresponding to the trans configuration. 1 R 2 and R 3 Each of the groups can be arranged in a cis or trans position relative to the non-hydrogen substituent at the 1-position attached to the corresponding cyclohexane diene moiety. In a preferred embodiment, R 1 R 2 and R 3 At least one of the groups is arranged in a cis position relative to the non-hydrogen substituent at the 1-position attached to the corresponding cyclohexane diene moiety. In another preferred embodiment, R 1 R 2 and R 3 At least two of the groups are arranged in a cis position relative to the non-hydrogen substituent at the 1-position attached to the corresponding cyclohexane diene moiety. In another preferred embodiment, R 1 R 2 and R 3 Each of the groups is arranged in cis with respect to the non-hydrogen substituent at the 1-position attached to the corresponding cyclohexane diene moiety.

[0053] In a preferred embodiment, the compound is selected from...

[0054] (i)N,N-bis(cis-4-isopropylcyclohexyl)-5-(cis-4-n-propylcyclohexylcarbonylamino)-isophthalamide;

[0055] (ii) N,N-bis(cis-4-isopropylcyclohexyl)-5-(cis-4-isopropylcyclohexylcarbonylamino)-isophthalamide;

[0056] (iii) N,N-bis(cis-4-isopropylcyclohexyl)-5-(cis-4-n-butylcyclohexylcarbonylamino)-isophthalamide;

[0057] (iv)N,N-bis(cis-4-isopropylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)-isophthalamide;

[0058] (v)N,N-bis(cis-4-isopropylcyclohexyl)-5-(cis-4-n-pentylcyclohexylcarbonylamino)-isophthalamide;

[0059] (vi)N,N-bis(cis-4-isopropylcyclohexyl)-5-(cis-4-tert-pentylcyclohexylcarbonylamino)-isophthalamide;

[0060] (vii)N,N-bis(cis-4-n-butylcyclohexyl)-5-(cis-4-n-butylcyclohexylcarbonylamino)-isophthalamide;

[0061] (viii) N,N-bis(cis-4-n-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)-isophthalamide;

[0062] (ix)N,N-Di(cis-4-sec-butylcyclohexyl)-5-(cis-4-sec-butylcyclohexylcarbonylamino)-isophthalamide;

[0063] (x)N,N-bis(cis-4-sec-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)-isophthalamide;

[0064] (xi)N,N-Di(cis-4-tert-butylcyclohexyl)-5-(cis-4-n-propylcyclohexylcarbonylamino)-isophthalamide;

[0065] (xii)N,N-bis(cis-4-tert-butylcyclohexyl)-5-(cis-4-isopropylcyclohexylcarbonylamino)-isophthalamide;

[0066] (xiii)N,N-bis(cis-4-tert-butylcyclohexyl)-5-(cis-4-n-butylcyclohexylcarbonylamino)-isophthalamide;

[0067] (xiv)N,N-bis(cis-4-tert-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)-isophthalamide;

[0068] (xv)N,N-Di(cis-4-tert-butylcyclohexyl)-5-(cis-4-n-pentylcyclohexylcarbonylamino)-isophthalamide;

[0069] (xvi)N,N-Di(cis-4-tert-pentylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)-isophthalamide;

[0070] (xvii)N,N-bis(cis-4-tert-pentylcyclohexyl)-5-(cis-4-tert-pentylcyclohexylcarbonylamino)-isophthalamide; and

[0071] (xviii) Mixtures of them (i.e., mixtures of two or more of the aforementioned compounds).

[0072] In another preferred embodiment, the compound is selected from:

[0073] (i)N,N-bis(cis-4-isopropylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)-isophthalamide;

[0074] (ii) N,N-bis(cis-4-isopropylcyclohexyl)-5-(cis-4-tert-pentylcyclohexylcarbonylamino)-isophthalamide;

[0075] (iii) N,N-bis(cis-4-n-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)-isophthalamide;

[0076] (iv) N,N-bis(cis-4-sec-butylcyclohexyl)-5-(cis-4-sec-butylcyclohexylcarbonylamino)-isophthalamide;

[0077] (v)N,N-bis(cis-4-sec-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)-isophthalamide;

[0078] (vi)N,N-bis(cis-4-tert-butylcyclohexyl)-5-(cis-4-n-propylcyclohexylcarbonylamino)-isophthalamide;

[0079] (vii)N,N-bis(cis-4-tert-butylcyclohexyl)-5-(cis-4-isopropylcyclohexylcarbonylamino)-isophthalamide;

[0080] (viii) N,N-bis(cis-4-tert-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)-isophthalamide;

[0081] (ix)N,N-Di(cis-4-tert-pentylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)-isophthalamide;

[0082] (x)N,N-bis(cis-4-tert-pentylcyclohexyl)-5-(cis-4-tert-pentylcyclohexylcarbonylamino)-isophthalamide; and

[0083] (xi) Mixtures of them (i.e., mixtures of two or more of the aforementioned compounds).

