JPS63258887A - Organic silicon compound - Google Patents
Organic silicon compoundInfo
- Publication number
- JPS63258887A JPS63258887A JP62093987A JP9398787A JPS63258887A JP S63258887 A JPS63258887 A JP S63258887A JP 62093987 A JP62093987 A JP 62093987A JP 9398787 A JP9398787 A JP 9398787A JP S63258887 A JPS63258887 A JP S63258887A
- Authority
- JP
- Japan
- Prior art keywords
- caprolactam
- aminoco
- compound
- asi
- group
- 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
Links
- 150000003377 silicon compounds Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 abstract description 22
- 150000001875 compounds Chemical class 0.000 abstract description 18
- 239000004677 Nylon Substances 0.000 abstract description 4
- 229920001778 nylon Polymers 0.000 abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 abstract description 3
- 238000007334 copolymerization reaction Methods 0.000 abstract description 3
- 239000004952 Polyamide Substances 0.000 abstract description 2
- 239000006087 Silane Coupling Agent Substances 0.000 abstract description 2
- 239000003822 epoxy resin Substances 0.000 abstract description 2
- 238000006459 hydrosilylation reaction Methods 0.000 abstract description 2
- 239000011256 inorganic filler Substances 0.000 abstract description 2
- 229910003475 inorganic filler Inorganic materials 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 229920002647 polyamide Polymers 0.000 abstract description 2
- 229920000647 polyepoxide Polymers 0.000 abstract description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 238000004381 surface treatment Methods 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 238000000862 absorption spectrum Methods 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 238000002955 isolation Methods 0.000 description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 6
- -1 4- Trimethoxysilylbutyl Chemical group 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000005369 trialkoxysilyl group Chemical group 0.000 description 2
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- OZWKZRFXJPGDFM-UHFFFAOYSA-N tripropoxysilane Chemical compound CCCO[SiH](OCCC)OCCC OZWKZRFXJPGDFM-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- KZEVSDGEBAJOTK-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[5-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CC=1OC(=NN=1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O KZEVSDGEBAJOTK-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 101000913968 Ipomoea purpurea Chalcone synthase C Proteins 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 229910002666 PdCl2 Inorganic materials 0.000 description 1
- 101000907988 Petunia hybrida Chalcone-flavanone isomerase C Proteins 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- ZZHNUBIHHLQNHX-UHFFFAOYSA-N butoxysilane Chemical compound CCCCO[SiH3] ZZHNUBIHHLQNHX-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Polyamides (AREA)
Abstract
Description
【発明の詳細な説明】 七産業上の利用分野〉 本発明は新規な有機ケイ素化合物に関するものである。[Detailed description of the invention] Seven industrial application fields> The present invention relates to novel organosilicon compounds.
より詳しくは、分子内にカプロラクタム残基を有する新
規なトリアルコキシシランに関するものである。More specifically, the present invention relates to a novel trialkoxysilane having a caprolactam residue in the molecule.
〈従来の技術〉
有機官能基を有するアルコキシシランとしては、アミノ
プロピルトリメトキシシラン、エチレンジアミノプロピ
ルトリメトキシシラン、メルカプトプロピルトリメトキ
シシラン、グリシシロキシプロビルトリメトキシシラン
、ビニルトリメトキシシラン等が公知であり、そのなか
で、ビニルトリメトキシシランは、ポリオレフィンと共
重合又は、グラフト重合し、さらに温水処理してシラン
変性の橋かけポリオレフィンとなり、耐熱性、耐ストレ
スクラック性が大幅に向上することも公知である(化学
と工業 1旦、865 (1977))。<Prior art> As alkoxysilanes having an organic functional group, aminopropyltrimethoxysilane, ethylenediaminopropyltrimethoxysilane, mercaptopropyltrimethoxysilane, glycisyloxypropyltrimethoxysilane, vinyltrimethoxysilane, etc. are known. It is also known that vinyltrimethoxysilane can be copolymerized or graft-polymerized with polyolefin, and then treated with hot water to become a silane-modified cross-linked polyolefin, which greatly improves heat resistance and stress crack resistance. (Chemistry and Industry 1, 865 (1977)).
〈発明が解決しようとする問題点〉
しかしながら、ナイロンの共重合成分となり、耐熱性、
強度の向上の目的に利用できる公知な有機官能基を有す
るアルコキシシランは未だ見出されていない。<Problems to be solved by the invention> However, since it is a copolymer component of nylon, it has poor heat resistance,
An alkoxysilane having a known organic functional group that can be used for the purpose of improving strength has not yet been found.
く問題点を解決するための手段〉
本発明者らは、鋭意研究した結果、カプロラクタム残基
を有する新規なトリアルコキシシランを見出だし、本発
明に到達した。Means for Solving Problems> As a result of intensive research, the present inventors discovered a novel trialkoxysilane having a caprolactam residue, and arrived at the present invention.
