JP2019094581A - Transparent liquid softener composition - Google Patents
Transparent liquid softener composition Download PDFInfo
- Publication number
- JP2019094581A JP2019094581A JP2017222637A JP2017222637A JP2019094581A JP 2019094581 A JP2019094581 A JP 2019094581A JP 2017222637 A JP2017222637 A JP 2017222637A JP 2017222637 A JP2017222637 A JP 2017222637A JP 2019094581 A JP2019094581 A JP 2019094581A
- Authority
- JP
- Japan
- Prior art keywords
- mass
- component
- less
- acid
- transparent liquid
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 111
- 239000007788 liquid Substances 0.000 title claims abstract description 91
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 51
- 239000000194 fatty acid Substances 0.000 claims abstract description 51
- 229930195729 fatty acid Natural products 0.000 claims abstract description 51
- -1 fatty acid ester Chemical class 0.000 claims abstract description 45
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 43
- 125000002252 acyl group Chemical group 0.000 claims abstract description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims abstract description 10
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims abstract description 10
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims abstract description 9
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims abstract description 9
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000005642 Oleic acid Substances 0.000 claims abstract description 9
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims abstract description 8
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims abstract description 8
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims abstract description 8
- 229960004488 linolenic acid Drugs 0.000 claims abstract description 8
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000002736 nonionic surfactant Substances 0.000 claims abstract description 7
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000006353 oxyethylene group Chemical group 0.000 claims description 11
- 239000004902 Softening Agent Substances 0.000 claims description 10
- 150000001450 anions Chemical class 0.000 claims description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 8
- 235000021313 oleic acid Nutrition 0.000 claims description 8
- 239000002304 perfume Substances 0.000 claims description 8
- 235000020778 linoleic acid Nutrition 0.000 claims description 7
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 238000003860 storage Methods 0.000 abstract description 32
- 230000007774 longterm Effects 0.000 abstract description 8
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract description 8
- 229960004232 linoleic acid Drugs 0.000 abstract 1
- 229960002969 oleic acid Drugs 0.000 abstract 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 33
- 238000000034 method Methods 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 238000006460 hydrolysis reaction Methods 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 230000007062 hydrolysis Effects 0.000 description 12
- 238000005886 esterification reaction Methods 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 10
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 239000000796 flavoring agent Substances 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 8
- 235000019634 flavors Nutrition 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 238000005956 quaternization reaction Methods 0.000 description 7
- 230000010933 acylation Effects 0.000 description 6
- 238000005917 acylation reaction Methods 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 125000005907 alkyl ester group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 125000004185 ester group Chemical group 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000003205 fragrance Substances 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 229940050176 methyl chloride Drugs 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 230000001133 acceleration Effects 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 239000002168 alkylating agent Substances 0.000 description 4
- 229940100198 alkylating agent Drugs 0.000 description 4
- 239000002518 antifoaming agent Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 150000007522 mineralic acids Chemical class 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 235000021314 Palmitic acid Nutrition 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000008051 alkyl sulfates Chemical class 0.000 description 3
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000002738 chelating agent Substances 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 3
- 229940008406 diethyl sulfate Drugs 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- 238000013268 sustained release Methods 0.000 description 3
- 239000012730 sustained-release form Substances 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 2
- OALYTRUKMRCXNH-UHFFFAOYSA-N 5-pentyloxolan-2-one Chemical compound CCCCCC1CCC(=O)O1 OALYTRUKMRCXNH-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- JYXGIOKAKDAARW-UHFFFAOYSA-N N-(2-hydroxyethyl)iminodiacetic acid Chemical compound OCCN(CC(O)=O)CC(O)=O JYXGIOKAKDAARW-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- 229940077388 benzenesulfonate Drugs 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- JOZKFWLRHCDGJA-UHFFFAOYSA-N citronellol acetate Chemical compound CC(=O)OCCC(C)CCC=C(C)C JOZKFWLRHCDGJA-UHFFFAOYSA-N 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical compound COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000012086 standard solution Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 2
- PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 description 2
- SFEOKXHPFMOVRM-UHFFFAOYSA-N (+)-(S)-gamma-ionone Natural products CC(=O)C=CC1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-UHFFFAOYSA-N 0.000 description 1
- GDIYABNICDPBCR-UHFFFAOYSA-N (1-tert-butylcyclohexyl) acetate Chemical compound CC(=O)OC1(C(C)(C)C)CCCCC1 GDIYABNICDPBCR-UHFFFAOYSA-N 0.000 description 1
- VKZRWSNIWNFCIQ-WDSKDSINSA-N (2s)-2-[2-[[(1s)-1,2-dicarboxyethyl]amino]ethylamino]butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NCCN[C@H](C(O)=O)CC(O)=O VKZRWSNIWNFCIQ-WDSKDSINSA-N 0.000 description 1
- JIRHAGAOHOYLNO-UHFFFAOYSA-N (3-cyclopentyloxy-4-methoxyphenyl)methanol Chemical compound COC1=CC=C(CO)C=C1OC1CCCC1 JIRHAGAOHOYLNO-UHFFFAOYSA-N 0.000 description 1
- YPZUZOLGGMJZJO-XRGAULLZSA-N (3as,5as,9as,9br)-3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1h-benzo[e][1]benzofuran Chemical compound CC([C@@H]1CC2)(C)CCC[C@]1(C)[C@@H]1[C@@]2(C)OCC1 YPZUZOLGGMJZJO-XRGAULLZSA-N 0.000 description 1
- JRJBVWJSTHECJK-LUAWRHEFSA-N (z)-3-methyl-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one Chemical compound CC(=O)C(\C)=C/C1C(C)=CCCC1(C)C JRJBVWJSTHECJK-LUAWRHEFSA-N 0.000 description 1
- 239000001709 1,2-dimethylcyclohex-3-ene-1-carbaldehyde Substances 0.000 description 1
- GUMOJENFFHZAFP-UHFFFAOYSA-N 2-Ethoxynaphthalene Chemical compound C1=CC=CC2=CC(OCC)=CC=C21 GUMOJENFFHZAFP-UHFFFAOYSA-N 0.000 description 1
- FLUWAIIVLCVEKF-UHFFFAOYSA-N 2-Methyl-1-phenyl-2-propanyl acetate Chemical compound CC(=O)OC(C)(C)CC1=CC=CC=C1 FLUWAIIVLCVEKF-UHFFFAOYSA-N 0.000 description 1
- CIEZZGWIJBXOTE-UHFFFAOYSA-N 2-[bis(carboxymethyl)amino]propanoic acid Chemical compound OC(=O)C(C)N(CC(O)=O)CC(O)=O CIEZZGWIJBXOTE-UHFFFAOYSA-N 0.000 description 1
- XSAYZAUNJMRRIR-UHFFFAOYSA-N 2-acetylnaphthalene Chemical compound C1=CC=CC2=CC(C(=O)C)=CC=C21 XSAYZAUNJMRRIR-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- VPXWZHXOBQZDNM-UHFFFAOYSA-N 4,4-dimethylcyclohex-2-ene-1-carbaldehyde Chemical compound CC1(CCC(C=O)C=C1)C VPXWZHXOBQZDNM-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- JOZKFWLRHCDGJA-LLVKDONJSA-N Citronellyl acetate Natural products CC(=O)OCC[C@H](C)CCC=C(C)C JOZKFWLRHCDGJA-LLVKDONJSA-N 0.000 description 1
- XRHCAGNSDHCHFJ-UHFFFAOYSA-N Ethylene brassylate Chemical compound O=C1CCCCCCCCCCCC(=O)OCCO1 XRHCAGNSDHCHFJ-UHFFFAOYSA-N 0.000 description 1
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- 239000005792 Geraniol Substances 0.000 description 1
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- PDIZYYQQWUOPPK-UHFFFAOYSA-N acetic acid;2-(methylamino)acetic acid Chemical compound CC(O)=O.CC(O)=O.CNCC(O)=O PDIZYYQQWUOPPK-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- GUUHFMWKWLOQMM-NTCAYCPXSA-N alpha-hexylcinnamaldehyde Chemical compound CCCCCC\C(C=O)=C/C1=CC=CC=C1 GUUHFMWKWLOQMM-NTCAYCPXSA-N 0.000 description 1
- GUUHFMWKWLOQMM-UHFFFAOYSA-N alpha-n-hexylcinnamic aldehyde Natural products CCCCCCC(C=O)=CC1=CC=CC=C1 GUUHFMWKWLOQMM-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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Landscapes
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Description
本発明は、外観上透明な液体柔軟剤組成物に関する。 The present invention relates to an appearance transparent liquid softener composition.
現在の柔軟剤に用いられる基材として、環境中に排出されても速やかに分解し、環境への負荷を低減することを目的に分子内エステル基を有する陽イオン性界面活性剤が主たる柔軟基剤として使用されている。エステル基が水中で加水分解し易いことは周知であり、液体柔軟剤組成物中でエステル基を有する柔軟基剤が加水分解すると、貯蔵安定性の品質が悪化し易いことも周知である。 As a base material used for the present softening agent, a cationic surfactant having an intramolecular ester group is a main softening group for the purpose of decomposing quickly even if discharged into the environment and reducing the load on the environment. It is used as an agent. It is well known that ester groups are susceptible to hydrolysis in water, and it is also well known that the storage stability quality tends to deteriorate when the soft base having ester groups is hydrolyzed in the liquid softener composition.
近年、審美的観点から透明な柔軟剤の開発が行われている。特許文献１には４級アンモニウム化合物に特定の有機酸を配合することで透明化させる技術が開示されており、また特許文献２にはエステル基を持つ４級アンモニウム化合物又は３級アミン化合物に特定の非イオン性界面活性剤と脂肪酸又はその塩を配合する透明柔軟剤が開示されている。また特許文献３〜７にはアルケニル基比率が多い等の特徴を有する特定の４級アンモニウム化合物とポリオキシエチレンモノフェニルエーテル系溶剤を含有する透明柔軟剤が開示されている。 In recent years, transparent softeners have been developed from an aesthetic point of view. Patent Document 1 discloses a technique for clarifying a quaternary ammonium compound by blending a specific organic acid, and Patent Document 2 specifies a quaternary ammonium compound having an ester group or a tertiary amine compound. A transparent softener is disclosed which combines a nonionic surfactant and a fatty acid or a salt thereof. Further, Patent Documents 3 to 7 disclose a transparent softener containing a specific quaternary ammonium compound and a polyoxyethylene monophenyl ether solvent having characteristics such as a large proportion of alkenyl groups.
特許文献１、２の柔軟組成物では分子内にエステル基を有する柔軟基剤の加水分解による長期貯蔵時の透明な外観の担保が十分ではない。 The flexible compositions of Patent Documents 1 and 2 do not sufficiently ensure the transparent appearance during long-term storage by hydrolysis of the flexible base having an ester group in the molecule.
本発明は長期貯蔵による安定性に優れ、更には広い温度領域における保存安定性に優れた透明液体柔軟剤組成物を提供する。 The present invention provides a transparent liquid softener composition excellent in long-term storage stability and further excellent in storage stability in a wide temperature range.
なお、本発明でいう透明液体柔軟剤組成物とは、測定セルの光路長５０ｍｍの石英セルを使用し、標準液として蒸留水を用いた場合に５０．０ｍｇ/Ｌ以下の濁度である液体柔軟剤組成物をいう。
また、本明細書において、透明液体柔軟剤組成物を単に液体柔軟剤組成物という場合もある。
In addition, the transparent liquid softening agent composition in the present invention is a liquid having a turbidity of 50.0 mg / L or less when using a quartz cell having an optical path length of 50 mm of the measurement cell and using distilled water as a standard solution. Softener composition.
Also, in the present specification, the transparent liquid softener composition may be simply referred to as a liquid softener composition.