[0084] In one preferred embodiment, the compound of formula (I) is N,N-bis(cis-4-tert-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)-isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-bis(cis-4-tert-butylcyclohexyl)-5-(cis-4-isopropylcyclohexylcarbonylamino)-isophthalamide. In yet another preferred embodiment, the compound of formula (I) is N,N-bis(cis-4-tert-butylcyclohexyl)-5-(cis-4-n-butylcyclohexylcarbonylamino)-isophthalamide. In yet another preferred embodiment, the compound of formula (I) is N,N-bis(cis-4-tert-pentylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)-isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-bis(cis-4-tert-butylcyclohexyl)-5-(cis-4-n-propylcyclohexylcarbonylamino)-isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-bis(cis-4-isopropylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)-isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-bis(cis-4-tert-pentylcyclohexyl)-5-(cis-4-tert-pentylcyclohexylcarbonylamino)-isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-bis(cis-4-isopropylcyclohexyl)-5-(cis-4-n-butylcyclohexylcarbonylamino)-isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-bis(cis-4-isopropylcyclohexyl)-5-(cis-4-n-pentylcyclohexylcarbonylamino)-isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-bis(cis-4-tert-butylcyclohexyl)-5-(cis-4-n-pentylcyclohexylcarbonylamino)-isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-bis(cis-4-isopropylcyclohexyl)-5-(cis-4-tert-pentylcyclohexylcarbonylamino)-isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-bis(cis-4-isopropylcyclohexyl)-5-(cis-4-n-propylcyclohexylcarbonylamino)-isophthalamide. In another preferred embodiment, the compound of formula (I) is N,N-bis(cis-4-n-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)-isophthalamide. In yet another preferred embodiment, the compound of formula (I) is N,N-bis(cis-4-n-butylcyclohexyl)-5-(cis-4-n-butylcyclohexylcarbonylamino)-isophthalamide.In another preferred embodiment, the compound of formula (I) is N,N-bis(cis-4-sec-butylcyclohexyl)-5-(cis-4-sec-butylcyclohexylcarbonylamino)-isophthalamide. In yet another preferred embodiment, the compound of formula (I) is N,N-bis(cis-4-sec-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)-isophthalamide.

[0085] This application also includes compositions containing one or more compounds of formula (I), such as compositions containing a mixture of two or more compounds of formula (I). (In this case, the cis isomer and the trans isomer are considered different compounds, such that 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 60% or more of R in all compounds of formula (I) present in the composition 1 R 2 and R 3 The group is located in cis with respect to the non-hydrogen substituent at the 1-position attached to the corresponding cyclohexane diene moiety. More preferably, about 65% or more of the R group in all compounds of formula (I) present in the composition is present in the composition. 1 R 2 and R 3 The group is located in cis with respect to the non-hydrogen substituent at the 1-position attached to the corresponding cyclohexane diene moiety. In another preferred embodiment, about 70% or more of the R group in all compounds of formula (I) present in the composition is present in the composition. 1 R 2 and R 3 The group is located in cis with respect to the non-hydrogen substituent at the 1-position attached to the corresponding cyclohexane diene moiety. In another preferred embodiment, about 75% or more of the R group in all compounds of formula (I) present in the composition is present in the composition. 1 R 2 and R 3 The group is located in cis with respect to the non-hydrogen substituent at the 1-position attached to the corresponding cyclohexane diene moiety. In another preferred embodiment, about 80% or more of the R group in all compounds of formula (I) present in the composition is present in the composition. 1 R 2 and R 3 The group is located in cis with respect to the non-hydrogen substituent at the 1-position attached to the corresponding cyclohexane diene moiety. In another preferred embodiment, about 85% or more of the R group in all compounds of formula (I) present in the composition is present. 1 R 2 and R 3The group is located in cis with respect to the non-hydrogen substituent at the 1-position attached to the corresponding cyclohexane diene moiety. In another preferred embodiment, about 90% or more of the R group in all compounds of formula (I) present in the composition is present in the composition. 1 R 2 and R 3 The group is located in cis with respect to the non-hydrogen substituent at the 1-position attached to the corresponding cyclohexane diene moiety. In another preferred embodiment, about 95% or more (e.g., about 96% or more, about 97% or more, about 98% or more, or about 99% or more) of the R group in all compounds of formula (I) present in the composition 1 R 2 and R 3 The group is located in the cis position relative to the non-hydrogen substituent at the 1-position attached to the corresponding cyclohexane dimethyl moiety.

[0086] In another preferred embodiment of the composition comprising 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 have R-positions respectively located in the cis position relative to the non-hydrogen substituents at the 1-position linked to the respective cyclohexanediyl moiety. 1 R 2 and R 3 More preferably, about 65 mol% or more of the compound of formula (I) present in the composition has R groups, each located in the cis position relative to the non-hydrogen substituent at the 1-position attached to the respective cyclohexane diel moiety. 1 R 2 and R 3 Group. In another preferred embodiment, about 70 mol% or more of the compound of formula (I) present in the composition has R groups, each located in a cis position relative to a non-hydrogen substituent at the 1-position connected to the respective cyclohexanediyl moiety. 1 R 2 and R 3 Group. In another preferred embodiment, about 75 mol% or more of the compound of formula (I) present in the composition has an R group, each located in the cis position relative to a non-hydrogen substituent at the 1-position connected to the respective cyclohexanediyl moiety. 1 R 2 and R 3 Group. In another preferred embodiment, about 80 mol% or more of the compound of formula (I) present in the composition has R groups, each located in the cis position relative to the non-hydrogen substituent at the 1-position attached to the respective cyclohexanediyl moiety. 1 R 2 and R 3In another preferred embodiment, about 85 mol% or more of the compound of formula (I) present in the composition has an R group, each located in the cis position relative to a non-hydrogen substituent at the 1-position connected to the respective cyclohexanediyl moiety. 1 R 2 and R 3 Group. In another preferred embodiment, about 90 mol% or more of the compound of formula (I) present in the composition has R groups, each located in the cis position relative to the non-hydrogen substituent at the 1-position connected to the respective cyclohexanediyl moiety. 1 R 2 and R 3 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 have each R group located in the cis position relative to the non-hydrogen substituent at the 1-position connected to the respective cyclohexanediyl moiety. 1 R 2 and R 3 Group.

