Tricyclodecane-dimethanol compositions and their use

Abstract

Composition comprising: a first component, which is tricyclodecanedimethanol, and a second component, wherein, when the composition is characterized in gas chromatography, the tricyclodecanedimethanol is eluted at a retention time in the range of 12.4 minutes to 13 minutes, the second component is eluted at a retention time in the range of 11.8 minutes to 12.4 minutes, each indicated by elution peaks at corresponding retention times in a spectrum, and the ratio of the area of ​​the elution peaks indicating the second component compared to the area of ​​the elution peaks indicating the tricyclodecanedimethanol is between 0.001:1 and 0.04:1.

Description

FIELD OF THE INVENTION

[0001] The present disclosure relates to a novel composition containing tricyclodecanedimethanol and is suitable as a raw material for the production of transparent optical materials. BACKGROUND

[0002] All publications contained herein are incorporated by reference to the same extent as if each individual publication or patent application were expressly and individually indicated as being incorporated by reference. The following description contains information that may be useful in understanding the invention. It does not constitute an admission that the information contained herein is prior art or relevant to the invention claimed herein, or that any publication expressly or impliedly referenced is prior art.

[0003] Optical materials or polymer materials used for electronic components and the like often require high transparency. This is due, at least in part, to their processability, which allows for a wide range of light sources for light signals. For example, a light source with a low wavelength range, such as a blue laser, a UV laser, and the like, requires an optical material with high transparency. An aromatic polyester, which has poor light transmittance or UV resistance, is difficult to use in such applications.

[0004] While various polyester resins can be formed into a film, sheet, elastomer, fiber, tube, container, or the like and used in a wide range of fields, it is important to include a suitable comonomer in the preparation to improve transparency, such as the anti-yellowing properties of the polyester resins. Similarly, polyester carbonate, polycarbonate, acrylate resin, and methacrylate resin, or the like, can be used as various optical materials, and the inclusion of a suitable comonomer to improve the transparency of the polymers would be desirable.

[0005] The aim of the present application is to provide compositions of tricycloalkanedimethanol with specific components that are suitable as raw materials for the production of downstream products with improved optical properties. BRIEF DESCRIPTION OF THE INVENTION

[0006] The following embodiments are described and illustrated in connection with systems, articles of manufacture, compositions, and methods that are intended to be exemplary and illustrative and not limiting.

[0007] Compositions are provided that contain tricyclodecanedimethanol (TCDDM), which has specific components and can be used to produce polymers or resins for applications such as the production of optical materials.

[0008] In some embodiments, the claimed composition contains a first component that is a TCDDM and a second component, wherein, when the composition is characterized in a gas chromatography (GC) analysis, the second component is eluted at a retention time in the range of 11.8 minutes to 12.4 minutes, and the ratio of the area of ​​the elution peaks indicative of the second component (e.g., peaks within the retention time range between 11.8 minutes and 12.4 minutes) compared to the area of ​​the elution peaks indicative of the TCDDM (e.g., peaks within the retention time range between 12.4 minutes and 13 minutes) is between 0.001:1 and 0.04:1. In various embodiments, the TCDDM is eluted at a retention time in the range of 12.4 minutes to 13 minutes in the GC analysis.

[0009] In some embodiments, the second component of the composition has a fragmentation pattern that includes one or more peaks with a mass-to-charge ratio (m / z) selected from the group consisting of 31, 41, 67, 79, 91, 93, 119, 149, and 167 when the composition is characterized in a gas chromatography-mass spectrometry (GC / MS) analysis. In further embodiments, the second component of the composition has a fragmentation pattern that includes at least peaks at m / z of 149 and 167. In further embodiments, the second component has a retention time in the range of 15.0 minutes to 16.5 minutes in a GC / MS analysis, while the TCDDM has a retention time in the range of 16.5 minutes to 17.5 minutes in the GC / MS analysis.

[0010] In some embodiments, a composition comprises a first component which is a TCDDM, a second component as described above, and a third component which is a compound of formula (X), wherein in a GC analysis, the ratio of the area of ​​the elution peak indicative of the compound of formula (X) compared to the area of ​​the elution peak indicative of the TCDDM is between 0.00005:1 and 0.005:1. In one embodiment, the third component of the composition elutes at a retention time in the range of 10.8 minutes to 11.2 minutes in the GC analysis.

[0011] In some embodiments, the area under the curve of the elution peaks indicative of the TCDDM is in a ratio of 0.95:1 or greater to the total area of ​​the elution peaks of the composition (without solvent).

[0012] In some embodiments, the second component is one or a mixture of compounds of formula (XI):(XI), wherein X1 = C; X2 = C; i = 1 or 0; j = 1 or 0; v = 1 or 0, if i = 1, then j = v = 0, R B1 , R B2 , R C1 , R C2 , R D1 and R G1 missing, (X3-R A ) is a linear or branched C4-alkyl alcohol, X4 = CH2 or CH(CH2OH), and if X4 = CH2, then one of R D2 , R E1 , R E2 , R F1 , R F2 and R G2 = CH2OH, while the other five of R D2 , R E1 , R E2 , R F1 , R F2 and R G2 = H; if X4= CH(CH2OH), then R D2 , R E1 , R E2 , R F1 , R F2 and R G2 =H; and if i = 0, then j = v = 1, X3 is CH, X4 is CH, one of R A , R B1 , RB2 , R C1 and R C2 is CH2OH, while the other four of R A , R B1 , R B2 , R C1 and R C2 = H, one of R D1 , R D2 , R E1 , R E2 R F1 , R F2 , R G1 and R G2 = CH2OH, another of R D1 , R D2 , R E1 , R E2 , RF F1 , R F2 , R G1 and R G2 is CH3, while the other six are from R D1 , R D2 , R E1 , R E2 , R F1 R F2 R G1 and R G2 = H.

[0013] Some embodiments provide that the second component in the compositions comprises one or more compounds of the following formulas:

[0014] Polymers are provided that can be derived from the compositions described above. For example, a polyester, an epoxy, an acrylate, a polycarbonate, or a polyurethane can be synthesized or modified to contain the composition described above. The polymers can be processed into an optical material that can be used in various applications such as an optical disk, a fiber, or a lens. BRIEF DESCRIPTION OF THE CHARACTERS Fig. Figure 1 is a retention time spectrum of GC analysis of the TCDDM-based composition of Example 4. Fig. 2A and Fig. Figure 2B are retention time spectra in the GC / MS analysis of the TCDDM-based composition of Example 4. Fig. Figure 3 is a photograph of the TCDDM-based composition of Example 6 (in the inverted bottle on the left) and that of Comparative Example 2 (in the inverted bottle on the right). DETAILED DESCRIPTION OF THE INVENTION

[0015] All references cited herein are incorporated by reference in their entirety as if fully set forth. Unless otherwise defined, technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. Unless otherwise indicated or clear from the context, the following terms and expressions have the meanings set forth below. Unless expressly stated otherwise or clear from the context, the following terms and expressions do not exclude the meaning that the term or expression has acquired in the art to which it belongs. Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs.This application is not limited to the methods, protocols, reagents, etc. described herein and may therefore vary. The definitions and terms used herein are intended to describe particular embodiments and are not intended to limit the claimed invention.

[0016] One skilled in the art will recognize many methods and materials similar or equivalent to those described herein that could be used in the practice of the present application. Further features and advantages of the present application will become apparent from the following detailed description. Indeed, the present application is in no way limited to the methods and materials described. For convenience, certain terms used herein, in the specification, examples, and appended claims, are collected here.

[0017] As used herein, the term "comprising" or "comprises" refers to compositions, methods, processes, articles of manufacture, systems, and corresponding components thereof that are useful for an embodiment, but open to the inclusion of unspecified elements, whether useful or not. Those skilled in the art will understand that the terms used herein are generally intended to be "open-ended" terms (e.g., the term "including" should be interpreted as "including, but not limited to," the term "having" as "having at least," the term "comprises" as "comprises, but not limited to," etc.).Although the open term "comprising" is used synonymously with terms such as "including," "containing," or "having" to describe and claim the present application, the invention or its embodiments may alternatively be described using other terms such as "consisting of" or "consisting essentially of."

[0018] Unless otherwise specified, the terms "a" and "an" and "the" and similar references used in connection with the description of a particular embodiment of the application (particularly in connection with the claims) may be construed to include both the singular and the plural. The enumeration of the ranges of values ​​of is intended merely as a shorthand method to refer individually to each value that falls within the range. Unless otherwise specified herein, each individual value is included in the specification as if listed individually. All processes described herein may be performed in any suitable order unless otherwise specified herein or the context clearly indicates otherwise. The use of examples or exemplary expressions (e.g.,References to specific embodiments (e.g., "such as") are intended merely to better illustrate the application and do not limit the scope of the otherwise claimed application. The abbreviation "e.g." is derived from the Latin exempli gratia (English, eg) and is used herein to indicate a non-limiting example. Therefore, the abbreviation "e.g." is synonymous with the term "for example." No language in the description should be construed as pointing to an unclaimed element that is essential to the practice of the application.

[0019] “Optional” or “optional” means that the circumstance described below may or may not occur, so that the description includes both cases in which the circumstance occurs and cases in which it does not occur.

