CN115418853A - Hydrolysis inhibitor containing esterquat and fabric softening composition - Google Patents
Hydrolysis inhibitor containing esterquat and fabric softening composition Download PDFInfo
- Publication number
- CN115418853A CN115418853A CN202211037676.9A CN202211037676A CN115418853A CN 115418853 A CN115418853 A CN 115418853A CN 202211037676 A CN202211037676 A CN 202211037676A CN 115418853 A CN115418853 A CN 115418853A
- Authority
- CN
- China
- Prior art keywords
- fabric softening
- softening composition
- hydrolysis inhibitor
- component
- alcohol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000004744 fabric Substances 0.000 title claims abstract description 99
- 239000000203 mixture Substances 0.000 title claims abstract description 93
- 230000007062 hydrolysis Effects 0.000 title claims abstract description 65
- 238000006460 hydrolysis reaction Methods 0.000 title claims abstract description 65
- 239000003112 inhibitor Substances 0.000 title claims abstract description 48
- -1 ester quaternary ammonium salt Chemical class 0.000 claims abstract description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 125000000524 functional group Chemical group 0.000 claims abstract description 10
- 150000002894 organic compounds Chemical group 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 18
- 238000002156 mixing Methods 0.000 claims description 14
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 claims description 13
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 claims description 11
- 239000002562 thickening agent Substances 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 claims description 9
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims description 9
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- VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-Phenyl-1-propanol Chemical compound OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 claims description 8
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- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 claims description 8
- BJIOGJUNALELMI-ONEGZZNKSA-N Isoeugenol Natural products COC1=CC(\C=C\C)=CC=C1O BJIOGJUNALELMI-ONEGZZNKSA-N 0.000 claims description 8
- 125000004185 ester group Chemical group 0.000 claims description 8
- 229940041616 menthol Drugs 0.000 claims description 8
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims description 7
- 239000003963 antioxidant agent Substances 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
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- 230000003078 antioxidant effect Effects 0.000 claims description 6
- RECUKUPTGUEGMW-UHFFFAOYSA-N carvacrol Chemical compound CC(C)C1=CC=C(C)C(O)=C1 RECUKUPTGUEGMW-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 230000002335 preservative effect Effects 0.000 claims description 6
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- ZCHHRLHTBGRGOT-SNAWJCMRSA-N (E)-hex-2-en-1-ol Chemical compound CCC\C=C\CO ZCHHRLHTBGRGOT-SNAWJCMRSA-N 0.000 claims description 5
- OHBQPCCCRFSCAX-UHFFFAOYSA-N 1,4-Dimethoxybenzene Chemical compound COC1=CC=C(OC)C=C1 OHBQPCCCRFSCAX-UHFFFAOYSA-N 0.000 claims description 5
- DLHQZZUEERVIGQ-UHFFFAOYSA-N 3,7-dimethyl-3-octanol Chemical compound CCC(C)(O)CCCC(C)C DLHQZZUEERVIGQ-UHFFFAOYSA-N 0.000 claims description 5
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- 239000003899 bactericide agent Substances 0.000 claims description 5
- HHTWOMMSBMNRKP-UHFFFAOYSA-N carvacrol Natural products CC(=C)C1=CC=C(C)C(O)=C1 HHTWOMMSBMNRKP-UHFFFAOYSA-N 0.000 claims description 5
- 235000007746 carvacrol Nutrition 0.000 claims description 5
- WYXXLXHHWYNKJF-UHFFFAOYSA-N isocarvacrol Natural products CC(C)C1=CC=C(O)C(C)=C1 WYXXLXHHWYNKJF-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- DUNCVNHORHNONW-UHFFFAOYSA-N myrcenol Chemical compound CC(C)(O)CCCC(=C)C=C DUNCVNHORHNONW-UHFFFAOYSA-N 0.000 claims description 5
- 150000002989 phenols Chemical class 0.000 claims description 5
- 230000002087 whitening effect Effects 0.000 claims description 5
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 claims description 4
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 claims description 4
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 claims description 4
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 claims description 4
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- 125000003172 aldehyde group Chemical group 0.000 claims description 4
- OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 claims description 4
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- 125000003277 amino group Chemical group 0.000 claims description 4
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 235000000484 citronellol Nutrition 0.000 claims description 4
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 claims description 4
- BXJGUBZTZWCMEX-UHFFFAOYSA-N dimethylhydroquinone Natural products CC1=C(C)C(O)=CC=C1O BXJGUBZTZWCMEX-UHFFFAOYSA-N 0.000 claims description 4
- 229960002217 eugenol Drugs 0.000 claims description 4
- 229940113087 geraniol Drugs 0.000 claims description 4
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- 229930008383 myrcenol Natural products 0.000 claims description 4
- 229940116411 terpineol Drugs 0.000 claims description 4
- BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 claims description 4
- LIPHCKNQPJXUQF-SDNWHVSQSA-N 2-Benzylidene-1-heptanol Chemical compound CCCCC\C(CO)=C/C1=CC=CC=C1 LIPHCKNQPJXUQF-SDNWHVSQSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000001450 anions Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 3
- 235000013599 spices Nutrition 0.000 claims description 3
- 239000001418 (2E)-2-benzylideneheptan-1-ol Substances 0.000 claims description 2
- JESIHYIJKKUWIS-UHFFFAOYSA-N 1-(4-Methylphenyl)ethanol Chemical compound CC(O)C1=CC=C(C)C=C1 JESIHYIJKKUWIS-UHFFFAOYSA-N 0.000 claims description 2
- MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 claims description 2
- 229940090971 alpha-amylcinnamyl alcohol Drugs 0.000 claims description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 claims 1
