JP2005132959A - Siloxane gel and method for producing the same - Google Patents
Siloxane gel and method for producing the same Download PDFInfo
- Publication number
- JP2005132959A JP2005132959A JP2003370433A JP2003370433A JP2005132959A JP 2005132959 A JP2005132959 A JP 2005132959A JP 2003370433 A JP2003370433 A JP 2003370433A JP 2003370433 A JP2003370433 A JP 2003370433A JP 2005132959 A JP2005132959 A JP 2005132959A
- Authority
- JP
- Japan
- Prior art keywords
- siloxane compound
- acid
- earth metal
- alkaline earth
- gel
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 title description 3
- -1 siloxane compound Chemical class 0.000 claims abstract description 90
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims abstract description 47
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 26
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims description 29
- 239000003349 gelling agent Substances 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 16
- QUUCYKKMFLJLFS-UHFFFAOYSA-N Dehydroabietan Natural products CC1(C)CCCC2(C)C3=CC=C(C(C)C)C=C3CCC21 QUUCYKKMFLJLFS-UHFFFAOYSA-N 0.000 claims description 8
- NFWKVWVWBFBAOV-UHFFFAOYSA-N Dehydroabietic acid Natural products OC(=O)C1(C)CCCC2(C)C3=CC=C(C(C)C)C=C3CCC21 NFWKVWVWBFBAOV-UHFFFAOYSA-N 0.000 claims description 8
- NFWKVWVWBFBAOV-MISYRCLQSA-N dehydroabietic acid Chemical compound OC(=O)[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 NFWKVWVWBFBAOV-MISYRCLQSA-N 0.000 claims description 8
- 229940118781 dehydroabietic acid Drugs 0.000 claims description 8
- MHVJRKBZMUDEEV-UHFFFAOYSA-N (-)-ent-pimara-8(14),15-dien-19-oic acid Natural products C1CCC(C(O)=O)(C)C2C1(C)C1CCC(C=C)(C)C=C1CC2 MHVJRKBZMUDEEV-UHFFFAOYSA-N 0.000 claims description 7
- MXYATHGRPJZBNA-KRFUXDQASA-N isopimaric acid Chemical compound [C@H]1([C@](CCC2)(C)C(O)=O)[C@@]2(C)[C@H]2CC[C@@](C=C)(C)CC2=CC1 MXYATHGRPJZBNA-KRFUXDQASA-N 0.000 claims description 6
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 5
- MXYATHGRPJZBNA-UHFFFAOYSA-N 4-epi-isopimaric acid Natural products C1CCC(C(O)=O)(C)C2C1(C)C1CCC(C=C)(C)CC1=CC2 MXYATHGRPJZBNA-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- MHVJRKBZMUDEEV-APQLOABGSA-N (+)-Pimaric acid Chemical compound [C@H]1([C@](CCC2)(C)C(O)=O)[C@@]2(C)[C@H]2CC[C@](C=C)(C)C=C2CC1 MHVJRKBZMUDEEV-APQLOABGSA-N 0.000 claims description 3
- YPGLTKHJEQHKSS-ASZLNGMRSA-N (1r,4ar,4bs,7r,8as,10ar)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-1-carboxylic acid Chemical compound [C@H]1([C@](CCC2)(C)C(O)=O)[C@@]2(C)[C@H]2CC[C@@H](C(C)C)C[C@@H]2CC1 YPGLTKHJEQHKSS-ASZLNGMRSA-N 0.000 claims description 3
- UZZYXZWSOWQPIS-UHFFFAOYSA-N 3-fluoro-5-(trifluoromethyl)benzaldehyde Chemical compound FC1=CC(C=O)=CC(C(F)(F)F)=C1 UZZYXZWSOWQPIS-UHFFFAOYSA-N 0.000 claims description 3
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 claims description 3
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 claims description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- RWWVEQKPFPXLGL-ONCXSQPRSA-N L-Pimaric acid Chemical compound [C@H]1([C@](CCC2)(C)C(O)=O)[C@@]2(C)[C@H]2CC=C(C(C)C)C=C2CC1 RWWVEQKPFPXLGL-ONCXSQPRSA-N 0.000 claims description 3
- RWWVEQKPFPXLGL-UHFFFAOYSA-N Levopimaric acid Natural products C1CCC(C(O)=O)(C)C2C1(C)C1CC=C(C(C)C)C=C1CC2 RWWVEQKPFPXLGL-UHFFFAOYSA-N 0.000 claims description 3
- KGMSWPSAVZAMKR-UHFFFAOYSA-N Me ester-3, 22-Dihydroxy-29-hopanoic acid Natural products C1CCC(C(O)=O)(C)C2C1(C)C1CCC(=C(C)C)C=C1CC2 KGMSWPSAVZAMKR-UHFFFAOYSA-N 0.000 claims description 3
- KGMSWPSAVZAMKR-ONCXSQPRSA-N Neoabietic acid Chemical compound [C@H]1([C@](CCC2)(C)C(O)=O)[C@@]2(C)[C@H]2CCC(=C(C)C)C=C2CC1 KGMSWPSAVZAMKR-ONCXSQPRSA-N 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 239000011575 calcium Substances 0.000 claims description 3
- 229910052712 strontium Inorganic materials 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- 229910052788 barium Inorganic materials 0.000 claims 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 19
- 238000010438 heat treatment Methods 0.000 abstract description 3
- 238000002844 melting Methods 0.000 abstract description 3
- 230000008018 melting Effects 0.000 abstract description 3
- 238000001816 cooling Methods 0.000 abstract description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- 239000000499 gel Substances 0.000 description 27
- 239000000243 solution Substances 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 18
- 238000001879 gelation Methods 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 6
- 239000000920 calcium hydroxide Substances 0.000 description 6
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000002537 cosmetic Substances 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 238000005649 metathesis reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 5