すなわち、本発明は、−i式<I>で表わされる有機ケ
イ素化合物である。That is, the present invention is an organosilicon compound represented by the -i formula <I>.
[式中、R1、R2は、ASi (OR> で表わさ
れる基、水素原子もしくは、炭素原子数1〜10個の炭
化水素基を示し、かつ、R1、R2の少なくとも一方は
、A S l (OR) 3で表わされる基を示す。ま
た、ASi (OR)3で表わされる基中、Aは炭素原
子数2〜5個の、側鎖を有するかまたは有しないアルキ
レン基、Rは炭素原子数1〜4個のアルキル基を示す。[Wherein, R1 and R2 represent a group represented by ASi (OR>), a hydrogen atom, or a hydrocarbon group having 1 to 10 carbon atoms, and at least one of R1 and R2 represents ASi (OR> OR) In the group represented by ASi (OR)3, A is an alkylene group having 2 to 5 carbon atoms with or without a side chain, and R is the number of carbon atoms. Indicates 1 to 4 alkyl groups.
]ここで、Aを具体的に例示すると、
−(CH2)2−1−(CH2)3−1−(CH2)4
−5−(CH2)5−1る。Rを具体的に例示すると、
−CH3、CH’ (CH2)2CH3,
25・
CH(CH) (CH2) 3 CH3,32
・
などを挙げることができる。R,R2の具体的としては
、Asi (OR>3で表わされる基の他、水素原子、
CH3、C2H5、−CH2◎CH3などを挙げるこ
とができる。]Here, to specifically illustrate A, -(CH2)2-1-(CH2)3-1-(CH2)4
-5-(CH2)5-1. To specifically illustrate R,
-CH3, CH' (CH2)2CH3, 25・CH(CH) (CH2) 3 CH3,32
・ etc. can be mentioned. Specific examples of R and R2 include a group represented by Asi (OR>3, a hydrogen atom,
Examples include CH3, C2H5, -CH2◎CH3, and the like.
本発明の化合物を具体的に例示すれば、2−[N、N−
ビス(2−トリメトキシシリルエチlし)アミノコ−ε
−カプロラクタム、2− [N。Specific examples of the compounds of the present invention include 2-[N, N-
Bis(2-trimethoxysilylethyl)aminoco-ε
-Caprolactam, 2- [N.
N−ビス(3−トリメトキシシリルプロピル)アミノコ
−ε−カプロラクタム、2− [N、N−ビス(3−ト
リエトキシシリルプロピル)アミノコ−ε−カプロラク
タム、2− [N、N−ビス(3−トリプロポキシシリ
ルプロピル)アミノコ−ε−カプロラクタム、2−[N
、N−ビス(3−トリブトキシシリルプロビル)アミノ
コ−ε−カプロラクタム、2− [N、N−ビス(4−
トリメトキシシリルブチル)アミノコ−ε−カプロラク
タム、2− [N、N−ビス(4−トリエトキシシリル
プロル〉アミノコ−ε−カプロラクタム、2−[N、N
−ビス(5−トリメトキシシリルペンチル)アミノコ−
ε−カプロラクタム、2−[N−メチル−N−(2−)
リメトキシシリルエチル)アミノコ−ε−カプロラクタ
ム、2−[N−メチル−N−(3−トリメトキシシリル
プロピル〉アミノコ−ε−カプロラクタム、2−[N−
エチル−N−(3−)リメトキシシリルプロビル)アミ
ノコ−ε−カプロラクタム、2−[N−ブチル−N−(
3−トリメトキシシリルプロピル)アミノコ−ε−カプ
ロラクタム、2−[N−シクロヘキシル−N−(3−)
リメトキシシリルプロビル)アミノコ−ε−カプロラク
タム、2−[N−フェニル−N−(3−)リメトキシシ
リルプロビル)アミノコ−ε−カプロラクタム、2−[
N−ベンジル−N−(3−トリメトキシシリルプロピル
)アミノコ−ε−カプロラクタム、2−[N−メチル−
N−(3−)リエトキシシリルプロビル〉アミノコ−ε
−カプロラクタム、2−[N−エチル−N−<3−)リ
エトキシシリルプロビル)アミノコ−ε−カプロラクタ
ム、2−[N−ブチル−N−(3−トリエトキシシリル
プロピル)アミノコ−ε−カプロラクタム、2−[N−
フェニル−N−(3−トリエトキシシリルプロピル)ア
ミノコ−ε−カプロラクタム、2−[N−ベンジル−N
−(3−トリエトキシシリルプロピル)アミノコ−ε−
カプロラクタム、2−[N−メチル−N−(3−)リブ
トキシシリルブロピル)アミノコ−ε−カプロラクタム
、2−[N−メチル−N−(4−トリメトキシシリルブ
チル
ラクタム、2−[N−エチル−N− (4−)リメトキ
シシリルブチル)アミノコ−ε−カプロラクタム、2−
[N−ブチル−N− (4−)リメトキシシリルブチル
)アミノコ−ε−カプロラクタム、2−[N−フェニル
−N−(4−トリメトキシシリルブチル)アミノコ−ε
−カプロラクタム、2−[N−ベンジル−N− (4−
トリメトキシシリルブチル)アミノコ−ε−カプロラク
タム、2−[N−メチル−N−(4−トリエトキシシリ
ルブチル)アミノコ−ε−カプロラクタム、2−[N−
エチル−N− (4−トリエトキシシリルブチル)アミ
ノコ−ε−カプロラクタム、2−[N−ブチル−N−
(4−トリエトキシシリルブチル)アミノコ−ε−カプ
ロラクタム、2−[N−フェニル−N−(4−トリエト
キシシリルブチル)アミノコ−ε−カプロラクタム、2
−[N−ベンジル−N−(4−トリエトキシシリルブチ
ル)アミノコ−ε−カプロラクタム、2− [N−メチ
ル−N−(4−トリブトキシシリルブチル)アミノコ−
