Color-forming compounds and UV-absorbing compositions

Abstract

UV-absorbing color-forming compounds and compositions containing the compounds are provided. One or more of the compounds can be incorporated into cosmetic compositions, such as sunscreens, hair care products, and other personal care products, as well as skin care products. The compounds can also be incorporated into compositions such as paints, resins, and dyes to protect surfaces from damage caused by UV exposure. The present disclosure contains constrained pentadienoate structures to minimize or eliminate their photochemical reactivity, and exhibits a λ range of 300 to 370 nm for effective absorption of UV-A and UV-B rays. max The present invention provides a color-forming compound having the formula:

Description

[Technical Field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims the benefit of U.S. Provisional Patent Application No. 63 / 435,372, filed December 27, 2022, which is incorporated herein by reference in its entirety.

[0002] The field of this disclosure relates to color-forming compounds that absorb ultraviolet (UV) light, compositions thereof, and methods of their use. [Background technology]

[0003] Prolonged exposure to UV radiation, such as from the sun, can lead to the formation of minor skin disorders and erythema, increase the risk of skin cancers such as melanoma, and accelerate skin aging, including loss of skin elasticity and wrinkles. Light with wavelengths in both the UV-A range (approximately 320–400 nm) and the UV-B range (approximately 280–320 nm) can cause such skin damage. Therefore, sunscreen compositions should contain absorbers / reflectors for both UV-A and UV-B. Sunscreen compositions often contain one or more organic and / or inorganic compounds to absorb a broad spectrum of the sun's UV radiation (UV-A and UV-B) and thereby provide protection from damage. Several compounds and preparations have been developed and are commercially available for this purpose.

[0004] Damage caused by exposure to UV radiation is not limited to human skin and other animals. It causes changes in the texture of hair on both natural and synthetic fabrics, as well as wood products. It also causes discoloration of fabrics and painted products. A common problem associated with many UV-absorbing compounds used to protect against UV radiation, such as 1,3-diketones and cinnamic acid derivatives, is that they undergo photodegradation over time with exposure, resulting in a decrease in UV absorbance, especially UV-A absorbance.

[0005] Pentadienoates absorb in the UV / Vis spectrum in the 280-400 nm range, making them ideal for use in protecting against damage caused by exposure to sunlight. However, they are photosensitive and photoisomerizable, so light exposure leads to several products, including cyclization and dimerization, with loss of the chromophore and reduced effectiveness in protecting against UV irradiation. To overcome this problem, U.S. Pat. No. 4,847,073 (incorporated herein by reference in its entirety) discloses a compound having the structure: [ka] (wherein X and Y are independently selected from CN, COOR6, -PhNH(R6), CON(R6)2, -Ph-COOR6, and -PhCOR6, and only X or Y may be substituted with H; R1, R2, R3, R4, and R5 are selected from the group consisting of H, OH, COOR6, and alkyl, alkoxy, or hydroxyalkyl groups having 1 to 5 carbon atoms; and R6 is selected from H and alkyl, alkylaryl, or arylalkyl groups having 1 to 22 carbon atoms.) However, the patent does not disclose any compounds having aromatic or heteroaromatic R4.

[0006] US 4,891,212 (incorporated herein by reference in its entirety) discloses a constrained structure containing a pentadienoate chromophore: [ka] (wherein R1, R2, R3, R4, and R5 are selected from H or an alkyl group of 1 to 5 carbon atoms; X is O or NH; and R6 is selected from a divalent alkylene group of 2 to 16 carbon atoms, a cycloalkylene group of 5 to 8 carbon atoms, an arylene group of 6 to 12 carbon atoms, or an alkylarylene group of 7 to 13 carbon atoms), and a sunscreen composition thereof.

[0007] US 10,836,777 (incorporated herein by reference in its entirety) describes an acid or base catalyzed cyclization: [ka] (Wherein R1, R2, R3, R4, and R5 are H, C1-C 10 Alkyl, C6-C 12 aryl, or heteroaryl containing 1 or 2 atoms selected from N, O, and sulfur; X and X are independently nitrile or COR; R is, among others, C-C 10 Alkyl, C1-C 10 The present invention is directed to a synthetic method for preparing herbicides, including the synthesis of 2-(cyclohexenylidene)malonic acid derivatives by the addition of 2-(cyclohexenylidene)malonic acid derivatives, wherein the 2-(cyclohexenylidene)malonic acid derivatives are alkoxy groups.

[0008] Curti et al. [Synlett (2018), 29, 266-281] (incorporated herein by reference in its entirety) developed a specific method for the synthesis of compounds containing (3-phenyl-2-cyclohexen-1-ylidene)propanedinitrile. Staub et al. [J. Mat. Chem. (2003) 13, 825-833 (incorporated herein by reference in its entirety) investigated nonlinear polyene chromophores prepared from certain compounds such as [3-(4-aminophenyl)-2-cyclohexen-1-ylidene]propanedinitrile. The compounds disclosed in US 4,847,073 and US 4,891,212 have a λ of 305-306 max which is ineffective at absorbing the full range of UV-A, it is an object of the present disclosure to provide compounds that include a constrained structure containing a pentadienoate chromophore. [Prior art documents] [Patent documents]

[0009] [Patent Document 1] U.S. Patent No. 4,847,073 [Patent Document 2] U.S. Patent No. 4,891,212 [Patent Document 3] U.S. Patent No. 10,836,777 [Non-patent literature]

[0010] [Non-Patent Document 1] Curti et al.[Synlett(2018),29,266-281] [Non-patent document 2] Staub et al.[J.Mat.Chem.(2003)13,825-833 Summary of the Invention [Means for solving the problem]

[0011] The present disclosure contains constrained pentadienoate structures to minimize or eliminate their photochemical reactivity and has a λ range of 300-370 nm for effective absorption of UV-A and UV-B. max The present invention provides a color-forming compound having the formula:

[0012] A first aspect of the present disclosure is a compound having the chemical structure of Formula I and / or II, or a salt thereof: [ka] During the ceremony, R1 and R2 are H, optionally substituted alkyl, optionally substituted alkynyl, optionally substituted aminoalkyl, optionally substituted hydroxyalkyl, optionally substituted alkoxyalkyl, —CN, —C(O)R′, —C(O)OR′, —C(O)NR′R″, —C(O)SR′, —C(S)NR′R″, —NCO, —C(O)—XR y , C(O)-XR z and -NO2, or R1 and R2 together with the carbon atoms to which they are attached form a cyclic moiety of formula III or formula IV; [ka] During the ceremony, X is O or NR'; R 11 and R 12 is independently selected from H and optionally substituted alkyl; R y and R z is H, optionally substituted C 1-15 independently selected from alkyl, optionally substituted hydroxyalkyl, optionally substituted alkoxyalkyl, polyamide, and polyether; R4 is an optionally substituted C6-C 10 aryl, optionally substituted C2-C9 heteroaryl containing 0-4 heteroatoms selected from O, N, and S; Each of R3, R5, R6, R7, R8, R9, and R 10 is H, halogen, optionally substituted C-C 20 Alkyl, optionally substituted C-C 20 Alkenyl, optionally substituted C-C 20 Alkynyl, optionally substituted C3-C8 cycloalkyl, optionally substituted C2-C 20 Cycloalkenyl, optionally substituted C2-C7 heterocycloalkyl, optionally substituted C6-C 10Aryl, optionally substituted C2-C9 heteroaryl, -OR', -C(O)R', -C(O)OR', -C(O)NR'R'', -C(=NR')NR'R'', -C(=NR'')R', -NR'R'', -CN, -N=NR', cyanate, -OCN, -CNO, -NO2, -OC(O)NR'R'', -SR', -S-SR', -S(O) are independently selected from R', -S(O)2R', -S(O)2OR', -S(O)2NR', -C(O)SR', -C(S)SR', -C(S)NR', ​​-B(OH)2, -B(OR')(OR''), PR'3, PR'2, -P(OR')2, -OP(OR')2, -P(O)(OR')2, -OP(O)(OR')2, polyamides, and polyethers; Each R' and R'' is H, optionally substituted C-C 20 Alkyl, optionally substituted C-C 20 Alkenyl, optionally substituted C-C 20 Alkynyl, optionally substituted C-C 20 Cycloalkyl, optionally substituted C-C 20 Cycloalkenyl, optionally substituted C-C 20 Heterocycloalkyl, optionally substituted C-C 10 are independently selected from aryl, optionally substituted C2-C9 heteroaryl, polyamide, and polyether.

[0013] In some embodiments of Formula I and II, the compound has a cis and / or trans structure of Formula V or Formula VI: [ka] or a salt thereof, During the ceremony, X is O or NR'; R1 is H, -CN, alkyl isocyanate, alkyl isothiocyanate, aryl isocyanate, aryl isothiocyanate, and C(O)-XR z is selected from Ry and R z is H, optionally substituted C 1-15 independently selected from alkyl, optionally substituted hydroxyalkyl, optionally substituted alkoxyalkyl, polyamide, and polyether; Each R 13 , R 14 , R 15 , R 16 , and R 17 is H, halogen, optionally substituted C-C 20 Alkyl, optionally substituted C-C 20 Alkenyl, optionally substituted C-C 20 Alkynyl, optionally substituted C3-C8 cycloalkyl, optionally substituted C2-C 20 Cycloalkenyl, optionally substituted C2-C7 heterocycloalkyl, optionally substituted C6-C 10 and independently selected from aryl, optionally substituted C2-C9 heteroaryl, -OR', -C(O)R', -C(O)OR', -C(O)NR'R'', -C(=NR')NR'R'', -C(=NR'')R', -NR'R'', -CN, -N=NR', cyanate, -OCN, -NO2, -OC(O)NR'R'', -SR', -S-SR', -S(O)R', -S(O)R', -S(O)OR', -S(O)NR', ​​-C(O)SR', -C(S)SR', -C(S)NR', ​​-B(OH)2, -B(OR')(OR''), -PR'2, -P(OR')2, -OP(OR')2, -P(O)(OR')2, -OP(O)(OR')2, polyamide, and polyether. Each R' and R'' is H, optionally substituted C-C 20 Alkyl, optionally substituted C-C 20 Alkenyl, optionally substituted C-C 20 Alkynyl, optionally substituted C-C 20 Cycloalkyl, optionally substituted C-C 20 Cycloalkenyl, optionally substituted C-C 20Heterocycloalkyl, optionally substituted C-C 10 are independently selected from aryl, optionally substituted C2-C9 heteroaryl, polyamide, and polyether.

[0014] A second aspect of the present disclosure is a multimeric compound of formula VII or formula VIII: [ka] or a salt thereof, During the ceremony, Each R1 is H, -CN, alkyl isocyanate, alkyl isothiocyanate, aryl isocyanate, aryl isothiocyanate, and C(O)-XR z are independently selected from X is O or NR'; T is an optionally substituted C-C 20 Alkylene, optionally substituted C-C 20 Alkenylene, optionally substituted C-C 20 Alkynylene, optionally substituted C-C 20 Alkoxyalkylene, optionally substituted C-C 20 Cycloalkylene, optionally substituted C-C 20 Cycloalkenylene, and optionally substituted C-C 20 and heterocycloalkylene, wherein one or more skeletal carbon atoms of the linking moiety T are optionally replaced by a divalent group each independently selected from oxygen (—O—), carbonyl (—CO—), optionally substituted alkylamino, optionally substituted cycloalkylene, optionally substituted heterocyclylene, optionally substituted heteroarylene, and optionally substituted arylene; Each R z is H, optionally substituted C 1-15independently selected from alkyl, optionally substituted hydroxyalkyl, optionally substituted alkoxyalkyl, polyamide, and polyether; Each R3, R5, R6, R7, R8, R9, R 10 , R 13 , R 14 , R 15 , R 16 , and R 17 is H, halogen, optionally substituted C-C 20 Alkyl, optionally substituted C-C 20 Alkenyl, optionally substituted C-C 20 Alkynyl, optionally substituted C3-C8 cycloalkyl, optionally substituted C2-C 20 Cycloalkenyl, optionally substituted C2-C7 heterocycloalkyl, optionally substituted C6-C 10 Aryl, optionally substituted C2-C9 heteroaryl, -OR', -C(O)R', -C(O)OR', -C(O)NR'R'', -C(=NR')NR'R'', -C(=NR'')R', -NR'R'', -CN, -N=NR', cyanate, -OCN, -CNO, -NO2, -OC(O)NR'R'', -SR', -S-SR', -S(O) are independently selected from R', -S(O)2R', -S(O)2OR', -S(O)2NR', -C(O)SR', -C(S)SR', -C(S)NR', ​​-B(OH)2, -B(OR')(OR''), PR'3, PR'2, -P(OR')2, -OP(OR')2, -P(O)(OR')2, -OP(O)(OR')2, polyamides, and polyethers; Each R' and R'' is H, optionally substituted C-C 20 Alkyl, optionally substituted C-C 20 Alkenyl, optionally substituted C-C 20 Alkynyl, optionally substituted C-C 20 Cycloalkyl, optionally substituted C-C 20 Cycloalkenyl, optionally substituted C-C 20 Heterocycloalkyl, optionally substituted C-C10 independently selected from aryl, optionally substituted C2-C9 heteroaryl, polyamide, and polyether; n is selected from 2, 3, 4, 5, and 6.

[0015] A third aspect of the present disclosure is an oligomeric or polymeric compound of formula IX or X: [ka] or a salt thereof, During the ceremony, each X is independently O or NR'; L is an optionally substituted C-C 20 Alkylene, optionally substituted C-C 20 Alkenylene, optionally substituted C-C 20 Alkynylene, optionally substituted C-C 20 Alkoxyalkylene, optionally substituted C-C 20 Cycloalkylene, optionally substituted C-C 20 Cycloalkenylene, optionally substituted C-C 20 and heterocycloalkylene, wherein one or more skeletal carbon atoms of L are optionally replaced by a divalent group each independently selected from oxygen (—O—), carbonyl (—CO—), optionally substituted alkylamino, optionally substituted cycloalkylene, optionally substituted heterocyclylene, optionally substituted heteroarylene, optionally substituted arylene, polyamide, and polyether; Each R3, R5, R6, R7, R8, R9, R 10 , R 13 , R 14 , R 15 , R 16 , and R 17 is H, halogen, optionally substituted C-C 20 Alkyl, optionally substituted C-C 20Alkenyl, optionally substituted C-C 20 Alkynyl, optionally substituted C3-C8 cycloalkyl, optionally substituted C2-C 20 Cycloalkenyl, optionally substituted C2-C7 heterocycloalkyl, optionally substituted C6-C 10 Aryl, optionally substituted C2-C9 heteroaryl, -OR', -C(O)R', -C(O)OR', -C(O)NR'R'', -C(=NR')NR'R'', -C(=NR'')R', -NR'R'', -CN, -N=NR', cyanate, -OCN, -NCO, -NO2, -OC(O)NR'R'', -SR', -S-SR', -S(O)R independently selected from -S(O)R, -S(O)OR, -S(O)NR, -C(O)SR, -C(S)SR, -C(S)NR, -B(OH), -B(OR')(OR'', PR, -PR, -P(OR'), -OP(OR'), -P(O)(OR'), -OP(O)(OR'), polyamides, and polyethers; Each R' and R'' is H, optionally substituted C-C 20 Alkyl, optionally substituted C-C 20 Alkenyl, optionally substituted C-C 20 Alkynyl, optionally substituted C-C 20 Cycloalkyl, optionally substituted C-C 20 Cycloalkenyl, optionally substituted C-C 20 Heterocycloalkyl, optionally substituted C-C 10 independently selected from aryl, optionally substituted C2-C9 heteroaryl, polyamide, and polyether; n is at least 2, 3, 4, 5, 10, 20, 100, 150, 300, 500, or 1000 (e.g., n is an average degree of polymerization from 5 to 1000 or from 10 to 100).

[0016] Also provided are UV absorbing compositions comprising one or more compounds of formulas I, II, and / or VX.

[0017] A fourth aspect of the present disclosure is directed to a method of providing UV photoprotection to the skin or hair of a subject, the method comprising applying to the skin or hair of a subject, such as but not limited to humans and other mammals, a composition comprising one or more of the compounds of Formulas I, II, and / or V-X, such as but not limited to compounds E1-E64 of Table 6.

[0018] A fifth aspect of the present disclosure is directed to a composition stabilized against light-induced degradation, the composition comprising an organic material that undergoes light-induced degradation and one or more compounds selected from compounds having the chemical structure of Formula I and / or II, including, but not limited to, compounds E1-E64 in Table 6.

[0019] In some embodiments of the composition, the organic material is a coating, wax, resin, varnish, lacquer, enamel, paint thermoplastic polymer, thermosetting polymer, polyester, protein, polysaccharide, adhesive, or blends thereof.

[0020] In a preferred embodiment, the composition comprises one or more compounds of formula I, II, and / or VX in an amount ranging from 0.01% to 50% by weight of the organic material.

[0021] A sixth aspect of the present disclosure is directed to a method of providing UV photoprotection to a UV photosensitive material, the method comprising applying to the UV photosensitive material a composition containing one or more compounds of formulae I, II, and / or V-X, such as, but not limited to, compounds E1-E64 of Table 6.

