JP2012154010A - Composition of softener - Google Patents
Composition of softener Download PDFInfo
- Publication number
- JP2012154010A JP2012154010A JP2011016297A JP2011016297A JP2012154010A JP 2012154010 A JP2012154010 A JP 2012154010A JP 2011016297 A JP2011016297 A JP 2011016297A JP 2011016297 A JP2011016297 A JP 2011016297A JP 2012154010 A JP2012154010 A JP 2012154010A
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- hydrogen atom
- represented
- monomer
- 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.)
- Pending
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- 239000000203 mixture Substances 0.000 title claims abstract description 33
- 239000000178 monomer Substances 0.000 claims abstract description 37
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 16
- 229920000642 polymer Polymers 0.000 claims abstract description 16
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 51
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 239000004902 Softening Agent Substances 0.000 claims description 11
- 239000002736 nonionic surfactant Substances 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 9
- 229910017053 inorganic salt Inorganic materials 0.000 claims description 5
- 125000000129 anionic group Chemical group 0.000 claims description 4
- 239000003093 cationic surfactant Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 239000000470 constituent Substances 0.000 claims 1
- 239000000835 fiber Substances 0.000 abstract description 26
- 230000000694 effects Effects 0.000 abstract description 14
- -1 hydroxyethyl group Chemical group 0.000 description 38
- 229910052757 nitrogen Inorganic materials 0.000 description 24
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000004952 Polyamide Substances 0.000 description 5
- 229920002647 polyamide Polymers 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000013074 reference sample Substances 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 0 CC(*CN(C)*)=C Chemical compound CC(*CN(C)*)=C 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229920000297 Rayon Polymers 0.000 description 3
- 229920002334 Spandex Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 235000011167 hydrochloric acid Nutrition 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000005395 methacrylic acid group Chemical group 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 239000002964 rayon Substances 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000004759 spandex Substances 0.000 description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 3
- 229920002994 synthetic fiber Polymers 0.000 description 3
- 239000012209 synthetic fiber Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 2
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 241000282320 Panthera leo Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 239000012986 chain transfer agent Substances 0.000 description 2
- 235000015165 citric acid Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000004220 glutamic acid Substances 0.000 description 2
- 235000013922 glutamic acid Nutrition 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 239000007870 radical polymerization initiator Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- 239000004753 textile 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
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- DCCWEYXHEXDZQW-BYPYZUCNSA-N (2s)-2-[bis(carboxymethyl)amino]butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)N(CC(O)=O)CC(O)=O DCCWEYXHEXDZQW-BYPYZUCNSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- NVJUHMXYKCUMQA-UHFFFAOYSA-N 1-ethoxypropane Chemical compound CCCOCC NVJUHMXYKCUMQA-UHFFFAOYSA-N 0.000 description 1
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
- BORYKGCSYGMNTB-UHFFFAOYSA-N 14-methylpentadecyl prop-2-enoate Chemical compound CC(C)CCCCCCCCCCCCCOC(=O)C=C BORYKGCSYGMNTB-UHFFFAOYSA-N 0.000 description 1
- KOGYJXKLQYJHDZ-UHFFFAOYSA-N 2,5-dihydro-1H-imidazol-1-ium methyl sulfate Chemical compound C1[NH2+]CN=C1.COS([O-])(=O)=O KOGYJXKLQYJHDZ-UHFFFAOYSA-N 0.000 description 1
- GZMAAYIALGURDQ-UHFFFAOYSA-N 2-(2-hexoxyethoxy)ethanol Chemical compound CCCCCCOCCOCCO GZMAAYIALGURDQ-UHFFFAOYSA-N 0.000 description 1
- CCJAYIGMMRQRAO-UHFFFAOYSA-N 2-[4-[(2-hydroxyphenyl)methylideneamino]butyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCCCN=CC1=CC=CC=C1O CCJAYIGMMRQRAO-UHFFFAOYSA-N 0.000 description 1
- CGMMPMYKMDITEA-UHFFFAOYSA-N 2-ethylbenzoic acid Chemical compound CCC1=CC=CC=C1C(O)=O CGMMPMYKMDITEA-UHFFFAOYSA-N 0.000 description 1
- RMGHERXMTMUMMV-UHFFFAOYSA-N 2-methoxypropane Chemical compound COC(C)C RMGHERXMTMUMMV-UHFFFAOYSA-N 0.000 description 1
- JNDVNJWCRZQGFQ-UHFFFAOYSA-N 2-methyl-N,N-bis(methylamino)hex-2-enamide Chemical compound CCCC=C(C)C(=O)N(NC)NC JNDVNJWCRZQGFQ-UHFFFAOYSA-N 0.000 description 1
- BPEZHABUVGDGNE-UHFFFAOYSA-N 2-methyl-n-tetradecylprop-2-enamide Chemical compound CCCCCCCCCCCCCCNC(=O)C(C)=C BPEZHABUVGDGNE-UHFFFAOYSA-N 0.000 description 1
- ZDFKSZDMHJHQHS-UHFFFAOYSA-N 2-tert-butylbenzoic acid Chemical compound CC(C)(C)C1=CC=CC=C1C(O)=O ZDFKSZDMHJHQHS-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 229920002972 Acrylic fiber Polymers 0.000 description 1
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- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- HEWOYRIZKVTLBS-UHFFFAOYSA-N prop-1-en-2-yl decanoate Chemical compound CCCCCCCCCC(=O)OC(C)=C HEWOYRIZKVTLBS-UHFFFAOYSA-N 0.000 description 1
- HKKOVPPBQKFVNN-UHFFFAOYSA-N prop-1-en-2-yl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(C)=C HKKOVPPBQKFVNN-UHFFFAOYSA-N 0.000 description 1
- DWQHEUIXQNVFOK-UHFFFAOYSA-N prop-1-en-2-yl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OC(C)=C DWQHEUIXQNVFOK-UHFFFAOYSA-N 0.000 description 1
- VPJDULFXCAQHRC-UHFFFAOYSA-N prop-2-enylurea Chemical compound NC(=O)NCC=C VPJDULFXCAQHRC-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- NWCXWRNETRHMRW-UHFFFAOYSA-N tetracosyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCOC(=O)C=C NWCXWRNETRHMRW-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- IIBYPFWXQQDGFC-UHFFFAOYSA-N trimethyl-[2-(2-methylprop-2-enoylamino)propyl]azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(C)NC(=O)C(C)=C IIBYPFWXQQDGFC-UHFFFAOYSA-N 0.000 description 1
- RRHXZLALVWBDKH-UHFFFAOYSA-M trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)OCC[N+](C)(C)C RRHXZLALVWBDKH-UHFFFAOYSA-M 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
本発明は、柔軟剤組成物に関する。 The present invention relates to a softener composition.
１分子中に１個又は２個の長鎖アルキル基を有する４級アンモニウム塩や３級アミンの酸塩等のカチオン性界面活性剤が、繊維への柔軟性付与効果を有することは公知の技術であるが、その効果は十分とはいえなかった。そこで、柔軟性付与効果の向上を目的として、カチオン基を有する特定構造のモノマーからなるポリマーを柔軟剤組成物に配合したものが提案されているが（特許文献１、２）、それらの柔軟性付与効果も未だ満足できるものではない。 It is known that cationic surfactants such as quaternary ammonium salts and tertiary amine acid salts having one or two long-chain alkyl groups in one molecule have an effect of imparting flexibility to fibers. However, the effect was not sufficient. In view of this, for the purpose of improving the flexibility-imparting effect, a polymer composed of a monomer having a specific structure having a cationic group is proposed in a softener composition (Patent Documents 1 and 2). The grant effect is still not satisfactory.
本発明は、繊維に対する柔軟性付与効果に優れた柔軟剤組成物を提供することにある。 This invention is providing the softener composition excellent in the softness | flexibility provision effect with respect to a fiber.