- BJIOGJUNALELMI-ARJAWSKDSA-N cis-isoeugenol Chemical compound COC1=CC(\C=C/C)=CC=C1O BJIOGJUNALELMI-ARJAWSKDSA-N 0.000 claims 1
- 230000007774 longterm Effects 0.000 abstract description 6
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- 230000001954 sterilising effect Effects 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 25
- 238000000034 method Methods 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 17
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 239000002304 perfume Substances 0.000 description 13
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- 150000004665 fatty acids Chemical class 0.000 description 11
- 239000013618 particulate matter Substances 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 10
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- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 8
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- 239000010419 fine particle Substances 0.000 description 8
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- 239000002979 fabric softener Substances 0.000 description 7
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 7
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 235000006708 antioxidants Nutrition 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 6
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- 239000002168 alkylating agent Substances 0.000 description 5
- 229940100198 alkylating agent Drugs 0.000 description 5
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- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000001585 thymus vulgaris Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 229960003500 triclosan Drugs 0.000 description 1
- CEYYIKYYFSTQRU-UHFFFAOYSA-M trimethyl(tetradecyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)C CEYYIKYYFSTQRU-UHFFFAOYSA-M 0.000 description 1
- OTRQTVHWMPQPOJ-UHFFFAOYSA-N trimethyl-(prop-2-enoylamino)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)NC(=O)C=C OTRQTVHWMPQPOJ-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
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- 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
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- 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
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- D06M13/144—Alcohols; Metal alcoholates
- D06M13/148—Polyalcohols, e.g. glycerol or glucose
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Abstract
The invention discloses a hydrolysis inhibitor containing ester quaternary ammonium salt and a fabric softening composition. The hydrolysis inhibitor is an organic compound having a ClogP in the range-1.37 < ClogP < 15 and containing a functional group capable of forming a hydrogen bond. The invention also provides a fabric softening composition comprising the hydrolysis inhibitor and an esterquat. The hydrolysis inhibitor provided by the invention can effectively inhibit the hydrolysis of the esterquat, thereby improving the long-term storage stability of the fabric softening composition containing the esterquat and having good compatibility of the formula. The fabric softening composition is applied to fabric softening treatment, has good softening, antistatic and sterilizing effects and is very wide in the early stage of application.
Description
Technical Field
The invention relates to the technical field of daily chemical technology, in particular to a hydrolysis inhibitor containing ester quaternary ammonium salt and a fabric softening composition.
Background
Ester group-containing quaternary ammonium salts are widely used for preparing fabric softeners because of their easy biodegradability. However, the quaternary ammonium salt containing ester groups also has natural defects, the ester groups are easy to hydrolyze, obvious fine particles are separated out from the product in long-term storage, and obvious thickening phenomenon occurs, even the quaternary ammonium salt cannot be used continuously. The problem of hydrolysis is particularly pronounced when stored at different temperatures, especially at elevated temperatures, such as 40-90 ℃.
The prior art discloses a fabric treatment composition containing periodate. Periodate may inhibit hydrolysis of quaternary ammonium salts containing ester groups. However, periodate also has the obvious drawback of being too oxidizing to negatively affect other components of the composition, such as discoloration of pigments, discoloration of perfumes, off-tastes, and the like.
Therefore, how to inhibit the hydrolysis of the ester-containing quaternary ammonium salt and improve the long-term storage stability of the product is still a technical problem which needs to be solved urgently.
Disclosure of Invention
The present invention is directed to solving at least one of the above problems in the prior art. Therefore, one object of the present invention is to provide a hydrolysis inhibitor containing an esterquat, another object of the present invention is to provide a fabric softening composition, a third object of the present invention is to provide a method for preparing the fabric softening composition, and a fourth object of the present invention is to provide the use of the fabric softening composition in fabric softening treatment.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
in a first aspect of the present invention, there is provided a hydrolysis inhibitor comprising an esterquat, said hydrolysis inhibitor being an organic compound having a ClogP in the range-1.37 < ClogP < 15 and comprising a functional group capable of forming a hydrogen bond.
The inventors have found that when a compound having-1.37 < ClogP < 15 and having a hydrogen bond-forming functional group is used as a hydrolysis inhibitor, hydrolysis of the esterquat-containing compound can be effectively inhibited, and long-term storage stability of a composition comprising the esterquat-containing compound can be improved, and the composition is safer for other components and has better compatibility.
According to some embodiments of the hydrolysis inhibitor of the present invention, the hydrolysis inhibitor has a ClogP range of: -0.05. Ltoreq. ClogP. Ltoreq.12.