[0022] A seventh aspect of the present disclosure is directed to a composition for protecting fabrics from color fading, comprising one or more compounds selected from compounds having chemical structures of Formulas I, II, and / or V-X, such as, but not limited to, compounds E1-E64 in Table 6. [Brief explanation of the drawings]

[0023] [Figure 1]1 shows the UV absorbance spectrum of a mixture of cis- and trans-2-ethylhexyl (3-phenyl-2-cyclopenten-1-ylidene) cyanoacetate (E6). [Figure 2] Figure 1 shows the H-NMR spectrum of a mixture of cis and trans isomers of 2-ethylhexyl (3-phenyl-2-cyclohexen-1-ylidene) cyanoacetate (E5) in DMSO-d6 obtained using a 400 MHz NMR spectrometer. [Figure 3] 1 shows the H-NMR spectrum of a mixture of cis and trans isomers of 2-ethylhexyl (3-phenyl-2-cyclopenten-1-ylidene) cyanoacetate (E6) in DMSO-d6 obtained using a 400 MHz NMR spectrometer. [Figure 4] 1 shows the H-NMR spectrum of a mixture of cis and trans isomers of ethyl [3-(p-methoxyphenyl)-2-cyclohexen-1-ylidene]cyanoacetate (E7) in DMSO-d6 obtained using a 400 MHz NMR spectrometer. [Figure 5] Figure 1 shows the H-NMR spectrum of a mixture of cis and trans isomers of 2-ethylhexyl [3-(p-methoxyphenyl)-2-cyclopenten-1-ylidene]cyanoacetate (E8) in DMSO-d6 obtained using a 400 MHz NMR spectrometer. DETAILED DESCRIPTION OF THE INVENTION

[0024] definition Reference will now be made in detail to certain embodiments of the present disclosure. Some of the embodiments or aspects thereof are illustrated in the drawings. Some aspects of the present disclosure are described herein with reference to exemplary applications for illustration. It should be understood that numerous specific details, relationships, and methods are described to provide a thorough understanding of the features described herein. However, one skilled in the art will readily recognize that the features described herein can be practiced without one or more of the specific details or in other ways. The features described herein are not limited by the order of acts or events illustrated, as some acts may occur in different orders and / or concurrently with other acts or events, unless otherwise indicated. Furthermore, not all illustrated acts or events are required to implement a methodology in accordance with the features described herein.

[0025] Compounds of the present disclosure include those generally described above and are further illustrated by the classes, subclasses, and species disclosed herein. As used herein, the following definitions shall apply unless otherwise indicated. For purposes of this disclosure, chemical elements are defined as defined in the Periodic Table of the Elements, CAS version, Handbook of Chemistry and Physics, 75 th Additionally, general principles of organic chemistry are identified in "Organic Chemistry," Thomas Sorrell, University Science Books, Sausalito: 1999, and "March's Advanced Organic Chemistry," 5 th Ed., Smith, MB and March, J., John Wiley & Sons, New York: 2001, which is incorporated herein by reference in its entirety.

[0026] Abbreviations used herein have their conventional meaning outside the fields of chemistry and biology. The chemical structures and formulas set forth herein are constructed according to the standard rules of chemical valency known in the art of chemistry.

[0027] The terms "aliphatic" or "aliphatic group," as used herein, mean a straight-chain (i.e., unbranched) or branched, substituted or unsubstituted hydrocarbon chain that is fully saturated or contains one or more units of unsaturation, or a monocyclic or bicyclic hydrocarbon that is fully saturated or contains one or more units of unsaturation, but is not aromatic (also referred to herein as "carbocyclyl," "alicyclic," or "cycloalkyl") and has a single point of attachment to the rest of the molecule. Unless otherwise specified, an aliphatic group contains 1-6 aliphatic carbon atoms. In some embodiments, an aliphatic group contains 1-5 aliphatic carbon atoms. In some embodiments, an aliphatic group contains 1-4 aliphatic carbon atoms. In some embodiments, an aliphatic group contains 1-3 aliphatic carbon atoms. In some embodiments, an aliphatic group contains 1-2 aliphatic carbon atoms. In some embodiments, "alicyclic" (or "carbocyclyl" or "cycloalkyl") refers to a monocyclic C3-C7 hydrocarbon that is fully saturated or contains one or more units of unsaturation, but is not aromatic, and has a single point of attachment to the rest of the molecule. Suitable aliphatic groups include, but are not limited to, linear or branched, substituted or unsubstituted alkyl, alkenyl, alkynyl groups, and hybrids thereof, such as (cycloalkyl)alkyl, (cycloalkenyl)alkyl, or (cycloalkyl)alkenyl.

[0028] The term "heteroatom" refers to one or more of oxygen, sulfur, nitrogen, phosphorus, or silicon (including any oxidized form of nitrogen, sulfur, phosphorus, or silicon, the quaternized form of any basic nitrogen, or a substituted nitrogen of a heterocyclic ring, e.g., N (as in 3,4-dihydro-2H-pyrrolyl), NH (as in pyrrolidinyl), or NR + (including N-substituted pyrrolidinyl).

[0029] The term "unsaturated," as used herein, means that a moiety has one or more units of unsaturation.

[0030] The term "alkylene" refers to a divalent alkyl group. An "alkylene chain" is a polymethylene group, i.e., -(CH2) n -, where n is preferably a positive integer of 1 to 6, 1 to 4, 1 to 3, 1 to 2, or 2 to 3. The substituted alkylene chain is a polymethylene group in which one or more methylene hydrogen atoms are replaced with a substituent. Suitable substituents include those described below for substituted aliphatic groups.

[0031] The terminology used herein is for the purpose of describing exemplary embodiments only and is not intended to be limiting. As used herein, the singular forms "a," "an," and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise. Furthermore, to the extent the terms "including," "include," "having," "has," "with," or variations thereof are used in either the detailed description and / or claims, such terms are intended to be inclusive, just like the term "comprising." Unless otherwise indicated, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art. The materials, methods, and examples are illustrative only and are not intended to be limiting.

[0032] As used herein, the term "about" or "approximately" means a range of up to 10%, preferably up to 5%, and more preferably up to 3% of a given value.

[0033] As used herein, the term "substantially" refers to something that can be done to a great extent or degree.

[0034] As used herein, the term "in an amount ranging from X% to Y%" includes all ranges within that range. For example, a compound in an amount ranging from 0.1% to 50% (w / w) includes ranges such as 0.2% to 49% (w / w), 1.0% to 45% (w / w), 5% to 10% (w / w), 3% to 30% (w / w), 15% to 20% (w / w), and 20% to 45% (w / w).

[0035] The terms "heteroaryl" and "heteroar-" refer to groups having 5 to 10 ring atoms, preferably 5, 6, or 9 ring atoms, sharing 6, 10, or 14 pi electrons in a cyclic arrangement, and having 1 to 5 heteroatoms in addition to the carbon atoms. Heteroaryl groups include, but are not limited to, thienyl, furanyl, pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, indolizinyl, purinyl, naphthyridinyl, and pteridinyl. The terms "heteroaryl" and "heteroar-," as used herein, also include groups in which a heteroaromatic ring is fused to one or more aryl, alicyclic, or heterocyclyl rings, where the radical or point of attachment is on the heteroaromatic ring (or in the case of a divalent fused heteroarylene ring system, at least one radical or point of attachment is on the heteroaromatic ring). Non-limiting examples include indolyl, isoindolyl, benzothienyl, benzofuranyl, dibenzofuranyl, indazolyl, benzimidazolyl, benzthiazolyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, 4H-quinolizinyl, carbozolyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, tetrahydroquinolinyl, tetrahydroisoquinolinyl, and pyrido[2,3-b]-1,4-oxazin-3(4H)-one. Heteroaryl groups can be monocyclic or bicyclic. The term "heteroaryl" can be used interchangeably with the terms "heteroaryl ring," "heteroaryl group," or "heteroaromatic," any of which terms include rings that are optionally substituted.

[0036] As used herein, the terms "heterocyclyl," "heterocyclic radical," and "heterocyclic ring" are used interchangeably and refer to a stable 5- to 7-membered monocyclic or 7- to 10-membered bicyclic heterocyclic moiety that is either saturated or partially unsaturated and has, in addition to carbon atoms, one or more, preferably one to four, heteroatoms, as defined above. As an example, in a saturated or partially unsaturated ring having 0-3 heteroatoms selected from oxygen, sulfur, or nitrogen, the nitrogen can be N (as in 3,4-dihydro-2H-pyrrolyl), NH (as in pyrrolidinyl), or + It may be NR (as in N-substituted pyrrolidinyl).

[0037] A heterocyclic ring can be attached to its pendant group at any heteroatom or carbon atom that results in a stable structure, and any of the ring atoms can be optionally substituted. Examples of such saturated or partially unsaturated heterocyclic radicals include, but are not limited to, tetrahydrofuranyl, tetrahydrothiophenyl, pyrrolidinyl, piperidinyl, pyrrolidinyl, tetrahydroquinolinyl, tetrahydroisoquinolinyl, decahydroquinolinyl, oxazolidinyl, piperidinyl, dioxanyl, dioxolanyl, diazepinyl, oxazepinyl, thiazepinyl, morpholinyl, and quinuclidinyl. The terms "heterocyclyl," "heterocyclyl ring," "heterocyclic group," "heterocyclic moiety," and "heterocyclic radical" are used interchangeably herein and also include groups in which the heterocyclyl ring is fused to one or more aryl, heteroaryl, or alicyclic rings, such as indolinyl, 3H-indolyl, chromanyl, phenanthridinyl, or tetrahydroquinolinyl, when the radical or point of attachment is on the heterocyclyl ring. Heterocyclyl groups can be monocyclic or bicyclic. The term "heterocyclylalkyl" refers to an alkyl group substituted by a heterocyclyl, where the alkyl and heterocyclyl portions are independently optionally substituted.

[0038] As used herein, the term "partially unsaturated" refers to a ring moiety that contains at least one double or triple bond. The term "partially unsaturated" is intended to encompass rings with multiple sites of unsaturation, but is not intended to include aryl or heteroaryl moieties, as defined herein.

[0039] As used herein, unless otherwise specified, the suffix "-ene" is used to describe a divalent group. Thus, any of the above terms can be modified with the suffix "-ene" to describe a divalent version of that moiety. For example, a divalent carbocyclyl is "carbocyclylene," a divalent aryl ring is "arylene," a divalent benzene ring is "phenylene," a divalent heterocycle is "heterocyclylene," a divalent heteroaryl ring is "heteroarylene," a divalent alkyl chain is "alkylene," a divalent alkenyl chain is "alkylene," a divalent alkynyl chain is "alkynylene," etc.

[0040] As used herein, the terms "may," "optional," "optionally," or "optionally may" mean that the subsequently described circumstance may or may not occur, and the description is meant to include cases where the circumstance occurs and cases where it does not. For example, the phrase "optionally substituted" means that a non-hydrogen substituent may or may not be present on a given atom, and thus the description includes structures where a non-hydrogen substituent is present and structures where a non-hydrogen substituent is not present.

[0041] When the term "substituted" appears before or after a list of possible substituents, it is intended that the term apply to all members of that group. For example, the phrase "substituted alkyl and aryl" should be interpreted as "substituted alkyl and substituted aryl."

[0042] Further to the disclosure herein, the term "substituted," when used to modify a specified group or radical, can also mean that one or more hydrogen atoms of the specified group or radical are replaced, each independently of the other, with the same or different substituents as defined herein.

[0043] Further to the disclosure herein, in certain embodiments, a substituted group has 1, 2, 3, or 4 substituents, 1, 2, or 3 substituents, 1 or 2 substituents, or 1 substituent.

[0044] Unless otherwise indicated, the nomenclature of substituents not explicitly defined herein is arrived at by naming the terminal portion of the functionality followed by the adjacent functionality toward the point of attachment. For example, the substituent "hydroxyalkyl" refers to the group HO-(alkyl)-.

[0045] "Halo" and "halogen" refer to fluorine, chlorine, bromine, and iodine.

[0046] With respect to any of the groups disclosed herein that contain one or more substituents, it is to be understood that such groups do not include any substitutions or substitution patterns that are sterically infeasible and / or synthetically infeasible. Additionally, the subject compounds include all stereochemical isomers arising from the substitution of these compounds.

[0047] As described herein, compounds of the present disclosure may contain "optionally substituted" moieties, where specified. In general, the term "substituted," whether preceded by the term "optionally," means that one or more hydrogens in the specified moiety are replaced with a suitable substituent. "Substituted" applies to one or more hydrogens that are either explicit or implicit from the structure (e.g., [ka] At least [ka] refers to, [ka] At least [ka] In addition, in polycyclic ring systems, substituents may replace a hydrogen on any individual ring unless otherwise specified (e.g., [ka] At least [ka] (refers to "optionally substituted"). Unless otherwise indicated, an "optionally substituted" group may have a suitable substituent at each substitutable position of the group, and if more than one position in any given structure may be substituted with more than one substituent selected from a specified group, the substituents may be either the same or different at all positions. Combinations of substituents envisioned by the present disclosure are preferably those that result in the formation of stable or chemically feasible compounds. The term "stable," as used herein, refers to compounds that remain substantially unchanged when subjected to conditions that permit their purification, detection, and, in certain embodiments, their recovery, purification, and use for one or more of the purposes disclosed herein.

[0048] Suitable monovalent substituents on a substitutable carbon atom of an "optionally substituted" group are independently halogen; -(CH) 0-4 R°;-(CH2) 0-4 OR°;-O(CH2) 0-4 R°;-O(CH2) 0-4 C(O)OR°;-O(CH2) 0-4 OR°;-(CH2)0-4 CH(OR°)2;-(CH2) 0-4 SR°; R° may be substituted -(CH2) 0-4 Ph; R° may be substituted with -(CH2) 0-4 O(CH2) 0-1 Ph; -CH=CHPh, which may be substituted with R°; -(CH2), which may be substituted with R° 0-4 O(CH2) 0-1 -pyridyl; -NO2; -CN; -N3; ​​-(CH2) 0-4 N(R°)2;-(CH2) 0-4 N(R°)C(O)R°;-N(R°)C(S)R°;-(CH2) 0-4 N(R°)C(O)N(R°)2;-N(R°)C(S)N(R°)2;-(CH2) 0-4 N(R°)C(S)N(R°)2;-(CH2) 0-4 N(R°)C(O)OR°;-N(R°)N(R°)C(O)R°;-N(R°)N(R°)C(O)N(R°)2;-N(R°)N(R°)C(O)OR°;-(CH2) 0-4 C(O)R°;-C(S)R°;-(CH2) 0-4 C(O)OR°;-(CH2) 0-4 C(O)SR°;-(CH2) 0-4 C(O)OSi(R°)3;-(CH2) 0-4 OC(O)R°;-OC(O)(CH2) 0-4 SR°;-SC(S)SR°;-(CH2) 0-4 SC(O)R°;-(CH2) 0-4 C(O)N(R°)2;-C(S)N(R°)2;-C(S)SR°;-SC(S)SR°;-(CH2) 0-4 OC(O)N(R°)2;-C(O)N(OR°)R°;-C(O)C(O)R°;-C(O)CH2C(O)R°;-C(NOR°)R°;-(CH2) 0-4 SSR°;-(CH2) 0-4 S(O)2R°;-(CH2) 0-4 S(O)2OR°;-(CH2) 0-4 OS(O)2R°;-S(O)2NR°;-(CH2) 0-4S(O)R°;-N(R°)S(O)2N(R°)2;-N(R°)S(O)2R°;-N(OR°)R°;-C(NH)N(R°)2;-P(OR°)2;-P(O)(R°)2;-OP(O)(R°)2;-OP(O)(OR°)2;-SiR°3;-(C 1-4 Linear or branched alkylene)ON(R°)2; or -(C 1-4 linear or branched alkylene)C(O)ON(R°), where each R° may be optionally substituted as defined below and independently represents hydrogen, C 1-6 Aliphatic, -CH2Ph, -O(CH2) 0-1 Ph, -CH2- (a 5-6 membered heteroaryl ring), or a 5-6 membered saturated, partially unsaturated, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, and sulfur; or, notwithstanding the above definitions, two independent occurrences of R° together with their intervening atom(s) form a 3-12 membered saturated, partially unsaturated, or aryl monocyclic or bicyclic ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, and sulfur, which may be substituted as defined below.

[0049] Suitable monovalent substituents on R° (or the ring formed by taking two independent occurrences of R° together with their intervening atoms) are independently halogen; —(CH) 0-2 R ● ;-(Halo R ● ), -(CH2) 0-2 OH;-(CH2) 0-2 OR ● ;-(CH2) 0-2 CH(OR ● )2;-O(HaloR ● );-CN;-N3;-(CH2) 0-2 C(O)R ● ;-(CH2) 0-2 C(O)OH;-(CH2) 0-2 C(O)OR ● ;-(CH2) 0-2 SR ● ;-(CH2) 0-2 SH;-(CH2) 0-2 NH2;-(CH2)0-2 NHR ● ;-(CH2) 0-2 NR ● 2;-NO2, -SiR ● 3;-OSiR ● 3;-C(O)SR ● ;-(C 1-4 Straight or branched chain alkylene)C(O)OR ● , or -SSR ● and each R ● is unsubstituted or, if preceded by "halo", is substituted only with one or more halogens, and C 1-4 Aliphatic, -CH2Ph, -O(CH2) 0-1 or a 5-6 membered saturated, partially unsaturated, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, and sulfur. Suitable divalent substituents on a saturated carbon atom of R° include =0 and =S.

[0050] Suitable divalent substituents on a saturated carbon atom of an "optionally substituted" group include: =O; =S; =NNR # 2;=NNHC(O)R # 2;=NNHC(O)OR # 2;=NNHS(O)2R # 2;=NR # ;=NOR # ;-O(C(R # 2)) 2-3 O-; or -S(C(R # 2)) 2-3 S-; in the formula, R # Each independent occurrence of may be hydrogen, C, which may be substituted as defined below. 1-6 Aliphatic or unsubstituted 5-6 membered saturated, partially unsaturated, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, and sulfur. Suitable divalent substituents attached to adjacent substitutable carbons of an "optionally substituted" group include -O(CR # 2) 2-3 O-, wherein R # Each independent occurrence of may be substituted as defined below with hydrogen, C1-6 It is selected from aliphatic or unsubstituted 5-6 membered saturated, partially unsaturated, or aryl rings having 0-4 heteroatoms independently selected from nitrogen, oxygen, and sulfur.