ε−カプロラクタム、2−[N−メチル−N−(5−ト
リメトキシシリルペンチル)アミノコ−ε−カプロラク
タム、2−[N−メチル−N−(5−トリエトキシシリ
ルペンチル)アミノコ−ε−カプロラクタム、2− [
N−メチル−N− (5−)リブトキシシリルペンチル
)アミノコ−ε−カプロラクタム、2− [N− (2
−)リメトキシシリルエチル)アミノコ−ε−カプロラ
クタム、2− [N− (3−トリメトキシシリルプロ
ピル)アミノコ−ε−カプロラクタム、2− [N−(
3−)リエトキシブロビル)アミノコ−ε−カプロラク
タム、2−[N− (3−トリブトキシプロピル)アミ
ノコ−ε−カプロラクタム、2− [N− (4−)リ
メトキシブチル)アミノコ−ε−カプロラクタム、2−
[N−(4−トリエトキシブチル〉アミノコ−ε−カプ
ロラクタムなどを挙げることができる。N-bis(3-trimethoxysilylpropyl)aminoco-ε-caprolactam, 2-[N,N-bis(3-triethoxysilylpropyl)aminoco-ε-caprolactam, 2-[N,N-bis(3- tripropoxysilylpropyl)aminoco-ε-caprolactam, 2-[N
, N-bis(3-tributoxysilylprobyl)aminoco-ε-caprolactam, 2-[N,N-bis(4-
trimethoxysilylbutyl)aminoco-ε-caprolactam, 2-[N,N-bis(4-triethoxysilylprol)aminoco-ε-caprolactam, 2-[N,N
-bis(5-trimethoxysilylpentyl)aminoco-
ε-caprolactam, 2-[N-methyl-N-(2-)
rimethoxysilylethyl)aminoco-ε-caprolactam, 2-[N-methyl-N-(3-trimethoxysilylpropyl)aminoco-ε-caprolactam, 2-[N-
Ethyl-N-(3-)rimethoxysilylprobyl)aminoco-ε-caprolactam, 2-[N-butyl-N-(
3-trimethoxysilylpropyl)aminoco-ε-caprolactam, 2-[N-cyclohexyl-N-(3-)
rimethoxysilylprobyl)aminoco-ε-caprolactam, 2-[N-phenyl-N-(3-)rimethoxysilylprobyl)aminoco-ε-caprolactam, 2-[
N-benzyl-N-(3-trimethoxysilylpropyl)aminoco-ε-caprolactam, 2-[N-methyl-
N-(3-)ethoxysilylprobyl>aminoco-ε
-Caprolactam, 2-[N-ethyl-N-<3-)ethoxysilylpropyl)aminoco-ε-caprolactam, 2-[N-Butyl-N-(3-triethoxysilylpropyl)aminoco-ε-caprolactam , 2-[N-
Phenyl-N-(3-triethoxysilylpropyl)aminoco-ε-caprolactam, 2-[N-benzyl-N
-(3-triethoxysilylpropyl)aminoco-ε-
Caprolactam, 2-[N-methyl-N-(3-)ributoxysilylbropyl)aminoco-ε-caprolactam, 2-[N-methyl-N-(4-trimethoxysilylbutyllactam), 2-[N- Ethyl-N-(4-)rimethoxysilylbutyl)aminoco-ε-caprolactam, 2-
[N-Butyl-N- (4-)rimethoxysilylbutyl)aminoco-ε-caprolactam, 2-[N-phenyl-N-(4-trimethoxysilylbutyl)aminoco-ε
-caprolactam, 2-[N-benzyl-N- (4-
Trimethoxysilylbutyl)aminoco-ε-caprolactam, 2-[N-methyl-N-(4-triethoxysilylbutyl)aminoco-ε-caprolactam, 2-[N-
Ethyl-N-(4-triethoxysilylbutyl)aminoco-ε-caprolactam, 2-[N-butyl-N-
(4-triethoxysilylbutyl)aminoco-ε-caprolactam, 2-[N-phenyl-N-(4-triethoxysilylbutyl)aminoco-ε-caprolactam, 2
-[N-benzyl-N-(4-triethoxysilylbutyl)aminoco-ε-caprolactam, 2-[N-methyl-N-(4-tributoxysilylbutyl)aminoco-
ε-caprolactam, 2-[N-methyl-N-(5-trimethoxysilylpentyl)aminoco-ε-caprolactam, 2-[N-methyl-N-(5-triethoxysilylpentyl)aminoco-ε-caprolactam, 2- [
N-Methyl-N-(5-)ributoxysilylpentyl)aminoco-ε-caprolactam, 2-[N-(2
-)rimethoxysilylethyl)aminoco-ε-caprolactam, 2-[N-(3-trimethoxysilylpropyl)aminoco-ε-caprolactam, 2-[N-(
3-) Liethoxybrobyl)aminoco-ε-caprolactam, 2-[N-(3-tributoxypropyl)aminoco-ε-caprolactam, 2-[N-(4-)rimethoxybutyl)aminoco-ε-caprolactam , 2-
Examples include [N-(4-triethoxybutyl)aminoco-ε-caprolactam.
