Freshwater biodegradable water dispersible sulfopolyesters

Abstract

The present application discloses water-dispersible sulfopolyester compositions having glass transition temperatures (Tg) or melting temperatures (Tm) around 50°C. The sulfopolyesters possess optimal water dispersibility and film forming behavior, and are readily freshwater biodegradable. The sulfopolyesters can also have UV light absorbing ability in the UVA and UVB spectrum based on their chemical compositions. The disclosed compositions are useful for hair care applications.

Description

[0001] FRESHWATER BIODEGRADABLE WATER DISPERSIBLE SULFOPOLYESTERS

[0002] BACKGROUND OF THE INVENTION

[0003] Sulfopolyesters are water-dispersible due to the incorporate of ionic groups within the polymer backbone as described in numerous disclosures. Current commercial sulfopolyesters have low freshwater biodegradability. As such, there is a need for freshwater biodegradable water-dispersible sulfopolyesters. Ideally, such freshwater biodegradable water-dispersible sulfopolyesters should have the following characteristics: 1. a glass transition temperature or melting temperature in the range of from 45°C and 70°C; 2. a 60% biodegradability within 28 days according to OECD301 F; 3. Dispersible in water without addition of any agents such as surfactants, at a temperature of less than or equal to 70°C to form a dispersion of at least 5 wt%, while it is not necessary for the dispersion to be clear or have low turbidity; 4. Film forming behavior, i.e., form preferably clear, flexible films from the aqueous dispersion upon drying (evaporation of water) and without the need of addition of other film forming agents or coalescents; and optionally 5. UV light absorption ability in both the UVA (320 to 400 nm) and UVB (280 to 320 nm) spectrums.

[0004] SUMMARY OF THE INVENTION

[0005] The present application discloses a sulfonated co-polyester, comprising the reaction product of:

[0006] (a) 40 to 100 mole % of an acid component, comprising:

[0007] (i) a diacid or derivative chosen from a (C3-8)cycloalkyl dicarboxylic acid or derivative; a (Ce)aryl dicarboxylic acid or derivative; a (C2-3o)alkyl dicarboxylic acid or derivative, wherein the alkyl is unbranched or branched; a (C2-3o)alkenyl dicarboxylic acid or derivative, wherein the alkenyl is unbranched or branched; or a combination thereof,

[0008] (ii) a sulfonated dicarboxylic acid or ester of the formula I:

[0009] I wherein:

[0010] R is hydrogen or (Ci -4)alkyl ;

[0011] M+ is H+, Na+, K+, Li+, or +NH4, and wherein the diacid or derivative is present from 80 mole % to 95 mole %, and the sulfonated dicarboxylic acid or ester is present from 2.5 mole % to 20 mole %, each based on the total moles of the acid component,

[0012] (b) 88 to 99.6 mole % of a diol component, comprising an unbranched or branched (C2-i2)alkyl diol, a (C3-8)cycloalkyl dimethanol, a (cs- 8)cycloalkyl-diol, which is unsubstituted or substituted by 1 to 4 (Ci- 4)alkyl groups; a compound of formula II: H-(OCH2CH2)n-OH II, wherein n is an integer from 2 to 500; or a combination thereof,

[0013] (c) 0 to 60 mole % of an ultraviolet light absorbing component, comprising:

[0014] (i) an ultraviolet light absorbing monocarboxylic acid or ester (“UVMA”) comprising an ultraviolet light absorbing moiety that absorbs light at a wavelength of from 280 to 420 nm, wherein the UVMA is a benzoic acid or ester, a cinnamic acid or ester, a 2-benzoylbenzoic acid or ester, a 3,3-diphenylacrylic acid or ester, or combination thereof, wherein each is unsubstituted or substituted by 1 -4 substituents selected from halo, amino, di(Ci-4)alkylamino, hydroxyl, (Ci- 4)alkoxy, cyano, or (Ci-4)alkyl;

[0015] (ii) an ultraviolet light absorbing dicarboxylic acid or derivative (“UVDA”) comprising an ultraviolet light absorbing moiety that absorbs light at a wavelength of from 280 to 420 nm, wherein the UVDA is a naphthalene dicarboxylic acid or derivative, a 1 ,1 ’-diphenyl dicarboxylic acid or derivative, a phthalic acid or derivative, a 5-amino-isophthalic acid or ester, a 5-(di(Ci - 4)alkylamino)isophthalic acid or ester, a 4,4'-methylenebis(3- hydroxy-2-naphthoic acid) or ester, 2-benzylmalonic acid or ester, a 5,5'-methylenebis(2-aminobenzoic acid) or ester; or

[0016] (iii) a combination thereof,

[0017] (d) 0.4 to 12 mole % of a water dispersing component, comprising a compound of formula III:

[0018] H-(OCH2CH2)n-O(Ci-4)alkyl,

[0019] III wherein n is an integer from 2 to 500, wherein the total mole % of all components is 200 mole %, and the total mole % of the acid component, the UVMA, and the UVDA is 100 mole %, and the total mole % of the diol component, and the water dispersing component is 100 mole %, wherein the total mole % of the water dispersing component and the sulfonated dicarboxylic acid or ester derivative of the formula I is at least 8 mole % based on the total moles of all components, wherein the sulfonated co-polyester is dispersible in water at 70°C to form a dispersion having at least 5 wt% of the sulfonated co-polyester based on the total weight of the dispersion, wherein the sulfonated co-polyester has a glass transition temperature (“Tg”) that is in the range of from -60 to 70°C and a melting point (“Tm”) that is in the range of from 45 to 80°C.

[0020] The present application also discloses compositions made from the sulfonated co-polyesters.

[0021] BRIEF DESCRIPTION OF THE FIGURES

[0022] The present application makes reference to the following figures, wherein: Figure 1 provides UV absorption spectra for Eastman AQ-48 Ultra polymer (“AQ48”) and Example 1.

[0023] Figure 2 provides UV absorption spectra for Eastman AQ-48 Ultra polymer (“AQ48”) and Example 2.

[0024] Figure 3 provides UV absorption spectra for Eastman AQ-48 Ultra polymer (“AQ48”) and Example 3.

[0025] DETAILED DESCRIPTION OF THE INVENTION

[0026] Definitions

[0027] As used herein, the singular forms "a", "an", and "the" include plural referents unless the context clearly dictates otherwise. For example, reference to the reaction product of a diacid and a diol is intended to include the reaction product of one or multiple diacids with one or multiple diols.

[0028] “Polyester” encompasses both homopolyesters and copolyesters and means a synthetic polymer prepared by the polycondensation of difunctional carboxylic acids with difunctional hydroxyl compound. As used herein, the term “sulfonated co-polyester” or "sulfopolyester" means any polyester comprising a sulfomonomer. A sulfomonomer is a compound that is sulfonated. A sulfomonomer can be either a difunctional carboxylic acid or dicarboxylic acid, a monocarboxylic acid or a diol, also a mono-alcohol. Typically, the difunctional carboxylic acid is a dicarboxylic acid and the difunctional hydroxyl compound is a dihydric alcohol such as, for example glycols and dials. The term "residue", as used herein, means any organic structure incorporated into the polymer through a polycondensation reaction involving the corresponding monomer. Thus, the dicarboxylic acid residue may be derived from a dicarboxylic acid monomer or its associated acid halides, esters, salts, anhydrides, or mixtures thereof. As used herein, therefore, the term dicarboxylic acid is intended to include dicarboxylic acids and any derivative of a dicarboxylic acid, including its associated acid halides, esters, half-esters, salts, half-salts, anhydrides, mixed anhydrides, or mixtures thereof, useful in a polycondensation process with a dial to make a high molecular weight polyester. “Acid component” means the residues derived from a diacid, ester, or anhydride derivative.

[0029] “Diacid or derivative” means a compound having two carboxylic acids, a carboxylic acid and an ester moiety, two ester moieties, or an anhydride.

[0030] “Dicarboxylic acid or derivative” means a compound having two carboxylic acids, a carboxylic acid and an ester moiety, two ester moieties, or an anhydride. Dicarboxylic acid or derivative does not encompass sulfonated derivatives.

[0031] “Sulfonated dicarboxylic acid or ester” means a dicarboxylic acid or ester derivative that is further sulfonated.

[0032] “Diol component” means the residues of the sulfopolyester derived from a compound having two alcohol groups.

[0033] “Ultraviolet light absorbing component” or ULAC means the residues of the sulfopolyester derived from a compound that absorbs ultraviolet light at a specified wavelength. The ULAC can be derived from a monocarboxylic acid or ester derivative, a dicarboxylic acid or derivative, a monodiol, or a diol. The ULAC is incorporated into the sulfopolyester by the typical polycondensation reaction used to make polyesters.

[0034] “Ultraviolet light absorbing monocarboxylic acid or derivative” or UVMA is a ULAC having one carboxylic acid or ester moiety. The UVMA absorbs ultraviolet light at a specified wavelength.

[0035] “Ultraviolet light absorbing dicarboxylic acid or ester derivative” or UVDA is a ULAC having two carboxylic acids, ester, or anydride moieties. The UVDA absorbs ultraviolet light at a specified wavelength.

[0036] “Ultraviolet light absorbing monodiol” or UVMD is a ULAC comprising one alcohol moiety that absorbs ultraviolet light at a specified wavelength.