[0051] R # Suitable substituents on the aliphatic group include halogen, -R ● ,-(Halo R ● ), -OH, -OR ● , -O(HaloR ● ), -CN, -C(O)OH, -C(O)OR ● , -NH2, -NHR ● , -NR ● 2, or -NO2, and each R ● is unsubstituted or, if preceded by "halo", is substituted only with one or more halogens, and independently represents C 1-4 Aliphatic, -CH2Ph, -O(CH2) 0-1 Ph, or a 5-6 membered saturated, partially unsaturated, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, and sulfur.

[0052] Suitable substituents on a substitutable nitrogen of an "optionally substituted" group include -R † , -NR † 2. -C(O)R † , -C(O)OR † , -C(O)C(O)R † , -C(O)CHC(O)R † , -S(O)2R † , -S(O)NR † 2. -C(S)NR † 2. -C(NH)NR † 2, or -N(R † )S(O)2R † 2 are listed, and each R †are independently hydrogen, C1-6 aliphatic which may be substituted as defined below, unsubstituted -OPh, or an unsubstituted 5-6 membered saturated, partially unsaturated, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, and sulfur, or two independent occurrences or, notwithstanding the above definitions, † together with their intervening atom(s), form an unsubstituted 3-12 membered saturated, partially unsaturated, or monocyclic or bicyclic ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, and sulfur.

[0053] R † Suitable substituents on the aliphatic groups are independently halogen, -R ● ,-(Halo R ● ), -OH, -OR ● , -O(HaloR ● ), -CN, -C(O)OH, -C(O)OR ● , -NH2, -NHR ● , -NR ● 2, or -NO2, and each R ● is unsubstituted or, if preceded by "halo", is substituted only with one or more halogens, and independently represents C 1-4 Aliphatic, -CH2Ph, -O(CH2) 0-1 Ph, or a 5-6 membered saturated, partially unsaturated, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, and sulfur.

[0054] As used herein, the term "compound" refers to either cis or trans isomers, or mixtures thereof, unless otherwise specified. References to compounds containing ionizable groups, such as, but not limited to, carboxyl, sulfonic, or amino groups, include both the acidic and basic forms of the compound, i.e., with any counterion, unless otherwise specified. For example, the counterion of a negatively charged acidic group can be any positively charged ion, such as, but not limited to, an alkali metal ion or alkaline earth ion, such as lithium, sodium, potassium, zinc, or calcium; an ammonium ion or alkylammonium ion, such as, but not limited to, methylammonium, dimethylammonium, trimethylammonium, or tetramethylammonium; or an arylammonium ion, such as, but not limited to, phenylammonium, N-methyl-N-phenylammonium, or the like. Similarly, for basic groups, the counterion can be any negatively charged ion, such as, but not limited to, acetate, oxalate, tartrate, propionate, hexanoate, fluoride, chloride, bromide, iodide, sulfate, nitrate, or the like.

[0055] As used herein, the term "pharmaceutically acceptable salt" refers to a salt that, within the scope of sound medical judgment, is suitable for use in contact with the tissues of humans and lower animals without undue toxicity, irritation, allergic reaction, etc., and is commensurate with a reasonable benefit / risk ratio. Pharmaceutically acceptable salts are well known in the art. For example, S.M. Berge et al. provide a detailed description of pharmaceutically acceptable salts in J. Pharmaceutical Sciences, 1977, 66, 1-19, which is incorporated herein by reference.

[0056] In certain embodiments, the neutral forms of the compounds can be regenerated by contacting the salt with a base or acid and isolating the parent compound in the conventional manner. In some embodiments, the parent form of the compound may differ from the various salt forms in certain physical properties, such as solubility in polar solvents.

[0057] Unless otherwise indicated, structures depicted herein are also meant to include all isomeric (e.g., enantiomeric, diastereomeric, and geometric (or conformational)) forms of that structure, e.g., R and S configurations of each asymmetric center, Z and E double bond isomers, and Z and E conformational isomers. Thus, single stereochemical isomers as well as enantiomeric, diastereomeric, and geometric (or conformational) mixtures of the present compounds of the disclosure are encompassed. For example, Squigly bonds within a bonded chemical structure are used to represent unknown stereochemistry and are intended to encompass all possible stereochemical and geometric isomers, e.g., [ka] teeth, [ka] Represents.

[0058] Unless otherwise stated, all tautomeric forms of the compounds of the present disclosure are within the scope of the present disclosure. Additionally, unless otherwise stated, structures depicted herein are also meant to include compounds that differ only in the presence of one or more isotopically enriched atoms. For example, the replacement of a hydrogen with deuterium or tritium, or a carbon with 13 C or 14 Compounds having this structure, including C-enriched carbons, are within the scope of the present invention. Such compounds are useful, for example, as analytical tools, probes for biological assays, or as therapeutic agents according to the present disclosure. In some embodiments, the compounds of the present disclosure are provided as single enantiomers or single diastereomers. A single enantiomer refers to an enantiomeric excess of 80% or greater, such as 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, or 99%.

[0059] The term "oxo," as used herein, means an oxygen that is double bonded to a carbon atom, thereby forming a carbonyl.

[0060] The articles "a" and "an" are used herein to refer to one or to more than one (i.e., to at least one) of the grammatical object of the article. By way of example, "an element" means one element or more than one element.

[0061] A "dosing regimen" (or therapeutic regimen), as that term is used herein, is a series of unit doses (typically two or more) administered individually to a subject, typically separated by periods of time. In some embodiments, a given therapeutic agent has a recommended dosing regimen, which may include one or more doses. In some embodiments, a dosing regimen includes multiple doses, each dose separated from the other by a period of equal length; in some embodiments, a dosing regimen includes multiple doses, with at least two different periods separating the individual doses.

[0062] As understood from the context, a "reference" compound is a compound that is sufficiently similar to a particular compound of interest to allow for a relevant comparison. In some embodiments, information about the reference compound is obtained simultaneously with information about the particular compound. In some embodiments, comparison of the particular compound of interest to the reference compound establishes identity, similarity, or dissimilarity of the particular compound of interest to the compound.

[0063] As used herein, the phrase "therapeutic agent" refers to any agent that has a therapeutic effect and / or induces a desired biological and / or pharmacological effect when administered to a subject.

[0064] As used herein, the term "therapeutically effective amount" refers to an amount of a therapeutic agent that confers a therapeutic effect on a treated subject at a reasonable benefit / risk ratio applicable to any medical treatment. The therapeutic effect can be objective (i.e., measurable by some test or marker) or subjective (i.e., the subject gives an indication of or feels an effect). In particular, a "therapeutically effective amount" refers to an amount of a therapeutic agent that is effective to treat, ameliorate, or prevent a desired disease or condition, or that exhibits a detectable therapeutic or prophylactic effect, such as by improving symptoms associated with the disease, preventing or delaying the onset of the disease or condition, and / or reducing the severity or frequency of symptoms of the disease or condition. A therapeutically effective amount can typically be administered in a dosing regimen that may include multiple doses. For any particular therapeutic agent, the therapeutically effective amount (and / or an appropriate unit dose within an effective dosing regimen) can vary depending, for example, on the route of administration and combination with other drugs. In addition, the specific therapeutically effective amount (and / or unit dose) for any particular subject will depend on a variety of factors, including the disorder being treated and the severity of the disorder; the activity of the specific agent used; the specific composition used; the age, weight, general health, sex, and diet of the subject; the time of administration, route of administration, and / or excretion or metabolic rate of the particular therapeutic agent used; the duration of treatment; and similar factors as are well known in the medical arts.

[0065] As used herein, the term "treatment" (also "treat" or "treating") refers to any administration of a substance (e.g., a provided composition) that partially or completely alleviates, improves, relieves, inhibits, delays the onset of, reduces the severity of, and / or reduces the incidence of one or more symptoms, characteristics, and / or causes of a particular disease, disorder, and / or condition. Such treatment may be treatment of a subject who does not exhibit signs of the associated disease, disorder, and / or condition. Alternatively, or additionally, such treatment may be treatment of a subject who exhibits one or more established signs of the associated disease, disorder, and / or condition. In some embodiments, treatment may be treatment of a subject who has been diagnosed with the associated disease, disorder, and / or condition. In some embodiments, treatment may be treatment of a subject who is known to have one or more susceptibility factors that statistically correlate with an increased risk of developing the associated disease, disorder, and / or condition.

[0066] All references disclosed herein are incorporated by reference in their entirety.

[0067] compound Aspects of the present disclosure are directed to compounds and compositions comprising one or more of such compounds or salts thereof capable of absorbing UV-A and / or UV-B radiation.

[0068] The compound can have the chemical structure of Formula I and / or II, or a salt thereof: [ka] During the ceremony, R1 and R2 are H, optionally substituted alkyl, optionally substituted alkynyl, optionally substituted aminoalkyl, optionally substituted hydroxyalkyl, optionally substituted alkoxyalkyl, —CN, —C(O)R′, —C(O)OR′, —C(O)NR′R″, —C(O)SR′, —C(S)NR′R″, —NCO, —C(O)—XRy , C(O)-XR z and -NO2, or R1 and R2 together with the carbon atoms to which they are attached form a cyclic moiety of formula III or formula IV; [ka] During the ceremony, X is O or NR'; R 11 and R 12 is independently selected from H and optionally substituted alkyl; R y and R z is H, optionally substituted C 1-15 independently selected from alkyl, optionally substituted hydroxyalkyl, optionally substituted alkoxyalkyl, polyamide, and polyether; R4 is an optionally substituted C6-C 10 aryl, optionally substituted C2-C9 heteroaryl containing 0-4 heteroatoms selected from O, N, and S; Each of R3, R5, R6, R7, R8, R9, and R 10 is H, halogen, optionally substituted C-C 20 Alkyl, optionally substituted C-C 20 Alkenyl, optionally substituted C-C 20 Alkynyl, optionally substituted C3-C8 cycloalkyl, optionally substituted C2-C 20 Cycloalkenyl, optionally substituted C2-C7 heterocycloalkyl, optionally substituted C6-C 10Aryl, optionally substituted C2-C9 heteroaryl, -OR', -C(O)R', -C(O)OR', -C(O)NR'R'', -C(=NR')NR'R'', -C(=NR'')R', -NR'R'', -CN, -N=NR', cyanate, -OCN, -CNO, -NO2, -OC(O)NR'R'', -SR', -S-SR', -S(O) are independently selected from R', -S(O)2R', -S(O)2OR', -S(O)2NR', -C(O)SR', -C(S)SR', -C(S)NR', ​​-B(OH)2, -B(OR')(OR''), PR'3, PR'2, -P(OR')2, -OP(OR')2, -P(O)(OR')2, -OP(O)(OR')2, polyamides, and polyethers; Each R' and R'' is H, optionally substituted C-C 20 Alkyl, optionally substituted C-C 20 Alkenyl, optionally substituted C-C 20 Alkynyl, optionally substituted C-C 20 Cycloalkyl, optionally substituted C-C 20 Cycloalkenyl, optionally substituted C-C 20 Heterocycloalkyl, optionally substituted C-C 10 are independently selected from aryl, optionally substituted C2-C9 heteroaryl, polyamide, and polyether.

[0069] In some embodiments, the compound has the structure of Formula I:

[0070] In some other embodiments, the compound has the structure of Formula II.

[0071] In a preferred embodiment of the composition, the compound is selected from compounds E1 to E64 of Table 6.

[0072] In some embodiments, R4 is optionally substituted phenyl.

[0073] In some embodiments, at least one of R and R is —C(O)—XR y is.

[0074] In some embodiments, compounds of the present disclosure have the structure of general formula I and / or II: [ka] or a salt thereof, During the ceremony, R1 and R2 are independently H, substituted or unsubstituted C1-C8 alkyl, C1-C8 alkenyl, C1-C8 alkynyl, C1-C8 aminoalkyl, C1-C8 hydroxyalkyl, C1-C8 alkisocyanate, C1-C8 alkylisothiocyanate, CN, C(O)R', C(O)OR', C(O)NR'R'', C(O)SR', C(S)NR'R'', or NO2; R1 and R2 form a cyclic moiety, the cyclic moiety being of Formula III or Formula IV; [ka] During the ceremony, R 11 and R 12 is H or C1-C 15 Alkyl, for example, but not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, sec-amyl, tert-amyl, 2-methylbutyl, 3-methylbutyl, neopentyl, hexyl, 2-ethylhexyl, 2-butyloctyl, and isomers and variants thereof. R4 is a substituted or unsubstituted C6-C 10Aryl, for example, but not limited to, phenyl, biphenyl, naphthyl, benzyl, benzoyl, 2-, 3-, and / or 4-hydroxyphenyl, 2-, 3-, and / or 4-mercaptophenyl, 2-, 3-, and / or 4-aminophenyl, 2-, 3-, or 4-phenylsulfonic acid and salts thereof, 2-, 3-, and / or 4-nitrophenyl, 2-, 3-, and / or 4-halophenyl, for example, fluorophenyl, chlorophenyl, bromophenyl, and iodophenyl, alkoxyphenyl, for example, but not limited to, methoxy, ethoxy, etc., fluorophenyl, chlorophenyl, bromophenyl, and iodophenyl, chloro ... or substituted or unsubstituted C2-C9 heteroaryl containing one or more atoms selected from O, N, and S, such as, but not limited to, pyrrolyl, pyridyl, pyrrolidinyl, pyrrolidonyl, thiophenyl, indolyl, isoindolyl, imidazolyl, thiazolyl, pyrimidyl, triazolyl, triazinyl, etc. The aryl or heteroaryl group may also be mono-, di-, or trisubstituted, such as, but not limited to, di- or trifluorophenyl, di- or triisocyanato, di- or triisothiocyanato, di- or trimethyl, etc. R3, R5, R6, R7, R8, R9, and R 10 are independently H, halogen, or substituted or unsubstituted C-C 20 Alkyl, for example, but not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, sec-amyl, tert-amyl, 2-methylbutyl, 3-methylbutyl, neopentyl, hexyl, 2-ethylhexyl, 2-butyloctyl, or isomers and variants thereof, C-C 20 Alkenyl, for example, but not limited to, vinyl, 2-methylvinyl, butadienyl, isoprenyl, etc., C-C 20Alkynyl, for example, but not limited to, acetenyl, 2-methylacetenyl, etc.; C3-C8 cycloalkyl, for example, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.; C2-C7 heterocycloalkyl, for example, but not limited to, aziridinyl, azetidinyl, pyrrolidinyl, tetrahydrofuranyl, sulfonyl, tetrahydrothiophenyl, etc.; aryl as defined by R4; heteroaryl as defined by R4; OR', C(O)R', C(O)OR'; C(O)NR'R'', R'R''NC=NR', R'C=NR'', NR'R'', CN, N=NR', cyanate, NO2, OC(O)NR'R'', SR', S-SR', S(O)R', S(O)2R', S(O)2OR', S(O)2NR', C(O)SR', C(S)SR', C(S)NR', ​​B(OH)2, B(OR')(OR''), PR'3, PR'2, P(OR')2, OP(OR')2, P(O)(OR')2, OP(O)(OR')2, polyamide, or polyether; Each R' and R'' is independently H, substituted or unsubstituted C-C as defined above. 20 Alkyl, C1-C 20 Alkenyl, C2-C 20 Alkynyl, C2-C 20 Cycloalkyl, C2-C 20 Cycloalkenyl, C2-C 20 Heterocycloalkyl, C6-C 10 It is an aryl, a C2-C9 heteroaryl, a polyamide, or a polyether.

[0075] In some embodiments, each R and R is an optionally substituted C-C aminoalkyl, an optionally substituted C-C 20 Hydroxyalkyl, optionally substituted C-C 20 Alkyl isocyanates and optionally substituted C-C 20 alkyl isothiocyanates.

[0076] In some embodiments, one or more compounds have the formula V cis-, trans-, or a mixture thereof, or a salt thereof: [ka] During the ceremony, R1 is H, CN, alkyl isocyanate, alkyl isothiocyanate, aryl isocyanate, aryl isothiocyanate, or C(O)-XR z and X is O or NR'; R y and R z are independently H, substituted or unsubstituted C-C 15 alkyl groups, for example, but not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, sec-isoamyl, tert-amyl, 2-methylbutyl, 3-methylbutyl, neopentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, hexyl, 2-ethylhexyl, 2-butyloctyl, and the like; hydroxyalkyl groups, for example, but not limited to, 2-hydroxyethyl, 3-hydroxypropyl, and the like; alkoxyalkyl groups, for example, but not limited to, 3-methoxypropyl or 2-ethoxyethyl, and the like; polyamides or polyethers, including peptides; R3, R5, R6, R7, R8, R9, and R 10 is as described herein above for formula I, R 13 , R 14 , R 15 , R 16 , and R 17 are independently H, halogen, substituted or unsubstituted C-C 20 Alkyl, C2-C 20 Alkenyl, C2-C 20 Alkynyl, C3-C8 cycloalkyl, C2-C 20 Cycloalkenyl, C2-C7 heterocycloalkyl, C6-C 10aryl, C2-C9 heteroaryl, OR', C(O)R', C(O)OR', C(O)NR'R'', R'R''NC=NR', R'C=NR'', NR'R'', CN, N=NR', cyanate, NO2, OC(O)NR'R'', SR', S-SR', S(O)R', S(O)2R', S(O)2OR', S(O)2NR', C(O)SR', C(S)SR', C(S)NR', ​​B(OH)2, B(OR')(OR''), PR'3, PR'2, P(OR')2, OP(OR')2, P(O)(OR')2, OP(O)(OR')2, polyamide, or polyether; R' and R'' are independently H, substituted or unsubstituted C-C 20 Alkyl, C1-C 20 Alkenyl, C2-C 20 Alkynyl, C2-C 20 Cycloalkyl, C2-C 20 Cycloalkenyl, C2-C 20 Heterocycloalkyl, C6-C 10 It is an aryl, a C2-C9 heteroaryl, a polyamide, or a polyether.