本発明の化合物は任意の方法で製造することができる。The compounds of the present invention can be produced by any method.
本発明の化合物の製造法としては、例えば、−i式(I
[)で表わされる化合物[式中、R3,R4は、炭素原
子数2〜5個の、側鎖を有するかまたは有しないアルケ
ニル基、前記ASi <OR>3で表わされる基、水素
原子もしくは、炭素原子数1〜10個の炭化水素基を示
し、かつ、R3,R4の少なくとも一方は、炭素原子数
2〜5個の、側鎖を有するかまたは有しないアルクニル
基を示す。]
とトリアルコキシシランをヒドロシリル化反応させる方
法、すなわち、上記式(It)の炭素−炭素二重結合に
対して、トリアルコキシシランを付加させる方法がある
。As a method for producing the compound of the present invention, for example, -i formula (I
A compound represented by [) [wherein R3 and R4 are an alkenyl group having 2 to 5 carbon atoms with or without a side chain, a group represented by the above ASi <OR>3, a hydrogen atom, or It represents a hydrocarbon group having 1 to 10 carbon atoms, and at least one of R3 and R4 represents an alknyl group having 2 to 5 carbon atoms, with or without a side chain. ] There is a method of subjecting trialkoxysilane to a hydrosilylation reaction, that is, a method of adding trialkoxysilane to the carbon-carbon double bond of the above formula (It).
以下、この方法について具体的に説明する。This method will be specifically explained below.
本発明の化合物の製造原料として用いる、上記式(II
>で示される化合物において、上記式(I[)中、R3
,R4を具体的に例示すると、−CH=CH −C
H2CH=CH2、2・
一CH CH CH=CH2、
− C H 2C H 2C H 2C H = C
H 2、CH CH St (OCH3)3、CH
CH Si(OC2H5)3、CH CH
CH Si 、(OCH3)3、C H 2 C H
2 C H 2 S l (O C 2 H 5 )
3、CH CH CH 31 (OC3)−1
7)3、(CH ) Si (OCH3)3、(
C H 2 ) 4 S i (O C 2 H
5 ) 3、水素原子、−CH3、 C 2 H 5、
( C H 2 ) 2 C H 3、−(CH2)3
CH3、ベI)、 Ph、 CH2Ph。The above formula (II) is used as a raw material for producing the compound of the present invention.
In the compound represented by >, in the above formula (I[), R3
, R4 is specifically exemplified as -CH=CH -C
H2CH=CH2, 2. CH CH CH=CH2, - CH 2C H 2C H 2C H = C
H2, CH CH St (OCH3)3, CH
CH Si(OC2H5)3, CH CH
CH Si , (OCH3)3, C H 2 C H
2 C H 2 S l (O C 2 H 5 )
3, CH CH CH 31 (OC3)-1
7)3,(CH)Si(OCH3)3,(
C H 2 ) 4 S i (OC 2 H
5) 3, hydrogen atom, -CH3, C2H5,
(CH2)2CH3, -(CH2)3
CH3, BeI), Ph, CH2Ph.
−CH2OCH3などを挙げることができる。-CH2OCH3 and the like can be mentioned.
一方の製造原料として使用するトリアルコキシシランを
、具体的に例示すると、トリメトキシシラン、トリエト
キシシラン、トリーn−プロポキシシラン、トリーn−
ブトキシシランなどを挙げることができる。Specific examples of the trialkoxysilane used as a raw material for one production include trimethoxysilane, triethoxysilane, tri-n-propoxysilane, and tri-n-propoxysilane.
Examples include butoxysilane.