[0020] The term "approximately" used here can mean plus or minus 20% of the specified value. For example, approximately 75 °C covers the range from 60 °C to 90 °C.

[0021] Various embodiments of the present application provide TCDDM-based compositions suitable for producing polyesters with high transparency or low opacity and meeting the requirements of industrial applications

[0022] In some embodiments, a TCDDM-based composition, when dissolved in a solvent for GC analysis (spectrum in Fig.), a first component (i.e., TCDDM) which is eluted at a retention time of 12.4 minutes to 13 minutes, and a second component which is eluted from 11.8 minutes to 12.4 minutes, and the ratio of the area of ​​the elution peak indicative of the second component compared to the area of ​​the elution peak indicative of the first component is between 0.001:1 and 0.04:1, wherein the GC analysis includes eluting the TCDDM-based composition from a BP-5 capillary column with a length of 30 meters, an inner diameter of 530 µm and a film thickness of 1 µm, characterized by a liquid phase of 5% phenyl and 95% dimethyl polysiloxane and a carrier gas of nitrogen flowed through at 5 mL / min for an initial 11 minutes, followed by a stepwise flow rate of 5 mL / min to 10 mL / min in a rate increment of 1 mL / min (and then maintained at 10 mL / min until the end of the GC analysis),at a stepwise temperature in a sequence of 50 °C for 1 minute, then increasing the temperature from 50 °C to 180 °C in an increment of 15 °C / min, then increasing the temperature from 180 °C to 250 °C in an increment of 30 °C / min, followed by 250 °C for 8 minutes, wherein an inlet temperature is 250 °C, a sample injection volume of the composition is 2 µL, and a detector is a flame ionization detector operating at 300 °C. In various embodiments, the area of ​​the elution peak(s) indicative of a component is defined as the area in a GC spectrum that lies below an elution curve (e.g., it may be a singlet, doublet, triplet, etc. peak or multiple peaks as long as it lies within a certain retention time range of the component) and above a baseline typically established by the GC operating system.

[0023] In one embodiment, a composition is characterized by GC analysis wherein the ratio of the area of ​​the elution peaks indicating the second component to the area of ​​the elution peaks indicating the first component is between 0.001:1 and 0.04:1.

[0024] In another embodiment, a composition is characterized by GC analysis wherein the ratio of the area of ​​the elution peaks indicative of the second component to the area of ​​the elution peaks indicative of the first component is between 0.001:1 and 0.039:1.

[0025] In another embodiment, a composition is characterized by GC analysis wherein the ratio of the area of ​​the elution peaks indicating the second component to the area of ​​the elution peaks indicating the first component is between 0.0012:1 and 0.039:1.

[0026] In a further embodiment, a composition is characterized by GC analysis in which the ratio of the area of ​​the elution peaks indicating the second component to the area of ​​the elution peaks indicating the first component is between 0.0012:1 and 0.027:1.

[0027] In some embodiments, a composition characterized by GC analysis has a ratio of the area of ​​the elution peaks indicating the second component compared to the area of ​​the elution peaks indicating the first component of 0.001:1, 0.002:1, 0.003:1, 0.004:1, 0.005:1, 0.006:1, 0.007:1, 0.008:1, 0.009:1, 0.01:1, 0.011:1, 0.012:1, 0.013:1, 0.014:1, 0.015:1, 0.016:1, 0.017:1, 0.018:1, 0.019:1, 0.02:1, 0.021:1, 0.022:1, 0.023:1, 0.024:1, 0.025:1, 0.026:1, 0.027:1, 0.028:1, 0.029:1, 0.03:1, 0.031:1, 0.032:1, 0.033:1, 0.034:1, 0.035:1, 0.036:1, 0.037:1, 0.038:1, 0.039:1, 0.04:1, or a ratio between any two values.

[0028] Further embodiments of the compositions provide that, in GC analysis, the area of ​​the elution peaks of the second component relative to the total area of ​​the elution peaks of a composition without the solvent is between 0.001:1 and 0.04:1; or that the ratio of the area of ​​the elution peaks indicative of the second component compared to the total area of ​​the elution peaks indicative of the composition (without a solvent) is between 0.001:1 and 0.04:1. The total area of ​​the elution peaks of the composition (i.e., without the solvent) typically includes the area of ​​the elution peaks indicative of the first component and the area of ​​the elution peaks indicative of the second component.

[0029] In a further embodiment of the compositions characterized by GC analysis, the area of ​​the elution peaks of the second component relative to the total area of ​​the elution peaks excluding that of the solvent is between 0.001:1 and 0.039:1; or, in other words, the ratio of the area of ​​the elution peaks indicative of the second component to the total area of ​​the elution peaks indicative of the composition (without a solvent) is between 0.001:1 and 0.039:1.

[0030] In another embodiment of the compositions characterized by GC analysis, the area of ​​the elution peaks of the second component relative to the total area of ​​the elution peaks excluding that of the solvent is between 0.001:1 and 0.038:1; or, in other words, the ratio of the area of ​​the elution peaks indicative of the second component to the total area of ​​the elution peaks indicative of the composition (without a solvent) is between 0.001:1 and 0.038:1.

[0031] In another embodiment of the compositions characterized by GC analysis, the area of ​​the elution peaks of the second component relative to the total area of ​​the elution peaks excluding that of the solvent is between 0.0012:1 and 0.038:1; or, expressed differently, the ratio of the area of ​​the elution peaks indicative of the second component to the total area of ​​the elution peaks indicative of the composition (without a solvent) is between 0.0012:1 and 0.038:1.

[0032] In a further embodiment of the compositions characterized by GC analysis, the area of ​​the elution peaks of the second component relative to the total area of ​​the elution peaks excluding that of the solvent is between 0.0012:1 and 0.027:1; or, in other words, the ratio of the area of ​​the elution peaks indicative of the second component to the total area of ​​the elution peaks indicative of the composition (without a solvent) is between 0.0012:1 and 0.027:1.

[0033] A further embodiment of the compositions provides that, when characterized by GC analysis, the area of ​​the elution peaks indicating the second component relative to the total area of ​​the elution peaks of a composition without that of the solvent 0.001, 0.002, 0.003, 0.004, 0.005, 0.006, 0.007, 0.008, 0.009, 0.01, 0.011, 0.012, 0.013, 0.014, 0.015, 0.016, 0.017, 0.018, 0.019, 0.02, 0.021, 0.022, 0.023, 0.024, 0.025, 0.026, 0.027, 0.028, 0.029, 0.03, 0.031, 0.032, 0.033, 0.034, 0.035, 0.036, 0.037, 0.038, 0.039, 0.04 or a number between two of the listed values.Further embodiments of the compositions provide that, when characterized by GC analysis, the ratio of the area of ​​the elution peaks indicative of the second component compared to the total area of ​​the elution peaks indicative of the composition (without a solvent) is 0.001:1, 0.002:1, 0.003:1, 0.004:1, 0.005:1, 0.006:1, 0.007:1, 0.008:1, 0.009:1, 0.01:1, 0.011:1, 0.012:1, 0.013:1, 0.014:1, 0.015:1, 0.016:1, 0.017:1, 0.018:1, 0.019:1, 0.02:1, 0.021:1, 0.022:1, 0.023:1, 0.024:1, 0.025:1, 0.026:1, 0.027:1, 0.028:1, 0.029:1, 0.03:1, 0.031:1, 0.032:1, 0.033:1, 0.034:1, 0.035:1, 0.036:1, 0.037:1, 0.038:1, 0.039:1, 0.04:1, or a ratio between any two values.

[0034] The compositions of the present application, in some embodiments, comprise a third component that elutes in GC analysis at a retention time of 10.8 minutes to 11.2 minutes, wherein the ratio of the area of ​​the elution peak indicative of the third component (e.g., peak(s) within a retention time range between 10.8 minutes and 11.2 minutes) compared to the area of ​​the elution peaks indicative of the first component is between 0.00005:1 and 0.005:1.

[0035] In one embodiment of the compositions characterized by GC analysis, the ratio of the area of ​​the elution peak indicating the third component compared to the area of ​​the elution peaks indicating the first component is between 0.00005:1 and 0.0018:1.

[0036] In one embodiment of the compositions characterized by GC analysis, the ratio of the area of ​​the elution peak indicating the third component compared to the area of ​​the elution peaks indicating the first component is between 0.0001:1 and 0.0018:1.

[0037] In still other embodiments of the compositions, the ratio of the area of ​​the elution peak indicating the third component to the area of ​​the elution peaks indicating the first component is 0.00005:1, 0.00006:1, 0.00007:1, 0.00008:1, 0.00009:1, 0.0001:1, 0.0002:1, 0.0003:1, 0.0004:1, 0.0005:1, 0.0006:1, 0.0007:1, 0.0008:1, 0.0009:1, 0.001:1, 0.0011:1, 0.0012:1, 0.0013:1, 0.0014:1, 0.0015:1, 0.0016:1, 0.0017:1, 0.0018:1, 0.0019:1, 0.002:1, 0.0021:1, 0.0022:1, 0.0023:1, 0.0024:1, 0.0025:1, 0.0026:1, 0.0027:1, 0.0028:1, 0.0029:1, 0.003:1, 0.0031:1, 0.0032:1, 0.0033:1, 0.0034:1, 0.0035:1, 0.0036:1, 0.0037:1, 0.0038:1, 0.0039:1, 0.004:1, 0.0041:1, 0.0042:1, 0.0043:1, 0.0044:1, 0.0045:1, 0.0046:1, 0.0047:1, 0.0048:1, 0.0049:1, 0.005:1 or a ratio between any of the two listed values.