[0037] “Water dispersing component” means a residue derived from a monoalkyl substituted polyethylene glyol.

[0038] “Cycloalkyl” means a cyclohydrocarbon. The cycloalkyl group can be further identified by the number of carbon atoms in the ring, which is three or more carbons (e.g., (C3-6)). “Cycloalkyl dicarboxylic acid or ester” means a cycloalkyl having either two carboxylic acid moieties, one carboxylic acid and one ester moiety, or two ester moieties.

[0039] “Alkylene” or “alkyl” means a hydrocarbon compound. The alkylene or alkyl group can further be defined by the number of carbons (e.g., (C1-10)). The alkylene group can be unbranched or branched. Typically an alkyl is terminal while an alkylenyl is non-terminal. Nonlimiting examples of alkylene include butyl, methyl, hexyl, and the like.

[0040] “Alkenyl” is an alkylene or alkyl with at least one unsaturated carboncarbon bond.

[0041] “Aryl” means an aromatic hydrocarbyl ring system.

[0042] “Aryl dicarboxylic acid or derivative” means an aryl having two carboxylic acid moieties, one carboxylic acid and one ester moieties, two ester moieties, or an anhydride moiety.

[0043] “Alkyl dicarboxylic acid or derivative” means an alkyl with two carboxylic acid moieties, one carboxylic acid and one ester moieties, two ester groups, or an anhydride moiety.

[0044] “Alkenyl dicarboxylic acid or derivative” means an alkenyl with two carboxylic acid moieties, one carboxylic acid and one ester moieties, two ester moieties, or an anhydride moiety.

[0045] “Diol” means a compound having two alcohol groups.

[0046] “Alkylene diol” means an alkylene with two alcohol groups.

[0047] “Cycloalkyl dimethanol” means a cycloalkyl group with two dimethanol substituents.

[0048] “Derivative” as used in the context of this disclosure means a compound that is derived from a carboxylic acid such as an ester and anhydride.

[0049] Compositions

[0050] The present application discloses a sulfonated co-polyester, comprising the reaction product of: (a) 40 to 100 mole % of an acid component, comprising: (i) a diacid or derivative chosen from a (C3- 8)cycloalkyl dicarboxylic acid or derivative; a (Ce)aryl dicarboxylic acid or derivative; a (C2-3o)alkyl dicarboxylic acid or derivative, wherein the alkyl is unbranched or branched; a (C2-3o)alkenyl dicarboxylic acid or derivative, wherein the alkenyl is unbranched or branched; or a combination thereof, (ii) a sulfonated dicarboxylic acid or ester of the formula I:1wherein: R is hydrogen or (Ci-4)alkyl; R1is i_°(C1-4)aikyior ■anc| M+ jSH+, Na+, K+, Li+, or+NH4, and wherein the diacid or derivative is present from 80 mole % to 95 mole %, and the sulfonated dicarboxylic acid or ester is present from 2.5 mole % to 20 mole %, each based on the total moles of the acid component, (b) 88 to 99.6 mole % of a diol component, comprising an unbranched or branched (C2-i2)alkyl diol, a (C3-8)cycloalkyl dimethanol, a (cs- 8)cycloalkyl-diol, which is unsubstituted or substituted by 1 to 4 (C1 -4)alkyl groups; a compound of formula II: H-(OCH2CH2)n-OH II, wherein n is an integer from 2 to 500; or a combination thereof, (c) 0 to 60 mole % of an ultraviolet light absorbing component, comprising: (i) an ultraviolet light absorbing monocarboxylic acid or ester (“UVMA”) comprising an ultraviolet light absorbing moiety that absorbs light at a wavelength of from 280 to 420 nm, wherein the UVMA is a benzoic acid or ester, a cinnamic acid or ester, a 2-benzoylbenzoic acid or ester, a 3,3-diphenylacrylic acid or ester, or combination thereof, wherein each is unsubstituted or substituted by 1 -4 substituents selected from halo, amino, di(Ci-4)alkylamino, hydroxyl, (Ci- 4)alkoxy, cyano, or (Ci-4)alkyl; (ii) an ultraviolet light absorbing dicarboxylic acid or derivative (“UVDA”) comprising an ultraviolet light absorbing moiety that absorbs light at a wavelength of from 280 to 420 nm, wherein the UVDA is a naphthalene dicarboxylic acid or derivative, a 1 ,1 ’-diphenyl dicarboxylic acid or derivative, a phthalic acid or derivative, a 5-amino-isophthalic acid or ester, a 5-(di(Ci-4)alkylamino)isophthalic acid or ester, a 4,4'-methylenebis(3- hydroxy-2-naphthoic acid) or ester, 2-benzylmalonic acid or ester, a 5,5'- methylenebis(2-aminobenzoic acid) or ester; or (iv) a combination thereof, (d) 0.4 to 12 mole % of a water dispersing component, comprising a compound of formula III: H-(OCH2CH2)n-O(Ci-4)alkyl III, wherein n is an integer from 2 to 500, wherein the total mole % of all components is 200 mole %, and the total mole % of the acid component, the UVMA, and the UVDA is 100 mole %, and the total mole % of the diol component, and the water dispersing component is 100 mole %, wherein the total mole % of the water dispersing component and the sulfonated dicarboxylic acid or ester derivative of the formula I is at least 8 mole % based on the total moles of all components, wherein the sulfonated co-polyester is dispersible in water at 70°C to form a dispersion having at least 5 wt% of the sulfonated co-polyester based on the total weight of the dispersion, wherein the sulfonated co-polyester has a glass transition temperature (“Tg”) that is in the range of from -60 to 70°C and a melting point (“Tm”) that is in the range of from 45 to 80°C. In one embodiment or in combination with any other embodiment, the sulfonated co-polyester is dispersible in water at 50°C to form a dispersion having at least 5 wt% of the sulfonated co-polyester based on the total weight of the dispersion.

[0051] In one embodiment or in combination with any other embodiment, the acid component is present at from 40 to 100 mole%, or from 50 to 100 mole%, or from 60 to 100 mole%, or from 70 to 100 mole%, or from 80 to 100 mole%, or from 90 to 100 mole%, or 40 to 90 mole%, or from 50 to 90 mole%, or from 60 to 90 mole%, 70 to 90 mole%, 80 to 90 mole%, or 40 to 80 mole%, or from 50 to 80 mole%, or from 60 to 80 mole%, or from 70 to 80 mole%, or 40 to 70 mole%, or from 50 to 70 mole%, or from 60 to 70 mole%, or 40 to 60 mole%, or from 50 to 60 mole%, or 40 to 50 mole%.

[0052] In one embodiment or in combination with any other embodiment, the diol component is present at from 88 to 99.6 mole%, or from 88 to 95 mole%, or from 88 to 90 mole%, or from 90 to 99.6 mole%, or from 90 to 95 mole%, or from 95 to 99.6 mole%.

[0053] In one embodiment or in combination with any other embodiment, the ultraviolet light absorbing component is present at from 0 to 60 mole%, or from 0 to 50 mole%, or from 0 to 40 mole%, or from 0 to 30 mole%, or from 0 to 20 mole%, or from 0 to 10 mole%, or from 1 to 60 mole%, or from 1 to 50 mole%, or from 1 to 40 mole%, or from 1 to 30 mole%, or from 1 to 20 mole%, or from 1 to 10 mole%, or from 5 to 60 mole%, or from 5 to 50 mole%, or from 5 to 40 mole%, or from 5 to 30 mole%, or from 5 to 20 mole%, or from 5 to 10 mole%, or from 10 to 60 mole%, or from 10 to 50 mole%, or from 10 to 40 mole%, or from 10 to 30 mole%, or from 10 to 20 mole%, or from 20 to 60 mole%, or from 20 to 50 mole%, or from 20 to 40 mole%, or from 20 to 30 mole%, or from 30 to 60 mole%, or from 30 to 50 mole%, or from 30 to 40 mole%, or from 40 to 60 mole%, or from 40 to 50 mole%, or from 50 to 60 mole%.

[0054] In on embodiment or in combination with any other embodiment, the water dispersing component is from 0.4 to 12 mole%, or from 0.4 to 10 mole%, or from 0.4 to 5 mole%, or from 0.4 to 2.5 mole%, or from 0.4 to 1 mole%, or 1 to 12 mole%, or from 1 to 10 mole%, or from 1 to 5 mole%, or from 1 to 2.5 mole%, or 2.5 to 12 mole%, or from 2.5 to 10 mole%, or from 2.5 to 5 mole%, or 5 to 12 mole%, or from 5 to 10 mole%, or 10 to 12 mole%.

[0055] In one embodiment or in combination with any other embodiment, wherein (i) the diacid or derivative is a (C3-8)cycloalkyl dicarboxylic acid or derivative.

[0056] In one embodiment or in combination with any other embodiment, wherein (i) the diacid or derivative is a a (Ce)aryl dicarboxylic acid or derivative.

[0057] In one embodiment or in combination with any other embodiment, wherein (i) the diacid or derivative is a (C2-3o)alkyl dicarboxylic acid or derivative, wherein the alkyl is unbranched or branched. In one class of this embodiment, the diacid or derivative is a (C2-e)alkyl dicarboxylic acid or derivative. In one subclass of this class, the diacid or derivative is adipic acid or derivative.

