CN115418853B - Hydrolysis inhibitor containing ester group quaternary ammonium salt and fabric softening composition - Google Patents

Hydrolysis inhibitor containing ester group quaternary ammonium salt and fabric softening composition Download PDF

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CN115418853B
CN115418853B CN202211037676.9A CN202211037676A CN115418853B CN 115418853 B CN115418853 B CN 115418853B CN 202211037676 A CN202211037676 A CN 202211037676A CN 115418853 B CN115418853 B CN 115418853B
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fabric softening
softening composition
alcohol
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quaternary ammonium
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CN115418853A (en
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龙海华
郑翔龙
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Guangzhou Blue Moon Industrial Co ltd
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Guangzhou Blue Moon Industrial Co ltd
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/144—Alcohols; Metal alcoholates
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/144—Alcohols; Metal alcoholates
    • D06M13/148—Polyalcohols, e.g. glycerol or glucose
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/152—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen having a hydroxy group bound to a carbon atom of a six-membered aromatic ring
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/02—Natural fibres, other than mineral fibres
    • D06M2101/04—Vegetal fibres
    • D06M2101/06—Vegetal fibres cellulosic
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/50—Modified hand or grip properties; Softening compositions

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  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Biochemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

Hydrolysis inhibitors of quaternary ammonium salts containing ester groups and fabric softening compositions are disclosed. This hydrolysis inhibitor is an organic compound having a ClogP in the range of-1.37 < ClogP < 15 and containing functional groups capable of forming hydrogen bonds. The invention also provides a fabric softening composition comprising the hydrolysis inhibitor and an ester group-containing quaternary ammonium salt. The hydrolysis inhibitor provided by the invention can effectively inhibit the hydrolysis of the ester quaternary ammonium salt, so that the long-term storage stability of the fabric softening composition comprising the ester quaternary ammonium salt can be improved, and meanwhile, the compatibility of the formula is good. The fabric softening composition is applied to fabric softening treatment, has good softening, antistatic and sterilizing effects, and is quite wide in application earlier stage.

Description

Hydrolysis inhibitor containing ester group quaternary ammonium salt and fabric softening composition
Technical Field
The invention relates to the technical field of daily chemistry, in particular to a hydrolysis inhibitor of quaternary ammonium salt containing ester groups and a fabric softening composition.
Background
Quaternary ammonium salts containing ester groups are widely used for the preparation of fabric softeners because of their ease of biodegradation. However, the quaternary ammonium salt containing the ester group has natural defects that the ester group is easy to hydrolyze, obvious fine particles are separated out from the product in long-term storage, obvious thickening phenomenon occurs, and even the product cannot be used continuously. The problem of hydrolysis is particularly pronounced when stored at different temperatures, especially under high temperature conditions such as 40-90 ℃.
The prior art discloses fabric treatment compositions containing periodate salts. Periodate can inhibit hydrolysis of quaternary ammonium salts containing ester groups. However, periodate also has significant drawbacks, in that it is too oxidizing and can negatively affect other components of the composition, such as color fading, flavor discoloration, off-flavor, etc.
Therefore, how to inhibit the hydrolysis of quaternary ammonium salt containing ester group and improve the long-term storage stability of the product is still a technical problem to be solved.
Disclosure of Invention
The present invention aims to solve at least one of the above technical problems in the prior art. It is therefore an object of the present invention to provide a hydrolysis inhibitor for quaternary ammonium salts containing ester groups, a second object of the present invention to provide a fabric softening composition, a third object of the present invention to provide a process for the preparation of such a fabric softening composition, and a fourth object of the present invention to provide the use of such a fabric softening composition in fabric softening treatment.
In order to achieve the above purpose, the technical scheme adopted by the invention is as follows:
in a first aspect the present invention provides a hydrolysis inhibitor for quaternary ammonium salts containing ester groups, the hydrolysis inhibitor being an organic compound having a ClogP in the range-1.37 < ClogP < 15 and containing functional groups capable of forming hydrogen bonds.
The present inventors have found that when-1.37 < ClogP < 15 and a compound containing a functional group capable of forming a hydrogen bond is used as a hydrolysis inhibitor, hydrolysis of the ester group-containing quaternary ammonium salt can be effectively inhibited and long-term storage stability of a composition comprising the ester group-containing quaternary ammonium salt can be improved, and the composition is safer for other components of the composition and has better compatibility.
According to some embodiments of the hydrolysis inhibitor of the invention, the hydrolysis inhibitor has a ClogP in the range of: -ClogP not less than 0.05 and not more than 12.
According to some embodiments of the hydrolysis inhibitor of the present invention, the functional group capable of forming hydrogen bonds comprises at least one of a hydroxyl group, a carboxyl group, an aldehyde group, an amino group, an ether bond.
According to some embodiments of the hydrolysis inhibitor of the present invention, the hydrolysis inhibitor comprises at least one of an alcohol compound, a phenolic compound.
According to some embodiments of the hydrolysis inhibitor of the present invention, the hydrolysis inhibitor comprises at least one of 2-methyl-2, 4-pentanediol, anisyl alcohol, benzyl alcohol, phenethyl alcohol, phyllyl alcohol, 2-hexenyl alcohol, cinnamyl alcohol, 3-phenylpropanol, dimethylbenzyl methanol, myrcenyl alcohol, terpineol, linalool, geraniol, menthol, citronellol, tetrahydrolinalool, alpha-amyl cinnamyl alcohol, C12-C24 alcohol, dimethyl hydroquinone, eugenol, isoeugenol, thymol or an isomer thereof (such as 3-methyl-4-isopropylphenol), carvacrol.
