Composition for conditioning fibers; related uses and methods

Abstract

The present patent application discloses novel compositions for conditioning fibers, these being particularly useful for softening, protecting color, improving combability, reducing volume and frizz, reducing wrinkling level, protecting against pilling, reducing permanent deformation, protecting against fraying, reducing fiber breakage caused by brushing, and / or reducing electrostatic charges of the fibers. It further discloses the uses thereof and related methods.

Description

Composition for fiber conditioning; uses and related methods. Technical Field of the Patent Application

[0001] This patent application presents new compositions for fiber conditioning, their uses and related methods. This patent application falls within the technical fields of new fiber treatment compositions and the production of compositions derived from quaternary esters. State of the Art

[0002] Fibers are filamentous structures that can be found in nature or even produced artificially. Examples of natural fibers include silk, cotton fibers, asbestos, and hair. Artificial fibers can be obtained through various processes, aiming at the formation of filaments chemically composed of synthetic polymers, such as nylon and polyester, and semi-synthetic polymers, such as rayon.

[0003] Fibers have diverse applications, with the production of textile fabrics being one of the most significant. A textile fabric is obtained through one or more processes of grouping fibers. One of the most important processes is spinning, which transforms fibers into yarns; these can be used directly in this form or interwoven, forming some types of textile fabrics.

[0004] Unlike the fibers used in the production of textile fabrics, hair fibers can be characterized as cylindrical hair filaments that originate from the scalp and are formed through the keratinization of epithelial cells that are distributed in four main structural units: the cuticle, the cortex, the medulla, and the intercellular cement.

[0005] Hair, in itself, has significant social importance and can have a major impact on personal image and self-confidence. The perception of shiny, healthy, and soft hair depends on environmental exposure, hair treatments, and everyday hair care habits.

[0006] An essential step in hair care is the washing process, where shampoos remove dirt, cosmetic residue, and excess sebum accumulated on the scalp and hair fibers. However, this process can excessively remove lipids and degrade keratin due to the use of anionic surfactants, as well as abrasion, leaving hair dry and rough. Other chemical, mechanical, and thermal treatments, such as straightening, perms, and bleaching, also contribute to this. These factors modify the properties of the hair; associated with UV exposure, there may be removal of the outer lipid layer of 18-methyleicosanoic acid covalently bonded to the hair cuticle, or even oxidation of disulfide bonds to cysteic acid. Such alterations lead to hair with a hydrophilic surface and an accumulation of charges, causing the hair to become dry, frizzy, rough, and difficult to comb.

[0007] The intrinsic properties of fibers can be modified through physical and chemical treatments, commonly called conditioning. Conditioning aims to improve characteristics for a specific application – such as water absorption capacity, elasticity, and strength. These treatments can have varying durability, depending not only on the type of treatment but also on the intended use of the material composed of these fibers. The performance of these conditioners depends on their composition, their ability to deposit on the fibers and surfaces, and their ability to remain bonded to them.

[0008] Specifically regarding hair fibers, conditioning agents prevent or treat unwanted changes. Conditioners contain molecules that accumulate on the scales of the damaged cuticle, filling fractures and fissures. This results in a smooth surface with reduced friction between the fibers, providing softness and shine to the hair, reducing frizz and improving its manageability and ease of combing.

[0009] Most conditioner formulations are based on cationic surfactants known as quaternary ammonium compounds. These compounds have a positively charged hydrophilic group that interacts with hair fibers through electrostatic interactions, and one or more hydrophobic alkyl chains that point toward the outer surface, restoring some of the hydrophobicity lost due to damage. This type of surfactant neutralizes the negative charges of the hair fibers, reducing static electricity. The thin film of conditioner that adsorbs onto the fiber surface flattens the cuticles, making them smooth and improving the softness, manageability, and shine of the hair.

[0010] We can mention behentrimonium chloride (BTAC), dimethylammonium hydrogenated disetaub chloride, and quaternary esters, or "esterquats" (quaternary ammonium compounds containing two long hydrophobic chains with two ester groups) as substances used in fiber conditioning. The first is It is widely used in hair products, and the others are used in fabric softeners.

[0011] An uneven surface is perceived as rougher to the touch – or less smooth – and has a greater capacity to generate friction, which can also lead to an increase in static charge generation. Hair conditioning agents such as BTAC, for example, adhere to hair fibers, replenishing the hydrophobic layers lost due to damage to the hair fiber, providing hydration and giving more uniformity to the surface. Consequently, its use leads to increased combability and reduced volume due to less static charge generation, in addition to providing increased shine and a perception of softness.

[0012] Similarly, dimethylammonium hydrogenated disetabium chloride and esterquats used in fabric softeners adhere to textile fibers, adding a hydrophobic and lubricating layer to them, reducing friction between the fibers. In this way, the generation of static charges is reduced and provides a soft feel to the fabric.

[0013] In the search for the state of the art, the following documents were detected.

[0014] WO9955948A1 describes water-based “anti-wrinkle” compositions comprising a nonionic polyhydric alcohol humectant and an alkali and / or alkaline earth metal salt for spray application to fabrics. Optional surfactants (cationic, nonionic, anionic) may act as wetting agents to facilitate water penetration, including examples of choline esters as preferred cationic wetting agents.

[0015] US6897263B2 discloses betaine esters or betaine ester polymers of formula (I) containing the R groups a R b R c , -CH2- and X attached to the N of betaine and containing at least one carbonyl function, and its homopolymers and copolymers with compounds of general formula (II) and its use in hair conditioning agents.

[0016] However, significant differences are observed between the compositions, formulations, and active substances and the patent application. Furthermore, the degree of green origin of the conditioning agents currently used is low, and they rely on the use of organic solvents or an excessive use of water in their formulations or method of application, as well as raw materials of petrochemical or animal origin for their production.