[0038] Further embodiments of the compositions provide that, in GC analysis, the ratio of the area of ​​the elution peak indicative of the third component to the total area of ​​the elution peaks indicative of a composition (without the solvent) is between 0.00005:1 and 0.005:1, between 0.00005:1 and 0.0018:1, or between 0.0001:1 and 0.0018:1. Various embodiments provide that the total area of ​​the elution peaks of the composition (i.e., without the solvent) includes the area of ​​the elution peaks indicative of the first component, the area of ​​the elution peaks indicative of the second component, and the area of ​​the elution peak indicative of the third component.In further embodiments, the ratio of the area of ​​the elution peak indicating the third component to the total area of ​​the elution peak indicating the composition (excluding that of the solvent) is 0.00005:1, 0.00006:1, 0.00007:1, 0.00008:1, 0.00009:1, 0.0001:1, 0.0002:1, 0.0003:1, 0.0004:1, 0.0005:1, 0.0006:1, 0.0007:1, 0.0008:1, 0.0009:1, 0.001:1, 0.0011:1, 0.0012:1, 0.0013:1, 0.0014:1, 0.0015:1, 0.0016:1, 0.0017:1, 0.0018:1, 0.0019:1, 0.002:1, 0.0021:1, 0.0022:1, 0.0023:1, 0.0024:1, 0.0025:1, 0.0026:1, 0.0027:1, 0.0028:1, 0.0029:1, 0.003:1, 0.0031:1, 0.0032:1, 0.0033:1, 0.0034:1, 0.0035:1, 0.0036:1, 0.0037:1, 0.0038:1, 0.0039:1, 0.004:1, 0.0041:1, 0.0042:1, 0.0043:1, 0.0044:1, 0.0045:1, 0.0046:1, 0.0047:1, 0.0048:1, 0.0049:1, 0.005:1 or a ratio between any of the two listed values.

[0039] Further embodiments of the compositions provide that, when characterized by GC analysis, the ratio of the area of ​​the elution peaks indicative of the first component compared to the total area of ​​the elution peaks indicative of composition (excluding that of the solvent) is at least 0.95:1.

[0040] In one embodiment, the ratio of the area of ​​the elution peaks indicative of the first component compared to the total area of ​​the elution peaks indicative of composition (excluding the area of ​​the solvent) is 0.95:1, 0.951:1, 0.952:1, 0.953:1, 0.954:1, 0.955:1, 0.956:1, 0.957:1, 0.958:1, 0.959:1, 0.96:1, 0.961:1, 0.962:1, 0.963:1, 0.964:1, 0.965:1, 0.966:1, 0.967:1, 0.968:1, 0.969:1, 0.97:1, 0.971:1, 0.972:1, 0.973:1, 0.974:1, 0.975:1, 0.976:1, 0.977:1, 0.978:1, 0.979:1, 0.98:1, 0.981:1, 0.982:1, 0.983:1, 0.984:1, 0.985:1, 0.986:1, 0.987:1, 0.988:1, 0.989:1, 0.99:1, 0.991:1, 0.992:1, 0.993:1, 0.994:1, 0.995:1, 0.996:1, 0.997:1, 0.998:1, 0.999:1 or a ratio between any two of the listed values.

[0041] Suitable solvents for the compositions of the present application in a GC analysis may be those that do not adversely affect (e.g., degrade) the composition, the GC column, or the GC equipment. Exemplary solvents for the compositions in a GC analysis include, but are not limited to, methanol, isopropanol, acetone, tetrahydrofuran, or a mixture thereof.

[0042] Further embodiments of the compositions are characterized by a GC / MS analysis (example spectra are shown in Fig. 2A and Fig.2B), wherein the second component of the composition has a retention time of 15.0 minutes to 16.5 minutes and a fragmentation pattern including one or more peaks at a mass-to-charge ratio (m / z) selected from the group consisting of 31, 41, 67, 79, 91, 93, 119, 149, and 167, wherein the GC / MS analysis comprises eluting the composition from a BP-1 capillary column having a length of 60 meters, an inner diameter of 320 µm, and a film thickness of 1 µm with a liquid phase of 100% dimethylpolysiloxane and a carrier gas of helium flowing at 2 ml / min, at an inlet temperature of 250 °C and operating at a step temperature in a sequence of 50 °C for 2 minutes, then increasing the temperature from 50 °C to 180 °C at a step of 15 °C / min, then temperature increase from 180 °C to 250 °C at a step of 30 °C / min, followed by 250 °C for 6 minutes, and operated with an electron energy of 70 eV,an electron source temperature of 230 °C, a quadrupole mass filter temperature of 150 °C and a mass scan in a range between 20.0 m / z and 230.0 m / z with a solvent delay of 0 minutes.

[0043] One embodiment of the compositions provides that the second component of the composition, when characterized in GC / MS analysis, exhibits a fragmentation pattern with peaks at m / z 31, 41, 67, 79, 91, 93 and 119.

[0044] A further embodiment of the compositions provides that the second component of the composition, when characterized in GC / MS analysis, has a retention time of 15.8 minutes to 16.0 minutes with a fragmentation pattern comprising peaks at m / z of 149 and 167.

[0045] A further embodiment of the compositions provides that, when characterized in GC / MS analysis, the second component of the composition has a retention time of 15.8 minutes to 16.0 minutes with a fragmentation pattern that further includes one or more peaks at m / z selected from the group consisting of 31, 41, 67, 79, 91, 93, and 119.

[0046] A further embodiment of the compositions provides that, when characterized in GC / MS analysis, the second component of the composition has a retention time of 15.8 minutes to 16.0 minutes with a fragmentation pattern including peaks at m / z of at least 31, 41, 67, 79, 91, 93, 119, 149 and 167.

[0047] One embodiment of the compositions provides that, when characterized in GC / MS analysis, the second component of the composition has a retention time of 16.2 minutes to 16.4 minutes with a fragmentation pattern including peaks at m / z of 149 and 167.

[0048] A further embodiment of the compositions provides that the second component of the composition, when characterized in GC / MS analysis, has a retention time of 16.2 minutes to 16.4 minutes with a fragmentation pattern that further includes one or more peaks at m / z of 31, 41, 67, 79, 91, 93 and 119.

[0049] A further embodiment of the compositions provides that the second component of the composition, when characterized in GC / MS analysis, has a retention time of 16.2 minutes to 16.4 minutes with a fragmentation pattern comprising peaks at m / z of 31, 41, 67, 79, 91, 93, 119, 149 and 167.

[0050] Further embodiments of the compositions provide that the first component of the composition, when characterized in GC / MS analysis, has a retention time of 16.5 minutes to 17.5 minutes, and in some embodiments with a fragmentation pattern including peaks at m / z of one or more of 31, 41, 67, 79, 91, 93, 119, 147, 165, and 178.

[0051] In one embodiment, the first component of the compositions exhibits a fragmentation pattern with peaks at m / z of 31, 41, 67, 79, 91, 93, and 119 in GC / MS analysis.

[0052] In another embodiment, the first component of the compositions exhibits a fragmentation pattern in the GC / MS analysis that includes peaks at m / z 147, 165, and 178. In another embodiment, the first component of the composition exhibits a fragmentation pattern in the GC / MS analysis with peaks at m / z 31, 41, 67, 79, 91, 93, 119, 147, 165, and 178.

[0053] In further embodiments of the compositions, the third component elutes with a retention time of 14.0 minutes to 14.5 minutes in the GC / MS analysis. In further embodiments, the third component exhibits a fragmentation pattern in the GC / MS analysis that includes a peak at m / z 135.

[0054] The compositions of the present application contain a first component which is TCDDM. In some embodiments of the compositions, the TCDDM has a chemical structure represented by formula (II):

[0055] In some embodiments of the compositions, the TCDDM is selected from at least one of 3,8-bis(hydroxymethyl)tricyclo[5.2.1.0 2-6 ]decane; 3,9-Bis(hydroxymethyl)tricyclo[5.2.1.0 2-6 ]decane; 4,8-Bis(hydroxymethyl)tricyclo[5.2.1.02 -6 ]decane; 4,9-Bis(hydroxymethyl)tricyclo[5.2.1.0 2-6 ]decane; 5,8-Bis(hydroxymethyl)tricyclo[5.2.1.0 2-6 ]decane; and 5,9-bis(hydroxymethyl)tricyclo[5.2.1.0 2-6 ]decan.