[0087] Compounds of formula (I) can be prepared by any suitable method or synthetic approach. For example, the compound can be prepared by first reacting the desired 4-alkylcyclohexylamine with 5-nitroisophthaloyl dichloro to prepare an intermediate compound of formula (A).

[0088] (A)

[0089]

[0090] The intermediate compound of formula (A) can then be hydrogenated using known methods to prepare the corresponding amine compound of formula (B).

[0091] (B)

[0092]

[0093] The amine compound of formula (B) can then be reacted with the desired 4-alkylcyclohexane carbonyl chloride to prepare the desired compound of formula (I).

[0094] Where R 1 and R 2 Different compounds of formula (I) can be prepared, for example, by reacting a monoalkyl ester of 5-nitroisophthalate (e.g., monomethyl 5-nitroisophthalate) with oxaloyl chloride to prepare an acyl chloride compound of formula (J).

[0095] (J)

[0096]

[0097] Where R 11 The alkyl group is alkyl, such as methyl. The acyl chloride compound of formula (J) can then be reacted with the desired 4-alkylcyclohexylamine to prepare the intermediate compound (K) of formula (K).

[0098]

[0099] The intermediate compound of formula (K) can then be saponified with a suitable base (e.g., lithium hydroxide) to produce the corresponding carboxylate (e.g., a lithium salt of a carboxylic acid) and an alcohol (i.e., having the structure R). 11 Alcohols with OH, for example, in R 11 (Methanol when it is methyl). The corresponding carboxylate can then be hydrolyzed with a suitable acid (e.g., hydrochloric acid) to produce an acid of the following formula (L).

[0100] (L)

[0101]

[0102] The acid of formula (L) can then be reacted with oxalyl chloride to produce the corresponding acyl chloride compound of formula (M).

[0103] (M)

[0104]

[0105] The acyl chloride of formula (M) can then be reacted with the desired 4-alkylcyclohexylamine to prepare the intermediate compound of formula (N).

[0106] (N)

[0107]

[0108] The intermediate compound of formula (N) can then be reduced by known methods (e.g., hydrogenation) to prepare the corresponding diamine compound of formula (O).

[0109] (O)

[0110]

[0111] Finally, the intermediate compound of formula (O) can be reacted with the desired 4-alkylcyclohexane carbonyl chloride to produce the desired compound of formula (I).

[0112] 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) can be any of the embodiments discussed above in relation to the first embodiment of the present invention (e.g., a specific compound or a composition comprising a mixture of compounds).

[0113] The polymer composition may comprise any suitable polymer. Preferably, the polymer is a thermoplastic polymer (e.g., polyolefin, polyester, polyamide, polylactic acid, polycarbonate, acrylic polymer) or a mixture thereof. More preferably, the polymer is a polyolefin polymer, such as a polypropylene polymer, a polyethylene polymer, a polymethylpentene polymer (e.g., poly(4-methyl-1-pentene)), a polybutene polymer, a poly(vinylcyclohexane) polymer, and mixtures thereof. In a preferred embodiment, the polymer is a polypropylene polymer. More preferably, the polymer is selected from polypropylene homopolymers (e.g., random polypropylene homopolymers, isotactic polypropylene homopolymers, and syndiotactic polypropylene homopolymers), polypropylene copolymers (e.g., random polypropylene copolymers), polypropylene impact copolymers, and mixtures thereof. Suitable polypropylene copolymers include, but are not limited to, random copolymers prepared by polymerization of propylene in the presence of comonomers selected from ethylene, but-1-ene (i.e., 1-butene), and hex-1-ene (i.e., 1-hexene). In the polypropylene random copolymer, the comonomer may be present in any suitable amount, but is typically present in an amount of less than about 10% by weight (e.g., from about 1 to about 7% by weight). Suitable polypropylene impact copolymers include, but are not limited to, those prepared by adding copolymers selected from ethylene-propylene rubber (EPR), ethylene-propylene-diene monomer (EPDM), polyethylene, and plastomers to polypropylene homopolymers or polypropylene random copolymers. In the polypropylene impact copolymer, the copolymer may be present in any suitable amount, but is typically present in an amount of from about 5% to about 25% by weight. In a preferred embodiment, the polymer composition comprises a polyolefin polymer selected from polypropylene homopolymers, polypropylene random copolymers, and mixtures thereof. More preferably, the polymer composition comprises a polypropylene random polymer.

[0114] The polymer composition of the present invention may contain any suitable amount of one or more compounds of formula (I) above. In a preferred embodiment, the polymer composition contains at least 0.001 wt% of a compound of formula (I) relative to the total weight of the composition. In another preferred embodiment, the polymer composition contains at least 0.002 wt%, at least 0.003 wt%, at least 0.004 wt%, at least 0.005 wt%, at least 0.01 wt%, at least 0.02 wt%, at least 0.03 wt%, at least 0.04 wt%, at least 0.05 wt%, at least 0.1 wt%, at least 0.3 wt%, at least 0.5 wt%, at least 1 wt%, at least 5 wt%, or at least 10 wt% of a compound of formula (I) relative to the total weight of the composition. In another embodiment, the polymer composition preferably contains less than 99 wt% of a compound of formula (I) relative to the total weight of the composition. In another preferred embodiment, the polymer composition comprises 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 a compound of formula (I) relative to the total weight of the composition. In a series of particularly preferred embodiments, the polymer composition comprises, relative to the total weight of the composition, 0.001 wt% to 0.5 wt% (e.g., 0.01 wt% to 0.5 wt% or 0.05 wt% to 0.5 wt%), 0.001 wt% to 0.2 wt% (e.g., 0.01 wt% to 0.2 wt% or 0.05 wt% to 0.2 wt%), 0.001 wt% to 0.1 wt% (e.g., 0.01 wt% to 0.1 wt% or 0.05 wt% to 0.1 wt%), or 0.001 wt% to 0.07 wt% (e.g., 0.01 wt% to 0.07 wt%) of a compound of formula (I). As described above, the polymer composition of the present invention may comprise more than one compound of formula (I). In those embodiments in which the polymer composition comprises more than one triamide compound of formula (I), each triamide compound may be present in an amount falling within one of the above ranges, or the combined amount of all the triamide compounds may fall within one of the above ranges.

