JP4665114B2 - 珪素を基材とする第四級アンモニウム官能組成物及びこの組成物の製造方法 - Google Patents
珪素を基材とする第四級アンモニウム官能組成物及びこの組成物の製造方法 Download PDFInfo
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- JP4665114B2 JP4665114B2 JP2003538233A JP2003538233A JP4665114B2 JP 4665114 B2 JP4665114 B2 JP 4665114B2 JP 2003538233 A JP2003538233 A JP 2003538233A JP 2003538233 A JP2003538233 A JP 2003538233A JP 4665114 B2 JP4665114 B2 JP 4665114B2
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- Prior art keywords
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- hydrogen
- silicon
- monovalent hydrocarbon
- quaternary ammonium
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- 125000001453 quaternary ammonium group Chemical group 0.000 title claims abstract description 44
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title claims description 28
- 229910052710 silicon Inorganic materials 0.000 title claims description 28
- 239000010703 silicon Substances 0.000 title claims description 28
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- 239000000203 mixture Substances 0.000 title description 44
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 51
- 238000000034 method Methods 0.000 claims abstract description 29
- 150000002430 hydrocarbons Chemical group 0.000 claims description 70
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 239000000463 material Substances 0.000 claims description 27
- 150000002148 esters Chemical group 0.000 claims description 24
- -1 R 23 Chemical compound 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 21
- 125000000524 functional group Chemical group 0.000 claims description 20
- 150000002500 ions Chemical class 0.000 claims description 18
- 150000003944 halohydrins Chemical group 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 239000004215 Carbon black (E152) Substances 0.000 claims description 12
- 229930195733 hydrocarbon Natural products 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 239000004593 Epoxy Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical group O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical group OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical group OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002596 lactones Chemical class 0.000 claims description 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 150000003868 ammonium compounds Chemical class 0.000 claims 1
- 150000004756 silanes Chemical class 0.000 abstract description 11
- 239000000376 reactant Substances 0.000 description 21
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 17
- 229910000077 silane Inorganic materials 0.000 description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 125000003700 epoxy group Chemical group 0.000 description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