[0056] In some embodiments of the compositions, the second component is an aliphatic diol. In one embodiment, the second component is a C12 aliphatic diol (having 12 carbon atoms or C 12). In another embodiment, the second component is a saturated C12-cycloaliphatic diol. In further embodiments, the second component is one or a mixture of compounds represented by the formula (XI): wherein (1) X1 = C, (2) X2 = C; (3) i = 1 or 0; (4) j = 1 or 0; (5) v = 1 or 0; and (6) when i = 1, then j = v = 0, R B1 , R B2 , R C1 , R C2 , R D1 and R G1 are absent, (X (3) -R A ) is a linear or branched C4 (4-carbon) alkyl alcohol, X4 is CH2 or CH(CH2OH), and when X4 = CH2, then one of R D2 , R E1 , R E2 , R F1 , R F2 and R G2 = CH2OH, while the other five of R D2 , R E1 , R E2 , R F1 , R F2 and R G2 H; if X4 = CH(CH2OH), then R D2 , R E1 , R E2 , R F1, R F2 and R G2 = H; (7) if i = 0, then j = v = 1, X3 is CH, X4 is CH, one of R A , R B1 , R B2 , R C1 and R C2 is CH2OH, while the other four of R A , R B1 , R B2 , R C1 and R C2 = H, one of R D1 , R D2 , R E1 , R E2 , R F1 R F2 R G1 and R G2 = CH2OH, another of R D1 , R D2 , R E1 , R E2 , R F1 , R F2 , R G1 and R G2 = CH3, while the other six of R D1 , R D2 , R E1 , R E2 , R F1 , R F2 , R G1 and R G2 = H. In a further embodiment, the second component of the compositions comprises one or more of the following elements:In each of the

[0057] Formulas (XV)-(XX) one of the hydroxymethyl groups may be bonded to the same carbon to which a methyl group is bonded in the cycloalkane ring, therefore the second component of the composition may be:

[0058] Some embodiments of the compositions provide that the third component is tricyclodecane monomethanol (TCDM). In some embodiments, TCDM has a chemical structure represented by the formula (X):

[0059] In other embodiments, the third component of the compositions is a saturated cycloaliphatic C11 (11-carbon) compound having a hydroxyl group.

[0060] In further embodiments, the third component of the compositions is selected from at least one of 4-hydroxymethyltricyclo[5.2.1.0 2-6 ]decane, 3-Hydroxymethyltricyclo[5.2.1.0 2-6 ]decane and 5-hydroxymethyltricyclo[5.2.1.0 2-6 ]decan.

[0061] The compositions of the present application may contain one or more components in addition to the first, second and / or third components described above, wherein the additional components do not adversely affect the properties of the compositions for the intended applications.Exemplary additional components include, but are not limited to, an acetal-containing compound, an amine-containing compound such as tertiary amines (trimethylamine, triethylamine, tri-n-butylamine, tri-n-octylamine, triethanolamine, N-methyldiethanolamine, and N,N-dimethylethanolamine), aromatic tertiary amines (N,N-dimethylaniline, N,N-diethylaniline, and triphenylaniline), and heterocyclic tertiary amines (pyridine and quinoline); an alcohol-containing compound, such as ethylene glycol, 1,3-propanediol, 1,2-propanediol, 1,4-butanediol, 1,2-butanediol, 1,3-butanediol, 2,3-butanediol, 2-methyl-1,4-butanediol, 1,5-pentanediol, 2-methyl-1,3-propanediol, 2-methyl-1,3-pentanediol, 2-methyl-1,5-pentanediol, 3-methyl-1,5-pentanediol, 2,4-diethyl-1,5-pentanediol, neopentyl glycol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, glycerin, pentaerythritol, 2-methyl-1,8-octanediol, 1,9-nonanediol, 1,10-decanediol and trimethylolpropane; or an aldehyde-containing compound, such astricyclodecanedicarbaldehyde and pentacyclopentadecanedicarbaldehyde.

[0062] The compositions of the present application may also contain one or more additives. Exemplary additives do not impair the compositions for the intended applications and include, but are not limited to, stabilizers, antioxidants, lubricants, flame retardants, carbon black, dyes, defoamers, dispersants, viscosity modifiers, thixotropic agents, leveling agents, adhesion promoters, mold release agents, anti-mold agents, antibacterial agents, or the like.

[0063] In some embodiments, the TCDDM-based compositions of the present invention can be used as optical materials. In some embodiments, the TCDDM-based compositions of the present application are admixed with polyester, epoxy, acrylate, polycarbonate, polycarbonatediol, and / or polyurethane resins or optical products thereof. In some embodiments, TCDDM-based compositions of the present application are used to produce polyester, epoxy, acrylate, polycarbonate, polycarbonatediol, and / or polyurethane, and the polymer containing the TCDDM residue is processed into an optical disc, fiber, or lens.

[0064] In some embodiments, polyesters can be prepared using the TCDDM-based compositions and a carboxylic acid-containing compound, such as a benzenedicarboxylic acid, a benzenetricarboxylic acid, or both, and optionally in further combination with an alkanediol. An example of a benzenedicarboxylic acid is a phthalic acid (1,2-benzenedicarboxylic acid), isophthalic acid (1,3-benzenedicarboxylic acid), or terephthalic acid (1,4-benzenedicarboxylic acid). Examples of benzenetricarboxylic acids are trimesic acid (benzene-1,3,5-tricarboxylic acid) or trimellitic acid (benzene-1,2,4-tricarboxylic acid). An alkanediol can be a linear or branched C2-C6 alkane having two hydroxyl groups.

[0065] In one embodiment, a polyester is prepared from a TCDDM-based composition, terephthalic acid, trimellitic acid, and ethylene glycol. In the CIELAB color space, the b* scale indicates yellowing. Polyesters derived from the TCDDM-based compositions of the present application exhibit improved yellowing resistance.

[0066] The compositions of the present application can be prepared by one or more processes. For example, the composition is prepared by hydroformylation of dicyclopentadiene (DCPD), followed by phase separation and extraction, which is then hydrogenated. Alternatively, the hydrogenated product can be distilled by any known method; for example, the skilled person can adjust the height of the distillation column or the theoretical stages. In a further embodiment, the skilled person can adjust the reflux ratio or the distillation pressure, or add a metal compound in a distillation process. The various preparation processes mentioned above do not imply that the compositions of the present application can only be prepared by these processes.

[0067] Exemplary methods for preparing the compositions of the present application are described below.

[0068] Various embodiments provide that the described compositions of the present application are prepared by a hydrogenation process of tricyclodecanedialdehyde. Further embodiments provide that a disclosed composition is prepared by a hydrogenation process of a tricyclodecanedialdehyde obtained from or as a component within an aqueous extraction layer of the hydroformylation product of dicyclopentadiene. In some embodiments, the hydrogenation process comprises introducing hydrogen gas at elevated pressure, for example, between about 2 MPa and 10 MPa, into the tricyclodecanedialdehyde or into the hydroformylation product of dicyclopentadiene, and the hydroformylation product of dicyclopentadiene contains at least tricyclodecanedialdehyde.In further embodiments, the hydrogenation process is carried out at a temperature in the range between 40°C and 200°C or between about 60°C and 150°C. In another embodiment, the hydrogenation is carried out in the presence of a catalyst such as nickel, aluminum, or a combination thereof, or by addition to the reactant. Further hydrogenation processes are disclosed in U.S. Patent No. 6,365,782, the contents of which are incorporated herein by reference.

[0069] The disclosure is further illustrated by the following examples, which should not be construed as limiting. The examples are for illustrative purposes only and are not intended to limit any of the embodiments described herein. The following examples do not limit the invention in any way. EXAMPLES

[0070] The following examples are not intended to limit the scope of the claims, but rather to be exemplary of particular embodiments. All variations of the exemplary methods that occur to one skilled in the art are intended to be within the scope of the invention.

[0071] The present application is further illustrated by the following examples, which are intended to be merely exemplary of the invention and should not be considered as limiting the invention in any way. The following examples serve to better illustrate the claimed invention and are not to be construed as limiting the scope of the invention. Where specific materials are mentioned, this is for illustrative purposes only and is not intended to limit the invention. Those skilled in the art may devise equivalent agents or reactants without exercising their inventive skill and without departing from the scope of the invention. TCDDM-based compositions manufacturing example

[0072] The hydroformylation to obtain the aldehyde compound as a precursor to the TCDDM-based composition was carried out under an atmosphere of hydrogen and carbon monoxide in a ratio of 1:1. Specifically, 100 g of methylcyclohexane, 0.015 g of Rh(acac)(CO)2 (Aldrich), and 4.5 g of tris-(2,4-di-t-butylphenyl)phosphite (BASF) were mixed to form a hydroformylation mixture. The hydroformylation mixture was heated to 70 °C for 1.5 hours to dissolve it evenly. After this process, the hydroformylation mixture was purified at a pressure of 1 kg / cm 2 G into an autoclave. The temperature and pressure of the autoclave were then adjusted to 80 °C and 50 kg / cm 2G. 50 g of dicyclopentadiene (DCPD) (Zeon) were continuously fed into the autoclave at a rate of 0.83 g / min over a period of 30 minutes using a duplex pump. The reaction was carried out for 12 hours at a pressure of 50 kg / cm 2 G. After completion of the reaction, a non-aqueous solution of the hydroformylation product was obtained. Example 1.