[0058] In one embodiment or in combination with any other embodiment, wherein (i) the diacid or derivative is a (C2-3o)alkenyl dicarboxylic acid or derivative, wherein the alkenyl is unbranched or branched. In one embodiment or in combination with any other embodiment, the diacid or derivative is present from 80 to 90 mole%, or from 80 to 85 mole%, or from 85 to 95 mole%, or from 85 to 90 mole%, or from 90 to 95 mole%.

[0059] In one embodiment or in combination with any other embodiment, R is hydrogen.

[0060] In one embodiment or in combination with any other embodiment, R is (Ci-4)alkyl. In one class of this embodiment, the (Ci-4)alkyl is methyl, ethyl, propyl, butyl, isobutyl, or isopropyl.

[0061] In one embodiment or in combination with any other embodiment, R1is H C-^alkyl

[0062] In one embodiment or in combination with any other embodiment, R1, and M+is H+, Na+, K+, Li+, or+NH4. In one class of this embodiment, M+ is H+. In one class of this embodiment, M+ is Na+. In one class of this embodiment, M+ is K+. In one class of this embodiment, M+ is Li+. In one class of this embodiment, M+ is +NH4.

[0063] In one embodiment or in combination with any other embodiment, the sulfonated dicarboxylic acid or ester is present from 2.5 to 20 mole%, or from 2.5 to 15 mole%, or from 2.5 to 10 mole%, or from 2.5 to 5 mole%, or from 5 to 20 mole%, or from 5 to 15 mole%, or from 5 to 10 mole%, or from 10 to 20 mole%, or from 10 to 15 mole%, or from 15 to 20 mole%.

[0064] In one embodiment or in combination with any other embodiment, the diol component is an unbranched or branched (C2-i2)alkyl diol or a compound of formula II, wherein n is an integer from 2 to 500; or a combination thereof. In one embodiment or in combination with any other embodiment, the diol component is an unbranched or branched (C2-i2)alkyl diol. In one embodiment or in combination with any other embodiment, the diol component is a (C3- 8)cycloalkyl dimethanol. In one embodiment or in combination with any other embodiment, the diol component is a (c3-8)cycloalkyl-diol, which is unsubstituted or substituted by 1 to 4 (Ci -4)alkyl groups. In one embodiment or in combination with any other embodiment, the diol component is a compound of formula II: H-(OCH2CH2)n-OH II, wherein n is an integer from 2 to 500. In one class of this embodiment, n is an integer from 2 to 400, or from 2 to 300, or from 2 to 200, or from 2 to 100, or from 2 to 75, or from 2 to 50, or from 2 to 25, or from 2 to 15, or from 15 to 400, or from 15 to 300, or from 15 to 200, or from 15 to 100, or from 15 to 75, or from 15 to 50, or from 15 to 25, from 25 to 400, or from 25 to 300, or from 25 to 200, or from 25 to 100, or from 25 to 75, or from 25 to 50, or from 50 to 400, or from 50 to 300, or from 50 to 200, or from 50 to 100, or 50 to 75, or 75 to 400, or 75 to 300, or 75 to 200, or 75 to 100, or from 100 to 400, or from 100 to 300, or from 100 to 200, or from 200 to 400, or from 200 to 300, or from 300 to 400. In one embodiment or in combination with any other embodiment, the UVMA is a benzoic acid or ester, unsubstituted or substituted by 1 -4 substituents selected from halo, amino, di(Ci-4)alkylamino, hydroxyl, (Ci-4)alkoxy, cyano, or (Ci-4)alkyl. In one embodiment or in combination with any other embodiment, the UVMA is a cinnamic acid or ester, unsubstituted or substituted by 1-4 substituents selected from halo, amino, di(Ci-4)alkylamino, hydroxyl, (Ci-4)alkoxy, cyano, or (Ci -4)al kyl. In one embodiment or in combination with any other embodiment, the UVMA is a 2-benzoylbenzoic acid or ester, unsubstituted or substituted by 1 -4 substituents selected from halo, amino, di(Ci-4)alkylamino, hydroxyl, (Ci- 4)alkoxy, cyano, or (Ci-4)alkyl . In one embodiment or in combination with any other embodiment, the UVMA is a 3,3-diphenylacrylic acid or ester, unsubstituted or substituted by 1 -4 substituents selected from halo, amino, di(Ci-4)alkylamino, hydroxyl, (Ci-4)alkoxy, cyano, or (Ci-4)alkyl.

[0065] In one embodiment or in combination with any other embodiment, the UVDA is a naphthalene dicarboxylic acid or derivative,

[0066] In one embodiment or in combination with any other embodiment, the UVDA is a 1 ,1 ’-diphenyl dicarboxylic acid or derivative. In one embodiment or in combination with any other embodiment, the UVDA is a phthalic acid or derivative. In one embodiment or in combination with any other embodiment, the UVDA is a 5-amino-isophthalic acid or ester. In one embodiment or in combination with any other embodiment, the UVDA is a 5-(di(Ci - 4)alkylamino)isophthalic acid or ester. In one embodiment or in combination with any other embodiment, the UVDA is a 4,4'-methylenebis(3-hydroxy-2- naphthoic acid) or ester. In one embodiment or in combination with any other embodiment, the UVDA is 2-benzylmalonic acid or ester. In one embodiment or in combination with any other embodiment, the UVDA is a 5,5'- methylenebis(2-aminobenzoic acid) or ester.

[0067] In one embodiment or in combination with any other embodiment, the water dispersing component comprises a compound of formula III: H- (OCH2CH2)n-O(Ci-4)alkyl (III), wherein n is an integer from 2 to 500, or from 2 to 400, or from 2 to 300, or from 2 to 200, or from 2 to 100, or from 2 to 75, or from 2 to 50, or from 2 to 25, or from 2 to 15, or from 15 to 400, or from 15 to 300, or from 15 to 200, or from 15 to 100, or from 15 to 75, or from 15 to 50, or from 15 to 25, from 25 to 400, or from 25 to 300, or from 25 to 200, or from 25 to 100, or from 25 to 75, or from 25 to 50, or from 50 to 400, or from 50 to 300, or from 50 to 200, or from 50 to 100, or 50 to 75, or 75 to 400, or 75 to 300, or 75 to 200, or 75 to 100, or from 100 to 400, or from 100 to 300, or from 100 to 200, or from 200 to 400, or from 200 to 300, or from 300 to 400.

[0068] In one class of this embodiment, the (Ci-4)alkyl moiety in the compound of formula III is a methyl, ethyl, propyl, isopropyl, n-butyl, or isobutyl. In a subclass of this class, (Ci-4)alkyl moiety in the compound of formula III is a methyl. In a subclass of this class, (Ci -4)alkyl moiety in the compound of formula III is a ethyl. In a subclass of this class, (Ci -4)alkyl moiety in the compound of formula III is a propyl. In a subclass of this class, (Ci-4)alkyl moiety in the compound of formula III is a n-butyl.

[0069] In one embodiment or in combination with any other embodiment, the sulfonated co-polyester is dispersible in water at 70°C to form a dispersion having at least 5 wt%, or at least 6 wt%, or at least 7 wt%, or at least 8 wt%, or at least 9 wt%, or at least 10 wt%, or at least 15 wt%, or at least 20 wt%, or at least 25 wt%, or at least 30 wt% of the sulfonated co-polyester based on the total weight of the dispersion.

[0070] In one embodiment or in combination with any other embodiment, the sulfonated co-polyester has a glass transition temperature (“Tg”) that is in the range of from -60 to 70°C, or from -60 to 50°C, or from -60 to 30°C, or from - 60 to 10°C, or from -60 to 0°C, or from -60 to -10°C, or from -60 to -30°C, or from -60 to -50°C, or -40 to 70°C, or from -40 to 50°C, or from -40 to 30°C, or from -40 to 10°C, or from -40 to 0°C, or from -40 to -10°C, or from -40 to - 30°C, or from -40 to -50°C, or -20 to 70°C, or from -20 to 50°C, or from -20 to 30°C, or from -20 to 10°C, or from -20 to 0°C, or from -20 to -10°C, or from -20 to -30°C, or 0 to 70°C, or from 0 to 50°C, or from 0 to 30°C, or from 0 to 10°C, or 10 to 70°C, or from 10 to 50°C, or from 10 to 30°C, or 20 to 70°C, or from 20 to 50°C, or from 20 to 30°C, or 40 to 70°C, or from 40 to 50°C, 60 to 70°C.

[0071] In one embodiment or in combination with any other embodiment, a melting point (“Tm”) that is in the range of from 45 to 80°C, or from 45 to 70°C, or from 45 to 60°C, or from 45 to 50°C, or from 50 to 80°C, or from 50 to 70°C, or from 50 to 60°C, or 60 to 80°C, or from 60 to 70°C.

[0072] In one embodiment or in combination with any other embodiment, the sulfonated co-polyester is a random polymer.