[0017] Some traditional conditioning agents are reported to cause skin and eye irritation and adverse environmental effects, because They are toxic to aquatic organisms with long-term effects. Because of this, developing highly efficient conditioners from renewable natural resources with low impact on human health and the environment is highly desirable. Summary of the Patent Application

[0018] In this sense, the patent application presents new compositions for fiber conditioning comprising at least one esterquat of General Formula (I): (R f )q-(1,3-DPO)n-RB where: q is an integer between 1 and 10 and n is an integer between 1 and 50; each R f , identical or different, represents a saturated, mono- or polyunsaturated, or hydroxylated C8-C22 acyl radical; (1,3-DPO) represents the repeating unit -O-CH2-CH2-CH2-O-; R B It is a betaine unit linked by an ester and has the general formula -OC(=O)-CH2-N + (CH3)3X“; and X is an acceptable counterion selected from at least one of the following: halides; S-oxyanions; P-oxyanions; C1-C1 carboxylates. 22 ; sulfonates; citrates, tartrates, carbonates / bicarbonate and mixtures thereof.

[0019] This introduces a new class of substances capable of conditioning fibers, which can be produced from renewable raw materials, are solvent-free, and are capable of conditioning fibers and modulating their properties – such as softness, mechanical strength, color protection, and the ability to reduce static charge generation.

[0020] The content presented in this patent application differs, among other reasons, from other existing products also by a new synthesis process, using the principles of green chemistry, allowing the use of raw materials of plant origin and fully biodegradable, and by performance similar to or superior to currently available solutions. Description of the Figures

[0021] Figure 1: Average sound intensity (dB) results calculated for the placebo, active 1, and active 2 groups on 100% cotton fabric.

[0022] Figure 2: Average sound intensity (dB) results calculated for the placebo, active 1, and active 2 groups on 100% polyester fabric.

[0023] Figure 3: Electrostatic Potential Values ​​in (kV) for the placebo, active 1 and active 2 groups in 100% polyester fabric.

[0024] Figure 4: Results of the total color variation - AE*

[0025] Figure 5: Results of the combability assessment of dry hair strands (Average load difference: Before - After treatment) of the groups: Control, BTAC and Active 1.

[0026] Figure 6: Results of the combability assessment of dry hair strands (Average load difference: Before - After treatment) of the groups: Control, Active 3, BTAC and CTAC.

[0027] Figure 7: Results of the frizz assessment of hair strands (difference in the number of pixels: Before - After 24 hours of Treatment) of the groups: Control, Active 3, BTAC and CTAC. * Significant decrease compared to the Control Group (p<0.05).

[0028] Figure 8: Results of the evaluation of hair volume (difference in the total number of pixels: Before - After Treatment) of the groups: Control, Active 3, BTAC and CTAC. * Significant decrease compared to the Control Group (p<0.001). • Significant decrease compared to the BTAC and CTAC Groups (p<0.001). 0 Significant decrease compared to the BTAC Group (p<0.05).

[0029] Figure 9: Evaluation of hair fiber breakage after brushing (Number of fibers after 1000, 2000, 3000, 4000, 5000, 6000, 7000, 8000, 9000 and 10000 cycles) results of the groups: Control, Active 3, BTAC and CTAC. * Significant difference BTAC compared to Control after 1000 cycles (p=0.0022). ** Significant difference BTAC and CTAC compared to Control after 2000 cycles (p=0.0027 and 0.0452, respectively). *** Significant difference Active Test, BTAC and CTAC compared to Control after 3000, 4000, 6000, 7000, 8000, 9000 and 10000 cycles (p=0.0001).

[0030] Figure 10: Sample evaluation scores - Pilling, on red twill fabric.

[0031] Figure 11: Sample evaluation scores - Pilling, on white knit fabric.

[0032] Figure 12: Ratio of Average Permanent Deformation to Average Total Elongation in the length direction, red twill fabric - 97% CO + 3% PUE.

[0033] Figure 13: Ratio of Average Permanent Deformation to Average Total Elongation in the width direction, red twill fabric - 97% CO + 3% PUE.

[0034] Figure 14: Ratio of Average Permanent Deformation to Average Total Elongation in the length direction, white knit fabric - 100%.

[0035] Figure 15: Ratio of Average Permanent Deformation to Average Full stretch widthwise, white knit fabric - 100%. Detailed Description of the Patent Application

[0036] This detailed description of the invention sets forth some, non-limiting definitions of the main terminologies and technical characteristics employed throughout this patent application, as well as providing examples of some embodiments of the present invention so that it may be reproduced by a person skilled in the art.

[0037] In the context of this patent application, esterquats should be understood as quaternary ammonium-derived compounds containing at least one or more fatty acid-derived chains and possessing ester-type linkages in their chemical structure.

[0038] The esterquats described here are divided into two classes, the first class being synthetic products obtained from the reaction of propanediol polyethers, trimethylglycine, and fatty chains from vegetable sources (actives 1 and 2). The second class of esterquats comprises actives without the presence of polyethers (actives 3 and 4).

[0039] In the context of this patent application, "fibers" means natural or artificial filamentous structures, including textile fibers (e.g., 100% cotton and 100% polyester, used in the tests) and hair fibers (human hair), understood as cylindrical hair filaments consisting of a cuticle, cortex and, when present, medulla, with intercellular cement. This definition encompasses isolated fibers, yarns and textile articles obtained by spinning / interlacing, as well as standardized hair strands used in the tests.