[0077] In some other embodiments, one or more compounds have the structure of Formula VI, or a salt thereof: [ka] During the ceremony, R1 is H, CN, alkyl isocyanate, alkyl isothiocyanate, aryl isocyanate, aryl isothiocyanate, or C(O)-XR z and X is O or NR'; R y and R z are independently H, substituted or unsubstituted C-C 15alkyl, for example, but not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, 3-methylbutyl, pentyl, neopentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, hexyl, 2-ethylhexyl, 2-butyloctyl, etc.; hydroxyalkyl, for example, but not limited to, 2-hydroxyethyl, 3-hydroxypropyl, etc.; alkoxyalkyl, for example, but not limited to, 3-methoxypropyl or 2-ethoxyethyl, etc.; polyamides or polyethers containing peptides; R3, R5, R6, R7, and R8 are as described herein above for formula II; Each R 13 , R 14 , R 15 , R 16 , and R 17 is H, halogen, substituted or unsubstituted C1-C 20 Alkyl, C2-C 20 Alkenyl, C2-C 20 Alkynyl, C3-C8 cycloalkyl, C2-C 20 Cycloalkenyl, C2-C7 heterocycloalkyl, C6-C 10 independently selected from aryl, C2-C9 heteroaryl, OR', R'OR'', C(O)R', C(O)OR', C(O)NR'R'', R'R''NC=NR', R'C=NR'', NR'R'', CN, N=NR', cyanate, NO2, OC(O)NR'R'', SR', S-SR', S(O)R', S(O)2R', S(O)2OR', S(O)2NR', C(O)SR', C(S)SR', C(S)NR', ​​B(OH)2, B(OR')(OR''), PR'3, PR'2, P(OR')2, OP(OR')2, P(O)(OR')2, OP(O)(OR')2, polyamide, or polyether; R' and R'' are H, substituted or unsubstituted C1-C 20 Alkyl, C1-C 20 Alkenyl, C2-C 20 Alkynyl, C2-C 20 Cycloalkyl, C2-C20 Cycloalkenyl, C2-C 20 Heterocycloalkyl, C6-C 10 are independently selected from aryl, C2-C9 heteroaryl, polyamide, and polyether.

[0078] In some embodiments, R1 and R2 of the compounds of Formula I and II are independently selected from H, substituted or unsubstituted C1-C8 aminoalkyl, C1-C8 hydroxyalkyl, C1-C8 alkylisocyanate, C1-C8 alkylisothiocyanate, COOR', or COSR', and salts thereof, or R1 and R2 form a cyclic moiety, the cyclic moiety being of Formula III or Formula IV, [ka] During the ceremony, R 11 and R 12 are independently H or alkyl; R' and R'' are independently H, substituted or unsubstituted C-C 20 Alkyl, C1-C 20 Alkenyl, C2-C 20 Alkynyl, C2-C 20 Cycloalkyl, C2-C 20 Cycloalkenyl, C2-C 20 Heterocycloalkyl, C6-C 10 It is an aryl, a C2-C9 heteroaryl, a polyamide, or a polyether.

[0079] In some embodiments, the compounds of Formula I and II or salts thereof are multimers, eg, dimers or trimers.

[0080] Embodiments of the present disclosure are directed to cis and / or trans chemical compounds having the structure of Formula V and / or VI, or salts thereof: [ka] During the ceremony, R1 is H, CN, alkyl isocyanate, alkyl isothiocyanate, aryl isocyanate, aryl isothiocyanate, or C(O)-XR z and X is O or NR'; R y and R z are independently H, substituted or unsubstituted C-C 15 Alkyl, C1-C 15 Hydroxyalkyl, C1-C 15 alkoxyalkyl, apolyamide, or a polyether; R 13 , R 14 , R 15 , R 16 , and R 17 are independently H, halogen, substituted or unsubstituted C-C 20 Alkyl, C2-C 20 Alkenyl, C2-C 20 Alkynyl, C3-C8 cycloalkyl, C2-C 20 Cycloalkenyl, C2-C7 heterocycloalkyl, C6-C 10 aryl, C2-C9 heteroaryl, OR', C(O)R', C(O)OR', C(O)NR'R'', R'R''NC=NR', R'C=NR'', NR'R'', CN, N=NR', cyanate, NO2, OC(O)NR'R'', SR', S-SR', S(O)R', S(O)2R', S(O)2OR', S(O)2NR', C(O)SR', C(S)SR', C(S)NR', ​​B(OH)2, B(OR')(OR''), PR'3, PR'2, P(OR')2, OP(OR')2, P(O)(OR')2, OP(O)(OR')2, polyamide, or polyether; R' and R'' are independently H, substituted or unsubstituted C-C 20 Alkyl, C1-C 20 Alkenyl, C2-C 20 Alkynyl, C2-C 20 Cycloalkyl, C2-C 20 Cycloalkenyl, C2-C 20Heterocycloalkyl, C6-C 10 aryl, C2-C9 heteroaryl, polyamide, or polyether; R3, R5, R6, R7, R8, R9, and R 10 is as defined for formula I. R y and R z are independently H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, sec-isoamyl, tert-amyl, 2-methylbutyl, 3-methylbutyl, neopentyl, hexyl, 2-ethylhexyl, 2-butyloctyl, 2-ethoxyethyl, 3-methoxypropyl, polyamide, or polyether; R 13 , R 14 , R 15 , R 16 , and R 17 are independently H, halogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, sec-amyl, tert-amyl, 2-methylbutyl, 3-methylbutyl, neopentyl, hexyl, 2-ethylhexyl, 2-butyloctyl, hydroxy, methoxy, ethoxy, 2-ethoxyethyl, 3-methoxypropyl, amino, methylamino, dimethylamino, trimethylammonium, trifluoromethyl, or NO.

[0081] In some embodiments of Formulas I and II, the compound having a cis and / or trans structure is a compound of Formula V or Formula VI: [ka] or a salt thereof, During the ceremony, R1 is H, -CN, alkyl isocyanate, alkyl isothiocyanate, aryl isocyanate, aryl isothiocyanate, and C(O)-XR z is selected from Each R 13 , R14 , R 15 , R 16 , and R 17 is H, halogen, optionally substituted C-C 20 Alkyl, optionally substituted C-C 20 Alkenyl, optionally substituted C-C 20 Alkynyl, optionally substituted C3-C8 cycloalkyl, optionally substituted C2-C 20 Cycloalkenyl, optionally substituted C2-C7 heterocycloalkyl, optionally substituted C6-C 10 and independently selected from aryl, optionally substituted C2-C9 heteroaryl, -OR', -C(O)R', -C(O)OR', -C(O)NR'R'', -C(=NR')NR'R'', -C(=NR'')R', -NR'R'', -CN, -N=NR', cyanate, -OCN, -NO2, -OC(O)NR'R'', -SR', -S-SR', -S(O)R', -S(O)R', -S(O)OR', -S(O)NR', ​​-C(O)SR', -C(S)SR', -C(S)NR', ​​-B(OH)2, -B(OR')(OR''), -PR'2, -P(OR')2, -OP(OR')2, -P(O)(OR')2, -OP(O)(OR')2, polyamide, and polyether.

[0082] In some embodiments of Formulas V and VI, R 1 is —CN.

[0083] In some embodiments of Formulas V and VI, R is —C(O)—XR z is.

[0084] In some embodiments of Formulas V and VI, R y and R z is an optionally substituted C 1-15 It is alkyl.

[0085] In some embodiments of formulas V and VI, X is O.

[0086] In some embodiments of Formulas V and VI, X is NH.

[0087] In some embodiments of Formulas I, II, V, and VI, Each R y and R z is independently selected from H, methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, pentyl, sec-amyl, tert-amyl, 2-methylbutyl, 3-methylbutyl, neopentyl, hexyl, 2-ethylhexyl, 2-butyloctyl, 2-ethoxyethyl, and 3-methoxypropyl; Each R3, R5, R6, R7, R8, R9, R 10 , R 13 , R 14 , R 15 , R 16 , and R 17 are independently selected from H, halogen, methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, pentyl, sec-amyl, tert-amyl, 2-methylbutyl, 3-methylbutyl, neopentyl, hexyl, 2-ethylhexyl, 2-butyloctyl, hydroxy, methoxy, ethoxy, 2-ethoxyethyl, 3-methoxypropyl, amino, methylamino, dimethylamino, trimethylammonium, trifluoromethyl, and —NO2.

[0088] In some embodiments of Formulas I, II, V, and VI, R y and R z teeth, [ka] are independently selected from

[0089] In some embodiments of Formulas I, II, V, and VI, R4 is [ka] is selected from.

[0090] In some embodiments, the compounds of Formula I and II or salts thereof are in multimeric form.

[0091] An embodiment of the present disclosure is a multimeric compound of formula VII or formula VIII: [ka] or salts thereof, During the ceremony, Each R1 is H, -CN, alkyl isocyanate, alkyl isothiocyanate, aryl isocyanate, aryl isothiocyanate, and C(O)-XR z are independently selected from X is O or NR'; T is an optionally substituted C-C 20 Alkylene, optionally substituted C-C 20 Alkenylene, optionally substituted C-C 20 Alkynylene, optionally substituted C-C 20 Alkoxyalkylene, optionally substituted C-C 20 Cycloalkylene, optionally substituted C-C 20 Cycloalkenylene, and optionally substituted C-C 20 and heterocycloalkylene, wherein one or more skeletal carbon atoms of the linking moiety T are optionally replaced by a divalent group each independently selected from oxygen (—O—), carbonyl (—CO—), optionally substituted alkylamino, optionally substituted cycloalkylene, optionally substituted heterocyclylene, optionally substituted heteroarylene, and optionally substituted arylene; Each R z is H, optionally substituted C 1-15 independently selected from alkyl, optionally substituted hydroxyalkyl, optionally substituted alkoxyalkyl, polyamide, and polyether; Each R3, R5, R6, R7, R8, R9, R 10 , R 13 , R 14 , R 15 , R 16 , and R 17 is H, halogen, optionally substituted C-C 20 Alkyl, optionally substituted C-C 20 Alkenyl, optionally substituted C-C 20 Alkynyl, optionally substituted C3-C8 cycloalkyl, optionally substituted C2-C 20 Cycloalkenyl, optionally substituted C2-C7 heterocycloalkyl, optionally substituted C6-C 10 Aryl, optionally substituted C2-C9 heteroaryl, -OR', -C(O)R', -C(O)OR', -C(O)NR'R'', -C(=NR')NR'R'', -C(=NR'')R', -NR'R'', -CN, -N=NR', cyanate, -OCN, -CNO, -NO2, -OC(O)NR'R'', -SR', -S-SR', -S(O) are independently selected from R', -S(O)2R', -S(O)2OR', -S(O)2NR', -C(O)SR', -C(S)SR', -C(S)NR', ​​-B(OH)2, -B(OR')(OR''), PR'3, PR'2, -P(OR')2, -OP(OR')2, -P(O)(OR')2, -OP(O)(OR')2, polyamides, and polyethers; Each R' and R'' is H, optionally substituted C-C 20 Alkyl, optionally substituted C-C 20 Alkenyl, optionally substituted C-C 20 Alkynyl, optionally substituted C-C 20 Cycloalkyl, optionally substituted C-C 20 Cycloalkenyl, optionally substituted C-C 20 Heterocycloalkyl, optionally substituted C-C 10 independently selected from aryl, optionally substituted C2-C9 heteroaryl, polyamide, and polyether; n is selected from 2, 3, 4, 5, and 6.

[0092] In some embodiments, R1 is -CN.

[0093] In some embodiments, R is —C(O)—XR z is.

[0094] In some embodiments, R z independently represents an optionally substituted C 1-15 It is alkyl.

[0095] In some embodiments, X is O.

[0096] In some embodiments, X is NH.

[0097] In some embodiments, the compound is a compound of formula VII: In some embodiments, the compound is a compound of formula VIII:

[0098] It is to be understood that any of the compound chromophore embodiments of Formula I and II can also be applied to multimeric and polymeric forms of the compounds.

[0099] In some embodiments, the compounds of Formula I and II or their salts are conjugated to an oligomer, such as, but not limited to, an oligopeptide, a polypeptide, a protein, polyethylene glycol (PEG), polypropylene glycol (PPG), a polyamide, a polycarbonate, a polyurethane, a polyurea, a polyester, an oligosaccharide, or a polysaccharide. Examples of polysaccharides include, but are not limited to, chitin, chitosan, cotton, cellulose, hemicellulose, pectin, and the like. In some other embodiments, the compounds or their salts are copolymerized with ethylene oxide, propylene oxide, hydroxy acids, carboxylic acids, amines, isocyanate alcohols / amines, isothiocyanate alcohols / amines, and the like. For example, R1 and R2 can be, but are not limited to, carboxyl, C1-C8 aminoalkyl, such as aminomethyl, 2-aminoethyl, 3-aminopropyl, 4-aminopentyl, 6-aminohexyl, and isomers thereof, C1-C8 hydroxyalkyl, such as hydroxymethyl, 2-hydroxyethyl, 3-hydroxypropyl, 4-hydroxypentyl, 6-hydroxyhexyl, and isomers thereof, C1-C8 alkylisocyanate, such as methylisocyanate, 2-ethylisocyanate, 3-propylisocyanate, 4-pentylisocyanate, 6-hexylisocyanate, and isomers thereof, and C1-C8 alkylisothiocyanate. When the functional groups are selected from polymerizable groups such as thioisocyanates, for example, methylthioisocyanate, 2-ethylthioisocyanate, 3-propylthioisocyanate, 4-pentylthioisocyanate, 6-hexylthioisocyanate, and isomers thereof, they can be copolymerized with compounds such as, but not limited to, ethylene glycol, ethylene oxide, propylene glycol, propylene oxide, C4-C6 polyols, ethylenediamine, propylenediamine, 1,4-butanediamine (putrescine), 1,5-diaminopentane (cadaverine), 1,6-hexanediamine, dithioisocyanates, and diisocyanates derived by methods well known in the art.

[0100] In some embodiments, the oligomer or polymer comprises a chromophore of formula XI or XII: [ka] During the ceremony, Each R3, R5, R6, R7, R8, R9, R 10 , R 13 , R 14 , R 15 , R 16 , and R 17 is H, halogen, substituted or unsubstituted C1-C 20 Alkyl, C2-C 20 Alkenyl, C2-C 20 Alkynyl, C3-C8 cycloalkyl, C2-C 20 Cycloalkenyl, C2-C7 heterocycloalkyl, C6-C 10 independently selected from aryl, C2-C9 heteroaryl, OR', C(O)R', C(O)OR', C(O)NR'R'', R'R''NC=NR', R'C=NR'', NR'R'', CN, N=NR', cyanate, NO2, OC(O)NR'R'', SR', S-SR', S(O)R', S(O)2R', S(O)2OR', S(O)2NR', C(O)SR', C(S)SR', C(S)NR', ​​B(OH)2, B(OR')(OR''), PR'3, PR'2, P(OR')2, OP(OR')2, P(O)(OR')2, OP(O)(OR')2, polyamide, and polyether; R' and R'' are independently H, substituted or unsubstituted C-C 20 Alkyl, C1-C 20 Alkenyl, C2-C 20 Alkynyl, C2-C 20 Cycloalkyl, C2-C 20 Cycloalkenyl, C2-C 20 Heterocycloalkyl, C6-C 10 It is an aryl, a C2-C9 heteroaryl, a polyamide, or a polyether.

[0101] The present disclosure provides oligomers and polymers comprising monomeric repeating units of Formula XI and / or XII linked together using suitable linking chemistry or linking moieties. Exemplary linking moieties are described herein. In some embodiments, the oligomers and polymers are characterized as polyethers, polyesters, polyamides, polycarbonates, polyurethanes, polyureas, or polysaccharides. In some embodiments, the monomeric precursors of the oligomers and polymers of the present disclosure are compounds of Formula I and / or II.

[0102] The present disclosure provides copolymers comprising monomeric repeat units of formula XI and / or XII and one or more additional comonomers of interest and / or end groups or conjugate moieties of interest. The copolymers can be random or block copolymers.

[0103] In some embodiments, the oligomer or polymer has an average length or degree of polymerization ranging from 5 to 5000 repeating units, e.g., from 5 to 1000, from 5 to 500, from 5 to 100, or from 10 to 100. In some embodiments, the length is from 5 to 100, e.g., from 5 to 50, from 10 to 50, from 10 to 40, from 10 to 30, or from 10 to 20 repeating units.

[0104] The amount of chromophore in the oligomer or polymer (e.g., the number of repeating units of the formula) will vary depending on the desired application. In some embodiments, the oligomer or polymer can be a homo-oligomer or homopolymer of a compound of Formula I or II. The oligomer or polymer can be obtained by copolymerizing a compound of Formula I or II, or a salt thereof, with other monomer(s) at different molar ratios, such as, but not limited to, 1:1, 1:10, 1:20, 1:30, 1:50, 1:100, 1:150, 1:200, 1:300, 1:400, 1:500, 1:700, 1:1000, 1:1500, or 1:200.