According to some embodiments of the hydrolysis inhibitor of the present invention, the functional group capable of forming a hydrogen bond includes at least one of a hydroxyl group, a carboxyl group, an aldehyde group, an amino group, and 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 and 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, anethol, benzyl alcohol, phenethyl alcohol, folyl alcohol, 2-hexenol, cinnamyl alcohol, 3-phenylpropanol, dimethylbenzyl alcohol, myrcenol, terpineol, linalool, geraniol, menthol, citronellol, tetrahydrolinalool, alpha-pentylcinnamic alcohol, C12-C24 alcohols, dimethylhydroquinone, eugenol, isoeugenol, thymol or an isomer thereof (e.g., 3-methyl-4-isopropylphenol), carvacrol.
In a second aspect the present invention provides a fabric softening composition comprising the following components:
and (2) component A: ester-containing quaternary ammonium salts;
and (B) component: a hydrolysis inhibitor according to the first aspect of the 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 composition of the present invention, the esterquat has the formula (1):
in the formula (1), R 1 Is selected from C11-C23 substituted or unsubstituted aliphatic hydrocarbon group, and the substituted group is selected from-OH, phenyl or- (CH) 2 CH 2 O) m ；m＝1～10；
R 2 、R 3 Can be the same OR different and are respectively and independently selected from-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 is selected from-OH or H;
b is an integer from 1 to 5;
when R is 2 、R 3 、R 4 When the hydrogen is 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 not H, c, d and e may be the same or different and are each independently selected from integers of 1 to 3;
x is an anion of valency a, X -a Is selected from Br - 、Cl-、CH 3 SO 4 - Or CH 3 CH 2 SO 4 - 。
According to some embodiments of the fabric softening composition 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 containing or not containing hydroxyl; the alkylating agent comprises at least one of dimethyl sulfate, diethyl sulfate, methyl chloride and methyl bromide. Wherein the carbon chain length of the fatty acid can be selected from C12-C22.
According to some embodiments of the fabric softening composition of the present invention, the component a is present in an amount of 0.1% to 20% by weight of the fabric softening composition.
According to some embodiments of the fabric softening composition of the present invention, the component a is present in the fabric softening composition in an amount of 1% to 15% by weight.
According to other embodiments of the fabric softening composition of the present invention, the component a is present in the fabric softening composition in an amount of 1% to 10% by weight.
According to some embodiments of the fabric softening composition of the invention, the component B is present in the fabric softening composition in an amount of 0.05% to 6% by weight.
According to some embodiments of the fabric softening composition of the present invention, the component B is present in the fabric softening composition in an amount of 0.05% to 5% by weight.
According to some embodiments of the fabric softening composition of the present invention, the composition further comprises component C; the component C comprises at least one of nonionic surfactant, thickening agent, spice, preservative, bactericide, pigment, whitening agent, antioxidant and pH regulator.
According to some embodiments of the fabric softening composition 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 invention, the component C is present in the fabric softening composition in an amount of 0.0001% to 20% by weight.
According to some embodiments of the fabric softening composition of the invention, the component C is present in the fabric softening composition in an amount of 0.01% to 10% by weight.
A third aspect of the present invention provides a process for the preparation of a fabric softening composition according to the second aspect of the present invention, comprising the steps of: mixing the components to obtain the fabric softening composition.
According to some embodiments of the method of preparation of the present invention, comprising the steps of: 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 making of the present invention, when the fabric softening composition further comprises component C, the method of making comprises the steps of: and adding the component A and the component B into water, mixing and stirring, then adding the component C, mixing and stirring to obtain the fabric softening composition.
In a fourth aspect the present invention provides the use of a fabric softening composition according to the second aspect of the invention in the softening treatment of fabrics.
According to some embodiments of the use of the present invention, the fabric softening composition is formulated as a fabric softener for fabric softening treatment.
According to some embodiments of the use of the present invention, the fabric softening composition is a liquid fabric softener.
The invention has the beneficial effects that:
1. the hydrolysis inhibitor provided by the invention can effectively inhibit the hydrolysis of the esterquat, thereby improving the long-term storage stability of the fabric softening composition containing the esterquat and having good compatibility of the formula.
2. The fabric softening composition is applied to fabric softening treatment, has good effects of softening, resisting static electricity, sterilizing and the like, and is very wide in the earlier stage of application.
Drawings
FIG. 1 is a graph of a sample with a score of 1 for the condition of fine particulate matter in a high temperature aged sample;
FIG. 2 is a graph of a sample having a score of 5 for fine particles in a high temperature aged sample.
Detailed Description
The embodiment of the invention provides a hydrolysis inhibitor containing ester group quaternary ammonium salt, which is an organic compound with ClogP range of-1.37 < ClogP < 15 and containing a functional group capable of forming hydrogen bond.
The n-octanol/water partition coefficient of an organic compound can reflect the ability of the organic compound to migrate between the aqueous phase and the organism, and is often characterized by a logP value. logP value refers to the logarithm of the ratio of the partition coefficient of a substance in n-octanol (oil) and water. Reflecting the partitioning of the material in both the oil/water phases. The larger the logP value, the more lipophilic the substance is; conversely, the smaller the size, 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: the equilibrium concentration of a substance in n-octanol; cw: the equilibrium concentration of a substance in water.