- PUVAFTRIIUSGLK-UHFFFAOYSA-M trimethyl(oxiran-2-ylmethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1CO1 PUVAFTRIIUSGLK-UHFFFAOYSA-M 0.000 description 14
- 150000001408 amides Chemical class 0.000 description 12
- 150000002009 diols Chemical class 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000010992 reflux Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 9
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 8
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 229920001971 elastomer Polymers 0.000 description 8
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000000518 rheometry Methods 0.000 description 5
- 150000003335 secondary amines Chemical class 0.000 description 5
- 150000003512 tertiary amines Chemical class 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 150000003141 primary amines Chemical class 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- LTVDFSLWFKLJDQ-UHFFFAOYSA-N α-tocopherolquinone Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)(O)CCC1=C(C)C(=O)C(C)=C(C)C1=O LTVDFSLWFKLJDQ-UHFFFAOYSA-N 0.000 description 3
- JTTBZVHEXMQSMM-UHFFFAOYSA-M (3-chloro-2-hydroxypropyl)-dodecyl-dimethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC(O)CCl JTTBZVHEXMQSMM-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 229920001661 Chitosan Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 150000001649 bromium compounds Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- SURLGNKAQXKNSP-DBLYXWCISA-N chlorin Chemical compound C\1=C/2\N/C(=C\C3=N/C(=C\C=4NC(/C=C\5/C=CC/1=N/5)=CC=4)/C=C3)/CC\2 SURLGNKAQXKNSP-DBLYXWCISA-N 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920002379 silicone rubber Polymers 0.000 description 2
- 239000004945 silicone rubber Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- XERREUIGCGXTDG-UHFFFAOYSA-N (3-chloro-2-hydroxypropyl)-dimethyl-octadecylazanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CC(O)CCl XERREUIGCGXTDG-UHFFFAOYSA-N 0.000 description 1
- QIKIJFUVHGOQOK-UHFFFAOYSA-M (3-chloro-2-hydroxypropyl)-dimethyl-octadecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CC(O)CCl QIKIJFUVHGOQOK-UHFFFAOYSA-M 0.000 description 1
- WHDHZGMNEDEKTC-UHFFFAOYSA-N 1-chloro-3-(dimethylamino)propan-2-ol;hydrochloride Chemical compound [Cl-].C[NH+](C)CC(O)CCl WHDHZGMNEDEKTC-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- PDCKRJPYJMCOFO-UHFFFAOYSA-N azanediyl (triplet) Chemical compound [NH] PDCKRJPYJMCOFO-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000003398 denaturant Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Silicon Polymers (AREA)