[0073] The non-aqueous solution of the hydroformylation product (174.5 g) from Preparation Example and an aqueous extraction solvent containing 2-methyl-1,3-propanediol (MPO), methanol, and water in a weight ratio of 1:7:2 (MPO:methanol:water) were mixed in a mass ratio of 1:1 (non-aqueous solution of the hydroformylation product:aqueous extraction solvent) and stirred in a mixer maintained at a temperature of 25°C. After stirring for 1 hour, the mixture was poured into a glass extractor and allowed to stand for 2 hours to obtain a two-phase mixture (non-aqueous hydroformylation solvent layer (i.e., non-polar phase) and aqueous extraction solvent layer (i.e., polar phase)). The extraction temperature was maintained at 25°C.Subsequently, 0.5 g of nickel / Al2O3 was added to 100 g of the aqueous extraction layer, and a hydrogen gas pressure of 5 MPa was introduced to conduct the hydrogenation process at a temperature of 60 °C for approximately 3 hours. The hydrogenation product (253.1 g) was then distilled on a Claisen head with a condenser at a pressure of 12 hPa, yielding the TCDDM-based composition (57.1 g) with a boiling range of 170 °C–210 °C. Example 2.

[0074] The non-aqueous hydroformylation product solution (174.5 g) obtained from Preparation Example and an aqueous extraction solvent containing tricyclo[5.2.1.0(2,6)]decanedimethanol, methanol, and water in a weight ratio of 1:7:2 (tricyclo[5.2.1.0(2,6)]decanedimethanol:methanol:water) in a mass ratio of 1:1 (non-aqueous hydroformylation product solution:aqueous extraction solvent) were mixed and stirred in a mixer at a temperature of 35 °C. After stirring for 1 hour, the mixture was poured into a glass extractor and allowed to stand for 2 hours to form a two-phase mixture. The extraction temperature was maintained at 35 °C. Subsequently, 0.5 g of nickel / Al2O3 was added to 100 g of the aqueous extraction layer and a hydrogen gas pressure of 8 MPa was introduced to continue the hydrogenation process at a temperature of 80 °C for about 3 hours.The hydrogenation product (252.4 g) was then distilled on a Claisen head with a condenser at a pressure of 10 hPa and the TCDDM-based composition (75.1 g) was obtained in a boiling range of 170 °C-210 °C. Example 3.

[0075] The non-aqueous solution of the hydroformylation product (174.5 g) from Preparation Example and an aqueous extraction solvent containing MPO, methanol, and water in a weight ratio of 7:1:2 (MPO:methanol:water) were mixed in a mass ratio of 1:1 (non-aqueous solution of the hydroformylation product: aqueous extraction solvent) and stirred in a mixer maintained at a temperature of 70 °C. After stirring for 1 hour, the mixture was poured into a glass extractor and allowed to stand for 2 hours to obtain a two-phase mixture. The extraction temperature was maintained at 70 °C. Subsequently, 0.5 g of nickel / Al2O3 was added to 100 g of the aqueous extraction layer, and a hydrogen gas pressure of 2 MPa was introduced to conduct the hydrogenation process at a temperature of 150 °C for approximately 3 hours. After the hydrogenation process, the pressure was released and the reaction was cooled to room temperature.The hydrogenation product (264.7 g) was then distilled on a Claisen head with a condenser at a pressure of 5 hPa and the TCDDM-based composition (60.35 g) was obtained in a boiling range of 170 °C-210 °C. Example 4.

[0076] The non-aqueous solution of the hydroformylation product (174.5 g) from Preparation Example and an aqueous extraction solvent containing cyclohexanedimethanol (CHDM), methanol, and water in a weight ratio of 1:6:3 (CHDM: methanol: water) were mixed in a mass ratio of 1:1 (non-aqueous solution of the hydroformylation product: aqueous extraction solvent) and stirred in a mixer maintained at a temperature of 30 °C. After stirring for 1 hour, the mixture was poured into a glass extractor and allowed to stand for 2 hours to obtain a two-phase mixture. The extraction temperature was maintained at 30 °C. Subsequently, 0.5 g of nickel / Al2O3 was added to 100 g of the aqueous extraction layer, and a hydrogen gas pressure of 4 MPa was introduced to continue the hydrogenation process at a temperature of 80 °C for about 3 hours.After the hydrogenation process, the pressure was released and the reaction cooled to room temperature. The hydrogenation product (258.7 g) was then distilled on a Claisen head with a condenser at a pressure of 4 hPa, yielding the TCDDM-based composition (60.23 g) with a boiling range of 170 °C–210 °C. Example 5.

[0077] The non-aqueous solution of the hydroformylation product (174.5 g) from Preparation Example and an aqueous extraction solvent containing MPO, methanol, and water in a weight ratio of 3:5:2 (MPO:methanol:water) were mixed in a mass ratio of 1:1 (non-aqueous solution of the hydroformylation product: aqueous extraction solvent) and stirred in a mixer maintained at a temperature of 20 °C. After stirring for 1 hour, the mixture was poured into a glass extractor and allowed to stand for 2 hours to form a two-phase mixture. The extraction temperature was maintained at 20 °C. Subsequently, 0.5 g of nickel / Al2O3 was added to 100 g of the aqueous extraction layer, and a hydrogen gas pressure of 9 MPa was introduced to conduct the hydrogenation process at a temperature of 100 °C for approximately 3 hours. After the hydrogenation process, the pressure was released and the reaction was cooled to room temperature.The hydrogenation product (257.9 g) was then distilled on a Claisen head with a condenser at a pressure of 4 hPa and the TCDDM-based composition (59.42 g) was obtained in a boiling range of 170 °C-210 °C. Example 6.

[0078] The non-aqueous solution of the hydroformylation product (174.5 g) from Preparation Example and an aqueous extraction solvent containing MPO, ethanol (EtOH), and water in a weight ratio of 1:6:3 (MPO:EtOH:water) were mixed in a mass ratio of 1:1 (non-aqueous solution of the hydroformylation product: aqueous extraction solvent) and stirred in a mixer maintained at a temperature of 40 °C. After stirring for 1 hour, the mixture was poured into a glass extractor and allowed to stand for 2 hours to obtain a two-phase mixture. The extraction temperature was maintained at 40 °C. Subsequently, 0.5 g of nickel / Al2O3 was added to 100 g of the aqueous extraction layer, and a hydrogen gas pressure of 4 MPa was introduced to continue the hydrogenation process at a temperature of 120 °C for approximately 3 hours. After the hydrogenation process, the pressure was released and the reaction was cooled to room temperature.The hydrogenation product (264.2 g) was then distilled on a Claisen head with a condenser at a pressure of 8 hPa and the TCDDM-based composition (58.42 g) was obtained in a boiling range of 170 °C-210 °C. Example 7.

[0079] The non-aqueous hydroformylation product solution (174.5 g) obtained from Preparation Example and an aqueous extraction solvent containing tricyclo[5.2.1.0(2,6)]decanedimethanol, methanol, and water in a weight ratio of 1:6:3 (tricyclo[5.2.1.0(2,6)]decanedimethanol:methanol:water) in a mass ratio of 1:1 (non-aqueous hydroformylation product solution:aqueous extraction solvent) were mixed and stirred in a mixer maintained at a temperature of 55°C. After stirring for 1 hour, the mixture was poured into a glass extractor and allowed to stand for 2 hours to obtain a two-phase mixture. The extraction temperature was maintained at 55°C. Subsequently, 0.5 g of nickel / Al2O3 was added into 100 g of the aqueous extraction layer and a hydrogen gas pressure of 7 MPa was introduced to carry out the hydrogenation process at a temperature of 85 °C for about 3 hours.After the hydrogenation process, the pressure was released and the reaction cooled to room temperature. The hydrogenation product (254.1 g) was then distilled on a Claisen head with a condenser at a pressure of 6 hPa, yielding the TCDDM-based composition (75.5 g) with a boiling range of 170 °C–210 °C. Example 8.

[0080] The non-aqueous hydroformylation product solution (174.5 g) obtained from the preparation example and an aqueous extraction solvent containing MPO, methanol, and water in a weight ratio of 8:1.5:0.5 (MPO:methanol:water) were mixed in a mass ratio of 1:1 (non-aqueous hydroformylation product solution:aqueous extraction solvent) and stirred in a mixer maintained at a temperature of 30°C. After stirring for 1 hour, the mixture was poured into a glass extractor and allowed to stand for 2 hours to obtain a two-phase mixture. The extraction temperature was maintained at 30°C. Subsequently, 0.5 g of nickel / Al2O3 was added to 100 g of the aqueous extraction layer, and a hydrogen gas pressure of 10 MPa was introduced to continue the hydrogenation process at a temperature of 65°C for about 3 hours. After the hydrogenation process, the pressure was released and the reaction was cooled to room temperature.The hydrogenation product (262.3 g) was then distilled on a Claisen head with a condenser at a pressure of 11 hPa and the TCDDM-based composition (56.7 g) was obtained in a boiling range of 170 °C-210 °C. Example 9.