本発明者等は、上記の課題を解決すべく鋭意研究を重ねた結果、本発明に到達した。すなわち、本発明は、下記一般式（１）で表される単量体（ａ）を構成単位とする高分子化合物（Ａ）を含有してなる柔軟剤組成物である。
本発明の柔軟剤組成物は、繊維に対する柔軟性付与効果に優れるという効果を奏する。 The softener composition of the present invention has an effect of being excellent in the effect of imparting flexibility to fibers.
本発明の柔軟剤組成物は、一般式（１）で表される単量体（ａ）を構成単位とする高分子化合物（Ａ）を含有してなる。
一般式（１）におけるＲ１は、水素原子又はメチル基である。
一般式（１）におけるＸは、−ＣＯＮ（Ｒ２）Ｒ３、−ＣＨ２ＮＨＣＯＮ（Ｒ４）Ｒ５又は−ＣＨ２ＮＨＣＯＯＲ６で表される基である。Ｘのうち、柔軟性付与効果の観点から好ましいのは−ＣＯＮＲ２−Ｒ３で表される基である。
Ｒ２及びＲ３は、それぞれ独立に水素原子、炭素数１〜４のアルキル基又は炭素数１〜３のヒドロキシアルキル基である。
Ｒ４、Ｒ５及びＲ６は、それぞれ独立に水素原子又は炭素数１〜４のアルキル基である。
炭素数１〜４のアルキル基としては、メチル基、エチル基、ｎ−プロピル基、イソプロピル基、ｎ−ブチル基、イソブチル基及びｔ−ブチル基が挙げられる。
炭素数１〜３のヒドロキシアルキル基としては、ヒドロキシメチル基、ヒドロキシエチル基、ヒドロキシ−ｎ−プロピル基及びヒドロキシイソプロピル基が挙げられる。
Ｒ２及びＲ３のうち、柔軟性付与効果の観点から好ましいのは、水素原子、メチル基、ヒドロキシメチル基及びヒドロキシエチル基である。
Ｒ４、Ｒ５及びＲ６のうち、柔軟性付与効果の観点から好ましいのは水素原子及びメチル基である。
The softening agent composition of this invention contains the high molecular compound (A) which uses the monomer (a) represented by General formula (1) as a structural unit.
R 1 in the general formula (1) is a hydrogen atom or a methyl group.
X in the general formula (1) is a group represented by —CON (R 2 ) R 3 , —CH 2 NHCON (R 4 ) R 5 or —CH 2 NHCOOR 6 . Of X, a group represented by —CONR 2 —R 3 is preferable from the viewpoint of imparting flexibility.
R 2 and R 3 are each independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a hydroxyalkyl group having 1 to 3 carbon atoms.
R 4 , R 5 and R 6 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
Examples of the alkyl group having 1 to 4 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group and t-butyl group.
Examples of the hydroxyalkyl group having 1 to 3 carbon atoms include a hydroxymethyl group, a hydroxyethyl group, a hydroxy-n-propyl group, and a hydroxyisopropyl group.
Of R 2 and R 3 , a hydrogen atom, a methyl group, a hydroxymethyl group, and a hydroxyethyl group are preferable from the viewpoint of imparting flexibility.
Of R 4 , R 5 and R 6 , preferred are a hydrogen atom and a methyl group from the viewpoint of imparting flexibility.
一般式（１）で表される単量体（ａ）のうち、Ｘが−ＣＯＮ（Ｒ２）Ｒ３で表される基を有するものとしては、アクリルアミド、メタクリルアミド、Ｎ−ヒドロキシメチルアクリルアミド、Ｎ−ヒドロキシメチルメタクリルアミド、Ｎ−ヒドロキシエチルアクリルアミド、Ｎ−ヒドロキシエチルメタクリルアミド、Ｎ−メチルアクリルアミド、Ｎ−メチルメタクリルアミド、Ｎ−エチルアクリルアミド、Ｎ−エチルメタクリルアミド、Ｎ−イソプロピルアクリルアミド、Ｎ−イソプロピルメタクリルアミド、Ｎ−ｔ−ブチルアクリルアミド、Ｎ−ｔ−ブチルメタクリルアミド、Ｎ，Ｎ−ジメチルアクリルアミド、Ｎ，Ｎ−ジメチルメタクリルアミド、Ｎ，Ｎ−ジエチルアクリルアミド及びＮ，Ｎ−ジエチルメタクリルアミド等が挙げられる。 Among the monomers (a) represented by the general formula (1), X having a group represented by —CON (R 2 ) R 3 includes acrylamide, methacrylamide, N-hydroxymethylacrylamide, N-hydroxymethyl methacrylamide, N-hydroxyethyl acrylamide, N-hydroxyethyl methacrylamide, N-methyl acrylamide, N-methyl methacrylamide, N-ethyl acrylamide, N-ethyl methacrylamide, N-isopropyl acrylamide, N-isopropyl Examples include methacrylamide, Nt-butylacrylamide, Nt-butylmethacrylamide, N, N-dimethylacrylamide, N, N-dimethylmethacrylamide, N, N-diethylacrylamide and N, N-diethylmethacrylamide. Be
一般式（１）で表される単量体（ａ）のうち、Ｘが−ＣＨ２ＮＨＣＯＮ（Ｒ４）Ｒ５で表される基を有するものとしては、アリル尿素及びＮ−メチル−Ｎ’−アリル尿素等が挙げられる。 Among the monomers (a) represented by the general formula (1), X having a group represented by —CH 2 NHCON (R 4 ) R 5 includes allyl urea and N-methyl-N ′. -Allylurea etc. are mentioned.
一般式（１）で表される単量体（ａ）のうち、Ｘが−ＣＨ２ＮＨＣＯＯＲ６で表される基を有するものとしては、Ｎ−（ｔ−ブトキシカルボニル)アリルアミン等が挙げられる。 Among the monomers (a) represented by the general formula (1), N- (t-butoxycarbonyl) allylamine and the like are exemplified as those in which X has a group represented by —CH 2 NHCOOR 6 .
本発明における高分子化合物（Ａ）は、一般式（１）で表される単量体（ａ）に加え、更に一般式（２）で表される単量体（ｂ１）及び／又は一般式（３）で表される単量体（ｂ２）からなる単量体（ｂ）と、一般式（４）で表される単量体（ｃ）を構成単位とすることにより、柔軟性付与効果が向上するため好ましい。 In addition to the monomer (a) represented by the general formula (1), the polymer compound (A) in the present invention is further represented by the monomer (b1) and / or the general formula represented by the general formula (2). By providing the monomer (b) composed of the monomer (b2) represented by (3) and the monomer (c) represented by the general formula (4) as structural units, a flexibility imparting effect Is preferable.
一般式（２）におけるＲ７は、水素原子又はメチル基である。
一般式（２）におけるＹ１は、−ＣＯＯＲ１０−又は−ＣＯＮ（Ｒ１１）Ｒ１２−で表される基であり、Ｒ１０及びＲ１２は、それぞれ独立に炭素数２又は３のアルキレン基、Ｒ１１は水素原子又は炭素数１〜３のアルキル基である。Ｙ１のうち、柔軟性付与効果の観点から好ましいのは−ＣＯＮ（Ｒ１１）Ｒ１２−で表される基である。
炭素数２又は３のアルキレン基としては、エチレン基、エチリデン基、トリメチレン基、プロピレン基、プロピリデン基及びイソプロピリデン基等が挙げられる。
炭素数１〜３のアルキル基としては、メチル基、エチル基、ｎ−プロピル基及びイソプロピル基が挙げられる。
Ｒ１０及びＲ１２のうち、柔軟性付与効果の観点から好ましいのは、プロピレン基である。
Ｒ１１のうち、柔軟性付与効果の観点から好ましいのは水素原子である。
一般式（２）におけるＲ８及びＲ９は、それぞれ独立に水素原子、炭素数１〜４のアルキル基又は炭素数１〜３のヒドロキシアルキル基である。
炭素数１〜４のアルキル基及び炭素数１〜３のヒドロキシアルキル基としては、一般式（１）におけるＲ２及びＲ３として例示したものと同様のものが挙げられる。
Ｒ８及びＲ９のうち、柔軟性付与効果の観点から好ましいのはメチル基である。
R 7 in the general formula (2) is a hydrogen atom or a methyl group.