- Paints Or Removers (AREA)
Description
ここで、R21、R22、R23、R30およびR31は独立したヒドロキシあるいはフェノキシ、又はアルコキシあるいは一価の炭化水素基(特に、後者の二つの例では、炭素数20以下、好ましくは炭素数1又は2のもの);R24、R25およびR27は独立した一価の炭化水素基、特に炭素数20あるいはそれ以下の炭化水素基;R28は一価の炭化水素基、特に炭素数20あるいはそれ以下のものか、又は窒素を含み、少なくとも一部に-R1-Z-Q3の形の基あるいは複数の基が存在するものであってもよい;R26およびR29は、窒素を含み、少なくとも一部に-R1-Z-Q3の形の基あるいは複数の基が存在するもの;-R1-は、選択的にエーテル又はエステル官能基を取り入れることのできる二価の炭化水素基か、又は、-R17N(Q1)R18-、後者の場合は特に、-CH2CH(CH3)CH2-N(Q1)-CH2CH2-あるいは-(CH2)3-N(Q1)-CH2CH2-;-R17-及び-R18-は、選択的にエーテルあるいはエステル官能基を取り入れることのできる独立した二価の炭化水素基;-Q1は-CH2CH(OH)CH2N+(R4)(R5)(R6)X-、水素又は選択的にヒドロキシ、ジオール、アミド、エーテル又はエステル官能基を取り入れることのできる一価の炭化水素基;R4、R5およびR6は、独立した一価の炭化水素基;X-はカウンタイオン;-Z-は-N(Q2)-;-Q3及び-Q2は独立した-CH2CH(OH)CH2N+(R4)(R5)(R6)X-、水素あるいは選択的にヒドロキシ、ジオール、アミド、エーテル、あるいはエステル官能基を取り入れることのできる一価の炭化水素基;a、b、d、eおよびgは0より大きいか、0;
a = 0 to 2 + g;
b = 0 to 2 + g;
d = 0 to 500, 特に 0 to 400;
e = 0 to 100, 特に 0 to 50;
g = 0 to 100, 特に 0 to 5;
a + b は2より大きいか2;及びe + b > 0、ただし、当該組成物に存在するQ1、Q2、Q3の少なくとも一部、特に少なくとも10パーセント、好ましくは15〜75パーセント、より好ましくは20〜60パーセントに-CH2CH(OH)CH2N+(R4)(R5)(R6)X-が存在し、このパーセンテージは組成物中に存在するこれらの基の総数に基づく。
d = 0 to 400;
e = 0 to 50;
g = 0 to 50; および
(e + b)/(a + b + d + e + g) = 0.005 to 0.05;
ただし、組成物中のQ1、Q2およびQ3の10〜75パーセントは、-CH2CH(OH)CH2N+(R4)(R5)(R6)X-である。
d = 50 to 150;
e = 0 to 10;
g = 0 to 5; および
(e + b)/(a + b + d + e + g) = 0.01 to 0.03;
ただし、組成物中のQ1、Q2およびQ3の25〜40パーセントは、-CH2CH(OH)CH2N+(R4)(R5)(R6)X-である。
のシランである。ここで、-R11は、一価の炭化水素基又はOR41であり、ここで、-R41は水素又は一価の炭酸水素基である;R12は一価の炭化水素基もしくは-OR42であり、-R42は水素あるいは一価の炭酸水素基である;-R13は一価の炭化水素基又は-OR43であり、-R43は水素あるいは一価の炭酸水素基である;-R1-は、エーテル又はエステル官能基を選択的に取り込むことのできる二価の炭化水素基か、あるいは-R17N(Q1)18-であり;-R17-と-R18-は、エーテル又はエステル官能基を選択的に取り込むことのできる独立した二価の炭化水素基であり;-Q1は、-CH2CH(OH)CH2N+(R4)(R5)(R6)X-、水素又はヒドロキシ、ジオール、アミド、エーテルあるいはエステル官能基を選択的に取り込むことのできる一価の炭化水素基であり;R4、R5およびR6は、独立した一価の炭化水素基であり;X-はカウンタイオンである。-Z-は、-N(Q2);-Q3および-Q2は、独立して-CH2CH(OH)CH2N+(R4)(R5)(R6)X-、水素又はヒドロキシ、ジオール、アミド、エーテルあるいはエステル官能基を選択的に取り込むことのできる一価の炭化水素基である、ただし、-Q1、-Q2、及び-Q3のうち少なくとも一つが-CH2CH(OH)CH2N+(R4)(R5)(R6)X-である。
ここで、R11、R13及びR13は、独立したメトキシあるいはエポキシ基であり、R14は、アミノプロピル、アミノエチルアミノプロピル、あるいは、アミノエチルアミノイソブチル基である。
実験例
実験例1 マルチ化学量論/特性比較におけるエポキシ基の合成物
に設定した。測定器は、自動的に応力を傾けて、信号ノイズ比を適正に保つようにプログラムした。温度が100℃から50℃に下がる間に流動学的特徴を測定した。G’(貯蔵弾性率)、G”(粘稠損失弾性率)、およびη*(動的粘度)を含む定量を行った。
実験例2 ハロヒドリンとの合成
実験例3 ハロヒドリンとの合成
実験例4 アミノ末端シリコーンとの合成
実験例5 カルボキシ官能シリコーンとの合成
実験例6 第四級アンモニウム官能シランとの合成
実験例7 ジオール官能基
実験例8 アミド官能基
Claims (6)
- 基-R1-Z-Q3を有し、ここで、-R1-が、-R17N(Q1)R18-であり、独立したシリコーン中の珪素と共有結合しており;-Z-が-C(O)O-又はN(Q2)-であり;-Q3が-CH(R3)CH(OH)YN+(R4)(R5)(R6)X-、水素またはメチル、であり;-R17-は、プロピレンまたはイソブチレン基であり、-R18-は、エチレン基であり;-Q1および-Q2が、独立したCH(R3)CH(OH)YN+(R4)(R5)(R6)X-、水素、または、メチル基、であり;Yが二価の炭化水素基であり;R3が一価の炭化水素基又は水素であり;R4、R5およびR6が独立した一価の炭化水素基であり;X-がカウンタイオンであり、ただし、Q1、Q2およびQ3の少なくとも一つが-CH(R3)CH(OH)YN+(R4)(R5)(R6)X-である、珪素を基材とする第四級アンモニウム化合物、を製造する方法において、