[0115] In addition to comprising one or more compounds of formula (I), the polymer compositions described herein may also contain other polymer additives. Suitable additional polymer additives include, but are not limited to: antioxidants (e.g., phenolic antioxidants, phosphite antioxidants, and combinations thereof), antiblocking agents (e.g., amorphous silica and diatomaceous earth), pigments (e.g., organic and inorganic pigments) and other colorants (e.g., dyes and polymer colorants), fillers and reinforcing agents (e.g., glass, glass fiber, talc, calcium carbonate, and magnesium oxysulfate whiskers), nucleating agents, clarifying agents, deacidifying agents (e.g., metal salts of fatty acids, such as 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 obtained by the reaction of fatty acids with ammonia or amine-containing compounds), fatty acid ester compounds (e.g., fatty acid ester compounds obtained by the reaction of fatty acids with hydroxyl-containing compounds—e.g., glycerol, diglycerol, and combinations thereof), and combinations of the foregoing.

[0116] The polymer compositions described herein can be prepared by any suitable method. For example, a polyolefin composition can be prepared by a simple mixture (e.g., high-shear or high-strength mixing) of a polyolefin polymer, one or more compounds of formula (I), and any other optional components. Alternatively, an additive composition comprising one or more compounds of formula (I) and any other optional components (e.g., those described above) can be premixed to provide a premixed composition. This premixed composition can then be mixed with a polymer to prepare the polymer compositions described above. The polymer compositions can be provided in any manner suitable for further processing to prepare articles. For example, the polymer compositions can be provided in the form of powders (e.g., free-flowing powders), flakes, granules, pellets, tablets, agglomerates, etc.

[0117] The polymer compositions described herein are considered suitable for the preparation of thermoplastic articles. The polymer compositions can be shaped into desired thermoplastic articles using 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 blow molding (blown film), film casting (cast film), etc.

[0118] The polymer compositions described herein can be used to produce any suitable articles or products. Suitable products include, but are not limited to, medical devices (e.g., pre-filled syringes for distillation applications, intravenous supply containers, and blood collection devices), food packaging, liquid containers (e.g., containers for beverages, pharmaceuticals, personal care compositions, shampoos, etc.), garment boxes, microwaveable articles, shelves, cabinet doors, machine parts, automotive parts, sheets, pipes, tubes, rotationally molded parts, blow-molded parts, films, fibers, etc.

[0119] The polymer compositions of the present invention have been observed to exhibit a highly desirable combination of low haze and low leaching of the triamide compounds of formula (I). Polymer compositions containing compounds of formula (I) (e.g., random copolymer compositions of polypropylene) typically exhibit haze levels at least 15% lower than those exhibited by polymer compositions containing structurally similar triamide compounds not covered by formula (I). Furthermore, polymer compositions containing certain compounds of formula (I) have been observed to exhibit single-digit haze levels comparable to those exhibited by more transparent polymers (e.g., polystyrene and acrylic polymers). As mentioned above, these polymer compositions also exhibit excellent (i.e., low) leaching of compounds of formula (I) from the polymer composition. In fact, polymer compositions containing certain compounds of formula (I) have been observed to exhibit leaching levels one to two orders of magnitude lower than those exhibited by polymer compositions containing structurally similar triamide compounds not covered by formula (I). It is believed that these properties exhibited by the polymer compositions of the present invention make them particularly well suited for the manufacture of thermoplastic articles or products requiring low haze levels and low leaching, such as articles and products intended for food contact and medical applications.

[0120] The following examples further illustrate the above-described subject matter, but should not be construed as limiting its scope in any way.

[0121] Example 1

[0122] This embodiment illustrates the synthesis of the triamide compound of the present invention (i.e., the triamide compound of formula (I)).

[0123] Under an inert atmosphere, 16.00 g (64.51 mmol) of 5-nitroisophthaloyl dichloro was added to 400 mL of dried tetrahydrofuran (THF). 12 mL of anhydrous pyridine was also added, and the solution was cooled to 25 °C using a water bath. Then, 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. THF was then removed by rotary evaporation, and 300 mL of methanol was added to the crude product. The methanol / product slurry was added to 2.5 L of stirred deionized (DI) water. The resulting mixture was stirred for 15 minutes, and the solid was collected by vacuum filtration. After rinsing the collected solid with 200 mL of DI water, the solid was slurried with DI water (2 x 1500 mL x 20 min) and collected by filtration. The crude product was then slurried in methanol (3 x 700 mL x 60 min) and collected by vacuum filtration. The separated solids were then dried in a vacuum oven at 85 °C for 23 h. 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.

