RU2797296C1 - Trisamide compounds and compositions containing them - Google Patents

Abstract

FIELD: organic chemistry.

SUBSTANCE: invention relates to a trisamide compound of formula (I), which, as a polymer additive, reduces the level of turbidity of the polymer and has minimal extraction from the polymer mass. In this formula, R¹, R² and R³ are independently selected from the group consisting of C₁-C₅ alkyl groups.

EFFECT: invention also relates to a polymer composition for the manufacture of molded articles containing a trisamide compound of formula (I).

19 cl, 3 tbl, 6 ex

Description

Cross reference to related patent applications

[0001] Pursuant to paragraph 119(e) of Title 35, United States Code, this application claims priority and benefit of concurrently pending U.S. Patent Application No. 62/947,474, filed December 12, 2019, the contents of which are incorporated in their entirety in this document by reference.

TECHNICAL FIELD OF THE INVENTION

[0002] This application relates to trisamide compounds (in particular, trisamide derivatives, formally derived from 3,5-diaminobenzoic acid) and compositions containing them.

BACKGROUND OF THE INVENTION

[0003] Polymer resins are widely used in a variety of fields because they have, among other things, excellent processing properties, mechanical properties (in particular, in relation to a unit of mass) and electrical properties. Although the polymers themselves may have advantageous properties, additives may be used to further improve these properties and/or overcome disadvantages.

[0004] Polyolefins are a group of polymer resins that exhibit particular versatility. Polyolefins are semi-crystalline polymers. The polyolefin that is allowed to cool relatively slowly (for example, as cooling occurs during the manufacture of molded plastic articles) contains amorphous regions in which the polymer chains are randomly arranged and crystalline regions in which the polymer chains assume an ordered configuration. Within these crystalline regions of the polyolefin polymer chains are combined into domains, which are commonly referred to by the term "crystalline plates". Under normal process conditions, the lamellae grow radially in all directions as the polyolefin polymer cools from the molten state. As a result of this radial growth, spherulites are formed, which are spherical semi-crystalline regions composed of numerous crystalline plates and interrupted by amorphous regions. The size of spherulites is influenced by several parameters and can range from hundreds of nanometers to several millimeters in diameter. When the spherulites have a size that greatly exceeds the wavelength of visible light, the spherulites scatter the visible light passing through the polymer. This scattering of visible light results in a cloudy appearance, commonly referred to as "polymer haze" or simply "haze". While significant levels of polymer haze may be acceptable in some applications, there are certain products (eg, storage containers) for which relatively clear plastic materials are required by consumers, which should therefore exhibit low levels of haze.

[0005] Over time, several approaches have been developed to reduce the haze of polyolefins. One approach that has achieved significant commercial success involves the use of clarifying agents. Brighteners are additives (often organic compounds) that, when the polymer is processed by melting, form crystallization centers in the cooling polymer and reduce the size of spherulites or even virtually prevent the formation of these particles, which effectively scatter light. For example, bis(3,4-dimethylbenzylidene)sorbitol has enjoyed significant commercial success due to its ability to reduce haze in polypropylene polymers. However, bis(3,4-dimethylbenzylidene)sorbitol is not free from limitations. In particular, this clarifying agent cannot reduce the haze of polypropylene polymers to less than the haze levels of clearer polymers such as polystyrene and acrylic resins. The residual haze of polymers clarified with bis(3,4-dimethylbenzylidene)sorbitol limits their use and end uses.

[0006] In an attempt to overcome the limitation of sorbitan acetals (eg, bis(3,4-dimethylbenzylidene)sorbitol), other clarifying agents have been developed. For example, trisamide compounds (e.g., trisamide derivatives formally derived from 1,3,5-benzenetriamine, 3,5-diaminobenzoic acid, 5-aminoisophthalic acid, or trimesic acid) are initially promising because, at relatively low levels, such compounds can reduce haze. polypropylene polymers to levels that can be achieved using bis(3,4-dimethylbenzylidene)sorbitol. Despite their original promise, the disclosed trisamide compounds still cannot provide haze levels to compete with clearer polymers. In addition, many of the described trisamide compounds can be extracted from the polypropylene in which they are added. These undesirable extraction levels make such trisamide compounds less suitable for food contact and medical device applications (i.e., applications in which the polymer clarified with the trisamide compound comes into contact with food [e.g., during storage or food packaging] or used in medical devices [eg, syringes]) where industry preference and/or legal regulations require additives that exhibit minimal extraction from the polymer.

[0007] Thus, there is still a need for clarifying agents that can both provide desirable low levels of haze to polyolefin polymers and exhibit minimal extraction from the polyolefin polymers to which they are added. In addition, there is still a need for polymeric compositions containing such clarifying agents that exhibit, in the desired combination, low haze levels and minimal extraction of clarifying agent. The goal of the various embodiments that are described herein is to provide such clarifying agents and compositions.

The essence of the present invention

[0008] According to a first embodiment of the present invention, a compound of formula (I) is provided.

moreover, the groups R ¹ , R ² and R ³ are independently selected from the group consisting of alkyl groups.

[0009] According to a second embodiment of the present invention, there is provided a polymer composition comprising a compound of formula (I) and a polyolefin polymer.

Detailed description of the present invention

[0010] According to a first embodiment of the present invention, there is provided a compound of formula (I) below, which is a trisamide derivative formally derived from 3,5-diaminobenzoic acid. The structure of formula (I) is presented as follows.

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

[0011] The groups R ¹ , R ² and R ³ may be any suitable alkyl group. According to a preferred embodiment, R ¹ , R ² and R ³ are independently selected from the group consisting of C ₁ -C ₂₀ -alkyl groups (for example, C ₃ -C ₂₀ -alkyl groups), preferably C ₁ -C ₁₂ -alkyl groups ( eg C ₃ -C ₁₂ alkyl groups), more preferably C ₁ -C ₈ alkyl groups (eg C ₃ -C ₈ alkyl groups), and most preferably C ₁ -C ₅ alkyl groups (eg C ₂ -C ₅ -alkyl groups or C ₃ -C ₅ -alkyl groups). Suitable alkyl groups may be linear or branched. According to a preferred embodiment, at least one of R ¹ , R ² and R ³ is a branched alkyl group. If only one of R ¹ , R ² and R ³ is a branched alkyl group, R ³ is preferably a branched alkyl group. According to a further embodiment, when only one of R ¹ , R ² and R ³ is a branched alkyl group, R ¹ is preferably a branched alkyl group. According to a further preferred embodiment, at least two of the groups R ¹ , R ² and R ³ are independently selected branched alkyl groups.

In one such embodiment, R ¹ and R ² are preferably independently selected branched alkyl groups. According to another such embodiment, R ² and R ³ are preferably independently selected branched alkyl groups. According to a further preferred embodiment, a branched alkyl group is independently selected as each of R ¹ , R ² and R ³ . According to such embodiments containing branched alkyl groups, the alkyl group may contain any suitable number of carbon atoms, with preferred examples being C ₃ -C ₂₀ branched alkyl groups, C ₃ -C ₁₂ branched alkyl groups, C ₃ -C ₈ branched -alkyl groups; and branched C ₃ -C ₅ -alkyl groups. Suitable branched alkyl groups preferably contain a branching point corresponding to a carbon atom occupying the alpha position or the beta position with respect to the cyclohexanediyl moiety.