- 229920001202 Inulin Polymers 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- JYJIGFIDKWBXDU-MNNPPOADSA-N inulin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@]1(OC[C@]2(OC[C@]3(OC[C@]4(OC[C@]5(OC[C@]6(OC[C@]7(OC[C@]8(OC[C@]9(OC[C@]%10(OC[C@]%11(OC[C@]%12(OC[C@]%13(OC[C@]%14(OC[C@]%15(OC[C@]%16(OC[C@]%17(OC[C@]%18(OC[C@]%19(OC[C@]%20(OC[C@]%21(OC[C@]%22(OC[C@]%23(OC[C@]%24(OC[C@]%25(OC[C@]%26(OC[C@]%27(OC[C@]%28(OC[C@]%29(OC[C@]%30(OC[C@]%31(OC[C@]%32(OC[C@]%33(OC[C@]%34(OC[C@]%35(OC[C@]%36(O[C@@H]%37[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O%37)O)[C@H]([C@H](O)[C@@H](CO)O%36)O)[C@H]([C@H](O)[C@@H](CO)O%35)O)[C@H]([C@H](O)[C@@H](CO)O%34)O)[C@H]([C@H](O)[C@@H](CO)O%33)O)[C@H]([C@H](O)[C@@H](CO)O%32)O)[C@H]([C@H](O)[C@@H](CO)O%31)O)[C@H]([C@H](O)[C@@H](CO)O%30)O)[C@H]([C@H](O)[C@@H](CO)O%29)O)[C@H]([C@H](O)[C@@H](CO)O%28)O)[C@H]([C@H](O)[C@@H](CO)O%27)O)[C@H]([C@H](O)[C@@H](CO)O%26)O)[C@H]([C@H](O)[C@@H](CO)O%25)O)[C@H]([C@H](O)[C@@H](CO)O%24)O)[C@H]([C@H](O)[C@@H](CO)O%23)O)[C@H]([C@H](O)[C@@H](CO)O%22)O)[C@H]([C@H](O)[C@@H](CO)O%21)O)[C@H]([C@H](O)[C@@H](CO)O%20)O)[C@H]([C@H](O)[C@@H](CO)O%19)O)[C@H]([C@H](O)[C@@H](CO)O%18)O)[C@H]([C@H](O)[C@@H](CO)O%17)O)[C@H]([C@H](O)[C@@H](CO)O%16)O)[C@H]([C@H](O)[C@@H](CO)O%15)O)[C@H]([C@H](O)[C@@H](CO)O%14)O)[C@H]([C@H](O)[C@@H](CO)O%13)O)[C@H]([C@H](O)[C@@H](CO)O%12)O)[C@H]([C@H](O)[C@@H](CO)O%11)O)[C@H]([C@H](O)[C@@H](CO)O%10)O)[C@H]([C@H](O)[C@@H](CO)O9)O)[C@H]([C@H](O)[C@@H](CO)O8)O)[C@H]([C@H](O)[C@@H](CO)O7)O)[C@H]([C@H](O)[C@@H](CO)O6)O)[C@H]([C@H](O)[C@@H](CO)O5)O)[C@H]([C@H](O)[C@@H](CO)O4)O)[C@H]([C@H](O)[C@@H](CO)O3)O)[C@H]([C@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 JYJIGFIDKWBXDU-MNNPPOADSA-N 0.000 description 4
- 229940029339 inulin Drugs 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000004210 ether based solvent Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000003784 tall oil Substances 0.000 description 3
- ABFQGXBZQWZNKI-UHFFFAOYSA-N 1,1-dimethoxyethanol Chemical compound COC(C)(O)OC ABFQGXBZQWZNKI-UHFFFAOYSA-N 0.000 description 2
- FLZPTLSRDKJVLE-UHFFFAOYSA-N 1,2-dimethoxyethane-1,2-diol Chemical compound COC(O)C(O)OC FLZPTLSRDKJVLE-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004375 Dextrin Substances 0.000 description 2
- 229920001353 Dextrin Polymers 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 229940043430 calcium compound Drugs 0.000 description 2
- 150000001674 calcium compounds Chemical class 0.000 description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
- 239000000292 calcium oxide Substances 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- DWPDSISGRAWLLV-JHZYRPMRSA-L calcium;(1r,4ar,4br,10ar)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylate Chemical compound [Ca+2].C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C([O-])=O.C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C([O-])=O DWPDSISGRAWLLV-JHZYRPMRSA-L 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000008406 cosmetic ingredient Substances 0.000 description 2
- 235000019425 dextrin Nutrition 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- HTDJPCNNEPUOOQ-UHFFFAOYSA-N hexamethylcyclotrisiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O1 HTDJPCNNEPUOOQ-UHFFFAOYSA-N 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 239000011810 insulating material Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- IATRAKWUXMZMIY-UHFFFAOYSA-N strontium oxide Chemical compound [O-2].[Sr+2] IATRAKWUXMZMIY-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004034 viscosity adjusting agent Substances 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 1
- QSRINYFVPGFLSO-UHFFFAOYSA-N 2,2,4,4,6,6,8,8,10,10-decaethyl-1,3,5,7,9,2,4,6,8,10-pentaoxapentasilecane Chemical compound CC[Si]1(CC)O[Si](CC)(CC)O[Si](CC)(CC)O[Si](CC)(CC)O[Si](CC)(CC)O1 QSRINYFVPGFLSO-UHFFFAOYSA-N 0.000 description 1
- XOCOMEGNVMCRMP-UHFFFAOYSA-N 2,2,4,4,6,6,8,8-octaethyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound CC[Si]1(CC)O[Si](CC)(CC)O[Si](CC)(CC)O[Si](CC)(CC)O1 XOCOMEGNVMCRMP-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- NYNVGGZGDPTXOS-UHFFFAOYSA-N 2-ethyl-1,3,5,2,4,6-trioxatrisilinane Chemical compound C(C)[SiH]1O[SiH2]O[SiH2]O1 NYNVGGZGDPTXOS-UHFFFAOYSA-N 0.000 description 1
- IUMSDRXLFWAGNT-UHFFFAOYSA-N Dodecamethylcyclohexasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 IUMSDRXLFWAGNT-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- POPAYXQDNXXYSU-UHFFFAOYSA-N [diethyl(triethylsilyloxy)silyl]oxy-diethyl-triethylsilyloxysilane Chemical compound CC[Si](CC)(CC)O[Si](CC)(CC)O[Si](CC)(CC)O[Si](CC)(CC)CC POPAYXQDNXXYSU-UHFFFAOYSA-N 0.000 description 1
- VWGDPBQTSZDFMX-UHFFFAOYSA-N [dimethyl(trimethylsilyloxy)silyl]oxy-[[[[dimethyl(trimethylsilyloxy)silyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C VWGDPBQTSZDFMX-UHFFFAOYSA-N 0.000 description 1
- ADANNTOYRVPQLJ-UHFFFAOYSA-N [dimethyl(trimethylsilyloxy)silyl]oxy-[[dimethyl(trimethylsilyloxy)silyl]oxy-dimethylsilyl]oxy-dimethylsilane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C ADANNTOYRVPQLJ-UHFFFAOYSA-N 0.000 description 1
- YFCGDEUVHLPRCZ-UHFFFAOYSA-N [dimethyl(trimethylsilyloxy)silyl]oxy-dimethyl-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C YFCGDEUVHLPRCZ-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001553 barium compounds Chemical class 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- ZUDYPQRUOYEARG-UHFFFAOYSA-L barium(2+);dihydroxide;octahydrate Chemical compound O.O.O.O.O.O.O.O.[OH-].[OH-].[Ba+2] ZUDYPQRUOYEARG-UHFFFAOYSA-L 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
- FBZANXDWQAVSTQ-UHFFFAOYSA-N dodecamethylpentasiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C FBZANXDWQAVSTQ-UHFFFAOYSA-N 0.000 description 1