[0124] 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 palladium / carbon (10 wt%). A 2 L Parr reactor was shut off and purged four times with nitrogen and five times with hydrogen under stirring. Hydrogenation was carried out at 40 °C and 90 psig hydrogen pressure for 24 h. The reaction mixture was transferred to a flask under an inert atmosphere and filtered through Whatman binder-free glass microfiber filter paper (2.7 μm) to remove the catalyst from the reaction materials. The THF / MeOH solvent mixture was removed by rotary evaporation, and the solids were slurried with diethyl ether (200 mL) for 1 h and collected by vacuum filtration. Additional solids were collected from the diethyl ether filtrate. The combined solids were dried in a vacuum oven at 65 °C for 8 h. Hydrogenation yields 12.27 g (96.8%) of 5-amino-N,N-bis(cis-4-(tert-butyl)cyclohexyl)isophthalamide.

[0125] Under an inert atmosphere, 6.08 g (13.34 mmol) of the previously obtained 5-amino-N,N-bis(cis-4-(tert-butyl)cyclohexyl)isophthalamide was added to 600 mL of anhydrous tetrahydrofuran (THF). 1.3 mL of anhydrous pyridine was added, and the solution was cooled to 15 °C with the aid of an ice-water bath. Then, 2.98 g (14.7 mmol) of cis-4-tert-butylcyclohexane carboxylic acid 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, after which 150 mL of acetone was added to the reaction slurry and stirred for 15 min. The reaction slurry was then added to a beaker containing 3000 mL of DI water with stirring. After the slurry was completely added, the system was stirred for 10 min, and the product was collected by vacuum filtration. The solid was washed with 200 mL of DI water and then re-slurried in 1600 mL of 80 / 20 DI water / MeOH solution for 15 minutes. The solid was then collected by vacuum filtration. The crude product was re-slurried in 300 mL of isopropanol for 1 hour and collected by vacuum filtration. The product solid was dried in a vacuum oven at 95 °C for 17 hours. This reaction yielded 7.54 g (90.8%) of N,N-bis(cis-4-tert-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide.

[0126] Example 2

[0127] This embodiment illustrates the synthesis of the triamide compound of the present invention (i.e., the triamide compound of formula (I)).

[0128] Under an inert atmosphere, 13.50 g (54.45 mmol) of 5-nitroisophthaloyl dichloro was added to 500 mL of dried THF. 10.2 mL of anhydrous pyridine was also added, and the solution was cooled to 25 °C using a water bath. Then, 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. THF was then removed by rotary evaporation, and 300 mL of IPA was added to the crude product. The IPA / product slurry was added to 2.8 L of stirred DI water. The resulting mixture was stirred for 20 minutes, and the solid was collected by vacuum filtration. After washing the collected solid with 1000 mL of DI water, the solid was slurried in 250 mL of 5 °C IPA for 60 minutes and collected by filtration. The crude product was then washed with 100 mL of -78 °C diethyl ether. The separated solid was then dried in a vacuum oven at 85°C for 23 hours. The reaction produced 22.57 g (85.4%) of fine white powder, which was N,N-bis(cis-4-(sec-butyl)cyclohexyl)-5-nitroisophthalamide.

[0129] The 22.57 g (46.47 mmol) N,N-bis(cis-4-(sec-butyl)cyclohexyl)-5-nitroisophthalamide obtained above was hydrogenated in a THF / MeOH mixture (1000 mL / 300 mL) with 1.60 g palladium / carbon (10 wt%). A 2 L Parr reactor was shut off and purged four times with nitrogen and five times with hydrogen under stirring. Hydrogenation was carried out at 40 °C and 90 psig hydrogen pressure for 24 hours. The reaction mixture was transferred to a flask under an inert atmosphere and filtered through Whatman binder-free glass microfiber filter paper (2.7 μm) to remove the catalyst from the reaction material. The THF / MeOH solvent mixture was removed by rotary evaporation, and the solids were slurried with IPA (200 mL) for 45 min and filtered. The collected solids were then washed with 75 mL of -78 °C diethyl ether. Additional solids were collected from the ether filtrate. The combined solids were dried in a vacuum oven at 45°C for 18 hours. The reaction produced 19.45 g (91.8%) of 5-amino-N,N-bis(cis-4-(sec-butyl)cyclohexyl)isophthalamide.

[0130] Under an inert atmosphere, 9.64 g (21.16 mmol) of the previously obtained 5-amino-N,N-bis(cis-4-(sec-butyl)cyclohexyl)isophthalamide was added to 900 mL of anhydrous tetrahydrofuran (THF). 2.1 mL of anhydrous pyridine was added, and the solution was cooled to 15 °C with the aid of an ice-water bath. Then, 4.72 g (23.28 mmol) of cis-4-tert-butylcyclohexane carboxylic acid 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, after which 150 mL of acetone was added to the reaction slurry and stirred for 15 min. The reaction slurry was then added to a beaker containing 2500 mL of DI water with stirring. After the slurry was completely added, the system was stirred for 10 min, and the product was collected by vacuum filtration. The solid was washed with 200 mL of DI water and then re-slurried in 1200 mL of a 75 / 25 DI water / IPA solution for 90 minutes. The solid was then collected by vacuum filtration. The crude product was re-slurried in 300 mL of IPA at 5 °C for 30 minutes and collected by vacuum filtration. The product solid was dried in a vacuum oven at 110 °C for 17 hours. The reaction yielded 12.65 g (96.1%) of N,N-bis(cis-4-sec-butylcyclohexyl)-5-(cis-4-tert-butylcyclohexylcarbonylamino)isophthalamide.