この反応では均−系及び不均一系触媒が使用できる。触
媒としては、通常、ルテニウム、ロジウム、コバルト、
ニッケル、白金、もしくはパラジウムを成分に含むもの
が用いられ、好ましい具体例としては、
RuCl (P Ph ) RuC13,23
3・
RhC1(PPh ) RhCl3.2 3
3・
Rh (CHC0CHCOCH3,)3、Co (C
o) Ni (Co) Pt/C133・
4・
Pt (’CHC0CHCOCH3)2、Pt (PP
h ) Pt (PPh3)3.34・
HPtC1・6H20、Pd/C1
Pd(PPh3)4、
P d Cl 2 (P P h 3 ) 2などを挙
げることができる。Homogeneous and heterogeneous catalysts can be used in this reaction. Catalysts usually include ruthenium, rhodium, cobalt,
Those containing nickel, platinum, or palladium as components are used, and preferred specific examples include RuCl (P Ph ) RuC13,23
3. RhCl (PPh) RhCl3.2 3
3. Rh (CHC0CHCOCH3,)3, Co (C
o) Ni (Co) Pt/C133・
4. Pt ('CHC0CHCOCH3)2, Pt (PP
h) Pt(PPh3)3.34.HPtC1.6H20, Pd/C1 Pd(PPh3)4, PdCl2(Pph3)2, and the like.
触媒の使用量は、通常、トリアルコキシシランに対して
10〜10 ’mo1%であり、好ましくは1〜10
−3mo1%である。トリアルコキシシランと前記式(
It)で表わされる化合物は必要に応じていかなる比率
(モル比)でも反応させることが可能であるが、好まし
くは1:0.5〜1:1.5(モル比〉で反応させる。The amount of catalyst used is usually 10-10'mo1%, preferably 1-10'mo1%, based on the trialkoxysilane.
-3mo1%. Trialkoxysilane and the formula (
The compounds represented by It) can be reacted at any ratio (molar ratio) as required, but preferably at a ratio of 1:0.5 to 1:1.5 (molar ratio).
反応温度は通常、−20〜250℃であり、好ましくは
0〜150℃である。反応時間は触媒使用量、反応温度
、原料モル比等により0゜1〜100時間の範囲で変え
ることが可能である。反応は常圧下又は加圧下のいずれ
でも実施することができる。The reaction temperature is usually -20 to 250°C, preferably 0 to 150°C. The reaction time can be varied within the range of 0.1 to 100 hours depending on the amount of catalyst used, reaction temperature, molar ratio of raw materials, etc. The reaction can be carried out either under normal pressure or under increased pressure.
反応溶媒は必要に応じてテトラヒドロフラン、エーテル
、ジオキサン、ベンゼン、トルエン、キシレン、ヘキサ
ン、リグロイン、石油エーテル、クロロホルム、四塩化
炭素等の非プロトン性溶媒を使用することが可能である
。As the reaction solvent, aprotic solvents such as tetrahydrofuran, ether, dioxane, benzene, toluene, xylene, hexane, ligroin, petroleum ether, chloroform, and carbon tetrachloride can be used as necessary.
また、他の合成法としては、−ffi式(I[I)で表
わされる化合物
[式中、R5は、水素原子もしくは、アルキル基、アラ
ルキル基またはトリアルコキシシリル基を示す。]
とハロアルキルトリアルコキシシランを置換反応させる
方法も挙げられる。Further, as another synthesis method, a compound represented by the -ffi formula (I[I) [wherein R5 represents a hydrogen atom, an alkyl group, an aralkyl group, or a trialkoxysilyl group]. ] and a haloalkyltrialkoxysilane may be subjected to a substitution reaction.
かくして得られた反応混合物から本発明化合物を、単離
する方法は常法によることができ、例えばクロマトグラ
フィー等により目的物を単離、精製することができる。The compound of the present invention can be isolated from the reaction mixture thus obtained by a conventional method. For example, the target compound can be isolated and purified by chromatography or the like.
かくして得られた本発明の有機ケイ素化合物は新規な化
合物であり、常温付近では極めて流動性が低く、無色な
いしは、褐色を帯びた液状物質である。The organosilicon compound of the present invention thus obtained is a novel compound, and has extremely low fluidity near room temperature, and is a colorless or brownish liquid substance.
く作用〉
本発明の化合物は、分子内にトリアルコキシシリル基、
アミノ基、アミド基を同時に有している新規な化合物で
あり、新規なカプロラクタムの共重合成分として利用で
きる。Effect> The compound of the present invention has a trialkoxysilyl group in the molecule,
This is a new compound that simultaneously has an amino group and an amide group, and can be used as a new copolymerization component for caprolactam.
〈実施例〉
以下の実施例によって本発明の化合物を具体的に説明す
るが、以下の実施例は本発明の一部の例について説明す
るものであり、特許請求の範囲を限定するものでない。<Examples> The compounds of the present invention will be specifically explained using the following examples. However, the following examples explain some examples of the present invention and do not limit the scope of the claims.