- 229940087203 dodecamethylpentasiloxane Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- HLPWCQDWRYCGLK-UHFFFAOYSA-N ethyl-methyl-bis(trimethylsilyloxy)silane Chemical compound C[Si](C)(C)O[Si](C)(CC)O[Si](C)(C)C HLPWCQDWRYCGLK-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- XKJMJYZFAWYREL-UHFFFAOYSA-N hexadecamethylcyclooctasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XKJMJYZFAWYREL-UHFFFAOYSA-N 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002681 magnesium compounds Chemical class 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- MHVJRKBZMUDEEV-KRFUXDQASA-N sandaracopimaric acid Chemical compound [C@H]1([C@](CCC2)(C)C(O)=O)[C@@]2(C)[C@H]2CC[C@@](C=C)(C)C=C2CC1 MHVJRKBZMUDEEV-KRFUXDQASA-N 0.000 description 1
- YZVSLDRKXBZOMY-KNOXWWKRSA-N sandaracopimaric acid Natural products CC(=C)[C@]1(C)CCC[C@]2(C)[C@H]3CC[C@](C)(C=C)C=C3CC[C@@H]12 YZVSLDRKXBZOMY-KNOXWWKRSA-N 0.000 description 1
- 150000003438 strontium compounds Chemical class 0.000 description 1
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- UJPWWRPNIRRCPJ-UHFFFAOYSA-L strontium;dihydroxide;octahydrate Chemical compound O.O.O.O.O.O.O.O.[OH-].[OH-].[Sr+2] UJPWWRPNIRRCPJ-UHFFFAOYSA-L 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940008424 tetradecamethylhexasiloxane Drugs 0.000 description 1
- WILBTFWIBAOWLN-UHFFFAOYSA-N triethyl(triethylsilyloxy)silane Chemical compound CC[Si](CC)(CC)O[Si](CC)(CC)CC WILBTFWIBAOWLN-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- KJBTUARYMVBZAE-UHFFFAOYSA-N trimethyl(trimethylsilyloxysilyloxysilyloxysilyloxysilyloxysilyloxy)silane Chemical compound C[Si](O[SiH2]O[SiH2]O[SiH2]O[SiH2]O[SiH2]O[Si](C)(C)C)(C)C KJBTUARYMVBZAE-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
本発明は、シロキサン化合物用ゲル化剤、シロキサン化合物（Ａ）のゲル、およびその製造方法に関する。さらに詳しくは、ケイ素原子を少なくとも２以上含有するシロキサン化合物に樹脂酸類のアルカリ土類金属塩を有効成分とする溶液を添加して得られるゲル化剤およびその製造方法に関する。 The present invention relates to a gelling agent for a siloxane compound, a gel of a siloxane compound (A), and a method for producing the same. More specifically, the present invention relates to a gelling agent obtained by adding a solution containing an alkaline earth metal salt of a resin acid as an active ingredient to a siloxane compound containing at least two silicon atoms and a method for producing the same.
シロキサン化合物は優れた耐熱性、耐寒性、耐候性、撥水性、電気特性などの特長を有するため、種々の用途、すなわち化粧品、医薬部外品、絶縁材料、潤滑剤、インキなどの粘度調節剤など非常に広い分野で用いられており、特にオクタメチルシクロテトラシロキサンやデカメチルシクロペンタシロキサンなどの環状シロキサンはべたつきのない、なめらかな感触を付与し、気体透過性、撥水性に優れ、他の混合成分とともに均一の皮膜を形成できるため、化粧料用成分として使われている材料である。 Siloxane compounds have excellent heat resistance, cold resistance, weather resistance, water repellency, electrical characteristics, etc., so they can be used in various applications such as cosmetics, quasi drugs, insulating materials, lubricants, inks, and other viscosity modifiers. In particular, cyclic siloxanes such as octamethylcyclotetrasiloxane and decamethylcyclopentasiloxane give a smooth and non-sticky feel, and have excellent gas permeability and water repellency. It is a material used as a cosmetic ingredient because it can form a uniform film with mixed ingredients.
しかし、シロキサン化合物、特にオクタメチルシクロテトラシロキサンやデカメチルシクロペンタシロキサンなどはそれ自体では粘度が低く流動性に富み、化粧料用の配合成分として多量に用いることができないという欠点がある。このためシロキサン化合物の粘度を高め、流動性を少なくさせることは、特に化粧料として有効であるため、シロキサン化合物をゲル化させる方法が求められている。 However, siloxane compounds, particularly octamethylcyclotetrasiloxane and decamethylcyclopentasiloxane, have a drawback that they themselves have low viscosity and high fluidity, and cannot be used in large quantities as cosmetic ingredients. For this reason, increasing the viscosity of the siloxane compound and reducing the fluidity is particularly effective as a cosmetic, so a method for gelling the siloxane compound is required.
そこで、環状シロキサンをゲル化させる方法としてデキストリンの部分脂肪酸エステルとイヌリンおよび／または加水分解イヌリンの部分脂肪酸エステルの２種の化合物を用いてゲル化ざせる方法が提案されている（特許文献１および特許文献２）が、当該方法では二種類の化合物が必須であり、デキストリンの部分脂肪酸エステルならびに、イヌリン及び／または加水分解イヌリンの部分脂肪酸エステルのエステル化率を微妙に調整する必要があるうえ、当該化合物の合成も煩雑であり、さらには、これら二種の化合物をある一定の比で使用しなければゲル化できないものであった。 Therefore, as a method for gelling cyclic siloxane, there has been proposed a method for gelling using two types of compounds, partial fatty acid ester of dextrin and inulin and / or partial fatty acid ester of hydrolyzed inulin (Patent Document 1 and Patent Document 2) requires two kinds of compounds in the method, and it is necessary to finely adjust the esterification rate of the partial fatty acid ester of dextrin and the partial fatty acid ester of inulin and / or hydrolyzed inulin, The synthesis of the compound is complicated, and furthermore, it cannot be gelled unless these two kinds of compounds are used in a certain ratio.
また、当該方法では、環状シロキサンゲル化合物、またはそれらを含む化粧料組成物に添加し、一旦加熱して溶解させ、その後冷却してゲル化させる必要があり、操作が煩雑でその用途が非常に制限されている。さらに、生成したゲルを再び加熱すると、ゲル強度が低下したり、ゲルが溶解するという致命的な欠点がある。 In addition, in this method, it is necessary to add to the cyclic siloxane gel compound or a cosmetic composition containing them, once to dissolve by heating, and then to cool and gel, and the operation is complicated and its application is very Limited. Furthermore, when the produced gel is heated again, there is a fatal defect that the gel strength is lowered or the gel is dissolved.