[0012] According to a preferred embodiment, R ¹ , R ² and R ³ are independently selected from the group consisting of n-propyl, isopropyl, n-butyl, sec-butyl (i.e., butan-2-yl or 1-methylpropyl ), isobutyl (i.e. 2-methylpropyl), t-butyl (i.e. 1,1-dimethylethyl), n-pentyl, t-pentyl (i.e. 2-methylbutan-2-yl or 1, 1-dimethylpropyl), neopentyl (i.e. 2,2-dimethylpropyl), isopentyl (i.e. 3-methylbutyl), sec-pentyl (i.e. pentan-2-yl or 1-methylbutyl), sec- isopentyl (i.e. 3-methylbutan-2-yl or 1,2-dimethylpropyl), pentan-3-yl (i.e. 1-ethylpropyl), and 2-methylbutyl. In a more preferred embodiment, R ¹ , R ² and R ³ are independently selected from the group consisting of n-propyl, isopropyl, n-butyl, sec-butyl (i.e. butan-2-yl or 1-methylpropyl), isobutyl (i.e. 2-methylpropyl), t-butyl (i.e. 1,1-dimethylethyl), t-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). According to a further preferred embodiment, R ¹ , R ² and R ³ are independently selected from the group consisting of n-propyl, isopropyl, n-butyl, isobutyl (i.e. 2-methylpropyl), tert-butyl (i.e. 1 ,1-dimethylethyl), and tert-pentyl (i.e. 2-methylbutan-2-yl or 1,1-dimethylpropyl).

[0013] As noted above, at least one of the groups R ¹ , R ² and R ³ preferably represents a branched alkyl group. Thus, according to a preferred embodiment, at least one of the groups R ¹ , R ² and R ³ is selected from the group consisting of isopropyl, sec-butyl (i.e. butan-2-yl or 1-methylpropyl), isobutyl ( i.e. 2-methylpropyl), t-butyl (i.e. 1,1-dimethylethyl), t-pentyl (i.e. 2-methylbutan-2-yl or 1,1-dimethylpropyl), neopentyl (t i.e. 2,2-dimethyl propyl), isopentyl (i.e. 3-methyl butyl), sec-pentyl (i.e. pentan-2-yl or 1-methylbutyl), sec-isopentyl (i.e. 3-methylbutan-2-yl or 1,2-dimethylpropyl), pentan-3-yl (i.e. 1-ethylpropyl) and 2-methylbutyl. According to a further preferred embodiment, at least one of the groups R ¹ , R ² and R ³ is selected from the group consisting of isopropyl, sec-butyl (i.e. butan-2-yl or 1-methylpropyl), isobutyl (i.e. e. 2-methylpropyl), t-butyl (i.e. 1,1-dimethylethyl), t-pentyl (i.e. 2-methylbutan-2-yl or 1,1-dimethylpropyl), sec-pentyl (t 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, at least one of the groups R ¹ , R ² and R ³ 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). According to a further preferred embodiment, at least one of the groups R ¹ , R ² and R ³ is selected from the group consisting of t-butyl (i.e. 1,1-dimethylethyl) and t-pentyl (i.e. 2- methylbutan-2-yl or 1,1-dimethylpropyl). According to a further preferred embodiment, both R ² and R ³ are branched alkyl groups independently selected from the groups listed in this paragraph. According to a further preferred embodiment, each of R ² and R ³ is a branched alkyl group independently selected from one of the groups listed in this paragraph. Finally, according to the following preferred embodiment, each of the groups R ¹ , R ² and R ³ represents a branched alkyl group, which is independently selected from one of the groups listed in this paragraph.

[0014] According to a preferred embodiment, the compound is selected from the group consisting of

(i) N-(4-isopropylcyclohexyl)-3,5-bis-[4-isopropylcyclohexylcarbonylamino]-benzamide;

(ii) N-(4-isopropylcyclohexyl)-3,5-bis-[4-tert-butylcyclohexylcarbonylamino]-benzamide;

(iii) N-(4-n-propylcyclohexyl)-3,5-bis-[4-tert-butylcyclohexylcarbonylamino]-benzamide;

(iv) N-(4-n-butylcyclohexyl)-3,5-bis-[4-tert-butylcyclohexylcarbonylamino]-benzamide;

(v) N-(4-tert-butylcyclohexyl)-3,5-bis-[4-isopropylcyclohexylcarbonylamino]benzamide;

(vi) N-(4-tert-butylcyclohexyl)-3,5-bis-[4-tert-butylcyclohexylcarbonylamino]-benzamide;

(vii) N-(4-tert-pentylcyclohexyl)-3,5-bis-[4-tert-butylcyclohexylcarbonylamino]benzamide;

(viii) N-(4-tert-butylcyclohexyl)-3,5-bis-[4-tert-pentylcyclohexylcarbonylamino]benzamide; And

(ix) N-(4-tert-pentylcyclohexyl)-3,5-bis-[4-tert-pentylcyclohexylcarbonyl amino]benzamide; And

(x) mixtures thereof (ie mixtures of two or more of any of the compounds listed above).

According to a further preferred embodiment, the compound is selected from the group consisting of

(i) N-(4-isopropylcyclohexyl)-3,5-bis-[4-tert-butylcyclohexylcarbonylamino]-benzamide;

(ii) N-(4-n-propylcyclohexyl)-3,5-bis-[4-tert-butylcyclohexylcarbonylamino]-benzamide;

(iii) N-(4-n-butylcyclohexyl)-3,5-bis-[4-tert-butylcyclohexylcarbonylamino]-benzamide;

(iv) N-(4-tert-butylcyclohexyl)-3,5-bis-[4-tert-butylcyclohexylcarbonylamino]benzamide;

(v) N-(4-tert-pentylcyclohexyl)-3,5-bis-[4-tert-butylcyclohexylcarbonylamino]benzamide;

(vi) N-(4-tert-butylcyclohexyl)-3,5-bis-[4-tert-pentylcyclohexylcarbonylamino]benzamide;

(vii) N-(4-tert-pentylcyclohexyl)-3,5-bis-[4-tert-pentylcyclohexylcarbonylamino]benzamide; And

(viii) mixtures thereof (ie mixtures of two or more of any of the compounds listed above).

According to one preferred embodiment, the compound of formula (I) is N-(4-isopropylcyclohexyl)-3,5-bis-[4-isopropylcyclohexylcarbonylamino]-benzamide. According to a further preferred embodiment, the compound of formula (I) is N-(4-isopropylcyclohexyl)-3,5-bis-[4-t-butylcyclohexylcarbonylamino]-benzamide. According to a further preferred embodiment, the compound of formula (I) is N-(4-n-propylcyclohexyl)-3,5-bis-[4-t-butylcyclohexylcarbonylamino]-benzamide. According to a further preferred embodiment, the compound of formula (I) is N-(4-n-butylcyclohexyl)-3,5-bis-[4-tert-butylcyclohexylcarbonylamino]-benzamide. According to a further preferred embodiment, the compound of formula (I) is N-(4-tert-butylcyclohexyl)-3,5-bis-[4-isopropylcyclohexylcarbonylamino]-benzamide. According to a further preferred embodiment, the compound of formula (I) is N-(4-tert-butylcyclohexyl)-3,5-bis-[4-tert-butylcyclohexylcarbonylamino]-benzamide. According to a further preferred embodiment, the compound of formula (I) is N-(4-tert-pentylcyclohexyl)-3,5-bis-[4-tert-butylcyclohexylcarbonylamino]-benzamide. According to a further preferred embodiment, the compound of formula (I) is N-(4-tert-butylcyclohexyl)-3,5-bis-[4-tert-pentylcyclohexylcarbonylamino]-benzamide. According to a further preferred embodiment, the compound of formula (I) is N-(4-tert-pentylcyclohexyl)-3,5-bis-[4-tert-pentylcyclohexylcarbonylamino]-benzamide.