本発明は、下記（Ａ）成分を１質量％以上２０質量％以下、下記（Ｂ）成分を５質量％以上２０質量％以下、下記（Ｃ）成分を０．５質量％以上１．５質量％以下、下記（Ｄ）成分を１質量％以上１０質量％以下、及び水を含有し、３０℃におけるｐＨが２．０以上５．０以下である、透明液体柔軟剤組成物に関する。
＜（Ａ）成分＞
下記一般式（Ａ１）で表される４級アンモニウム塩化合物であって、アシル基を脂肪酸と見做した場合に、オレイン酸、リノール酸及びリノレン酸の割合が、アシル基を構成している全脂肪酸の６０質量％以上１００質量％以下である４級アンモニウム塩化合物
In the present invention, the following component (A) is 1% by mass to 20% by mass, the following component (B) is 5% by mass to 20% by mass, and the following component (C) is 0.5% by mass to 1.5% The present invention relates to a transparent liquid softener composition containing 1% by mass or more and 10% by mass or less of the following component (D) and water and having a pH of 2.0 or more and 5.0 or less at 30 ° C.
<(A) component>
It is a quaternary ammonium salt compound represented by the following general formula (A1), and when the acyl group is regarded as a fatty acid, all the proportions of oleic acid, linoleic acid and linolenic acid make up the acyl group Quaternary ammonium salt compound that is 60 mass% or more and 100 mass% or less of fatty acid
〔式中、Ｒ１ａ、Ｒ２ａはそれぞれ独立して、炭素数１６以上２２以下の脂肪酸からＯＨを除いた残基（アシル基という）、又は水素原子であり、ただし、Ｒ１ａ、Ｒ２ａの少なくとも１つは、アシル基であり、Ｒ３ａは炭素数１以上３以下のアルキル基又は−Ｃ２Ｈ４−ＯＲ４ａであり、Ｒ４ａは炭素数１６以上２２以下のアシル基又は水素原子であり、Ｒ５ａは炭素数１以上３以下のアルキル基であり、Ｘ−は陰イオンである。〕
＜（Ｂ）成分＞
下記一般式（Ｂ１）で表される溶剤
[Wherein, R 1a and R 2a each independently represent a residue obtained by removing OH from a fatty acid having 16 to 22 carbon atoms (referred to as an acyl group), or a hydrogen atom, provided that R 1a and R 2a At least one is an acyl group, R 3a is an alkyl group having 1 to 3 carbon atoms or -C 2 H 4 -OR 4a , and R 4a is an acyl group having 16 to 22 carbon atoms or a hydrogen atom R 5a is an alkyl group having 1 or more and 3 or less carbon atoms, and X − is an anion. ]
<(B) component>
Solvent represented by the following general formula (B1)
〔式中、ｎは、オキシエチレン基の平均付加モル数であり、１以上１５以下の数である。〕
＜（Ｃ）成分＞
下記一般式（Ｃ１）で表される４級アンモニウム塩化合物
[In the formula, n is the average added mole number of the oxyethylene group, and is a number of 1 or more and 15 or less. ]
<(C) component>
Quaternary ammonium salt compound represented by the following general formula (C1)
〔式中、Ｒ１ｃは炭素数１２以上１８以下の炭化水素基であり、Ｒ２ｃ、Ｒ３ｃ、Ｒ４ｃは、それぞれ独立に、炭素数１以上３以下のアルキル基である。Ｙ−は陰イオンである。〕
＜（Ｄ）成分＞
下記一般式（Ｄ１）で表される非イオン性界面活性剤
Ｒ１ｄ−Ｏ−（Ｃ２Ｈ４Ｏ）ｐ−Ｈ （Ｄ１）
〔式中、Ｒ１ｄは炭素数１０以上１８以下の炭化水素基であり、また、pはオキシエチレン基の平均付加モル数であり、３以上１０以下の数である。〕
[Wherein, R 1c is a hydrocarbon group having 12 to 18 carbon atoms, and R 2c , R 3c , and R 4c are each independently an alkyl group having 1 to 3 carbon atoms. Y - is an anion. ]
<(D) component>
Nonionic surfactant represented by the following general formula (D1)
R 1d -O- (C 2 H 4 O) p -H (D1)
[Wherein, R 1d is a hydrocarbon group having 10 to 18 carbon atoms, and p is the average addition mole number of the oxyethylene group, and is a number of 3 to 10]. ]
本発明によれば、長期貯蔵による安定性に優れ、更には広い温度領域における保存安定性に優れた透明液体柔軟剤組成物を提供することができる。 According to the present invention, it is possible to provide a transparent liquid softener composition which is excellent in long-term storage stability and further excellent in storage stability in a wide temperature range.
［透明液体柔軟剤組成物］
＜（Ａ）成分＞
本発明の（Ａ）成分は、下記一般式（Ａ１）で表される４級アンモニウム塩化合物であって、アシル基を脂肪酸と見做した場合に、オレイン酸、リノール酸及びリノレン酸の割合が、アシル基を構成している全脂肪酸の６０質量％以上１００質量％以下である４級アンモニウム塩化合物である。
[Transparent liquid softener composition]
<(A) component>
The component (A) of the present invention is a quaternary ammonium salt compound represented by the following general formula (A1), and when the acyl group is regarded as a fatty acid, the ratio of oleic acid, linoleic acid and linolenic acid is And a quaternary ammonium salt compound that is 60% by mass or more and 100% by mass or less of the total fatty acid constituting the acyl group.
〔式中、Ｒ１ａ、Ｒ２ａはそれぞれ独立して、炭素数１６以上２２以下の脂肪酸からＯＨを除いた残基（アシル基という）、又は水素原子であり、ただし、Ｒ１ａ、Ｒ２ａの少なくとも１つは、アシル基であり、Ｒ３ａは炭素数１以上３以下のアルキル基又は−Ｃ２Ｈ４−ＯＲ４ａであり、Ｒ４ａは炭素数１６以上２２以下のアシル基又は水素原子であり、Ｒ５ａは炭素数１以上３以下のアルキル基であり、Ｘ−は陰イオンである。〕 [Wherein, R 1a and R 2a each independently represent a residue obtained by removing OH from a fatty acid having 16 to 22 carbon atoms (referred to as an acyl group), or a hydrogen atom, provided that R 1a and R 2a At least one is an acyl group, R 3a is an alkyl group having 1 to 3 carbon atoms or -C 2 H 4 -OR 4a , and R 4a is an acyl group having 16 to 22 carbon atoms or a hydrogen atom R 5a is an alkyl group having 1 or more and 3 or less carbon atoms, and X − is an anion. ]
本発明の（Ａ）成分は、アシル基を構成している全脂肪酸中、オレイン酸、リノール酸、及びリノレン酸から選ばれる１種以上の割合が、６０質量％以上、好ましくは７０質量％以上、より好ましくは７５質量％以上、更に好ましくは８０質量％以上、より更に好ましくは８５質量％以上、そして、１００質量％以下、好ましくは９８質量％以下、より好ましくは９５質量％以下である。
（Ａ）成分は、この脂肪酸の割合の条件を満たした上で、アシル基を構成している全脂肪酸中、オレイン酸の割合が、好ましくは５０質量％以上、より好ましくは６０質量％以上、更より好ましくは６５質量％以上であり、そして、好ましくは１００質量％以下、より好ましくは９５質量％以下、更に好ましくは９０質量％以下である。
In the component (A) of the present invention, the proportion of one or more selected from oleic acid, linoleic acid and linolenic acid is 60% by mass or more, preferably 70% by mass or more, based on all the fatty acids constituting the acyl group. More preferably, it is 75 mass% or more, more preferably 80 mass% or more, still more preferably 85 mass% or more, and 100 mass% or less, preferably 98 mass% or less, more preferably 95 mass% or less.
The proportion of oleic acid in the total fatty acid constituting the acyl group is preferably 50% by mass or more, more preferably 60% by mass or more, while satisfying the condition of the proportion of this fatty acid in the component (A). Still more preferably, it is 65% by mass or more, and preferably 100% by mass or less, more preferably 95% by mass or less, still more preferably 90% by mass or less.
（Ａ）成分のアシル基を構成する、オレイン酸、リノール酸及びリノレン酸以外の脂肪酸としては、ステアリン酸、パルミチン酸及びエライジン酸を挙げることができる。 Examples of fatty acids other than oleic acid, linoleic acid and linolenic acid that constitute the acyl group of component (A) include stearic acid, palmitic acid and elaidic acid.
（Ａ）成分はトリエタノールアミン脂肪酸エステル、またはＮ-アルキル（炭素数１以上３以下）ジエタノールアミン脂肪酸エステルの４級化物であることから、アシル化度が１、２又は３の３つの異なる４級化合物から構成されるものである。（Ａ）成分の平均アシル化率は、柔軟性、組成物の保存安定性及び残香持続性の観点から、好ましくは１．３以上、より好ましくは１．５以上、そして、好ましくは２．０以下、より好ましくは１．９５以下である。平均アシル化度は、脂肪酸とトリエタノールアミン、またはＮ-アルキル（炭素数１以上３以下）ジエタノールアミンとの反応比率及び４級化の際のアルキル化剤との反応比率や反応条件によって調整することができる。 The component (A) is a triethanolamine fatty acid ester, or a quaternary of N-alkyl (1 to 3 carbon atoms) diethanolamine fatty acid ester, so that the three different quaternary with an acylation degree of 1, 2 or 3 It is composed of a compound. The average acylation ratio of the component (A) is preferably 1.3 or more, more preferably 1.5 or more, and preferably 2.0 from the viewpoint of flexibility, storage stability of the composition and persistence of residual aroma. Or less, more preferably 1.95 or less. The average degree of acylation should be adjusted according to the reaction ratio of fatty acid with triethanolamine or N-alkyl (1 to 3 carbon atoms) diethanolamine, the reaction ratio with alkylating agent in quaternization, and the reaction conditions Can.
本発明では（Ａ）成分を構成するそれぞれの割合は以下の比率が好ましい。アシル化度が１の化合物、すなわち一般式（Ａ１）中のＲ１ａがアシル基であり、Ｒ２ａが水素原子であり、Ｒ３ａが−Ｃ２Ｈ４−ＯＲ４ａである場合のＲ４ａが水素原子である化合物（ａ１）〔以下、（ａ１）成分という〕の割合が、一般式（Ａ１）で表される４級アンモニウム塩の全量中、５質量％以上、好ましくは１０質量％以上、より好ましくは１５質量％以上、そして、４５質量％以下、好ましくは４０質量％以下、より好ましくは３５質量％以下であって、
アシル化度が２の化合物、すなわち一般式（Ａ１）中のＲ１ａ及びＲ２ａがアシル基であり、Ｒ３ａが−Ｃ２Ｈ４−ＯＲ４ａである場合のＲ４ａが水素原子である化合物（ａ２）〔以下、（ａ２）成分という〕の割合が、一般式（Ａ１）で表される４級アンモニウム塩の全量中、３０質量％以上、より好ましくは３５質量％以上、好ましくは４０質量％以上、そして、７５質量％以下、好ましくは７０質量％以下、より好ましくは６５質量％以下であって、
アシル化度が３の化合物、すなわち一般式（Ａ１）中のＲ１ａ及びＲ２ａがアシル基であり、Ｒ３ａが−Ｃ２Ｈ４−ＯＲ４ａであり、Ｒ４ａがアシル基である化合物（ａ３）〔以下、（ａ３）成分という〕の割合が、一般式（Ａ１）で表される４級アンモニウム塩の全量中、５質量％以上、好ましくは８質量％以上、より好ましくは１０質量％以上、そして、４０質量％以下、好ましくは３０質量％以下、より好ましくは２５質量％以下である。
In the present invention, the respective proportions constituting the component (A) are preferably the following proportions. R 4a is a compound having an acylation degree of 1, that is, R 1a in the general formula (A1) is an acyl group, R 2a is a hydrogen atom, and R 3a is —C 2 H 4 —OR 4a The proportion of the compound (a1) [hereinafter referred to as component (a1)], which is a hydrogen atom, is 5% by mass or more, preferably 10% by mass or more, based on the total amount of the quaternary ammonium salt represented by General Formula (A1). More preferably, it is 15% by mass or more and 45% by mass or less, preferably 40% by mass or less, more preferably 35% by mass or less.