Y 1 in the general formula (2) is a group represented by —COOR 10 — or —CON (R 11 ) R 12 —, and R 10 and R 12 are each independently an alkylene group having 2 or 3 carbon atoms. , R 11 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. Among Y 1 , a group represented by —CON (R 11 ) R 12 — is preferable from the viewpoint of imparting flexibility.
Examples of the alkylene group having 2 or 3 carbon atoms include an ethylene group, an ethylidene group, a trimethylene group, a propylene group, a propylidene group, and an isopropylidene group.
Examples of the alkyl group having 1 to 3 carbon atoms include a methyl group, an ethyl group, an n-propyl group, and an isopropyl group.
Of R 10 and R 12 , a propylene group is preferable from the viewpoint of imparting flexibility.
Of R 11, a hydrogen atom is preferable from the viewpoint of imparting flexibility.
R 8 and R 9 in the general formula (2) are each independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a hydroxyalkyl group having 1 to 3 carbon atoms.
Examples of the alkyl group having 1 to 4 carbon atoms and the hydroxyalkyl group having 1 to 3 carbon atoms are the same as those exemplified as R 2 and R 3 in the general formula (1).
Of R 8 and R 9, a methyl group is preferable from the viewpoint of imparting flexibility.
一般式（２）で表される単量体（ｂ１）のうち、Ｙ１が−ＣＯＯ−Ｒ１０−で表される基を有するものとしては、アクリル酸−Ｎ，Ｎ−ジメチルアミノエチル、アクリル酸−Ｎ，Ｎ−ジメチルアミノメチル、アクリル酸−Ｎ，Ｎ−ジメチルアミノブチル、アクリル酸−Ｎ，Ｎ−ジメチルアミノプロピル、メタクリル酸−Ｎ，Ｎ−ジメチルアミノエチル、メタクリル酸−Ｎ，Ｎ−ジメチルアミノメチル、メタクリル酸−Ｎ，Ｎ−ジメチルアミノブチル、メタクリル酸−Ｎ，Ｎ−ジメチルアミノプロピル、アクリル酸−Ｎ，Ｎ−ジエチルアミノエチル、アクリル酸−Ｎ，Ｎ−ジエチルアミノメチル、アクリル酸−Ｎ，Ｎ−ジエチルアミノブチル、アクリル酸−Ｎ，Ｎ−ジエチルアミノプロピル、メタクリル酸−Ｎ，Ｎ−ジエチルアミノエチル、メタクリル酸−Ｎ，Ｎ−ジエチルアミノメチル、メタクリル酸−Ｎ，Ｎ−ジエチルアミノブチル及びメタクリル酸−Ｎ，Ｎ−ジエチルアミノプロピル等が挙げられる。 Among the monomers (b1) represented by the general formula (2), Y 1 having a group represented by —COO—R 10 — includes acrylic acid-N, N-dimethylaminoethyl, acrylic Acid-N, N-dimethylaminomethyl, acrylic acid-N, N-dimethylaminobutyl, acrylic acid-N, N-dimethylaminopropyl, methacrylic acid-N, N-dimethylaminoethyl, methacrylic acid-N, N- Dimethylaminomethyl, methacrylate-N, N-dimethylaminobutyl, methacrylate-N, N-dimethylaminopropyl, acrylic acid-N, N-diethylaminoethyl, acrylic acid-N, N-diethylaminomethyl, acrylic acid-N , N-diethylaminobutyl, acrylic acid-N, N-diethylaminopropyl, methacrylic acid-N, N-diethylaminoethyl, Methacrylic acid -N, N- diethylaminomethyl, -N methacrylate, N- diethylamino-butyl and methacrylic acid -N, N- diethylaminopropyl and the like.
一般式（２）で表される単量体（ｂ１）のうち、Ｙ１が−ＣＯＮ（Ｒ１１）Ｒ１２−で表される基を有するものとしては、Ｎ，Ｎ−ジメチルアミノプロピルアクリルアミド、Ｎ，Ｎ−ジメチルアミノプロピルメタクリルアミド、Ｎ，Ｎ−ジメチルアミノメチルアクリルアミド、Ｎ，Ｎ−ジメチルアミノメチルメタクリルアミド、Ｎ，Ｎ−ジメチルアミノエチルアクリルアミド、Ｎ，Ｎ−ジメチルアミノエチルメタクリルアミド、Ｎ，Ｎ−ジメチルアミノブチルアクリルアミド及びＮ，Ｎ−ジメチルアミノブチルメタクリルアミド等が挙げられる。 Among the monomers (b1) represented by the general formula (2), Y 1 having a group represented by —CON (R 11 ) R 12 — includes N, N-dimethylaminopropylacrylamide, N, N-dimethylaminopropyl methacrylamide, N, N-dimethylaminomethyl acrylamide, N, N-dimethylaminomethyl methacrylamide, N, N-dimethylaminoethyl acrylamide, N, N-dimethylaminoethyl methacrylamide, N, N-dimethylaminobutyl acrylamide, N, N-dimethylaminobutyl methacrylamide, etc. are mentioned.
単量体（ｂ１）は酸で中和してもよく、中和に用いる酸としては、硫酸、塩酸、酢酸、乳酸、プロピオン酸、ｐ−トルエンスルホン酸及びクエン酸等が挙げられる。 The monomer (b1) may be neutralized with an acid, and examples of the acid used for neutralization include sulfuric acid, hydrochloric acid, acetic acid, lactic acid, propionic acid, p-toluenesulfonic acid, and citric acid.
一般式（３）におけるＲ１３は、水素原子又はメチル基である。
一般式（３）におけるＹ２は、−ＣＯＯＲ１７−又は−ＣＯＮ（Ｒ１８）Ｒ１９−で表される基であり、Ｒ１７及びＲ１９は、それぞれ独立に炭素数２又は３のアルキレン基、Ｒ１８は水素原子又は炭素数１〜３のアルキル基である。
炭素数２又は３のアルキレン基としては、一般式（２）におけるＲ１０及びＲ１２として例示したものと同様のものが挙げられる。
炭素数１〜３のアルキル基としては、一般式（２）におけるＲ１１として例示したものと同様のものが挙げられる。
一般式（３）におけるＲ１４、Ｒ１５及びＲ１６は、それぞれ独立に炭素数１〜４のアルキル基又は炭素数１〜３のヒドロキシアルキル基である。
炭素数１〜４のアルキル基及び炭素数１〜３のヒドロキシアルキル基としては、一般式（１）におけるＲ２及びＲ３として例示したものと同様のものが挙げられる。
Ｒ１７及びＲ１９のうち、柔軟性付与効果の観点から好ましいのは、エチレン基及びプロピレン基である。
Ｒ１８のうち、柔軟性付与効果の観点から好ましいのは水素原子である。
Ｒ１４、Ｒ１５及びＲ１６のうち、柔軟性付与効果の観点から好ましいのはメチル基である。
R 13 in the general formula (3) is a hydrogen atom or a methyl group.
Y 2 in the general formula (3) is a group represented by —COOR 17 — or —CON (R 18 ) R 19 —, and R 17 and R 19 are each independently an alkylene group having 2 or 3 carbon atoms. , R 18 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
Examples of the alkylene group having 2 or 3 carbon atoms include the same groups as those exemplified as R 10 and R 12 in the general formula (2).