なお、本発明者は、先に有機ゲル化剤について提案をしているが、当該ゲル化剤をシロキサン化合物に適用することについては検討がされていなかった。（特許文献３） In addition, although this inventor has proposed about the organic gelling agent previously, it has not examined about applying the said gelling agent to a siloxane compound. (Patent Document 3)
本発明は、低添加量でシロキサン化合物をゲル化させることができるシロキサン化合物用ゲル化剤を提供し、かつ加温、冷却することなく、室温でゲル化対象物に添加するだけで容易にゲル化できるシロキサン化合物のゲルの製造方法を提供し、さらには加熱してもゲル強度が低下したり、溶解することのない新規なシロキサン化合物のゲルを提供することを目的とする。 The present invention provides a gelling agent for a siloxane compound that can gel a siloxane compound with a low addition amount, and can be easily gelled only by adding to a gelation object at room temperature without heating and cooling. It is an object of the present invention to provide a method for producing a gel of a siloxane compound that can be converted into a gel, and to provide a novel gel of a siloxane compound that does not decrease in gel strength or dissolve even when heated.
かかる目的を達成するために、本発明者は鋭意検討した結果、樹脂酸類のアルカリ土類金属塩を用いることにより当該目的を達成しうることを見出した。 In order to achieve such an object, the present inventor has intensively studied and found that the object can be achieved by using an alkaline earth metal salt of a resin acid.
すなわち、本発明は、樹脂酸のアルカリ土類金属塩を含有することを特徴とするシロキサン化合物用ゲル化剤；ケイ素原子を少なくとも２以上含有するシロキサン化合物（Ａ）を、当該シロキサン化合物用ゲル化剤でゲル化させることにより得られるゲル；ケイ素原子を少なくとも２以上含有するシロキサン化合物（Ａ）に当該シロキサン化合物用ゲル化剤を添加することを特徴とするゲルの製造方法に関する。 That is, the present invention relates to a gelling agent for a siloxane compound characterized by containing an alkaline earth metal salt of a resin acid; a siloxane compound (A) containing at least two silicon atoms is gelled for the siloxane compound. A gel obtained by gelling with an agent; a method for producing a gel comprising adding a gelling agent for a siloxane compound to a siloxane compound (A) containing at least two silicon atoms.
本発明のシロキサン化合物用ゲル化剤によれば、少量の添加により、シロキサン化合物をゲル化させることができる。また、当該ゲル化剤を用いて得られたシロキサン化合物のゲルは、従来のシロキサン化合物のゲルと異なり加熱しても強度が低下したり、溶解することが無いという、新規有用なゲルである。本発明のゲルの作用効果を活かして、化粧品、医薬部外品、医薬品、農薬、香料などの徐放剤、絶縁材料、潤滑剤、インキ、塗料などの粘度調節剤など非常に広い分野で用いることができる。特にオクタメチルシクロテトラシロキサンやデカメチルシクロペンタシロキサンなどの環状シロキサン化合物のゲルはべたつきのない、なめらかな感触を付与し、気体透過性、撥水性に優れ、他の混合成分とともに均一の皮膜を形成できるため、化粧料用に好適である。 According to the gelling agent for siloxane compounds of the present invention, the siloxane compound can be gelled by adding a small amount. Moreover, the gel of the siloxane compound obtained by using the said gelling agent is a novel useful gel which does not fall in intensity | strength or melt | dissolve even if it heats unlike the gel of the conventional siloxane compound. Utilizing the effects of the gel of the present invention, it is used in a very wide range of fields such as sustained release agents such as cosmetics, quasi drugs, pharmaceuticals, agricultural chemicals, and fragrances, viscosity modifiers such as insulating materials, lubricants, inks, and paints. be able to. In particular, cyclic siloxane compound gels such as octamethylcyclotetrasiloxane and decamethylcyclopentasiloxane provide a smooth, non-sticky feel, excellent gas permeability and water repellency, and form a uniform film with other mixed components. Therefore, it is suitable for cosmetics.
本発明のシロキサン化合物用ゲル化剤は、有効成分として樹脂酸類のアルカリ土類金属塩を含有するものである。当該樹脂酸類のアルカリ土類金属塩は、通常二つの樹脂酸残基とアルカリ土類金属から構成される化合物であり、樹脂酸類とアルカリ土類金属化合物とを反応させることにより得られる。 The gelling agent for siloxane compounds of the present invention contains an alkaline earth metal salt of a resin acid as an active ingredient. The alkaline earth metal salt of the resin acid is usually a compound composed of two resin acid residues and an alkaline earth metal, and is obtained by reacting a resin acid with an alkaline earth metal compound.
樹脂酸類としては、特に制限されず公知のものを使用することができる。具体的には、例えば、アビエチン酸、レボピマル酸、ネオアビエチン酸、パラストリン酸、ピマル酸、イソピマル酸、サンダラコピマル酸、デヒドロアビエチン酸、ジヒドロアビエチン酸類、テトラヒドロアビエチン酸類をあげることができる。また、前記樹脂酸の混合物であるガムロジン、ウッドロジン、トール油ロジン等のロジン類の他、ロジン類を不均化して得られる不均化ロジン、ロジン類を水素化して得られる水素化ロジン、ロジン類を脱水素化して得られる脱水素化ロジンなども用いることができるが、アビエチン酸、レボピマル酸、ネオアビエチン酸、パラストリン酸、ピマル酸、イソピマル酸、サンダラコピマル酸、デヒドロアビエチン酸、ジヒドロアビエチン酸およびテトラヒドロアビエチン酸からなる群より選ばれる少なくとも１種挙げられる。 The resin acids are not particularly limited, and known acids can be used. Specific examples include abietic acid, levopimaric acid, neoabietic acid, parastrinic acid, pimaric acid, isopimaric acid, sandaracopimalic acid, dehydroabietic acid, dihydroabietic acid, and tetrahydroabietic acid. In addition to rosins such as gum rosin, wood rosin, tall oil rosin and the like, which are a mixture of the resin acids, disproportionated rosin obtained by disproportionating rosins, hydrogenated rosin obtained by hydrogenating rosins, rosin Although dehydrogenated rosin obtained by dehydrogenation of acetylene can also be used, abietic acid, levopimaric acid, neoabietic acid, parastrinic acid, pimaric acid, isopimaric acid, sandaracopimaric acid, dehydroabietic acid, dihydroabietic acid And at least one selected from the group consisting of acids and tetrahydroabietic acid.
アルカリ土類金属化合物としては、樹脂酸類と反応して塩を形成するアルカリ土類金属化合物であれば特に制限されず、公知のものを使用することができる。具体的には、カルシウム化合物、ストロンチウム化合物、バリウム化合物、マグネシウム化合物などが挙げられる。これらのうちでは、コスト、安全性等の面からカルシウム化合物を用いたものが好ましい。なお、これらアルカリ土類金属化合物のうちでは、樹脂酸類との反応性の点から、アルカリ土類金属の酸化物またはアルカリ土類金属の水酸化物を用いることが好ましい。これらの具体例としては、水酸化マグネシウム、酸化マグネシウム、水酸化カルシウム、酸化カルシウム、水酸化ストロンチウム、酸化ストロンチウム、水酸化バリウム、酸化バリウムなどを用いることが好ましく、酸化カルシウム、水酸化カルシウムを用いることが特に好ましい。 The alkaline earth metal compound is not particularly limited as long as it is an alkaline earth metal compound that reacts with resin acids to form a salt, and a known one can be used. Specific examples include calcium compounds, strontium compounds, barium compounds, magnesium compounds, and the like. Among these, those using a calcium compound are preferable from the viewpoints of cost, safety, and the like. Among these alkaline earth metal compounds, it is preferable to use an alkaline earth metal oxide or an alkaline earth metal hydroxide from the viewpoint of reactivity with resin acids. As these specific examples, it is preferable to use magnesium hydroxide, magnesium oxide, calcium hydroxide, calcium oxide, strontium hydroxide, strontium oxide, barium hydroxide, barium oxide, etc., and use calcium oxide and calcium hydroxide. Is particularly preferred.