Compounds having an acylation degree of 2, that is, compounds where R 1a and R 2a in the general formula (A1) are an acyl group, and R 4a is a hydrogen atom when R 3a is —C 2 H 4 —OR 4a The proportion of (a2) [hereinafter referred to as component (a2)] is 30% by mass or more, more preferably 35% by mass or more, preferably 40% by mass, based on the total amount of the quaternary ammonium salt represented by the general formula (A1) % Or more and 75% by mass or less, preferably 70% by mass or less, more preferably 65% by mass or less,
Compounds having an acylation degree of 3, that is, compounds in which R 1a and R 2a in the general formula (A1) are an acyl group, R 3a is —C 2 H 4 —OR 4a and R 4a is an acyl group ( The proportion of a3) [hereinafter referred to as component (a3)] is 5% by mass or more, preferably 8% by mass or more, more preferably 10% by mass, based on the total amount of the quaternary ammonium salt represented by the general formula (A1) The content is 40% by mass or less, preferably 30% by mass or less, and more preferably 25% by mass or less.
（ａ２）成分と（ａ３）成分は柔軟効果及び香料前駆体の繊維製品への吸着に有効な成分であるが、透明液体柔軟剤組成物の保存安定性に影響を与える。そのために、（Ａ）成分は、（ａ１）成分を適度に残した組成であることが好ましい。更には、前記の割合を満たした上で、（Ａ）成分中の（ａ２）成分の含有量が（ａ３）成分よりも多いこと、より好ましくは（ａ２）成分の含有量（質量％）と（ａ３）成分の含有量（質量％）との差が、１５質量％以上、好ましくは２０質量％以上、より好ましくは２５質量％以上あることである。 The components (a2) and (a3) are components effective for the softening effect and the adsorption of the perfume precursor onto the textile, but they affect the storage stability of the transparent liquid softener composition. Therefore, it is preferable that (A) component is the composition which left the (a1) component moderately. Furthermore, after satisfying the above ratio, the content of the component (a2) in the component (A) is larger than that of the component (a3), more preferably the content (% by mass) of the component (a2) The difference with the content (mass%) of the component (a3) is 15 mass% or more, preferably 20 mass% or more, more preferably 25 mass% or more.
一般式（Ａ１）中、Ｒ５ａはメチル基又はエチル基が好ましい。
一般式（Ａ１）中、Ｘ−は、ハロゲンイオン、好ましくはクロロイオン、炭素数１以上３以下のアルキル硫酸エステルイオン、炭素数１以上３以下のアルキル基が１個以上３個以下置換していてもよいベンゼンスルホン酸イオンから選ばれる陰イオンが好ましく、炭素数１以上３以下のアルキル硫酸エステルイオンがより好ましく、メチル硫酸エステルイオン又はエチル硫酸エステルイオンがより好ましい。
In general formula (A1), R 5a is preferably a methyl group or an ethyl group.
In the general formula (A1), X - represents a halogen ion, preferably a chloro ion, an alkyl sulfate ester ion having 1 to 3 carbon atoms, or an alkyl group having 1 to 3 carbon atoms, substituted by 1 to 3 An anion selected from benzenesulfonate ions which may be selected is preferable, an alkyl sulfate ion having 1 to 3 carbon atoms is more preferable, and a methyl sulfate ion or an ethyl sulfate ion is more preferable.
本発明に用いる（Ａ）成分は、オレイン酸、リノール酸及びリノレン酸の比率が規定濃度の脂肪酸とトリエタノールアミン、又はＮ-アルキル（炭素数１以上３以下）ジエタノールアミンを脱水エステル化反応させる方法（脱水エステル化法という）、又は前記脂肪酸による脂肪酸低級アルキルエステル（低級アルキルはメチル基、エチル基、プロピル基）とトリエタノールアミン、又はＮ-アルキル（炭素数１以上３以下）ジエタノールアミンをエステル交換反応させる方法（エステル交換法という）により得られたエステル化反応物を、アルキル化剤で４級化反応させることで得ることができる。本発明の（Ａ）成分の（ａ１）成分〜（ａ３）成分の割合を満たす混合物を得るには、例えば、脂肪酸又は脂肪酸低級アルキルエステル：トリエタノールアミン又はＮ-アルキル（炭素数１以上３以下）ジエタノールアミンのモル比を、好ましくは１．３：１以上、より好ましくは１．５：１以上、そして、好ましくは２．０：１以下、より好ましくは１．９５：１以下の比率で反応させたトリエタノールアミン脂肪酸エステル、またはＮ−アルキル（炭素数１以上３以下）ジエタノールアミン脂肪酸エステルの混合物を４級化反応させる。 Component (A) used in the present invention is a method of dehydration esterification reaction of fatty acid with triethanolamine or N-alkyl (1 to 3 carbon atoms) diethanolamine in which the ratio of oleic acid, linoleic acid and linolenic acid is the specified concentration (Referred to as dehydration esterification method), or fatty acid lower alkyl ester (lower alkyl is methyl group, ethyl group, propyl group) with said fatty acid and triethanolamine, or N-alkyl (C1 or more and 3 or less) diethanolamine is transesterified The esterification reaction product obtained by the reaction method (referred to as transesterification method) can be obtained by quaternization reaction with an alkylating agent. In order to obtain a mixture satisfying the ratio of the components (a1) to (a3) of the component (A) of the present invention, for example, a fatty acid or a fatty acid lower alkyl ester: triethanolamine or N-alkyl (having 1 to 3 carbon atoms) ) The molar ratio of diethanolamine is preferably 1.3: 1 or more, more preferably 1.5: 1 or more, and preferably 2.0: 1 or less, more preferably 1.95: 1 or less. A mixture of triethanolamine fatty acid ester, or N-alkyl (having 1 or more and 3 or less carbon atoms) diethanolamine fatty acid ester is subjected to quaternization reaction.
なお、選択水素化反応を行った場合には、（Ａ）成分の例えば脂肪酸部分が、不飽和結合の幾何異性体となり、混合物を形成するが、本発明ではシス／トランスが、好ましくは２５／７５〜１００／０、より好ましくは５０／５０〜９５／５（モル比）が好適である。 When the selective hydrogenation reaction is performed, for example, the fatty acid moiety of the component (A) becomes a geometric isomer of unsaturated bond to form a mixture, but in the present invention, cis / trans is preferably 25 / 75 to 100/0, more preferably 50/50 to 95/5 (molar ratio) is suitable.
脱水エステル化法においては、エステル化反応温度を１４０℃以上２３０℃以下で縮合水を除去しながら反応させることが好ましい。反応を促進させる目的から通常のエステル化触媒を用いても差し支えなく、例えば硫酸、燐酸などの無機酸、酸化錫、酸化亜鉛などの無機酸化物、テトラプロポキシチタンなどのアルコラートなどを選択することができる。反応の進行はＪＩＳ Ｋ ００７０−１９９２に記載の方法で酸価（ＡＶ）及び鹸化価（ＳＶ）を測定することで確認を行い、好適にはＡＶが１０ｍｇＫＯＨ／ｇ以下、好ましくは６ｍｇＫＯＨ／ｇ以下となった時、エステル化反応を終了する。得られるエステル化合物の混合物は、ＳＶが好ましくは１１０ｍｇＫＯＨ／ｇ以上、より好ましくは１３０ｍｇＫＯＨ／ｇ以上であり、そして、好ましくは２１０ｍｇＫＯＨ／ｇ以下、より好ましくは１９０ｍｇＫＯＨ／ｇ以下である。 In the dehydration esterification method, it is preferable to carry out the reaction while removing condensation water at an esterification reaction temperature of 140 ° C. or more and 230 ° C. or less. A conventional esterification catalyst may be used for the purpose of promoting the reaction, for example, inorganic acids such as sulfuric acid and phosphoric acid, inorganic oxides such as tin oxide and zinc oxide, alcoholates such as tetrapropoxy titanium, etc. it can. The progress of the reaction is confirmed by measuring the acid value (AV) and the saponification value (SV) according to the method described in JIS K 0070-1992, and preferably AV is 10 mg KOH / g or less, preferably 6 mg KOH / g or less When it becomes, the esterification reaction is finished. The resulting ester compound mixture preferably has an SV of 110 mg KOH / g or more, more preferably 130 mg KOH / g or more, and preferably 210 mg KOH / g or less, more preferably 190 mg KOH / g or less.
エステル交換法において、反応は、好ましくは５０℃以上、より好ましくは１００℃以上、そして、好ましくは１５０℃以下の温度で、生成する低級アルコールを除去しながら行う。反応促進のために水酸化ナトリウム、水酸化カリウムなどの無機アルカリや、メチラート、エチラートなどのアルコキシ触媒を用いることも可能である。反応の進行はガスクロマトグラフィーなどを用いて脂肪酸低級アルキルエステルの量を直接定量することが好適であり、未反応脂肪酸低級アルキルエステルが仕込みの脂肪酸低級アルキルエステルに対してガスクロマトグラフィーチャート上で１０面積％以下、特に６面積％以下で反応を終了させることが好ましい。得られるエステル化合物の混合物は、ＳＶが好ましくは１１０ｍｇＫＯＨ／ｇ以上、より好ましくは１３０ｍｇＫＯＨ／ｇ以上、そして、好ましくは２１０ｍｇＫＯＨ／ｇ以下、より好ましくは１９０ｍｇＫＯＨ／ｇ以下である。 In the transesterification method, the reaction is carried out at a temperature of preferably 50 ° C. or more, more preferably 100 ° C. or more, and preferably 150 ° C. or less, while removing the lower alcohol formed. In order to accelerate the reaction, it is also possible to use an inorganic alkali such as sodium hydroxide or potassium hydroxide, or an alkoxy catalyst such as methylate or ethylate. It is preferable to directly determine the amount of fatty acid lower alkyl ester using gas chromatography etc. The progress of the reaction is preferably 10 on the gas chromatography chart with respect to fatty acid lower alkyl ester charged with unreacted fatty acid lower alkyl ester. It is preferable to terminate the reaction at an area% or less, particularly at 6 area% or less. The mixture of ester compounds obtained preferably has an SV of 110 mg KOH / g or more, more preferably 130 mg KOH / g or more, and preferably 210 mg KOH / g or less, more preferably 190 mg KOH / g or less.
次にこのようにして得られたエステル化合物の４級化を行うが、４級化に用いられるアルキル化剤としては、メチルクロリド、ジメチル硫酸、ジエチル硫酸等が好適である。アルキル化剤として、メチルクロリドを用いる場合には、特に溶媒を使用する必要はないが、溶媒を使用する場合は、エタノールやイソプロパノールなどの溶媒を、エステル化合物に対して１０質量％以上５０質量％以下程度混合した溶液をチタン製のオートクレーブなどの加圧反応器に仕込み、密封下３０℃以上１２０℃以下の反応温度でメチルクロリドを圧入させて反応させる。このときメチルクロリドの一部が分解し塩酸が発生する場合があるため、アルカリ剤を少量加えることで反応が効率よく進むため好適である。メチルクロリドとエステル化合物とのモル比は、エステル化合物のアミノ基１当量に対してメチルクロリドを１倍当量以上１．５倍当量以下用いることが好適である。 Next, quaternization of the ester compound thus obtained is performed, and as an alkylating agent used for quaternization, methyl chloride, dimethyl sulfate, diethyl sulfate and the like are preferable. When methyl chloride is used as the alkylating agent, it is not necessary to use a solvent, but when using a solvent, a solvent such as ethanol or isopropanol is used in an amount of 10% by mass to 50% by mass based on the ester compound. The mixed solution is charged into a pressure reactor such as an autoclave made of titanium, and methyl chloride is injected at a reaction temperature of 30 ° C. or more and 120 ° C. or less under sealed condition to cause a reaction. At this time, since a part of methyl chloride may be decomposed to generate hydrochloric acid, addition of a small amount of an alkali agent is preferable because the reaction proceeds efficiently. As for the molar ratio of methyl chloride to the ester compound, it is preferable to use methyl chloride at 1 to 1.5 equivalents equivalent to 1 equivalent of the amino group of the ester compound.
ジメチル硫酸及び／又はジエチル硫酸とエステル化合物とのモル比は、エステル化合物のアミノ基１当量に対してジメチル硫酸及び／又はジエチル硫酸を好ましくは０．９倍当量以上、より好ましくは０．９５倍当量以上、そして、好ましくは１．１倍当量以下、より好ましくは０．９９倍当量以下用いる。 The molar ratio of dimethyl sulfate and / or diethyl sulfate to the ester compound is preferably 0.9 times or more, more preferably 0.95 equivalents or more of dimethyl sulfate and / or diethyl sulfate per equivalent of the amino group of the ester compound. An equivalent or more, and preferably 1.1 or less equivalent, more preferably 0.99 or less equivalent is used.