The alkyl group having 1 to 3 carbon atoms include the same as those exemplified as R 11 in the general formula (2).
R 14 , R 15 and R 16 in the general formula (3) are each independently an alkyl group having 1 to 4 carbon atoms or a hydroxyalkyl group having 1 to 3 carbon atoms.
Examples of the alkyl group having 1 to 4 carbon atoms and the hydroxyalkyl group having 1 to 3 carbon atoms are the same as those exemplified as R 2 and R 3 in the general formula (1).
Of R 17 and R 19 , an ethylene group and a propylene group are preferable from the viewpoint of imparting flexibility.
Of R 18, a hydrogen atom is preferable from the viewpoint of imparting flexibility.
Of R 14 , R 15 and R 16, a methyl group is preferable from the viewpoint of flexibility imparting effect.
一般式（３）におけるｎは１〜３の整数であり、Ｘｎ−はｎ価のハロゲンイオン又はアニオン性基である。
ｎ価のハロゲンイオンとしては、フッ素イオン、塩素イオン、臭素イオン及びヨウ素イオン等が挙げられる。
ｎ価のアニオン性基としては、ｎ価の無機酸又は有機酸から構成されるアニオン性基が挙げられる。
ｎ価の無機酸としては、塩酸、臭化水素酸、ヨウ化水素酸、硫酸及びリン酸等が挙げられる。
ｎ価の有機酸のうち、１価の有機酸としては、炭素数１〜２２のモノカルボン酸（酢酸、プロピオン酸、酪酸、２−エチルヘキサン酸、ノナン酸、ドデカン酸、テトラデカン酸、ステアリン酸、オレイン酸、安息香酸、エチル安息香酸、桂皮酸及びｔ−ブチル安息香酸等）及びアミノ酸（グリシン、アラニン、バリン、ロイシン、イソロイシン、フェニルアラニン、チロシン、セリン、スレオニン、グルタミン、アスパラギン、システイン及びメチオニン等）等が挙げられる。
２又は３価の有機酸としては、アルキル（炭素数１〜４）硫酸、シュウ酸、マロン酸、コハク酸、アジピン酸、クエン酸、リンゴ酸、酒石酸、グルタミン酸、アスパラギン酸、ヒドロキシエチルイミノ二酢酸、グルタミン酸二酢酸、アスパラギン酸二酢酸、エチレンジアミン四酢酸、フタル酸、イソフタル酸、テレフタル酸及びトリメリット酸等が挙げられる。
Ｘｎ−のうち、柔軟性付与効果の観点から好ましいのはハロゲンイオンであり、更に好ましいのは塩素イオンである。
In the general formula (3), n is an integer of 1 to 3, and X n− is an n-valent halogen ion or anionic group.
Examples of the n-valent halogen ion include fluorine ion, chlorine ion, bromine ion and iodine ion.
Examples of the n-valent anionic group include an anionic group composed of an n-valent inorganic acid or organic acid.
Examples of the n-valent inorganic acid include hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, and phosphoric acid.
Among the n-valent organic acids, monovalent organic acids include monocarboxylic acids having 1 to 22 carbon atoms (acetic acid, propionic acid, butyric acid, 2-ethylhexanoic acid, nonanoic acid, dodecanoic acid, tetradecanoic acid, stearic acid. Oleic acid, benzoic acid, ethyl benzoic acid, cinnamic acid and t-butyl benzoic acid) and amino acids (glycine, alanine, valine, leucine, isoleucine, phenylalanine, tyrosine, serine, threonine, glutamine, asparagine, cysteine, methionine, etc. ) And the like.
Examples of the divalent or trivalent organic acid include alkyl (C1-4) sulfuric acid, oxalic acid, malonic acid, succinic acid, adipic acid, citric acid, malic acid, tartaric acid, glutamic acid, aspartic acid, and hydroxyethyliminodiacetic acid. Glutamic acid diacetic acid, aspartic acid diacetic acid, ethylenediaminetetraacetic acid, phthalic acid, isophthalic acid, terephthalic acid and trimellitic acid.
Among X n− , halogen ions are preferable from the viewpoint of imparting flexibility, and chlorine ions are more preferable.
一般式（３）で表される単量体（ｂ２）のうち、Ｙ２が−ＣＯＯＲ１７−で表される基を有するものとしては、Ｎ，Ｎ，Ｎ−トリメチル−Ｎ−（２−アクリロイルオキシエチル）アンモニウムクロライド、及びＮ，Ｎ，Ｎ−トリメチル−Ｎ−（２−メタクリロイルオキシエチル）アンモニウムクロライド等が挙げられる。
一般式（３）で表される単量体（ｂ２）のうち、Ｙ２が−ＣＯＮ（Ｒ１８）Ｒ１９−で表される基を有するものとしては、Ｎ，Ｎ，Ｎ−トリメチル−Ｎ−（２−アクリロイルアミノプロピル）アンモニウムクロライド、Ｎ，Ｎ，Ｎ−トリメチル−Ｎ−（２−メタクリロイルアミノプロピル）アンモニウムクロライド、Ｎ，Ｎ−ジメチル−Ｎ−エチル−Ｎ−（２−アクリロイルアミノエチル）アンモニウムエチルサルフェート、Ｎ，Ｎ，Ｎ−トリメチル−Ｎ−（２−メタクリロイルアミノプロピル）アンモニウムメチルサルフェート等が挙げられる。
Among monomers (b2) represented by the general formula (3), Y 2 having a group represented by —COOR 17 — includes N, N, N-trimethyl-N- (2-acryloyl). And oxyethyl) ammonium chloride and N, N, N-trimethyl-N- (2-methacryloyloxyethyl) ammonium chloride.
Among the monomers (b2) represented by the general formula (3), Y 2 having a group represented by —CON (R 18 ) R 19 — includes N, N, N-trimethyl-N. -(2-acryloylaminopropyl) ammonium chloride, N, N, N-trimethyl-N- (2-methacryloylaminopropyl) ammonium chloride, N, N-dimethyl-N-ethyl-N- (2-acryloylaminoethyl) Examples include ammonium ethyl sulfate, N, N, N-trimethyl-N- (2-methacryloylaminopropyl) ammonium methyl sulfate, and the like.
一般式（４）におけるＲ２０は、水素原子又はメチル基である。
一般式（４）におけるＺは、−Ｏ−ＣＯ−Ｒ２１、−ＣＯＯ−Ｒ２２又は−ＣＯＮ（Ｒ２３）Ｒ２４で表される基であり、Ｒ２１、Ｒ２２及びＲ２４は、それぞれ独立に炭素数８〜２４の直鎖又は分岐鎖アルキル基、Ｒ２３は水素原子又は炭素数１〜３のアルキル基である。
炭素数８〜２４の直鎖又は分岐鎖アルキル基としては、ｎ−オクチル基、イソオクチル基、２−エチルヘキシル基、ｎ−ノニル基、イソノニル基、ｎ−デシル基、イソデシル基、ｎ−ドデシル基、イソドデシル基、ｎ−トリデシル基、イソトリデシル基、ｎ−テトラデシル基、イソ−テトラデシル基、ｎ−ヘキサデシル基、イソヘキサデシル基、ｎ−ステアリル基、イソステアリル基、ｎ−ノナデシル基、ｎ−エイコシル基及びｎ−テトラコシル基等が挙げられる。これらのうち、柔軟性付与効果の観点から好ましいのは、炭素数が１６〜２４のアルキル基である。
炭素数１〜３のアルキル基としては、一般式（２）におけるＲ１０及びＲ１２として例示したものと同様のものが挙げられる。
R 20 in the general formula (4) is a hydrogen atom or a methyl group.