実施例1
2−(N−メチル−N−アリルアミノ)−ε−カプロラ
クタム20gをテトラヒドロフラン31.61gとトリ
メトキシシラン(純度93゜7%>28.62gの混合
物に溶かし、塩化白金酸(6水塩)1gをイソプロピル
アルコール(50g)に溶かして調製した塩化白金酸の
イソプロピルアルコール溶液278μlを加えて、反応
温度を80℃に保って8時間加熱、反応させた。反応後
、低沸点留分を留去して、残留物をカラムクロマトグラ
フィー(メルク社、Aluminiumoxid 6
0G neutral Art、1090;展開溶
媒 酢酸エチル)で単離精製を行い30.226gの生
成物を得た。Example 1 20 g of 2-(N-methyl-N-allylamino)-ε-caprolactam was dissolved in a mixture of 31.61 g of tetrahydrofuran and 28.62 g of trimethoxysilane (purity 93°7%> 278 μl of an isopropyl alcohol solution of chloroplatinic acid prepared by dissolving 1 g of ) in isopropyl alcohol (50 g) was added, and the reaction temperature was kept at 80°C and heated for 8 hours. After the reaction, the low boiling point fraction was distilled. The residue was subjected to column chromatography (Merck, Aluminum Oxide 6).
Isolation and purification was performed using 0G neutral Art, 1090; developing solvent ethyl acetate) to obtain 30.226 g of product.
得られた生成物の赤外線吸収スペクトル、核磁気共鳴ス
ペクトル、元素分析結果を第1表に示す。Table 1 shows the infrared absorption spectrum, nuclear magnetic resonance spectrum, and elemental analysis results of the obtained product.
以上のデータより得られた生成物は 2−[N−メチル
−N−(3−)リメトキシシリルプロピル)アミノコ−
ε−カプロラクタム であると確認した。The product obtained from the above data is 2-[N-methyl-N-(3-)rimethoxysilylpropyl)aminoco-
It was confirmed to be ε-caprolactam.
実施例2
2−(N−メチル−N−アリルアミノ)−ε−カプロラ
クタム2gをテトラヒドロフラン3gとトリエトキシシ
ラン7.21gの混合物に溶かし、実施例1で使用した
のと同じ塩化白金酸のイソプロピルアルコール溶液55
.6μlを加えて、加熱、反応させた。反応後、実施例
1と同様の方法で単離精製を行い3.68gの生成物を
得た。Example 2 2 g of 2-(N-methyl-N-allylamino)-ε-caprolactam was dissolved in a mixture of 3 g of tetrahydrofuran and 7.21 g of triethoxysilane, and the same isopropyl alcohol solution of chloroplatinic acid used in Example 1 was prepared. 55
.. 6 μl was added, heated, and reacted. After the reaction, isolation and purification were performed in the same manner as in Example 1 to obtain 3.68 g of product.
得られた生成物の赤外線吸収スペクトル、核磁気共鳴ス
ペクトル、元素分析結果を第1表に示す。Table 1 shows the infrared absorption spectrum, nuclear magnetic resonance spectrum, and elemental analysis results of the obtained product.
以上のデータより得られた生成物は2− [N−メチル
−N−(3−)リエトキシシリルブロピル)アミノコ−
ε−カプロラクタムであると確認した。The product obtained from the above data is 2-[N-methyl-N-(3-)ethoxysilylpropyl)aminoco-
It was confirmed to be ε-caprolactam.
実施例3
2−(N−n−ブチル−N−アリルアミノ)−ε−カプ
ロラクタム2gをテトラヒドロフラン2gとトリメトキ
シシラン(純度93.7%)4.65gの混合物に溶か
し、実施例1で使用したのと同じ塩化白金酸のイソプロ
ピルアルコール溶液45.1μlを加えて、加熱、反応
させた。反応後、実施例1と同様の方法で単離精製を行
い2.792gの生成物を得た。Example 3 2 g of 2-(N-n-butyl-N-allylamino)-ε-caprolactam was dissolved in a mixture of 2 g of tetrahydrofuran and 4.65 g of trimethoxysilane (purity 93.7%) to prepare the same solution as used in Example 1. 45.1 μl of the same isopropyl alcohol solution of chloroplatinic acid was added, and the mixture was heated and reacted. After the reaction, isolation and purification were performed in the same manner as in Example 1 to obtain 2.792 g of product.
得られた生成物の赤外線吸収スペクトル、核磁気共鳴ス
ペクトル、元素分析結果を第1表に示す。Table 1 shows the infrared absorption spectrum, nuclear magnetic resonance spectrum, and elemental analysis results of the obtained product.
以上のデータより得られた生成物は2−[N−n−ブチ
ル−N−(3−トリメトキシシリルプロピル)アミノコ
−ε−カプロラクタムであると確認しな。The product obtained from the above data was confirmed to be 2-[N-n-butyl-N-(3-trimethoxysilylpropyl)aminoco-ε-caprolactam.