The logP value can be obtained by experimental methods, and the method mainly comprises a direct method and an indirect method. The direct method comprises a shake flask method, a two-phase titration method and an extraction method; indirect methods include production column methods, chromatography. However, the experimental method is expensive and the test operation is complicated, so that a calculation method is developed. There are two main methods of calculation, one is by the fragment additivity of organic compounds and the other is by the internal relation between other physicochemical parameters of the compounds and their octanol/water partition coefficients. The logP value, namely ClogP, obtained by applying the calculation method can make up for the defects of the experimental method, so that a great amount of professional software such as CLOGP software, proLogP module of Pallas software, clogP/CMR module of SYBYL software and the like (SuChi et al: calculating software of compound lipid-water distribution coefficient and comparative research [ J ] Chinese university of pharmacy, 2008,39 (2): 178-182) are introduced. The ClogP value of the hydrolysis inhibitor of the invention can be calculated using software, such as Chemdraw.
In some embodiments of the invention, the hydrolysis inhibitor has a ClogP range 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.11.4, or-0.02. Ltoreq. ClogP.ltoreq.8.23, or 1.02. 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 a hydrogen bond includes at least one of a hydroxyl group, a carboxyl group, an aldehyde group, an amino group, and an ether bond. That is, 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 present invention, the hydrolysis inhibitor comprises at least one of an alcohol compound and a phenolic compound.
In some examples of the invention, the alcoholic compound includes at least one of 2-methyl-2, 4-pentanediol, anisyl alcohol, benzyl alcohol, phenethyl alcohol, folyl alcohol, 2-hexenol, cinnamyl alcohol, 3-phenylpropanol, dimethyl benzyl carbinol, myrcenol, terpineol, linalool, geraniol, menthol, citronellol, tetrahydrolinalool, alpha-amyl cinnamyl alcohol, and C12-C24 alcohol. C12-C24 alcohol refers to fatty acid with a carbon chain length of 12-24, such as one or more selected from dodecanol, tetradecanol, hexadecanol, octadecanol, eicosanol, docosanol, and tetracosanol.
In some examples of the invention, the phenolic compound comprises at least one of dimethyl hydroquinone, eugenol, isoeugenol, thymol, 3-methyl-4-isopropylphenol, carvacrol.
Some specific examples of the alcohol compound and the phenol compound are given in tables 1 and 2 below, respectively. The hydrolysis inhibitor of the embodiments of the present invention may be selected from one or more organic compounds in tables 1 to 2.
Table 1 examples of alcohol compounds
| Name of raw materials | CAS number | ClogP |
| 2-methyl-2, 4-pentanediol | 107-41-5 | -0.02 |
| Anethol | 123-11-5 | 1.02 |
| Benzyl alcohol | 100-51-6 | 1.10 |
| Phenylethanols | 60-12-8 | 1.33 |
| (Phyllol) | 928-96-1 | 1.40 |
| 2-hexenol | 2305-21-7 | 1.60 |
| Cinnamyl alcohol | 104-55-2 | 1.61 |
| 3-Phenylpropanols | 122-97-4 | 1.71 |
| Dimethyl benzyl carbinols | 100-86-7 | 2.04 |
| Myrcenol | 543-39-5 | 2.61 |
| Terpineol | 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-amylcinnamyl alcohols | 101-85-9 | 4.12 |
| Dodecanol | 112-53-8 | 5.06 |
| Tetradecanol | 112-72-1 | 6.11 |
| Cetyl alcohol | 36653-82-4 | 7.17 |
| Octadecanol | 112-92-5 | 8.23 |
| Eicosanol | 629-96-9 | 9.29 |
| Behenyl alcohol | 661-19-8 | 10.35 |
| Tetracosanol | 506-51-4 | 11.40 |
Table 2 phenolic compounds examples
| Name of raw materials | 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 |
Embodiments of the present invention also provide a fabric softening composition, comprising the following components:
and (2) component A: ester group-containing quaternary ammonium salts;
and (B) component: hydrolysis inhibitors
And water.
The components of the fabric softening compositions of the examples of the 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 ester-containing quaternary ammonium salt has the formula (1):
in the formula (1), R 1 Is selected from C11-C23 substituted or unsubstituted aliphatic hydrocarbon groups, and the substituted group is selected from-OH, phenyl or- (CH) 2 CH 2 O) m ；m＝1～10；
R 2 、R 3 Can be the same OR different and are respectively and independently selected from-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 is selected from-OH or H;
b is an integer from 1 to 5;
when R is 2 、R 3 、R 4 When the hydrogen is 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 not H, c, d and e may be the same or different and are each independently selected from integers of 1 to 3;
x is an anion of valency a, X -a Is selected from Br - 、Cl - 、CH 3 SO 4 - Or CH 3 CH 2 SO 4 - 。
In some embodiments of the invention, the ester-containing quaternary ammonium salt comprises the reaction product of a fatty amine, a fatty acid/grease, and an alkylating agent. For example, fatty amine and fatty acid/oil 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-based quaternary ammonium salt. Depending on the chosen fatty amine, the final reaction product may also comprise one or more of a mixture of mono-, di-, and tri-ester linked compounds. If the fatty amine is triethanolamine, the final reaction product is a mixture of mono-, di-, and tri-ester linked 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 a hydroxyl group. Wherein, the carbon chain length of the fatty acid can be selected from C12-C22. For example, at least one selected from the group consisting of palmitic acid, stearic acid and oleic acid.