Z in the general formula (4), -O-CO- R 21, -COO-R 22 or -CON (R 23) a group represented by R 24, R 21, R 22 and R 24 are each Independently, a linear or branched alkyl group having 8 to 24 carbon atoms, R 23 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
As the linear or branched alkyl group having 8 to 24 carbon atoms, n-octyl group, isooctyl group, 2-ethylhexyl group, n-nonyl group, isononyl group, n-decyl group, isodecyl group, n-dodecyl group, Isododecyl group, n-tridecyl group, isotridecyl group, n-tetradecyl group, iso-tetradecyl group, n-hexadecyl group, isohexadecyl group, n-stearyl group, isostearyl group, n-nonadecyl group, n-eicosyl group and Examples include an n-tetracosyl group. Of these, alkyl groups having 16 to 24 carbon atoms are preferred from the viewpoint of imparting flexibility.
The alkyl group having 1 to 3 carbon atoms include the same as those exemplified as R 10 and R 12 in the general formula (2).
一般式（４）で表される単量体（ｃ）のうち、Ｚが−Ｏ−ＣＯ−Ｒ２１で表される基を有するものとしては、デカン酸ビニル、デカン酸イソプロペニル、テトラデカン酸ビニル、テトラデカン酸イソプロペニル、ステアリン酸ビニル、ステアリン酸イソプロペニル、テトラコサン酸ビニル及びテトラコサン酸イソプロペニル等が挙げられる。
一般式（４）で表される単量体（ｃ）のうち、Ｚが−ＣＯＯ−Ｒ２２で表される基を有するものとしては、アクリル酸ｎ−オクチル、メタクリル酸ｎ−ドデシル、アクリル酸ｎ−ドデシル、アクリル酸イソヘキサデシル、メタクリル酸ｎ−ステアリル基及びアクリル酸ｎ−テトラコシル基等が挙げられる。
一般式（４）で表される単量体（ｃ）のうち、Ｚが−ＣＯＮ（Ｒ２３）Ｒ２４で表される基を有するものとしては、Ｎ−ｎ−オクチルアクリルアミド、Ｎ−ｎ−テトラデシルメタクリルアミド、Ｎ−メチル−Ｎ−テトラデシルアクリルアミド、Ｎ−メチル−Ｎ−イソヘキサデシルアクリルアミド等が挙げられる。
Among the monomers (c) represented by the general formula (4), those in which Z has a group represented by —O—CO—R 21 include vinyl decanoate, isopropenyl decanoate, and vinyl tetradecanoate. , Isopropenyl tetradecanoate, vinyl stearate, isopropenyl stearate, vinyl tetracosanoate and isopropenyl tetracosanoate.
Among the monomers (c) represented by the general formula (4), those in which Z has a group represented by —COO—R 22 include n-octyl acrylate, n-dodecyl methacrylate, and acrylic acid. Examples thereof include n-dodecyl, isohexadecyl acrylate, n-stearyl methacrylate, and n-tetracosyl acrylate.
Among the monomers (c) represented by the general formula (4), those in which Z has a group represented by —CON (R 23 ) R 24 include Nn-octylacrylamide, Nn— Examples include tetradecyl methacrylamide, N-methyl-N-tetradecyl acrylamide, N-methyl-N-isohexadecyl acrylamide, and the like.
高分子化合物（Ａ）は、単量体（ａ）、（ｂ）及び（ｃ）以外に、ビニル基を有する単量体（ｄ）を構成単位としてもよい。単量体（ｄ）としては、アクリル酸、メタクリル酸、アクリル酸メチル、メタクリル酸メチル、アクリル酸ブチル、ポリオキシアルキレンアクリル酸モノエステル、ビニルアルコール、酢酸ビニル、アリルアルコール、ポリオキシアルキレンアリルエーテル、スチレン、スチレンスルホン酸及びスチレンスルホン酸塩等が挙げられる。 In addition to the monomers (a), (b), and (c), the polymer compound (A) may include a monomer (d) having a vinyl group as a structural unit. As the monomer (d), acrylic acid, methacrylic acid, methyl acrylate, methyl methacrylate, butyl acrylate, polyoxyalkylene acrylic acid monoester, vinyl alcohol, vinyl acetate, allyl alcohol, polyoxyalkylene allyl ether, Examples thereof include styrene, styrene sulfonic acid, and styrene sulfonate.
高分子化合物（Ａ）は、柔軟性付与効果の観点から、（Ａ）の重量に基づき単量体（ａ）が１〜４０重量％、（ｂ）が１〜３０重量％及び（ｃ）が５０〜９０重量％の比率で構成されているものが好ましく、更に好ましくは、（ａ）が５〜３０重量％、（ｂ）が５〜２５重量％及び（ｃ）が６０〜８５重量％の比率で構成されているものである。 From the viewpoint of imparting flexibility, the polymer compound (A) is based on the weight of (A), the monomer (a) is 1 to 40% by weight, (b) is 1 to 30% by weight, and (c) is What is comprised by the ratio of 50 to 90 weight% is preferable, More preferably, (a) is 5 to 30 weight%, (b) is 5 to 25 weight%, and (c) is 60 to 85 weight%. It is composed of ratios.
高分子化合物（Ａ）の重量平均分子量は、柔軟性付与効果の観点から好ましくは１，０００〜１００，０００であり、更に好ましくは２，０００〜５０，０００、特に好ましくは３，０００〜３０，０００である。
高分子化合物（Ａ）の重量平均分子量は、ゲルパーミエーションクロマトグラフィーを用いて、以下の条件で測定することができる。
装置：「ＨＬＣ−８１２０ＧＰＣ」［東ソー（株）製］
カラム：「Ｇｕａｒｄｃｏｌｕｍｎ ＨＸＬ−Ｈ」（１本）
「ＴＳＫｇｅｌ ＧＭＨＸＬ」（２本）［いずれも東ソー（株）製］
試料溶液：０．２５重量％のＴＨＦ溶液
溶液注入量：１００μｌ
流量：１ｍｌ／分
測定温度：４０℃
検出装置：屈折率検出器
基準物質：標準ポリスチレン（ＴＳＫｓｔａｎｄａｒｄ ＰＯＬＹＳＴＹＲＥＮＥ）［東ソー（株）製］
The weight average molecular weight of the polymer compound (A) is preferably 1,000 to 100,000, more preferably 2,000 to 50,000, particularly preferably 3,000 to 30 from the viewpoint of imparting flexibility. , 000.
The weight average molecular weight of the polymer compound (A) can be measured under the following conditions using gel permeation chromatography.
Apparatus: “HLC-8120GPC” [manufactured by Tosoh Corporation]
Column: “Guardcolumn H XL- H” (1)
"TSKgel GMH XL " (2) [both manufactured by Tosoh Corporation]
Sample solution: 0.25 wt% THF solution Injection volume: 100 μl
Flow rate: 1 ml / min Measurement temperature: 40 ° C
Detector: Refractive index detector Reference material: Standard polystyrene (TSK standard POLYSTYRENE) [manufactured by Tosoh Corporation]
高分子化合物（Ａ）は、単量体（ａ）と、必要により単量体（ｂ）、（ｃ）、（ｄ）とを、触媒の存在下、熱ラジカル重合、光ラジカル重合及びアニオン重合等の公知の方法で重合して得ることができる。重合温度は、好ましくは０〜２００℃であり、重合反応は常圧下又は加圧下で行うことができる。
重合反応時には有機溶媒（酢酸エチル、トルエン、キシレン、ヘキサン、ヘプタン、オクタン、ジエチルエーテル、ジ−ｎ−プロピルエーテル、エチル−ｎ−プロピルエーテル及びケトン系溶媒等）、水又は有機溶媒と水との混合溶媒を使用し、反応終了後に減圧留去してもよい。
触媒としては、熱ラジカル重合の場合はアゾ系化合物（アゾビスイソブチロニトリル等）及び過酸化物（ｔ−ブチルパーオキシベンゾエート等）等が挙げられる。光ラジカル重合の場合は、光ラジカル開始剤（ベンゾインアルキルエーテル等）及び増感剤（アントラキノン等）を併用したものが挙げられる。アニオン重合の場合は、チーグラーナッタ系触媒及びメタロセン系触媒等を併用したものが挙げられる。触媒の使用量は、単量体の全重量に基づき、好ましくは０．０５〜５重量％である。
The polymer compound (A) comprises monomer (a) and, if necessary, monomers (b), (c) and (d) in the presence of a catalyst, thermal radical polymerization, photo radical polymerization and anion polymerization. It can be obtained by polymerization by a known method such as The polymerization temperature is preferably 0 to 200 ° C., and the polymerization reaction can be performed under normal pressure or under pressure.