[0040] In the context of this patent application, "Fiber Conditioning" means the modification and / or improvement of the physical and / or sensory properties of fibers, verifiable by instrumental and / or sensory methods, including increased softness (reduction of roughness / friction measured by dBxHz sound analysis), reduction of electrostatic charges (measured in kV), color protection (reduced AE*), reduced wrinkling susceptibility (AATCC 128 method), reduced pilling susceptibility (ISO 12945-2), improved elastic properties (reduction of permanent deformation), improved combability (decrease in average combing force), reduced frizz and volume (RUMBA image analysis), and reduced breakage by brushing (fragment count in cycle protocol).

[0041] In the context of this patent application, "Method" or "process of "Fiber conditioning" refers to any effective contact procedure between an aqueous composition containing 0.1-30% (w / w) of the described esterquat(s) and the fibers, sufficient to promote the conditioning effects described above. For example, for textile fibers, the method comprises applying / immersing the fabric in an aqueous softening base containing the active ingredient (e.g., 2.5-4% in the tests), followed by rinsing and drying under usual laundry conditions before instrumental measurements. For hair fibers, the method comprises standardized washing with shampoo, followed by application of a conditioner containing the active ingredient (e.g., 2%), massage along the length, contact time as per protocol (e.g., 30 min in the tests), rinsing and controlled drying, with subsequent evaluation of combability, frizz / volume, and resistance to brushing.

[0042] In one embodiment of the present patent application, “n” is an integer between 1 and 20, optionally between 1 and 10, or optionally between 1 and 5.

[0043] In one embodiment of the present patent application, “q” is an integer between 1 and 5, optionally between 1 and 2.

[0044] In one embodiment of the present patent application, the composition comprises from 0.1% to 30% by mass of one or more esterquats of Formula (I), optionally from 0.5% to 15%, optionally from 1% to 8%, optionally from 2.5% to 5% in a softening or conditioning textile base or a conditioning cosmetic base.

[0045] In one embodiment of the present patent application, the composition comprises water as a vehicle and one or more additional components selected from: cetearyl alcohol, C12-15 alkyl benzoate, ceteareth-20, glycerin, chelating agents, fragrances, preservatives, and colorants.

[0046] In one embodiment of the present patent application, "X" is selected from chloride, lactate, palmitate.

[0047] In an embodiment of the present patent application, each R f It is selected from caprylic (C8), palmitic (C16), ricinoleic (C18:1-OH) or mixtures thereof, preferably of vegetable origin, including castor oil derivatives.

[0048] In one embodiment of the present patent application, the conditioning is intended to soften, protect color, improve combability, reduce volume and frizz, reduce the level of wrinkling, protect against pilling, reduce permanent deformation, protect against fraying, reduce fiber breakage from brushing, and / or reduce electrostatic charges on the fibers.

[0049] In an embodiment of the present patent application, the esterquats of Formula (I) are the product of the reaction between: (a) 1,3-propanediol oligomers, or 1,3-propanediol esters or hydroxyesters; (b) trimethylglycine or its hydrohalic salt, preferably trimethylglycine hydrochloride, or trimethylglycine carboxylates selected from trimethylglycine palmitate and trimethylglycine lactate; (c) one or more C8-C fatty acids 22 .

[0050] In one embodiment of the present patent application, esterquats are obtained by a process comprising: (i) the oligomerization of 1,3-propanediol under acid catalysis, (ii) the formation of the betaine unit by ester by reaction of the oligomer with trimethylglycine or its salt, and (iii) acylation of remaining hydroxyl groups with C8-C22 fatty acid(s) or reactive derivatives.

[0051] In one embodiment of the present patent application, esterquats are obtained by a process comprising: (i) the transesterification of castor oil with 1,3-propanediol under basic catalysis; and; (ii) formation of the betaine unit by ester by reaction of the hydroxyester with trimethylglycine carboxylate(s) under acid catalysis.

[0052] The use of the esterquats described here in a composition for fiber conditioning is also presented.

[0053] In one embodiment of the present patent application, the conditioning use is to soften, protect color, improve combability, reduce volume and frizz, reduce fiber breakage from brushing, and / or reduce electrostatic charges on the fibers.

[0054] A new method for conditioning fibers is also presented, which comprises applying a composition as defined in this patent application to one or more fibers.

[0055] In one embodiment of the present patent application, the conditioning is intended to soften, protect color, improve combability, reduce volume and frizz, reduce fiber breakage from brushing, and / or reduce electrostatic charges on the fibers.

[0056] In the context of this patent application, "textile softening or conditioning base" or "cosmetic conditioning base" designates a dermatologically and / or textile-acceptable carrier formulation matrix suitable for topical application on textile fibrous substrates (e.g. cotton, polyester and blends) and / or human hair fibers. The said base is configured to incorporate, stabilize, carry, promote the deposition and / or ensure the performance of one or more esterquats of Formula (I) on the fibers, and comprises water and, optionally, additional technical components such as: additional cationic, non-ionic, amphoteric and / or zwitterionic surfactants; structuring fatty alcohols; emollients and lipophilic esters; water-soluble solvents and / or hydrophilic-lipophilic co-solvents; viscosity regulators; antifoaming agents; antistatic agents; fragrance agents; colorants; preservatives; chelating agents; film-forming polymers or fiber lubricants; humectants; and emulsifying or self-emulsifying systems.Such bases include, but are not limited to, rinse-off textile softeners, industrial textile finishes, rinse-off and leave-in hair conditioners, treatment masks and styling creams, provided that they are compatible with the incorporation of 0.1% to 30% by mass of the esterquat(s) of Formula (I) and are capable of providing conditioning as defined in this patent application.