In a second aspect the present invention provides a fabric softening composition comprising the following components:
component A: quaternary ammonium salt containing ester group;
component B: a hydrolysis inhibitor according to the first aspect of the present invention;
water;
wherein the mass percentage of the component A in the fabric softening composition is 0.5-25%; the mass percentage of the component B in the fabric softening composition is 0.05-10%.
According to some embodiments of the fabric softening compositions of the present invention, the quaternary ammonium salt containing ester groups has a structural formula as shown in formula (1):
in the formula (1), R 1 Selected from C11-C23 substituted or unsubstituted aliphatic hydrocarbon groups, said substituted groups being selected from-OH, phenyl or- (CH) 2 CH 2 O) m ；m＝1～10；
R 2 、R 3 May be the same OR different and are each independently selected from the group consisting of-C (O) OR, -OC (O) R, -C (O) O (CH) 2 CH 2 O) n R, benzyl, phenyl, -OH or H, wherein R is selected from C10-C22 branched or straight chain alkyl; n=1 to 10;
R 4 selected from-OH or H;
b is selected from integers from 1 to 5;
when R is 2 、R 3 、R 4 When H, c, d and e can be the same or different and are respectively and independently selected from integers of 0-3;
when R is 2 、R 3 、R 4 When the three groups are not H, c, d and e can be the same or different and are respectively and independently selected from integers of 1-3;
x is an anion of valence a, X -a Selected from Br - 、Cl-、CH 3 SO 4 - Or CH 3 CH 2 SO 4 - 。
According to some embodiments of the fabric softening compositions of the present invention, the ester group containing quaternary ammonium salt comprises the reaction product of a fatty amine, a fatty acid/grease, and an alkylating agent. In some embodiments, the fatty amine comprises at least one of methyldiethanolamine, dimethylethanolamine, triethanolamine; the fatty acid comprises saturated or unsaturated fatty acid, fatty acid with or without hydroxyl; the alkylating agent comprises at least one of dimethyl sulfate, diethyl sulfate, chloromethane and bromomethane. Wherein the carbon chain length of the fatty acid may be selected from the group consisting of C12 to C22.
According to some embodiments of the fabric softening composition of the present invention, the mass percentage of component a in the fabric softening composition is from 0.1% to 20%.
According to some embodiments of the fabric softening composition of the present invention, the mass percentage of component a in the fabric softening composition is 1% to 15%.
According to further embodiments of the fabric softening composition according to the present invention, the component a is present in the fabric softening composition in an amount of 1% to 10% by mass.
According to some embodiments of the fabric softening composition of the present invention, the mass percentage of component B in the fabric softening composition is from 0.05% to 6%.
According to some embodiments of the fabric softening composition of the present invention, the mass percentage of component B in the fabric softening composition is from 0.05% to 5%.
According to some embodiments of the fabric softening compositions of the present invention, the composition further comprises component C; the component C comprises at least one of nonionic surfactant, thickener, perfume, antiseptic, bactericide, pigment, whitening agent, antioxidant and acid-base regulator.
According to some embodiments of the fabric softening compositions of the present invention, the fabric softening composition further comprises one or a combination of an acid-base modifier, a thickener.
According to some embodiments of the fabric softening composition of the present invention, the mass percentage of component C in the fabric softening composition is from 0.0001% to 20%.
According to some embodiments of the fabric softening composition of the present invention, the mass percentage of component C in the fabric softening composition is from 0.01% to 10%.
A third aspect of the present invention provides a method of preparing a fabric softening composition according to the second aspect of the present invention comprising the steps of: the components are mixed to obtain the fabric softening composition.
Some embodiments of the preparation method according to the invention comprise the following steps: and adding the component A and the component B into water, mixing and stirring to obtain the fabric softening composition.
According to some embodiments of the method of manufacture of the present invention, when the fabric softening composition further comprises component C, the method of manufacture comprises the steps of: and adding the component A and the component B into water, mixing and stirring, and then adding the component C, mixing and stirring to obtain the fabric softening composition.
A fourth aspect of the present invention provides the use of a fabric softening composition according to the second aspect of the present invention in a fabric softening process.
According to some embodiments of the application described herein, the fabric softening composition is formulated into a fabric softener for fabric softening treatment.
According to some embodiments of the inventive use, the fabric softening composition is a liquid fabric softener.
The beneficial effects of the invention are as follows:
1. the hydrolysis inhibitor provided by the invention can effectively inhibit the hydrolysis of the ester quaternary ammonium salt, so that the long-term storage stability of the fabric softening composition comprising the ester quaternary ammonium salt can be improved, and meanwhile, the compatibility of the formula is good.
2. The fabric softening composition is applied to fabric softening treatment, has good softening, antistatic and sterilizing effects, and is quite wide in application earlier stage.
Drawings
FIG. 1 is a graph of a sample with a score of 1 for fine particulate matter in a high temperature aged sample;
FIG. 2 is a graph of a sample with a fine particulate matter rating of 5 points in a high temperature aged sample.
Detailed Description
The embodiment of the invention provides a hydrolysis inhibitor of quaternary ammonium salt containing ester groups, which is an organic compound with the ClogP range of-1.37 & lt ClogP & lt 15 and containing functional groups capable of forming hydrogen bonds.