本発明に用いられる樹脂酸類のアルカリ土類金属塩の合成方法としては、例えば、樹脂酸類を適当な溶媒中で反応させる方法が挙げられる。溶媒としては、樹脂酸類およびアルカリ土類金属化合物と反応せず、樹脂酸類を溶解するものであれば、特に制限されず、公知のものを用いることができる。具体的には、例えば、メタノール、エタノール、１−プロパノール、２−プロパノール、１−ブタノール、エチレングリコール、プロピレングリコール、ジエチレングリコール、トリエチレングリコール、２−メトキシエタノールなどのアルコール類、アセトン、２−ブタノン等のケトン類、ジメチルホルムアミド、ジメチルアセトアミド、Ｎ−メチルピロリドンなどのアミド類、ジメチルスルホキシド、スルホランなどの含イオウ溶媒、ニトロメタン、ニトロプロパン等の含窒素溶媒、ジエチルエーテル、メチルｔ−ブチルエーテル、ジｔ−ブチルエーテル、ジメトキシエタノール、ジメトキシエチレングリコール、テトラヒドロフラン、ジオキサンなどのエーテル結合を少なくとも一つ有するエーテル系溶媒などが挙げられる。これらのうち、エーテル系溶媒を反応溶媒に用いた場合には、反応後の樹脂酸類のアルカリ土類金属塩はこれらの溶媒に溶解した状態で得られ、このものはそのままゲル化剤として使用できるため、これらエーテル系溶媒を使うことが好ましい。尚、溶媒中に少量の水を存在させることにより、樹脂酸類とアルカリ土類金属化合物の反応速度を速くすることができるため特に好ましい。 Examples of the method for synthesizing the alkaline earth metal salt of the resin acid used in the present invention include a method of reacting the resin acid in an appropriate solvent. The solvent is not particularly limited as long as it does not react with the resin acid and the alkaline earth metal compound and dissolves the resin acid, and a known solvent can be used. Specifically, for example, alcohols such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, 2-methoxyethanol, acetone, 2-butanone, etc. Ketones, amides such as dimethylformamide, dimethylacetamide, N-methylpyrrolidone, sulfur-containing solvents such as dimethyl sulfoxide and sulfolane, nitrogen-containing solvents such as nitromethane and nitropropane, diethyl ether, methyl t-butyl ether, di-t- Examples thereof include ether solvents having at least one ether bond such as butyl ether, dimethoxyethanol, dimethoxyethylene glycol, tetrahydrofuran, and dioxane. Among these, when an ether solvent is used as the reaction solvent, the alkaline earth metal salt of the resin acid after the reaction is obtained in a state dissolved in these solvents, and this can be used as a gelling agent as it is. Therefore, it is preferable to use these ether solvents. The presence of a small amount of water in the solvent is particularly preferable because the reaction rate between the resin acid and the alkaline earth metal compound can be increased.
樹脂酸類とアルカリ土類金属化合物とを反応させる際の樹脂酸類とアルカリ土類金属化合物のモル比は、特に制限されないが、一般的にエーテル系溶媒を用いた場合には、樹脂酸１モルに対し、アルカリ土類金属化合物を０．２モル以上使用することが好ましい。樹脂酸類１モルに対し、アルカリ土類金属化合物が０．２モル未満となる場合には、未反応の樹脂酸類が多く残存してしまいゲル化性能を十分に発揮できない場合もある。また、樹脂酸類１モルに対し、アルカリ土類金属化合物を、０．５モルを超えて使用する場合には、未反応のアルカリ土類金属化合物が残存するが、ゲル化性能には問題はない。必要であれば、ろ過や遠心分離により未反応のアルカリ土類金属化合物を除去できる。また、エーテル系溶媒以外の溶媒を用いる場合には、通常、樹脂酸１モルに対し、アルカリ土類金属化合物を０．２モル以上使用することが好ましい。なお、樹脂酸類１モルに対し、アルカリ土類金属化合物を０．５モルを超えて使用する場合には、未反応のアルカリ土類金属化合物が残存するが、ゲル化性能には問題はない。 The molar ratio of the resin acid to the alkaline earth metal compound when the resin acid and the alkaline earth metal compound are reacted is not particularly limited. Generally, when an ether solvent is used, 1 mole of the resin acid is used. On the other hand, it is preferable to use 0.2 mol or more of alkaline earth metal compound. When the amount of the alkaline earth metal compound is less than 0.2 mol with respect to 1 mol of the resin acids, a large amount of unreacted resin acids may remain and the gelling performance may not be sufficiently exhibited. In addition, when the alkaline earth metal compound is used in an amount exceeding 0.5 mol with respect to 1 mol of the resin acid, an unreacted alkaline earth metal compound remains, but there is no problem in gelling performance. . If necessary, unreacted alkaline earth metal compound can be removed by filtration or centrifugation. In addition, when a solvent other than the ether solvent is used, it is usually preferable to use 0.2 mol or more of the alkaline earth metal compound with respect to 1 mol of the resin acid. In addition, when the alkaline earth metal compound is used in an amount exceeding 0.5 mol with respect to 1 mol of the resin acid, an unreacted alkaline earth metal compound remains, but there is no problem in gelling performance.
反応温度は、特に制限されないが、通常、特殊な装置を要することのない室温から反応に用いる溶媒の沸点の範囲が好適である。 The reaction temperature is not particularly limited, but usually the range of room temperature without requiring a special apparatus to the boiling point of the solvent used for the reaction is suitable.
反応時間は、反応温度により異なるが、通常５分から２４時間程度である。５分に満たない場合には反応が十分に進行しない場合があり、２４時間以上反応を行なっても特に有利な点はない。 The reaction time varies depending on the reaction temperature, but is usually about 5 minutes to 24 hours. If it is less than 5 minutes, the reaction may not proceed sufficiently, and there is no particular advantage even if the reaction is carried out for 24 hours or longer.