[0057] Examples

[0058] Active ingredient 1 (molecule 1)

[0059] Molecule 1 was obtained in 3 synthetic steps through the reaction between 1,3-propanediol, trimethylglycine hydrochloride, and caprylic acid. In the first synthetic step, 1,3-propanediol (6 mol) was converted to its respective polypropanediol under acid catalysis using methanesulfonic acid (2-5%) or sulfuric acid (0.75-1%), nitrogen flow, and a temperature between 120-165°C. In the second step, betaine hydrochloride (1 mol) was added, and the reaction medium was maintained for 6-8 hours at a temperature of 135-150°C under vacuum. In the last synthetic step, caprylic acid (0.8 mol) was added and maintained at a temperature of 110-130°C under vacuum for 2-4 hours, leading to the formation of active ingredient 1 with an 85% yield. Molecule 1

[0060] Active ingredient 2 (molecule 2)

[0061] Active ingredient 2 was obtained in 3 synthetic steps through the reaction between 1,3-propanediol, trimethylglycine hydrochloride, and ricinoleic acid. In the first synthetic step, 1,3-propanediol (10 moles) was converted into its respective polypropanediol (1,3- PDO) under acid catalysis using methanesulfonic acid (2-5%) or sulfuric acid (0.75-1%), nitrogen flow, and a temperature between 120-165°C. In the second step, trimethylglycine hydrochloride (1 mol) was added, and the reaction medium was maintained for 6-8 hours at a temperature of 135-150°C under vacuum. In the final synthetic step, ricinoleic acid (0.8 mol) was added and maintained at a temperature of 130-150°C under vacuum for 4-6 hours, leading to the formation of active ingredient 2 with a yield of 77%. Molecule 2

[0062] Active ingredient 3 (molecules 3, 4 and 5)

[0063] Active ingredient 3 was obtained through the reaction between castor oil (ricinoleic acid), 1,3-propanediol, trimethylglycine, and palmitic acid in two distinct steps. The first synthetic step comprises a transesterification reaction between castor oil (1 mol) and 1,3-propanediol (3 mols) under basic KOH catalysis in 1,3-propanediol, previously prepared at a concentration of (2%), at a temperature between 65-75°C, followed by neutralization, washing, and drying (Scheme 3). In the next step, the hydroxyester obtained in step 1 is esterified with trimethylglycine palmitate using heterogeneous acid catalysis, at a temperature between 130-150°C and vacuum. The reaction system was maintained for 5 to 8 hours, leading to the formation of molecule 3 in greater proportion and molecules 4 and 5 in smaller proportions. Yield of 72-78%. Molecule 4

[0064] Active ingredient 4 (molecules 6, 7 and 8)

[0065] Active ingredient 4 was obtained through the reaction between castor oil (ricinoleic acid), 1,3-propanediol, trimethylglycine, and lactic acid, in two distinct steps. The first synthetic step comprises a transesterification reaction between castor oil (1 mol) and 1,3-propanediol (3 mols) under basic catalysis (KOH) in previously prepared 1,3-propanediol at a concentration of (2%), temperature between 65-75°C, followed by neutralization, washing, and drying (Scheme 5). In the next step, the hydroxyester obtained in step 1 is esterified with trimethylglycine lactate, methanesulfonic acid as catalyst (2%), temperature between 140-160°C and vacuum. The reaction system was maintained for 6 to 10 hours, leading to the formation of molecule 6 in greater proportion and molecules 7 and 8 in smaller proportions. Yield 81-84%. Molecule 7

[0066] Softness tests on textile fibers

[0067] Description of the group test:

[0068] Group 1 - Standard fabric softener containing 4% hydrogenated dimethyl ammonium chloride in water.

[0069] Group 2 - Fabric softener containing 4% of active ingredient 1 and 96% water.

[0070] Group 3 - Fabric softener containing 4% of active ingredient 2 and 96% water.

[0071] Fabrics evaluated:

[0072] 100% Cotton

[0073] 100% Polyester

[0074] The condition of a surface being smoother or rougher is readily identified by the consumer in order to assign a feeling of comfort to the touch.

[0075] The reduction of friction is directly linked, microscopically, to the increase in the smoothness of a product's surface, which includes a decrease in the roughness of this evaluated surface. Macroscopically, it is also necessary that there be a lower degree of aggregation and interaction between non-woven and / or polymeric fibers, depending on the product used.

[0076] All these characteristics can be associated with the softness of the material being evaluated; the less friction during use, the greater the feeling of softness.

[0077] Softness can be assessed using electronic sensors capable of measuring the roughness of textile and / or polymer fibers by collecting the sound generated by the friction of this material on the sensor. These musical files were then converted into Frequency (Hz) and Intensity (dB) data, where a more regular and less rough surface presents attenuated sound, indicating greater conditioning and softness of the textile fiber.

[0078] Evaluation of Friction in Textile Fibers

[0079] Measurement and data collection procedures:

[0080] Equipment with electronic sensors (WIDI 4.50 Pro software) was used to translate the roughness of textile fibers into a melody, based on the friction of these fibers on the sensor. The analyses were performed in triplicate for each sample.

[0081] The file obtained in .htaccess format was converted into a text file using Audacity software. This allowed us to obtain Intensity (dB) data as a function of Frequency (Hz).

[0082] Based on the intensity data, the average intensity was calculated for each treatment. A positive dB value indicates a ratio greater than one (gain). A negative value indicates a ratio less than one (attenuation), and a value of zero indicates that there are no changes in the signal.

[0083] Lower Intensity values ​​indicate that each fabric exhibited a lower coefficient of friction, which implies greater efficiency of the treatment in reducing the friction of the fibers on the sensor, i.e., greater softness.

[0084] Methodology adopted in sound tests

[0085] The sample was kept for 24 hours in a controlled environment (22±2°C and 55±5%) before analysis.

[0086] Statistical test used in the evaluation of softness.

[0087] GraphPad™ Prism® Software 8.4.3.

[0088] 1) Comparison with the Control group: one-way analysis of variance method with Dunnett's post-hoc test, considering a 95% confidence interval.