実施例4
2−(N−ベンジル−N−アリルアミノ)−εニオプロ
ラクタム2gをテトラヒドロフラン4gとトリメトキシ
シラン(純度93.7%)3.784gの混合物に溶か
し、実施例1で使用したのと同じ塩化白金酸のイソプロ
ピルアルコール溶液39.2μlを加えて、加熱、反応
させた。反応後、実施例1と同様の方法で単離精製を行
い2.74gの生成物を得た。Example 4 2 g of 2-(N-benzyl-N-allylamino)-ε nioprolactam as used in Example 1 was dissolved in a mixture of 4 g of tetrahydrofuran and 3.784 g of trimethoxysilane (93.7% purity). 39.2 μl of the same isopropyl alcohol solution of chloroplatinic acid was added, and the mixture was heated and reacted. After the reaction, isolation and purification were performed in the same manner as in Example 1 to obtain 2.74 g of product.
得られた生成物の赤外線吸収スペクトル、核磁気共鳴ス
ペクトル、元素分析結果を第1表に示す。Table 1 shows the infrared absorption spectrum, nuclear magnetic resonance spectrum, and elemental analysis results of the obtained product.
以上のデータより得られた生成物は2−[N−ベンジル
−N−(3−)リメトキシシリルブロピル)アミノコ−
ε−カプロラクタムであると確認した。The product obtained from the above data is 2-[N-benzyl-N-(3-)rimethoxysilylbropyl)aminoco-
It was confirmed to be ε-caprolactam.
実施例5
2−(N−メチル−N−ホモアリルアミノ)−ε−カプ
ロラクタム2gとトリメトキシシラン(純度 93.7
%)4.980gの混合物に溶かし、実施例1で使用し
たのと同じ塩化白金酸のイソプロピルアルコール溶液5
1.6μlを加えて、加熱、反応させた。反応後、実施
例1と同様の方法で単離精製を行い3.002gの生成
物を得た。Example 5 2-(N-methyl-N-homoallylamino)-ε-caprolactam and trimethoxysilane (purity 93.7
%) of the same isopropyl alcohol solution of chloroplatinic acid as used in Example 1, dissolved in a mixture of 4.980 g and 5
1.6 μl was added, heated, and reacted. After the reaction, isolation and purification were performed in the same manner as in Example 1 to obtain 3.002 g of product.
得られた生成物の赤外線吸収スペクトル、核磁気共鳴ス
ペクトル、元素分析結果を第1表に示す。Table 1 shows the infrared absorption spectrum, nuclear magnetic resonance spectrum, and elemental analysis results of the obtained product.
以上のデータより得られた生成物は2−[N−メチル−
N−<3−)リメトキシシリルブチル)アミノコ−ε−
カプロラクタムであると確認した。The product obtained from the above data is 2-[N-methyl-
N-<3-)rimethoxysilylbutyl)aminoco-ε-
It was confirmed to be caprolactam.
実施例6
2− (N、N−ジアリルアミノ)−ε−カプロラクタ
ム2gをテトラヒドロフラン3.19gとトリメトキシ
シラン(純度93.7%)15.026gの混合物に溶
かし、実施例1で使用したのと同じ塩化白金酸のイソプ
ロピルアルコール溶液49μlを加えて、加熱、反応さ
せた。反応後、実施例1と同様の方法で単離精製を行い
2.933gの生成物を得た。Example 6 2 g of 2-(N,N-diallylamino)-ε-caprolactam was dissolved in a mixture of 3.19 g of tetrahydrofuran and 15.026 g of trimethoxysilane (purity 93.7%) and mixed with the same solution as used in Example 1. 49 μl of the same isopropyl alcohol solution of chloroplatinic acid was added, and the mixture was heated and reacted. After the reaction, isolation and purification were performed in the same manner as in Example 1 to obtain 2.933 g of product.
得られた生成物の赤外線吸収スペクトル、核磁気共鳴ス
ペクトル、元素分析結果を第1表に示す。Table 1 shows the infrared absorption spectrum, nuclear magnetic resonance spectrum, and elemental analysis results of the obtained product.
以上のデータより得られた生成物は2− [N。The product obtained from the above data is 2-[N.
N−ビス(3−トリメトキシシリルプロピル)アミノコ
−ε−カプロラクタムであると確認した。It was confirmed to be N-bis(3-trimethoxysilylpropyl)aminoco-ε-caprolactam.