In some embodiments of the invention, the alkylating agent comprises at least one of dimethyl sulfate, diethyl sulfate, methyl chloride, and methyl bromide.
In the fabric softening composition of the embodiment of the present invention, the mass percentage of the ester-based quaternary ammonium salt is 0.5% to 25%, preferably 0.1% to 20%, more preferably 1% to 15%, and still more preferably 1% to 10%.
2. Component B
In the fabric softening compositions of the present invention, component B is a hydrolysis inhibitor. The hydrolysis inhibitor described in the embodiments of the present invention is the hydrolysis inhibitor of the previous embodiments.
In the fabric softening composition of the embodiment of the present invention, the mass percentage of the hydrolysis inhibitor is 0.05% to 10%, preferably 0.05% to 6%, more preferably 0.05% to 5%, more preferably 0.1% to 2%, and even more preferably 0.15% to 0.75%.
3. Component C
The fabric softening compositions of embodiments of the present invention may also include other components, component C. Component C may include at least one of a nonionic surfactant, a thickener, a fragrance, a preservative, a bactericide, a pigment, a whitening agent, an antioxidant, an acid-base modifier.
In the fabric softening composition of the embodiment of the invention, the mass percentage of the component C in the fabric softening composition is 0.0001-20%, preferably 0.01-10%.
3.1 nonionic surfactants
In some embodiments of the invention, the nonionic surfactant hydrophobic portion comprises a hydrocarbon chain derived from natural fats and oils and petrochemical materials, and the hydrophilic portion comprises a polyoxyethylene group, a polyol (hydroxyl) group, and further an alcohol amide, an amine oxide, and the like. The hydrophobic raw materials for preparing the nonionic surfactant mainly comprise fatty alcohol (including natural alcohol and synthetic alcohol), alkylphenol, fatty acid, fatty amine, 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 ether (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 ether (EO = 1-70); an alkyl glycoside; amine oxide surfactants.
If a nonionic surfactant is used, the mass percentage 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 be selectively adjusted in viscosity with or without the addition of thickeners as desired for the application. Suitable thickeners include at least one of nonionic and cationic, amphoteric polymers, such as hydrophobically modified cellulose ethers, cationically modified starches, copolymers of methacrylates and acrylamides, amphoteric polymers of acrylates and acrylamidotrimethylammonium chloride, polyacrylamides.
If a thickener is used, the mass percentage of the thickener in the fabric softening composition is generally from 0.01% to 5%, preferably from 0.1% to 5%, more preferably from 0.2% to 1.0%.
3.3 spices
In some embodiments of the invention, the perfume is selected from at least one of: herbal fragrances such as peppermint, spearmint, rosemary, thyme; fruit scents, such as apple, almond, grape, cherry, pineapple, pear, juicy peach, mango, orange, strawberry, blueberry, citrus; floral scents, such as rose-like, lavender-like, carnation-like; and vanilla, gardenia, hawthorn, maidenhair blue, honeysuckle, cyclamen, hyacinth, bracken, clove, jasmine, lily, mimosa, magnolia, orchid, narcissus, orange blossom, licorice, luteolin green, clover, violet, sweet pea, wallflower.
In other embodiments of the present invention, the perfume may also be selected from microcapsule perfumes. A microencapsulated flavour comprises a shell and a core of perfume oil encapsulated within the shell, the perfume oil being released from the microcapsule substantially until the shell is ruptured by mechanical force (e.g. friction). The perfume oil will therefore not evaporate into the surrounding air for a longer period of time. When added to a fabric softening composition, the microencapsulated perfume deposits onto fabrics during the wash or rinse cycle. In this way, the microencapsulated perfume deposited on the fabric releases the perfume when it breaks. The shell of the microcapsule perfume preferably comprises the following materials: aminoplasts, polyacrylates, polyethylenes, polyamides, polystyrenes, polyisoprenes, polycarbonates, polyesters, polyolefins, polysaccharides (e.g., alginates), gelatins, shellacs, epoxy resins, vinyl polymers, silicones, and combinations thereof.
If a perfume is used, the mass percentage of perfume in the fabric softening composition is typically 0.01% to 5%, preferably 0.05% to 2%.
3.4 preservatives
In some embodiments of the invention, the preservative is selected from one or more of cason (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, methylparaben, ethylparaben, propylparaben, isopropylparaben, butylparaben, isobutylparaben, 3-iodo-2-propynyl butylcarbamate, dimethylolhydantoin, and bronopol.
If a preservative is used, the mass percentage of preservative in the fabric softening composition is typically from 0.001% to 1%, preferably from 0.01% to 0.2%.