本発明の透明液体柔軟剤組成物は、（Ａ）成分の製造時に生成されるその他反応生成物を含有してもよい。例えば、４級化されなかった未反応アミンとして、具体的には脂肪酸トリエステル構造体のアミンと脂肪酸ジエステル構造体のアミンがあり、製法によっては、脂肪酸トリエステル構造体のアミンと脂肪酸ジエステル構造体のアミンとを合計して、（Ａ）成分１００質量部に対して５〜３０質量部含む反応生成物が得られる。一方、脂肪酸モノエステル構造体のアミンは４級化し易いことから、通常、反応生成物中の含有量は（Ａ）成分１００質量部に対して０．５質量部以下である。更には脂肪酸エステル化されなかったトリエタノールアミン及びトリエタノールアミンの４級化物、又はＮ-アルキル（炭素数１以上３以下）ジエタノールアミン及びＮ-アルキル（炭素数１以上３以下）ジエタノールアミンの４級化物は合計で（Ａ）成分１００質量部に対して０．５〜３質量部含有され、このうち９０質量％以上は４級化物である。また未反応脂肪酸が含まれることもある。（Ａ）成分を含む反応生成物を用いる場合は、本発明の効果を損なわない限り、このような未反応成分や副反応成分が液体柔軟剤組成物中に含まれていてもよい。 The transparent liquid softener composition of the present invention may contain other reaction products produced during the production of the component (A). For example, as the non-quaternized unreacted amine, specifically, there are an amine of fatty acid triester structure and an amine of fatty acid diester structure, and depending on the manufacturing method, an amine of fatty acid triester structure and fatty acid diester structure The reaction product containing 5 to 30 parts by mass with respect to 100 parts by mass of the component (A) is obtained. On the other hand, since the amine of the fatty acid monoester structure is easily quaternized, the content in the reaction product is usually 0.5 parts by mass or less with respect to 100 parts by mass of the component (A). Furthermore, quaternary esters of triethanolamine and triethanolamine which are not esterified with fatty acid, or quaternary of N-alkyl (1 to 3 carbon atoms) diethanolamine and N-alkyl (1 to 3 carbon atoms) diethanolamine Is contained in an amount of 0.5 to 3 parts by mass with respect to 100 parts by mass of the component (A). Of these, 90% by mass or more is a quaternary compound. It may also contain unreacted fatty acids. When a reaction product containing the component (A) is used, such unreacted components and side reaction components may be contained in the liquid softener composition as long as the effects of the present invention are not impaired.
（Ａ）成分として（ａ１）成分、（ａ２）成分及び（ａ３）成分を含む混合物を用いる場合、該混合物中の（ａ１）成分、（ａ２）成分、（ａ３）成分、アミン化合物の割合等は、高速液体クロマトグラフ（ＨＰＬＣと言う場合もある）を用い、検出器として荷電荷粒子検出器（ＣｈａｒｇｅｄＡｅｒｏｓｏｌ Ｄｅｔｅｃｔｉｏｎ、ＣＡＤと言う場合もある）を使用して求めることができる。ＣＡＤを用いた測定方法については「荷電化粒子検出器Ｃｏｒｏｎａ ＣＡＤの技術と応用」(福島ら Chromatography, Vol.32 No.3(2011))を参考にすることができる。 When a mixture containing the components (a1), (a2) and (a3) is used as the component (A), the proportions of the component (a1), the component (a2), the component (a3) and the amine compound in the mixture Can be determined using a high performance liquid chromatograph (sometimes referred to as HPLC) and a charged particle detector (sometimes referred to as Charged Aerosol Detection, sometimes referred to as CAD) as a detector. For the measurement method using CAD, "Technology and Application of Charged Particle Detector Corona CAD" (Fukushima et al., Chromatography, Vol. 32 No. 3 (2011)) can be referred to.
本発明の透明液体柔軟剤組成物は、（Ａ）成分を、柔軟性、透明な外観、および高温、低温での保存安定性の観点から、１質量％以上、好ましくは５質量％以上、そして、２０質量％以下、好ましくは１５質量％以下含有する。 The transparent liquid softener composition of the present invention contains 1% by mass or more, preferably 5% by mass or more, from the viewpoint of flexibility, a transparent appearance, and storage stability at high temperatures and low temperatures. 20% by mass or less, preferably 15% by mass or less.
＜（Ｂ）成分＞
本発明における（Ｂ）成分は、下記一般式（Ｂ１）で表される溶剤である。
<(B) component>
The component (B) in the present invention is a solvent represented by the following general formula (B1).
〔式中、ｎは、オキシエチレン基の平均付加モル数であり、１以上１５以下の数である。〕 [In the formula, n is the average added mole number of the oxyethylene group, and is a number of 1 or more and 15 or less. ]
一般式（Ｂ１）中、ｎは、液外観を透明に保つ観点から、１以上、好ましくは１．５以上、そして、１５以下、好ましくは１０以下、より好ましくは５以下である。 In the general formula (B1), n is 1 or more, preferably 1.5 or more, and 15 or less, preferably 10 or less, more preferably 5 or less, from the viewpoint of keeping the liquid appearance transparent.
本発明の透明液体柔軟剤組成物は、（Ｂ）成分を、透明な外観、および高温、低温での保存安定性の観点から、５質量％以上、好ましくは１０質量％以上、そして、２０質量％以下、好ましくは１５質量％以下含有する。 The transparent liquid softener composition of the present invention has 5% by mass or more, preferably 10% by mass or more, and 20% by mass from the viewpoint of transparent appearance and storage stability at high temperature and low temperature of the component (B). % Or less, preferably 15% by mass or less.
＜（Ｃ）成分＞
本発明における（Ｃ）成分は、下記一般式（Ｃ１）で表される４級アンモニウム塩化合物である。
<(C) component>
The component (C) in the present invention is a quaternary ammonium salt compound represented by the following general formula (C1).
〔式中、Ｒ１ｃは炭素数１２以上、そして、１８以下、好ましくは１４以下の炭化水素基、好ましくはアルキル基又はアルケニル基であり、Ｒ２ｃ、Ｒ３ｃ、Ｒ４ｃは、それぞれ独立に、炭素数１以上３以下のアルキル基、好ましくはエチル基又はメチル基である。Ｙ−は陰イオンである。〕 [Wherein, R 1c is a hydrocarbon group having a carbon number of 12 or more and 18 or less, preferably 14 or less, preferably an alkyl group or an alkenyl group, and R 2c , R 3c and R 4c are each independently It is an alkyl group having 1 to 3 carbon atoms, preferably an ethyl group or a methyl group. Y - is an anion. ]
一般式（Ｃ１）中、Ｙ−は、ハロゲンイオン、好ましくはクロロイオン、炭素数１以上３以下のアルキル硫酸エステルイオン、炭素数１以上３以下のアルキル基が１個以上３個以下置換していてもよいベンゼンスルホン酸イオンから選ばれる陰イオンが好ましく、炭素数１以上３以下のアルキル硫酸エステルイオンがより好ましく、メチル硫酸エステルイオン又はエチル硫酸エステルイオンがより好ましい。 In the general formula (C1), Y - is a halogen ion, have preferably substituted chloro ion, 1 to 3 carbon atoms an alkyl sulfate ion, the following three 1 or more alkyl groups of 1 to 3 carbon atoms An anion selected from benzenesulfonate ions which may be selected is preferable, an alkyl sulfate ion having 1 to 3 carbon atoms is more preferable, and a methyl sulfate ion or an ethyl sulfate ion is more preferable.
本発明の透明液体柔軟剤組成物は、（Ｃ）成分を、透明な外観、および高温、低温での保存安定性の観点から、０．５質量％以上、そして、１．５質量％以下、好ましくは１．０質量％以下含有する。 The transparent liquid softener composition of the present invention contains 0.5% by mass or more and 1.5% by mass or less of the component (C) from the viewpoint of transparent appearance and storage stability at high temperature and low temperature. Preferably, the content is 1.0% by mass or less.
本発明の透明液体柔軟剤組成物は、（Ａ）成分の含有量と（Ｃ）成分の含有量との質量比（Ａ）／（Ｃ）が、長期保存時の低温での保存安定性を担保する観点から、好ましくは５以上、より好ましくは７以上、更に好ましくは１０以上、そして、好ましくは２０以下、より好ましくは１８以下、更に好ましくは１６以下である。 In the transparent liquid softener composition of the present invention, the mass ratio (A) / (C) of the content of the component (A) to the content of the component (C) is the storage stability at low temperature during long-term storage From the viewpoint of securing, it is preferably 5 or more, more preferably 7 or more, further preferably 10 or more, and preferably 20 or less, more preferably 18 or less, further preferably 16 or less.
＜（Ｄ）成分＞
本発明における（Ｄ）成分は、下記一般式（Ｄ１）で表される非イオン性界面活性剤である。
Ｒ１ｄ−Ｏ−（Ｃ２Ｈ４Ｏ）ｐ−Ｈ （Ｄ１）
〔式中、Ｒ１ｄは炭素数１０以上、そして、１８以下、好ましくは１４以下の炭化水素基、好ましくはアルキル基又はアルケニル基であり、また、pはオキシエチレン基の平均付加モル数であり、３以上、好ましくは５以上、そして、１０以下の数である。〕
<(D) component>
The component (D) in the present invention is a nonionic surfactant represented by the following general formula (D1).
R 1d -O- (C 2 H 4 O) p -H (D1)
[Wherein, R 1d is a hydrocarbon group having a carbon number of 10 or more and 18 or less, preferably 14 or less, preferably an alkyl group or an alkenyl group, and p is the average addition mole number of oxyethylene group , 3 or more, preferably 5 or more and 10 or less. ]
本発明の透明液体柔軟剤組成物は、（Ｄ）成分を、透明な外観、および高温、低温での保存安定性の観点から、１質量％以上、好ましくは４質量％以上、そして、１０質量％以下、好ましくは７質量％以下含有する。 The transparent liquid softener composition of the present invention contains 1% by mass or more, preferably 4% by mass or more, and 10% by mass from the viewpoint of transparent appearance and storage stability at high temperature and low temperature. % Or less, preferably 7% by mass or less.
本発明の透明液体柔軟剤組成物は水を含有する。水は、脱イオン水、脱イオン水に次亜塩素酸塩を少量配合した滅菌した水、水道水等を用いることができる。
本発明の透明液体柔軟剤組成物は、水を、好ましくは５０質量％以上、より好ましくは６０質量％以上、更に好ましくは７０質量％以上、より更に好ましくは８０質量％以上、そして、好ましくは９９質量％以下、より好ましくは９５質量％以下含有する。
The transparent liquid softener composition of the present invention contains water. As water, deionized water, sterilized water prepared by blending a small amount of hypochlorite in deionized water, tap water, etc. can be used.
The transparent liquid softener composition of the present invention preferably contains water at 50% by mass or more, more preferably 60% by mass or more, still more preferably 70% by mass or more, still more preferably 80% by mass or more, and preferably The content is 99% by mass or less, more preferably 95% by mass or less.
＜透明液体柔軟剤組成物の３０℃におけるｐＨ＞
本発明の透明液体柔軟剤組成物の３０℃におけるｐＨは、２．０以上５．０以下であり、液体柔軟剤組成物による処理後の繊維製品の発香性及び残香性の観点、及び保存安定性の観点から、好ましくは２．５以上、より好ましくは２．７以上、更に好ましくは２．９以上、そして、好ましくは４．８以下、より好ましくは４．５以下、更に好ましくは４．２以下、より更に好ましくは４．０以下、より更に好ましくは３．５以下である。
<PH of transparent liquid softener composition at 30 ° C.>
The pH at 30 ° C. of the transparent liquid softener composition of the present invention is 2.0 or more and 5.0 or less, and the odor and residual odor of fiber products after treatment with the liquid softener composition, and preservation From the viewpoint of stability, preferably 2.5 or more, more preferably 2.7 or more, further preferably 2.9 or more, and preferably 4.8 or less, more preferably 4.5 or less, more preferably 4 .2 or less, more preferably 4.0 or less, still more preferably 3.5 or less.