参考例
ε−カプロラクタムを20gずつ、2本の試験管(以下
、それぞれを、試験管a、試験管すと称する〉に加え、
130℃で加熱融解し、脱気・Ar置換を10分間行っ
た。さらにもう1本の試験管(以下、試験管Cと称する
)に実施例1で得られた2−[N−メチル−N−(3−
トリメトキシシリルプロピル)アミノコ−ε−カプロラ
クタム(純度100%)2.15g。Reference Example Add 20g of ε-caprolactam to two test tubes (hereinafter referred to as test tube a and test tube),
It was heated and melted at 130°C, and degassed and replaced with Ar for 10 minutes. Furthermore, in another test tube (hereinafter referred to as test tube C), the 2-[N-methyl-N-(3-
2.15 g of trimethoxysilylpropyl)aminoco-ε-caprolactam (100% purity).
ヘキサメチレン−1,6−ピスカルバミドカプロラクタ
ム1.395gを添加しAr置換した。1.395 g of hexamethylene-1,6-piscarbamide caprolactam was added and the mixture was replaced with Ar.
試験管aの内容物を試験管Cに加え、試験管すにナトリ
ウム0.08gを添加し、試験管すの内容物を試験管C
に加え、よく振とうして150℃に保つと、2分以内に
固化し、完全に重合させるためにさらに30分間150
℃に保って、ε−カプロラクタムと2− [N−メチフ
レーN−く3−トリメトキシシリルプロピル)アミノコ
−ε−カプロラクタムの共重合体を得た。Add the contents of test tube A to test tube C, add 0.08 g of sodium to the test tube, and transfer the contents of test tube A to test tube C.
When added to the solution and shaken well and kept at 150°C, it solidified within 2 minutes and was heated at 150°C for an additional 30 minutes to ensure complete polymerization.
C. to obtain a copolymer of .epsilon.-caprolactam and 2-[N-methifle-N-3-trimethoxysilylpropyl)aminoco-.epsilon.-caprolactam.
共重合体のケイ素含有量は、0.52%(理論値0.5
2%)であった。The silicon content of the copolymer is 0.52% (theoretical value 0.5
2%).
〈発明の効果〉
本発明の化合物は新規な化合物であり、新規なカプロラ
クタム残基を有する有機ケイ素化合物として、ナイロン
の共重合成分に利用でき、ナイロンの改質、特に、耐熱
性、強度の向上が可能である。また、新規なシランカッ
プリング剤として、各種材料、無機フィラー、ポリアミ
ド、エポキシ樹脂等の、表面処理剤として利用できる。<Effects of the Invention> The compound of the present invention is a novel compound, and as a novel organosilicon compound having a caprolactam residue, it can be used as a copolymerization component of nylon, and is useful for modifying nylon, particularly improving heat resistance and strength. is possible. In addition, it can be used as a novel silane coupling agent and as a surface treatment agent for various materials, inorganic fillers, polyamides, epoxy resins, etc.
第1図および第2図は、実施例2で合成した本発明化合
物である2−[N−メチル−N−(3−トリエトキシシ
リルプロピル)アミノコ−ε−カプロラクタムの赤外線
吸収スペクトルのチャートおよび核磁気共鳴スペクトル
のチャートをそれぞれ示す。Figures 1 and 2 show the infrared absorption spectrum chart and nuclear spectrum of 2-[N-methyl-N-(3-triethoxysilylpropyl)aminoco-ε-caprolactam, the compound of the present invention synthesized in Example 2. Charts of magnetic resonance spectra are shown.
Claims (1)
される基、水素原子もしくは、炭素原子数1〜10個の
炭化水素基を示し、かつ、R^1、R^2の少なくとも
一方は、ASi(OR)_3で表わされる基を示す。ま
た、ASi(OR)_3で表わされる基中、Aは炭素原
子数2〜5個の、側鎖を有するかまたは有しないアルキ
レン基、Rは炭素原子数1〜4個のアルキル基を示す。 ][Claims] An organosilicon compound represented by general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I) [In the formula, R^1 and R^2 are a group represented by ASi(OR)_3, a hydrogen atom, or a group having 1 to 10 carbon atoms. It represents a hydrocarbon group, and at least one of R^1 and R^2 represents a group represented by ASi(OR)_3. In the group represented by ASi(OR)_3, A represents an alkylene group having 2 to 5 carbon atoms, with or without a side chain, and R represents an alkyl group having 1 to 4 carbon atoms. ]
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP62093987A JPS63258887A (en) | 1987-04-16 | 1987-04-16 | Organic silicon compound |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP62093987A JPS63258887A (en) | 1987-04-16 | 1987-04-16 | Organic silicon compound |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS63258887A true JPS63258887A (en) | 1988-10-26 |
Family
ID=14097751
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP62093987A Pending JPS63258887A (en) | 1987-04-16 | 1987-04-16 | Organic silicon compound |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS63258887A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113185690A (en) * | 2021-06-30 | 2021-07-30 | 东营大莱智能科技有限公司 | Process for preparing high-fluidity polyamide |
-
1987
- 1987-04-16 JP JP62093987A patent/JPS63258887A/en active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113185690A (en) * | 2021-06-30 | 2021-07-30 | 东营大莱智能科技有限公司 | Process for preparing high-fluidity polyamide |
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