The n-octanol/water partition coefficient of an organic compound can reflect the migration ability of the organic compound between the aqueous phase and the organism, and is often characterized by a log P value. log p value refers to the logarithmic value of the ratio of partition coefficients of a substance in n-octanol (oil) and water. Reflecting the partitioning of the material in the oil/water phase. The greater the logP value, the more lipophilic the material; conversely, the smaller the more hydrophilic, i.e., the better the water solubility. logP can be calculated by the following formula:
logP＝log(Co/Cw) (2)
in formula (2), co: equilibrium concentration of a substance in n-octanol; and Cw: the equilibrium concentration of a substance in water.
The logP value can be obtained through experimental tests, and mainly comprises a direct method and an indirect method. The direct method comprises a shaking bottle method, a two-phase titration method and an extraction method; indirect methods include production column methods, chromatography. However, the experimental method has high cost and complicated testing operation, so that the calculation method is developed. The calculation method mainly comprises two steps, namely calculation through segment additivity of the organic compound and calculation through other physical and chemical parameters of the compound and internal connection of the compound and octanol/water distribution coefficient. The calculation method is used to obtain logP value, i.e. ClogP, which can make up the defect of experimental method, so that a large number of professional software such as CLOGP software, proLogP module of Pallas software, clogP/CMR module of SYBYL software and the like (Su Li, etc. compound lipid water distribution coefficient calculation software and comparative research [ J ]. University of Chinese medicine university report, 2008,39 (2): 178-182) are developed. The ClogP values of the hydrolysis inhibitors of the present invention can be calculated using software, such as Chemdraw.
In some embodiments of the invention, the ClogP range of the hydrolysis inhibitor is selected from: -0.05.ltoreq.ClogP.ltoreq.12, or-0.05.ltoreq.ClogP.ltoreq.11.40, or-0.05.ltoreq.ClogP.ltoreq.8.23, or-0.02.ltoreq.ClogP.ltoreq.12, or-0.02.ltoreq.ClogP.ltoreq.8.23, or-1.02.ltoreq.ClogP.ltoreq.12, or-1.02.ltoreq.ClogP.ltoreq.8.23, or-1.1.ltoreq.ClogP.ltoreq.12, or-1.1.ltoreq.ClogP.ltoreq.11.4, or-1.1.ltoreq.ClogP.ltoreq.8.23.
In some embodiments of the invention, the ClogP of the hydrolysis inhibitor may be-0.05, -0.02, 1.02, 1.10, 1.33, 1.40, 1.60, 1.61, 1.71, 2.04, 2.15, 2.40, 2.58, 2.61, 2.63, 2.75, 2.97, 3.20, 3.23, 3.25, 3.35, 3.52, 4.12, 5.06, 6.11, 7.17, 8.23, 9.29, 10.35, 11.40, or 12.
In some embodiments of the present invention, the functional group that can form hydrogen bonds includes at least one of a hydroxyl group, a carboxyl group, an aldehyde group, an amino group, and an ether bond. Namely, the hydrolysis inhibitor is an organic compound containing at least one of a hydroxyl group, a carboxyl group, an aldehyde group, an amino group and an ether bond.
In some embodiments of the invention, the hydrolysis inhibitor comprises at least one of an alcohol compound, a phenolic compound.
In some examples of the invention, the alcohol compound includes at least one of 2-methyl-2, 4-pentanediol, anisyl alcohol, benzyl alcohol, phenethyl alcohol, leaf alcohol, 2-hexenyl alcohol, cinnamyl alcohol, 3-phenylpropanol, dimethylbenzyl methanol, myrcenol, terpineol, linalool, geraniol, menthol, citronellol, tetrahydrolinalool, alpha-amyl cinnamyl alcohol, C12-C24 alcohol. The C12-C24 alcohol refers to fatty acid with carbon chain length of 12-24, such as one or more of dodecanol, tetradecanol, hexadecanol, octadecanol, icosanol, docosyl alcohol and tetracosanol.
In some examples of the invention, the phenolic compound comprises at least one of dimethyl hydroquinone, eugenol, isoeugenol, thymol, 3-methyl-4-isopropyl phenol, carvacrol.
Some specific examples of the alcohol compounds and the phenol compounds are given in tables 1 and 2, respectively. The hydrolysis inhibitor of embodiments of the present invention may be selected from one or more of the organic compounds in tables 1-2.
Table 1 alcohol examples
Raw material name CAS number ClogP
2-methyl-2, 4-pentanediol 107-41-5 -0.02
Aniline alcohol 123-11-5 1.02
Benzyl alcohol 100-51-6 1.10
Phenethyl alcohol 60-12-8 1.33
(Phyllol) 928-96-1 1.40
2-hexenol 2305-21-7 1.60
Cinnamic alcohol 104-55-2 1.61
3-phenylpropanol 122-97-4 1.71
Dimethylbenzyl methanol 100-86-7 2.04
Myrcenol 543-39-5 2.61
Terpineol (SONGYL) 10482-56-1 2.63
Linalool 78-70-6 2.75
Geraniol 106-24-1 2.97
Menthol 2216-51-5 3.23
Citronellol 106-22-9 3.25
Tetrahydrolinalool 78-69-3 3.52
Alpha-amyl cinnamic alcohol 101-85-9 4.12
Dodecanol (dodecanol) 112-53-8 5.06
Tetradecanol 112-72-1 6.11
Cetyl alcohol 36653-82-4 7.17
Stearyl alcohol 112-92-5 8.23
Eicosanol (icosanol) 629-96-9 9.29
Eicosdiol 661-19-8 10.35
Tetracosanol 506-51-4 11.40
Table 2 examples of phenolic compounds
Raw material name CAS number ClogP
Dimethyl hydroquinone 150-78-7 2.15
Eugenol 97-53-0 2.40
Isoeugenol 97-54-1 2.58
Thymol 89-83-8 3.20
Carvacrol 499-75-2 3.35
The embodiment of the invention also provides a fabric softening composition, which comprises the following components:
component A: quaternary ammonium salt containing ester group;
component B: hydrolysis inhibitor
And water.