[0073] In one embodiment or in combination with any other embodiment, the inherent viscosity (“IhV”) is in the range of 0.05 to 0.35 dL / g, or in the range of 0.05 to 0.30 dL / g, or in the range of 0.05 to 0.25 dL / g, or in the range of 0.05 to 0.20 dL / g, or in the range of 0.05 to 0.15 dL / g, or in the range of 0.05 to 0.10 dL / g, or in the range of 0.1 to 0.35 dL / g, or in the range of 0.1 to 0.30 dL / g, or in the range of 0.1 to 0.25 dL / g, or in the range of 0.1 to 0.20 dL / g, or in the range of 0.1 to 0.15 dL / g, or in the range of 0.15 to 0.35 dL / g, or in the range of 0.15 to 0.30 dL / g, or in the range of 0.15 to 0.25 dL / g, or in the range of 0.15 to 0.20 dL / g, or in the range of 0.2 to 0.35 dL / g, or in the range of 0.2 to 0.30 dL / g, or in the range of 0.2 to 0.25 dL / g, or in the range of 0.25 to 0.35 dL / g, or in the range of 0.25 to 0.30 dL / g, or in the range of 0.3 to 0.35 dL / g as determined in a 60 / 40 parts by weight solution of phenol / tetrachlorethane at 25°C and at a concentration of about 0.5 g of sulfonated co-polyester in 100 mL of the solution of phenol / tetrachloroethane.

[0074] In one embodiment or in combination with any other embodiment, the sulfonated co-polyester further comprises a branching component, comprising: (i) a branching polycarboxylic acid. In one embodiment or in combination with any other embodiment, the sulfonated co-polyester further comprises a branching component, comprising: (ii) a branching polyol. In one embodiment or in combination with any other embodiment, the sulfonated copolyester further comprises a branching component, comprising: (iii) a branching polyfunctional compound.

[0075] In one embodiment or in combination with any other embodiment, the branching component is present at from 0.05 to 4 mole %, or from 0.05 to 3.5 mole%, or from 0.05 to 3.0 mole%, or from 0.05 to 2.5 mole%, or from 0.05 to 2.0 mole%, or from 0.05 to 1 .5 mole%, or from 0.05 to 1 .0 mole%, or from 0.05 to 0.5 mole%, or from 0.05 to 0.25 mole%, or from 0.05 to 0.1 mole%, or from 0.1 to 4 mole %, or from 0.1 to 3.5 mole%, or from 0.1 to 3.0 mole%, or from 0.1 to 2.5 mole%, or from 0.1 to 2.0 mole%, or from 0.1 to 1.5 mole%, or from 0.1 to 1.0 mole%, or from 0.1 to 0.5 mole%, or from 0.1 to 0.25 mole%, 0.3 to 4 mole %, or from 0.3 to 3.5 mole%, or from 0.3 to 3.0 mole%, or from 0.3 to 2.5 mole%, or from 0.3 to 2.0 mole%, or from 0.3 to 1 .5 mole%, or from 0.3 to 1 .0 mole%, or from 0.3 to 0.5 mole%, 0.5 to 4 mole %, or from 0.5 to 3.5 mole%, or from 0.5 to 3.0 mole%, or from 0.5 to 2.5 mole%, or from 0.5 to 2.0 mole%, or from 0.5 to 1 .5 mole%, or from 0.5 to 1 .0 mole%, or from 1 to 4 mole %, or from 1 to 3.5 mole%, or from 1 to 3.0 mole%, or from 1 to 2.5 mole%, or from 1 to 2.0 mole%, or from 1 to 1 .5 mole%, or 2 to 4 mole %, or from 2 to 3.5 mole%, or from 2 to 3.0 mole%, or from 2 to 2.5 mole%, or from 3 to 4 mole %, or from 3 to 3.5 mole%.

[0076] In one embodiment or in combination with any other embodiment, the branching polyol is 1 ,1 ,1 -trimethylol propane, 1 ,1 ,1 -trimethylolethane, glycerin, pentaerythritol, erythritol, threitol, dipentaerythritol, sorbitol, or combinations thereof; wherein the branching polycarboxylic acid is trimellitic anhydride, pyromellitic dianhydride, or combinations thereof; and wherein the branching polyfunctional compound is dimethylol propionic acid.

[0077] In one embodiment or in combination with any other embodiment, wherein sulfonated co-polyester exhibits a biodegradability of from 10-100%, or from 10-90%, or from 10-80%, or from 10-70%, or from 10-60%, or from 10-50%, or from 10-40%, or from 20-100%, or from 20-90%, or from 20-80%, or from 20-70%, or from 20-60%, or from 20-50%, or from 20-40%, or from 30-100%, or from 30-90%, or from 30-80%, or from 30-70%, or from 30-60%, or from 30-50%, or from 40-100%, or from 40-90%, or from 40-80%, or from 40-70%, or from 40-60%, or from 40-50%, or from 50-100%, or from 50-90%, or from 50-80%, or from 50-70%, or from 50-60%, or from 60-100%, or from 60-90%, or from 60-80%, or from 60-70%, or from 70-100%, or from 70-90%, or from 70-80%, or from 80-100%, or from 80-90%, at 56 days according to the OECD 301 F test method. In one embodiment or in combination with any other embodiment, wherein sulfonated co-polyester exhibits at least 10% biodegradability, or at least 15% biodegradability, or at least 20% biodegradability, or at least 30% biodegradability, or at least 40% biodegradability, at least 45% biodegradability, or at least 50% biodegradability, or at least 55% biodegradability, at least 60% biodegradability, or at least 65% biodegradability, or at least 70% biodegradability, or at least 75% biodegradability, or at least 80% biodegradability, or at least 85% biodegradability, at 56 days according to the OECD 301 F test method.

[0078] In one embodiment or in combination with any other embodiment, the compound of formula III is present at from 0.4 to 10 mole% or 0.4 to 8 mole%, or 0.4 to 6 mole%, or 0.4 to 4 mole%, or 0.4 to 2 mole%, or 0.4 to 1 mole%, or 1 to 12 mole%, or 1 to 10 mole%, or 1 to 8 mole%, or 1 to 6 mole%, or 1 to 4 mole%, or 1 to 4 mole%, or 1 to 2 mole%, or 2 to 12 mole%, or 2 to 10 mole%, or 2 to 8 mole%, or 2 to 6 mole%, or 2 to 4 mole%, or 4 to 12 mole%, or 4 to 10 mole%, or 4 to 8 mole%, or 4 to 6 mole%, or 6 to 12 mole%, or 6 to 10 mole%, or 6 to 8 mole%, or 8 to 12 mole%, or 8 to 10 mole%, or 10 to 12 mole%. In one class of this embodiment, the compound of formula III is the compound of formula Illa:

[0079] H-(OCH2CH2)n-OCH3,

[0080] Illa wherein n is an integer from 2-500.

[0081] In one class of this embodiment, the compound of formula III is the compound of formula lllb:

[0082] H-(OCH2CH2)n-OCH2CH3, lllb wherein n is an integer from 2-500.

[0083] The present application also discloses a compositions comprising any of the previously disclosed sulfonated co-polyesters.

[0084] In one embodiment or in combination with any other embodiment, the sulfonate co-polyester is a sulfonated co-polyester, comprising the reaction product of: (a) 40 to 100 mole % of an acid component, comprising: (i) a diacid or derivative chosen from a (C3-8)cycloalkyl dicarboxylic acid or derivative; a (Ce)aryl dicarboxylic acid or derivative; a (C2-3o)alkyl dicarboxylic acid or derivative, wherein the alkyl is unbranched or branched; a (C2. 3o)alkenyl dicarboxylic acid or derivative, wherein the alkenyl is unbranched or branched; or a combination thereof, (ii) a sulfonated dicarboxylic acid or ester of the formula I:1, wherein: R is hydrogen or (Ci-4)alkyl; R1is wherein the diacid or derivative is present from 80 mole % to 95 mole %, and the sulfonated dicarboxylic acid or ester is present from 2.5 mole % to 20 mole %, each based on the total moles of the acid component, (b) 88 to 99.6 mole % of a diol component, comprising an unbranched or branched (C2-i2)alkyl diol, a (C3-8)cycloalkyl dimethanol, a (c3-8)cycloalkyl-diol, which is unsubstituted or substituted by 1 to 4 (C1 -4)alkyl groups; a compound of formula II: H- (OCH2CH2)n-OH II, wherein n is an integer from 2 to 500; or a combination thereof, (c) 0 to 60 mole % of an ultraviolet light absorbing component, comprising: (i) an ultraviolet light absorbing monocarboxylic acid or ester (“UVMA”) comprising an ultraviolet light absorbing moiety that absorbs light at a wavelength of from 280 to 420 nm, wherein the UVMA is a benzoic acid or ester, a cinnamic acid or ester, a 2-benzoylbenzoic acid or ester, a 3,3- diphenylacrylic acid or ester, or combination thereof, wherein each is unsubstituted or substituted by 1 -4 substituents selected from halo, amino, di(Ci-4)alkylamino, hydroxyl, (Ci-4)alkoxy, cyano, or (Ci-4)alkyl; (ii) an ultraviolet light absorbing dicarboxylic acid or derivative (“UVDA”) comprising an ultraviolet light absorbing moiety that absorbs light at a wavelength of from 280 to 420 nm, wherein the UVDA is a naphthalene dicarboxylic acid or derivative, a 1 ,1 ’-diphenyl dicarboxylic acid or derivative, a phthalic acid or derivative, a 5-amino-isophthalic acid or ester, a 5-(di(Ci - 4)alkylamino)isophthalic acid or ester, a 4,4'-methylenebis(3-hydroxy-2- naphthoic acid) or ester, 2-benzylmalonic acid or ester, a 5,5'-methylenebis(2- aminobenzoic acid) or ester; or (iv) a combination thereof, (d) 0.4 to 12 mole % of a water dispersing component, comprising a compound of formula III: H- (OCH2CH2)n-O(Ci-4)alkyl III, wherein n is an integer from 2 to 500, wherein the total mole % of all components is 200 mole %, and the total mole % of the acid component, the UVMA, and the UVDA is 100 mole %, and the total mole % of the diol component, and the water dispersing component is 100 mole %, wherein the total mole % of the water dispersing component and the sulfonated dicarboxylic acid or ester derivative of the formula I is at least 8 mole % based on the total moles of all components, wherein the sulfonated co-polyester is dispersible in water at 70°C to form a dispersion having at least 5 wt% of the sulfonated co-polyester based on the total weight of the dispersion, wherein the sulfonated co-polyester has a glass transition temperature (“Tg”) that is in the range of from -60 to 70°C and a melting point (“Tm”) that is in the range of from 45 to 80°C.