[0089] 2) Comparison between treatments: bimodal, unpaired Student's t-test, considering a 95% confidence interval.

[0090] Results

[0091] According to the results, it was observed that the groups containing active ingredients 1 and 2 presented significantly lower sound intensity values ​​compared to the benchmark group in polyester (p< 0.0399) and cotton (p< 0.0382) fabrics, figures 1 and 2. Thus, it can be inferred that the fabrics after treatment with active ingredients 1 and 2 showed a significant reduction in friction values ​​compared to the placebo group (Standard Softener), indicating greater softness of the textile fiber.

[0092] Electrostatic Charge Test

[0093] When the surfaces of two different materials are rubbed together and then separated, electrical charges are generated; this phenomenon is called the Triboelectric Effect. Microscopically, during friction, there is a transfer of Electrons move from one surface to another, and when the surfaces are separated, one body ends up with an excess of electrons and a negative charge; the other ends up with a lack of electrons and a positive charge. The net charge of the bodies remains constant, that is, the charge is conserved, giving rise to the physical phenomenon known as static electricity. The value of the electrostatic charge can be calculated using Coulomb's equation Q = CV.

[0094] The electrostatic charge value in fabrics is important because the higher the electrostatic charge value, the greater the propensity for particle accumulation, in addition to providing stiffness to the fibers, making them less soft.

[0095] To obtain the static potential (kV) measurements, an Electrostatic Fieldmeter was used.

[0096] Initially, electrostatic charge values ​​are measured, and subsequently the fabric is subjected to friction cycles with a glass plate, after which the electrostatic charge values ​​are measured again.

[0097] From the static potential (kV) measurements, the percentage reduction in static charge formation, RC in (%), is calculated according to Equation 2: %RC=(PBasal-PFinal) / (PBasal), where P is the static potential in (kV).

[0098] Statistical test used in the evaluation of electrostatic charge.

[0099] Method: Paired, bimodal Student's t-test. Confidence interval: 95%.

[0100] Software: GraphPad™ Prism® 8.4.3.

[0101] According to the results obtained in the electrostatic charge reduction tests on polyester fabric, it was observed that the placebo group did not show a significant reduction in electrostatic potential when compared to the initial state. On the other hand, the groups treated with active ingredients 1 and 2 showed significant values ​​(p<0.0001) in the reduction of electrostatic charge, leading to a charge reduction of 77% and 66% for active ingredients 1 and 2 respectively (Figure 3). Based on the results obtained, active ingredients 1 and 2 confer antistatic properties and greater softness to the fabric, corroborating the results obtained in the sound effect tests.

[0102] Color protection test on textile fabric

[0103] Equipment for color measurement: Delta Color Spectrophotometer - Model: Delta Vista 450G.

[0104] Color space used for color measurement: CIELAB (CIE Illuminant Des / Observer 10°).

[0105] Number of samples: 5.

[0106] Sample dimensions (cm): 10 x 10.

[0107] Number of measurements: 5 distinct points in each sample.

[0108] Benchmark: Dialkyl Ammonium Methosulfate. Result 1 (group to be evaluated) Percentage change (%) = - - — - - - - — — 1 * 100 Result 2 (group to be compared)

[0109] The CIELAB coordinates (L* a* b* and AE*) of the fabrics will be determined from the parameters L* a* b* (CIELAB system), which will be measured before and after washing and drying, and the color changes of the fabrics will be evaluated through calculations of the delta E* parameter (AE*).

[0110] The color tolerance between two stimuli (standard and sample, for example) and the acceptance criteria are defined primarily based on the AE parameter, which aims to quantify the total color variation, being the square root of the sum of the squared differences of all coordinates L* a* b*. Furthermore, it is important to mention that the color difference can be considered perceptible or insignificant within a color space, or relevant or significant within another context.

[0111] The C / EL*a*b* system was created based on the theory of opposite colors, where two colors cannot be green and red at the same time, or yellow and blue at the same time, since colors are formed by mixing primary colors and all others are combinations of these. Other evaluations regarding brightness, hue, and saturation (L*, a*, b*) may also be scored, always taking into account the items and / or attributes that one wishes to categorize.

[0112] The pre-established parameters can be described as:

[0113] AE*: Indicates the total color variation. The closer to 0, the smaller the color variation of the fabrics.

[0114] According to the results obtained in the total color variation test (AE*), it was observed that the red twill fabric treated with the Benchmark and Active Ingredient 4 groups showed color protection when compared to the placebo group. The softener base, containing 2.5% of Active Ingredient 4, showed superior color protection of 84.2% when compared to the placebo group. On the other hand, the benchmark group, containing 5% of the active ingredient, showed 79.4% protection compared to the placebo. Based on the results obtained, it was observed that Active Ingredient 4 provided better color protection for the fabric. half the concentration of active ingredient compared to the benchmark group, on a softening basis (Figure 4).

[0115] Recovery from wrinkling Method: AATCC 128 Equipment: Wrinkle Tester Applied mass (kg): 3.5 Benchmark: Dialkyl Ammonium Methosulfate Number of samples: 3 Number of observers: 3 Sample dimensions (cm): 15 x 28 Notes on visual classification: AATCC - WR (grade 5 to 1) Test location: Metrology Laboratory - SENAI CETIQT

[0116] Fabric wrinkling occurs when its threads and fibers are folded in such a way that some parts are under compression and others under tension. The propensity for wrinkling varies according to the type of fabric. Some materials, such as cotton, tend to wrinkle more easily than others, such as polyester or silk. The use of fabric softeners reduces stiffness and friction between the fibers, thus increasing their mobility and potentially improving the wrinkling resistance of fabrics.