[0131] Example 3

[0132] This embodiment illustrates the preparation of a polymer composition according to the present invention and the properties of such a polymer composition.

[0133] Twenty triamide compounds were first synthesized according to the general procedure described above, and their effects were demonstrated in Examples 1 and 2. The triamide compounds are listed in Table 1 below. For ease of comparison, the triamide compounds all have similar cis content.

[0134] Table 1. Compound IDs and compound names of triamide compounds used in the preparation of polymer compositions.

[0135]

[0136]

[0137] The polymer compositions were prepared by compounding each triamide compound into a 12 MFR polypropylene random copolymer (SA849 RCP from LyondellBasell). The triamide compounds (i.e., compounds 1 through 20) were each added gravimetrically to the polymer granules (0.80 g powdered additive per 1000 g additive / polymer mixture to obtain 800 ppm triamide compound) and then mixed in a Henschel high-intensity mixer. The resulting mixture was melt-blended at 260 °C on a Deltaplast single-screw compounding extruder with a screw diameter of 25 mm and an aspect ratio of 30:1. The extrudates of each sample (in filament form) were cooled in a water bath and subsequently granulated. The melt-blended polymer composition was then injection molded using a 40-ton ARBURG ALLROUNDER 221K injection molding machine at a flatprofile barrel temperature of 260°C 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 dimensions of the plaque were verified using a micrometer.

[0138] Then, the percentage of haze was measured using the BYK-Gardner Haze-Guard Plus plate (including a control plate made without the use of triamide compounds) according to ASTM standard D1103-92.

[0139] The plates were also tested to determine the amount of triamide compound leached using a set of specified conditions. Specifically, leaching was performed for 2 hours at 100°C using a 550 mL stainless steel container with a stainless steel cap lined with PTFE. Glass septa were used to ensure separation of the polymer samples during migration testing. A 25% ethanol solution was used for leaching. Ethanol was of absolute grade. Water was deionized using an ion-exchange purification system to obtain deionized water. Repeated migration tests in the solvent were performed using two plates immersed in 250 mL of solvent. A control plate free of triamide compound was also prepared and leached using the conditions described above. After each heating time, aliquots (~1 mL) were removed from the leaching solvent and added to vials for LC analysis.

[0140] A 1000 ppm solution of each triamide compound was prepared by dissolving 0.100 g of the triamide compound in NMP, and a dilution was prepared in 100% ethanol. Calibration curves for each triamide compound were obtained using these solutions. A WaterACQUITY UPLC was used as the LC instrument, equipped with a Phenomenex Kinetex (2.6 μm particle size) as the analytical column and PDA and MS as detectors. The column temperature was 40 °C. The mobile phase used was methanol and water. The flow rate was set to 0.4 mL / min. The injection volume was 1 to 5 μL. The mass spectrometer was used with an SQD2 detector in single-ion recording (SIR) mode. The wavelength in the PDA detector was set to 200 to 800 nm. Each triamide compound was identified by comparing its retention time with the corresponding peak in the standard solution and its MS and UV spectra. Quantification was performed using the calibration curve with an external standard. The limit of detection (LOD) was determined by extrapolation to a signal-to-noise ratio of 3:1.

[0141] The results of the haze and leaching measurements are listed in Table 2 below. In the leaching amount column, the symbol "ND" means "not detected," indicating that the amount of leached triamide compound (if any) cannot be quantified because the measurement did not return a signal exceeding the above-mentioned limit of detection (LOD).

[0142] Table 2. Leaching and haze measurements of polymer compositions prepared with compounds 1 to 20 and control polymer compositions.

[0143] Compound ID Leaching amount (ppb) Haze (%) No (control) -- 39.3 Compound 1 458 15.1 Compound 2 2 6.1 Compound 3 ND 14.5 Compound 4 4 3.9 Compound 5 5 4.0 Compound 6 5 7.5 Compound 7 ND 3.6 Compound 8 14 4.1 Compound 9 15 16.8 Compound 10 20 3.8 Compound 11 22 15.3 Compound 12 35 11.6 Compound 13 ND 4.5 Compound 14 49 5.5 Compound 15 55 10.2 Compound 16 ND 4.5 Compound 17 91 11.6 Compound 18 276 9.8 Compound 19 303 17.4 Compound 20 477 25.5

[0144] As can be seen from the data in Table 2, using R... 1 R 2 and R 3 Polymer compositions prepared from triamide compounds of formula (I) each being alkyl (i.e., polymer compositions prepared with compounds 2 to 18) and those containing at least R 1 R 2 and R3 Compared to compositions made from non-alkyl triamide compounds (i.e., polymer compositions made from compounds 1, 19, and 20), these exhibit an ideal combination of low haze and leaching. When the R of the triamide compound... 1 R 2 and R 3 The difference in leaching levels is even more pronounced when the group is an alkyl group having two or more carbon atoms (e.g., C3 alkyl or longer). Furthermore, when R... 1 R 2 and R 3 When at least one of the components is a branched alkyl group, the haze and leaching levels are consistently low; where the required performance is typically even higher as the number of branched alkyl groups increases.

[0145] In view of the above, the inventors of the present invention believe that the triamide compounds of the present invention stand out due to their highly desirable combination of low haze and low leaching. It is believed that polymer compositions made with such triamide compounds will be suitable for a wide range of applications requiring polymer compositions to exhibit low haze and leaching levels (e.g., food contact and medical device applications).

[0146] All references cited in this article (including publications, patent applications and patents) are incorporated herein by reference, as if each reference had been explicitly cited for all its public content.