[0085] In one embodiment or in combination with any other embodiment disclosed herein, the composition is a cosmetic or a personal care product. In one class of this embodiment, the cosmetic or personal care product is a mascara product, or a hair product. Specific Embodiments

[0086] Embodiment 1 . A sulfonated co-polyester, comprising the reaction product of:

[0087] (a) 40 to 100 mole % of an acid component, comprising:

[0088] (i) a diacid or derivative that is chosen from a (C3-8)cycloalkyl dicarboxylic acid or derivative; a (Ce)aryl dicarboxylic acid or derivative; a (C2-3o)alkyl dicarboxylic acid or derivative, wherein the alkyl is unbranched or branched; a (C2-3o)alkenyl dicarboxylic acid or derivative, wherein the alkenyl is unbranched or branched; or a combination thereof,

[0089] (ii) a sulfonated dicarboxylic acid or ester of the formula I:

[0090] I wherein:

[0091] R is hydrogen or (Ci-4)alkyl;

[0092] M+is H+, Na+, K+, Li+, or+NH4, and wherein the diacid or derivative is present from 80 to 95 mole %, and the sulfonated dicarboxylic acid or ester is present from 2.5 to 20 mole %, each based on the total moles of the acid component,

[0093] (b) 88 to 99.6 mole % of a diol component, comprising an unbranched or branched (C2-i2)alkyl diol, a (C3-8)cycloalkyl dimethanol, a (cs- 8)cycloalkyl-diol, which is unsubstituted or substituted by 1 to 4 (Ci- 4)alkyl groups; a compound of formula II: H-(OCH2CH2)n-OH II, wherein n is an integer from 2 to 500; or a combination thereof,

[0094] (c) 0 to 60 mole % of an ultraviolet light absorbing component, comprising: (i) an ultraviolet light absorbing monocarboxylic acid or ester (“UVMA”) comprising an ultraviolet light absorbing moiety that absorbs light at a wavelength of from 280 to 420 nm, wherein the UVMA is a benzoic acid or ester, a cinnamic acid or ester, a 2-benzoylbenzoic acid or ester, a 3,3-diphenylacrylic acid or ester, or combination thereof, wherein each is unsubstituted or substituted by 1 -4 substituents selected from halo, amino, di(Ci-4)alkylamino, hydroxyl, (Ci- 4)alkoxy, cyano, or (Ci-4)alkyl;

[0095] (ii) an ultraviolet light absorbing dicarboxylic acid or derivative (“UVDA”) comprising an ultraviolet light absorbing moiety that absorbs light at a wavelength of from 280 to 420 nm, wherein the UVDA is a naphthalene dicarboxylic acid or derivative, a 1 ,1 ’-diphenyl dicarboxylic acid or derivative, a phthalic acid or derivative, a 5-amino-isophthalic acid or ester, a 5-(di(Ci - 4)alkylamino)isophthalic acid or ester, a 4,4'-methylenebis(3- hydroxy-2-naphthoic acid) or ester, 2-benzylmalonic acid or ester, a 5,5'-methylenebis(2-aminobenzoic acid) or ester; or

[0096] (iii) a combination thereof,

[0097] (d) 0.4 to 12 mole % of a water dispersing component, comprising a compound of formula III:

[0098] H-(OCH2CH2)n-O(Ci-4)alkyl,

[0099] III wherein n is an integer from 2 to 500, wherein the total mole % of all components is 200 mole %, and the total mole % of the acid component, the UVMA, and the UVDA is 100 mole %, and the total mole % of the diol component, and the water dispersing component is 100 mole %, wherein the total mole % of the water dispersing component and the sulfonated dicarboxylic acid or ester derivative of the formula I is at least 8 mole % based on the total moles of all components, wherein the sulfonated co-polyester is dispersible in water at 70°C to form a dispersion having at least 5 wt% of the sulfonated co-polyester based on the total weight of the dispersion, wherein the sulfonated co-polyester has a glass transition temperature (“Tg”) that is in the range of from -60 to 70°C and a melting point (“Tm”) that is in the range of from 45 to 80°C.

[0100] Embodiment 2. The sulfonated co-polyester of Embodiment 1 , wherein the sulfonated co-polyester is a random polymer.

[0101] Embodiment 3. The sulfonated co-polyester of any one of Embodiments 1 or 2, wherein the inherent viscosity (“I hV”) is in the range of 0.05 to 0.35 dL / g, as determined in a 60 / 40 parts by weight solution of phenol / tetrachlorethane at 25°C and at a concentration of about 0.5 g of sulfonated co-polyester in 100 mL of the solution of phenol / tetrachloroethane.

[0102] Embodiment 4. The sulfonated co-polyester of any one of Embodiments 1 -3, wherein the sulfonated co-polyester further comprises a branching component, comprising: (i) a branching polycarboxylic acid; (ii) a branching polyol; (iii) a branching polyfunctional compound; or (iv) a combination thereof.

[0103] Embodiment 5. The sulfonated co-polyester of Embodiment 4, wherein the branching component is present at from 0.05 to 4 mole % based on the total moles of all components.

[0104] Embodiment 6. The sulfonated co-polyester of any one of Embodiments 1 -5, wherein the branching polyol is 1 ,1 ,1 -trimethylol propane, 1 ,1 ,1 - trimethylolethane, glycerin, pentaerythritol, erythritol, threitol, dipentaerythritol, sorbitol, or combinations thereof; wherein the branching polycarboxylic acid is trimellitic anhydride, pyromellitic dianhydride, or combinations thereof; and wherein the branching polyfunctional compound is dimethylol propionic acid. Embodiment 7. The sulfonated co-polyester of any one of Embodiments 1 -6, wherein sulfonated co-polyester exhibits at least 10% biodegradability, or at least 15% biodegradability, or at least 20% biodegradability, or at least 30% biodegradability, or at least 40% biodegradability, at least 45% biodegradability, or at least 50% biodegradability, or at least 55% biodegradability, at least 60% biodegradability, or at least 65% biodegradability, or at least 70% biodegradability, or at least 75% biodegradability, or at least 80% biodegradability, or at least 85% biodegradability, at 56 days according to the OECD 301 F test method. Embodiment 8. The sulfonated co-polyester of any one of Embodiments 1 -7, wherein the compound of formula III is present at from 0.4 to 10 mole% or 0.4 to 8 mole%, or 0.4 to 6 mole%, or 0.4 to 4 mole%, or 0.4 to 2 mole%, or 0.4 to 1 mole%, or 1 to 12 mole%, or 1 to 10 mole%, or 1 to 8 mole%, or 1 to 6 mole%, or 1 to 4 mole%, or 1 to 4 mole%, or 1 to 2 mole%, or 2 to 12 mole%, or 2 to 10 mole%, or 2 to 8 mole%, or 2 to 6 mole%, or 2 to 4 mole%, or 4 to 12 mole%, or 4 to 10 mole%, or 4 to 8 mole%, or 4 to 6 mole%, or 6 to 12 mole%, or 6 to 10 mole%, or 6 to 8 mole%, or 8 to 12 mole%, or 8 to 10 mole%, or 10 to 12 mole%.

[0105] Embodiment 9. The sulfonated co-polyester of any one of Embodiments 1 -8, wherein the diol component is an unbranched or branched (C2-12)alkyl diol or a compound of formula II, wherein n is an integer from 2 to 500; or a combination thereof.

[0106] Embodiment 10. The sulfonated co-polyester of Embodiment 9, wherein the diol component comprises an unbranched or branched (C2-i2)alkyl diol. Embodiment 1 1 . The sulfonated co-polyester of Embodiment 9, wherein the diol component comprises or a compound of formula II, wherein n is an integer from 2 to 500.

[0107] Embodiment 12. The sulfonated co-polyester of any one of Embodiments 1 - 1 1 , wherein the diacid component comprises a diacid or derivative that is a (C2-3o)alkyl dicarboxylic acid or derivative.

[0108] Embodiment 13. The sulfonated co-polyester of Embodiment 12, wherein the diacid or derivative is a (C2-e)alkyl dicarboxylic acid or derivative Embodiment 14. The sulfonated co-polyester of Embodiment 13, wherein the diacid or derivative is adipic acid or derivative.