[0081] The non-aqueous solution of the hydroformylation product (174.5 g) and an aqueous extraction solvent containing MPO and water in a weight ratio of 8:2 were mixed in a mass ratio of 1:1 (non-aqueous solution of the hydroformylation product: aqueous extraction solvent) and stirred in a mixer maintained at a temperature of 40 °C. After stirring for 1 hour, the mixture was poured into a glass extractor and allowed to stand for 2 hours to obtain a two-phase mixture. The extraction temperature was maintained at 40 °C. Subsequently, 0.5 g of nickel / Al2O3 was added to 100 g of the aqueous extraction layer, and a hydrogen gas pressure of 3 MPa was introduced to conduct the hydrogenation process at a temperature of 140 °C for approximately 3 hours. After the hydrogenation process, the pressure was released, and the reaction was cooled to room temperature.The hydrogenation product (256.6 g) was then distilled on a Claisen head with a condenser at a pressure of 4 hPa and the TCDDM-based composition (59.2 g) was obtained in a boiling range of 170 °C-210 °C. Comparison example 1

[0082] The non-aqueous solution of the hydroformylation product (174.5 g) from Preparation Example and an aqueous extraction solvent containing propylene glycol and water in a weight ratio of 8:2 (propylene glycol:water) were mixed in a mass ratio of 1:1 (non-aqueous solution of the hydroformylation product: aqueous extraction solvent) and stirred in a mixer maintained at a temperature of 35°C. After stirring for 1 hour, the mixture was poured into a glass extractor and allowed to stand for 2 hours to obtain a two-phase mixture. The extraction temperature was maintained at 35°C. Subsequently, 0.5 g of nickel / Al2O3 was added to 100 g of the aqueous extraction layer, and a hydrogen gas pressure of 2 MPa was introduced to conduct the hydrogenation process at a temperature of 60°C for approximately 3 hours. After the hydrogenation process, the pressure was released and the reaction was cooled to room temperature.The hydrogenation product (245.4 g) was then distilled on a Claisen head with a condenser at a pressure of 4 hPa and the TCDDM-based composition (57.1 g) was obtained in a boiling range of 170 °C-210 °C (“Comparative Example 1”). Comparison example 2

[0083] The non-aqueous solution of the hydroformylation product (174.5 g) from Preparation Example and an aqueous extraction solvent containing methanol and water in a weight ratio of 8:2 (methanol:water) were mixed in a mass ratio of 1:1 (non-aqueous solution of the hydroformylation product: aqueous extraction solvent) and stirred in a mixer maintained at a temperature of 25 °C. After stirring for 1 hour, the mixture was poured into a glass extractor and allowed to stand for 2 hours to form a two-phase mixture. The extraction temperature was maintained at 25 °C. Subsequently, 0.5 g of nickel / Al2O3 was added to 100 g of the aqueous extraction layer, and a hydrogen gas pressure of 6 MPa was introduced to conduct the hydrogenation process at a temperature of 70 °C for approximately 3 hours. After the hydrogenation process, the pressure was released, and the reaction was cooled to room temperature.The hydrogenation product (236.8 g) was then distilled on a Claisen head with a condenser at a pressure of 10 hPa, and the TCDDM-based composition (48.4 g) was obtained in a boiling range of 170 °C-210 °C (“Comparative Example 2”). Comparison example 3

[0084] The non-aqueous solution of the hydroformylation product (174.5 g) from Preparation Example and an aqueous extraction solvent of propylene glycol were mixed in a mass ratio of 1:1 (non-aqueous solution of the hydroformylation product:propylene glycol) and stirred in a mixer maintained at a temperature of 30 °C. After stirring for 1 hour, the mixture was poured into a glass extractor and allowed to stand for 2 hours to obtain a two-phase mixture. The extraction temperature was maintained at 30 °C. Subsequently, 0.5 g of nickel / Al2O3 was added to 100 g of the aqueous extraction layer, and a hydrogen gas pressure of 4 MPa was introduced to conduct the hydrogenation process at a temperature of 100 °C for approximately 3 hours. After the hydrogenation process, the pressure was released, and the reaction was cooled to room temperature.The hydrogenation product (220.0 g) was then distilled on a Claisen head with a condenser at a pressure of 3 hPa and the TCDDM-based composition (41.8 g) was obtained in a boiling range of 170 °C-210 °C (“Comparative Example 3”). Gas chromatography (GC) analysis

[0085] The TCDDM-based compositions were analyzed by gas chromatography (GC). Gas chromatography was performed using the Agilent 6890 system, which includes a BP-5 column (manufactured by SGE Analytical Science) measuring 30 m × 530 µm × 1 µm (length × inner diameter × film thickness) with a liquid phase of 5% phenyl-95% dimethylpolysiloxane and nitrogen as the carrier gas at a flow rate in the following order: 5 mL / min for the first 11 minutes, followed by a stepwise rate increasing from 5 mL / min to 10 mL / min in 1 mL / min increments, and then maintained at 10 mL / min until the end of GC.The sample inlet temperature was 250 °C, the flame ionization detector temperature was 300 °C, the sample injection volume was 2 µL, and the temperature followed this sequence: 50 °C for the first minute, followed by a gradual temperature increase from 50 °C to 180 °C in steps of 15 °C / min and then from 180 °C to 250 °C in steps of 30 °C / min, maintaining the temperature at 250 °C for eight minutes.

[0086] The detailed parameters for GC analysis are listed in Table 1.

[00103] Table 1. Oven Initial temperature: 50 °C (On) Maximum temperature: 300 C° Start time: 1.00 min Equilibration time: 0.20 min Temperature ramps: # rate Final temperature End times 1 15,00 180 0,00 2 30,00 250 8,00 3 0.0 (Off) Final temperature: 50 C° End time: 0.00 min Running time: 20.00 min INJECTOR (SPLIT / SPLITLESS) Mode: Split Initial temperature: 250° C (On) Pressure: 3.46 psi (On) Split ratio: 10:1 Split flow: 50.0 mL / min Total flow: 57.2 mL / min Gas Saver: A Saver flow: 20.0 mL / min Saver time: 2.00 min Gas type: nitrogen COLUMN Capillary column Model number: SGE BP-5 (5% phenyl; 95% dimethyl polysiloxane) Maximum temperature: 300 C° Nominal length: 30.0 m Inner diameter: 530.00 µm Nominal film thickness: 1 µm Mode: ramped flow Initial flow: 5.0 mL / min Start time: 11.00 min # rate Final flow End times 1 1,00 10,0 0,00 2 0.0 (Off) Final flow: 0.0 mL / min Nominal initial pressure: 3.47 psi Average Speed: 37 cm / sec Outlet: Detector Outlet pressure: ambient pressure DETECTOR (FID) Temperature: 300° C (On) Hydrogen flow: 40.0 mL / min (On) Air flow: 450.0 mL / min (On) Mode: Constant Makeup Flow Makeup Gas Flow: 20.0 mL / min(On) Makeup gas type: nitrogen Flame: One Electrometer: One Offset: 2.0 SIGNAL Data rate: 5 Hz Type: Detector Save data: A Zero: 0.0 (Off) Area: 0 Quick tips: Off Damping: 0 PILLAR COMP Derive from the detector Caster Post-run time: 0.00 min

[0087] Fig.Figure 1 shows the GC retention time spectrum of the TCDDM-based composition of Example 4, where bracket 1 refers to the peaks at a retention time between 12.4 minutes and 13 minutes (“Peak 1”), indicating a first component in the composition, bracket 2 refers to the peaks at a retention time between 11.8 minutes and 12.4 minutes (“Peak 2”), indicating a second component in the composition, and peaks labeled “3” refer to the peaks at a retention time of about 10.8 minutes to 11.2 minutes (“Peak 3”), indicating a third component in the composition.

[0088] Further analysis of the GC spectra revealed differences, at least in the amount of the second component, between the examples and the comparative examples. Tables 2 and 3 summarize the relative area under the curve of peak 1 (labeled "1"), peak 2 (labeled "2"), and peak 3 (labeled "3"), and "total" is the sum of the area under all curves during the measurement time (without solvent). Examples 1 to 9 differ from comparative examples 1 to 3 at least with respect to the area under the curve of peak 2 relative to the area under the curve of peak 1, referred to as the "peak 2 / peak 1 value." In particular, examples 1-9 have a peak 2 / peak 1 value in a range between 0.001 and 0.04, while the peak 2 / peak 1 value of comparative examples 1-3 lies outside this range. As shown in Fig.As shown, Comparative Example 2 (right bottle), whose Peak 2 / Peak 1 value was 0.000801, was firmer and more rigid than Example 6 (left bottle) (did not pass flowability testing, which is determined by turning the bottles upside down and waiting for two minutes to see if the compositions are flowable), making them incapable of further mixing or other processing. Table 2. GC result Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 Example8 Example 9 Peak1 / Total 0,9895 0,9934 0,9878 0,9618 0,9723 0,9902 0,9937 0,9975 0,9913 Peak2 / Total 0,00946 0,00642 0,01122 0,0371 0,02704 0,0076 0,0062 0,0012 0,00353 Peak3 / Total 0,00034 0,00015 0,00034 0,0011 0,00032 0,0018 0,0001 0,00032 0,00465 Peak2 / Peak1 0,00956 0,006463 0,011359 0,038574 0,02781 0,007675 0,006239 0,001203 0,003561 Peak 3 / Peak 1 0,000344 0,000151 0,000344 0,001144 0,000329 0,001818 0,000101 0,000321 0,004691 Fluidity passed passed passed passed passed passed passed passed passed Table 3. GC result Comparison example 1 Comparison example 2 Comparison example 3 Peak 1 / Total 0,9554 0,999 0,9436 Peak 2 / Total 0,044 0,0008 0,0461 Peak 3 / Total 0,0006 0,0001 0,00734 Peak 2 / Peak 1 0.046054 0,000801 0,04886 Peak 3 / Peak 1 0,000628 0,0001 0,00778 Fluidity passed failed passed Gas chromatography / mass spectrometry analysis

[0089] The TCDDM-based compositions were further analyzed by gas chromatography / mass spectrometry (GC / MS). GC / MS was performed using an Agilent 6890 GC system and an Agilent 5975 inert MSD (G3171A). The GC section included a BP-1 column (manufactured by SGE Analytical Science) measuring 60 m × 320 µm × 1 µm (length × inner diameter × film thickness), a 100% dimethylpolysiloxane liquid phase, and a helium carrier gas flow rate of 2 mL / min. The sample inlet temperature was 250 °C, and the temperature ramp conditions were as follows: 50 °C for the first two minutes, followed by a gradual temperature increase from 50 °C to 180 °C in increments of 15 °C / min. and then from 180 °C to 250 °C in increments of 30 °C / min, followed by a 6-minute hold at 250 °C. MS analysis then began.The MS part was operated with an electron ionization energy of 70 eV, a source temperature of 230 °C, a quadrupole mass filter temperature of 150 °C, and a scan range of 20 m / z to 230 m / z.