[0015] As can be seen, in formula (I), each cyclohexanediyl moiety is substituted and contains non-hydrogen substituents (i.e., an R ¹ , R ² or R ³ group and an amide substituent-containing benzene moiety) in each from 1- and 4-positions. The non-hydrogen substituents that are attached to each cyclohexanediyl moiety can be arranged in two different spatial configurations with respect to each other. Both non-hydrogen substituents may be on the same side of the center plane of the cyclohexane ring, and this corresponds to the cis configuration, or both substituents, which are not hydrogen atoms, may be on opposite sides of the center plane of the cyclohexane ring, and this corresponds to the trans configuration. Each of the R ¹ , R ² and R ³ groups may be in the cis-position or trans-position with respect to the substituent, which is not a hydrogen atom and attached in the 1-position to the corresponding cyclohexanediyl fragment. According to a preferred embodiment, at least one of the groups R ¹ , R ² and R ³ is cis to a non-hydrogen substituent attached in the 1-position to the corresponding cyclohexanediyl moiety. According to a further preferred embodiment, at least two of the groups R ¹ , R ² and R ³ are in cis with respect to a non-hydrogen substituent attached in the 1-position to the corresponding cyclohexanediyl moiety. According to a further preferred embodiment, each of R ¹ , R ² and R ³ is cis to a non-hydrogen substituent attached at the 1-position to the corresponding cyclohexanediyl moiety.

[0016] According to a preferred embodiment, the compound is selected from the group consisting of

(i) N-(cis-4-isopropylcyclohexyl)-3,5-bis-[cis-4-isopropylcyclohexylcarbonylamino]-benzamide;

(ii) N-(cis-4-isopropylcyclohexyl)-3,5-bis-[cis-4-t-butylcyclohexylcarbonylamino]-benzamide;

(iii) N-(cis-4-n-propylcyclohexyl)-3,5-bis-[cis-4-tert-butylcyclohexylcarbonylamino]-benzamide;

(iv) N-(cis-4-n-butylcyclohexyl)-3,5-bis-[cis-4-t-butylcyclohexylcarbonylamino]-benzamide;

(v) N-(cis-4-tert-butylcyclohexyl)-3,5-bis-[cis-4-isopropylcyclohexylcarbonylamino]-benzamide;

(vi) N-(cis-4-tert-butylcyclohexyl)-3,5-bis-[cis-4-tert-butylcyclohexylcarbonylamino]-benzamide;

(vii) N-(cis-4-tert-pentylcyclohexyl)-3,5-bis-[cis-4-tert-butylcyclohexylcarbonylamino]benzamide;

(viii) N-(cis-4-tert-butylcyclohexyl)-3,5-bis-[cis-4-tert-pentylcyclohexylcarbonylamino]-benzamide; And

(ix) N-(cis-4-tert-pentylcyclohexyl)-3,5-bis-[cis-4-tert-pentylcyclohexylcarbonylamino]-benzamide; And

(x) mixtures thereof (ie mixtures of two or more of any of the compounds listed above).

According to a further preferred embodiment, the compound is selected from the group consisting of

(i) N-(cis-4-isopropylcyclohexyl)-3,5-bis-[cis-4-t-butylcyclohexylcarbonylamino]-benzamide;

(ii) N-(cis-4-n-propylcyclohexyl)-3,5-bis-[cis-4-tert-butylcyclohexylcarbonylamino]benzamide;

(iii) N-(cis-4-n-butylcyclohexyl)-3,5-bis-[cis-4-t-butylcyclohexylcarbonylamino]-benzamide;

(iv) N-(cis-4-tert-butylcyclohexyl)-3,5-bis-[cis-4-tert-butylcyclohexylcarbonylamino]-benzamide;

(v) N-(cis-4-tert-pentylcyclohexyl)-3,5-bis-[cis-4-tert-butylcyclohexylcarbonylamino]-benzamide;

(vi) N-(cis-4-tert-butylcyclohexyl)-3,5-bis-[cis-4-tert-pentylcyclohexylcarbonyl amino]-benzamide;

(vii) N-(cis-4-tert-pentylcyclohexyl)-3,5-bis-[cis-4-tert-pentylcyclohexylcarbonyl amino]-benzamide; And

(viii) mixtures thereof (ie mixtures of two or more of any of the compounds listed above).

According to one preferred embodiment, the compound of formula (I) is N-(cis-4-isopropylcyclohexyl)-3,5-bis-[cis-4-isopropylcyclohexylcarbonylamino]-benzamide. According to a further preferred embodiment, the compound of formula (I) is N-(cis-4-isopropylcyclohexyl)-3,5-bis-[cis-4-t-butylcyclohexylcarbonylamino]-benzamide. According to a further preferred embodiment, the compound of formula (I) is N-(cis-4-n-propylcyclohexyl)-3.,5-bis-[cis-4-tert-butylcyclohexylcarbonylamino]-benzamide. According to a further preferred embodiment, the compound of formula (I) is N-(cis-4-n-butylcyclohexyl)-3,5-bis-[cis-4-tert-butylcyclohexylcarbonylamino]-benzamide. According to a further preferred embodiment, the compound of formula (I) is N-(cis-4-tert-butylcyclohexyl)-3,5-bis-[cis-4-isopropylcyclohexylcarbonylamino]-benzamide. According to a further preferred embodiment, the compound of formula (I) is N-(cis-4-tert-butylcyclohexyl)-3,5-bis-[cis-4-tert-butylcyclohexylcarbonylamino]-benzamide. According to a further preferred embodiment, the compound of formula (I) is N-(cis-4-tert-pentylcyclohexyl)-3,5-bis-[cis-4-tert-butylcyclohexylcarbonylamino]-benzamide. According to a further preferred embodiment, the compound of formula (I) is N-(cis-4-tert-butylcyclohexyl)-3,5-bis-[cis-4-tert-pentylcyclohexylcarbonylamino]-benzamide. According to a further preferred embodiment, the compound of formula (I) is N-(cis-4-tert-pentylcyclohexyl)-3,5-bis-[cis-4-tert-pentylcyclohexylcarbonylamino]-benzamide.