[0147] Unless otherwise stated herein or where the context clearly contradicts it, the use of the terms “a,” “an,” “the,” “the,” and similar designations in describing the subject matter of this application (particularly in the case of the appended claims) shall be construed as encompassing both singular and plural forms. Unless otherwise stated, the terms “comprising,” “having,” “including,” and “containing” shall be construed as open-ended terms (i.e., meaning “including but not limited to”). Unless otherwise stated herein, the ranges of values ​​described herein are intended only as a way of abbreviating each individual value falling within that range, and each individual value is incorporated into this specification as if it were recited individually herein. Unless otherwise stated herein or where the context clearly contradicts it, all methods described herein may be implemented in any suitable order. Unless otherwise claimed, the use of any and all instances or exemplary wording given herein (e.g., “for example” or “as”) is intended only to better elucidate the subject matter of this application and does not limit the scope of the subject matter. The wording in the specification shall not be construed as indicating that any non-claim elements are necessary for practicing the subject matter described herein.

[0148] Preferred embodiments of the subject matter of this application are described herein, including the best methods known to the inventors for implementing the claimed subject matter. Variations of those preferred embodiments will be apparent to those skilled in the art upon reading the above description. The inventors anticipate that those skilled in the art will use such variations as appropriate, and the inventors desire that the subject matter described herein be practiced in ways different from those specifically described herein. Therefore, this disclosure includes all modifications and equivalents to the subject matter described in the appended claims permitted by applicable law. Furthermore, unless otherwise stated herein or otherwise clearly contradicted in the context, this disclosure covers any combination of the foregoing elements in all possible variations.

Claims

1. Compound of formula (I) (I) ， Where R 1 R 2 and R 3 Independently selected from linear or branched C1-C5 alkyl groups, and R 1 R 2 and R 3 At least one of the groups is arranged in cis with respect to the non-hydrogen substituent at the 1-position attached to the corresponding cyclohexane diene moiety.

2. The compound of claim 1, wherein R 1 R 2 and R 3 At least two of the groups are arranged in cis with respect to the non-hydrogen substituent at the 1-position of the corresponding cyclohexane diene moiety.

3. The compound of claim 2, wherein R 1 R 2 and R 3 Each of the groups is arranged in cis with respect to the non-hydrogen substituent at the 1-position attached to the corresponding cyclohexane diene moiety.

4. The compound of claim 1, wherein R 1 R 2 and R 3 At least one of them is a branched alkyl group.

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

6. The compound of claim 4, wherein R 1 R 2 and R 3 At least two of them are branched alkyl groups.

7. The compound of claim 6, wherein R 1 R 2 and R 3 Each of them is a branched alkyl group.

8. The compound of claim 3, wherein the compound is selected from: N,N -two( Cis -4-Isopropylcyclohexyl)-5-( Cis -4-n-propylcyclohexylcarbonylamino)isophthalamide; N,N -two( Cis -4-Isopropylcyclohexyl)-5-( Cis -4-Isopropylcyclohexylcarbonylamino)isophthalamide; N,N -two( Cis -4-Isopropylcyclohexyl)-5-( Cis -4-n-Butylcyclohexylcarbonylamino)isophthalamide; N,N -two( Cis -4-Isopropylcyclohexyl)-5-( Cis -4-tert-butylcyclohexylcarbonylamino)isophthalamide; N,N -two( Cis -4-Isopropylcyclohexyl)-5-( Cis -4-n-pentylcyclohexylcarbonylamino)isophthalamide; N,N -two( Cis -4-Isopropylcyclohexyl)-5-( Cis -4-tert-pentylcyclohexylcarbonylamino)isophthalamide; N,N -two( Cis -4-n-Butylcyclohexyl)-5-( Cis -4-n-Butylcyclohexylcarbonylamino)isophthalamide; N,N -two( Cis -4-n-Butylcyclohexyl)-5-( Cis -4-tert-butylcyclohexylcarbonylamino)isophthalamide; N,N -two( Cis -4-sec-butylcyclohexyl)-5-( Cis -4-sec-butylcyclohexylcarbonylamino)isophthalamide; N,N -two( Cis -4-sec-butylcyclohexyl)-5-( Cis -4-tert-butylcyclohexylcarbonylamino)isophthalamide; N,N -two( Cis -4-tert-butylcyclohexyl)-5-( Cis -4-n-propylcyclohexylcarbonylamino)isophthalamide; N,N -two( Cis -4-tert-butylcyclohexyl)-5-( Cis -4-Isopropylcyclohexylcarbonylamino)isophthalamide; N,N -two( Cis -4-tert-butylcyclohexyl)-5-( Cis -4-n-Butylcyclohexylcarbonylamino)isophthalamide; N,N -two( Cis -4-tert-butylcyclohexyl)-5-( Cis -4-tert-butylcyclohexylcarbonylamino)isophthalamide; N,N -two( Cis -4-tert-butylcyclohexyl)-5-( Cis -4-n-pentylcyclohexylcarbonylamino)isophthalamide; N,N -two( Cis -4-tert-pentylcyclohexyl)-5-( Cis -4-tert-butylcyclohexylcarbonylamino)isophthalamide; N,N -two( Cis -4-tert-pentylcyclohexyl)-5-( Cis -4-tert-pentylcyclohexylcarbonylamino)isophthalamide; and their mixtures.

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

10. The compound of claim 8, wherein the compound is N,N -two( Cis -4-tert-butylcyclohexyl)-5-( Cis -4-Isopropylcyclohexylcarbonylamino)isophthalamide.