エーテル系溶媒以外の溶媒を用いた場合には、通常、反応終了後、樹脂酸類のアルカリ土類金属塩は反応溶媒中に粉末となって分散しており、ろ過あるいは遠心分離により反応溶媒と分離でき、必要に応じて、樹脂酸類のアルカリ土類金属塩を溶解しない溶媒で洗浄できる。得られた樹脂酸類のアルカリ土類金属塩は、例えば、ジエチルエーテル、メチルｔ−ブチルエーテル、ジｔ−ブチルエーテル、ジメトキシエタノール、ジメトキシエチレングリコール、テトラヒドロフラン、ジオキサンなどのエーテル結合を含む溶媒や樹脂酸類のアルカリ土類金属塩を溶解する溶媒に溶解して本発明に使用できる。 When a solvent other than an ether solvent is used, the alkaline earth metal salt of the resin acid is usually dispersed as a powder in the reaction solvent after completion of the reaction, and separated from the reaction solvent by filtration or centrifugation. If necessary, it can be washed with a solvent that does not dissolve the alkaline earth metal salt of the resin acid. The alkaline earth metal salt of the obtained resin acid is, for example, a solvent containing an ether bond such as diethyl ether, methyl t-butyl ether, di-t-butyl ether, dimethoxyethanol, dimethoxyethylene glycol, tetrahydrofuran, dioxane, or an alkali of a resin acid. It can be used in the present invention after being dissolved in a solvent that dissolves the earth metal salt.
なお、前記の方法で樹脂酸類のアルカリ土類金属塩の合成が困難な場合、一般的に複分解法と呼ばれる方法も採用できる。複分解法とは樹脂酸類を一旦、アルカリ金属水酸化物と反応させ樹脂酸類のアルカリ金属塩とした後、アルカリ土類金属化合物と反応させる方法である。 If it is difficult to synthesize an alkaline earth metal salt of a resin acid by the above method, a method generally called a metathesis method can also be adopted. The metathesis method is a method in which a resin acid is once reacted with an alkali metal hydroxide to obtain an alkali metal salt of the resin acid and then reacted with an alkaline earth metal compound.
複分解法では、樹脂酸類のアルカリ金属塩を反応させるアルカリ土類金属化合物としては、通常、水溶性の有機アルカリ土類金属塩類、無機アルカリ土類金属塩類を用いれば良い。具体的にはアルカリ土類金属の酢酸塩、硫酸塩、硝酸塩、塩化物およびこれらの水和物などが挙げられる。 In the metathesis method, water-soluble organic alkaline earth metal salts and inorganic alkaline earth metal salts are usually used as the alkaline earth metal compound with which the alkali metal salt of the resin acid is reacted. Specific examples include alkaline earth metal acetates, sulfates, nitrates, chlorides and hydrates thereof.
複分解法による場合には、反応終了後、生成物は反応溶媒である水に分散した状態で存在するため、ろ過あるいは遠心分離により容易に水と分離できる。また、生成物の水による洗浄も可能である。 In the case of the metathesis method, after completion of the reaction, the product exists in a dispersed state in water as a reaction solvent, and therefore can be easily separated from water by filtration or centrifugation. It is also possible to wash the product with water.
複分解法により得られた樹脂酸類のアルカリ土類金属塩は前記エーテル系溶媒や樹脂酸類のアルカリ土類金属塩を溶解する溶媒に溶解して本発明に使用できる。 The alkaline earth metal salt of a resin acid obtained by the metathesis method can be used in the present invention after being dissolved in the ether solvent or a solvent capable of dissolving the alkaline earth metal salt of a resin acid.
本発明のゲルの製造に用いられるケイ素原子を少なくとも２以上含有するシロキサン化合物（Ａ）（以下、（Ａ）成分という。）は、ケイ素原子を少なくとも２以上含有するものであれば特に制限されず、公知のものを使用することができる。当該（Ａ）成分の具体例としては、例えば、環状シロキサン化合物、鎖状シロキサン化合物などが挙げられる。環状シロキサン化合物としては、環状構造を有するシロキサンであれば特に制限されないが、一般式（１）： The siloxane compound (A) containing at least two silicon atoms (hereinafter referred to as component (A)) used for producing the gel of the present invention is not particularly limited as long as it contains at least two silicon atoms. Well-known ones can be used. Specific examples of the component (A) include cyclic siloxane compounds and chain siloxane compounds. Although it will not restrict | limit especially if it is a siloxane which has a cyclic structure as a cyclic siloxane compound, General formula (1):
（式中、Ｒ１は炭素数１〜４の低級アルキル基であって、同一であっても異なっていても良い置換基であり、ｎは３〜１０の整数を表す。）で表される環状シロキサン化合物を用いることが好ましい。環状シロキサン化合物の具体例としては、例えば、ヘキサメチルシクロトリシロキサン、オクタメチルシクロテトラシロキサン、デカメチルシクロペンタシロキサン、ドデカメチルシクロヘキサシロキサン、ペンタデカメチルシクロヘプタシロキサン、ヘキサデカメチルシクロオクタシロキサン、ヘキサエチルシクロトリシロキサン、オクタエチルシクロテトラシロキサン、デカエチルシクロペンタシロキサン、などが挙げられる。これらの中では、ヘキサメチルシクロトリシロキサン、オクタメチルシクロテトラシロキサン、デカメチルシクロペンタシロキサンが化粧料用途としては好ましい。
また、鎖状シロキサン化合物としては、特に制限されず、公知のものを使用することができるが具体的には、一般式（２）：
(Wherein R 1 is a lower alkyl group having 1 to 4 carbon atoms, which may be the same or different, and n represents an integer of 3 to 10). It is preferable to use a cyclic siloxane compound. Specific examples of the cyclic siloxane compound include, for example, hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, pentadecamethylcycloheptasiloxane, hexadecamethylcyclooctasiloxane, hexa Examples include ethylcyclotrisiloxane, octaethylcyclotetrasiloxane, decaethylcyclopentasiloxane, and the like. Among these, hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane, and decamethylcyclopentasiloxane are preferable for cosmetic use.
Further, the chain siloxane compound is not particularly limited, and a known one can be used. Specifically, the general formula (2):
（式中、Ｒ２は炭素数１〜４の低級アルキル基であり、同一であっても異なっていても良い置換基であり、ｍは０〜８の整数を表す）で挙げられるものを用いることが好ましい。具体的には、例えば、ヘキサメチルジシロキサン、オクタメチルトリシロキサン、デカメチルテトラシロキサン、ドデカメチルペンタシロキサン、テトラデカメチルヘキサシロキサン、ヘキサメチルヘプタシロキサン、オクタデカメチルオクタシロキサン、ヘキサエチルジシロキサン、オクタエチルトリシロキサン、デカエチルテトラシロキサン、ドデカエチルペンタシロキサンなどをあげることができる。なお、これらシロキサン化合物は、分岐構造を有するものであっても良い。 (Wherein R 2 is a lower alkyl group having 1 to 4 carbon atoms, which may be the same or different, and m represents an integer of 0 to 8). It is preferable. Specifically, for example, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, tetradecamethylhexasiloxane, hexamethylheptasiloxane, octadecamethyloctasiloxane, hexaethyldisiloxane, octadeca Examples thereof include ethyltrisiloxane, decaethyltetrasiloxane, dodecaethylpentasiloxane and the like. These siloxane compounds may have a branched structure.