ｐＨは、「ＪＩＳ Ｋ ３３６２；２００８の項目８．３に従って３０℃において測定する。ｐＨは、アルカリ剤や後述する酸剤等のｐＨ調整剤により調整することができる。 The pH is measured at 30 ° C. in accordance with “JIS K 3362; 2008, item 8.3. The pH can be adjusted with a pH adjuster such as an alkali agent or an acid agent described later.
＜透明液体柔軟剤組成物の３０℃における粘度＞
本発明の透明液体柔軟剤組成物の３０℃における粘度は、使用勝手の点で、好ましくは５ｍＰａ・ｓ以上、より好ましくは８ｍＰａ・ｓ以上、更に好ましくは１０ｍＰａ・ｓ以上、そして、好ましくは１５０ｍＰａ・ｓ以下、より好ましくは１３０ｍＰａ・ｓ以下、更に好ましくは１１０ｍＰａ・ｓ以下である。液体柔軟剤組成物の粘度は、Ｂ型粘度計を用いて、Ｎｏ．１〜Ｎｏ．３ローターのいずれかのローターを用い、６０ｒ／ｍｉｎで、測定開始から１分後の指示値である。液体柔軟剤組成物は３０±１℃に調温して測定する。粘度計の測定領域が２つのローターで得られた場合であって、換算した粘度が異なる場合は、ローター番号の小さい方のデータを採用する。
<Viscosity at 30 ° C. of transparent liquid softener composition>
The viscosity at 30 ° C. of the transparent liquid softener composition of the present invention is preferably 5 mPa · s or more, more preferably 8 mPa · s or more, still more preferably 10 mPa · s or more, and preferably 150 mPa · s from the viewpoint of usability. S or less, more preferably 130 mPa · s or less, still more preferably 110 mPa · s or less. The viscosity of the liquid softener composition was measured using a B-type viscometer. 1 to No. It is an indicated value one minute after the start of measurement at 60 r / min using any of three rotors. The liquid softener composition is measured at a temperature of 30 ± 1 ° C. When the measurement area of the viscometer is obtained by two rotors and the converted viscosity is different, the smaller data of the rotor number is adopted.
本発明の透明液体柔軟剤組成物は、更に以下に示す成分を含有することが好ましい。
＜（Ｅ）成分＞
本発明の透明液体柔軟剤組成物は、（Ｅ）成分として、下記一般式（Ｅ１）で表される非イオン性界面活性剤を含有してもよい。
Ｒ１ｅ−Ｏ−（Ｃ２Ｈ４Ｏ）ｑ−Ｈ （Ｅ１）
〔式中、Ｒ１ｅは炭素数１０以上、そして、１８以下、好ましくは１４以下の炭化水素基、好ましくはアルキル基又はアルケニル基であり、また、ｑはオキシエチレン基の平均付加モル数であり、１０を超え、好ましくは１５以上、より好ましくは２０以上、そして、６０以下、好ましくは５０以下、より好ましくは４０以下の数である。〕
The transparent liquid softener composition of the present invention preferably further contains the components shown below.
<(E) component>
The transparent liquid softener composition of the present invention may contain, as the component (E), a nonionic surfactant represented by the following general formula (E1).
R 1e -O- (C 2 H 4 O) q -H (E 1)
[Wherein, R 1e is a hydrocarbon group having a carbon number of 10 or more and 18 or less, preferably 14 or less, preferably an alkyl group or an alkenyl group, and q is the average addition mole number of oxyethylene group , 10 or more, preferably 15 or more, more preferably 20 or more, and 60 or less, preferably 50 or less, more preferably 40 or less. ]
本発明の透明液体柔軟剤組成物は、（Ｅ）成分を、透明な外観、および高温、低温での保存安定性の観点から、１質量％以上、そして、５質量％以下、好ましくは３質量％以下含有する。 The transparent liquid softener composition of the present invention contains the component (E) in an amount of 1% by mass or more and 5% by mass or less, preferably 3% by mass from the viewpoint of transparent appearance and storage stability at high temperature and low temperature. It contains less than%.
本発明の透明液体柔軟剤組成物は、（Ｄ）成分の含有量と（Ｅ）成分の含有量との質量比（Ｄ）／（Ｅ）が、長期保存時の低温での保存安定性を担保する観点から、好ましくは１．２以上、より好ましくは２．５以上、そして、好ましくは６．０以下、より好ましくは４．０以下である。 In the transparent liquid softener composition of the present invention, the mass ratio (D) / (E) of the content of the component (D) to the content of the component (E) is the storage stability at low temperature during long-term storage From the viewpoint of securing, it is preferably 1.2 or more, more preferably 2.5 or more, and preferably 6.0 or less, more preferably 4.0 or less.
＜（Ｆ）成分：香料化合物＞
本発明の透明液体柔軟剤組成物は、（Ｆ）成分として、香料化合物を含有してもよい。
（Ｆ）成分の香料化合物とは、後述の（Ｋ）成分の徐放性香料に用いられる香料化合物以外の香料化合物を意味する。
<(F) component: perfume compound>
The transparent liquid softener composition of the present invention may contain, as the component (F), a flavor compound.
The perfume compound of the component (F) means a perfume compound other than the perfume compound used for the sustained release perfume of the component (K) described later.
（Ｆ）成分として用いることができる香料化合物に特に制限はない。
（Ｆ）成分として用いることができる香料化合物としては、例えば「香料と調香の基礎知識、中島基貴 編著、産業図書株式会社発行、２００５年４月２０日 第４刷」に記載の香料化合物や特許文献等を通じて柔軟剤に配合することが知られている香料化合物の他に、香料メーカーが独自に調製した香料成分又は調香した香料組成物を使用することができる。
例えば、β−イオノン（３．７）、γ−ウンデカラクトン（３．８）、γ−ノナラクトン（２．８）、γ−メチルイオノン（４．０）、アンブロキサン（５．３）、イソＥスーパー（４．７）、エチルバニリン（１．８）、エチレンブラッシレート（４．６）、オイゲノール（３．０）、カシュメラン（ＩＦＦ社製）（４．０）、クマリン（１．５）、ゲラニオール（２．４）、酢酸ｏ，ｔ−ブチルシクロヘキシル（４．１）、酢酸シトロネリル（４．２）、酢酸ジメチルベンジルカルビニル（２．８）、サンダルマイソールコア（３．９）、ジヒドロジャスモン酸メチル（２．４）、ジヒドロミルセノール（３．０）、ジメチルテトラヒドロベンズアルデヒド（２．９）、ジャバノール（ジボダン製）（４．７）、ネロリンヤラヤラ（３．２）、ハバノライド（フィルメニッヒ製）（６．２）、フルーテート（花王株式会社）（３．４）、ペオニル（ジボダン製）（４．０）、ヘキシルシンナミックアルデヒド（４．９）、ヘリオトロピン（１．１）、メチルβ−ナフチルケトン（２．８）、メチルアンスラニレート（２．０）、ラズベリーケトン（１．１）、リモネン（４．４）、及びリリアール（３．９）を挙げることができる。なお（ ）内の数値はｌｏｇＰ値である。
There is no restriction in particular in the spice compound which can be used as (F) ingredient.
Examples of the flavor compounds which can be used as the component (F) include the flavor compounds described in “Basic knowledge of flavor and fragrance, edited by Nakajima Motohiro, published by Sangyo Tosho Co., Ltd., April 20, 2005, 4th edition”. In addition to the flavor compounds known to be incorporated into softeners through patent documents and the like, it is possible to use a flavor component or a flavor composition flavored by a flavor manufacturer.
For example, β-ionone (3.7), γ-undecalactone (3.8), γ-nonalactone (2.8), γ-methylionone (4.0), ambroxane (5.3), iso E Super (4.7), ethyl vanillin (1.8), ethylene brassylate (4.6), eugenol (3.0), kashmelan (IFF company) (4.0), coumarin (1.5), Geraniol (2.4), o, t-butylcyclohexyl acetate (4.1), citronellyl acetate (4.2), dimethylbenzylcarbinyl acetate (2.8), sandal mysore core (3.9), dihydrojasmon Acid methyl (2.4), dihydromyrcenol (3.0), dimethyltetrahydrobenzaldehyde (2.9), jabanol (from divodane) (4.7), neroline yalayara (3.2) Habanolide (product of Filmenich) (6.2), fruitate (Kao Co., Ltd.) (3.4), peonil (made of divodane) (4.0), hexyl cinnamic aldehyde (4.9), heliotropin (1. 1), methyl β-naphthyl ketone (2.8), methyl anthranilate (2.0), raspberry ketone (1.1), limonene (4.4), and lilliard (3.9) can be mentioned . The numerical values in parentheses are log P values.
なお、本発明の透明液体柔軟剤組成物は、香料化合物の希釈剤や保留剤を含有してもよい。希釈剤及び保留剤としては、ジプロピレングリコール、パルミチン酸イソプロピルエステル、ジエチルフタレート、ペンジルベンゾエート、流動パラフィン、イソパラフィン、及び油脂等を挙げることができる。
希釈剤及び保留剤を用いる場合、（Ｆ）成分と希釈剤及び保留剤との合計に対する希釈剤及び保留剤の量は、好ましくは０質量％以上２０質量％以下である。
In addition, the transparent liquid softening agent composition of this invention may contain the diluent and retention agent of a fragrance | flavor compound. Diluents and retention agents include dipropylene glycol, isopropyl palmitate, diethyl phthalate, penzyl benzoate, liquid paraffin, isoparaffins, oils and fats and the like.
When a diluent and a retention agent are used, the amount of the diluent and the retention agent based on the total of the component (F) and the diluent and the retention agent is preferably 0% by mass or more and 20% by mass or less.
本発明の透明液体柔軟剤組成物が（Ｆ）成分を含有する場合、その含有量は、好ましくは１．０質量％以上、そして、好ましくは２．０質量％以下である。なお、液体柔軟剤組成物中の（Ｆ）成分は、製品に合わせてその含有量を調整することができる。 When the transparent liquid softener composition of the present invention contains the component (F), its content is preferably 1.0% by mass or more, and preferably 2.0% by mass or less. In addition, (F) component in a liquid softening agent composition can be adjusted according to a product.
＜（Ｇ）成分：水溶性有機溶剤＞
本発明の透明液体柔軟剤組成物は、低温での保存安定性を更に高める観点から（Ｇ）成分として、（Ｂ）成分以外の水溶性有機溶剤を含有することができる。水溶性有機溶剤としては、液体柔軟剤組成物に用いられる一般的な水溶性有機溶剤が挙げられる。なお、（Ｇ）成分における「水溶性有機溶剤」とは、２０℃の脱イオン水１００ｇに対して２０ｇ以上溶解する有機溶剤をいう。水溶性有機溶剤の具体例としては、プロピレングリコール、エチレングリコール、グリセリン、ジエチレングリコール、イソプロパノール、及びエタノールから選ばれる１種以上を挙げることができる。これらの中でも、エチレングリコール及びグリセリンから選ばれる１種以上が好ましい。
<(G) component: water soluble organic solvent>
The transparent liquid softener composition of the present invention may contain a water-soluble organic solvent other than the component (B) as the component (G) from the viewpoint of further enhancing the storage stability at low temperatures. Examples of the water-soluble organic solvent include common water-soluble organic solvents used in liquid softener compositions. In addition, the "water-soluble organic solvent" in (G) component means an organic solvent which melt | dissolves 20 g or more with respect to 100 g of 20 degreeC deionized water. Specific examples of the water-soluble organic solvent may include one or more selected from propylene glycol, ethylene glycol, glycerin, diethylene glycol, isopropanol, and ethanol. Among these, one or more selected from ethylene glycol and glycerin are preferable.
本発明の透明液体柔軟剤組成物が（Ｇ）成分を含有する場合、その含有量は、低温での保存安定性の観点から、好ましくは２．０質量％以上、より好ましくは４．０質量％以上、そして、好ましくは１０質量％以下、より好ましくは７．０質量％以下である。 When the transparent liquid softener composition of the present invention contains the component (G), the content is preferably 2.0% by mass or more, more preferably 4.0% from the viewpoint of storage stability at low temperature % Or more, and preferably 10% by mass or less, more preferably 7.0% by mass or less.