3.5 Fungicide
In some embodiments of the invention, the biocide is selected from at least one of decyl/dodecyl/tetradecyltrimethylammonium chloride, dioctyl/didecyl/didodecyldimethylammonium chloride, dodecyldimethylbenzylammonium chloride, polyoxyvinyltrimethylammonium chloride, silicone quaternary ammonium salts, 3-methyl-4-isopropylphenol, p-chlorometaxylenol (PCMX), triclosan, 1' -hexamethylene-bis [5- (4-nitrophenyl) ] biguanide hydrochloride, polyhexamethylene biguanide hydrochloride, chlorhexidine acetate, chlorhexidine gluconate, chitosan quaternary ammonium salts, sodium benzoate, potassium sorbate, silver ion biocides.
If a bactericide is used, the mass percentage of the bactericide in the fabric softening composition is generally 0.01% to 3%, preferably 0.1% to 2%.
3.6 coloring matter
In some embodiments of the invention, the pigments 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 mass percentage of pigment in the fabric softening composition is generally between 0.0001% and 0.5%, preferably between 0.001% and 0.1%.
3.7 whitening Agents
In some embodiments of the invention, the brightener is a fluorescent brightener, such as at least one selected from stilbene biphenyl type fluorescent brighteners, triazinylaminostilbene type fluorescent brighteners, bis (1, 2, 3-triazol-2-yl) stilbene type fluorescent brighteners, bis (benzofuran-2-yl) biphenyl, 1, 3-diphenyl-2-pyrazoline, coumarin type fluorescent brighteners; preferably, the optical brightener is a sulfonated product, in the form of its alkali metal salt, including but not limited to stilbene-based compounds such as at least one of 4,4' -bis (2-sodiumsulfonated styryl) biphenyl, bistriazinyl stilbene derivatives.
If a whitening agent is used, the mass percentage of whitening agent in the fabric softening composition is generally between 0.001% and 0.5%, preferably between 0.005% and 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-methylphenol (BHT), butyl Hydroxyanisole (BHA), tocopherol, propyl gallate.
If an antioxidant is used, the mass percentage of antioxidant in the fabric softening composition is generally between 0.01% and 2%, preferably between 0.01% and 1%.
3.9 acid-base regulators
The pH adjusting agent, also called pH adjusting agent, can be used inorganic and/or organic alkalinity sources as well as acidifying agents.
In some embodiments of the present invention, the source of inorganic alkalinity may be selected from one or a combination of sodium hydroxide, potassium hydroxide; the organic alkalinity source can be selected from one or the combination of monoethanolamine and triethanolamine; the inorganic acidifying agent 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 selected from at least one of citric acid, C1 to C30 carboxylic acid.
The pH of the fabric softening compositions of the examples of the invention was adjusted by the addition of an acid base modifier. Preferably, the pH of the fabric softening composition is adjusted to 2 to 5 by the addition of an acid-base adjusting agent; further preferably, the pH of the fabric softening composition is adjusted to 2-4 by adding an acid-base adjusting agent; still further preferably, the pH of the fabric softening composition is adjusted to 2-3 by adding an acid-base adjusting agent; it is further preferred that 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 (W)
The fabric softening composition of the embodiments of the present invention contains water in the balance other than the above components.
The fabric softening compositions of the present invention can be 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 process for preparing the fabric softening composition comprises the steps of: adding the component A and the component B into water, mixing and stirring to prepare the fabric softening composition.
In some embodiments of the invention, the water is heated to 30 ℃ to 85 ℃ before adding component A and component B. In some examples, the water is heated to 65 ℃.
In some embodiments of the invention, component A and component B are added to water and mixed for 1-100 min. In some examples, the mixing time is 20min.
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 fabric softening composition is prepared by a process comprising the steps of: and adding the component A and the component B into water, mixing and stirring, then adding the component C, mixing and stirring, and preparing the fabric softening composition.
In some embodiments of the 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 present invention, the time for adding component C, mixing and stirring is 1min to 100min. In some examples, component C is added with mixing for 10min.
The fabric softening compositions provided by embodiments of the present invention can be made into fabric softeners, such as liquid fabric softeners, and then applied to fabric softening processes.
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 obtained from conventional commercial sources or can be obtained by a method of the prior art, unless otherwise specified. Unless otherwise indicated, the testing or testing methods are conventional in the art.
The test method of the present invention is illustrated below:
1. acid value
The hydrolysis effect of the hydrolysis inhibitor on reducing the esterquat can be characterized by measuring the acid value reduction values of a fresh sample and a high-temperature aged sample. The smaller the decrease in the acid value, the better the hydrolysis inhibition effect.
The acid value test method refers to GB/T9104-2008 & ltIndustrial stearic acid test method & gt, and the test operation is as follows: weighing 3g of sample, dissolving with 30mL of isopropanol, adding 3-4 drops of phenolphthalein indicator, immediately titrating with 0.1mol/L potassium hydroxide standard solution to light pink, and keeping the solution for 15s to be fadeless.
The acid value is calculated by the formula:
in formula (3):
c, concentration of the potassium hydroxide standard solution, mol/L;
v-volume of standard solution of potassium hydroxide consumed, mL;
56.1-molar mass of potassium hydroxide, g/mol;
m represents the mass of the sample, g.