[0117] In the wrinkle susceptibility test, the objective is to evaluate the ability of the fabric or article to recover from creases formed after induced crushing. The evaluation is performed qualitatively, after comparison with a three-dimensional standard.

[0118] The specimens are analyzed in triplicate by 3 evaluators simultaneously, with individualized scores, which may be intermediate (1-2 for example), and the averages of the assigned scores are subsequently reported.

[0119] Wrinkling is one of the major challenges in the laundry industry, as people have less and less time available each day to perform household chores, including ironing. Therefore, products that reduce wrinkling result in less wrinkled fabrics, making ironing easier and potentially eliminating the need for ironing altogether. Thus, we evaluated the anti-wrinkle potential of active ingredient 4 compared to a placebo group and a benchmark group.

[0120] In evaluating the results, it was observed that for the white knit fabric, which is more prone to wrinkling, the group treated with active ingredient 4 showed a higher value compared to the average of the evaluations, reaching a score of 4, against a score of 2 for the placebo and benchmark groups. A score of 5 represents fabric without wrinkling and 1 represents very wrinkled fabric, indicating 100% protection against wrinkling compared to the other groups. Furthermore, these values ​​indicate that active ingredient 4 has a 66.6% greater wrinkle recovery capacity compared to the placebo and benchmark groups. On the other hand, the benchmark group did not show wrinkle recovery capacity compared to the placebo group.

[0121] Tendency to form pilling Method: ISO 12945-2:2020 Equipment: Martindale Number of samples: 3 Number of observers: 2 Number of cycles: 125, 500, 1000, 2000, 5000 and 7000 Evaluation method: Notes on visual classification (5 - no pilling formation to 1 - extremely severe pilling formation) Test location: Metrology Laboratory - SENAI CETIQT

[0122] It was observed that the red twill sample treated with active ingredient 4 obtained the maximum score in the pilling propensity study, reaching a value of 5 after 7000 cycles, showing that the fabric did not form pilling "balls," as shown in Figure 10. On the other hand, in 125 cycles, all groups that were not treated with esterquat presented a score of 4, indicating premature fabric wear.

[0123] With these results, it was observed that the group containing active ingredient 4 showed 100% protection against pilling formation, indicating little or no alteration on the sample surface, compared to 50% protection in group G2 compared to the placebo group. Therefore, we infer that active ingredient 4, at a concentration of 2.5%, is effective in protecting the fabric against pilling formation. Active ingredient 4 was also evaluated on white knit fabric, which proved superior in protection against pilling formation compared to the placebo and benchmark groups, showing 50% more protection compared to groups G1 and G2 (Figure 11).

[0124] Determination of elasticity properties Method: ISO 20932-1 - Method A Equipment: Dynamometer Conditioning: 20 ± 2 °C and 65 ± 4% RH for 24 hours. Pre-tension (cN / cm) = 1 Distance between the claws (mm): 200 Separation speed of the moving gripper (mm / min): 100 Applied load (kg): 2.0 Number of samples: 5 lengthwise and 5 widthwise, in each condition. Sample dimensions (mm): Approx. 60 x 300 Test location: Chemistry and Manufactured Products Laboratory - LQM / IPT

[0125] The ability of a material to deform under the application of a specific load and then recover its original shape after the removal of that load is one of the most important properties attributed to textile materials (ADANUR, 1995). This ability translates into various capabilities that affect the performance of fabrics, depending on their constructive and structural characteristics. In the test for determining elasticity properties, the percentage of total elongation is evaluated to assess the permanent deformation generated in the process. Excessive elongation of textile articles can cause undesirable effects such as fraying or deformation, potentially leading to a shorter lifespan of the garments; therefore, it is important to verify the resistance and elasticity of the materials. Deformation is the alteration of the shape undergone by a body subjected to an external force.Despite the body's tendency to return to its original shape, when the limit of proportionality between load and deformation is broken, what remains are called permanent deformations.

[0126] During testing, both fabrics treated with different formulations were tested in both the lengthwise (longitudinal) and widthwise (transverse) directions of the garment.

[0127] Results

[0128] Permanent deformation

[0129] Regarding permanent deformation, which corresponds to the residual portion of the total elongation that was not recovered by the material after its extension (Technical Report 171 948-205 - IPT, 2024).

[0130] For the red twill fabric, it was noted that, in the lengthwise direction, group G3 (containing active ingredient 4 at 2.5%) obtained the least permanent deformation. Comparing group G1 (placebo) and G2 (benchmark), group G3 showed 19.77% less deformation compared to the placebo group and 34.47% compared to the benchmark group, Figure 12. Regarding the widthwise direction, the group treated with active ingredient 4 had high recovery from deformation, showing 88.18% less deformation compared to the placebo group and 88.64% compared to the benchmark group, demonstrating that the active ingredient provides high protection against fabric fraying, Figure 13.

[0131] For the white knit fabric, the group treated with active ingredient 4 also showed protection against fraying, presenting protection values ​​of 20.51% compared to the placebo group and 11.42% compared to the benchmark group, in the length direction, Figure 14. Regarding the width direction, group G3 presented values ​​of 32.60% compared to the placebo group and 29.54% compared to the benchmark group, indicating that the active ingredient is capable of protecting both flat and non-flat fabrics against fraying, Figure 15.

[0132] Performance tests on hair fibers

[0133] The tests were performed using standardized Caucasian hair strands (25 cm, 2 g each), dark brown in color, supplied by International Hair Importers - USA.

[0134] Before testing, all hair strands were washed with an SLES solution (8.1% active ingredient) and air-dried (24h) at 22±2°C (71.6°F) and 50±5% RH. Tests were conducted under the same environmental conditions.

[0135] For subsequent testing, the hair strands were subjected to standardized washing and drying procedures, followed by a chemical bleaching process.