本発明の液体柔軟剤組成物は、低温での保存安定性を更に高める観点から、（Ｇ）成分として、エチレングリコール（以下、（Ｇ１）成分という）及びグリセリン（以下、（Ｇ２）成分という）から選ばれる１種以上を含有することが好ましく、（Ｇ１）成分と（Ｇ２）成分の両方を含有することがより好ましい。
本発明の液体柔軟剤組成物において、（Ｇ１）成分と（Ｇ２）成分の両方を含有する場合、（Ｇ１）成分の含有量と（Ｇ２）成分の含有量との質量比（Ｇ１）／（Ｇ２）は、低温での保存安定性を担保する観点から、好ましくは０．３以上、より好ましくは１．０以上、そして、好ましくは４．０以下、より好ましくは２．０以下である。
The liquid softener composition of the present invention has ethylene glycol (hereinafter referred to as (G1) component) and glycerin (hereinafter referred to as (G2) component) as the (G) component from the viewpoint of further enhancing the storage stability at low temperatures. It is preferable to contain 1 or more types chosen from, and it is more preferable to contain both (G1) component and (G2) component.
When the liquid softener composition of the present invention contains both the (G1) component and the (G2) component, the mass ratio of the content of the (G1) component to the content of the (G2) component (G1) / ( G2) is preferably 0.3 or more, more preferably 1.0 or more, and preferably 4.0 or less, more preferably 2.0 or less from the viewpoint of securing storage stability at low temperature.
＜（Ｉ）成分：酸剤＞
本発明の透明液体柔軟剤組成物は、液体柔軟剤組成物のｐＨを調整する観点から、（Ｉ）成分として酸剤を含有することができる。
酸剤としては、無機酸及び有機酸が挙げられ、無機酸の具体例としては、塩酸、及び硫酸が挙げられる。有機酸の具体例としては、炭素数１以上１０以下の１価又は多価のカルボン酸、又は炭素数１以上２０以下の１価又は多価のスルホン酸、炭素数１以上３以下のアルキル硫酸が挙げられる。より具体的には、メチル硫酸、エチル硫酸、ｐ−トルエンスルホン酸、（ｏ−、ｍ−、ｐ−）キシレンスルホン酸、ベンゼンスルホン酸、ドデシルベンゼンスルホン酸、グリコール酸、エチレンジアミン４酢酸、クエン酸、安息香酸、及びサリチル酸が挙げられる。
これらの中でも、無機酸であれば塩酸が好ましく、有機酸であれば炭素数１以上１０以下の１価又は多価のカルボン酸が好ましく、クエン酸がより好ましい。
本発明の透明液体柔軟剤組成物が酸剤を含有する場合、その含有量は、（Ａ）成分の種類や量によって適宜調整することができ、ｐＨが前記範囲になる範囲であって、保存安定性を損なわない程度が好ましい。
<(I) component: acid agent>
The transparent liquid softener composition of the present invention can contain an acid agent as the component (I) from the viewpoint of adjusting the pH of the liquid softener composition.
As an acid agent, an inorganic acid and an organic acid are mentioned, As a specific example of an inorganic acid, hydrochloric acid and a sulfuric acid are mentioned. Specific examples of the organic acid include a monovalent or polyvalent carboxylic acid having 1 to 10 carbon atoms, a monovalent or polyvalent sulfonic acid having 1 to 20 carbon atoms, and an alkyl sulfuric acid having 1 to 3 carbon atoms. Can be mentioned. More specifically, methyl sulfuric acid, ethyl sulfuric acid, p-toluenesulfonic acid, (o-, m-, p-) xylene sulfonic acid, benzenesulfonic acid, dodecylbenzenesulfonic acid, glycolic acid, ethylenediaminetetraacetic acid, citric acid , Benzoic acid, and salicylic acid.
Among these, hydrochloric acid is preferable in the case of an inorganic acid, and a monovalent or polyvalent carboxylic acid having 1 to 10 carbon atoms is preferable in the case of an organic acid, and citric acid is more preferable.
When the transparent liquid softener composition of the present invention contains an acid agent, the content thereof can be appropriately adjusted depending on the type and amount of the component (A), and the pH is in the range described above, and is stored. A degree that does not impair the stability is preferred.
＜（Ｊ）成分：キレート剤＞
本発明の透明液体柔軟剤組成物は、液体柔軟剤組成物の長期保存時の色相変化や染料の褪色及び香りの変質を抑制する観点から、（Ｊ）成分として、キレート剤を用いることが好ましい。なお、本発明における（Ｊ）成分は前記酸剤としての機能も有する。
キレート剤の具体例としては、エタン−１−ヒドロキシ−１，１−ジホスホン酸、エチレンジアミン四酢酸、メチルグリシン二酢酸、ヒドロキシエチルイミノ二酢酸、エチレンジアミン二コハク酸、Ｌ−グルタミン酸−Ｎ，Ｎ−二酢酸、Ｎ−２−ヒドロキシエチルイミノ二酢酸、クエン酸、コハク酸、及びそれらの塩が挙げられる。
塩としては、アルカリ金属塩、アンモニウム塩が好ましく、ナトリウム塩、カリウム塩がより好ましい。
本発明の透明液体柔軟剤組成物が（Ｊ）成分を含有する場合、その含有量は、好ましくは０．００１質量％以上、より好ましくは０．００５質量％以上であり、そして、好ましくは２質量％以下、より好ましく１．５質量％以下、更に好ましくは１．０質量％以下である。なお、（Ｉ）成分の酸剤として（Ｊ）成分に該当する成分が用いられた場合、その量は（Ｊ）成分の量として取り扱うものとする。
<(J) component: chelating agent>
In the transparent liquid softener composition of the present invention, it is preferable to use a chelating agent as the component (J) from the viewpoint of suppressing the color change and the deterioration of the color of the dye and the odor upon long-term storage of the liquid softener composition. . The component (J) in the present invention also has a function as the acid agent.
Specific examples of the chelating agent include ethane-1-hydroxy-1,1-diphosphonic acid, ethylenediaminetetraacetic acid, methylglycinediacetic acid, hydroxyethyliminodiacetic acid, ethylenediaminedisuccinic acid, L-glutamic acid-N, N-two Acetic acid, N-2-hydroxyethyl iminodiacetic acid, citric acid, succinic acid, and salts thereof can be mentioned.
As a salt, an alkali metal salt and an ammonium salt are preferable, and a sodium salt and a potassium salt are more preferable.
When the transparent liquid softener composition of the present invention contains the (J) component, its content is preferably 0.001% by mass or more, more preferably 0.005% by mass or more, and preferably 2 It is not more than mass%, more preferably not more than 1.5 mass%, still more preferably not more than 1.0 mass%. In addition, when the component applicable to (J) component is used as an acid agent of (I) component, the quantity shall be handled as the quantity of (J) component.
＜（Ｋ）成分：徐放性香料＞
また本発明の透明液体柔軟剤組成物には、（Ｆ）成分以外に、徐放性香料として特開２０１４−１２５６８５号公報記載のケイ酸エステル化合物を用いることができる。本発明の透明液体柔軟剤組成物において（Ｋ）成分を用いる場合は、各香料成分の特徴にあった調合により使用する。
<(K) ingredient: sustained release fragrance>
Moreover, in the transparent liquid softener composition of the present invention, in addition to the component (F), a silicate ester compound described in JP-A-2014-125685 can be used as a sustained release fragrance. When the component (K) is used in the transparent liquid softener composition of the present invention, it is used according to the preparation according to the characteristics of each perfume component.
＜その他の成分＞
本発明の透明液体柔軟剤組成物においては、基材の劣化を抑制する観点から、ＢＨＴ等の酸化防止剤を用いることができ、泡立ちを抑制する観点から液体柔軟剤組成物において一般的に用いられる消泡剤を用いることができ、また、審美や長期保存時の着色を防ぐ観点から、液体柔軟剤組成物において一般的に用いられる染料及び顔料を用いることもできる。更に、プロキセルの商品名で市販されている防菌、防黴剤を用いることもできる。
<Other ingredients>
In the transparent liquid softener composition of the present invention, an antioxidant such as BHT can be used from the viewpoint of suppressing deterioration of the base material, and it is generally used in a liquid softener composition from the viewpoint of suppressing foaming. Antifoaming agents can be used, and dyes and pigments generally used in liquid softener compositions can also be used from the viewpoint of preventing coloration during aesthetics and long-term storage. Furthermore, antifungal and antifungal agents marketed under the trade name of Proxel can also be used.
本発明の透明液体柔軟剤組成物は、繊維製品用として好適であり、繊維製品としては、衣料、布帛、寝具、タオル等が挙げられる。 The transparent liquid softener composition of the present invention is suitable for textiles, and examples of textiles include clothing, fabrics, bedding, towels and the like.
［透明液体柔軟剤組成物の製造方法］
本発明の透明液体柔軟剤組成物は、（Ａ）成分を１質量％以上２０質量％以下、（Ｂ）成分を５質量％以上２０質量％以下、（Ｃ）成分を０．５質量％以上１．５質量％以下、（Ｄ）成分を１質量％以上１０質量％以下、及び水を配合してなる透明液体柔軟剤組成物であって、３０℃におけるｐＨが２．０以上５．０以下である透明液体柔軟剤組成物である。
また本発明の透明液体柔軟剤組成物の製造方法は、（Ａ）成分を１質量％以上２０質量％以下、（Ｂ）成分を５質量％以上２０質量％以下、（Ｃ）成分を０．５質量％以上１．５質量％以下、（Ｄ）成分を１質量％以上１０質量％以下、及び水を混合し、３０℃におけるｐＨが２．０以上５．０以下に調整する、透明液体柔軟剤組成物の製造方法である。
本発明の透明液体柔軟剤組成物の製造方法は、本発明の透明液体柔軟剤組成物で述べた事項を適宜適用することができる。（Ａ）成分〜（Ｄ）成分、及び任意成分は、本発明の透明液体柔軟剤組成物で述べたものと同じであり、本発明の透明液体柔軟剤組成物に記載の各成分の含有量は、混合量に置き換えて本発明の透明液体柔軟剤組成物の製造方法に適用される。
[Method of producing transparent liquid softener composition]
The transparent liquid softener composition of the present invention contains 1% by mass to 20% by mass of component (A), 5% by mass to 20% by mass of component (B), 0.5% by mass or more of component (C) 1.5% by mass or less, 1% by mass or more and 10% by mass or less of the component (D), and a transparent liquid softener composition containing water, wherein the pH at 30 ° C. is 2.0 or more and 5.0 It is the transparent liquid softening agent composition which is the following.
In the method for producing the transparent liquid softener composition of the present invention, the component (A) is 1% by mass to 20% by mass, the component (B) is 5% by mass to 20% by mass, and the component (C) is 0. A transparent liquid in which the pH at 30 ° C. is adjusted to 2.0 or more and 5.0 or less by mixing 5% by mass or more and 1.5% by mass or less, 1% by mass or more and 10% by mass or less of the component (D), and water. It is a manufacturing method of a softening agent composition.
The method described in the transparent liquid softener composition of the present invention can be applied as appropriate to the method of producing the transparent liquid softener composition of the present invention. The components (A) to (D) and the optional components are the same as those described for the transparent liquid softener composition of the present invention, and the content of each component described in the transparent liquid softener composition of the present invention Is applied to the method for producing the transparent liquid softener composition of the present invention in place of the mixing amount.
実施例で使用した成分を以下に示す。 The components used in the examples are shown below.