[0109] Embodiment 15. A composition comprising any one of the sulfonated co- polyester of any one of Embodiments 1 -14.

[0110] Embodiment 16. The compositions of Embodiment 15, wherein the composition is a cosmetic or personal care product. Embodiment 17. The composition of Embodiment 16, wherein the cosmetic or personal care product is a mascara product, or a hair product.

[0111] EXPERIMENTAL

[0112] Abbreviations

[0113] D is adipic acid or residue; CL is sodiosulfoisophthalic acid or residue; *G is trans-1 ,4-cyclohexanedicarboxylic acid or residue; G is cis / trans 1 ,4- cyclohexanedicarboxylic acid or residue; T is terephthalic acid; (3) is 1 ,3- propanediol or residue; (4) is 1 ,4-butandiol or residue; (6) is 1 ,6-hexanediol or residue; (mP2k) is polyethylene glycol monomethyl ether of average Mn-2000 or residue; (mP5k) is polyethylene glycol monomethyl ether of average Mn-5000 or residue; (mP0.75k) is polyethylene glycol monomethyl ether of average Mn-750 or residue; (PI k) is polyethylene glycol of average Mn-1000 or residue; M is 2-ethylhexyl 4-methoxycinnamic acid or residue; N is 2,6-naphthalenedicarboxylic acid or residue; min is minute(s); g is gram(s); mol is mole(s); NaAc is sodium acetate; AQ48 is Eastman AQ™ 48 Ultra polymer; nBuOH; rt is room temperature; MeOH is methanol; 2EHOH is 2- ethylhexanol; THE is tetrahydrofuran; rpm is revolutions per minute; Tgis glass transition temperature; d is day(s); UV is ultraviolet; Mwis weight average molecular weight; Da is Dalton; Vac is vacuum; Biodeg is biodegradation; Tmis melting temperature;

[0114] Polymer Characterization

[0115] Compositional analysis by1H NMR

[0116] A polymer sample of 30 mg (± 10 mg) is dissolved in one milliliter of solvent, composed of two-thirds deuterated chloroform and one-third deuterated trifluoroacetic acid. Broker SampleJet NMR tubes are filled with this solution are placed in the autosampler rack. A 400-megahertz Avance II NMR spectrometer with a 9.4 tesla UltraShield Plus magnet (Broker) is used for the analyses. Water dispersibility and dispersion time

[0117] The following procedure is used to determine 5 wt.% water dispersibility and dispersion time of a polymer. Put 285 g of demi water in a glass flask of 500 mL with a magnetic stirrer. Keep magnetic stirrer on throughout the procedure. Heat the flask to 50°C while continuously monitoring the temperature with a thermocouple. Once 50°C is reached, add 15 g of a polymer into the flask and start the timer. Hold the dispersion at 50 °C until the polymer is completely dispersed, i.e. no suspended or precipitated particles of the polymer, and record time required for it. Let the dispersion cool to reach the rt. Should polymer precipitates or not disperse completely, repeat the procedure by reducing the polymer fraction in the mixture.

[0118] Glass transition temperature (Tg) and melting temperature (Tm)

[0119] Tgand Tmof a polymer sample is measured using heat flux differential scanning calorimetry. Measurements are done using a TA Instruments DSC 250 calorimeter. Cooling of the sample cup is achieved by using a TA Instruments RCS-120 air chiller system. Both instruments are controlled using the TRIOS DSC software. The testing is done in a nitrogen gas atmosphere. A flowrate of 50 mL min-1is maintained during the measurement.

[0120] The calorimeter is calibrated using an indium sample of 10 mg before analyzing a polymer sample. A mass of 5 to 15 mg of a polymer is added to an aluminum pan and is sealed. Subsequently, it is then placed in the oven of the calorimeter and the analysis is started. The oven is cooled to -80°C and held at this temperature for 2 min. After equilibration, the temperature in the oven is raised to 300°C at a rate of 20°C min-1. The Tgis determined according to the ASTM D3418 method, and the Tmwas determined by integration of the curve.

[0121] Molecular weight

[0122] Inherent viscosity (IhV)

[0123] IhV of a polyester is a useful parameter to gauge its molecular weight. It is determined by using the following method. The measurements are done using Viscotek Y501 C with Hamilton Microlab 500 autosampler, and data is processed using Malvern ARV software program. Between 0.11 and 0.13 g of a polymer sample weighed in a sample tube, and add 25 mL of phenol- 1 ,1 ,2,2-tetrachloroethane with the dispenser then cover the sample tube with aluminum foil. Add a magnetic stirrer to a sample tube. Subsequently, place the sample in the heating-stirring module at 115°C, for 20 to 25 min. Remove it from the heating block once the polymer is fully dissolved. Filter (0.45 pm Whatman Glass Microfiber) the solution if it looks cloudy. Once the solution is cooled down, cap it with a screw cap and place it in the sample tray for the analysis. While keeping the sample flow time and solvent-blank flow time constant (i.e. constant flowrate), pressure drops across the capillary are measured which are subsequently used to compute IhV (dL g-1) with the following steps.

[0124] Where, AP is pressure drop, Q is flowrate, R is resistance to flow, C is concentration of polymer in a sample, rjreiativerelative viscosity.

[0125] Gel Permeation Chromatography (GPC)

[0126] Number average molecular weight (Mn) and weight average molecular weight (Mw) of a polymer are determined by GPC (Agilent Technologies 1260 Infinity) equipped with a guard column and PLgel 5 pm guard + Mixed C column placed in series. The column temperature is maintained at 25 °C during analysis. 15 mg polymer is dissolved in a 70:30 mass mixture of methylene chloride (CH2CI2) and hexafluoroisopropanol (HFIP) comprising 10 pL of toluene in 10 mL solvent, where toluene is used as a flowrate marker. Sample is filtered through a 0.45 pm Whatman Glass Microfiber filter. The mobile phase (70% CH2CI2 + 30% HFIP; add 5 grams TEA-nitrate per liter) flowrate is set at 1 mL min-1and a variable wavelength detector is set at A = 240 nm. The calibration line was made using Openlab CDS 2.4 GPC software and with 14 polystyrene standards having molecular weights between 580 and 32 200 000 Da.

[0127] UV absorption - Spectrum coverage

[0128] The UV light absorption performance was of a polymer is determined with the following method. A polymer sample is dispersed in demineralized water at mass-based concentration of 300 ppm (± 20 ppm). Subsequently, sample was poured into a quartz cuvette of 1 cm and subjected to UV light in UV7 spectrophotometer Mettler Toledo. UV absorption spectrum is recorded for wavelengths between 250 and 450 nm, which covers both UVB and UVA spectra.

[0129] Biodegradability Test

[0130] The biodegradation test performed is conform to the OECD 301 F guideline, which is a manometric respirometry test to determine readily biodegradation. During this test a solution of the test substance, in a mineral medium, is inoculated with an inoculum and incubated under aerobic conditions in a dark vessel for 28 days. A reference (e.g., sodium benzoate) is also run at the same time to check the operation of the procedures.

[0131] Due to the oxygen (O2) consumption of the oxidation of organic molecules, the O2 uptake can be used to measure the BOD of a substance. Measurements are done with OxiTop respirometer systems which determine a given amount of time at a constant temperature by measuring pressure.

[0132] The pass level for readily biodegradation is 60 % removal of ThOD, the pass value has to be reached within a 10-day window within the 28-day period. Example 1

[0133] A stainless-steel reactor 3.8 L fitted with a stainless-steel stirrer was used for the synthesis. Stainless-steel reactor head, allowed with a nitrogen or vacuum inlet, facilitated the removal of volatile by-products during synthesis. Initially, reactor vessel was charged with dimethyl adipate (D, 265 g, 1 .52 mol), trans- dimethyl 1 ,4-cyclohexanedicarboxylate (*G, 327 g, 1.63 mol), dimethyl-5-sodiosulfoisophthalate (CL, 135 g, 0.46 mol), 1 ,4 butanediol ((4), 336 g, 3.72 mol), polyethylene glycol monomethyl ether of average Mn-2000 ((mP2k), 152 g, 0.08 mol). Titanium tetraisopropoxide solution (2.99% in n- butanol, 22.3 g) was added to provide a catalytic level of 100 ppm elemental titanium based on theoretical polymer yield. Sodium acetate (3.74 g, 0.046 mol) was added to the reactor vessel as a buffer. Reactor vessel was closed and was purged 3 times with nitrogen at rt. The reactor vessel was heated gradually, with an electric heater, to 180°C while continuously stirring at 200 rpm under a gentle nitrogen sweep, and was held at 180°C for 90 min. Thereafter, temperature was increased gradually to 200°C while maintaining the stirring speed with a gentle nitrogen sweep and was held for 80 min. Next, 2-ethylhexyl 4-methoxycinnamate (M, 55 g, 0.19 mol) was added to the reactor vessel followed by raising its temperature to 210°C to for 20 min. In these steps, transesterification was allowed to proceed and as a result of that volatiles (methanol, n-butanol, 2-ethylhexyl alcohol, tetrahydrofuran) were collected. At this point, the temperature was maintained at 210°C, and the nitrogen flow was stopped and was replaced with a vacuum that was gradually ramped down in steps to 3 mbar (± 2 mbar) over the course of 60 min. When full vacuum in place synthesized polymer gradually became more viscous and the agitation speed was decreased from 200 to 100 rpm. Under these conditions the reactor vessel was, first, heated to 220°C and then held at it for 90 min. After cooling to rt, analysis of the polymer yielded the following properties. Composition (mole% for each residue): 48.56*G38.45D4.29M12.99CL93.28(4)2.53(mP2k); Water dispersibility: Yes, 10 wt% in <15 min; Tg: -36°C; Tm: 74oC; IhV 0.18 dL / g; Mw: 12547 Da; Biodegradation in 28 days (average of two): 65.6%. Figure 1 shows the UV spectrum of AQ48 and Ex 1 .