[0136] Procedure for applying the formulations to hair strands.

[0137] Bleached hair strands treated with shampoo, with or without (control group) conditioning formulations (Water, Cetearyl Alcohol, C12-15 Alkyl Benzoate, Ceteareth-20, Glycerin, Xylitol Sesquicaprylate, Disodium EDTA) containing 2.0% alkyl amino diester, or 2.0% cetyl trimethyl ammonium chloride (CTAC), or 2.0% behenyl trimethyl ammonium chloride (BTAC), or the test active ingredient, were compared to evaluate the conditioning efficacy of the formulations. The formulations were applied according to the protocol described below:

[0138] Shampoo: A standardized amount of shampoo was applied to the hair. Wet and gently massaged for 2 minutes. Then rinsed for 1 minute and thoroughly dried with a towel.

[0139] Conditioner: A standardized amount of conditioner (50% of the hair strand weight) was applied to damp hair and gently massaged along the entire length. It was then left on for 30 minutes, rinsed for 1 minute, and dried with a hairdryer (medium temperature). This process was repeated twice. The final treatment, after applying the formulation, was left on overnight.

[0140] Description of the group test

[0141] Control - bleached hair strands treated with a shampoo formulation.

[0142] Active ingredient 1 or 3 - bleached hair strands treated with a control shampoo and conditioner (2% test active ingredient).

[0143] BTAC - bleached hair strands treated with a control shampoo and conditioner (2% BTAC).

[0144] CTAC - bleached hair strands treated with a control shampoo and conditioner (2% CTAC).

[0145] Evaluation of dry hair combability

[0146] The combability of four hair strands per group was measured before and after treatment using the Hair Combing Rig as a texture analyzer TA. XT Plus (Stable Micro Systems, UK).

[0147] The Hair Combing Rig is positioned on the texture analyzer, and the length of the hair strands is held vertically. This allows the combing tool to pass through the hair and record the force required to comb / detangle along its length. For the test, two cycles (10 readings per cycle) were performed on each strand, one on each side.

[0148] The results consist of an evaluation of the difference in the average combability force parameter before and after treatment. A decrease / reduction in the average combability force values ​​indicates an improvement in hair combability.

[0149] Statistical test for combability study

[0150] Method: Kruskal-Wallis and Dunn's non-parameterized.

[0151] Confidence interval: 95%.

[0152] GraphPad™ Prism® 10.1.2.

[0153] According to Figure 6, it is possible to observe that the strands from the Active 3, BTAC, and CTAC groups, after the treatments, showed a significant decrease (p<0.001) in Average Load values ​​compared to the strands from the Control group, indicating that the new conditioning active ingredient presented similar performance results to the BTAC and CTAC groups in reducing average strength values, providing improved hair combability.

[0154] Hair volume assessment and frizz reduction

[0155] Hair volume and frizz were measured using the RUMBA device (Bossa Nova Technologies, USA) on four bleached hair strands per group and eight images with different angles per hair strand.

[0156] The equipment is dedicated to measuring the orientation and volume of hair fibers. After processing the hair image, the software allows the user to obtain a complete analysis of hair volume and frizz by calculating the total number of pixels (Integral) corresponding to the total hair volume or images of the frizz fiber.

[0157] Hair strands were evaluated before and after treatments. After treatments, they were equilibrated within a xenon flatbed instrument (Suntest XXL+FD) for 24 hours under controlled humidity (70 ± 5%) and temperature (25 ± 2°C). New measurements were taken after 6 and 24 hours of humidity exposure.

[0158] Statistical test used in the evaluation of Frizz

[0159] Method: Unpaired Student's t-test.

[0160] Confidence interval: 95%.

[0161] GraphPad™ Prism® 10.1.2.

[0162] Statistical test used in volume assessment.

[0163] Method: ANOVA and Tukey.

[0164] Confidence interval: 95%.

[0165] GraphPad™ Prism® 10.1.2.

[0166] After 24 hours of treatment, it was observed that the hair strands treated with the conditioner formulations containing Active Ingredient 3 and BTAC maintained a significant reduction in frizz compared to the control group. The strands treated with Active Ingredient 3 and BTAC showed a longer-lasting effect in reducing frizz, indicating that the use of Active Ingredient 3 provides similar efficacy to BTAC, proving to be a strong candidate to replace BTAC in these applications (Figure 7).

[0167] According to the results presented in Figure 8, it was observed that the hair strands treated with the conditioner formulations containing Active Ingredient 3, BTAC, or CTAC showed a significant reduction in hair volume compared to the control group after treatment. On the other hand, the hair strands treated with Active Ingredient 3 showed a significant reduction in hair volume compared to the groups treated with BTAC and CTAC.

[0168] Assessment of hair fiber breakage after brushing.

[0169] To assess hair fiber breakage after brushing, a BPLA 300 automatic brushing device (Bioluz - BR) was used. This device is a rotary equipment with 4 brushes for each strand evaluated, simulating a standardized brushing process. At the end of each brushing cycle, the hair fiber fragments deposited in a tray located below the hair fiber samples are counted. The test was performed using four hair strands per group, which were brushed at a speed of 11 (~142 rpm) in 1000 cycles until reaching 10000 cycles. The hair fiber fragments were quantified every 1000 cycles.

[0170] Statistical analysis: Statistical test used in the evaluation of frizz.

[0171] Method: Unpaired Student's t-test.

[0172] Confidence interval: 95%.

[0173] GraphPad™ Prism® 10.1.2.

[0174] The differences were considered statistically significant at p<0.05.

[0175] According to Figure 9, we observed that the strands treated with conditioner containing Active 3, BTAC, and CTAC groups showed a significant decrease in the number of broken hair fiber fragments compared to the Control group after 1000 to 10000 brushing cycles, indicating that these products protect the hair from breakage during brushing processes.