The components of the fabric softening compositions of the examples of the present invention are described in further detail below:
1. component A
In the fabric softening composition of the present invention, component a is an ester group containing quaternary ammonium salt. In some embodiments, the structural formula of the quaternary ammonium salt containing ester group is shown in formula (1):
in the formula (1), R 1 Selected from C11-C23 substituted or unsubstituted aliphatic hydrocarbon groups, said substituted groups being selected from-OH, phenyl or- (CH) 2 CH 2 O) m ；m＝1～10；
R 2 、R 3 May be the same OR different and are each independently selected from the group consisting of-C (O) OR, -OC (O) R, -C (O) O (CH) 2 CH 2 O) n R, benzyl, phenyl, -OH or H, wherein R is selected from C10-C22 branched or straight chain alkyl; n=1 to 10;
R 4 selected from-OH or H;
b is selected from integers from 1 to 5;
when R is 2 、R 3 、R 4 When H, c, d and e can be the same or different and are respectively and independently selected from integers of 0-3;
when R is 2 、R 3 、R 4 When the three groups are not H, c, d and e can be the same or different and are respectively and independently selected from integers of 1-3;
x is an anion of valence a, X -a Selected from Br - 、Cl - 、CH 3 SO 4 - Or CH 3 CH 2 SO 4 - 。
In some embodiments of the invention, the quaternary ammonium salt containing ester groups comprises the reaction product of a fatty amine, a fatty acid/oil, and an alkylating agent. For example, fatty amine and fatty acid/grease are subjected to esterification reaction to obtain amine ester; and carrying out quaternization reaction on the amine ester and an alkylating agent to obtain the ester quaternary ammonium salt. Depending on the fatty amine selected, the final reaction product may also have one or more of a mixture of monoester-, diester-, and triester-linked compounds. If the fatty amine is triethanolamine, the final reaction product is a mixture of monoester, diester, or triester compounds. In some embodiments of the invention, the fatty amine comprises at least one of methyldiethanolamine, dimethylethanolamine, triethanolamine.
In some embodiments of the invention, the fatty acid comprises a saturated or unsaturated fatty acid, a fatty acid with or without hydroxyl groups. Wherein the carbon chain length of the fatty acid may be selected from the group consisting of C12 to C22. For example, at least one selected from hexadecanoic acid, octadecanoic acid and oleic acid.
In some embodiments of the present invention, the alkylating agent includes at least one of dimethyl sulfate, diethyl sulfate, methyl chloride, methyl bromide.
In the fabric softening composition of the embodiment of the invention, the mass percentage of the quaternary ammonium salt containing ester groups is 0.5-25%, preferably 0.1-20%, more preferably 1-15%, and even more preferably 1-10%.
2. Component B
In the fabric softening compositions of the present invention, component B is a hydrolysis inhibitor. The hydrolysis inhibitor according to the embodiment of the present invention is the hydrolysis inhibitor according to the foregoing embodiment.
In the fabric softening composition according to the embodiment of the present invention, the hydrolysis inhibitor is 0.05% to 10% by mass, preferably 0.05% to 6% by mass, more preferably 0.05% to 5% by mass, still more preferably 0.1% to 2% by mass, and still more preferably 0.15% to 0.75% by mass.
3. Component C
The fabric softening compositions of embodiments of the present invention may also include other components, namely component C. Component C may include at least one of nonionic surfactants, thickeners, fragrances, preservatives, bactericides, pigments, whiteners, antioxidants, acid-base modifiers.
In the fabric softening composition of the embodiment of the present invention, the mass percentage of component C in the fabric softening composition is 0.0001% to 20%, preferably 0.01% to 10%.
3.1 nonionic surfactants
In some embodiments of the invention, the nonionic surfactant hydrophobic moiety comprises hydrocarbon chains derived from natural oils and petrochemical sources, and the hydrophilic moiety comprises polyoxyethylene groups, polyol (hydroxy) groups, in addition to alcohol amides, amine oxides, and the like. The hydrophobic raw materials for preparing the nonionic surfactant mainly comprise fatty alcohols (including natural alcohols and synthetic alcohols), alkylphenols, fatty acids, fatty amines, propylene oxide and the like; the hydrophilic raw materials mainly comprise ethylene oxide, polyalcohol, glucose and the like. The nonionic surfactant may include one or more of C6-C22 alkyl alcohol polyoxyethylene ethers (eo=1-70); alkoxy block copolymers, such as ethoxy/propoxy block copolymers; one or more of C6-22 alkylamine polyoxyethylene ether (eo=1-70), C8-22 alkylamide polyoxyethylene ether (eo=5-50); one or more of C6-C22 alkyl acid polyoxyethylene ethers (eo=1-70); alkyl glycosides; amine oxide surfactants.