At the time of the polymerization reaction, an organic solvent (such as ethyl acetate, toluene, xylene, hexane, heptane, octane, diethyl ether, di-n-propyl ether, ethyl-n-propyl ether and a ketone solvent), water or an organic solvent and water A mixed solvent may be used and distilled off under reduced pressure after completion of the reaction.
Examples of the catalyst include azo compounds (such as azobisisobutyronitrile) and peroxides (such as t-butylperoxybenzoate) in the case of thermal radical polymerization. In the case of photoradical polymerization, a combination of a photoradical initiator (such as benzoin alkyl ether) and a sensitizer (such as anthraquinone) may be used. In the case of anionic polymerization, a combination of a Ziegler-Natta catalyst and a metallocene catalyst may be used. The amount of the catalyst used is preferably 0.05 to 5% by weight based on the total weight of the monomers.
本発明の柔軟剤組成物は、必要に応じて、カチオン性界面活性剤（Ｂ）を含有してもよい。（Ｂ）としては、エステル基、アミド基及び／又はエーテル基を有していてもよい総炭素数８〜３０の長鎖アルキル基若しくはアルケニル基を、１個若しくは２個有する３級アミン又はその塩、あるいは前記３級アミンの４級化物が挙げられる。具体的にはＮ，Ｎ−ジアルキル−Ｎ，Ｎ−ジメチルアンモニウムクロライド（総炭素数１２〜２４）、Ｎ−ヒドロキシメエチル−Ｎ−メチル−Ｎ，Ｎ−ビス（アルキロイロキシエチル）アンモニウムメチルサルフェート（総炭素数１２〜２４）、Ｎ−アルキロイロキシエチル−Ｎ−アルキロイルアミノプロピルアミンの塩酸酸、及び１−アルキロイロキシエチル−１−メチル−２−アルキル−１，３−イミダゾリニウムメチルサルフェート（総炭素数１２〜２４）等が挙げられる。 The softening agent composition of this invention may contain a cationic surfactant (B) as needed. (B) is a tertiary amine having one or two long-chain alkyl or alkenyl groups having a total carbon number of 8 to 30 which may have an ester group, an amide group and / or an ether group, or Examples thereof include salts and quaternized products of the tertiary amines. Specifically, N, N-dialkyl-N, N-dimethylammonium chloride (total carbon number 12-24), N-hydroxymethyl-N-methyl-N, N-bis (alkyloxyoxyethyl) ammonium methyl sulfate (Total carbon number 12-24), hydrochloric acid of N-alkylyloxyethyl-N-alkylylaminopropylamine, and 1-alkylyloxyethyl-1-methyl-2-alkyl-1,3-imidazolinium Methyl sulfate (total carbon number 12-24) etc. are mentioned.
本発明の柔軟剤組成物は、必要に応じて、非イオン性界面活性剤（Ｃ）、親水性溶剤（Ｄ）及び水溶性無機塩（Ｅ）からなる群から選ばれる１種以上を含有してもよい。 The softener composition of the present invention contains at least one selected from the group consisting of a nonionic surfactant (C), a hydrophilic solvent (D), and a water-soluble inorganic salt (E) as necessary. May be.
非イオン性界面活性剤（Ｃ）としては、アルキレンオキサイド付加型非イオン性界面活性剤（Ｃ１）及び多価アルコール型非イオン性界面活性剤（Ｃ２）等が挙げられる。
アルキレンオキサイド付加型非イオン性界面活性剤（Ｃ１）としては、高級アルコール（炭素数８〜１８）アルキレン（炭素数２〜４、好ましいのは２）オキサイド付加物（活性水素１個当たりの付加モル数１〜８０）、高級アミン（炭素数８〜１８）アルキレン（炭素数２〜４、好ましいのは２）オキサイド付加物（活性水素１個当たりの付加モル数１〜８０）、アルキル（炭素数１〜１２）フェノールエチレンオキサイド付加物（付加モル数１〜８０）、脂肪酸（炭素数８〜１８）エチレンオキサイド付加物（活性水素１個当たりの付加モル数１〜８０）、ポリプロピレングリコール（数平均分子量２００〜４，０００）エチレンオキサイド付加物（活性水素１個当たりの付加モル数１〜５０）及びポリオキシエチレン（繰り返し単位数３〜３０）アルキル（炭素数６〜２０）アリルエーテル等が挙げられる。
多価アルコール型非イオン性界面活性剤（Ｃ２）としては、グリセリンモノステアレート、グリセリンモノオレート、ソルビタンモノラウレート及びソルビタンモノオレート等の多価（２〜８価又はそれ以上）アルコール（炭素数２〜３０）の脂肪酸（炭素数８〜２４）エステル、ラウリン酸モノエタノールアミド及びラウリン酸ジエタノールアミド等の脂肪酸（炭素数１０〜１８）アルカノールアミド等が挙げられる。
非イオン性界面活性剤（Ｃ）のうち、柔軟剤組成物の貯蔵安定性の観点から好ましいのは、アルキレンオキサイド付加型非イオン性界面活性剤であり、更に好ましいのは高級アルコール（炭素数８〜１８）アルキレン（炭素数２〜４、好ましいのは２）オキサイド付加物（活性水素１個当たりの付加モル数１〜８０）、高級アミン（炭素数８〜１８）アルキレン（炭素数２〜４、好ましいのは２）オキサイド付加物（活性水素１個当たりの付加モル数１〜８０）である。
なお、非イオン性界面活性剤（Ｃ）は、単独で用いても２種以上を併用してもよい。
Examples of the nonionic surfactant (C) include an alkylene oxide addition type nonionic surfactant (C1) and a polyhydric alcohol type nonionic surfactant (C2).
Examples of the alkylene oxide addition type nonionic surfactant (C1) include higher alcohols (8 to 18 carbon atoms) alkylene (2 to 4 carbon atoms, preferably 2) oxide adducts (addition moles per active hydrogen). 1 to 80), higher amine (8 to 18 carbon atoms) alkylene (2 to 4 carbon atoms, preferably 2), oxide adduct (1 to 80 moles added per active hydrogen), alkyl (carbon number) 1-12) phenol ethylene oxide adduct (addition mole number 1-80), fatty acid (carbon number 8-18) ethylene oxide adduct (addition mole number 1-80 per active hydrogen), polypropylene glycol (number average) Molecular weight 200 to 4,000) ethylene oxide adduct (1 to 50 moles added per active hydrogen) and polyoxyethylene (number of repeating units) 30) alkyl (number 6-20) allyl ether such as carbon and the like.
Examples of the polyhydric alcohol type nonionic surfactant (C2) include polyvalent (2 to 8 or more) alcohols (carbon number) such as glycerol monostearate, glycerol monooleate, sorbitan monolaurate and sorbitan monooleate. 2-30) fatty acid (carbon number 8-24) ester, fatty acid (carbon number 10-18) alkanolamide, such as lauric acid monoethanolamide and lauric acid diethanolamide.