[0017] The present application also extends to compositions containing one or more compounds of formula (I), such as a composition containing two or more compounds of formula (I) in admixture. (In this context, cis and trans isomers are considered to be different compounds, such that a mixture of two or more isomers is a composition containing two or more compounds of formula (I) in a mixture.) According to such embodiments, it is preferred that 60% or more of the groups R ¹ , R ² and R ³ in all compounds of formula (I) that are present in the composition are in the cis-position with respect to the substituent, which is not a hydrogen atom and is attached in the 1-position to the corresponding cyclohexanediyl fragment. More preferably, about 65% or more of the groups R ¹ , R ² and R ³ in all compounds of formula (I) that are present in the composition are in the cis-position with respect to the substituent, which is not a hydrogen atom and is attached in the 1-position to the corresponding cyclohexanediyl moiety. According to a further preferred embodiment, about 70% or more of the R ¹ , R ² and R ³ groups in all of the compounds of formula (I) that are present in the composition are cis to the non-hydrogen substituent attached to 1-position to the corresponding cyclohexanediyl moiety. According to a further preferred embodiment, about 75% or more of the R ¹ , R ² and R ³ groups in all compounds of formula (I) that are present in the composition are in cis with respect to the non-hydrogen substituent attached at 1-position to the corresponding cyclohexanediyl moiety. According to a further preferred embodiment, about 80% or more of the R ¹ , R ² and R ³ groups in all compounds of formula (I) that are present in the composition are in cis with respect to the non-hydrogen substituent attached at 1-position to the corresponding cyclohexanediyl moiety. According to a further preferred embodiment, about 85% or more of the R ¹ , R ² and R ³ groups in all compounds of formula (I) that are present in the composition are cis to the non-hydrogen substituent attached to the 1-position to the corresponding cyclohexanediyl moiety. According to a further preferred embodiment, about 90% or more of the R ¹ , R ² and R ³ groups in all compounds of formula (I) that are present in the composition are in cis with respect to the non-hydrogen substituent attached at 1-position to the corresponding cyclohexanediyl moiety. In a further 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 ¹ , R ² , and R ³ groups in all compounds formulas (I), which are present in the composition, are in the cis-position with respect to the substituent, which is not a hydrogen atom and is attached in the 1-position to the corresponding cyclohexanediyl fragment.

[0018] According to the following preferred embodiment of the composition containing in a mixture of two or more compounds of formula (I), about 60 mol. % or more of the compounds of formula (I) that are present in the composition contain groups R ¹ , R ² and R ³ , each of which is in the cis-position with respect to a substituent that is not a hydrogen atom and is attached in the 1-position to the corresponding cyclohexanediyl moiety. More preferably about 65 mol. % or more of the compounds of formula (I) that are present in the composition contain groups R ¹ , R ² and R ³ , each of which is in the cis-position with respect to a substituent that is not a hydrogen atom and is attached in the 1-position to the corresponding cyclohexanediyl moiety. According to the following preferred embodiment, about 70 mol. % or more of the compounds of formula (I) that are present in the composition contain groups R ¹ , R ² and R ³ , each of which is in the cis-position with respect to a substituent that is not a hydrogen atom and is attached in the 1-position to the corresponding cyclohexanediyl moiety. According to the following preferred embodiment, about 75 mol. % or more of the compounds of formula (I) that are present in the composition contain groups R ¹ , R ² and R ³ , each of which is in the cis-position with respect to a substituent that is not a hydrogen atom and is attached in the 1-position to the corresponding cyclohexanediyl moiety. According to the following preferred embodiment, about 80 mol. % or more of the compounds of formula (I) that are present in the composition contain groups R ¹ , R ² and R ³ , each of which is in the cis-position with respect to a substituent that is not a hydrogen atom and is attached in the 1-position to the corresponding cyclohexanediyl moiety. According to the following preferred embodiment, about 85 mol. % or more of the compounds of formula (I) that are present in the composition contain groups R ¹ , R ² and R ³ , each of which is in the cis-position with respect to a substituent that is not a hydrogen atom and is attached in the 1-position to the corresponding cyclohexanediyl moiety. According to the following preferred embodiment, about 90 mol. % or more of the compounds of formula (I) that are present in the composition contain groups R ¹ , R ² and R ³ , each of which is in the cis-position with respect to a substituent that is not a hydrogen atom and is attached in the 1-position to the corresponding cyclohexanediyl moiety. According to the following preferred embodiment, about 95 mol. % or more (for example, about 96 mol.% or more, about 97 mol.% or more, about 98 mol.% or more, or about 99 mol.% or more) of the compounds of formula (I), which are present in the composition, contain R ¹ , R ² and R ³ groups, each of which is in the cis-position with respect to the substituent, which is not a hydrogen atom and is attached in the 1-position to the corresponding cyclohexanediyl fragment.

[0019] The compounds of formula (I) can be obtained using any suitable method or synthetic process. For example, a compound can be prepared by first reacting the desired 4-alkylcyclohexylamine and 3,5-dinitrobenzoyl chloride (3,5-dinitrobenzoic acid chloride) to give the following intermediate of formula (A).

The intermediate compound of formula (A) can then be reduced using known methods (for example, by hydrogenation) to obtain the corresponding diamine compound of formula (B) below.

The compound of formula (B) may then be reacted with the desired 4-alkylcyclohexanecarbonyl chloride to give the desired compound of formula (I). In this final step, a mixture of two different 4-alkylcyclohexanecarbonyl chlorides can be reacted with a compound of formula (B) to give a compound of formula (I) in which the R ² and R ³ groups are different (or are in different spatial positions with respect to the substituent , which is not a hydrogen atom and attached in the 1-position to the corresponding cyclohexanediyl fragment). However, the reaction product obtained using a mixture of different 4-alkylcyclohexanecarbonyl chlorides may also contain significant amounts of compounds of formula (I) in which R ² and R ³ are the same. Thus, subsequent purification may be necessary to separate the desired asymmetric compound from said other components.

[0020] Alternatively, to obtain asymmetric compounds of formula (I) (for example, compounds in which the groups R ² and R ³ are different), 3-amino-5-nitrobenzoic acid and the desired 4-alkylcyclohexanecarbonyl chloride can be introduced into the reaction to obtain an intermediate compound of formula (J) below.

The intermediate compound of formula (J) can then be reacted with oxalyl chloride to give the corresponding acyl chloride of formula (K) below.

The acyl chloride of formula (K) can then be reacted with the desired 4-alkylcyclohexylamine to give an intermediate of formula (L) below.

The intermediate compound of formula (L) can then be hydrogenated using known methods to give the corresponding amine compound of formula (M) below.

Finally, the amine compound of formula (M) may be reacted with the desired 4-alkylcyclohexanecarbonyl chloride to give the desired compound of formula (I).

[0021] According to a second embodiment of the present invention, there is provided a polymer composition comprising a compound of formula (I) and a polymer. In such an embodiment, the compound of formula (I) may be a compound according to any of the embodiments (eg, a specific compound or a composition containing mixtures of compounds) discussed above in connection with the first embodiment of the present invention.

[0022] The polymer composition may contain any suitable polymer. Preferably, the polymer is a thermoplastic polymer such as a polyolefin, a polyester, a polyamide, a polylactic acid, a polycarbonate, an 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 (eg, poly(4-methyl-1-pentene)), a polybutylene polymer, a polyvinylcyclohexane polymer, and mixtures thereof. According to a preferred embodiment, the polymer is a polypropylene polymer. More preferably, the polymer is selected from the group consisting of polypropylene homopolymers (e.g., atactic polypropylene homopolymer, isotactic polypropylene homopolymer, and syndiotactic polypropylene homopolymer), polypropylene copolymers (e.g., polypropylene random copolymers), polypropylene impact copolymers, and mixtures thereof. Suitable polypropylene copolymers are, but are not limited to, random copolymers resulting from the polymerization of propylene in the presence of a comonomer selected from the group consisting of ethylene, but-1-ene (i.e. 1-butene), and hex-1- ene (i.e. 1-hexene). In such polypropylene random copolymers, the comonomer may be present in any suitable amount, but is typically present in an amount of less than about 10% by weight. % (for example, from about 1 to about 7 wt. %). Suitable polypropylene impact copolymers include, but are not limited to, copolymers resulting from the addition of a copolymer selected from the group consisting of ethylene propylene rubber (EPR), ethylene propylene diene monomer (EPDM), polyethylene and plastomers to a polypropylene homopolymer or polypropylene random copolymer. In such polypropylene impact copolymers, the copolymer may be present in any suitable amount, but is typically present in an amount of from about 5 to about 25 wt. %. In a preferred embodiment, the polymer composition comprises a polyolefin polymer selected from the group consisting of polypropylene homopolymers, polypropylene random copolymers, and mixtures thereof. More preferably, the polymeric composition comprises a polypropylene random copolymer.