If a nonionic surfactant is used, the mass percent of nonionic surfactant in the fabric softening composition is typically from 0.01% to 5%, preferably from 0.02% to 4%.
3.2 thickening agents
The fabric softening compositions of the embodiments of the present invention may optionally be viscosity-adjusting with or without the addition of a thickener, depending on the application requirements. Suitable thickeners include nonionic and cationic, amphoteric polymers such as at least one of hydrophobically modified cellulose ethers, cationically modified starches, copolymers of methacrylates and acrylamides, amphoteric polymers of acrylates and ethyl acrylate trimethylammonium chloride, polyacrylamides.
If a thickener is used, the weight percent of thickener in the fabric softening composition is typically from 0.01% to 5%, preferably from 0.1% to 5%, more preferably from 0.2% to 1.0%.
3.3 fragrances
In some embodiments of the invention, the perfume is selected from at least one of the following: herbal scents, such as peppermint, spearmint, rosemary, thyme; fruit flavors such as apple, almond, grape, cherry, pineapple, pear, juicy peach, mango, orange, strawberry, blueberry, citrus; floral agents, such as rose-like, lavender-like, carnation-like; and vanilla, gardenia, hawthorn, vanilla, honeysuckle, cyclamen, hyacinth, fern, clove, jasmine, lily, mimosa, magnolia, orchid, narcissus, orange, licorice, luteolin, clover, violet, sweet pea, and cinquefoil.
In other embodiments of the present invention, the perfume may also be selected from microencapsulated fragrances. The microcapsule perfume comprises a shell and a perfume oil core enclosed in the shell, and the perfume oil is released from the microcapsule substantially until the shell breaks due to mechanical forces (such as friction). The perfume oil will therefore not volatilize into the surrounding air for a longer period of time. When added to a fabric softening composition, the microcapsule perfume is deposited onto the fabric during the wash or rinse cycle. Thus, the microencapsulated perfume that is deposited on the fabric releases perfume upon breakage. The shell of the microcapsule perfume preferably comprises the following materials: aminoplasts, polyacrylates, polyethylenes, polyamides, polystyrenes, polyisoprenes, polycarbonates, polyesters, polyolefins, polysaccharides (such as alginates), gelatins, shellac, epoxy resins, vinyl polymers, silicones, and combinations thereof.
If perfumes are used, the mass percent of perfume in the fabric softening composition is typically from 0.01% to 5%, preferably from 0.05% to 2%.
3.4 preservative
In some embodiments of the invention, the preservative is selected from the group consisting of one or more of pinacolin (a mixture of 2-methyl-4-isothiazolin-3-one and 5-chloro-2-methyl-4-isothiazolin-3-one), 2-methyl-4-isothiazolin-3-one, 5-chloro-2-methyl-4-isothiazolin-3-one, methyl benzoate, ethyl benzoate, propyl benzoate, jin Yibing esters of nipen, butyl benzoate, jin Yi butyl benzoate, 3-iodo-2-propynylbutylcarbamate, dimethylol hydantoin, bloodl.
If a preservative is used, the mass percent of preservative in the fabric softening composition is typically from 0.001% to 1%, preferably from 0.01% to 0.2%.
3.5 bactericides
In some embodiments of the present invention, the germicides are selected from at least one of decyl/dodecyl/tetradecyl trimethyl ammonium chloride, dioctyl/didecyl/didodecyl dimethyl ammonium chloride, dodecyl dimethyl benzyl ammonium chloride, polyoxyethylene trimethyl ammonium chloride, silicone quaternary ammonium salts, 3-methyl-4-isopropyl phenol, p-chloro-m-xylenol (PCMX), triclosan, 1' -hexamethylenebis [5- (4-azobenzene) ] biguanide hydrochloride, polyhexamethylene biguanide hydrochloride, chlorhexidine acetate, chlorhexidine gluconate, chitosan quaternary ammonium salts, sodium benzoate, potassium sorbate, silver ion germicides.
If a biocide is used, the biocide is typically present in the fabric softening composition in an amount of from 0.01% to 3%, preferably from 0.1% to 2%.
3.6 pigments
In some embodiments of the invention, the pigment may be selected from pigments and/or dyes, and may include pigments commonly used in laundry detergents or fabric softeners.
If pigments are used, the pigment content of the fabric softening composition is generally from 0.0001% to 0.5%, preferably from 0.001% to 0.1%.
3.7 whitening agents
In some embodiments of the invention, the whitening agent is a fluorescent whitening agent, such as at least one selected from the group consisting of stilbene biphenyl fluorescent whitening agent, triazinylamino stilbene fluorescent whitening agent, bis (1, 2, 3-triazol-2-yl) stilbene fluorescent whitening agent, bis (benzofuran-2-yl) biphenyl, 1, 3-diphenyl-2-pyrazoline, coumarin fluorescent whitening agent; preferably, the fluorescent whitening agents are both sulphonated products, in the form of their alkali metal salts, including but not limited to stilbene based compounds, such as at least one of 4,4' -bis (2-sodium sulphonated styryl) biphenyl, bis-triazinyl stilbene derivatives.
If a whitening agent is used, the weight percentage of whitening agent in the fabric softening composition is typically from 0.001% to 0.5%, preferably from 0.005% to 0.3%.