[0105] In one preferred embodiment, the one or more compounds have structural formula IX: [ka] During the ceremony, X is O or NR'; L is C1-C 20 alkyl, alkenyl, alkyne, alkoxyalkyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, aryl, heteroaryl, polyamide, or polyether; R3, R5, R6, R7, R8, R9, R 10、 R 13 , R 14 , R 15 , R 16 , and R 17 is as defined herein for Formula V; n is at least 2, 3, 4, 5, 10, 20, 100, 150, 300, 500, 1000 or more any number of repeating units.

[0106] In a second preferred embodiment, the one or more compounds have the structure of formula X: [ka] During the ceremony, X is O or NR'; L is a substituted or unsubstituted C1-C 20 alkyl, alkenyl, alkyne, alkoxyalkyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, aryl, heteroaryl, polyamide, or polyether; R3, R5, R6, R7, R8, R 13 , R 14 , R 15 , R 16 , and R 17 is as defined herein for formula VI, n is at least 2, 3, 4, 5, 10, 20, 100, 150, 300, 500, 1000 or more any number of repeating units.

[0107] In some embodiments, the oligomeric or polymeric compound is a compound of formula IX or X: [ka] or a salt thereof, During the ceremony, each X is independently O or NR'; L is an optionally substituted C-C 20 Alkylene, optionally substituted C-C 20 Alkenylene, optionally substituted C-C 20 Alkynylene, optionally substituted C-C 20 Alkoxyalkylene, optionally substituted C-C 20 Cycloalkylene, optionally substituted C-C 20 Cycloalkenylene, optionally substituted C-C 20 and heterocycloalkylene, wherein one or more skeletal carbon atoms of L are optionally replaced by a divalent group each independently selected from oxygen (—O—), carbonyl (—CO—), optionally substituted alkylamino, optionally substituted cycloalkylene, optionally substituted heterocyclylene, optionally substituted heteroarylene, optionally substituted arylene, polyamide, and polyether; Each R3, R5, R6, R7, R8, R9, R 10 , R 13 , R 14 , R 15 , R 16 , and R 17 is H, halogen, optionally substituted C-C 20 Alkyl, optionally substituted C-C 20 Alkenyl, optionally substituted C-C 20 Alkynyl, optionally substituted C3-C8 cycloalkyl, optionally substituted C2-C 20 Cycloalkenyl, optionally substituted C2-C7 heterocycloalkyl, optionally substituted C6-C10 Aryl, optionally substituted C2-C9 heteroaryl, -OR', -C(O)R', -C(O)OR', -C(O)NR'R'', -C(=NR')NR'R'', -C(=NR'')R', -NR'R'', -CN, -N=NR', cyanate, -OCN, -NCO, -NO2, -OC(O)NR'R'', -SR', -S-SR', -S(O)R independently selected from -S(O)R, -S(O)OR, -S(O)NR, -C(O)SR, -C(S)SR, -C(S)NR, -B(OH), -B(OR')(OR'', PR, -PR, -P(OR'), -OP(OR'), -P(O)(OR'), -OP(O)(OR'), polyamides, and polyethers; Each R' and R'' is H, optionally substituted C-C 20 Alkyl, optionally substituted C-C 20 Alkenyl, optionally substituted C-C 20 Alkynyl, optionally substituted C-C 20 Cycloalkyl, optionally substituted C-C 20 Cycloalkenyl, optionally substituted C-C 20 Heterocycloalkyl, optionally substituted C-C 10 independently selected from aryl, optionally substituted C2-C9 heteroaryl, polyamide, and polyether; n is at least 2, 3, 4, 5, 10, 20, 100, 150, 300, 500, or 1000.

[0108] In some embodiments, the oligomer or polymer has a value of n, which represents the average degree of polymerization. In some embodiments, n is in the range of 5 to 5000, e.g., 5 to 1000, 5 to 500, 5 to 100, or 10 to 100. In some embodiments, n is 5 to 50, e.g., 10 to 50, 10 to 40, 10 to 30, or 10 to 20.

[0109] In some embodiments, the compound is a homo-oligomer or homo-polymer, hi some embodiments, the compound is an oligomer or polymer that is a polyether, polyester, polyamide, polycarbonate, polyurethane, polyurea, or polysaccharide.

[0110] In some embodiments, the one or more compounds capable of absorbing UV-A and / or UV-B radiation are selected from the compounds listed in Table 6.

[0111] Generally, the compounds of the present disclosure have an absorption maximum (λ) in the range of 270 to 400 nm, preferably 280 to 390 nm, preferably 290 to 380 nm, more preferably 295 to 375 nm, even more preferably 300 to 375 nm, and most preferably 315 to 375 nm. max ), and λ max at least 10,000, preferably at least 12,000, preferably at least 14,000, preferably at least 16,000, more preferably at least 18,000, and most preferably at least 20,000 M -1 cm -1 In some formulations of the composition, the ability of the UV absorbing compound is measured by the mass absorption coefficient (i.e., λ over a one centimeter optical path length). max (absorption at a concentration of 1 gram per deciliter) as used herein and subsequently E 1% Thus, suitable compounds for use in the composition have a viscosity of at least 400, preferably at least 500, more preferably at least 600, more preferably at least 700, even more preferably at least 800, and most preferably at least 900 dL g -1 ·cm -1 E 1% It has. Cosmetic composition:

[0112] composition The present disclosure provides UV absorbing compositions that include one or more compounds of formulae I, II, and / or VX (eg, as described above).

[0113] In some embodiments of the composition, one or more compounds have the structure of Formula I:

[0114] In some other embodiments of the compositions, one or more compounds have the structure of Formula II.

[0115] In yet another embodiment of the composition, the two or more compounds have the structures of Formula I and Formula II.

[0116] In a preferred embodiment of the composition, the one or more compounds are selected from compounds E1 to E64 of Table 6.

[0117] In another preferred embodiment, the one or more compounds have the cis- and / or trans structure of Formula V, or a salt thereof: [ka] During the ceremony, R1 is H, CN, alkyl isocyanate, alkyl isothiocyanate, aryl isocyanate, aryl isothiocyanate, or C(O)-XR z and X is O or NR'; H, substituted or unsubstituted C1-C 15 Alkyl, C1-C 15 Hydroxyalkyl, C1-C 15 each R independently selected from alkoxyalkyl, polyamide, and polyether; y and R z , Each R 13 , R 14 , R 15 , R 16 , and R 17 is H, halogen, substituted or unsubstituted C1-C 20 Alkyl, C2-C 20 Alkenyl, C2-C 20 Alkynyl, C3-C8 cycloalkyl, C2-C 20Cycloalkenyl, C2-C7 heterocycloalkyl, C6-C 10 Aryl, C2-C9 heteroaryl, OR', C(O)R', C(O)OR', C(O)NR'R'', R'R''NC=NR', R'C=NR'', NR'R'', CN, N=NR', cyanate, NO2, OC(O)NR'R'', SR', S-SR', S(O)R', S(O)2R', S(O)2OR', S(O)2NR', C(O)SR', C(S)SR', C(S)NR', ​​B(OH)2, B(OR')(OR''), PR'3, PR'2, P(OR')2, OP(OR')2, P(O)(OR')2, OP(O)(OR') 2 , polyamide, and polyether; Each R' and R'' is H, substituted or unsubstituted C1-C 20 Alkyl, C1-C 20 Alkenyl, C2-C 20 Alkynyl, C2-C 20 Cycloalkyl, C2-C 20 Cycloalkenyl, C2-C 20 Heterocycloalkyl, C6-C 10 independently selected from aryl, C2-C9 heteroaryl, polyamide, and polyether; R3, R5, R6, R7, R8, R9, and R 10 is as defined for formula I.

[0118] In some embodiments of the composition, R y and R z are independently H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, sec-isoamyl, tert-amyl, 2-methylbutyl, 3-methylbutyl, neopentyl, hexyl, 2-ethylhexyl, 2-butyloctyl, 2-ethoxyethyl, 3-methoxypropyl, polyamide, or polyether; R 13 , R 14 , R 15 , R 16 , and R 17are independently H, halogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, sec-amyl, tert-amyl, 2-methylbutyl, 3-methylbutyl, neopentyl, hexyl, 2-ethylhexyl, 2-butyloctyl, hydroxy, methoxy, ethoxy, 2-ethoxyethyl, 3-methoxypropyl, amino, methylamino, dimethylamino, trimethylammonium, trifluoromethyl, or NO.

[0119] In another preferred embodiment, one or more compounds have the cis- and / or trans structure of Formula VI, or a salt thereof: [ka] During the ceremony, R1 is H, CN, alkyl isocyanate, alkyl isothiocyanate, aryl isocyanate, aryl isothiocyanate, or C(O)-XR z and X is O or NR'; Each R y and R z is H, substituted or unsubstituted C1-C 15 Alkyl, C1-C 15 Hydroxyalkyl, C1-C 15 independently selected from alkoxyalkyl, polyamide, and polyether; Each R 13 , R 14 , R 15 , R 16 , and R 17 is H, halogen, substituted or unsubstituted C1-C 20 Alkyl, C2-C 20 Alkenyl, C2-C 20 Alkynyl, C3-C8 cycloalkyl, C2-C 20 Cycloalkenyl, C2-C7 heterocycloalkyl, C6-C 10independently selected from aryl, C2-C9 heteroaryl, OR', C(O)R', C(O)OR', C(O)NR'R'', R'R''NC=NR', R'C=NR'', NR'R'', CN, N=NR', cyanate, NO2, OC(O)NR'R'', SR', S-SR', S(O)R', S(O)2R', S(O)2OR', S(O)2NR', C(O)SR', C(S)SR', C(S)NR', ​​B(OH)2, B(OR')(OR''), PR'3, PR'2, P(OR')2, OP(OR')2, P(O)(OR')2, OP(O)(OR')2, polyamide, and polyether; Each R' and R'' is H, substituted or unsubstituted C1-C 20 Alkyl, C1-C 20 Alkenyl, C2-C 20 Alkynyl, C2-C 20 Cycloalkyl, C2-C 20 Cycloalkenyl, C2-C 20 Heterocycloalkyl, C6-C 10 independently selected from aryl, C2-C9 heteroaryl, polyamide, and polyether; R3, R5, R6, R7, and R8 are as defined for formula II.

[0120] In some embodiments of the composition, R y and R z are independently H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, sec-isoamyl, tert-amyl, 2-methylbutyl, 3-methylbutyl, neopentyl, hexyl, 2-ethylhexyl, 2-butyloctyl, 2-ethoxyethyl, 3-methoxypropyl, polyamide, or polyether; R 13 , R 14 , R 15 , R 16 , and R 17are independently H, halogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, sec-amyl, tert-amyl, 2-methylbutyl, 3-methylbutyl, neopentyl, hexyl, 2-ethylhexyl, 2-butyloctyl, hydroxy, methoxy, ethoxy, 2-ethoxyethyl, 3-methoxypropyl, amino, methylamino, dimethylamino, trimethylammonium, trifluoromethyl, or NO.

[0121] In another preferred embodiment, one or more compounds have the cis- and / or trans structure of Formula VII, or a salt thereof: [ka] During the ceremony, Each R1 is H, -CN, alkyl isocyanate, alkyl isothiocyanate, aryl isocyanate, aryl isothiocyanate, and C(O)-XR z are independently selected from X is O or NR'; T is an optionally substituted C-C 20 Alkylene, optionally substituted C-C 20 Alkenylene, optionally substituted C-C 20 Alkynylene, optionally substituted C-C 20 Alkoxyalkylene, optionally substituted C-C 20 Cycloalkylene, optionally substituted C-C 20 Cycloalkenylene, and optionally substituted C-C 20and heterocycloalkylene, wherein one or more skeletal carbon atoms of the linking moiety T are optionally replaced by a divalent group each independently selected from oxygen (—O—), carbonyl (—CO—), optionally substituted alkylamino, optionally substituted cycloalkylene, optionally substituted heterocyclylene, optionally substituted heteroarylene, and optionally substituted arylene; Each R z is H, optionally substituted C 1-15 independently selected from alkyl, optionally substituted hydroxyalkyl, optionally substituted alkoxyalkyl, polyamide, and polyether; Each R3, R5, R6, R7, R8, R9, R 10 , R 13 , R 14 , R 15 , R 16 , and R 17 is H, halogen, optionally substituted C-C 20 Alkyl, optionally substituted C-C 20 Alkenyl, optionally substituted C-C 20 Alkynyl, optionally substituted C3-C8 cycloalkyl, optionally substituted C2-C 20 Cycloalkenyl, optionally substituted C2-C7 heterocycloalkyl, optionally substituted C6-C 10 Aryl, optionally substituted C2-C9 heteroaryl, -OR', -C(O)R', -C(O)OR', -C(O)NR'R'', -C(=NR')NR'R'', -C(=NR'')R', -NR'R'', -CN, -N=NR', cyanate, -OCN, -CNO, -NO2, -OC(O)NR'R'', -SR', -S-SR', -S(O) are independently selected from R', -S(O)2R', -S(O)2OR', -S(O)2NR', -C(O)SR', -C(S)SR', -C(S)NR', ​​-B(OH)2, -B(OR')(OR''), PR'3, PR'2, -P(OR')2, -OP(OR')2, -P(O)(OR')2, -OP(O)(OR')2, polyamides, and polyethers; Each R' and R'' is H, optionally substituted C-C 20 Alkyl, optionally substituted C-C 20 Alkenyl, optionally substituted C-C 20 Alkynyl, optionally substituted C-C 20 Cycloalkyl, optionally substituted C-C 20 Cycloalkenyl, optionally substituted C-C 20 Heterocycloalkyl, optionally substituted C-C 10 independently selected from aryl, optionally substituted C2-C9 heteroaryl, polyamide, and polyether; n is selected from 2, 3, 4, 5, and 6.

[0122] In some embodiments of the composition, T is ethylene, trimethylene, tetramethylene, pentamethylene, 3,3-dimethylpentamethylene, 2,2,3,3-tetramethyltetramethylene, 1,2,3-propanetriyl, phen-1,2-ylene, phen-1,3-ylene, phen-1,4-ylene, bis(ethylene), or 1,3,5-triazine-2,4,6-tolyl; and each R z is independently selected from H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, sec-isoamyl, tert-amyl, 2-methylbutyl, 3-methylbutyl, neopentyl, hexyl, 2-ethylhexyl, 2-butyloctyl, 2-ethoxyethyl, 3-methoxypropyl, polyamide, and polyether; and each R 13 , R 14 , R 15 , R 16 , and R 17are independently selected from H, halogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, sec-amyl, tert-amyl, 2-methylbutyl, 3-methylbutyl, neopentyl, hexyl, 2-ethylhexyl, 2-butyloctyl, hydroxy, methoxy, ethoxy, 2-ethoxyethyl, 3-methoxypropyl, amino, methylamino, dimethylamino, trimethylammonium, trifluoromethyl, and NO.

[0123] In another preferred embodiment, one or more compounds have the cis- and / or trans structure of Formula VIII, or a salt thereof: [ka] During the ceremony, Each R1 is H, -CN, alkyl isocyanate, alkyl isothiocyanate, aryl isocyanate, aryl isothiocyanate, and C(O)-XR z are independently selected from X is O or NR'; T is an optionally substituted C-C 20 Alkylene, optionally substituted C-C 20 Alkenylene, optionally substituted C-C 20 Alkynylene, optionally substituted C-C 20 Alkoxyalkylene, optionally substituted C-C 20 Cycloalkylene, optionally substituted C-C 20 Cycloalkenylene, and optionally substituted C-C 20and heterocycloalkylene, wherein one or more skeletal carbon atoms of the linking moiety T are optionally replaced by a divalent group each independently selected from oxygen (—O—), carbonyl (—CO—), optionally substituted alkylamino, optionally substituted cycloalkylene, optionally substituted heterocyclylene, optionally substituted heteroarylene, and optionally substituted arylene; Each R z is H, optionally substituted C 1-15 independently selected from alkyl, optionally substituted hydroxyalkyl, optionally substituted alkoxyalkyl, polyamide, and polyether; Each R3, R5, R6, R7, R8, R 13 , R 14 , R 15 , R 16 , and R 17 is H, halogen, optionally substituted C-C 20 Alkyl, optionally substituted C-C 20 Alkenyl, optionally substituted C-C 20 Alkynyl, optionally substituted C3-C8 cycloalkyl, optionally substituted C2-C 20 Cycloalkenyl, optionally substituted C2-C7 heterocycloalkyl, optionally substituted C6-C 10 Aryl, optionally substituted C2-C9 heteroaryl, -OR', -C(O)R', -C(O)OR', -C(O)NR'R'', -C(=NR')NR'R'', -C(=NR'')R', -NR'R'', -CN, -N=NR', cyanate, -OCN, -CNO, -NO2, -OC(O)NR'R'', -SR', -S-SR', -S(O) are independently selected from R', -S(O)2R', -S(O)2OR', -S(O)2NR', -C(O)SR', -C(S)SR', -C(S)NR', ​​-B(OH)2, -B(OR')(OR''), PR'3, PR'2, -P(OR')2, -OP(OR')2, -P(O)(OR')2, -OP(O)(OR')2, polyamides, and polyethers; Each R' and R'' is H, optionally substituted C-C 20 Alkyl, optionally substituted C-C 20 Alkenyl, optionally substituted C-C 20 Alkynyl, optionally substituted C-C 20 Cycloalkyl, optionally substituted C-C 20 Cycloalkenyl, optionally substituted C-C 20 Heterocycloalkyl, optionally substituted C-C 10 independently selected from aryl, optionally substituted C2-C9 heteroaryl, polyamide, and polyether; n is selected from 2, 3, 4, 5, and 6.