[0090] The detailed parameters for the Ge / mass analysis are listed in Table 4. Table 4. Oven Initial temperature: 50°C (On) Maximum temperature: 280°C Start time: 2.00 min Equilibration time: 0.25 min Temperature ramps: # rate Final temperature End times 1 15,00 180 0,00 2 30,00 250 6,00 3 0.0 (off) Final temperature: 50°C End time: 0.00 min Running time: 19.00 min INJECTOR (SPLIT / SPLITLESS) Mode: Split Initial temperature: 250°C (On) Pressure: 12.81 psi (On) Split ratio: 20:1 Split flow: 40.0 mL / min Total flow: 44.9 mL / min Gas Saver: A Saver Flow: 20.0 Saver time: 2.00 min mL / minGas type: Helium COLUMN Capillary column Model number: SGE BP-1 100% DimethylPolysiloxane Maximum temperature: 325 C° Nominal length: 60.0 m Inner diameter: 320.00 um Nominal film thickness: 1.00 um Mode: constant flow (constantflow) Initial flow rate: 2.0 mL / min Nominal initial pressure: 12.82 psi Average speed: 36cm / sec Outlet: MSD Outlet pressure: vacuum THERMAL AUX Use: MSD Transmission line heating Description: Initial temperature: 280° C (On) Start time: 0.00 min # rate Final temperature End times 1 0.0 (Off) Caster Follow-up time: 0.00 min MS ACQUISITION PARAMETERS R General information MS information Solvent delay: 0.00min EM Absolute: True Resulting EM voltage: 1800.0 Scan parameters Low mass: 20.0 High mass: 230.0 Threshold: 150 MSZones MS Quad: 150 C° Maximum: 200°C MS Source: 230 C° Maximum: 250°C PARAMETER TUNING EMISSION: 34,610 ENERGY: 69,922 REPELLER: 34,814 ION FOCUS: 90,157 INPUT_LE: 9,500 EMVOLT: 1858,824 AMU INCREASE: 1779,000 AMU OFFSET: 119,813 FILAMENT: 1,000 DC POLARITY: 0.000 VENT OPENINGS: 18,573 MASS INCREASE: -625,000 MASS SHIFT: -38,000

[0091] Fig.Figure 2A shows a retention time spectrum in the GC / MS analysis of the TCDDM-based composition of Example 4, where bracket 1' refers to a retention time range between 16.5 minutes and 17.5 minutes ("Peak 1'"), indicating a first component in the composition, bracket 2' refers to a retention time range between 15.0 minutes and 16.5 minutes ("Peak 2'"), indicating a second component in the composition, and peaks labeled "3'" refer to a retention time range from 14.0 minutes to 14.5 minutes ("Peak 3'"), indicating a third component in the composition.

[0092] Fig. Figure 2B shows a detailed part of the spectrum in bracket 2' in Fig. 2A, where the peaks at a retention time of approximately 15.8 minutes to 16.0 minutes are designated as “2-1” (“Peak 2-1”) and the peaks at a retention time of approximately 16.2 minutes to 16.4 minutes are designated as “2-2” (“Peak 2-2”)

[0093] The m / z values ​​for peak 1', peak 2', peak 2-1, peak 2-2 and peak 3' are listed in Table 5. Table 5. m / z Peak 1' 31, 41, 67, 79, 91, 93, 119, 147, 165, 178 Peak 2' 31, 41, 67, 79, 91, 93, 119 Peak 2-1 31, 41, 67, 79, 91, 93, 119, 149, 167 Peak 2-2 31, 41, 67, 79, 91, 93, 119, 149, 167 Peak 3' 31, 41, 67, 79, 91, 135 Polyester from the TCDDM-based composition.

[0094] The TCDDM-based compositions of Examples 1-9 and Comparative Examples 1 and 3 were used to prepare the polyesters of Examples 10-18 and Comparative Examples 4-5, respectively. Specifically, trimellitic acid (TMA) (Tokyo Chemical Industry Co.), the TCDDM-based compositions of Examples 1-9 and Comparative Examples 1 and 3, ethylene glycol (EG) (Oriental Union Chemical Corporation), and purified terephthalic acid (PTA) (China American Petrochemical Co.) were mixed in an autoclave at a molar ratio of 0.5:40:20:50. Thereafter, 100 ppm of titanium butoxide was added and mixed uniformly at a stirring speed of 150 rpm at room temperature. Esterification took place at 4 atm and 220°C. After the amount of water produced by esterification had reached 90% of the theoretical value, the temperature was increased to 250°C and the mixture was placed under vacuum for 30 minutes.Subsequently, the temperature for polycondensation was increased to 280°C. When the inherent viscosity of the composition reached approximately 0.6 to 0.7 dL / g, each mixture was cooled to room temperature and the polyester was collected.

[0095] The polyesters obtained from each of the TCDDM-based compositions were further analyzed for color determination.

[0096] The inherent viscosity was determined according to ASTM D4603. Briefly, approximately 0.25 g of polyester was weighed into a flask and dissolved with approximately 25 mL of solvent (phenol:1,1,2,2-tetrachloroethane = 60:40 (wt%)), and the solution was cooled to approximately room temperature. The solution was then poured into a clean and dry Cannon-Ubbelohde viscometer by passing it through a funnel and filtering it into the top of the larger viscometer tube. The flow time was then recorded. The measurement was repeated at least three times in total, and the results were averaged. The inherent viscosity was determined as follows: ηinh30 °C0.5%=ln ηrC where η inh (unit dL / g) is the inherent viscosity at 30 °C, η rthe relative viscosity = t / t0, where t refers to the average flow time of the solution in seconds and t0 to the average flow time of the solvent in seconds, and C is the concentration of the polymer solution (g / dL).

[0097] The color of the polyester granules was determined according to ASTM D6290 using the NIPPON Denshoku NE 4000 colorimeter with a light source of D65 / 10 (standard illuminant D65) and expressed as the CIELAB color space (defined by the International Commission on Illumination) L*, a* and b*.

[0098] Tables 6 and 7 summarize the CIELAB color space of polyesters obtained from the TCDDM-based compositions of Examples 1-9 and Comparative Examples 1 and 3 in combination with EG, PTA, and TMA. In the CIELAB color space, the b* scale indicates yellowing. Polyesters derived from the TCDDM-based compositions of Examples 1-9 exhibit improved yellowing resistance compared to those from the Comparative Examples. Therefore, the TCDDM-based compositions are considered suitable for use in the claimed application as raw materials for the production of downstream products with improved optical properties. Table 6. polyester TCDDM-based composition source L* a* b* Example 10 Example 1 64,25 -0,9 4,73 Example 11 Example 2 64,91 -0,61 3,95 Example 12 Example 3 64,77 -0,14 5,43 Example 13 Example 4 70,06 -0,13 7,49 Example 14 Example 5 62,63 0,37 6,73 Example 15 Example 6 66,35 -0,26 6,48 Example 16 Example 7 65,33 -0,22 4,05 Example 17 Example 8 68,38 -0,89 5,48 Example 18 Example 9 62,41 1,02 6,12 Table 7. polyester TCDDM-based composition source L* a* b* Comparison example 4 Comparison example 1 63,65 0,11 8,64 Comparison example 5 Comparison example 3 65,94 -0,53 10,34

[0099] The various methods and techniques described above offer a number of possibilities for practicing the application. It should be understood that not all of the described objectives or advantages can necessarily be achieved in accordance with a particular embodiment described herein. For example, those skilled in the art will recognize that the methods can be performed in a manner that achieves or optimizes one advantage or group of advantages taught herein without necessarily achieving other objectives or advantages as taught or suggested herein. A variety of alternatives are mentioned herein.It is to be understood that some embodiments expressly include one, another, or more features, while others expressly exclude one, another, or more features, while still others mitigate a particular feature by including one, another, or more advantageous features.