(1)ハロヒドリン官能基を有する第四級アンモニウム化合物と、(2)有機官能基を有する珪素を基材とする物質であって、当該珪素を基材とする物質が独立したシリコーンであり、前記有機官能基がカルボキシ又はアミノ官能基を有する物質とを、反応させる工程を具えることを特徴とする方法。 - 珪素を基材とする第四級アンモニウム官能化合物において:
基-R 1 -Z-Q 3 を有し、ここで、-R 1 -が、選択的にエーテル又はエステル官能基を取り入れることができる二価の炭化水素基、または、-R 17 N(Q 1 )R 18 -であり、独立したシリコーン中の珪素と共有結合しており;-Z-が-C(O)O-又はN(Q 2 )-であり;-Q 3 が-CH(R 3 )CH(OH)YN + (R 4 )(R 5 )(R 6 )X - 、水素、または、メチル基であり;-R 17 -は、イソプロピレン、または、イソブチレン基、-R 18 -は、エチレン基であり;-Q 1 および-Q 2 が、独立したCH(R 3 )CH(OH)YN + (R 4 )(R 5 )(R 6 )X - 、水素、または、メチル基、であり;Yが二価の炭化水素基であり;R 3 が一価の炭化水素基又は水素であり;R 4 、R 5 およびR 6 が独立した一価の炭化水素基であり;X - がカウンタイオンであり、ただし、Q 1 、Q 2 およびQ 3 の少なくとも一つが-CH(R 3 )CH(OH)YN + (R 4 )(R 5 )(R 6 )X - である、珪素を基材とする第四級アンモニウム化合物において、
前記化合物が、構造:
-R 11 は、一価の炭化水素基もしくは-OR 41 であり、ここで、-R 41 は水素あるいは一価の炭酸水素基である;-R 12 は一価の炭化水素基もしくは-OR 42 であり、ここで、-R 42 は水素あるいは一価の炭酸水素基である;-R 13 は一価の炭化水素基もしくは-OR 43 であり、-R 43 は水素あるいは一価の炭酸水素基である;-R 1 -、-R 17 -及び-R 18 -は、前記に同じであり;-Q 1 は、-CH 2 CH(OH)CH 2 N + (R 4 )(R 5 )(R 6 )X - 、または、水素であり;R 4 、R 5 およびR 6 は、独立した一価の炭化水素基であり;X - はカウンタイオンであり、-Z-は、-N(Q 2 )であり;-Q 3 および-Q 2 は、独立したCH 2 CH(OH)CH 2 N + (R 4 )(R 5 )(R 6 )X - 、水素、又は、メチル基であり、ただし、-Q 1 、-Q 2 、及び-Q 3 のうち少なくとも一つが-CH 2 CH(OH)CH 2 N + (R 4 )(R 5 )(R 6 )X - である化合物において、当該化合物が、平均構造
a = 0 to 2 + g;
b = 0 to 2 + g;
d = 0 to 500;
e = 0 to 100;
g = 0 to 100;
a + b は2より大きいか、2;及び
e + b > 0、
ただし、化合物に存在する少なくともQ1、Q2、及びQ3の少なくとも一部が、-CH2CH(OH)CH2N+(R4)(R5)(R6)X-である、
前記第四級アンモニウム化合物の製造方法において、(1)置換基を有する第四級アンモニウム化合物であり、当該置換基がハロヒドリン官能基を有する化合物と、(2)有機官能基を有する珪素を基材とする物質であり、当該珪素を基材とする物質が独立したシリコーンであり、前記有機官能基がカルボキシあるいはアミノ官能基を有する物質とを反応させる工程を具えることを特徴とする方法。 - 請求項1または2に記載の方法において、前記珪素を基材とする物質がシリコーンであり、前記有機官能基がアミノ官能基であることを特徴とする方法。
- 請求項1〜3のいずれか一項に記載の方法において、前記珪素を基材とする物質がシリコーンであり、構造(X1)CH2CH(OH)YN+(R4)(R5)(R6)X-のハロヒドリン官能第四級アンモニウム化合物と反応し;ここでX1は、ハロゲンであり;Yは二価の炭化水素基であり;R4、R5及びR6は、独立した一価の炭化水素基であり、X-はカウンタイオンである、ことを特徴とする方法。
- 珪素を基材とする第四級アンモニウム官能化合物を変形する方法において、当該方法が:(1)請求項1に記載の化合物、ここで、R1の少なくとも一部が第二級アミンか、あるいはZの少なくとも一部が第一級又は第二級アミンである;と、(2)ラクトーン、カルボキシおよびエポキシからなる群から選ばれた有機官能基を有する物質T、とを反応させる工程を具えることを特徴とする方法。
- 請求項5に記載の方法において、前記物質Tがグリシドール又はガンマブチロラクトーンであることを特徴とする方法。
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KR20040058236A (ko) | 2004-07-03 |
CN1304462C (zh) | 2007-03-14 |
EP1440113A1 (en) | 2004-07-28 |
KR100926894B1 (ko) | 2009-11-17 |
BR0213623A (pt) | 2004-09-14 |
DE60222453D1 (de) | 2007-10-25 |
JP2005507016A (ja) | 2005-03-10 |
DE60222453T2 (de) | 2008-08-14 |
CN1575311A (zh) | 2005-02-02 |
US6482969B1 (en) | 2002-11-19 |
EP1440113B1 (en) | 2007-09-12 |
ATE373036T1 (de) | 2007-09-15 |
BR0213623B1 (pt) | 2012-02-22 |
WO2003035721A1 (en) | 2003-05-01 |
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