[0124] In some embodiments of the composition, T is ethylene, trimethylene, tetramethylene, pentamethylene, 3,3-dimethylpentamethylene, 2,2,3,3-tetramethyltetramethylene, 1,2,3-propanetriyl, phen-1,2-ylene, phen-1,3-ylene, phen-1,4-ylene, bis(ethylene), or 1,3,5-triazine-2,4,6-tolyl; and each R z is independently selected from H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, sec-isoamyl, tert-amyl, 2-methylbutyl, 3-methylbutyl, neopentyl, hexyl, 2-ethylhexyl, 2-butyloctyl, 2-ethoxyethyl, 3-methoxypropyl, polyamide, and polyether; and each R 13 , R 14 , R 15 , R 16 , and R 17are independently selected from H, halogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, sec-amyl, tert-amyl, 2-methylbutyl, 3-methylbutyl, neopentyl, hexyl, 2-ethylhexyl, 2-butyloctyl, hydroxy, methoxy, ethoxy, 2-ethoxyethyl, 3-methoxypropyl, amino, methylamino, dimethylamino, trimethylammonium, trifluoromethyl, and NO.

[0125] In yet another preferred embodiment, one or more compounds have the cis- and / or trans structure of formula IX, or a salt thereof: [ka] During the ceremony, X is O or NR'; L is a substituted or unsubstituted C1-C 20 alkyl, alkenyl, alkyne, alkoxyalkyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, aryl, heteroaryl, polyamide, or polyether; Each R 13 , R 14 , R 15 , R 16 , and R 17 is H, halogen, substituted or unsubstituted C1-C 20 Alkyl, C2-C 20 Alkenyl, C2-C 20 Alkynyl, C3-C8 cycloalkyl, C2-C 20 Cycloalkenyl, C2-C7 heterocycloalkyl, C6-C 10Aryl, C2-C9 heteroaryl, OR', C(O)R', C(O)OR', C(O)NR'R'', R'R''NC=NR', R'C=NR'', NR'R'', CN, N=NR', cyanate, NO2, OC(O)NR'R'', SR', S-SR', S(O)R', S(O)2R', S(O)2OR', S(O)2NR', C(O)SR', C(S)SR', C(S)NR', ​​B(OH)2, B(OR')(OR''), PR' 3 , PR'2, P(OR')2, OP(OR')2, P(O)(OR')2, OP(O)(OR')2, polyamide, and polyether; Each R' and R'' is H, substituted or unsubstituted C1-C 20 Alkyl, C1-C 20 Alkenyl, C2-C 20 Alkynyl, C2-C 20 Cycloalkyl, C2-C 20 Cycloalkenyl, C2-C 20 Heterocycloalkyl, C6-C 10 independently selected from aryl, C2-C9 heteroaryl, polyamide, and polyether; Each of R3, R5, R6, R7, R8, R9, and R 10 is as defined for formula I.

[0126] In some embodiments of the composition, each R 13 , R 14 , R 15 , R 16 , and R 17 are independently selected from H, halogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, sec-amyl, tert-amyl, 2-methylbutyl, 3-methylbutyl, neopentyl, hexyl, 2-ethylhexyl, 2-butyloctyl, hydroxy, methoxy, ethoxy, 2-ethoxyethyl, 3-methoxypropyl, amino, methylamino, dimethylamino, trimethylammonium, trifluoromethyl, and NO.

[0127] In some embodiments, the composition is a sunscreen that includes one or more selected from humectants, emollients, preservatives, buffers, chelating agents, fragrances, antioxidants, antimicrobial agents, thickeners, dryness adjusters, and solvents.

[0128] In some embodiments, the sunscreen composition comprises the cis and / or trans compounds of Formula V, VI, VII, VIII, IX, and / or X in an amount ranging from 0.01% to 50% by weight.

[0129] In preferred embodiments, the sunscreen composition is a solution, lotion, emulsion, cream, gel, aerosol, or spray.

[0130] In another preferred embodiment, the composition is a cosmetic composition formulated as a solution, emulsion, lotion, cream, emulsion, foam, gel, ointment, paste, suspension, stick, powder, wax, tablet, aerosol, or spray.

[0131] In a more preferred embodiment, the cosmetic composition is a hair product.

[0132] In another more preferred embodiment, the cosmetic composition is formulated for application to the lips.

[0133] In yet another more preferred embodiment, the cosmetic composition is formulated for hair removal.

[0134] compound The UV-absorbing compounds or salts thereof described herein can be incorporated into the compositions of the present disclosure, either alone or in any combination, by methods well known in the art. The compounds of the present disclosure can also be incorporated with other known UV-absorbing compounds used in sunscreen compositions and other cosmetics, as well as other ingredients to create the desired cosmetic composition. Examples of UV-absorbing compounds approved by U.S. and / or European regulatory authorities for use in cosmetic compositions, including over-the-counter sunscreens, are listed in Tables 1 and 2. Such cosmetic compositions include, but are not limited to, sunscreen compositions with different sun protection factors (SPFs), suntanning preparations, and skin conditioners; hair care compositions (including, but not limited to, hair tonics, styling preparations, pomades, shampoos, conditioners, hair rinses, treatment packs, hair treatments, hair straightening preparations, hair setting preparations, face powders (loose or pressed), eye shadows, eyeliners, eye creams, eye fix creams, mascaras, etc.); lip care products (including, but not limited to, lipsticks, lip balms, lip gloss, lip contour pencil, etc.), nail care products (including but not limited to nail polish, nail polish remover, nail hardener, nail polish, or cuticle remover); foot cream, foot balsam, foot bath, foot powder, insect repellent, deodorant, antiperspirant, shaving products (including but not limited to soaps, creams, foaming creams, foams, gels, after shave products, after shave lotions, fragrances, etc.), which are well known in different forms such as but not limited to sprays, lotions, gels, emulsions, creams, foams, sprays, bars, waxes, etc. For sunscreen and cosmetic compositions, see, for example, U.S. Publication Nos. 2004 / 0062729, 2004 / 0136932, 2005 / 0013782, 2008 / 0014155, 2008 / 0305057, 2009 / 0035234, 2010 / 0135939, 2011 / 0200543, 2012 / 0148647, 2013 / 0078204, and 2016 / 0256371, each of which is incorporated herein by reference in its entirety.U.S. Patent Nos. 2,104,492, 2,276,204, 2,327,899, 2,395,665, 2,853,423, 2,874,090, 2,974,089, 3,004,896, 3,175,950, 3,238,138, 3,244,708, 3,269,903, 3,275,520, 3,403,207, 3,479,428, 3,529,055, 3,697,642, 3,864,473, 3,895,10 No. 4, No. 4,036,951, No. 4,069,309, No. 4,107,290, No. 4,401,649, No. 4,489 ,057, 4,559,225, 4,663,155, 4,671,955, 4,686,099, 4, No. 710,371, No. 4,710,373, No. 4,810,489, No. 4,826,978, No. 4,891,212, No. No. 4,940,574, No. 4,935,533, No. 5,152,983, No. 5,217,709, No. 5,372,805 No. 5,338,539, No. 5,429,820, No. 5,447,715, No. 5,516,506, No. 5,538 ,716, 5,573,753, 5,587,150, 5,605,680, 5,945,090, 5, 945,091, 6,048,517, 6,103,221, 6,165,449, 6,197,281, No. 6,416,773, No. 6,419,907, No. 6,890,521, No. 6,899,866, No. 6,919,473 No. 6,962,692, No. 7,087,692, No. 7,166,273, No. 7,108,860, No. 7,235, No. 587, No. 7,361,785, No. 7,446,230, No. 7,504,528, No. 7,550,134, No. 7,7 No. 13,519, No. 7,611696, No. 7,893,292, No. 7,959,834, No. 8,039,532, No. 8 ,044,058, 8,158,678, 8,829,192, 8,236,287, 8,540,972,Nos. 8,557,227, 8,628,757, 8,697,035, 8,877,166, 8,992,895, 9,539,194, 9,539,195, 9,550,730, 10,632,096, 11,291,621, as well as CH350461A, DE2020 / 10006005U1, EP03 See, e.g., EP0950398A2, FR2526658A2, FR2768730A1, FR2818142B1, FR2852840A1, GB2081716A, WO1992 / 019208A1, WO1994 / 007460A1, WO1996 / 041614A1, WO2008 / 811701A1, and WO2010 / 020668A1. For hair care products such as, but not limited to, shampoos, hair color, and conditioner compositions, see, for example, U.S. Pat. Nos. 4,551,330, 5,553,630, 6,190,645, 8,044,058, and 8,829,192, as well as EP 0165710 A1 and DE 10240863 A1, each of which is incorporated herein by reference in its entirety.

[0135] Efficient UV protection requires coverage of the entire erythema action spectrum (290-400 nm) using a combination of UV-A and / or UV-B absorbing compounds. Typically, formulations contain at least one effective UV-absorbing compound for each segment of the erythema action spectrum: UV-B (290-320 nm), UV-A1I (320-340 nm), and UV-A1 (340-400 nm). Some compounds absorb UV radiation in more than one segment of the erythema action spectrum, allowing for a reduction in the concentration of sunscreen ingredients required to produce an effective UV-absorbing formulation. The disclosed compounds or salts thereof are disclosed for use in cosmetic compositions containing sunscreens in the range of 0.01 to 50 wt %, preferably 0.03 to 40 wt %, preferably 0.07 to 30 wt %, preferably 0.10 to 25 wt %, preferably 0.15 to 20 wt %, more preferably 0.2 to 15 wt %, even more preferably 0.3 to 12 wt %, and most preferably 0.5 to 10 wt % of the total weight of the composition. In some embodiments, the amount of UV-absorbing compound is in the range of 1.0 wt % to 7.5 wt % of the total weight of the composition. In some cases, one or more of the disclosed compounds may be sufficient to produce a desired cosmetic composition. In some other cases, one or more of the disclosed compounds or salts thereof may be combined with other known UV-absorbing ingredients currently on the market to produce compositions that provide broad-spectrum UV protection. Some of the cosmetic compositions of the present disclosure may contain one or more SPF boosters, sunscreen solvents, and light stabilizers, such as, but not limited to, those listed in Table 3.

[0136] Sunscreen compositions comprising only one or more compounds of the present disclosure or salts thereof can achieve an SPF of 50, 45, 40, 35, 30, 25, 20, 15, or 10 using less than 24 wt.%, preferably less than 20 wt.%, preferably less than 18 wt.%, more preferably less than 15 wt.%, more preferably less than 14 wt.%, even more preferably less than 13 wt.%, even more preferably less than 12 wt.%, and most preferably less than 10 wt.% of total UV absorbing ingredients by weight of the total composition. In combination with other sunscreen ingredients, this can be reduced to less than 15 wt.%, preferably less than 12 wt.%, more preferably less than 10 wt.%, or even less than 7 wt.% of the total composition. [Table 1] [Table 2-1] [Table 2-2] [Table 3]

[0137] In some embodiments, the cosmetic compositions of the present disclosure may contain skin tanning and / or browning agents (self-tanning), such as, but not limited to, dihydroxyacetone (DHA).

[0138] The compositions of the present disclosure may also include one or more cosmetic additives such as, but not limited to, fatty substances, vegetable oils, water, organic solvents, ionic or nonionic thickeners, emollients, humectants, antioxidants, moisturizers, exfoliants, free radical scavengers, stain inhibitors, antibacterial agents, anti-inflammatory agents, pigment removal agents, pigmentation promoters, opacifiers, stabilizers, emollients, silicones, antifoaming agents, insect repellents, fragrances, preservatives, anionic, cationic, nonionic, zwitterionic, or amphoteric surfactants, fillers, pigments, polymers, propellants, oxidizing or basifying agents, or any other ingredient commonly used in cosmetics and / or dermatology.

[0139] The fatty substance may consist of an oil or wax or a mixture thereof. The term "oil" refers to a compound that is liquid at room temperature. The term "wax" refers to a compound that is solid or substantially solid at room temperature and generally has a melting point above 35°C. Oils that may be mentioned include mineral oils such as paraffin, vegetable oils including, but not limited to, sweet almond oil, macadamia oil, blackcurrant seed oil, or jojoba oil; perhydrosqualene, fatty alcohols, fatty acids or fatty acid esters (e.g., C12-C15 alcohol benzoate sold by WITCO® under the trademark FINSOLV TN®), octyl palmitate, isopropyl lanolate, triglycerides (including capric / caprylic triglyceride, oxyethylenated or oxypropylenated fatty acid esters and ethers); silicone oils, such as cyclomethicone, polydimethylsiloxane (PDMS), fluorinated oils, and synthetic oils such as polyalkylenes. Waxy compounds that may be mentioned include paraffin, carnauba wax, beeswax, and hydrogenated castor oil.

[0140] The cosmetic composition may contain one or more solvents selected from water or organic solvents, such as, but not limited to, ethyl acetate, acetone, or lower alcohols, such as, but not limited to, ethanol, propanol, isopropanol, butanol, isobutanol, pentanol, isopentanol, hexanol, and their isomers. Polyols, such as glycols, including, but not limited to, ethylene glycol, propylene glycol, butylene glycol, dipropylene glycol (both isomers), or diethylene glycol; glycerol, reducing sugars, and derivatives thereof, such as, but not limited to, their methyl ethers or ethyl ethers.

[0141] Many suitable thickeners can be used to formulate the compositions of the present disclosure, such as, but not limited to, crosslinked acrylic polymers, for example, carbomer, acrylates / C10-C30 alkyl acrylate crosspolymers (e.g., polyacrylate-3 sold under the name PEMULEN™ or VISCOPHOBE™ DB 1000 by AMERCOL™ CO.), emulsions of polyacrylamide, C13-C14 isoparaffin, and poly-acrylamides such as laureth-7 (sold under the name SEPIGEL 305™ by SEPPIC™), AMPS homopolymers or copolymers such as HOSTACERIN™ AMPS sold by CLARIANT™, modified or unmodified guar gum and celluloses, for example, hydroxypropyl guar gum, methylhydroxyethyl methylcellulose, and hydroxypropyl methylcellulose, xanthan gum, and Aerosil-type nanometer silicas such as AEROSIL™ 200.

[0142] The composition of the present disclosure may be prepared to contain one or more compounds of the present disclosure or their salts by techniques well known to those skilled in the art, such as those for preparing oil-in-water or water-in-oil emulsions.In particular, the composition may be in the form of a simple or complex emulsion (O / W, W / O, O / W / O, or W / O / W emulsion), such as cream or milk, in the form of a gel or cream-gel, or in the form of a lotion, oil, powder, or solid tube, and may optionally be packaged as an aerosol, or in the form of a mousse or spray.In some embodiments, the composition is preferably in the form of an oil-in-water or water-in-oil emulsion.The aqueous phase of the emulsion may comprise a nonionic vesicular dispersion prepared according to known processes (see, for example, Bangham, Standish, and Watkins, J. Mol. Biol. 13, 238 (1965), FR-2,315,991, and FR-2,416,008, each of which is incorporated by reference in its entirety). For human skin care products, the compositions may be in the form of a suspension or dispersion in a solvent or fatty substance, in the form of a non-ionic vesicular dispersion, or in the form of an emulsion, preferably of the oil-in-water type such as a cream or milk, or in the form of an ointment, gel, cream-gel, sunscreen oil, solid tube, powder, aerosol mousse, or spray.

[0143] In some embodiments, the composition is a hair care product. It may be in the form of a shampoo, lotion, gel, emulsion, or nonionic vesicular dispersion, and may constitute, for example, a rinse-out composition, a styling or treating lotion or gel, a blow-drying or hair-setting lotion or gel, or a composition for permanently waving, straightening, dyeing, or bleaching hair, to be applied before or after shampooing, before or after dyeing or bleaching, or before, during, or after permanently waving or straightening hair.

[0144] In some other embodiments, the composition is a makeup composition such as a nail polish, eyelash, eyebrow, or skin care product (including epidermal treatment cream, foundation, tube lipstick, eye shadow, mascara, or eyeliner), and can be in a solid or paste form, anhydrous or aqueous form, for example, an oil-in-water or water-in-oil emulsion, a non-ionic vesicular dispersion, or a suspension.

[0145] The sunscreen formulations of the present disclosure are of the oil-in-water emulsion type, wherein the aqueous phase is in the range of 50% to 95% by weight, preferably in the range of 60% to 90% by weight, more preferably in the range of 70% to 90% by weight, the oil phase is in the range of 5% to 50% by weight, preferably in the range of 10% to 40% by weight, more preferably in the range of 15% to 30% by weight, and the emulsifier(s) is in the range of 0.5% to 20% by weight, preferably in the range of 2% to 10% by weight, more preferably in the range of 3% to 7% by weight, of the total weight of the phases of the composition.

[0146] A second aspect of the present disclosure is directed to a method of using a cosmetic composition to protect a subject from UV-A and UV-B radiation. The method comprises applying an effective amount of the composition of the present disclosure to the skin or lips of the subject. Application can be carried out by spraying, aerosolizing, spreading a cream lotion, stick, or the like. The subject can be any animal, preferably a mammal, and most preferably a human.