The acid value reduction (mgKOH/g) is calculated as = acid value of high temperature aged sample-acid value of fresh sample.
The high temperature aging conditions tested by the invention were 85 ℃ aging for 120h.
2. Fine particulate matter in high temperature aged samples
If the esterquat is hydrolyzed, fine particles can be observed in a sample, and the more obvious the hydrolysis degree is, the more fine particles are. The degree of hydrolysis was scored semi-quantitatively by visually observing the amount of fine particulate matter.
The score is divided into 1-5 points, and the higher the score is, the more fine particles are indicated. Wherein, a score of 1 indicates that substantially no fine particulate matter is observed; a score of 5 indicates that a significant amount of fine particulate matter can be observed.
The scoring operation method comprises the following steps:
aging the sample at 85 ℃ for 120h, cooling to room temperature, and referring to the operating method marked with QB/T4535-2013 fabric softener dispersion: about 0.5g of sample was weighed into a 300mL beaker, 200mL of hard water (250 ppm) was added and stirred for 1min at 400r/min using a standard four blade propeller and observed in a well lit environment.
In the following examples or comparative examples, esterquat was used under the commercial designation REWOQUAT WE 28SH, and the major component was ethyl dipalmitate hydroxyethyl methyl ammonium methyl sulfate. The pH value of the water solution of the ester quaternary ammonium salt is about 3. AQUAGEL C45 is used as thickener.
Unless otherwise specified, the samples of the examples of the present invention and the comparative examples were prepared according to the formulation compositions in the following tables, by mixing and stirring the respective components with water and adjusting the pH =2.5 to 2.7 of the composition with an appropriate amount of citric acid with reference to the preparation methods of the previous examples.
Table 3 shows the formulation compositions and test results for comparative example 1 and examples 1-6.
TABLE 3 formulation compositions and test results for comparative example 1 and examples 1-6
As can be seen from comparative example 1 and examples 1-2 in Table 3, the addition of octadecanol or a mixed C16/18 alcohol reduced the acid value even less, allowing the acid value of the sample to be reduced from 3.41mgKOH/g to about 2.6mgKOH/g. From examples 3 to 5, it is understood that when 0.15% to 0.6% of menthol is added, the acid value decreases to a smaller extent as the amount of menthol added increases. Example 6 is a carbon-mixed C16/18 alcohol and menthol are compounded, and the two further generate synergistic effect, so that the acid value reduction value is further reduced.
FIGS. 1 and 2 show graphs of samples with a score of 1 and 5 for fine particles in the high-temperature aged samples, respectively. It can be seen from fig. 1 that substantially no fine particles are observed in the sample, whereas it can be seen from fig. 2 that there are a large number of fine particles in the sample. It can also be seen from the results of scoring the fine particulate matter condition in the high temperature aged samples in table 3 that comparative example 1 has more pronounced hydrolyzed fine particulate matter, as shown in fig. 2; examples 1-6 were essentially free of observed fine particulates, as shown in fig. 1.
Therefore, based on the test results of comparative example 1, the present inventors judged that the test data having a lower reduction in acid value than the corresponding comparative example had the effect of inhibiting the hydrolysis of the ester quat.
Table 4 shows the formulation compositions and test results for comparative examples 2 to 5 and examples 7 to 10, and Table 5 shows the formulation compositions and test results for examples 11 to 14.
TABLE 4 formulation compositions and test results for comparative examples 2 to 5 and examples 7 to 10
TABLE 5 formulation compositions and test results for examples 11-14
From tables 4-5, the effect of hydrolysis inhibitors of different ClogP values on reducing the rate of hydrolysis of ester quats can be compared:
comparative example 4 and comparative example 5, in which glycerin having a ClogP value of-1.54 and ethylene glycol having a ClogP value of-1.37 were added, respectively, it can be seen from Table 4 that these two samples had substantially no hydrolysis-inhibiting effect and the acid value was reduced to be substantially equivalent to that of comparative example 1. Example 7 is a solution containing 2-methyl-2, 4-pentanediol having a ClogP value of-0.02, and has a certain hydrolysis-inhibiting effect. From examples 8 to 10, it is seen that the effect of the hydrolysis inhibitor tends to increase as the ClogP increases when the amount of the hydrolysis inhibitor added is the same.
Comparative example 2 added ethyl heptanoate having a ClogP of 3.36 and comparative example 3 added isobutyl phenylacetate having a ClogP of 3.28, both had ClogP values comparable to thymol and carvacrol, but had no hydrolysis-inhibiting effect, and therefore it was considered necessary to contain a functional group capable of forming a hydrogen bond in the hydrolysis inhibitor.
It can also be seen from the results of scoring the fine particulate matter in the high temperature aged samples that comparative examples 2-5 had more pronounced hydrolyzed fine particulate matter, example 7 had very little fine particulate matter, and examples 8-16 had substantially no fine particulate matter observed.
Table 6 shows the formulation compositions and test results for comparative example 6 and examples 15-16.