[0023] The polymer composition according to the present invention may contain any suitable amount of one or more compounds of formula (I) as described above. According to a preferred embodiment, the polymer composition contains, relative to the total weight of the composition, at least 0.001 wt. % compound of formula (I). According to a further preferred embodiment, the polymer composition contains, relative to the total weight of the composition, 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. % compound of formula (I). According to the following embodiment, the polymer composition preferably contains, relative to the total weight of the composition, less than 99 wt. % compound of formula (I). According to the following preferred embodiment, the polymer composition contains, relative to the total weight of the composition, less than 95 wt. %, less than 80 wt. %, less than 50 wt. %, less than 25 wt. %, less than 10 wt. %, less than 5 wt. %, less than 2 wt. %, less than 1 wt. %, less than 0.5 wt. %, less than 0.2 wt. %, less than 0.1 wt. %, or less than 0.07 wt. % compound of formula (I). According to a number of particularly preferred embodiments, the polymer composition contains, relative to the total weight of the composition, from 0.001 wt. % up to 0.5 wt. % (for example, from 0.01 wt.% to 0.5 wt.% or from 0.05 wt.% to 0.5 wt.%), from 0.001 wt. % to 0.2 wt. % (for example, from 0.01 wt.% to 0.2 wt.% or from 0.05 wt.% to 0.2 wt.%), from 0.001 wt. % to 0.1 wt. % (for example, from 0.01 wt.% to 0.1 wt.% or from 0.05 wt.% to 0.1 wt.%), or from 0.001 wt. % to 0.07 wt. % (for example, from 0.01 wt.% to 0.07 wt.%) of the compounds of formula (I). As noted above, the polymer composition according to the present invention may contain more than one compound of formula (I). According to such embodiments, in which the polymer composition contains more than one trisamide compound of formula (I), each trisamide compound may be present in an amount within one of the ranges presented above, or the total amount of all trisamide compounds may be within one from the ranges above.

[0024] The polymer composition described herein may contain other polymer additives that complement one or more compounds of formula (I). Suitable additives for polymers include, but are not limited to, antioxidants (e.g., phenolic antioxidants, phosphite antioxidants, and combinations thereof), anti-caking agents (e.g., amorphous silica and diatomaceous earth), pigments (e.g., organic pigments and inorganic pigments) and other colorants (for example, dyes and polymeric colorants), fillers and reinforcing agents (for example, glass, glass fibers, talc, calcium carbonate and magnesium oxysulfate in the form of whiskers), nucleating agents, clarifying agents, acid neutralizers (for example, metal salts of fatty acids, such as metal salts of stearic acid), polymer processing aids (for example, processing aids for fluorinated polymers), polymer crosslinkers, anti-friction additives (for example, fatty acid amide compounds and the resulting reactions between a fatty acid and ammonia or a compound containing amino groups), fatty acid ester compounds (for example, fatty acid ester compounds resulting from the reaction between a fatty acid and a compound containing hydroxyl groups, such as glycerol, diglycerol and their combinations), as well as combinations of the above substances.

[0025] The polymer composition described herein can be made by any suitable method. For example, the polyolefin composition can be made by simple mixing (eg, high shear or high intensity mixing) of the polyolefin polymer, one or more compounds of formula (I), and any additional optional components. Alternatively, an additive composition containing one or more compounds of formula (I) and any additional optional components (such as those described above) may be premixed to form a premixed composition. This premixed composition and polymer can then be mixed to form a polymer composition as described above. The polymer composition can be made in any form suitable for use in downstream processes and product manufacture. For example, the polymer composition may be formulated into powder (eg, free flowing powder), flakes, grains, granules, tablets, agglomerates, and the like.

[0026] The polymer composition described herein is considered suitable for use in the manufacture of thermoplastic products. The polymer composition can be formed into a desired thermoplastic article 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, injection molding). film extrusion or foam extrusion), extrusion blow molding, thermoforming, roto molding, film blow molding into blown film, film injection molding into cast film, etc.

[0027] The polymer composition as described herein can be used to make any suitable article or product. Suitable articles include, but are not limited to, medical devices (e.g., pre-filled syringes for autoclave applications, IV containers, and blood collection devices), food packaging, liquid containers (e.g., containers for beverages, medicinal products, personal care compositions, shampoos, etc.), clothing packaging, microwaveable articles, shelves, cabinet doors, mechanical parts, automotive parts, sheets, pipes, tubes, rotationally molded articles made blow molding products, films, fibers, etc.

[0028] The polymer composition of the present invention has been observed to exhibit, in a highly desirable combination, low levels of turbidity and extraction of the trisamide compound of formula (I). Polymer compositions (e.g., polypropylene random copolymer compositions) containing a compound of formula (I) typically exhibit haze levels that are at least 15% lower than haze levels exhibited by polymer compositions containing structurally similar trisamide compounds. to which formula (I) does not apply. In addition, polymeric compositions containing certain compounds of formula (I) have been observed to exhibit single digit haze levels that compete with haze levels exhibited by clearer polymers such as polystyrene and acrylic polymers. As noted above, these polymer compositions also exhibit exceptionally good (ie low) extraction of the compound of formula (I) from the polymer composition. As such, polymer compositions containing certain compounds of formula (I) have been observed to exhibit extraction levels that are two orders of magnitude lower than the extraction levels exhibited by polymer compositions containing structurally similar trisamide compounds not covered by formula ( I). These properties exhibited by the polymer compositions of the present invention have been observed to make the polymer compositions particularly well suited for use in the manufacture of thermoplastic articles or products requiring low levels of turbidity and extraction, such as articles and products intended to come into contact with foodstuffs, and medical products.

[0029] The following examples further illustrate the above described object of the present invention, but, of course, they should not be construed as limiting the scope of the present invention in any way.

Example A

[0030] This example demonstrates the preparation of trisamide compounds of the present invention.

[0031] 6.5 g (41.8 mmol) of a 50/50 mixture of 4-cis-tert-butylcyclohexylamine and 4-trans-tert-butyl ring ore xylamine and dry LiCl at the tip of a spatula was added under an inert atmosphere at 200 ml of tetrahydrofuran (THF) (pure for analysis). 3.3 g (41.8 mmol) of dry pyridine was added and the solution was cooled to a temperature of 5°C. Then 8.8 g (38.1 mmol) of 3,5-dinitrobenzoic acid chloride was added in portions. The reaction mixture was stirred at 25° C. for 2 hours. After that, the solvent was removed and the solid residue was stirred with about 500 ml of water. After decantation of water, the solid residue was dissolved in 50 ml of MeOH and precipitated with water. The precipitate was filtered off and dried.