[0147] Compositions for protecting surfaces from UV damage: The UV absorbing compounds and salts thereof described herein can be incorporated into any well-known compositions used to protect surfaces from environmental damage in the art, including, but not limited to, coatings, paints, resins, adhesives, polymers, shoe polish, varnishes, floor cleaners and polishes, waxes, dyes, household products such as, but not limited to, detergents, fabric softeners, and the like, scouring agents; glass cleaners; mild cleaners (such as all-purpose cleaners), household cleaners for the kitchen and bathroom; rinse aids; dishwashing agents; kitchen cleaners; oven cleaners; metal, glass, and ceramic cleaners; fabric care products; rug cleaners; carpet shampoos; rust removal compositions, stains; furniture polishes, all-purpose polishes, leather and vinyl dressing compositions, and the like.They may also be incorporated into materials such as polymers used in automobiles, airplanes, spacecraft, boats, and marine vessels, see, for example, US 2005 / 0171253, and U.S. Pat. Nos. 3,004,896, 3,134,748, 3,201,366, 3,205,193, 3,211,696, 3,213,058, 3,214 ,436, No. 3,218,285, No. 3,230,194, No. 3,239,483, No. 3,253,921, No. 3,271,339, No. 3,282,886, No. 3,284,38 No. 7, No. 3,301,816, No. 3,322,718, No. 3,368,916, No. 3,429,732, No. 3,467,482, No. 3,499,869, No. 3,900,442, No. 3,925,509, No. 3,936,418, No. 3,954,706, No. 4,323,633, No. 4,344,830, No. 4,381,360, No. 4,431,762, No. 4 , 749,643, 4,816,504, 4,839,405, 5,086,097, 5,204,390, 5,330,672, 5,380,774, 5,67 See Nos. 4,670, 6,191,199, 6,194,493, 6,268,415, 6,296,674, 6,401,724, 6,797,751, 6,916,867, 6,930,136, 7,153,588, 7,695,643, 8,906,987, 10,596,087, and 10,619,098. Additionally, fabric care compositions such as, but not limited to, fabric softeners and detergents are well known in the art, see, for example, U.S. Pat. Nos. 4,153,744, 5,134,223, 5,330,672, 5,374,362, 5,474,691, 5,705,474, 5,723,435, 6,916,778, and 7,087,692, each of which is incorporated herein by reference in its entirety.

[0148] The UV absorbing compounds and salts thereof of the present disclosure may also be used as additives to organic materials such as natural or synthetic organic polymers, adhesives, paints, or chemically modified organic materials, alone or in combination with other known UV absorbing components, such as, but not limited to, those listed in Table 4. Examples include polymers of mono-olefins and diolefins, mixtures of polymers of mono-olefins and diolefins, copolymers of mono-olefins and diolefins with each other or with other vinyl monomers; hydrocarbon resins, including hydrogenated modifications thereof (e.g., tackifiers) and mixtures of polyalkylenes with starch; polystyrene, poly(p-methylstyrene), poly(α-methylstyrene); aromatic homopolymers and copolymers derived from vinyl aromatic monomers, copolymers of vinyl aromatic monomers with comonomers (such as, but not limited to, ethylene, propylene, dienes, nitriles, acids, maleic anhydride, maleimide, vinyl acetate, and vinyl chloride, or acrylic derivatives, and mixtures thereof), hydrogenated aromatic polymers derived from the hydrogenation of aromatic homopolymers and copolymers derived from vinyl aromatic monomers, ethylene, propylene, dienes, nitriles, copolymers of vinyl aromatic monomers and comonomers selected from acids, maleic anhydride, maleimide, vinyl acetate, and vinyl chloride, or acrylic derivatives and mixtures thereof; graft copolymers of vinyl aromatic monomers; halogen-containing polymers, in particular polymers of halogen-containing vinyl compounds such as, but not limited to, polyvinyl chloride, polyvinylidene chloride, polyvinyl fluoride, polyvinylidene fluoride, and copolymers thereof, for example, but not limited to, vinyl chloride / vinylidene chloride, vinyl chloride / vinyl acetate, or vinylidene chloride / vinyl acetate; polymers derived from α,β-unsaturated acids and their derivatives; copolymers of α,β-unsaturated acids and their derivatives with each other or with other unsaturated monomers; polymers derived from unsaturated alcohols and amines or their acyl derivatives or acetals, and copolymers thereof with polymers of mono- and di-olefins;Homopolymers and copolymers of cyclic ethers such as polyalkylene glycols, polyethylene oxide, polypropylene oxide, or copolymers thereof with bisglycidyl ethers; polyacetals such as polyoxymethylene and those containing ethylene oxide as a comonomer, thermoplastic polyurethanes, acrylates, or polyacetals modified with MBS; polyphenylene oxides and sulfides, and mixtures of polyphenylene oxide with styrene polymers or polyamides; polyurethanes derived from hydroxyl-terminated polyethers, polyesters, or polybutadienes on the one hand, and aliphatic or aromatic polyisocyanates, and their precursors, on the other hand; polyamides and copolyamides derived from diamines and dicarboxylic acids and / or aminocarboxylic acids or the corresponding lactams; polyureas, polyimides, polyamide-imides, polyetherimides, polyesterimides, polyhydantoins, and polybenzimidazoles; dicarboxylic acids and diols, and / or hydroxycarboxylic acids or the corresponding lactones or crosslinked polymers derived from the polymerization of aldehydes with phenols, ureas, and melamines, such as, but not limited to, phenol / formaldehyde resins, urea / formaldehyde resins, and melamine / formaldehyde resins; drying and non-drying alkyd resins; unsaturated polyester resins derived from copolyesters of saturated and unsaturated dicarboxylic acids with polyhydric alcohols and vinyl compounds as crosslinkers, as well as their low-flammability halogen-containing modifications; crosslinkable acrylic resins derived from substituted acrylates, such as epoxy acrylates, urethane acrylates, or polyester acrylates; alkyd resins, polyester resins, and acrylate resins crosslinked with melamine resins, urea resins, isocyanates, isocyanurates, polyisocyanates, or epoxy resins;Crosslinked epoxy resins derived from aliphatic, alicyclic, heterocyclic, or aromatic glycidyl compounds (for example, but not limited to, the products of diglycidyl ethers of bisphenol A and bisphenol F, which are crosslinked with conventional hardeners such as anhydrides or amines, with or without accelerators); natural polymers such as cellulose, rubber, gelatin, and their chemically modified homologous derivatives (for example, but not limited to, cellulose acetate, cellulose propionate, and cellulose butyrate, or cellulose ethers such as methylcellulose), rosin, and rosin derivatives; blends of polymers (for example, but not limited to, PP / EPDM, polyamide / EPDM, or ABS, PVC / EVA, PVC / ABS, PVC / MBS, PC / ABS, PBTP / ABS, PC / ASA, PC / PBT, PVC / CPE, PVC / acrylate, POM / thermoplastic PUR, PC / thermoplastic PUR, POM / acrylate, POM / MBS, PPO / HIPS, PPO / PA 6.6, and copolymers, PA / HDPE, PA / PP, PA / PPO, PBT / PC / ABS, or PBT / PET / PC), naturally occurring and synthetic organic materials, which are pure monomeric compounds or mixtures of such compounds; aqueous emulsions of natural and synthetic rubbers (e.g., natural latex(s) of carboxylated styrene / butadiene copolymers), including, but not limited to, ethylene oxide, propylene oxide, diisocyanate derivatives, dithioisocyanate derivatives, and the like, as described above. In some embodiments of the present disclosure, suitable derivatives of the compounds disclosed herein may be used in copolymerization of the polymers referred to herein; [Table 4] [Table 5]

[0149] In some embodiments, one or more compounds of the present disclosure may be added to a photolabile compound, such as, but not limited to, the compounds of Table 5 and compositions thereof.

[0150] The compounds of the present disclosure can photostabilize these photolabile compounds by quenching the excited state of the unstable chemical and then dissipating energy via a non-radiative internal conversion process. To achieve photostabilization of a photolabile compound, the concentration of the compounds of the present disclosure on a molar percentage basis relative to the photolabile compound should be in the range of 1 mol% to 400 mol%, preferably in the range of 25 mol% to 300 mol%, more preferably in the range of 50 mol% to 200 mol%, and most preferably in the range of 70 mol% to 100 mol%. [Example]

[0151] Example 1 Synthesis of UV-absorbing compounds: Compounds E1–E11 and E14–E39 were synthesized by the Knoevenagel condensation method. In a typical synthesis, a solution of ketone X (1.0 equiv.), compound Y (selected from malononitrile, malonate ester, 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum's acid), cyanoacetate ester, etc. (1.1 equiv.), and ammonium carboxylate, e.g., ethylenediamine diacetate or ammonium acetate (0.2 equiv.), in a round-bottom flask in a mixture of carboxylic acid (42%), such as acetic acid or propionic acid, and a hydrocarbon solvent (e.g., cyclohexane or toluene) was heated under reflux. The water product of the reaction was removed by a Dean-Stark trap, optionally containing molecular sieves. The reaction progress was monitored by TLC and / or UV-Vis spectroscopy until completion. The reaction mixture was then concentrated in vacuo, and the residue was dissolved in ethyl acetate. The organic solution was then subjected to standard workup to produce a solid or oily residue. The oily residue was adsorbed onto Celite and subjected to silica gel chromatography, eluting the product with a blend of hexane and ethyl acetate. The appropriate fractions were collected and concentrated in vacuo to give the product. All compounds were prepared at 0.01 g L -1 The compounds were characterized by spectroscopic methods, including UV-Vis spectra obtained in 1,4-dioxane solutions of 1,4-dioxane. Table 6 lists the names of the compounds prepared, λ max Figure 1 shows the UV absorption spectrum of (E5). Figure 2 shows the UV absorption spectrum of (E5). 1 Figure 3 shows the H-NMR spectrum of (E6). 1 Figure 4 shows the H-NMR spectrum of (E7). 1 Figure 5 shows the H-NMR spectrum of (E8). 1 The H-NMR spectrum is shown. Table 7 lists the structures of the compounds used in the above-mentioned methods and the starting materials for compounds X and Y.

[0152] Compounds E40-E44 can be synthesized by the methods described above using the starting materials listed in Table 7.

[0153] Example 2 Synthesis of UV-absorbing compounds: Compounds E45–E47 and E49 were synthesized by the Horner-Wadsworth-Emmons method. In a typical reaction, a solution of ketone X (1.0 equiv.), diethylphosphonoacetate Y (1.1 equiv.), lithium chloride (3.0 equiv.), and 1,8-diazabicyclo(5.4.0)undec-7-ene (3.0 equiv.) in acetonitrile (0.1 M) was heated and stirred under reflux for 16 hours under a nitrogen atmosphere. The reaction mixture was concentrated in vacuo, and the residue was dissolved in ethyl acetate. The organic solution was then subjected to standard workup to yield a solid or oily residue. The solid or oily residue was adsorbed onto Celite and chromatographed to purify and characterize the product described in Example 1. Table 6 lists the names of the compounds prepared, λ max ε, and E 1% Table 7 lists the structures of the compounds used in the above-described methods and the starting materials for compounds X and Y. Compounds E48 and E50-E64 can be synthesized by the above-described methods using the starting materials listed in Table 7. [Table 6-1] [Table 6-2] [Table 6-3] [Table 6-4] [Table 6-5] [Table 6-6] [Table 6-7] Table 7-1 Table 7-2 Table 7-3 Table 7-4 Table 7-5 Table 7-6 Table 7-7 Table 7-8 Table 7-9 Table 7-10 Table 7-11 Table 7-12 Table 7-13 Table 7-14 [Table 8-1] [Table 8-2] [Table 8-3] [Table 8-4] [Table 8-5] [Table 8-6] [Table 8-7]

[0154] Example 3 Compounds E12 and E13 were prepared from compound E11 described above by a transesterification reaction.

[0155] (a) Dimethyl (3-phenyl-2-cyclohexen-1-ylidene)malonate (E12): [ka] Compound 12 was obtained by dissolving 2,2-dimethyl-5-(3-phenyl-2-cyclohexen-1-ylidene)-1,3-dioxane-4,6-dione (E11, 812.7 mg, 2.724 mmol) and p-toluenesulfonic acid monohydrate (110.4 mg, 0.5803 mmol) in 30 mL of methanol and heating the solution under reflux. The reaction was monitored by thin-layer chromatography or UV-Vis spectroscopy. Upon completion, the reaction was cooled to room temperature. The methanol was evaporated in vacuo. The resulting oil was subjected to standard workup to yield a yellow oil (0.2019 g, 26%).

[0156] (b) Synthesis of polyethylene(3-phenyl-2-cyclohexen-1-ylidene)malonate (E13): [ka] Compound 13 can be obtained by heating a mixture of 2,2-dimethyl-5-(3-phenyl-2-cyclohexen-1-ylidene)-1,3-dioxane-4,6-dione (E11, 305.1 mg, 1.023 mmol), ethylene glycol (0.15 mL, 2.68 mmol), zinc acetate (0.9 mg, 0.005 mmol), pentaerythritol tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate) (0.8 mg, 0.0007 mmol), and triphenyl phosphate (0.5 mg, 0.002 mmol) to 140 °C with stirring under a nitrogen atmosphere. The reaction can be monitored by UV / Vis spectroscopy, and the acetone and acetal diproduct should be removed by distillation. The polycondensation catalyst, antimony trioxide (1.0 mg, 0.0034 mmol), can then be added to the reaction mixture as a suspension in diol under positive nitrogen pressure, followed by heating to 190 °C and distilling off the diol under 50 mTorr pressure for 30 minutes to drive the polycondensation reaction. The reaction is complete in 12 hours, and the mixture can be cooled to room temperature (approximately 23 °C) and dissolved in minimal chloroform. The resulting solution can be added dropwise to a stirred solution of isopropanol to precipitate the product polymer (E13), which can be collected by filtration.

[0157] Example 4 Sunscreen composition: The ingredients for phases A, B, C, D, and E are weighed out separately and combined. Phases A and B are mixed and heated to 80°C, after which the mixture is homogenized, and phases C and D are added sequentially while the mixture is heated to 75°C. Phase E is then slowly added, and the mixture is thoroughly homogenized for 3 minutes. The homogenized mixture is cooled to below 50°C, and the ingredients for phase F are added sequentially with continuous mixing and homogenized. Finally, the mixture is cooled to room temperature. (a) SPF15 sunscreen: [Table 9] (b) SPF15 sunscreen: [Table 10]

[0158] (c) SPF 30 sunscreen: The ingredients for Phase A are mixed and heated to 80°C, followed by the sequential addition of the mixtures for Phases B and C. In a separate container, the ingredients for Phase D are combined while mixing and heating to 75°C, and then the mixture for ABC is added to Phase D. The mixture for ABCD is homogenized for 3 minutes, cooled to below 50°C, and the ingredients for Phase E are added sequentially while mixing. Finally, the mixture is cooled to room temperature. [Table 11]

[0159] Example 5 Hair conditioners containing sunscreen: The ingredients for Phase A and B are mixed thoroughly separately while heating to 71°C, and then the two phases are mixed and homogenized. The mixture is then cooled to 40°C, and the ingredients for Phase C are added sequentially and stirred. The pH of the mixture is adjusted to 4-5.5 using citric acid. [Table 12]

[0160] Equivalents and Incorporation by Reference While aspects of the present disclosure have been particularly illustrated with reference to certain specific embodiments and various alternative embodiments, it will be understood by those skilled in the art that various changes in form and detail can be made therein without departing from the spirit and scope of the present disclosure.

[0161] All references, issued patents, and patent applications cited within the body of this specification are hereby incorporated by reference in their entirety for all purposes.

Claims

1. A compound of Formula I or Formula II: 【Chemistry 40】 or a salt thereof, During the ceremony, R １ and R ２ is H, optionally substituted alkyl, optionally substituted alkynyl, optionally substituted aminoalkyl, optionally substituted hydroxyalkyl, optionally substituted alkoxyalkyl, —CN, —C(O)R′, —C(O)OR′, —C(O)NR′R″, —C(O)SR′, —C(S)NR′R″, —NCO, —C(O)—X—R ｙ , C(O)-X-R ｚ , and -NO ２ are independently selected from, or R １ and R ２ together with the carbon atoms to which they are attached form a cyclic moiety of formula III or formula IV, 【Chemistry 41】 During the ceremony, X is O or NR′; R １１ and R １２ is independently selected from H and optionally substituted alkyl; R ｙ and R ｚ is H, optionally substituted C １－１５ independently selected from alkyl, optionally substituted hydroxyalkyl, optionally substituted alkoxyalkyl, polyamide, and polyether; R ４ is an optionally substituted C ６ -C １０ Optionally substituted C containing 0-4 heteroatoms selected from aryl, O, N, and S ２ -C ９ heteroaryl; Each R ３ , R ５ , R ６ , R ７ , R ８ , R ９ , and R １０ is H, halogen, optionally substituted C １ -C ２０ Alkyl, optionally substituted C ２ -C ２０ Alkenyl, optionally substituted C ２ -C ２０ Alkynyl, optionally substituted C ３ -C ８ Cycloalkyl, optionally substituted C ２ -C ２０ Cycloalkenyl, optionally substituted C ２ -C ７ Heterocycloalkyl, optionally substituted C ６ -C １０ Aryl, optionally substituted C ２ -C ９ Heteroaryl, —OR′, —C(O)R′, —C(O)OR′, —C(O)NR′R″, —C(═NR′)NR′R″, —C(═NR″)R′, —NR′R″, —CN, —N═NR′, cyanate, —OCN, —CNO, —NO ２ , -OC(O)NR'R'', -SR', -S-SR', -S(O)R', -S(O) ２ R', -S(O) ２ OR', -S(O) ２ NR', -C(O)SR', -C(S)SR', -C(S)NR', ​​-B(OH) ２ , -B(OR')(OR''),PR' ３ , P.R.' ２ , -P(OR') ２ , -OP(OR') ２ , -P(O)(OR') ２ , -OP(O)(OR') ２ , polyamide, and polyether; Each R′ and R″ is H, optionally substituted C １ -C ２０ Alkyl, optionally substituted C ２ -C ２０ Alkenyl, optionally substituted C ２ -C ２０ Alkynyl, optionally substituted C ２ -C ２０ Cycloalkyl, optionally substituted C ２ -C ２０ Cycloalkenyl, optionally substituted C ２ -C ２０ Heterocycloalkyl, optionally substituted C ６ -C １０ Aryl, optionally substituted C ２ -C ９ The composition is independently selected from heteroaryls, polyamides, and polyethers.