3.8 antioxidants
In some embodiments of the invention, the antioxidant is selected from at least one of ascorbic acid, 2, 6-di-tert-butyl-4-methyl phenol (BHT), butyl Hydroxyanisole (BHA), tocopherol, propyl gallate.
If an antioxidant is used, the weight percentage of antioxidant in the fabric softening composition is generally from 0.01% to 2%, preferably from 0.01% to 1%.
3.9 acid-base modifier
Acid-base modifiers, also known as pH modifiers, may be used with alkalinity sources of inorganic and/or organic type as well as acidifying agents.
In some embodiments of the present invention, the inorganic alkalinity source may be selected from one of sodium hydroxide, potassium hydroxide, or a combination thereof; the organic alkalinity source can be selected from one or a combination of monoethanolamine and triethanolamine; the inorganic acidulant can be at least one selected from HF, HCl, HBr, HI, boric acid, phosphoric acid, phosphonic acid, sulfuric acid and sulfonic acid; the organic acidulant may be at least one selected from citric acid, C1 to C30 carboxylic acids.
The pH of the fabric softening compositions of the embodiments of the present invention is adjusted by the addition of an acid-base modifier. Preferably, the pH of the fabric softening composition is adjusted to 2 to 5 by adding an acid-base modifier; further preferably, the pH of the fabric softening composition is adjusted to 2 to 4 by adding an acid-base modifier; still further preferably, the pH of the fabric softening composition is adjusted to 2 to 3 by the addition of an acid-base modifier; still more preferably, the pH of the fabric softening composition is adjusted to 2.5 to 2.7 by the addition of an acid-base modifier.
4. Water and its preparation method
The fabric softening composition of the present embodiment has the balance of water in addition to the above components.
The fabric softening composition of the present invention is prepared by simply mixing the components.
In some embodiments of the present invention, when the fabric softening composition comprises component a, component B and water, the method of making the fabric softening composition comprises the steps of: the component A and the component B are added into water, mixed and stirred to prepare the fabric softening composition.
In some embodiments of the invention, the water is heated to 30 ℃ to 85 ℃ prior to addition of component a and component B. In some examples, the water is heated to 65 ℃.
In some embodiments of the present invention, component A and component B are added to water and mixed for a period of 1min to 100min. In some examples, the mixing is for a period of 20 minutes.
In other embodiments of the present invention, when the fabric softening composition comprises component C in addition to component a, component B and water, the method of making the fabric softening composition comprises the steps of: the component A and the component B are added into water to be mixed and stirred, and then the component C is added to be mixed and stirred, so that the fabric softening composition is prepared.
In some embodiments of the present invention, when the fabric softening composition comprises component a, component B, component C and water, the reaction solution is prepared at a temperature of from 30 ℃ to 50 ℃. In some examples, the reaction solution temperature is 40 ℃.
In some embodiments of the invention, component C is added and mixed for a period of 1min to 100min. In some examples, component C is added for a mixing period of 10 minutes.
The fabric softening composition provided by the embodiment of the invention can be made into a fabric softener, such as a liquid fabric softener, and then applied to softening treatment of fabrics.
The present invention will be described in further detail with reference to specific examples. The starting materials, reagents or apparatus used in the examples and comparative examples were either commercially available from conventional sources or may be obtained by prior art methods unless specifically indicated. Unless otherwise indicated, assays or testing methods are routine in the art.
The test method of the invention is described as follows:
1. acid value
The hydrolysis inhibitor can be used for representing the hydrolysis effect of reducing the ester quaternary ammonium salt by measuring the acid value reduction value of a fresh sample and a high-temperature aged sample. The smaller the acid value decrease value, the better the hydrolysis-inhibiting effect.
The acid value test method refers to GB/T9104-2008 industrial stearic acid test method, and the experimental operation is as follows: 3g of the sample is weighed, dissolved in 30mL of isopropanol, 3-4 drops of phenolphthalein indicator are added, and immediately titrated to light pink with 0.1mol/L potassium hydroxide standard solution and the color is kept for 15s as an end point.
The acid value calculation formula is:
in the formula (3):
c-concentration of potassium hydroxide standard solution, mol/L;
v-consume volume of potassium hydroxide standard solution, mL;
56.1-molar mass of potassium hydroxide, g/mol;
m-sample mass, g.
Acid value decrease value (mgKOH/g) the formula was = acid value of high temperature aged sample-acid value of fresh sample.
The high-temperature aging condition tested by the invention is aging at 85 ℃ for 120 hours.
2. Conditions of fine particles in high temperature aged samples
If the esterquat is hydrolyzed, fine particles can be observed in the sample, and the more obvious the hydrolysis degree is, the more fine particles are. The degree of hydrolysis was scored semi-quantitatively by visual inspection of the amount of fine particulate matter.
The scores were made 1 to 5, the higher the score, the more fine particles. Wherein 1 denotes that no fine particulate matter is substantially observed; a score of 5 indicates that a large amount of fine particulate matter was observed.
The specific operation method of scoring is as follows:
the sample aged for 120 hours at 85 ℃ is cooled to room temperature, and the operation method of the dispersibility of QB/T4535-2013 fabric softener is referred to as follows: about 0.5g of the sample was weighed, placed in a 300mL beaker, 200mL of hard water (250 ppm) was added, stirred for 1min at 400r/min using a standard four-blade propeller, and observed in a well-lighted environment.