本発明のシロキサンゲルは前記シロキサン化合物用ゲル化剤を（Ａ）成分に添加することにより得られる。なお、本発明のゲル化剤を添加する場合には、当該ゲル化剤を溶解する溶媒に溶解して使用することで速やかにゲル化を進行させることができる。当該ゲル化剤を溶解する溶媒としては、例えば、ゲル化剤を調整する際に用いられたエーテル系溶剤などが挙げられるが、これらに限定されるものではない。 The siloxane gel of the present invention can be obtained by adding the siloxane compound gelling agent to the component (A). In addition, when adding the gelatinizer of this invention, gelatinization can be advanced rapidly by melt | dissolving and using the said gelatinizer in the solvent which melt | dissolves. Examples of the solvent that dissolves the gelling agent include, but are not limited to, ether solvents used when adjusting the gelling agent.
シロキサン化合物用ゲル化剤を溶媒に溶解して用いる場合には、シロキサン化合物用ゲル化剤中に含まれる樹脂酸類のアルカリ土類金属塩の含有量を、溶媒に対し２重量％以上含有するように調整することが好ましく、できるだけ高濃度とするのが好ましい。２重量％に満たない場合には、ゲル化能力を十分に発揮できない場合がある。通常は、１０重量％以上とすることが特に好ましい。 When the siloxane compound gelling agent is used by dissolving in a solvent, the content of the alkaline earth metal salt of the resin acid contained in the siloxane compound gelling agent should be 2% by weight or more based on the solvent. It is preferable that the concentration be as high as possible. If it is less than 2% by weight, the gelation ability may not be fully exhibited. Usually, it is particularly preferably 10% by weight or more.
当該溶媒に溶解させたシロキサン化合物用ゲル化剤の使用量は、通常、シロキサン化合物の種類および樹脂酸のアルカリ土類金属塩の種類に応じて適宜に決定される。通常はシロキサン化合物に対してアルカリ土類金属塩の含有量が０．０５〜３０重量％程度、好ましくは０．１〜１０重量％となるようにする。 The amount of the siloxane compound gelling agent dissolved in the solvent is usually appropriately determined according to the type of the siloxane compound and the type of the alkaline earth metal salt of the resin acid. Usually, the content of the alkaline earth metal salt is about 0.05 to 30% by weight, preferably 0.1 to 10% by weight, based on the siloxane compound.
このようにして得られたシロキサン化合物のゲルにはアルカリ土類金属塩溶液とするために用いた溶剤が含まれている。場合によってはその溶剤を除去することもできる。溶剤除去法としては、例えば、常圧あるいは減圧下で蒸発させる方法が挙げられる。例えばアルカリ土類金属塩溶液の用いる溶剤にテトラヒドロフランを用いた場合、常圧あるいは減圧下で容易に除去できる。 The gel of the siloxane compound thus obtained contains a solvent used for preparing an alkaline earth metal salt solution. In some cases, the solvent can be removed. Examples of the solvent removal method include a method of evaporating under normal pressure or reduced pressure. For example, when tetrahydrofuran is used as the solvent used in the alkaline earth metal salt solution, it can be easily removed under normal pressure or reduced pressure.
以下に実施例をあげて本発明をさらに具体的に説明するが、本発明はこれら実施例に限定されるものではない。 The present invention will be described more specifically with reference to the following examples, but the present invention is not limited to these examples.
実施例１
デヒドロアビエチン酸３．００ｇ（１０ｍｍｏｌ）をテトラヒドロフラン１４．５ｇ、水０．５ｇよりなる混合溶媒に溶解し、これに水酸化カルシウム０．３７ｇ（５ｍｍｏｌ）を加え室温で攪拌し反応させた。反応後不溶物をろ過しデヒドロアビエチン酸カルシウム塩の溶液を得た。このものの一部をとり１０５℃、２時間乾燥しその乾燥減量から固形分を求め、乾燥した固形物のＩＲスペクトルを測定した。
固形分：１７．２重量％
ＩＲ：１５２１ｃｍ−１、１４１５ｃｍ−１
得られたデヒドロアビエチン酸カルシウム塩にさらにテトラヒドロフランを加え１５重量％溶液とした。
表１に示したシロキサン化合物１０ｇを試験管に取り、室温で攪拌しながら、表１に示した重量のテトラヒドロフランの１５重量％溶液をゲル形成の有無を観察した。結果を表１に示す。
Example 1
3.00 g (10 mmol) of dehydroabietic acid was dissolved in a mixed solvent consisting of 14.5 g of tetrahydrofuran and 0.5 g of water, 0.37 g (5 mmol) of calcium hydroxide was added thereto, and the mixture was stirred and reacted at room temperature. After the reaction, insolubles were filtered to obtain a solution of calcium dehydroabietic acid. A portion of this was taken and dried at 105 ° C. for 2 hours, the solid content was determined from the loss on drying, and the IR spectrum of the dried solid was measured.
Solid content: 17.2% by weight
IR: 1521 cm −1 , 1415 cm −1
Tetrahydrofuran was further added to the obtained calcium salt of dehydroabietic acid to make a 15 wt% solution.
10 g of the siloxane compound shown in Table 1 was placed in a test tube, and while stirring at room temperature, the presence or absence of gel formation of a 15 wt% solution of tetrahydrofuran having the weight shown in Table 1 was observed. The results are shown in Table 1.
実施例２
実施例１のデヒドロアビエチン酸３．００ｇ（１０ｍモル）に代えて不均化ロジン（商品名：ロンヂスＲ、荒川化学工業(株)製、酸価１５８）３．５４ｇを用いたほかは同様な操作を行い不均化ロジンカルシウム塩の溶液を得た。
固形分：１９．３重量％
ＩＲ：１５２５ｃｍ−１、１４１８ｃｍ−１
得られた溶液にさらにテトラヒドロフランを加え１５重量％とした。
ゲル化対象物１０ｇを試験管に取り、室温で攪拌しながら、表２に示した重量のテトラヒドロフランの１５重量％溶液を加えゲル形成の有無を観察した。結果を表２に示す。
Example 2
The same procedure except that 3.54 g of disproportionated rosin (trade name: Longis R, manufactured by Arakawa Chemical Industries, Ltd., acid value 158) was used instead of 3.00 g (10 mmol) of dehydroabietic acid in Example 1. Operation was performed to obtain a solution of disproportionated rosin calcium salt.
Solid content: 19.3% by weight
IR: 1525 cm −1 , 1418 cm −1
Tetrahydrofuran was further added to the obtained solution to make 15% by weight.
10 g of the object to be gelled was placed in a test tube, and while stirring at room temperature, a 15 wt% solution of tetrahydrofuran having the weight shown in Table 2 was added, and the presence or absence of gel formation was observed. The results are shown in Table 2.