11. The compound of claim 8, wherein the compound is N,N -two( Cis -4-tert-butylcyclohexyl)-5-( Cis -4-n-Butylcyclohexylcarbonylamino)isophthalamide.

12. The compound of claim 8, wherein the compound is N,N -two( Cis -4-tert-pentylcyclohexyl)-5-( Cis -4-tert-butylcyclohexylcarbonylamino)isophthalamide.

13. The compound of claim 8, wherein the compound is N,N -two( Cis -4-tert-butylcyclohexyl)-5-( Cis -4-n-propylcyclohexylcarbonylamino)isophthalamide.

14. The compound of claim 8, wherein the compound is N,N -two( Cis -4-Isopropylcyclohexyl)-5-( Cis -4-tert-butylcyclohexylcarbonylamino)isophthalamide.

15. The compound of claim 8, wherein the compound is N,N -two( Cis -4-tert-pentylcyclohexyl)-5-( Cis -4-tert-pentylcyclohexylcarbonylamino)isophthalamide.

16. The compound of claim 8, wherein the compound is N,N -two( Cis -4-Isopropylcyclohexyl)-5-( Cis -4-n-Butylcyclohexylcarbonylamino)isophthalamide.

17. The compound of claim 8, wherein the compound is N,N -two( Cis -4-Isopropylcyclohexyl)-5-( Cis -4-n-pentylcyclohexylcarbonylamino)isophthalamide.

18. The compound of claim 8, wherein the compound is N,N -two( Cis -4-tert-butylcyclohexyl)-5-( Cis -4-n-pentylcyclohexylcarbonylamino)isophthalamide.

19. The compound of claim 8, wherein the compound is N,N -two( Cis -4-Isopropylcyclohexyl)-5-( Cis -4-tert-pentylcyclohexylcarbonylamino)isophthalamide.

20. The compound of claim 8, wherein the compound is N,N -two( Cis -4-Isopropylcyclohexyl)-5-( Cis -4-n-propylcyclohexylcarbonylamino)isophthalamide.

21. The compound of claim 8, wherein the compound is N,N -two( Cis -4-n-Butylcyclohexyl)-5-( Cis -4-tert-butylcyclohexylcarbonylamino)isophthalamide.

22. The compound of claim 8, wherein the compound is N,N -two( Cis -4-n-Butylcyclohexyl)-5-( Cis -4-n-Butylcyclohexylcarbonylamino)isophthalamide.

23. The compound of claim 8, wherein the compound is N,N -two( Cis -4-sec-butylcyclohexyl)-5-( Cis -4-sec-butylcyclohexylcarbonylamino)isophthalamide.

24. The compound of claim 8, wherein the compound is N,N -two( Cis -4-sec-butylcyclohexyl)-5-( Cis -4-tert-butylcyclohexylcarbonylamino)isophthalamide.

25. The compound of claim 8, wherein the compound is N,N -two( Cis -4-Isopropylcyclohexyl)-5-( Cis -4-Isopropylcyclohexylcarbonylamino)isophthalamide.

26. A composition comprising two or more compounds of formula (I): (I) ， Among them, each R 1 R 2 and R 3 Independently selected from linear or branched C1-C5 alkyl groups, and comprising 60% or more of R in all compounds of formula (I) present in the composition. 1 R 2 and R 3 The group is located in the cis position relative to the non-hydrogen substituent at the 1-position attached to the corresponding cyclohexane dimethyl moiety.

27. The composition of claim 26, wherein R in each of the formulas (I) 1 R 2 and R 3 At least one of them is a branched alkyl group.

28. The composition of claim 27, wherein R in each of the formulas (I) 3 It is a branched alkyl group.

29. The composition of claim 27, wherein R in each of the formulas (I) 1 R 2 and R 3 At least two of them are branched alkyl groups.

30. The composition of claim 29, wherein R in each of the formulas (I) 1 R 2 and R 3 It is a branched alkyl group.

31. The composition of claim 26, wherein 75% or more of R in all compounds of formula (I) present in the composition 1 R 2 and R 3 The group is located in the cis position relative to the non-hydrogen substituent at the 1-position attached to the corresponding cyclohexane dimethyl moiety.

32. The composition of claim 31, wherein 95% or more of R in all compounds of formula (I) present in the composition 1 R 2 and R 3 The group is located in the cis position relative to the non-hydrogen substituent at the 1-position attached to the corresponding cyclohexane dimethyl moiety.

33. A polymer composition comprising: (a) a compound of any one of claims 1 to 25 or a composition of any one of claims 26 to 32; and (b) Polyolefin polymers.

34. The polymer composition of claim 33, wherein the polyolefin polymer is a polypropylene polymer.

35. The polymer composition of claim 34, wherein the polyolefin polymer is selected from polypropylene homopolymers, polypropylene random copolymers, and mixtures thereof.

36. The polymer composition of claim 35, wherein the polyolefin polymer is a random copolymer of polypropylene.

37. The polymer composition of claim 33, wherein, Based on the total weight of the polymer composition, the total amount of the compound of formula (I) present in the polymer composition is 0.001% by weight or higher.

38. The polymer composition of claim 37, wherein, Based on the total weight of the polymer composition, the total amount of the compound of formula (I) present in the polymer composition is from 0.001% by weight to 0.5% by weight.

39. The polymer composition of claim 38, wherein, Based on the total weight of the polymer composition, the total amount of the compound of formula (I) present in the polymer composition is from 0.01% by weight to 0.2% by weight.

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