Of the nonionic surfactants (C), alkylene oxide addition type nonionic surfactants are preferred from the viewpoint of the storage stability of the softener composition, and higher alcohols (8 carbon atoms) are more preferred. -18) alkylene (2 to 4 carbon atoms, preferably 2) oxide adduct (1 to 80 moles added per active hydrogen), higher amine (8 to 18 carbon atoms) alkylene (2 to 4 carbon atoms) 2) Oxide adduct (1 to 80 moles added per active hydrogen) is preferable.
In addition, a nonionic surfactant (C) may be used independently or may use 2 or more types together.
親水性溶剤（Ｄ）としては、炭素数１〜４のアルコール及びグリコール系溶剤が挙げられる。
炭素数１〜４のアルコールとしては、メチルアルコール、エチルアルコール、ｎ−プロピルアルコール、イソプロピルアルコール、ｎ−ブチルアルコール及びｔ−ブチルアルコール等が挙げられる。
グリコール系溶剤としては、グリコール類（エチレングリコール、ジエチレングリコール、トリエチレングリコール、プロピレングリコール、ジプロピレングリコール、１，２−ブチレングリコール及び１，３−ブチレングリコール等）、グリコール類のモノアルキルエーテル（エチレングリコールモノブチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノブチルエーテル、ジエチレングリコールモノヘキシルエーテル及びジプロピレングリコールモノメチルエーテル等）及びグリコール類のジアルキルエーテル（エチレングリコールジメチルエーテル、ジエチレングリコールジメチルエーテル、トリエチレングリコールジメチルエーテル、ジエチレングリコールジエチルエーテル及びジエチレングリコールイソプロピルメチルエーテル等｝が挙げられる。
親水性溶剤（Ｄ）のうち、柔軟剤組成物の貯蔵安定性の観点から好ましいのは、エチルアルコール、イソプロピルアルコール、エチレングリコール、ジエチレングリコール、プロピレングリコール、ジプロピレングリコールであり、更に好ましいのは、エチルアルコール及びプロピレングリコールである。
なお、親水性溶剤（Ｄ）は、単独で用いても２種以上を併用してもよく、２種以上を併用する場合の比率は特に限定されない。
Examples of the hydrophilic solvent (D) include alcohols having 1 to 4 carbon atoms and glycol solvents.
Examples of the alcohol having 1 to 4 carbon atoms include methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, and t-butyl alcohol.
Glycol solvents include glycols (ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, 1,2-butylene glycol, 1,3-butylene glycol, etc.), monoalkyl ethers of glycols (ethylene glycol) Monobutyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol monohexyl ether and dipropylene glycol monomethyl ether) and glycol dialkyl ethers (ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol diethyl ether and diethylene glycol) Isopropyl methyl ether} and the like.
Among the hydrophilic solvents (D), ethyl alcohol, isopropyl alcohol, ethylene glycol, diethylene glycol, propylene glycol, and dipropylene glycol are preferable from the viewpoint of the storage stability of the softener composition, and ethyl is more preferable. Alcohol and propylene glycol.
In addition, a hydrophilic solvent (D) may be used independently or may use 2 or more types together, and the ratio in the case of using 2 or more types together is not specifically limited.
水溶性無機塩（Ｅ）としては、２５℃の水１００ｇに対して１０ｇ以上溶解する無機塩が挙げられ、例えばアルカリ金属塩［ハロゲン化物（塩化ナトリウム、塩化カリウム、臭化ナトリウム及びフッ化ナトリウム等）、硫酸塩（硫酸ナトリウム及び硫酸カリウム等）及びリン酸塩（リン酸ナトリウム及びリン酸カリウム等）］、アルカリ土類金属塩［ハロゲン化物（塩化カルシウム及び塩化マグネシウム等）及び硫酸塩（硫酸マグネシウム等）］及びアンモニウム塩［ハロゲン化物（塩化アンモニウム等）及び硫酸塩（硫酸アンモニウム等）］が挙げられる。
水溶性無機塩（Ｅ）のうち、柔軟剤組成物の貯蔵安定性の観点から好ましいのは、塩化ナトリウム、硫酸ナトリウム及び塩化カルシウムである。
なお、水溶性無機塩（Ｅ）は、単独で用いても２種以上を併用してもよい。
Examples of the water-soluble inorganic salt (E) include inorganic salts that dissolve 10 g or more in 100 g of water at 25 ° C., for example, alkali metal salts [halides (sodium chloride, potassium chloride, sodium bromide, sodium fluoride, etc.) ), Sulfates (such as sodium sulfate and potassium sulfate) and phosphates (such as sodium phosphate and potassium phosphate)], alkaline earth metal salts [halides (such as calcium chloride and magnesium chloride) and sulfates (magnesium sulfate) Etc.)] and ammonium salts [halides (such as ammonium chloride) and sulfates (such as ammonium sulfate)].
Among the water-soluble inorganic salts (E), sodium chloride, sodium sulfate and calcium chloride are preferable from the viewpoint of the storage stability of the softener composition.
In addition, a water-soluble inorganic salt (E) may be used independently or may use 2 or more types together.
本発明の柔軟剤組成物は、２０℃で液体状又はペースト状であり、乳化分散体又は均一透明である。 The softener composition of the present invention is liquid or paste at 20 ° C., and is an emulsified dispersion or uniform transparent.
本発明の柔軟剤組成物の製造方法は特に限定されないが、例えば、撹拌装置及び加熱冷却装置を備えた混合槽に、高分子化合物（Ａ）と、必要に応じてカチオン性界面活性剤（Ｂ）、非イオン性界面活性剤（Ｃ）、親水性溶剤（Ｄ）、水溶性無機塩（Ｅ）及び水を投入順序に特に制限なく投入し、１０〜６０℃で均一になるまで撹拌して製造する方法が挙げられる。 Although the manufacturing method of the softening agent composition of this invention is not specifically limited, For example, in a mixing tank provided with the stirring apparatus and the heating / cooling apparatus, a high molecular compound (A) and the cationic surfactant (B) as needed. ), Nonionic surfactant (C), hydrophilic solvent (D), water-soluble inorganic salt (E), and water are added without particular limitation to the order of addition, and stirred at 10 to 60 ° C. until uniform. The method of manufacturing is mentioned.
本発明の柔軟剤組成物は、天然繊維、化合繊繊維及びこれらの混紡交編繊繊維の柔軟性付与に特に有用である。
天然繊維としては、木綿、麻及び羊毛等が挙げられる。化合繊繊維としては、再生セルロース繊維（レーヨン及びアセテート等）及び合成繊維（ポリエステル繊維、ポリアミド繊維、アクリル繊維及びスパンデックス等）等が挙げられる。これらの混紡交編繊維としては、木綿又は麻と他の繊維（羊毛、ポリエステル、ポリアミド及びアクリル等）との混紡交編繊維、羊毛と他の繊維（ポリエステル、ポリアミド及びアクリル等）との混紡交編繊維、ポリエステル繊維と他の繊維（レーヨン、アセテート、ポリアミド、アクリル及びスパンデックス等）との混紡交編繊維、及びポリアミド繊維と他の繊維（レーヨン、アセテート、アクリル及びスパンデックス等）との混紡交編繊維等が挙げられる。
繊維の形態としては、布、不織布、編織物及び衣服等が挙げられる。
The softener composition of the present invention is particularly useful for imparting flexibility to natural fibers, synthetic fiber, and mixed / knitted / knitted fiber.