[0100] Furthermore, one skilled in the art will recognize the applicability of various features from different embodiments. Likewise, the various elements, features, and steps discussed above, as well as other known equivalents for each of these elements, features, or steps, may be employed in various combinations by one skilled in the art to perform processes consistent with the principles described herein. Among the various elements, features, and steps, some are specifically included and others are specifically excluded in various embodiments.

[0101] Although the application has been disclosed in connection with particular embodiments and examples, it will be understood by those skilled in the art that embodiments of the application include other alternative embodiments and / or uses, as well as modifications and equivalents thereof, beyond the specifically disclosed embodiments.

[0102] Various embodiments of this application are described herein, including the best mode known to the inventors for carrying out the application. Variations of these embodiments will become apparent to those skilled in the art upon reading the foregoing description. It is believed that those skilled in the art can appropriately employ such variations and that the application may be practiced otherwise than as specifically described herein. Accordingly, many embodiments of this application include all modifications and equivalents of the subject matter recited in the appended claims, to the extent permitted by applicable law. Furthermore, any combination of the elements described above in all possible variations thereof is encompassed by the application unless otherwise stated herein or clearly contradicted by context.

[0103] All patents and other publications cited in the specification and examples are expressly incorporated herein by reference for all purposes, except for prosecutions connected with them, those which are inconsistent or conflicting with the present document, or those which may have a limiting effect on the broadest scope of the claims now or hereafter attached to the present document. For example, to the extent there is any inconsistency or conflict between the description, definition, and / or use of a term in any of the incorporated materials and the present document, the description, definition, and / or use of the term in the present document shall control. These patents and other publications are provided solely for their disclosure prior to the filing date of the present application.Nothing in this regard should be construed as an admission that the inventors are not entitled to supersede this disclosure by virtue of a prior invention or otherwise. Any references to the dates or contents of these documents are based on information available to the applicants and do not constitute a concession to the accuracy of the dates or contents of these documents.

[0104] Various embodiments of the present application are described above in the detailed description. While these descriptions directly describe the above-noted embodiments, it is understood that those skilled in the art may devise modifications and / or variations to the specific embodiments shown and described herein. All such modifications or variations that fall within the scope of this description are also intended to be included therein. Unless expressly stated, it is the intention of the inventors that the words and phrases in the description and claims have the ordinary and customary meaning to one skilled in the art to which they pertain.

[0105] The foregoing description of various embodiments of the present application known to the applicant at the time of filing the application is presented for purposes of illustration and description. This description is not exhaustive or to limit the invention to the precise form disclosed, and many modifications and variations are possible in light of the above teachings. The described embodiments serve to explain the principles of the present application and their practical application, and to enable others skilled in the art to utilize the present application in various embodiments and with various modifications as are suited to the particular application. It is therefore not intended to limit the invention to the particular embodiments disclosed for practicing the invention.

[0106] Although specific embodiments have been illustrated and described in detail herein, it will be apparent to those skilled in the art that various modifications, additions, substitutions, and the like may be made without departing from the spirit of the invention, and these are therefore considered to be within the scope of the invention as defined in the following claims. Unless already stated, it will be understood by those skilled in the art that each of the various embodiments described and illustrated herein may be further modified to incorporate features of other embodiments disclosed herein. QUOTES CONTAINED IN THE DESCRIPTION

[0000] This list of documents submitted by the applicant was generated automatically and is included solely for the convenience of the reader. This list is not part of the German patent or utility model application. The DPMA assumes no liability for any errors or omissions. Cited patent literature

[0000] US 6,365,782

[0068] Cited non-patent literature

[0000] Standard ASTM D4603

[0096]

Claims

[1] Composition comprising: a first component, which is tricyclodecanedimethanol, and a second component, wherein, when the composition is characterized in gas chromatography, the tricyclodecanedimethanol is eluted at a retention time in the range of 12.4 minutes to 13 minutes, the second component is eluted at a retention time in the range of 11.8 minutes to 12.4 minutes, each indicated by elution peaks at corresponding retention times in a spectrum, and the ratio of the area of ​​the elution peaks indicating the second component compared to the area of ​​the elution peaks indicating the tricyclodecanedimethanol is between 0.001:1 and 0.04:

1. [2] The composition according to claim 1, wherein the composition is loaded in gas chromatography onto a BP-5 capillary column having a length of 30 meters, an inner diameter of 530 µm and a film thickness of 1 µm, characterized by a liquid phase of 5% phenyl and 95% dimethylpolysiloxane and a carrier gas of nitrogen, which is flowed through at a flow rate of 5 mL / min for an initial period of 11 minutes, followed by a stepwise flow rate of 5 mL / min to 10 mL / min with a rate increment of 1 mL / min, under a step temperature in a sequence of 50 °C for 1 minute, then temperature increase from 50 °C to 180 °C in a step of 15 °C / min, then temperature increase from 180 °C to 250 °C in a step of 30 °C / min, followed by 250 °C for 8 minutes, wherein an inlet temperature is 250 °C, a sample injection volume of the composition is 2 µL, and a detector is a flame ionization detector operating at 300 °C. [3] The composition of claim 1, wherein the second component, when characterized in a gas chromatography-mass spectrometry (GC / MS), has a retention time in the range of 15.0 minutes to 16.5 minutes and a fragmentation pattern comprising one or more peaks at a mass-to-charge ratio (m / z) selected from the group consisting of 31, 41, 67, 79, 91, 93, 119, 149, and 167. [4] The composition of claim 3, wherein the fragmentation pattern of the second component comprises peaks at m / z of 31, 41, 67, 79, 91, 93 and 119. [5] The composition of claim 3, wherein the fragmentation pattern of the second component comprises peaks at m / z of 149 and 167 at the retention time in the range of 15.8 minutes to 16.0 minutes, and / or the fragmentation pattern of the second component comprises peaks at m / z of 149 and 167 at the retention time in the range of 16.2 minutes to 16.4 minutes. [6] The composition according to claim 3, wherein in the GC / MS, the composition is loaded onto a BP-1 capillary column with a length of 60 meters, an inner diameter of 320 µm and a film thickness of 1 µm with a liquid phase of 100% dimethylpolysiloxane and a helium carrier gas, flowing at 2 ml / min at an inlet temperature of 250 °C and operated at a step temperature in a sequence of 50 °C for 2 minutes, then temperature increase from 50 °C to 180 °C in steps of 15 °C / min, then temperature increase from 180 °C to 250 °C in steps of 30 °C / min, followed by 250 °C for 6 minutes, and operated with an electron energy of 70 eV, an electron source temperature of 230 °C, a quadrupole mass filter temperature of 150 °C and a mass scan in a range between 20.0 m / z and 230.0 m / z with a solvent delay of 0 minutes. [7] The composition of claim 3, wherein the tricyclodecanedimethanol has a retention time in the range of 16.5 minutes to 17.5 minutes in GC / MS. [8] Composition according to claim 1, characterized by that in gas chromatography it further comprises a third component which is eluted at a retention time in the range from 10.8 minutes to 11.2 minutes and is indicated by an elution peak at the corresponding retention time in the spectrum, and that the ratio of the area of ​​the elution peak indicating the third component compared to the area of ​​the elution peaks indicating the tricyclodecanedimethanol is between 0.00005:1 and 0.005:

1. [9] A composition according to claim 8, wherein the third component is a compound of formula (X):. [10] The composition according to claim 1, wherein the area of ​​the elution peaks indicating tricyclodecanedimethanol is in a ratio of 0.95:1 or greater to the total area of ​​the elution peaks of the composition excluding the solvents. [11] A composition according to claim 1, wherein the second component is one or a mixture of compounds of formula (XI):wherein, X1 = C; X2 = C; i = 1 or 0; j = 1 or 0; v = 1 or 0; and if i = 1, then j = v = 0, R B1 , R B2 , R C1 , R C2 , R D1 and R G1 are not available, (X3-R A ) is a linear or branched C4-alkyl alcohol, X4 is CH2 or CH(CH2OH), and if X4 = CH2, then one of R D2 , R E1 , R E2 , R F1 ,R F2 and R G2is CH2OH, while the other five of R D2 , R E1 , R E2 , R F1 , R F2 and R G2 = H; if X4 = CH(CH2OH), then R D2 , R E1 , R E2 , R F1 , R F2 and R G2 are H; if i = 0, then j = v = 1, X3 is CH, X4 is CH, one of R A , R B1 , R B2 , R C1 and R C2 is CH2OH, while the other four of R A , R B1 , R B2 , R C1 and R C2 = H, one of R D1 , R D2 , R E1 , R E2 , R F1 , R F2 , R G1 and R G2 = CH2OH, another of R D1 , R D2 , R E1 , R E2 , R F1 , R F2 , R G1 and R G2 is CH3, while the other six are from RD1 , R D2 , R E1 , R E2 , R F1 , R F2 , R G1 and R G2 = H. [12] Composition according to claim 11, wherein the second component comprises one or more compounds of formulas (XI)-(XX): [13] Polymer derived from at least the composition according to claim 1. [14] A polymer according to claim 13, which is a polyester, an epoxy, an acrylate, a polycarbonate or a polyurethane derived at least from the composition of claim 1; preferably it is a polyester derived at least from the composition of claim 1. [15] An optical material containing the polymer according to claim 13.

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