JP7552611B2

JP7552611B2 - 水性ポリマーエマルション及びその製造方法、並びに化粧料

水性ポリマーエマルション及びその製造方法、並びに化粧料 Download PDF

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Publication number: JP7552611B2
Authority: JP; Japan
Prior art keywords: monomer; emulsion; aqueous polymer; polymer emulsion; acid
Prior art date: 2019-11-11
Legal status : Active

Application number

JP2021556038A

Other languages

English (en)

Japanese (ja)

Other versions

JPWO2021095604A1 (enrdf_load_stackoverflow

Inventor

廣之柴田

明美纐纈

Current Assignee

Toagosei Co Ltd

Original Assignee

Toagosei Co Ltd

Priority date

2019-11-11

Filing date

2020-11-04

Publication date

2024-09-18

2020-11-04 Application filed by Toagosei Co Ltd filed Critical Toagosei Co Ltd

2021-05-20 Publication of JPWO2021095604A1 publication Critical patent/JPWO2021095604A1/ja

2024-09-18 Application granted granted Critical

2024-09-18 Publication of JP7552611B2 publication Critical patent/JP7552611B2/ja

Status Active legal-status Critical Current

2040-11-04 Anticipated expiration legal-status Critical

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239000000839 emulsion Substances 0.000 title claims description 212
229920000642 polymer Polymers 0.000 title claims description 71
239000002537 cosmetic Substances 0.000 title claims description 60
238000004519 manufacturing process Methods 0.000 title claims description 7
239000000178 monomer Substances 0.000 claims description 140
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 72
239000002245 particle Substances 0.000 claims description 69
239000000203 mixture Substances 0.000 claims description 52
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 50
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 32
125000000217 alkyl group Chemical group 0.000 claims description 28
239000012855 volatile organic compound Substances 0.000 claims description 24
229920001577 copolymer Polymers 0.000 claims description 23
238000007720 emulsion polymerization reaction Methods 0.000 claims description 22
230000009477 glass transition Effects 0.000 claims description 15
238000006116 polymerization reaction Methods 0.000 claims description 15
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 12
150000008064 anhydrides Chemical class 0.000 claims description 9
238000009835 boiling Methods 0.000 claims description 4
125000004122 cyclic group Chemical group 0.000 claims description 4
238000011068 loading method Methods 0.000 claims description 2
125000005395 methacrylic acid group Chemical group 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
-1 2-ethylhexyl Chemical group 0.000 description 118
230000000052 comparative effect Effects 0.000 description 45
239000003921 oil Substances 0.000 description 44
235000019198 oils Nutrition 0.000 description 44
229920003171 Poly (ethylene oxide) Polymers 0.000 description 41
235000014113 dietary fatty acids Nutrition 0.000 description 27
239000000194 fatty acid Substances 0.000 description 27
229930195729 fatty acid Natural products 0.000 description 27
238000011156 evaluation Methods 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
239000004094 surface-active agent Substances 0.000 description 21
239000000843 powder Substances 0.000 description 20
238000000034 method Methods 0.000 description 19
239000000047 product Substances 0.000 description 19
239000007788 liquid Substances 0.000 description 18
239000011248 coating agent Substances 0.000 description 17
238000000576 coating method Methods 0.000 description 17
235000019645 odor Nutrition 0.000 description 17
238000012360 testing method Methods 0.000 description 17
230000015572 biosynthetic process Effects 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
150000004665 fatty acids Chemical class 0.000 description 15
238000003786 synthesis reaction Methods 0.000 description 15
238000002156 mixing Methods 0.000 description 14
239000003505 polymerization initiator Substances 0.000 description 13
230000008569 process Effects 0.000 description 13
239000004166 Lanolin Substances 0.000 description 12
ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 12
235000019388 lanolin Nutrition 0.000 description 12
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239000000243 solution Substances 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 9
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238000004332 deodorization Methods 0.000 description 8
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NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
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150000001875 compounds Chemical class 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
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229910001870 ammonium persulfate Inorganic materials 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
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239000004417 polycarbonate Substances 0.000 description 6
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150000003839 salts Chemical class 0.000 description 6
238000005303 weighing Methods 0.000 description 6
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 5
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 5
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 5
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
239000005642 Oleic acid Substances 0.000 description 5
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 5
229920002472 Starch Polymers 0.000 description 5
150000005215 alkyl ethers Chemical class 0.000 description 5
235000011114 ammonium hydroxide Nutrition 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
210000003298 dental enamel Anatomy 0.000 description 5
125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 5
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
239000012071 phase Substances 0.000 description 5
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 5
229920000053 polysorbate 80 Polymers 0.000 description 5
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229920005989 resin Polymers 0.000 description 5
238000000926 separation method Methods 0.000 description 5
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235000019698 starch Nutrition 0.000 description 5
238000003756 stirring Methods 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
239000002202 Polyethylene glycol Substances 0.000 description 4
235000021355 Stearic acid Nutrition 0.000 description 4
229910052921 ammonium sulfate Inorganic materials 0.000 description 4
235000011130 ammonium sulphate Nutrition 0.000 description 4
239000003945 anionic surfactant Substances 0.000 description 4
238000007664 blowing Methods 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
238000009826 distribution Methods 0.000 description 4
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
238000001035 drying Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
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OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
239000004014 plasticizer Substances 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
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PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 3
QZCLKYGREBVARF-UHFFFAOYSA-N Acetyl tributyl citrate Chemical compound CCCCOC(=O)CC(C(=O)OCCCC)(OC(C)=O)CC(=O)OCCCC QZCLKYGREBVARF-UHFFFAOYSA-N 0.000 description 3
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 3
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238000002479 acid--base titration Methods 0.000 description 3
SOGAXMICEFXMKE-UHFFFAOYSA-N alpha-Methyl-n-butyl acrylate Natural products CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 3
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238000002296 dynamic light scattering Methods 0.000 description 3
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229910052582 BN Inorganic materials 0.000 description 2
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