TABLE 6 formulation compositions and test results for comparative example 6 and examples 15-16
As can be seen from comparative example 6 and examples 15 to 16 of Table 6, the samples without the thickener AQUAGEL C45 were also inhibited from hydrolysis by the addition of menthol or thymol.
The test results show that the hydrolysis of the ester-containing quaternary ammonium salt can be effectively inhibited by adding the hydrolysis inhibitor which has the technical characteristics that ClogP is more than-1.37 and less than 15 and contains the functional group capable of forming hydrogen bonds, the formula compatibility is good, and the long-term storage stability of the product can be improved.
The fabric softening treatment test was carried out on samples of the examples and comparative examples as follows:
the fabric material is as follows: white towel of knitted pure cotton, size 24 × 24cm, each towel weighing about 30g.
Pretreatment: the towel for the softness performance test needs to be pretreated to remove the softening finishing agent before delivery. The pretreatment method comprises the steps of putting the knitted towel into a standard washing machine, washing for 3 times by using 20 wt% of lauryl alcohol ether sodium sulfate (sodium hydroxide is used for adjusting the pH stock solution to be about 8.5) as a basic detergent according to the standard washing procedure of the washing machine, rinsing in a rinsing-dewatering mode, repeatedly rinsing until no foam exists, taking out after spin-drying, and hanging and drying at room temperature.
Sample treatment: the drum washing machine has the following specific washing procedures:
1.2kg of fabric (10 knitted pure cotton white towels, the weight is complemented by pure cotton cloth, 30g of standard laundry detergent, 40g of softener and the mixing procedure is carried out; and after washing, taking out the towel and naturally drying.
Evaluation of softness: selecting 10 trained evaluators for hand feeling evaluation. The softness score was scored from 0 to 5, and 10 panelists evaluated the scores 1 time, 10 times respectively, and the scores were averaged, with higher scores indicating better softness performance, and the test results are shown in table 7.
TABLE 7 evaluation results of softness 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 clear that the samples of example 5 and comparative example 1 both have good softening effect and are well suited for softening treatment of fabrics.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such modifications are intended to be included in the scope of the present invention.
Claims (10)
1. A hydrolysis inhibitor containing an ester-based quaternary ammonium salt, characterized in that,
the hydrolysis inhibitor is an organic compound having a ClogP in the range-1.37 < ClogP < 15 and containing a functional group capable of forming a hydrogen bond.
2. The hydrolysis inhibitor of claim 1, wherein said hydrolysis inhibitor has a ClogP range of: -0.05. Ltoreq. ClogP. Ltoreq.12.
3. The hydrolysis inhibitor according to claim 1, wherein the functional group capable of forming a hydrogen bond comprises at least one of a hydroxyl group, a carboxyl group, an aldehyde group, an amino group, and an ether bond.
4. The hydrolysis inhibitor according to any one of claims 1 to 3, wherein the hydrolysis inhibitor comprises at least one of an alcohol compound and a phenolic compound.
5. The hydrolysis inhibitor of claim 4, wherein said hydrolysis inhibitor comprises at least one of 2-methyl-2, 4-pentanediol, anisyl alcohol, benzyl alcohol, phenethyl alcohol, folyl alcohol, 2-hexenol, cinnamyl alcohol, 3-phenylpropanol, dimethylbenzyl alcohol, myrcenol, terpineol, linalool, geraniol, menthol, citronellol, tetrahydrolinalool, alpha-amylcinnamyl alcohol, C12-C24 alcohols, dimethyl hydroquinone, eugenol, isoeugenol, thymol or isomers thereof, and carvacrol.
6. A fabric softening composition comprising the following components:
and (2) component A: ester group-containing quaternary ammonium salts;
and (B) component: the hydrolysis inhibitor of any one of claims 1 to 5;
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%.
7. The fabric softening composition of claim 6, wherein the esterquat has the formula (1):
in the formula (1), R 1 Is selected from C11-C23 substituted or unsubstituted aliphatic hydrocarbon groups, and the substituted group is selected from-OH, phenyl or- (CH) 2 CH 2 O) m ；m＝1～10；
R 2 、R 3 Can be the same OR different and are respectively and independently selected from-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 is selected from-OH or H;
b is an integer from 1 to 5;
when R is 2 、R 3 、R 4 When the hydrogen is 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 not H, c, d and e may be the same or different and are each independently selected from integers of 1 to 3;
x is an anion of valency a, X -a Is selected from Br - 、Cl-、CH 3 SO 4 - Or CH 3 CH 2 SO 4 - 。
8. A fabric softening composition according to claim 6 or 7, further comprising component C; the component C comprises at least one of nonionic surfactant, thickening agent, spice, preservative, bactericide, pigment, whitening agent, antioxidant and pH regulator.
9. A process for preparing a fabric softening composition as claimed in any of claims 6 to 8, comprising the steps of:
mixing the components to obtain the fabric softening composition.
10. Use of a fabric softening composition as claimed in any one of claims 6 to 8 in fabric softening treatment.
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| US4840738A (en) * | 1988-02-25 | 1989-06-20 | The Procter & Gamble Company | Stable biodegradable fabric softening compositions containing 2-hydroxypropyl monoester quaternized ammonium salts |
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| 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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| 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 |
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