[0176] The results obtained in this study reinforce the already established effectiveness of conditioner / softener formulations based on BTAC, CTAC, and other esterquats. The tested formulations based on BTAC and CTAC provided a significant improvement (p<0.001) in hair combability (average reduction in weight) and a significant decrease (p<0.001) in the number of broken fragments of hair fibers after 10,000 brushing cycles, compared to the values ​​of hair treated only with shampoo (control group). The conditioner formulations also showed immediate and lasting effectiveness in reducing frizz and volume. hair.

[0177] Active ingredients 1 and 3, tested in this study as novel hair conditioning agents derived from renewable natural resources and obtained using green chemistry concepts, provided good sensory properties and similar efficacy (no statistical difference) in combability assessments (average load reduction), brushing resistance (6000 to 10000 cycles), and frizz reduction (immediate and lasting efficacy), compared to BTAC and CTAC. The conditioner formulation with Active ingredient 3 showed the best immediate and lasting efficacy in reducing hair volume, with a significant difference (p<0.01) compared to the conditioner formulations containing BTAC and CTAC.

[0178] The test results show the potential of Assets 1, 2, 3, and 4 as green alternatives to traditional petrochemical-derived quaternary compounds, acting as novel fiber conditioning / softening agents.

[0179] In summary, this document describes new fiber conditioning / softening agents obtained through a sustainable chemical synthesis process, using green chemistry concepts, from vegetable oil or fatty acids, 1,3-propanediol, trimethylglycine, and palmitic acid or lactic acid.

[0180] Based on the content disclosed in this patent application, it is possible to formulate conditioning products for fibers and surfaces, aiming to increase softness, improve combability, reduce frizz, reduce hair fiber breakage, and reduce electrostatic charges, among other physical properties.

[0181] The examples disclosed herein demonstrate only some of the ways in which the present invention can be carried out and used. Alternative forms and variations of the invention may be devised by a person skilled in the art based on the technical knowledge described in this patent application and are defined in their entirety by the claims set forth herein.

Claims

Claims 1. Composition for conditioning fibers characterized by comprising at least one esterquat of General Formula (I): (R f )q-(1,3-DPO)nR B where: q is an integer between 1 and 10, and n is an integer between 1 and 50; each R f , identical or different, represents a saturated, mono- or polyunsaturated, or hydroxylated C8-C22 acyl radical; (1,3-DPO) represents the repeating unit -O-CH2-CH2-CH2-O-; R B It is a betaine unit linked by an ester and has the general formula -OC(=O)-CH2-N + (CH3)3X“; and X is an acceptable counterion selected from at least one of the following: halides; S-oxyanions; P-oxyanions; C1-C1 carboxylates. 22 ; sulfonates; citrates, tartrates, carbonates / bicarbonate and mixtures thereof.

2. Composition according to claim 1, characterized in that n is an integer between 1 and 20.

3. Composition according to claim 1, characterized in that q is an integer between 1 and 5.

4. Composition according to claim 1, characterized by comprising from 0.1% to 30% by mass of one or more esterquats of Formula (I) in a textile softening or conditioning base, or in a cosmetic conditioning base.

5. Composition according to claim 1, characterized by comprising water as a vehicle and one or more additional components selected from: cetearyl alcohol, C12-15 alkyl benzoate, ceteareth-20, glycerin, chelating agents, fragrances, preservatives and colorants.

6. Composition according to claim 1, characterized in that X” is selected from chloride, lactate, palmitate.

7. Composition according to claim 1, characterized by each R fto be selected from caprylic (C8), palmitic (C16), ricinoleic (C18:1 -OH) or mixtures thereof, preferably of vegetable origin, including castor oil derivatives.

8. Composition, according to claim 1, characterized by conditioning, softening, protecting color, improving combability, reducing volume and frizz, reducing the level of wrinkling, protecting against pilling, reducing permanent deformation, protecting against fraying, reducing fiber breakage by brushing and / or reducing electrostatic charges on the fibers.

9. Composition according to claim 1, characterized in that the esterquats of Formula (I) are the product of the reaction between: (a) 1,3-propanediol oligomers, or 1,3-propanediol esters or hydroxyesters; (b) trimethylglycine or its hydrohalic salt, preferably trimethylglycine hydrochloride, or trimethylglycine carboxylates selected from trimethylglycine palmitate and trimethylglycine lactate; (c) one or more C8-C fatty acids 22 .

10. Composition according to claim 9, characterized in that the esterquats are obtained by a process comprising: (i) the oligomerization of 1,3-propanediol under acid catalysis, (ii) the formation of the betaine unit by ester by reaction of the oligomer with trimethylglycine or its salt, and (iii) acylation of remaining hydroxyl groups with C8-C22 fatty acid(s) or reactive derivatives.

11. Composition according to claim 9, characterized in that the esterquats are obtained by a process comprising: (i) the transesterification of castor oil with 1,3-propanediol under basic catalysis; and; (ii) formation of the betaine unit by ester by reaction of the hydroxyester with trimethylglycine carboxylate(s) under acid catalysis.

12. Use of a composition, as defined in any one of claims 1 to 11, characterized in that it is for conditioning the fibers.

13. Use, according to claim 12, characterized by conditioning, softening, protecting color, improving combability, reducing volume and frizz, reducing fiber breakage from brushing and / or reducing electrostatic charges on the fibers.

14. Fiber conditioning method, characterized by comprising the application of a composition as defined in any one of claims 1 to 11 onto one or more fibers.

15. Method, according to claim 14, characterized by conditioning, softening, protecting color, improving combability, reducing volume and frizz, reducing fiber breakage from brushing and / or reducing electrostatic charges on the fibers.

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