[0032] 11.7 g (33.5 mmol) of the precipitate obtained as described above was hydrogenated in a mixture of THF/MeOH (200 ml/50 ml) in the presence of 1.0 g Pd/C (10 wt.%) . The reactor was closed and purged 3 times with nitrogen and 3 times with hydrogen while stirring. The hydrogenation was carried out at a temperature of 35°C and a hydrogen pressure of 3 bar for 12 hours. The reaction mixture was transferred under an inert atmosphere to a flask and filtered through alumina (Alox N) to remove the catalyst and water.

[0033] 10.2 g (35.2 mmol) of the amine prepared as above and dry LiCl at the tip of a spatula were added under an inert atmosphere to 350 ml of tetrahydrofuran (THF) (assay grade). Added 5.5 g (70.0 mmol) of dry pyridine, and the solution was cooled to a temperature of 5°C. Then 14.2 g (70.3 mmol) of cis-4-tert-butylcyclohexylcarboxylic acid chloride was added. The reaction mixture was stirred at 25° C. for 2 hours. Thereafter, the solvent was removed and the solid residue was stirred in about 400 ml of water for 15 minutes. After filtering the solid product, it was added to 1 L of N,N-dimethylformamide (DMF) and refluxed for 5 minutes. After cooling to room temperature, the residue was filtered off and dried in a vacuum oven.

[0034] Subsequent analysis of the resulting product confirmed that it is N-(4-tert-butylcyclohexyl)-3,5-bis-[cis-4-tert-butylcyclohexylcarbonylamino]-benzamide. According to the 1H NMR spectrum, it was determined that approximately 90 mol. % product was N-(cis-4-tert-butylcyclohexyl)-3,5-bis-[cis-4-tert-butylcyclohexylcarbonylamino]-benzamide.

Example B

[0035] This example demonstrates the preparation of trisamide compounds of the present invention.

[0036] 4.3 g (28.0 mmol) of cis-4-tert-butylcyclohexylamine and dry LiCl at the tip of a spatula were added under an inert atmosphere in 250 ml of tetrahydrofuran (THF) (pure for analysis). 2.3 g (28.5 mmol) of dry pyridine and 2.7 g (25.0 mmol) of trimethylchlorosilane were added, and the solution was cooled to a temperature of 5°C. Then 5.8 g (25.1 mmol) of acid chloride 3 were added in portions ,5-dinitrobenzoic acid. The reaction mixture was stirred at 25° C. for 2 hours. After that, the reaction mixture was added to 2 l of ice water during vigorous stirring. After stirring for 2 hours, the precipitate was filtered off and dried in a vacuum oven at 40°C.

[0037] 8.3 g (24.0 mmol) of the precipitate obtained as described above was hydrogenated in a mixture of THF and EHN (250 ml/50 ml) in the presence of 0.24 g Pd/C (10 wt.%) . The reactor was closed and purged 3 times with nitrogen and 3 times with hydrogen while stirring. The hydrogenation was carried out at a temperature of 35°C and a hydrogen pressure of 5 bar for 12 hours. The reaction mixture was transferred under an inert atmosphere to a flask and filtered through alumina (Alox N) to remove the catalyst and water.

[0038] 6.4 g (22.1 mmol) of the amine prepared as described above and dry LiCl at the tip of a spatula were added under an inert atmosphere to 250 ml of tetrahydrofuran (THF) (assay grade). 4.2 g (53.3 mmol) of dry pyridine and 2.4 g (22.0 mmol) of trimethylchlorosilane were added and the solution was cooled to 5°C. 4-tert-butylcyclohexylcarboxylic acid and 1.1 g (5.6 mmol) trans-4-tert-butylcyclohexylcarboxylic acid chloride. The reaction mixture was stirred at 25° C. for 2 hours. After that, the reaction mixture was added to 2 l of ice water during vigorous stirring. After stirring for 2 hours, the precipitate was filtered off and dried in a vacuum oven at 40°C.

[0039] Subsequent analysis of the resulting product confirmed that it is N-(cis-4-tert-butylcyclohexyl)-3,5-bis-[4-tert-butylcyclohexylcarbonylamino]-benzamide. Approximately 90 mole % of the product was N-(cis-4-tert-butylcyclohexyl)-3,5-bis-[cis-4-tert-butylcyclohexylcarbonylamino]-benzamide by ¹ H NMR spectrum.

Example C

[0040] This example demonstrates the preparation of trisamide compounds of the present invention.

[0041] 4.3 g (28.0 mmol) of cis-4-tert-butylcyclohexylamine and dry LiCl at the tip of a spatula were added under an inert atmosphere in 250 ml of tetrahydrofuran (THF) (pure for analysis). 2.3 g (28.5 mmol) of dry pyridine and 2.7 g (25.0 mmol) of trimethylchlorosilane were added and the solution was cooled to 5°C. Then 5.8 g (25.1 mmol) of 3,5-dinitrobenzoic acid chloride were added in portions. The reaction mixture was stirred at 25° C. for 2 hours. After that, the reaction mixture was added to 2 l of ice water during vigorous stirring. After stirring for 2 hours, the precipitate was filtered off and dried in a vacuum oven at 40°C.

[0042] 8.3 g (24.0 mmol) of the precipitate obtained as described above was hydrogenated in a mixture of THF and EtOH (250 ml/50 ml) in the presence of 0.24 g Pd/C (10 wt.%) . The reactor was closed and purged 3 times with nitrogen and 3 times with hydrogen while stirring. The hydrogenation was carried out at a temperature of 35°C and a hydrogen pressure of 5 bar for 12 hours. The reaction mixture was transferred under an inert atmosphere to a flask and filtered through alumina (Alox N) to remove the catalyst and water.

[0043] 6.4 g (22.1 mmol) of the amine prepared as described above and dry LiCl at the tip of a spatula were added under inert atmosphere to 250 ml of tetrahydrofuran (THF) (assay grade). 4.2 g (53.3 mmol) of dry pyridine and 2.4 g (22.0 mmol) of trimethylchlorosilane were added and the solution was cooled to a temperature of 5°C. Then 9.4 g (46.7 mmol) of cis-4-tert-butylcyclohexylcarboxylic acid chloride was added. The reaction mixture was stirred at 25° C. for 2 hours. After that, the reaction mixture was added to 2 l of ice water during vigorous stirring. After stirring for 2 hours, the precipitate was filtered off and dried in a vacuum oven at 40°C.

[0044] The resulting product is N-(cis-4-tert-butylcyclohexyl)-3,5-bis-[cis-4-tert-butylcyclohexylcarbonylamino]-benzamide.

Example D

[0045] This example demonstrates the manufacture of polymer compositions according to the present invention and the properties of such polymer compositions.

[0046] Powdered propylene random copolymer (SA849 RCP from LyondellBasell) was vigorously mixed with a sufficient amount of the corresponding trisamide compound (sample A from example A and sample B from example B) to obtain a masterbatch containing 2 wt. % trisamide compound. The resulting master batch was mixed with a sufficient amount of pure polymer to obtain a polymer composition containing 0.08 wt. % trisamide compound.

[0047] Molding of the compositions was carried out using a laboratory extruder with two co-rotating screws over a period of about 5 minutes at a screw speed of 100 rpm and a temperature of about 240°C. About 5.0 g of the melt was directly transferred into a 12 ml DSM Xplore microinjector for resin injection molding (RTM) and injected into the polished mold at a pressure of about 6 bar and a temperature of about 240°C. The resulting samples had a diameter of 2.5 cm and a thickness of about 1.1 mm and were used for subsequent optical examination to determine the percent haze. The results of these turbidity measurements are shown in Table 1 below.