実施例３
実施例１のデヒドロアビエチン酸３．００ｇ（１０ｍモル）に代えてトール油ロジン（商品名：ＴＯＲ３５−２４０、アリゾナケミカル社製、酸価１７１）３．２７ｇを用いたほかは同様な操作を行いトール油ロジンカルシウム塩の溶液を得た。
固形分：１８．６重量％
ＩＲ：１５２４ｃｍ−１、１４１７ｃｍ−１
得られた溶液にさらにテトラヒドロフラン溶液を加え１５重量％とした。
ゲル化対象物１０ｇを試験管に取り、室温で攪拌しながら、表３に示した重量のテトラヒドロフランの１５重量％溶液を加えゲル形成の有無を観察した。結果を表３に示す。
Example 3
The same operation was performed except that 3.27 g of tall oil rosin (trade name: TOR35-240, manufactured by Arizona Chemical Co., acid value 171) was used instead of 3.00 g (10 mmol) of dehydroabietic acid of Example 1. A solution of tall oil rosin calcium salt was obtained.
Solid content: 18.6% by weight
IR: 1524 cm −1 , 1417 cm −1
A tetrahydrofuran solution was further added to the obtained solution to make 15% by weight.
10 g of the object to be gelled was placed in a test tube, and while stirring at room temperature, a 15 wt% solution of tetrahydrofuran having the weight shown in Table 3 was added, and the presence or absence of gel formation was observed. The results are shown in Table 3.
実施例４
実施例１の水酸化カルシウム０．３７ｇ（５ｍモル）に代えて水酸化ストロンチウム・８水和物１．３３ｇ（５ｍモル）用いたほかは同様な操作を行いデヒドロアビエチン酸ストロンチウム塩の溶液を得た。
固形分：１７．６重量％
ＩＲ：１５２５ｃｍ−１、１４０５ｃｍ−１
得られた溶液にさらにテトラヒドロフラン溶液を加え１５重量％とした。
ゲル化対象物１０ｇを試験管に取り、室温で攪拌しながら、表４に示した重量のテトラヒドロフランの１５重量％溶液を加えゲル形成の有無を観察した。結果を表４に示す。
Example 4
A solution of strontium dehydroabietic acid salt was obtained in the same manner as in Example 1 except that 1.33 g (5 mmol) of strontium hydroxide octahydrate was used instead of 0.37 g (5 mmol) of calcium hydroxide. It was.
Solid content: 17.6% by weight
IR: 1525 cm −1 , 1405 cm −1
A tetrahydrofuran solution was further added to the obtained solution to make 15% by weight.
10 g of the gelation target was placed in a test tube, and while stirring at room temperature, a 15 wt% solution of tetrahydrofuran having the weight shown in Table 4 was added, and the presence or absence of gel formation was observed. The results are shown in Table 4.
実施例５
イソプロパノール（８８重量％）、水(１２重量％)からなる混合物（以下、８８％ＩＰＡと略す）２００ｇに水酸化カルシウム３．７ｇ（０．０５モル）を加え攪拌し分散させた後、精製不均化ロジン（商品名：ＫＲ−６１４、荒川化学工業(株)製、酸価１７３）３３ｇを８８％ＩＰＡ ２００ｇに溶解した溶液を還流下で３０分かけて滴下した。さらに還流下で４時間攪拌し冷却後、ろ過し、８８％ＩＰＡ１００ｇにて洗浄した。得られたろ過物を取り出し、８０℃で４時間減圧乾燥し、２８．８ｇの白色粉末を得た。
融点：３００℃まで溶融せず
ＩＲ：１５２１ｃｍ−１、１４１４ｃｍ−１
このものをテトラヒドロフランに溶解し１５重量％溶液を調製した。
ゲル化対象物１０ｇを試験管に取り、室温で攪拌しながら、表５に示した重量のテトラヒドロフラン溶液の１５重量％溶液を加えゲル形成の有無を観察した。結果を表５に示す。
Example 5
After adding 3.7 g (0.05 mol) of calcium hydroxide to 200 g of a mixture of isopropanol (88 wt%) and water (12 wt%) (hereinafter abbreviated as 88% IPA) and stirring and dispersing, A solution prepared by dissolving 33 g of averaged rosin (trade name: KR-614, manufactured by Arakawa Chemical Industries, Ltd., acid value 173) in 200 g of 88% IPA was added dropwise over 30 minutes under reflux. The mixture was further stirred for 4 hours under reflux, cooled, filtered, and washed with 100 g of 88% IPA. The obtained filtrate was taken out and dried under reduced pressure at 80 ° C. for 4 hours to obtain 28.8 g of white powder.
Melting point: not melted to 300 ° C. IR: 1521 cm −1 , 1414 cm −1
This was dissolved in tetrahydrofuran to prepare a 15% by weight solution.
10 g of the object to be gelled was placed in a test tube, and while stirring at room temperature, a 15% by weight solution of a tetrahydrofuran solution having the weight shown in Table 5 was added and the presence or absence of gel formation was observed. The results are shown in Table 5.
実施例６
実施例６の水酸化カルシウムに代えて水酸化バリウム・８水和物を１３．３ｇ（０．０５モル）に変えた以外は同様の操作を行い２５．１ｇの白色粉末を得た。
融点：３００℃まで溶融せず
ＩＲ：１５３６ｃｍ−１、１３９６ｃｍ−１
このものにテトラヒドロフランを加え１５重量％分散液を調製した。
ゲル化対象物１０ｇを試験管に取り、室温で攪拌しながら、表６に示した重量のテトラヒドロフラン溶液の１５重量％分散液を加えゲル形成の有無を観察した。結果を表６に示す。
Example 6
The same operation was carried out except that barium hydroxide octahydrate was changed to 13.3 g (0.05 mol) instead of calcium hydroxide in Example 6 to obtain 25.1 g of white powder.
Melting point: not melted to 300 ° C. IR: 1536 cm −1 , 1396 cm −1
Tetrahydrofuran was added to this to prepare a 15 wt% dispersion.
10 g of the gelation target was placed in a test tube, and while stirring at room temperature, a 15 wt% dispersion of a tetrahydrofuran solution having the weight shown in Table 6 was added, and the presence or absence of gel formation was observed. The results are shown in Table 6.
Claims (8)
で表される環状シロキサン化合物および／または一般式（２）：
で表されるシロキサン化合物である請求項５記載のゲル。 A siloxane compound (A) containing at least two silicon atoms is represented by the general formula (1):
A cyclic siloxane compound represented by the general formula (2):
The gel according to claim 5, which is a siloxane compound represented by the formula:
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112920426A (en) * | 2021-01-26 | 2021-06-08 | 华侨大学 | Rosinyl calcium salt supermolecule hydrogel, and preparation method and application thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112920426A (en) * | 2021-01-26 | 2021-06-08 | 华侨大学 | Rosinyl calcium salt supermolecule hydrogel, and preparation method and application thereof |
| CN112920426B (en) * | 2021-01-26 | 2023-08-29 | 华侨大学 | Rosin-based calcium salt supermolecule hydrogel, preparation method and application thereof |
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