＜（Ａ）成分＞
（Ａ−１）：下記合成例ａ−１で製造された４級アンモニウム塩化合物
〔合成例ａ−１：（Ａ−１）の製造〕
トリエタノールアミンとＲＣＯＯＨで表される脂肪酸（組成は後述の通り）とを、反応モル比（脂肪酸／トリエタノールアミン）が１．８７／１で、エステル化反応させ、一般式（Ａ１）で表される化合物の前駆体であるアミン化合物を含むエステル化反応物を得た。
エステル化反応物中には、未反応の脂肪酸が１質量％含まれていた。エステル化反応物中のアミン化合物のアミンに対して、メチル基が０．９６当量となるように、ジメチル硫酸で４級化反応を行った後、エタノールを添加した。
<(A) component>
(A-1): quaternary ammonium salt compound produced in the following synthesis example a-1 [synthesis example a-1: production of (A-1)]
The esterification reaction of triethanolamine and a fatty acid represented by RCOOH (the composition is as described later) is carried out at a reaction molar ratio (fatty acid / triethanolamine) of 1.87 / 1, and is represented by the general formula (A1) An esterification reaction product containing an amine compound which is a precursor of the compound to be
The esterification reaction product contained 1% by mass of unreacted fatty acid. With respect to the amine of the amine compound in the esterification reaction product, after the quaternization reaction was performed with dimethyl sulfuric acid so that the methyl group was 0.96 equivalents, ethanol was added.
得られた反応物をＨＰＬＣ法で各成分の組成比を分析し、臭化テトラオクチルアンモニウムを内部標準物質として使用し定量した結果、得られた反応物は、（Ａ）成分である（Ａ−１）成分を６６質量％、エタノール１５質量％、未反応アミン塩（メチル硫酸塩として）１７質量％、未反応脂肪酸１質量％、微量のトリエタノールアミン４級化物及びその他微量成分を含み、このうち一般式（Ａ１）において、Ｒ１ａがアシル基、Ｒ２ａが水素原子、Ｒ３ａが−Ｃ２Ｈ４−ＯＲ４ａ、Ｒ４ａが水素原子、Ｒ５ａがメチル基であって、Ｘ−がメチル硫酸である化合物が（Ａ−１）成分中２２質量％、一般式（Ａ１）において、Ｒ１ａ及びＲ２ａがアシル基、Ｒ３ａが−Ｃ２Ｈ４−ＯＲ４ａ、Ｒ４ａが水素原子、Ｒ５ａがメチル基であって、Ｘ−がメチル硫酸である化合物が（Ａ−１）成分中５８質量％、一般式（Ａ１）において、Ｒ１ａ及びＲ２ａがアシル基、Ｒ３ａが−Ｃ２Ｈ４−ＯＲ４ａ、Ｒ４ａがアシル基であり、Ｒ５ａがメチル基であって、Ｘ−がメチル硫酸である化合物が（Ａ−１）成分中２０質量％であった。また４級化率は８０質量％であった。 The composition of each component was analyzed by the HPLC method, and the resulting reactant was quantified using tetraoctylammonium bromide as an internal standard substance. The resulting reactant was the component (A) (A-). 1) containing 66% by mass of component, 15% by mass of ethanol, 17% by mass of unreacted amine salt (as methyl sulfate), 1% by mass of unreacted fatty acid, trace of triethanolamine quaternized and other minor components, Among them, in the general formula (A1), R 1a is an acyl group, R 2a is a hydrogen atom, R 3a is -C 2 H 4 -OR 4a , R 4a is a hydrogen atom, R 5a is a methyl group, and X - is The compound which is methyl sulfuric acid is 22% by mass in the component (A-1), and in the general formula (A1), R 1a and R 2a are acyl groups, R 3a is -C 2 H 4 -OR 4a , and R 4a is a hydrogen atom , R 5a is methyl A is, X - compound is methyl sulfate (A1) component 58 mass%, in the general formula (A1), R 1a and R 2a is an acyl group, R 3a is -C 2 H 4 -OR 4a, R 4a is an acyl group, R 5a is a methyl group, X - is a 20% by weight in the compound is methyl sulfate (a-1) component. The quaternization rate was 80% by mass.
なお（Ａ−１）を製造するための反応に用いたＲＣＯＯＨの組成を以下に示す。
オレイン酸：８０質量％
リノール酸：１０質量％
リノレン酸：２質量％
ステアリン酸：２質量％
パルミチン酸：６質量％
前記組成は、原料に使用した脂肪酸をガスクロマトグラフィーで組成分析し、各脂肪酸の面積％を質量％とみなした。
The composition of RCOOH used in the reaction for producing (A-1) is shown below.
Oleic acid: 80% by mass
Linoleic acid: 10% by mass
Linolenic acid: 2% by mass
Stearic acid: 2% by mass
Palmitic acid: 6% by mass
In the composition, fatty acids used as raw materials were compositionally analyzed by gas chromatography, and area% of each fatty acid was regarded as mass%.
さらに、後述する保存安定性評価の加速度試験のため、反応物を耐熱ビン(PYREX（登録商標）広口メジュームびん 赤耐熱キャップ付 ５００ｍｌ)に上記の合成例ａ−１の方法で製造された（Ａ−１）成分を含む４級アンモニウム塩反応物４００ｇとイオン交換水１００ｇとを入れ均一に混合して、混合液を得た。混合液を８０℃±２の恒温槽に入れることで４級アンモニウム塩化合物の加水分解を行った。加水分解反応の進行具合はＪＩＳ Ｋ ００７０−１９９２に記載の方法で酸価（ＡＶ）及び鹸化価（ＳＶ）を測定することで確認を行い、加水分解率は３０．２％であった。なお加水分解率は以下に示す式(１)において求められる。
加水分解率(％)＝[(加水分解後の混合液のＡＶ)−(加水分解前の混合液のＡＶ)]／[(加水分解前の混合液のＳＶ)−(加水分解前の混合液のＡＶ)]×１００ 式（１）
実施例、比較例の液体柔軟剤組成物は、後述する保存安定性評価の加速度試験のために合成例ａ−１の方法で製造された４級アンモニウム塩反応物を更に加水分解したものを配合しており、表２中の（Ａ−１）の含有量は加水分解処理を行う前の（Ａ−１）成分濃度に換算している。実際の（Ａ−１）の含有量は、表中に記載の濃度よりも少なくなっている。
Furthermore, for the acceleration test of storage stability evaluation described later, the reaction product was manufactured in a heat-resistant bottle (PYREX (registered trademark) wide-mouthed medium bottle with red heat-resistant cap 500 ml) according to the method of Synthesis Example a-1 above (A -1) 400 g of a quaternary ammonium salt reactant containing the component and 100 g of ion-exchanged water were uniformly mixed to obtain a mixed solution. The mixed solution was placed in a thermostat at 80 ° C. ± 2 to hydrolyze the quaternary ammonium salt compound. The progress of the hydrolysis reaction was confirmed by measuring the acid value (AV) and the saponification value (SV) according to the method described in JIS K 0070-1992, and the hydrolysis rate was 30.2%. In addition, a hydrolysis rate is calculated | required in Formula (1) shown below.
Hydrolysis rate (%) = [(AV of mixture after hydrolysis)-(AV of mixture before hydrolysis)] / [(SV of mixture before hydrolysis)-(mixture before hydrolysis) AV)] × 100 Formula (1)
The liquid softener compositions of Examples and Comparative Examples were prepared by further hydrolyzing the quaternary ammonium salt reactant produced by the method of Synthesis Example a-1 for the acceleration test of storage stability evaluation described later. The content of (A-1) in Table 2 is converted to the concentration of the (A-1) component before the hydrolysis treatment. The actual content of (A-1) is less than the concentration described in the table.
＜（Ｂ）成分＞
（Ｂ−１）：ポリオキシエチレン(オキシエチレン基の平均付加モル数３)フェニルエーテル、一般式（Ｂ１）中、ｎが３の化合物
<(B) component>
(B-1): polyoxyethylene (average addition mole number of oxyethylene group 3) phenyl ether, in the general formula (B1), a compound in which n is 3
＜（Ｃ）成分＞
（Ｃ−１）：Ｎ−エチル−Ｎ，Ｎ−ジメチル−Ｎ−テトラデシルアンモニウムエチル硫酸塩、一般式（Ｃ１）中、Ｒ１ｃが炭素数１４のアルキル基、Ｒ２ｃ及びＲ３ｃがメチル基、Ｒ４ｃがエチル基、Ｙ−がエチル硫酸イオンの化合物
＜（Ｃ’）成分（（Ｃ）成分の比較成分）＞
（Ｃ’−１）：Ｎ−ベンジル−Ｎ，Ｎ−ジメチル−Ｎ−アルキル（Ｃ１２〜１６）アンモニウムクロライド、一般式（Ｃ１）中、Ｒ１ｃが炭素数１２〜１６のアルキル基、Ｒ２ｃ及びＲ３ｃがメチル基、Ｒ４ｃがベンジル基、Ｙ−が塩化物イオンの化合物
（Ｃ’−２）：Ｎ，Ｎ−ジデシル−Ｎ−エチル−Ｎ−メチルアンモニウムエチル硫酸塩、一般式（Ｃ１）中、Ｒ１ｃ及びＲ２ｃが炭素数１０のアルキル基、Ｒ３ｃがエチル基、Ｒ４ｃがメチル基、Ｙ−がエチル硫酸イオンの化合物
<(C) component>
(C-1): N-ethyl-N, N-dimethyl-N-tetradecyl ammonium ethyl sulfate, in the general formula (C1), R 1c is an alkyl group having 14 carbon atoms, R 2c and R 3c are methyl groups , R 4c is an ethyl group, Y - is a compound of the ethyl sulfate ion <(C ′) component (comparative component of (C) component)>
(C′-1): N-benzyl-N, N-dimethyl-N-alkyl (C12-16) ammonium chloride, in the general formula (C1), R 1c is an alkyl group having 12 to 16 carbon atoms, R 2c and R 3c is a methyl group, R 4c is a benzyl group, Y - is a compound of the chloride ions (C'-2): N, N- didecyl -N- ethyl -N- methyl ammonium ethyl sulfate, the general formula (C1) Among them, compounds wherein R 1c and R 2c are an alkyl group having 10 carbon atoms, R 3c is an ethyl group, R 4c is a methyl group, and Y - is an ethyl sulfate ion
＜（Ｄ）成分＞
（Ｄ−１）：ポリオキシエチレン(オキシエチレン基の平均付加モル数８)ラウリルエーテル、一般式（Ｄ１）中、Ｒ１ｄが炭素数１２のアルキル基、ｐが８の化合物
<(D) component>
(D-1): polyoxyethylene (average added mole number of oxyethylene group: 8) lauryl ether, in the general formula (D1), a compound wherein R 1d is an alkyl group having 12 carbon atoms and p is 8
＜（Ｅ）成分＞
（Ｅ−１）：ポリオキシエチレン(オキシエチレン基の平均付加モル数２９)ラウリルエーテル、一般式（Ｅ１）中、Ｒ１ｅが炭素数１２のアルキル基、ｑが２９の化合物
<(E) component>
(E-1): polyoxyethylene (average added mole number of oxyethylene group: 29) lauryl ether, in the general formula (E1), a compound wherein R 1e is an alkyl group having 12 carbon atoms and q is 29
＜（Ｆ）成分＞
（Ｆ−１）：表１記載の香料
<(F) component>
(F-1): The fragrance described in Table 1
＜（Ｇ）成分＞
（Ｇ−１）：エチレングリコール
（Ｇ−２）：グリセリン
＜（Ｉ）成分＞
（Ｉ−１）：２．８８Ｎ塩酸、(１０質量％塩酸)
＜（Ｊ）成分＞
（Ｊ−１）：メチルグリシン二酢酸３ナトリウム、ＴＲＩＬＯＮ Ｍ ＬＩＱＵＩＤ(商標名)、ＢＡＳＦ ＳＥ社製
＜その他成分＞
防腐剤：１，２-ベンゾイソチアゾール-３（２Ｈ）-オン、プロキセルＢＤＮ（商標名）、ＬＯＮＺＡ社製
脂肪酸：パルミチン酸とステアリン酸の混合脂肪酸（質量比７：２）
消泡剤：ＤＯＷ ＣＯＲＮＩＮＧ ＴＯＲＡＹ １３１５ ＡＮＴＩＦＯＡＭ ＣＯＮＣＥＮＴＲＡＴＥ(商標名)、東レ・ダウコーニング社製
<(G) component>
(G-1): Ethylene glycol (G-2): Glycerin <(I) component>
(I-1): 2.88 N hydrochloric acid, (10 mass% hydrochloric acid)
<(J) component>
(J-1): Methyl glycine diacetate trisodium, TRILON M LIQUID (trade name), manufactured by BASF SE <other components>
Preservative: 1,2-benzisothiazol-3 (2H) -one, Proxel BDN (trade name), LONZA fatty acid: mixed fatty acid of palmitic acid and stearic acid (mass ratio 7: 2)
Antifoaming agent: DOW CORNING TORAY 1315 ANTIFOAM CONCENTRATE (trade name), manufactured by Toray Dow Corning
〔実施例１〜５及び比較例１〜８〕
（１）透明液体柔軟剤組成物の製造
表２に示す配合組成となるように各成分を混合することにより、透明液体柔軟剤組成物を調製した。具体的には、以下の通りである。なお、（Ａ）成分は合成例ａ−１で製造され、その後加速試験のために加水分解処理を行った４級アンモニウム塩反応物として配合した。表中の組成の質量％は、有効分の質量％である。その他の成分の量は、イオン交換水の残部に加えた。
[Examples 1 to 5 and Comparative Examples 1 to 8]
(1) Production of Transparent Liquid Softener Composition A transparent liquid softener composition was prepared by mixing each component so as to have the composition shown in Table 2. Specifically, it is as follows. In addition, (A) component was manufactured by the synthesis example a-1, and it mix | blended as a quaternary ammonium salt reactant which performed the hydrolysis process for an acceleration test after that. The mass% of the composition in the table is the mass% of the effective component. The amounts of the other components were added to the remainder of the ion exchanged water.