[0048] As can be seen from the data in Table 1, the polymer compositions containing the trisamide compound of the present invention (ie Samples A and B) exhibited significantly less haze than the control. These data demonstrate that the trisamide compounds of the present invention are effective brighteners for polymers (eg polypropylene).

Example E

[0049] This example demonstrates the synthesis of a trisamide compound of the present invention, which is a trisamide compound of formula (I).

[0050] N-(cis-4-tert-pentylcyclohexyl)-3,5-dinitrobenzamide was synthesized by adding 36.07 g of 3,5-dinitrobenzoyl chloride in 400 ml of anhydrous THF and 15 ml of pyridine. The reaction mixture was stirred for 5 minutes and cooled in a bath of divided water to a temperature of 20°C. Thereafter, cis-4-tert-pentylsusohexylamine (28.61 g) dissolved in 100 ml anhydrous THF was added dropwise over half an hour at such a rate as to raise the reaction temperature to 30°C. The reaction mixture was stirred overnight and then 300 ml MeOH was added. THF was removed to a large extent by rotary evaporation, and the remaining methanol solution was added dropwise during vigorous stirring in 3 l of deionized water. A fine yellow precipitate was isolated by filtration, suspended twice with water (1 L, 20 minutes), collected by filtration after each wash, and then suspended twice with diethyl ether (800 ml, 15 minutes). The collected solid was air dried and then dried in a vacuum oven at 60° C. for 17 hours to give a light yellow powder.

[0051] The steam reactor with a volume of 2000 ml model 4522M was purged with nitrogen and then loaded with 1.02 g of 10 wt. % palladium on carbon. Thereafter, 1 L of THF was added to the reactor. Then, 14.00 g of N-(cis-4-tert-pentylcyclohexyl)-3,5-dinitrobenzamide obtained as described above was dissolved in 600 ml of THF and loaded into the reactor. The reactor was closed and purged with nitrogen (4 times at 60 psi) and then heated to 40° C. while stirring at 1800 rpm. After equilibrating for 15 minutes, the reactor was purged with hydrogen (5 times at 70 psi), then pressurized to 100 psi with hydrogen, and the reactor was held at that temperature while stirring for 19 hours. . The reaction material was filtered to remove the catalyst and the solvent was removed by rotary evaporation to give a light red glassy material. The reaction yielded 3,5-diamino-N-(cis-4-tert-pentylcyclohexyl)benzamide.

[0052] 11.79 g (38.69 mmol) of 3,5-diamino-N-(cis-4-tert-pentylcyclohexyl)benzamide prepared as described above was added under an inert atmosphere to 800 ml of dry tetrahydrofuran (THF) . Added 7.5 ml of dry pyridine, and the reaction mixture was cooled to a temperature of 15°C using an ice water bath. Thereafter, 17.26 g (85.1 mmol) of cis-4-tert-butylcyclohexanecarboxylic acid chloride were added. The reaction mixture was stirred at 15°C for 30 minutes and at 21°C for 21 hours. Approximately 800 ml was removed by rotary evaporation, and then 500 ml of methanol was added to the reaction suspension, which was stirred for 15 minutes. The reaction suspension was then poured into a beaker containing 2500 ml of deionized water while stirring. After completion of the slurry addition, the system was stirred for 10 minutes and the product was collected by filtration under reduced pressure. The solid was then suspended in 2000 ml of a 75/25 mixture of deionized water and methanol for 1 hour, and the solid was then collected by filtration under reduced pressure. The crude product was resuspended in 300 ml diethyl ether for 30 minutes and collected by filtration under reduced pressure. The resulting solid was dried in a vacuum oven at 105° C. for 19 hours. The resulting product was N-(cis-4-tert-pentylcyclohexyl)-3,5-bis-[cis-4-tert-butylcyclohexylcarbonylamino]-benzamide.

Example F

[0053] This example demonstrates the manufacture of polymer compositions according to the present invention and the properties of such polymer compositions.

[0054] Seventeen trisamide compounds were first synthesized according to the general procedure described above and demonstrated in Examples A-C and E. The trisamide compounds are listed below in Table 2. For ease of comparison of various compounds, all trisamide compounds had a similar content of cis isomers.

[0055] Polymer compositions were made by adding each trisamide compound to a 12 MFR polypropylene random copolymer (SA849 RCP from LyondellBasell). The trisamide compounds, which are compounds 1-17, were added gravimetrically to the polymer pellets in each case (0.80 g of additive powder per 1000 g of additive-polymer mixture was added to obtain a trisamide compound content of 800 ppm), and then mixed using a high intensity Henschel mixer. The resulting mixture was melted and passed through a Deltaplast single screw extrusion mixer having a screw diameter of 25 mm and a L/D ratio of 30:1 at a temperature of 240°C. The extrudate (in the form of a filament) for each sample was cooled in a water bath and then granulated. The melt-blown resin composition was then injection molded using a 40 ton ARBURG ALLROUNDER 221K injection molding machine to produce wafers having dimensions of approximately 51 mm x 76 mm and a thickness of 0.76 mm at a flat drum temperature of 240° C. and back pressure. 100 bar. The dimensions of the plates were checked with a micrometer after incubation for 24 hours.

[0056] Percent haze of the plates (including a control plate made without the addition of a trisamide compound) was then measured according to ASTM D1103-92 using a Haze-Guard Plus instrument from BYK-Gardner.

[0057] In addition, the plates were examined to determine the extracted amount of the trisamide compound using a specific set of conditions. Specifically, extraction was carried out at 100° C. for 2 hours using 550 ml stainless steel tanks having a Teflon coating and stainless steel lids. Glass spacers were used to ensure separation of the polymer samples during the migration study. A solution of 25% ethanol was used for extraction. Absolute ethanol and deionized water obtained using an ion exchange purification system were used. A duplicate solvent migration study was performed using two plates immersed in 250 ml of solvent. In addition, control plates without the trisamide compound were made and subjected to extraction using the conditions described above. Aliquots (~1 ml) were taken from the extraction solvents after each heating period into a tube for analysis by liquid chromatography.

[0058] A solution containing 1000 ppm of the trisamide compound was prepared in each case by dissolving 0.100 g of the compound in N-methyl-pyrrolidone (NMP) and dilutions were made using 100% ethanol. The resulting solutions were used to construct a calibration curve for each trisamide compound. The liquid chromatograph used ACQUITY UPLC water and a 2.6 µm Phenomenex Kinetex analytical column, a photodiode array detector (PDA) and a mass spectrometric detector. The column temperature was 40°C. Methanol and water were used as the mobile phase. The flow rate was set at 0.4 ml/min. The volume of the injected sample was 1-5 μl. The mass spectrometer was used in Selected Ion Detection (SIR) mode using an SQD2 detector. The wavelength of the PDA detector was 200-800 nm. Each trisamide compound was identified by comparing its retention time with the corresponding peaks for the standard solution, as well as its mass spectrum and ultraviolet spectrum. Quantitative determination was carried out using the calibration curve of the external standard. The limit of detection (LOD) was determined by extrapolation to a signal to noise ratio of 3:1.

[0059] The results of the turbidity and extraction measurements are shown in Table 3 below. In the "extracted amount" column, the entry "not detected" means that the extracted amount of the trisamide compound (if present) could not be determined because the measurement did not result in received a signal that exceeded the limit of detection (LOD) as specified above.