In the following examples or comparative examples, the ester-based quaternary ammonium salt used was commercially available under the trade name REWQUAT WE 28SH, and the main component was ethyl dipalmitate-based hydroxyethyl methyl ammonium methyl sulfate. The aqueous solution of the esterquat salt used had a pH of about 3. AQUAGEL C45 is used as a thickener.
Unless otherwise specified, the samples of the examples and comparative examples of the present invention were prepared by mixing and stirring the respective components with water according to the formulation composition in the following table, referring to the preparation method of the previous examples, and adjusting the ph=2.5 to 2.7 of the composition with an appropriate amount of citric acid.
Table 3 shows the formulation compositions and test results of comparative example 1 and examples 1 to 6.
Table 3 formulation compositions and test results for comparative example 1 and examples 1 to 6
As is clear from comparative example 1 and examples 1 to 2 in Table 3, the addition of stearyl alcohol or mixed carbon C16/18 alcohol, both of which had smaller acid value decreases the acid value of the sample from 3.41mgKOH/g to about 2.6mgKOH/g. As is clear from examples 3 to 5, when 0.15% to 0.6% of menthol was added, the acid value decreased more as the amount of menthol added increased. In example 6, the mixed carbon C16/18 alcohol and menthol are compounded, so that the synergistic effect is further generated, and the acid value is further reduced.
Figures 1 and 2 show sample plots of the fine particulate matter condition scores of 1 minute and 5 minutes, respectively, in the high temperature aged samples. From fig. 1 it can be seen that substantially no fine particulate matter is observed in the sample, whereas from fig. 2 it can be seen that there is a large amount of fine particulate matter in the sample. As can also be seen from the scoring results of the fine particles in the high temperature aged samples in Table 3, comparative example 1 has more pronounced hydrolysis of the fine particles, as shown in FIG. 2; substantially no fine particulate matter was observed in examples 1-6, as shown in fig. 1.
Therefore, based on the test result of comparative example 1, the present invention judges the test data that the acid value decrease value is smaller than that of the corresponding comparative example as having the effect of suppressing hydrolysis of the esterquat.
Table 4 shows the formulation compositions and test results of comparative examples 2 to 5 and examples 7 to 10, and Table 5 shows the formulation compositions and test results of examples 11 to 14.
Table 4 formulation compositions and test results of comparative examples 2 to 5 and examples 7 to 10
Table 5 formulation compositions and test results for examples 11 to 14
From tables 4-5, the effect of hydrolysis inhibitors of different ClogP values on reducing the rate of hydrolysis of esterquats can be compared:
comparative examples 4 and 5 were added glycerol having a ClogP of-1.54 and ethylene glycol having a ClogP of-1.37, respectively, and as can be seen from table 4, the two samples had substantially no hydrolysis-inhibiting effect, and the acid value was reduced to substantially equivalent to that of comparative example 1. Example 7 was a 2-methyl-2, 4-pentanediol with a ClogP value of-0.02, which had a certain hydrolysis inhibiting effect. It can be seen from examples 8 to 10 that when the addition amount of the hydrolysis inhibitor is the same, the inhibition effect tends to increase as the ClogP thereof increases.
In comparative example 2, ethyl heptanoate having a ClogP of 3.36 was added, and in comparative example 3, isobutyl phenylacetate having a ClogP of 3.28 was added, and both of which have a ClogP equivalent to that of thymol and carvacrol, but have no hydrolysis-inhibiting effect, so that it was considered necessary to contain a functional group capable of forming a hydrogen bond in the hydrolysis inhibitor.
As can also be seen from the results of the fine particle scoring of the high temperature aged samples, comparative examples 2 to 5 have more pronounced hydrolyzed fine particles, example 7 has very small amounts of fine particles, and examples 8 to 16 have substantially no observed fine particles.
Table 6 shows the formulation compositions and test results of comparative example 6 and examples 15 to 16.
Table 6 formulation compositions and test results for comparative example 6 and examples 15 to 16
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As can be seen from comparative example 6 and examples 15 to 16 of Table 6, the effect of inhibiting hydrolysis of esterquat was similarly achieved by adding menthol or thymol to the sample group to which no thickener AQUAGEL C45 was added.
The test results show that the hydrolysis inhibitor with the technical characteristics of-1.37 & lt ClogP & lt 15 and containing the functional groups capable of forming hydrogen bonds can effectively inhibit the hydrolysis of the quaternary ammonium salt containing ester groups, and meanwhile, the formula compatibility is good, so that the stability of the product in long-term placement can be improved.
Samples of examples and comparative examples were taken for fabric softening treatment testing as follows:
the fabric material: knitted pure cotton white towels, size 24 x 24cm, each towel weighing about 30g.
Pretreatment: the towel for softness performance test needs to be pretreated to remove the soft finishing agent when leaving the factory. The pretreatment method comprises the steps of putting the knitted towel into a standard washing machine, washing the knitted towel for 3 times by using 20 weight percent of sodium dodecyl alcohol ether sulfate (sodium hydroxide is used for adjusting the pH stock solution to about 8.5) basic detergent according to the standard washing program of the washing machine, rinsing the knitted towel according to a rinsing-dehydrating mode, repeatedly rinsing the knitted towel until no foam exists, drying the knitted towel, taking the knitted towel out, and hanging the knitted towel at room temperature for airing.