３００ｍＬビーカーに、透明液体柔軟剤組成物のできあがり量が２００ｇとなるのに必要な量の（Ａ）成分、（Ｂ）成分、（Ｃ）成分又は（Ｃ’）成分、（Ｄ）成分、（Ｆ）成分、（Ｇ）成分を入れ均一に溶解するように、必要に応じて撹拌羽根を用いて撹拌することにより混合液を得た。なお、撹拌羽根としては、直径が５ｍｍの撹拌棒の回転中心軸を基準として、長辺が９０度方向になるように配置された撹拌羽根であって、羽根の数３枚、羽根の長辺／短辺＝３ｃｍ／１．５ｃｍ、回転面に対して４５度の角度で羽根が設置されたものを用いた。 In a 300 mL beaker, the amount of (A) component, (B) component, (C) component or (C ') component, (D) component, (D) component, the amount required for the finished liquid softener composition to reach 200 g. The mixed liquid was obtained by stirring using a stirring blade as needed so that the F component and (G) component may be added and melt | dissolved uniformly. In addition, as a stirring blade, it is a stirring blade arrange | positioned so that a long side may become a 90 degree direction on the basis of the rotation central axis of the stirring rod of 5 mm in diameter, Comprising: The number of 3 blades, the long side of a blade / A short side = 3 cm / 1.5 cm, what used the blade installed at an angle of 45 degrees with respect to the rotation surface.
混合液を、前記撹拌羽根で撹拌（３００ｒ／ｍ）した。これに、脂肪酸、消泡剤と共に６５℃で加熱溶解させた（Ｅ）成分を1分間掛けて投入し、投入終了後、３分間撹拌した。
次に、透明液体柔軟剤組成物のできあがり量が２００ｇとなるのに必要な量の９０質量％に相当する量のイオン交換水を１分間掛けて投入し、投入終了後、５分間撹拌した。これに、（Ｉ）成分、（Ｊ）成分、防腐剤を順次投入し、５分間撹拌した。更に、できあがり質量（２００ｇ）となるようにイオン交換水を加え、５分間撹拌して透明液体柔軟剤組成物を得た。
The mixture was stirred (300 r / m) with the stirring blade. The component (E) heated and dissolved at 65 ° C. together with the fatty acid and the antifoaming agent was added to this over 1 minute, and after the end of the addition, it was stirred for 3 minutes.
Next, ion exchange water of an amount equivalent to 90% by mass of the amount necessary for the finish of the transparent liquid softener composition to reach 200 g was charged over 1 minute, and stirred for 5 minutes after the charging was completed. The component (I), the component (J) and the preservative were sequentially added to this, and stirred for 5 minutes. Furthermore, ion-exchanged water was added to a finished mass (200 g), and the mixture was stirred for 5 minutes to obtain a transparent liquid softener composition.
得られた透明液体柔軟剤組成物について濁度を測定した。具体的には、測定セルとして光路長５０ｍｍの石英セルを使用し、標準液として蒸留水を用い、曇り度計（日本電色工業のＮＤＨ２０００）を用いて測定した。実施例及び比較例で得られた液体柔軟剤組成物の濁度は、全て５０．０ｍｇ／Ｌ未満であり、外観上透明な液体柔軟剤組成物であった。 The turbidity of the resulting clear liquid softener composition was measured. Specifically, a quartz cell with an optical path length of 50 mm was used as a measurement cell, distilled water was used as a standard solution, and measurement was performed using a haze meter (NDH 2000 manufactured by Nippon Denshoku Kogyo). The turbidity of the liquid softener compositions obtained in Examples and Comparative Examples was all less than 50.0 mg / L, and the appearance was a liquid softener composition that was transparent in appearance.
（２）保存安定性評価
外観上透明な液体柔軟剤組成物は、長期保存によって、（Ａ）成分である柔軟基材が加水分解することで生成する脂肪酸により、保存状況によっては外観を損なう場合がある。本評価では、脂肪酸の発生の可能性を考慮し、上記の液体柔軟剤組成物の調製方法の通り、（Ａ）成分を予め、ある程度加水分解させた状態で液体柔軟剤組成物に配合させ、さらに脂肪酸を液体柔軟剤組成物に配合させた上で、加速度試験的に液体柔軟剤組成物の保存安定性を調べた。
表２の調製した透明液体柔軟剤組成物３５ｇを、広口規格ビン(PS-No.6)に注ぎ、密封したものを、常温（２５℃）、高温（４０℃）、低温（−５℃）の各温度の恒温室に２０日間貯蔵後、目視で外観を観察し、下記の評価基準で判定した。結果を表２に示す。
○：モヤないし濁り及び沈殿物が見られない。
×：モヤ、濁りもしくは沈殿物が見られる。
(2) Evaluation of storage stability In the case of a liquid softener composition that is transparent in appearance, the appearance is damaged depending on the storage condition due to the fatty acid that is generated by hydrolysis of the flexible substrate which is the component (A). There is. In this evaluation, in consideration of the possibility of generation of fatty acid, the component (A) is previously hydrolyzed to a certain extent as in the method of preparing the liquid softener composition, and the liquid softener composition is compounded, Furthermore, the fatty acid was incorporated into the liquid softener composition, and the storage stability of the liquid softener composition was examined by an acceleration test.
35 g of the prepared transparent liquid softener composition of Table 2 is poured into a wide-mouthed bottle (PS-No. 6), and the sealed one is normal temperature (25 ° C.), high temperature (40 ° C.), low temperature (-5 ° C.) After storage for 20 days in a temperature-controlled room at each temperature, the appearance was visually observed and judged according to the following evaluation criteria. The results are shown in Table 2.
○: No haze or turbidity and no precipitate observed.
X: Moy, turbidity or precipitate observed.
なお、本願実施例の透明液体柔軟剤組成物は、上記保存安定性評価前及び評価後のいずれの場合においても、衣類に対して良好な柔軟性を与えるものであった。 In addition, the transparent liquid softening agent composition of an Example of this application gave favorable softness | flexibility with respect to clothing also in any case before and after the said storage stability evaluation.
Claims (5)
＜（Ａ）成分＞
下記一般式（Ａ１）で表される４級アンモニウム塩化合物であって、アシル基を脂肪酸と見做した場合に、オレイン酸、リノール酸及びリノレン酸の割合が、アシル基を構成している全脂肪酸の６０質量％以上１００質量％以下である４級アンモニウム塩化合物
〔式中、Ｒ１ａ、Ｒ２ａはそれぞれ独立して、炭素数１６以上２２以下の脂肪酸からＯＨを除いた残基（アシル基という）、又は水素原子であり、ただし、Ｒ１ａ、Ｒ２ａの少なくとも１つは、アシル基であり、Ｒ３ａは炭素数１以上３以下のアルキル基又は−Ｃ２Ｈ４−ＯＲ４ａであり、Ｒ４ａは炭素数１６以上２２以下のアシル基又は水素原子であり、Ｒ５ａは炭素数１以上３以下のアルキル基であり、Ｘ−は陰イオンである。〕
＜（Ｂ）成分＞
下記一般式（Ｂ１）で表される溶剤
〔式中、ｎは、オキシエチレン基の平均付加モル数であり、１以上１５以下の数である。〕
＜（Ｃ）成分＞
下記一般式（Ｃ１）で表される４級アンモニウム塩化合物
〔式中、Ｒ１ｃは炭素数１２以上１８以下の炭化水素基であり、Ｒ２ｃ、Ｒ３ｃ、Ｒ４ｃは、それぞれ独立に、炭素数１以上３以下のアルキル基である。Ｙ−は陰イオンである。〕
＜（Ｄ）成分＞
下記一般式（Ｄ１）で表される非イオン性界面活性剤
Ｒ１ｄ−Ｏ−（Ｃ２Ｈ４Ｏ）ｐ−Ｈ （Ｄ１）
〔式中、Ｒ１ｄは炭素数１０以上１８以下の炭化水素基であり、また、pはオキシエチレン基の平均付加モル数であり、３以上１０以下の数である。〕 1 mass% or more and 20 mass% or less of the following (A) component, 5 mass% or more and 20 mass% or less of the following (B) component, 0.5 mass% or more and 1.5 mass% or less of the following (C) component The transparent liquid softening agent composition which contains 1 mass% or more and 10 mass% or less of components (D), and water and whose pH in 30 degreeC is 2.0 or more and 5.0 or less.
<(A) component>
It is a quaternary ammonium salt compound represented by the following general formula (A1), and when the acyl group is regarded as a fatty acid, all the proportions of oleic acid, linoleic acid and linolenic acid make up the acyl group Quaternary ammonium salt compound that is 60 mass% or more and 100 mass% or less of fatty acid
[Wherein, R 1a and R 2a each independently represent a residue obtained by removing OH from a fatty acid having 16 to 22 carbon atoms (referred to as an acyl group), or a hydrogen atom, provided that R 1a and R 2a At least one is an acyl group, R 3a is an alkyl group having 1 to 3 carbon atoms or -C 2 H 4 -OR 4a , and R 4a is an acyl group having 16 to 22 carbon atoms or a hydrogen atom R 5a is an alkyl group having 1 or more and 3 or less carbon atoms, and X − is an anion. ]
<(B) component>
Solvent represented by the following general formula (B1)
[In the formula, n is the average added mole number of the oxyethylene group, and is a number of 1 or more and 15 or less. ]
<(C) component>
Quaternary ammonium salt compound represented by the following general formula (C1)
[Wherein, R 1c is a hydrocarbon group having 12 to 18 carbon atoms, and R 2c , R 3c , and R 4c are each independently an alkyl group having 1 to 3 carbon atoms. Y - is an anion. ]
<(D) component>
Nonionic surfactant represented by the following general formula (D1)
R 1d -O- (C 2 H 4 O) p -H (D1)
[Wherein, R 1d is a hydrocarbon group having 10 to 18 carbon atoms, and p is the average addition mole number of the oxyethylene group, and is a number of 3 to 10]. ]
＜（Ｅ）成分＞
下記一般式（Ｅ１）で表される非イオン性界面活性剤
Ｒ１ｅ−Ｏ−（Ｃ２Ｈ４Ｏ）ｑ−Ｈ （Ｅ１）
〔式中、Ｒ１ｅは炭素数１０以上１８以下の炭化水素基であり、また、ｑはオキシエチレン基の平均付加モル数であり、１０を超え６０以下の数である。〕 Furthermore, the transparent liquid softening agent composition of Claim 1 containing the following (E) component.
<(E) component>
Nonionic surfactant represented by the following general formula (E1)
R 1e -O- (C 2 H 4 O) q -H (E 1)
[Wherein, R 1 e is a hydrocarbon group having 10 to 18 carbon atoms, and q is the average addition mole number of the oxyethylene group, and is a number of more than 10 and 60 or less. ]
The transparent liquid softener composition according to claim 4, which contains the component (F) in an amount of 1.0% by mass or more and 2.0% by mass or less.
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