Examples of natural fibers include cotton, hemp and wool. Examples of the synthetic fiber include regenerated cellulose fiber (such as rayon and acetate) and synthetic fiber (such as polyester fiber, polyamide fiber, acrylic fiber, and spandex). These blended knitted fibers include cotton or linen and other fibers (wool, polyester, polyamide, acrylic, etc.), blended knitted fiber, wool and other fibers (polyester, polyamide, acrylic, etc.) Knitted fibers, blended knitted fibers of polyester fibers and other fibers (rayon, acetate, polyamide, acrylic, spandex, etc.), and blended knitted fibers of polyamide fibers and other fibers (rayon, acetate, acrylic, spandex, etc.) Examples thereof include fibers.
Examples of the fiber form include cloth, non-woven fabric, knitted fabric, and clothing.
本発明の柔軟剤組成物は、通常１ｐｐｍ〜０．５重量％の範囲の濃度（水以外の有効成分）に水で希釈して使用される。 The softener composition of the present invention is usually used after diluting with water to a concentration (active ingredient other than water) in the range of 1 ppm to 0.5% by weight.
本発明の柔軟剤組成物で繊維を処理する際の温度は、処理する繊維の種類によって任意に選択できるが、通常５〜８０℃であり、好ましくは２０〜５０℃である。 Although the temperature at the time of processing a fiber with the softening agent composition of this invention can be arbitrarily selected according to the kind of fiber to process, it is 5-80 degreeC normally, Preferably it is 20-50 degreeC.
以下、実施例により本発明を更に説明するが、本発明はこれに限定されるものではない。なお、以下において、部は重量部、％は重量％を示す。 EXAMPLES Hereinafter, although an Example demonstrates this invention further, this invention is not limited to this. In the following, “part” means “part by weight” and “%” means “% by weight”.
以下に、高分子化合物（Ａ）及び比較の高分子化合物の合成例を示す。
＜合成例１〜１０＞
撹拌装置、加熱冷却装置、温度計、滴下ロート２つ、及び窒素導入管を備えた反応容器に、エタノール１５部を投入し、滴下ロートに表１に示す単量体溶液を投入し、別の滴下ロートに表１に示すラジカル重合開始剤と連鎖移動剤の混合溶液を投入した。反応容器の気相部の窒素置換を行った後、密閉下８０℃で、単量体溶液と、連鎖移動剤及びラジカル重合開始剤混合溶液それぞれを４時間かけて滴下し、同温度で滴下終了から２時間熟成し、濃度７０％の高分子化合物（Ａ−１）〜（Ａ−８）、比較の高分子化合物（Ａ’−１）、（Ａ’−２）を得た。
Below, the synthesis example of a high molecular compound (A) and a comparative high molecular compound is shown.
<Synthesis Examples 1-10>
Into a reaction vessel equipped with a stirrer, a heating / cooling device, a thermometer, two dropping funnels, and a nitrogen introducing tube, 15 parts of ethanol was added, and the monomer solution shown in Table 1 was added to the dropping funnel. A mixed solution of a radical polymerization initiator and a chain transfer agent shown in Table 1 was added to the dropping funnel. After carrying out nitrogen substitution of the gas phase part of the reaction vessel, the monomer solution, the chain transfer agent, and the radical polymerization initiator mixed solution were added dropwise over 4 hours at 80 ° C. in a sealed state, and the addition was completed at the same temperature. The polymer compounds (A-1) to (A-8) and the comparative polymer compounds (A′-1) and (A′-2) having a concentration of 70% were obtained.
＜実施例１〜８、比較例１〜４＞
表２に記載の部数（固形分換算）の柔軟剤組成物の各原料を配合し、柔軟剤組成物（実施例１〜８、比較例１〜４）を作製した。
表１に記載の柔軟剤組成物の各原料は以下の通りである。
（Ｂ−１）：Ｎ−ヒドロキシメチル−Ｎ−メチル−Ｎ，Ｎ−ビス（ステアロイロキシエチル）アンモニウムクロライド「ライオンソフターＥＱ」［ライオン（株）製］
（Ｂ−２）：Ｎ，Ｎ−ジステアリル−Ｎ，Ｎ−ジメチルアンモニウムクロライド「カチオンＤＳ」［三洋化成工業（株）製］
（Ｃ−１）：ポリオキシエチレンアルキルエーテル「ナロアクティーＣＬ−２００」［三洋化成工業（株）製］
<Examples 1-8, Comparative Examples 1-4>
Each raw material of the softener composition of the number of parts (solid content conversion) shown in Table 2 was mix | blended, and the softener composition (Examples 1-8, Comparative Examples 1-4) was produced.
Each raw material of the softening agent composition described in Table 1 is as follows.
(B-1): N-hydroxymethyl-N-methyl-N, N-bis (stearoyloxyethyl) ammonium chloride “Lion Softer EQ” [manufactured by Lion Corporation]
(B-2): N, N-distearyl-N, N-dimethylammonium chloride “cation DS” [manufactured by Sanyo Chemical Industries, Ltd.]
(C-1): Polyoxyethylene alkyl ether “Naroacty CL-200” [manufactured by Sanyo Chemical Industries, Ltd.]
実施例１〜８、比較例１〜４の柔軟剤組成物について、繊維に対する柔軟性付与効果を以下の方法で評価した。 About the softening agent composition of Examples 1-8 and Comparative Examples 1-4, the softness | flexibility provision effect with respect to a fiber was evaluated with the following method.
＜柔軟性付与効果の評価方法＞
実施例１〜８、比較例１〜４の柔軟剤組成物を、有効成分が５０ｐｐｍになるように水で希釈し、試験液１，５００部を作製した。試験液に市販の綿タオル（綿１００％）を５分間浸漬した（浴比１：２０）。次いで、遠心脱水機で絞り（絞り率１００％）、更に風乾して試料とした。
各試料の柔軟性を、比較例３を基準試料として５人のパネラーによる触感で下記の基準で判定し、平均点を算出した。数値が大きいほど柔軟性付与効果に優れることを表す。結果を表２に示す。
［判定基準］
５点：基準試料（比較例３）より柔軟性が良好
４点：基準試料（比較例３）より柔軟性がやや良好
３点：基準試料（比較例３）と柔軟性が同等
２点：基準試料（比較例３）より柔軟性がやや不良
１点：基準試料（比較例３）より柔軟性が不良
<Evaluation method of flexibility imparting effect>
The softening agent compositions of Examples 1 to 8 and Comparative Examples 1 to 4 were diluted with water so that the active ingredient was 50 ppm, and 1,500 parts of test solutions were prepared. A commercially available cotton towel (100% cotton) was immersed in the test solution for 5 minutes (bath ratio 1:20). Subsequently, it was squeezed with a centrifugal dehydrator (squeezing rate 100%) and further air-dried to prepare a sample.
The flexibility of each sample was determined based on the following criteria based on the tactile sensation of five panelists using Comparative Example 3 as a reference sample, and the average score was calculated. The larger the value, the better the flexibility imparting effect. The results are shown in Table 2.
[Criteria]
5 points: better flexibility than the reference sample (Comparative Example 3) 4 points: slightly better flexibility than the reference sample (Comparative Example 3) 3 points: flexibility equivalent to the reference sample (Comparative Example 3) 2 points: reference Slightly poorer than the sample (Comparative Example 3) 1 point: Less flexible than the reference sample (Comparative Example 3)
本発明の柔軟剤組成物は、繊維に対する柔軟性付与効果に優れているため、家庭用をはじめ各種繊維製品の柔軟仕上剤、特にタオル、肌着等の吸水性を要求される各種繊維製品の柔軟仕上剤として有効である。 Since the softener composition of the present invention is excellent in the effect of imparting flexibility to fibers, softening agents for various textile products including household use, especially for various textile products that require water absorption such as towels and underwear. Effective as a finishing agent.
Claims (7)
Furthermore, the softness | flexibility in any one of Claims 1-6 containing 1 or more types chosen from the group which consists of a nonionic surfactant (C), a hydrophilic solvent (D), and a water-soluble inorganic salt (E). Agent composition.
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