Sample treatment: the washing process of the drum washing machine comprises the following steps:
1.2kg of fabric (10 knitted pure cotton white towels, not heavy, weight complement with pure cotton cloth) +30g of standard laundry detergent +40g of softener + mixing procedure; and after the washing is finished, taking out the towel, and naturally airing.
Evaluation of softening Properties: 10 trained evaluators were selected for hand feel evaluation. The softness score was scored from 0 to 5, 10 panelists evaluated 1 time each, and the scores of 10 times averaged, with higher scores representing better softness performance, and test results shown in table 7.
Table 7 results of evaluation of softening Properties of comparative example 1 and example 5
Sample name Softness performance score
Comparative example 1 3.75
Example 5 3.85
From the results of Table 7, it is understood that the samples of example 5 and comparative example 1 each have a good softening effect and are well suited for use in softening treatment of fabrics.
The above examples are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above examples, and any other changes, modifications, substitutions, combinations, and simplifications that do not depart from the spirit and principle of the present invention should be made in the equivalent manner, and the embodiments are included in the protection scope of the present invention.

Claims (5)

1. A fabric softening composition comprising the following components:
component A: quaternary ammonium salt containing ester group;
component B: a hydrolysis inhibitor;
component C: the component C is an acid-base regulator or at least one of an acid-base regulator, a nonionic surfactant, a thickener, a spice, a preservative, a bactericide, a pigment, a whitening agent and an antioxidant;
water;
the pH value of the fabric softening composition is 2-4;
wherein the hydrolysis inhibitor is an organic compound which has a ClogP ranging from 1.02 to 12 and contains a functional group capable of forming a hydrogen bond; the hydrolysis inhibitor comprises at least one of an alcohol compound and a phenolic compound; the mass percentage of the component A in the fabric softening composition is 0.5% -25%; the mass percentage of the component B in the fabric softening composition is 0.05% -10%.
2. A fabric softening composition according to claim 1 wherein the hydrolysis inhibitor comprises at least one of anisyl alcohol, benzyl alcohol, phenethyl alcohol, leaf alcohol, 2-hexenyl alcohol, cinnamyl alcohol, 3-phenylpropanol, dimethylbenzyl methanol, myrcenol, terpineol, linalool, geraniol, menthol, citronellol, tetrahydrolinalool, alpha-amyl cinnamyl alcohol, C12-C24 alcohol, dimethyl hydroquinone, eugenol, isoeugenol, thymol or an isomer thereof, carvacrol.
3. A fabric softening composition according to claim 1 wherein the quaternary ammonium salt containing ester groups has the structural formula (1):
（1）
in the formula (1), R 1 Selected from C11-C23 substituted or unsubstituted aliphatic hydrocarbon groups, said substituted groups being selected from-OH, phenyl or- (CH) 2 CH 2 O) m ；m=1~10；
R 2 、R 3 May be the same OR different and are each independently selected from the group consisting of-C (O) OR, -OC (O) R, -C (O) O (CH) 2 CH 2 O) n R, benzyl, phenyl, -OH or H, wherein R is selected from C10-C22 branched or straight-chain alkyl; n=1 to 10;
R 4 selected from-OH or H;
b is selected from integers from 1 to 5;
when R is 2 、R 3 、R 4 When H, c, d and e can be the same or different and are respectively and independently selected from integers of 0-3;
when R is 2 、R 3 、R 4 When the three groups are not H, c, d and e can be the same or different and are respectively and independently selected from integers of 1-3;
x is an anion of valence a, X -a Selected from Br - 、Cl - 、CH 3 SO 4 - Or CH 3 CH 2 SO 4 - 。
4. A process for preparing a fabric softening composition according to any one of claims 1 to 3, comprising the steps of: the components are mixed to obtain the fabric softening composition.
5. Use of a fabric softening composition according to any one of claims 1 to 3 in a fabric softening process.
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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4840738A (en) * 1988-02-25 1989-06-20 The Procter & Gamble Company Stable biodegradable fabric softening compositions containing 2-hydroxypropyl monoester quaternized ammonium salts
JP2006161229A (en) * 2004-12-09 2006-06-22 Kao Corp Transparent or translucent liquid softener composition
JP2011132639A (en) * 2009-12-25 2011-07-07 Kao Corp Softener composition for clothing
JP2016121423A (en) * 2014-12-25 2016-07-07 花王株式会社 Liquid softener composition
JP2017082357A (en) * 2015-10-28 2017-05-18 ライオン株式会社 Liquid softening agent composition
JP2017172051A (en) * 2016-03-18 2017-09-28 花王株式会社 Liquid softener composition

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4840738A (en) * 1988-02-25 1989-06-20 The Procter & Gamble Company Stable biodegradable fabric softening compositions containing 2-hydroxypropyl monoester quaternized ammonium salts
JP2006161229A (en) * 2004-12-09 2006-06-22 Kao Corp Transparent or translucent liquid softener composition
JP2011132639A (en) * 2009-12-25 2011-07-07 Kao Corp Softener composition for clothing
JP2016121423A (en) * 2014-12-25 2016-07-07 花王株式会社 Liquid softener composition
JP2017082357A (en) * 2015-10-28 2017-05-18 ライオン株式会社 Liquid softening agent composition
JP2017172051A (en) * 2016-03-18 2017-09-28 花王株式会社 Liquid softener composition

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