2. The composition of claim 1 , wherein the compound is a compound of formula I:

3. 10. The composition of claim 1, wherein the compound is a compound of formula II.

4. R ４ The composition of any one of claims 1 to 3, wherein is optionally substituted phenyl.

5. R １ and R ２ At least one of the groups is —C(O)—X—R ｙ The composition according to any one of claims 1 to 4, wherein

6. The composition comprises one or more compounds having the cis- and / or trans-structure of Formula V or Formula VI: 【Chemistry 42】 or salts thereof, During the ceremony, R １ is H, —CN, alkyl isocyanate, alkyl isothiocyanate, aryl isocyanate, aryl isothiocyanate, and C(O)—X—R ｚ is selected from Each R １３ , R １４ , R １５ , R １６ , and R １７ is H, halogen, optionally substituted C １ -C ２０ Alkyl, optionally substituted C ２ -C ２０ Alkenyl, optionally substituted C ２ -C ２０ Alkynyl, optionally substituted C ３ -C ８ Cycloalkyl, optionally substituted C ２ -C ２０ Cycloalkenyl, optionally substituted C ２ -C ７ Heterocycloalkyl, optionally substituted C ６ -C １０ Aryl, optionally substituted C ２ -C ９ Heteroaryl, —OR′, —C(O)R′, —C(O)OR′, —C(O)NR′R″, —C(═NR′)NR′R″, —C(═NR″)R′, —NR′R″, —CN, —N═NR′, cyanate, —OCN, —NO ２ , -OC(O)NR'R'', -SR', -S-SR', -S(O)R', -S(O) ２ R', -S(O) ２ OR', -S(O) ２ NR', -C(O)SR', -C(S)SR', -C(S)NR', ​​-B(OH) ２ , -B(OR')(OR''), -PR' ２ , -P(OR') ２ , -OP(OR') ２ , -P(O)(OR') ２ , -OP(O)(OR') ２ 6. The composition of claim 5, wherein the polyethers are independently selected from the group consisting of polyamides, polyethers, and polyols.

7. R １ The composition of claim 6, wherein is —CN.

8. R １ The composition of claim 6, wherein is —H.

9. R １ But -C(O)-X-R ｚ The composition of claim 6, wherein

10. R ｙ and R ｚ is optionally substituted C １－１５ The composition of any one of claims 1 to 9, wherein the alkyl is alkyl.

11. The composition of any one of claims 1 to 10, wherein X is O.

12. The composition of any one of claims 1 to 10, wherein X is NH.

13. Each R ｙ and R ｚ are independently selected from H, methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, pentyl, sec-amyl, tert-amyl, 2-methylbutyl, 3-methylbutyl, neopentyl, hexyl, 2-ethylhexyl, 2-butyloctyl, 2-ethoxyethyl, and 3-methoxypropyl; Each R ３ , R ５ , R ６ , R ７ , R ８ , R ９ , R １０ , R １３ , R １４ , R １５ , R １６ , and R １７ is H, halogen, methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, pentyl, sec-amyl, tert-amyl, 2-methylbutyl, 3-methylbutyl, neopentyl, hexyl, 2-ethylhexyl, 2-butyloctyl, hydroxy, methoxy, ethoxy, 2-ethoxyethyl, 3-methoxypropyl, amino, methylamino, dimethylamino, trimethylammonium, trifluoromethyl, and —NO ２ The composition of any one of claims 6 to 12, independently selected from:

14. R ｙ and R ｚ but, 【Chemistry 43】 The composition of any one of claims 1 to 13, independently selected from:

15. R ４ but, 【Chemistry 44】 The composition according to any one of claims 1 to 14, selected from:

16. 10. The composition of claim 1, wherein the composition comprises one or more compounds selected from E1 to E64 of Table 6.

17. Cis and / or trans compounds having the structure of Formula V or VI: 【Chemistry 45】 or a salt thereof, During the ceremony, R １ is H, —CN, alkyl isocyanate, alkyl isothiocyanate, aryl isocyanate, aryl isothiocyanate, or C(O)—X—R ｚ and X is O or NR′; Each R ｙ and R ｚ is H, optionally substituted C １ -C １５ Alkyl, optionally substituted C １ -C １５ Hydroxyalkyl, optionally substituted C １ -C １５ independently selected from alkoxyalkyl, polyamide, and polyether; Each R ３ , R ５ , R ６ , R ７ , R ８ , R ９ , R １０ , R １３ , R １４ , R １５ , R １６ , and R １７ is H, halogen, optionally substituted C １ -C ２０ Alkyl, optionally substituted C ２ -C ２０ Alkenyl, optionally substituted C ２ -C ２０ Alkynyl, optionally substituted C ３ -C ８ Cycloalkyl, optionally substituted C ２ -C ２０ Cycloalkenyl, optionally substituted C ２ -C ７ Heterocycloalkyl, optionally substituted C ６ -C １０ Aryl, optionally substituted C ２ -C ９ Heteroaryl, OR', C(O)R', C(O)OR', C(O)NR'R'', -C(=NR')NR'R'', -C(=NR'')R', NR'R'', CN, N=NR', cyanate, NO ２ , OC(O)NR'R'', SR', S-SR', S(O)R', S(O) ２ R', S(O) ２ OR', S(O) ２ NR', C(O)SR', C(S)SR', C(S)NR', ​​B(OH) ２ , B(OR') (OR''), PR' ３ , P.R.' ２ , P(OR′) ２ , OP(OR') ２ , P(O)(OR') ２ ,OP(O)(OR') ２ , polyamide, and polyether; Each R′ and R″ is H, optionally substituted C １ -C ２０ Alkyl, optionally substituted C １ -C ２０ Alkenyl, optionally substituted C ２ -C ２０ Alkynyl, optionally substituted C ２ -C ２０ Cycloalkyl, optionally substituted C ２ -C ２０ Cycloalkenyl, optionally substituted C ２ -C ２０ Heterocycloalkyl, optionally substituted C ６ -C １０ Aryl, optionally substituted C ２ -C ９ A compound or a salt thereof independently selected from heteroaryls, polyamides, and polyethers.

18. R １ The compound of claim 17, wherein is -CN.

19. R １ The compound of claim 17, wherein is —H.

20. R １ But -C(O)-X-R ｚ 18. The compound of claim 17, wherein:

21. R ｙ and R ｚ are independently optionally substituted C １－１５ The compound of any one of claims 17 to 20, which is alkyl.

22. The compound of any one of claims 17 to 21, wherein X is O.

23. The compound of any one of claims 17 to 21, wherein X is NH.

24. Each R ｙ and R ｚ are independently selected from H, methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, pentyl, sec-amyl, tert-amyl, 2-methylbutyl, 3-methylbutyl, neopentyl, hexyl, 2-ethylhexyl, 2-butyloctyl, 2-ethoxyethyl, and 3-methoxypropyl; Each R ３ , R ５ , R ６ , R ７ , R ８ , R ９ , R １０ , R １３ , R １４ , R １５ , R １６ , and R １７ is H, halogen, methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, pentyl, sec-amyl, tert-amyl, 2-methylbutyl, 3-methylbutyl, neopentyl, hexyl, 2-ethylhexyl, 2-butyloctyl, hydroxy, methoxy, ethoxy, 2-ethoxyethyl, 3-methoxypropyl, amino, methylamino, dimethylamino, trimethylammonium, trifluoromethyl, and —NO ２ The compound of any one of claims 17 to 23, independently selected from:

25. R ｙ and R ｚ but, 【Chemistry 46】 The compound of any one of claims 17 to 24, independently selected from:

26. The compound is R １３ , R １４ , R １５ , R １６ , and R １７ The following substituted phenyl groups defined by: 【Chemistry 47】 The compound according to any one of claims 17 to 25, comprising one of:

27. 18. The compound of claim 17, wherein the compound is selected from the compounds of Table 6.

28. A compound of formula VII or formula VIII: 【Chemistry 48】 or a salt thereof, During the ceremony, Each R １ is H, —CN, alkyl isocyanate, alkyl isothiocyanate, aryl isocyanate, aryl isothiocyanate, and C(O)—X—R ｚ are independently selected from X is O or NR′; T is an optionally substituted C １ -C ２０ Alkylene, optionally substituted C ２ -C ２０ Alkenylene, optionally substituted C ２ -C ２０ Alkynylene, optionally substituted C ２ -C ２０ Alkoxyalkylene, optionally substituted C ２ -C ２０ Cycloalkylene, optionally substituted C ２ -C ２０ Cycloalkenylene, and optionally substituted C ２ -C ２０ and heterocycloalkylene, wherein one or more backbone carbon atoms of said linking moiety T are optionally replaced by a divalent group each independently selected from oxygen (—O—), carbonyl (—CO—), optionally substituted alkylamino, optionally substituted cycloalkylene, optionally substituted heterocyclylene, optionally substituted heteroarylene, and optionally substituted arylene; Each R ｚ is H, optionally substituted C １－１５ independently selected from alkyl, optionally substituted hydroxyalkyl, optionally substituted alkoxyalkyl, polyamide, and polyether; Each R ３ , R ５ , R ６ , R ７ , R ８ , R ９ , R １０ , R １３ , R １４ , R １５ , R １６ , and R １７ is H, halogen, optionally substituted C １ -C ２０ Alkyl, optionally substituted C ２ -C ２０ Alkenyl, optionally substituted C ２ -C ２０ Alkynyl, optionally substituted C ３ -C ８ Cycloalkyl, optionally substituted C ２ -C ２０ Cycloalkenyl, optionally substituted C ２ -C ７ Heterocycloalkyl, optionally substituted C ６ -C １０ Aryl, optionally substituted C ２ -C ９ Heteroaryl, —OR′, —C(O)R′, —C(O)OR′, —C(O)NR′R″, —C(═NR′)NR′R″, —C(═NR″)R′, —NR′R″, —CN, —N═NR′, cyanate, —OCN, —CNO, —NO ２ , -OC(O)NR'R'', -SR', -S-SR', -S(O)R', -S(O) ２ R', -S(O) ２ OR', -S(O) ２ NR', -C(O)SR', -C(S)SR', -C(S)NR', ​​-B(OH) ２ , -B(OR')(OR''),PR' ３ , P.R.' ２ , -P(OR') ２ , -OP(OR') ２ , -P(O)(OR') ２ , -OP(O)(OR') ２ , polyamide, and polyether; Each R′ and R″ is H, optionally substituted C １ -C ２０ Alkyl, optionally substituted C ２ -C ２０ Alkenyl, optionally substituted C ２ -C ２０ Alkynyl, optionally substituted C ２ -C ２０ Cycloalkyl, optionally substituted C ２ -C ２０ Cycloalkenyl, optionally substituted C ２ -C ２０ Heterocycloalkyl, optionally substituted C ６ -C １０ Aryl, optionally substituted C ２ -C ９ independently selected from heteroaryls, polyamides, and polyethers; A compound or a salt thereof, wherein n is selected from 2, 3, 4, 5, and 6.

29. R １ The compound of claim 28, wherein is —CN.

30. R １ The compound of claim 28, wherein is —H.

31. R １ But -C(O)-X-R ｚ 29. The compound of claim 28, wherein:

32. R ｚ is optionally substituted C １－１５ The compound of any one of claims 28 to 31, which is alkyl.

33. The compound of any one of claims 28 to 32, wherein X is O.

34. 33. The compound of any one of claims 28 to 32, wherein X is NH.

35. The compound is R １３ , R １４ , R １５ , R １６ , and R １７ The following substituted phenyl groups defined by: 【Chemistry 49】 The compound according to any one of claims 28 to 34, comprising one of:

36. 36. The compound of any one of claims 28 to 35, wherein the compound is a compound of formula VII:

37. 36. The compound of any one of claims 28 to 35, wherein the compound is a compound of formula VIII:

38. Oligomeric or polymeric compounds of formula IX or X: [Transformation 50] or a salt thereof, During the ceremony, each X is independently O or NR'; L is optionally substituted C １ -C ２０ Alkylene, optionally substituted C １ -C ２０ Alkenylene, optionally substituted C ２ -C ２０ Alkynylene, optionally substituted C ２ -C ２０ Alkoxyalkylene, optionally substituted C ２ -C ２０ Cycloalkylene, optionally substituted C ２ -C ２０ Cycloalkenylene, optionally substituted C ２ -C ２０ and heterocycloalkylene, wherein one or more backbone carbon atoms of L are optionally replaced by a divalent group each independently selected from oxygen (—O—), carbonyl (—CO—), optionally substituted alkylamino, optionally substituted cycloalkylene, optionally substituted heterocyclylene, optionally substituted heteroarylene, optionally substituted arylene, polyamide, and polyether; Each R ３ , R ５ , R ６ , R ７ , R ８ , R ９ , R １０ , R １３ , R １４ , R １５ , R １６ , and R １７ is H, halogen, optionally substituted C １ -C ２０ Alkyl, optionally substituted C ２ -C ２０ Alkenyl, optionally substituted C ２ -C ２０ Alkynyl, optionally substituted C ３ -C ８ Cycloalkyl, optionally substituted C ２ -C ２０ Cycloalkenyl, optionally substituted C ２ -C ７ Heterocycloalkyl, optionally substituted C ６ -C １０ Aryl, optionally substituted C ２ -C ９ Heteroaryl, —OR′, —C(O)R′, —C(O)OR′, —C(O)NR′R″, —C(═NR′)NR′R″, —C(═NR″)R′, —NR′R″, —CN, —N═NR′, cyanate, —OCN, —NCO, —NO ２ , -OC(O)NR'R'', -SR', -S-SR', -S(O)R', -S(O) ２ R', -S(O) ２ OR', -S(O) ２ NR', -C(O)SR', -C(S)SR', -C(S)NR', ​​-B(OH) ２ , -B(OR')(OR''),PR' ３ , -PR' ２ , -P(OR') ２ , -OP(OR') ２ , -P(O)(OR') ２ , -OP(O)(OR') ２ , polyamide, and polyether; Each R′ and R″ is H, optionally substituted C １ -C ２０ Alkyl, optionally substituted C １ -C ２０ Alkenyl, optionally substituted C ２ -C ２０ Alkynyl, optionally substituted C ２ -C ２０ Cycloalkyl, optionally substituted C ２ -C ２０ Cycloalkenyl, optionally substituted C ２ -C ２０ Heterocycloalkyl, optionally substituted C ６ -C １０ Aryl, optionally substituted C ２ -C ９ independently selected from heteroaryls, polyamides, and polyethers; A compound or salt thereof, wherein n is at least 2, 3, 4, 5, 10, 20, 100, 150, 300, 500, or 1000 (eg, n is an average degree of polymerization from 5 to 1000 or from 10 to 100).

39. 39. The compound of claim 38, wherein the compound is a homo-oligomer or homopolymer.

40. 40. The compound of claim 38 or 39, wherein the compound is an oligomer or polymer that is a polyether, polyester, polyamide, polycarbonate, polyurethane, polyurea, or polysaccharide.

41. A composition comprising one or more compounds according to any one of claims 17 to 40.

42. The composition of any one of claims 1 to 16 or 41, wherein the composition is a sunscreen.

43. 43. The sunscreen composition of claim 42, further comprising one or more additional components selected from humectants, emollients, preservatives, buffers, chelating agents, fragrances, antioxidants, antimicrobial agents, thickeners, dryness control agents, UV filters, and solvents.

44. 44. A sunscreen composition according to claim 42 or 43, wherein the compound is present in an amount ranging from 0.01% to 50.0% by weight.

45. 43. The sunscreen composition of claim 42, wherein the composition is formulated as a solution, lotion, emulsion, cream, gel, aerosol, or spray.

46. The composition of any one of claims 1 to 16 or 41, wherein the composition is a cosmetic composition.

47. 47. The cosmetic composition of claim 46, wherein the composition is a solution, emulsion, lotion, cream, emulsion, foam, gel, ointment, paste, suspension, stick, powder, wax, tablet, aerosol, or spray.

48. 47. The cosmetic composition of claim 46, wherein the composition is a hair product.

49. 47. The cosmetic composition of claim 46, wherein the composition is formulated for application to the lips.

50. 47. The cosmetic composition of claim 46, wherein the composition is formulated for hair removal.

51. 42. A method of providing UV light protection to the skin or hair of a subject, comprising applying the composition of any one of claims 1 to 16 or 41 to the skin or hair of the subject.

52. 52. The method of claim 51, wherein the composition comprises one or more of compounds E1-E64 of Table 6.

53. 42. A composition stabilized against light-induced degradation according to any one of claims 1 to 16 or 41, further comprising an organic material that is susceptible to light-induced degradation.

54. 54. The composition of claim 53, wherein the organic material is a thermoplastic polymer, a thermosetting polymer, a polyester, a protein, a polysaccharide, an adhesive, or a blend thereof.

55. 54. The composition of claim 53, wherein the organic material is a coating, wax, resin, varnish, lacquer, enamel, or paint.

56. 56. The composition of claim 55, wherein the coating is applied onto a substrate that is sensitive to UV light.

57. 57. The composition of any one of claims 53 to 56, wherein the composition comprises one or more compounds of formula I or formula II in an amount of 0.01% to 50% by weight of the organic material.

58. 58. The composition of any one of claims 53 to 57, wherein the composition comprises one or more compounds selected from compounds E1 to E64 of Table 6.

59. 42. The composition of any one of claims 1 to 16 or 41 formulated to protect fabrics from photodegradation.

60. 42. A method of providing UV light protection to a UV-sensitive material, comprising applying the composition of any one of claims 1 to 16 or 41 to the UV-sensitive material.

61. 61. The method of claim 60, wherein the composition comprises one or more compounds selected from compounds E1 to E64 of Table 6.

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