[0134] Example 2

[0135] The same apparatus was used as in Example 1 . Initially, reactor vessel was charged with dimethyl adipate (D, 295 g, 1.71 mol), trans- dimethyl 1 ,4-cyclohexanedicarboxylate fG, 251 g, 1.25 mol), dimethyl 2,6- naphthalenedicarboxylate (N, 46 g, 0.19 mol), dimethyl-5- sodiosulfoisophthalate (CL, 135 g, 0.46 mol), 1 ,4 butanediol ((4), 336 g, 3.72 mol), polyethylene glycol monomethyl ether of average Mn-2000 ((mP2k), 152 g, 0.08 mol). Titanium tetraisopropoxide solution (2.99% in n-butanol, 22.3 g) was added to provide a catalytic level of 100 ppm elemental titanium based on theoretical polymer yield. NaAc (3.74 g, 0.046 mol) was added to the reactor vessel as a buffer. Reactor vessel was closed and was purged 3 times with nitrogen at rt. The reactor vessel was heated gradually, with an electric heater, to 180°C while continuously stirring at 200 rpm under a gentle nitrogen sweep, and was held at 180°C for 90 min. Thereafter, temperature was increased gradually to 200°C while maintaining the stirring speed with a gentle nitrogen sweep and was held for 80 min. Next, 2-ethylhexyl 4- methoxycinnamate (M, 55 g, 0.19 mol) was added to the reactor vessel followed by raising its temperature to 210°C to for 20 min. In these steps, transesterification was allowed to proceed and as a result of that volatiles (methanol, n-butanol, 2-ethylhexyl alcohol, tetrahydrofuran) were collected. At this point, the temperature was maintained at 210°C, and the nitrogen flow was stopped and was replaced with a vacuum that was gradually ramped down in steps to 3 mbar (± 2 mbar) over the course of 60 min. When full vacuum in place synthesized polymer gradually became more viscous and the agitation speed was decreased from 200 to 100 rpm. Under these conditions the reactor vessel was, first, heated to 220°C and then held at it for 90 min. After cooling to rt, analysis of the polymer yielded the following properties. Composition (mole% for each residue): 40.45*G45.8D4.95N4.95M8.8CL88.33(4)6.72(mP2k); Water dispersibility: Yes, 10 wt% in <15 min; Tg: -37°C; Tm: 44°C; IhV 0.17 dL / g; Mw: 7802 Da; Biodegradation in 28 days (average of two): 60.8%. Figure 2 shows UV spectrum of AQ48 and Ex 2.

[0136] Example 3

[0137] The same apparatus was used as in Example 1 . Initially, reactor vessel was charged with dimethyl adipate (D, 285 g, 1 .63 mol), trans- dimethyl 1 ,4- cyclohexanedicarboxylate (*G, 266 g, 1 .33 mol), dimethyl 2,6- naphthalenedicarboxylate (N, 46 g, 0.19 mol), dimethyl-5- sodiosulfoisophthalate (CL, 135 g, 0.46 mol), (4) (318 g, 3.53 mol), (mP0.75k) (86 g, 0.11 mol), (mP2k) (152 g, 0.08 mol), (mP5k) (380 g, 0.08 mol). Titanium tetraisopropoxide solution (2.99% in nBuOH, 22.3 g) was added to provide a catalytic level of 100 ppm elemental titanium based on theoretical polymer yield. NaAc (3.74 g, 0.046 mol) was added to the reactor vessel as a buffer. Reactor vessel was closed and was purged 3x with N2at rt. The reactor vessel was heated gradually, with an electric heater, to 180°C while continuously stirring at 200 rpm under a gentle nitrogen sweep, and was held at 180°C for 90 min. Thereafter, temperature was increased gradually to 200°C while maintaining the stirring speed with a gentle nitrogen sweep and was held for 80 min. Next, 2-ethylhexyl 4-methoxycinnamate (M, 55 g, 0.19 mol) was added to the reactor vessel followed by raising its temperature to 210°C to for 20 min. In these steps, transesterification was allowed to proceed and as a result of that volatiles (MeOH, nBuOH, 2-EHOH, THE) were collected. At this point, the temperature was maintained at 210°C, and the nitrogen flow was stopped and was replaced with a vacuum that was gradually ramped down in steps to 3 mbar (± 2 mbar) over the course of 60 min. When full vacuum in place synthesized polymer gradually became more viscous and the agitation speed was decreased from 200 to 100 rpm. Under these conditions the reactor vessel was, first, heated to 220°C and then held at it for 90 min. After cooling to rt, analysis of the polymer yielded the following properties. Composition (mole% for each residue):

[0138] 42.87*G41 .81 D5.54N4.87M9.78CL87.81 (4)7.32(mP0.75K+mP2k+mPk5); Water dispersibility: Yes, 10 wt% in <15 min; Tg: -55°C; Tm: 48°C; IhV 0.22 dL / g; Mw: 8881 Da; Biodegradation in 28 d (average of two): 76.5%. Figure 3 shows UV spectrum of AQ48 and Ex 3.

[0139] The syntheses of the following sulfonated co-polyesters were conducted in a 500 mL single neck round bottom flask equipped with a stainless-steel stir shaft with a half-moon paddle, glass polymer head and glass side arm to receiver flask for condensate removal.

[0140] For sulfonated co-polyesters synthesized with (4) or (3) a 2-3x excess of the diol was used. The stir rate, time, temperature ramps and vacuum ramps for these materials shown in Table 1 . The polymerization reactions were typically stopped after molecular weight building stopped.

[0141] Table 1.

[0142] Table 2 provides the sulfonated co-polyesters prepared using either diols (4) or (3) along with the mole % of each residue.

[0143] Table 2.

[0144] For (6) or G containing sulfonated co-polyesters, -0.03 molar excess of the diol was used. The stir rate, time, temperature ramps and vacuum ramps for these materials is in Table 3. The polymerization reactions were typically stopped after molecular weight building stopped.

[0145] Table 3: Time, temperature, vacuum and stir rate profile for (6) and G.

[0146] Table 3. Table 4 provides the suflonated-copolyesters prepared from (6) and G.

[0147] Table 4. Formulations of the Sulfonated Co-Polyesters

[0148] Hair fixative gel

[0149] The sulfonated co-polyesters disclosed herein were formulated into hair fixative gels. Formulation procedure

[0150] Initially, a 4wt% dispersion of the sulfonated co-polyester in water is prepared, under continuous stirring at 70°C. The polymer dispersion is cooled down to approximately 40°C and the carbomer thickener is added and mixed using a high-speed mixer, followed by the addition of NaOH to induce gelation. Finally, the preservative is added and the formulation pH is adjusted to approximately 7, using NaOH.

[0151] Table 5. Hair fixative gel formulation recipe (pH 6.5 - 7).

[0152] Table 6. Hair fixative gel formulation recipe (pH 4.5 - 5).

[0153] Curl retention at high humidity

[0154] Procedure

[0155] 2 g / 17 cm Caucasian virgin and bleached straight hair swatches were used for our curl retention studies. The swatches are washed twice with a 10% SLES solution. They are then treated with 0.2 g of formulation per g of hair. While still wet and having previously removed the excess water, the swatches are wrapped around1 / 2-inch Teflon curling rods, taking care to minimize hair overlap. The curling rods are then placed for half an hour in an oven at 80°C and subsequently are left to dry overnight. The dry curls are removed from the rods and are hanged on a peg board, which has measurement markings and subsequently the initial curl length (Lo) is measured. The board with the curls is then placed in a controlled-humidity chamber at 22°C and 90 % RH. The curl length (Lt) is measured at 60, 120, 180, and 300 minutes (n=3). The control is the formulation, which does not include a film former.

[0156] The following formula was used to calculate curl retention where L is the straight hair length. Curl retention (%)=(L-LtL-L0)*100Curl retention %=L-LtL-LO*1 OO

[0157] Table 7. % Curl Retention at high humidity results obtained on virgin hair for the gel formulations under evaluation (n=3).

[0158] Table 8. % Curl Retention at high humidity results obtained on bleached hair for the gel formulations under evaluation (n=3).

[0159] Hair Frizz

[0160] Procedure

[0161] 7g / 20 cm Caucasian virgin straight hair swatches were washed twice with an SLES 10% solution and then 0.2 g of gel formulation per g of hair was uniformly applied on them. The swatches were then left to dry overnight and once dry they were each combed the same total number of times (5 times in total), to release the hair from their fixed state. The anti-frizz performance test was performed at 90% humidity and 22°C for a total duration of 5 h. At the end of the 5 h, the width of each hair swatch was measured in two different areas of the swatch (middle and bottom part), taking care to be consistent on the measurement area on each hair swatch. Additionally, pictures of each hair swatch were obtained, using a camera and a custom-made photo box with controlled light conditions. Table 9. Width of the treated hair swatches after exposure at 90% humidity for 300 min, measured at two different areas (middle and bottom part) of the hair swatch (n=3).