[0060] As can be seen from the data in Table 2, polymer compositions made with the addition of trisamide compounds of formula (I), in which all R ¹ , R ² and R ³ groups are alkyl groups (i.e., polymer compositions made with the addition of compounds 2-10, 12-14 and 16-17) showed a desirable combination of low levels of turbidity and extraction compared to compositions made with the addition of trisamide compounds in which at least one of the groups R ¹ , R ² and R ³ is not an alkyl group (i.e. polymer compositions made with the addition of compounds 1, 11 and 15). The difference in extraction levels is even more pronounced when the groups R ¹ , R ² and R ³ in trisamide compounds are alkyl groups containing three or more carbon atoms. In addition, differences in haze and extraction levels are greater when the trisamide compound contains a branched alkyl group, in particular when at least R ² and R ³ are branched alkyl groups.

[0061] With regard to extraction, trisamide compounds according to the present invention, as a rule, show a lower extraction than the same trisamide compound in which R ¹ , R ² and R ³ represent hydrogen atoms. As a rule, extraction levels decrease as the number of carbon atoms in the alkyl groups increases. The presence of branched alkyl groups, particularly when at least R ² and R ³ are branched alkyl groups, also reduces extraction levels.

[0062] In view of the above, the present inventors believe that the trisamide compounds of the present invention are exceptional due to their highly advantageous combination of low levels of turbidity and extraction. The authors believe that polymer compositions made using such trisamide compounds will be suitable for a wide variety of applications that require polymer compositions that exhibit low levels of turbidity and extraction (for example, in articles that come into contact with food and in medical devices ).

[0063] All documents, including publications, patent applications, and patents, that are cited herein are hereby incorporated by reference to the same extent as if each document cited were individually and specifically indicated as being incorporated by reference and has been reproduced in its entirety in this document.

[0064] The use of grammatical forms of the singular in the context of the description of the subject matter of the present application (in particular, in the context of the following claims) should be construed as denoting the singular and plural, unless otherwise specified herein, or it is clearly not inconsistent with respect to context. The terms "including", "having", "covering" and "comprising" should be construed as non-limiting terms that mean "including, but not limited to"), unless otherwise specified. The presentation of ranges of values in this document is intended solely as a way of concisely representing each individual value that is within the range, unless otherwise specified herein, and each individual value is included in the description of the invention in the same way as if it has been individually presented in this document. All methods that are described herein may be carried out in any suitable sequence, unless otherwise specified herein, or it is obviously not inconsistent with respect to the context. The use of any and all exemplary or exemplary expressions (e.g., "such as") that appear herein are for the sole purpose of better elucidating the subject matter described herein and are not intended to limit the scope of the subject matter of the present invention unless no other condition specified. No expression in the description of the present invention should be construed as defining any unclaimed element as necessary for the practical implementation of the subject matter of the invention described herein.

[0065] This document describes the preferred embodiments of the subject matter of the present application, including the best embodiment known to the authors of the present invention for carrying out the subject matter of the claimed invention. Modifications to these preferred embodiments may become apparent to those of ordinary skill in the art upon reading the above description. The authors of the present invention assume that those skilled in the art will be able to appropriately use such modifications, and the authors of the present invention assume that the subject matter of the invention described herein may be practiced in a manner other than specifically described herein. Accordingly, this disclosure extends to all modifications and equivalents of the subject matter presented in the appended claims, to the extent permitted by applicable law. In addition, the present invention extends to any combination of the elements described above in all possible appropriate modifications, unless otherwise specified herein, or it is obviously not inconsistent with respect to context.

Claims (33)

1. Compound of formula (I)

, wherein R ¹ , R ² and R ³ are independently selected from the group consisting of C ₁ -C ₅ alkyl groups. 2. The compound according to claim 1, wherein R ¹ , R ² and R ³ are independently selected from the group consisting of C ₃ -C ₅ alkyl groups. 3. A compound according to claim 1 or 2, wherein at least one of R ¹ , R ² and R ³ is a branched alkyl group. 4. The compound according to claim 3, wherein at least two of R ¹ , R ² and R ³ are branched alkyl groups. 5. The compound according to claim 4, wherein R ² and R ³ are branched alkyl groups. 6. The compound according to claim 4, wherein each of R ¹ , R ² and R ³ is a branched alkyl group. 7. The compound according to claim 1, wherein the compound is selected from the group consisting of: N-(4-isopropylcyclohexyl)-3,5-bis-[4-isopropylcyclohexylcarbonylamino]benzamide; N-(4-isopropylcyclohexyl)-3,5-bis-[4-t-butylcyclohexylcarbonylamino]-benzamide; N-(4-n-propylcyclohexyl)-3,5-bis-[4-tert-butylcyclohexylcarbonylamino]-benzamide; N-(4-n-butylcyclohexyl)-3,5-bis-[4-tert-butylcyclohexylcarbonylamino]-benzamide; N-(4-tert-butylcyclohexyl)-3,5-bis-[4-isopropylcyclohexylcarbonylamino]benzamide; N-(4-tert-butylcyclohexyl)-3,5-bis-[4-tert-butylcyclohexylcarbonylamino]-benzamide; N-(4-tert-pentylcyclohexyl)-3,5-bis-[4-tert-butylcyclohexylcarbonylamino]-benzamide; N-(4-tert-butylcyclohexyl)-3,5-bis-[4-tert-pentylcyclohexylcarbonylamino]-benzamide; N-(4-tert-pentylcyclohexyl)-3,5-bis-[4-tert-pentylcyclohexylcarbonylamino]-benzamide and their mixtures. 8. A compound according to claim 6, wherein the compound is N-(4-tert-butylcyclohexyl)-3,5-bis-[4-tert-butylcyclohexylcarbonylamino]-benzamide. 9. A compound according to claim 6, wherein the compound is N-(4-tert-butylcyclohexyl)-3,5-bis-[4-tert-pentylcyclohexylcarbonylamino]-benzamide. 10. A compound according to claim 6, wherein the compound is N-(4-tert-pentylcyclohexyl)-3,5-bis-[4-tert-butylcyclohexylcarbonylamino]-benzamide. 11. A compound according to claim 6, wherein the compound is N-(4-n-propylcyclohexyl)-3,5-bis-[4-t-butylcyclohexylcarbonylamino]-benzamide. 12. A compound according to claim 6, wherein the compound is N-(4-n-butylcyclohexyl)-3,5-bis-[4-tert-butylcyclohexylcarbonylamino]-benzamide. 13. A compound according to claim 6, wherein the compound is N-(4-isopropylcyclohexyl)-3,5-bis-[4-t-butylcyclohexylcarbonylamino]-benzamide. 14. A compound according to claim 6, wherein the compound is N-(4-tert-butylcyclohexyl)-3,5-bis-[4-isopropylcyclohexylcarbonylamino]-benzamide. 15. Polymer composition for the manufacture of molded products, containing: (a) a compound according to any one of paragraphs. 1-14 and (b) a polyolefin polymer. 16. The polymer composition according to claim 15, wherein the polyolefin polymer is a polypropylene polymer. 17. The polymer composition of claim 16, wherein the polyolefin polymer is selected from the group consisting of polypropylene homopolymers, polypropylene random copolymers, and mixtures thereof. 18. The polymer composition of claim 17, wherein the polyolefin polymer is a polypropylene random copolymer. 19. The polymer composition according to any one of paragraphs. 15-18, wherein the compound of formula (I) is present in the composition in an amount of about 0.001 wt.% or more, relative to the total weight of the polymer composition.