[0162] Mascara formulation

[0163] Procedure

[0164] Heat water to 80°C and disperse the sulfonated co-polyester until a dispersion is formed. Make a slurry of xanthan gum and glycerine and add to phase A until a homogenous gel is formed. Heat phase B until all the waxes are melted. Homogenize phase A with phase B until a homogenous cream is formed. Add the pigment until a homogenous colored paste is formed. Allow to cool down and add the preservative and anti-oxidant when the temperature is below 40°C. Adjust the pH to 6-6.5.

[0165] Table 10. Mascara formulation recipe (pH 6 - 6.5)

[0166] Three-point bending - Film strength / flexibility Procedure

[0167] 2.5 g / 15 cm Caucasian virgin straight hair swatches were washed twice with an SLES 10% solution and they were then left to dry overnight.

[0168] Subsequently, 0.2 g of mascara formulation per g of hair was uniformly applied on them. Three-point bending measurements were performed using the fibra.one equipment (Diastron). The hair swatch is placed horizontally across the two supports of the fixture, ensuring it is centered. The intender is then lowered at a constant rate (50 mm / min) towards the hair swatch and the force (gf) applied by the intender, during its corresponding displacement is recorded. Table 11. Max force (gf) values obtained for the mascara formulations under evaluation using the 3-point bending method (n=5).

Claims

CLAIMSThat which is claimed:1 . A sulfonated co-polyester, comprising the reaction product of:(a) 40 to 100 mole % of an acid component, comprising:(i) a diacid or derivative that is chosen from a (C3-8)cycloalkyl dicarboxylic acid or derivative; a (Ce)aryl dicarboxylic acid or derivative; a (C2-3o)alkyl dicarboxylic acid or derivative, wherein the alkyl is unbranched or branched; a (C2-3o)alkenyl dicarboxylic acid or derivative, wherein the alkenyl is unbranched or branched; or a combination thereof,(ii) a sulfonated dicarboxylic acid or ester of the formula I:I wherein:R is hydrogen or (Ci-4)alkyl;M+is H+, Na+, K+, Li+, or+NH4, and wherein the diacid or derivative is present from 80 to 95 mole %, and the sulfonated dicarboxylic acid or ester is present from 2.5 to 20 mole %, each based on the total moles of the acid component,(b) 88 to 99.6 mole % of a diol component, comprising an unbranched or branched (C2-i2)alkyl diol, a (C3-8)cycloalkyl dimethanol, a (cs- 8)cycloalkyl-diol, which is unsubstituted or substituted by 1 to 4 (Ci- 4)alkyl groups; a compound of formula II: H-(OCH2CH2)n-OH II, wherein n is an integer from 2 to 500; or a combination thereof,(c) 0 to 60 mole % of an ultraviolet light absorbing component, comprising:(i) an ultraviolet light absorbing monocarboxylic acid or ester (“UVMA”) comprising an ultraviolet light absorbing moiety that absorbs light at a wavelength of from 280 to 420 nm, wherein the UVMA is a benzoic acid or ester, a cinnamic acid or ester, a 2-benzoylbenzoic acid or ester, a 3,3-diphenylacrylic acid or ester, or combination thereof, wherein each is unsubstituted or substituted by 1 -4 substituents selected from halo, amino, di(Ci-4)alkylamino, hydroxyl, (Ci- 4)alkoxy, cyano, or (Ci-4)alkyl;(ii) an ultraviolet light absorbing dicarboxylic acid or derivative (“UVDA”) comprising an ultraviolet light absorbing moiety that absorbs light at a wavelength of from 280 to 420 nm, wherein the UVDA is a naphthalene dicarboxylic acid or derivative, a 1 ,1 ’-diphenyl dicarboxylic acid or derivative, a phthalic acid or derivative, a 5-amino-isophthalic acid or ester, a 5-(di(Ci - 4)alkylamino)isophthalic acid or ester, a 4,4'-methylenebis(3- hydroxy-2-naphthoic acid) or ester, 2-benzylmalonic acid or ester, a 5,5'-methylenebis(2-aminobenzoic acid) or ester; or(iii) a combination thereof,(d) 0.4 to 12 mole % of a water dispersing component, comprising a compound of formula III:H-(OCH2CH2)n-O(Ci-4)alkyl,III wherein n is an integer from 2 to 500, wherein the total mole % of all components is 200 mole %, and the total mole % of the acid component, the UVMA, and the UVDA is 100 mole %, and the total mole % of the diol component, and the water dispersing component is 100 mole %, wherein the total mole % of the water dispersing component and the sulfonated dicarboxylic acid or ester derivative of the formula I is at least 8 mole % based on the total moles of all components,wherein the sulfonated co-polyester is dispersible in water at 70°C to form a dispersion having at least 5 wt% of the sulfonated co-polyester based on the total weight of the dispersion, wherein the sulfonated co-polyester has a glass transition temperature (“Tg”) that is in the range of from -60 to 70°C and a melting point (“Tm”) that is in the range of from 45 to 80°C.

2. The sulfonated co-polyester of claim 1 , wherein the sulfonated co- polyester is a random polymer.

3. The sulfonated co-polyester of any one of claims 1 or 2, wherein the inherent viscosity (“IhV”) is in the range of 0.05 to 0.35 dL / g, as determined in a 60 / 40 parts by weight solution of phenol / tetrachlorethane at 25°C and at a concentration of about 0.5 g of sulfonated co-polyester in 100 mL of the solution of phenol / tetrachloroethane.

4. The sulfonated co-polyester of any one of claims 1 -3, wherein the sulfonated co-polyester further comprises a branching component, comprising: (i) a branching polycarboxylic acid; (ii) a branching polyol; (iii) a branching polyfunctional compound; or (iv) a combination thereof.

5. The sulfonated co-polyester of claim 4, wherein the branching component is present at from 0.05 to 4 mole % based on the total moles of all components.

6. The sulfonated co-polyester of any one of claims 1 -5, wherein the branching polyol is 1 ,1 ,1 -trimethylol propane, 1 ,1 ,1 -trimethylolethane, glycerin, pentaerythritol, erythritol, threitol, dipentaerythritol, sorbitol, or combinations thereof; wherein the branching polycarboxylic acid is trimellitic anhydride, pyromellitic dianhydride, or combinations thereof; and wherein the branching polyfunctional compound is dimethylol propionic acid.

7. The sulfonated co-polyester of any one of claims 1 -6, wherein sulfonated co-polyester exhibits at least 10% biodegradability, or at least 15% biodegradability, or at least 20% biodegradability, or at least 30% biodegradability, or at least 40% biodegradability, at least 45% biodegradability, or at least 50% biodegradability, or at least 55% biodegradability, at least 60% biodegradability, or at least 65%biodegradability, or at least 70% biodegradability, or at least 75% biodegradability, or at least 80% biodegradability, or at least 85% biodegradability, at 56 days according to the OECD 301 F test method.

8. The sulfonated co-polyester of any one of claims 1 -7, wherein the compound of formula III is present at from 0.4 to 10 mole% or 0.4 to 8 mole%, or 0.4 to 6 mole%, or 0.4 to 4 mole%, or 0.4 to 2 mole%, or 0.4 to 1 mole%, or 1 to 12 mole%, or 1 to 10 mole%, or 1 to 8 mole%, or 1 to 6 mole%, or 1 to 4 mole%, or 1 to 4 mole%, or 1 to 2 mole%, or 2 to 12 mole%, or 2 to 10 mole%, or 2 to 8 mole%, or 2 to 6 mole%, or 2 to 4 mole%, or 4 to 12 mole%, or 4 to 10 mole%, or 4 to 8 mole%, or 4 to 6 mole%, or 6 to 12 mole%, or 6 to 10 mole%, or 6 to 8 mole%, or 8 to 12 mole%, or 8 to 10 mole%, or 10 to 12 mole%.

9. The sulfonated co-polyester of any one of claims 1 -8, wherein the diol component is an unbranched or branched (C2-i2)alkyl diol or a compound of formula II, wherein n is an integer from 2 to 500; or a combination thereof.

10. The sulfonated co-polyester of claim 9, wherein the diol component comprises an unbranched or branched (C2-i2)alkyl diol.1 1 . The sulfonated co-polyester of claim 9, wherein the diol component comprises or a compound of formula II, wherein n is an integer from 2 to 500.

12. The sulfonated co-polyester of any one of claims 1 -1 1 , wherein the diacid component comprises a diacid or derivative that is a (C2-3o)alkyl dicarboxylic acid or derivative.

13. The sulfonated co-polyester of claim 12, wherein the diacid or derivative is a (C2-e)alkyl dicarboxylic acid or derivative14. The sulfonated co-polyester of claim 13, wherein the diacid or derivative is adipic acid or derivative.

15. A composition comprising any one of the sulfonated co-polyester of any one of claims 1 -14.

16. The compositions of claim 15, wherein the composition is a cosmetic or personal care product.

17. The composition of claim 16, wherein the cosmetic or personal care product is a mascara product, or a hair product.

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