JP2938789B2 - Method for preventing coloration or discoloration of amino group-containing organosilicon compound - Google Patents
Method for preventing coloration or discoloration of amino group-containing organosilicon compoundInfo
- Publication number
- JP2938789B2 JP2938789B2 JP7210615A JP21061595A JP2938789B2 JP 2938789 B2 JP2938789 B2 JP 2938789B2 JP 7210615 A JP7210615 A JP 7210615A JP 21061595 A JP21061595 A JP 21061595A JP 2938789 B2 JP2938789 B2 JP 2938789B2
- Authority
- JP
- Japan
- Prior art keywords
- amino group
- discoloration
- compound
- group
- containing organosilicon
- 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.)
- Expired - Lifetime
Links
- 125000003277 amino group Chemical group 0.000 title claims description 20
- 150000003961 organosilicon compounds Chemical class 0.000 title claims description 15
- 238000002845 discoloration Methods 0.000 title claims description 9
- 238000000034 method Methods 0.000 title description 5
- -1 alcohol compound Chemical class 0.000 claims description 17
- 238000004040 coloring Methods 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 150000002430 hydrocarbons Chemical group 0.000 claims 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000005498 polishing Methods 0.000 description 2
- 150000003377 silicon compounds Chemical class 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- WFSMVVDJSNMRAR-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethanol Chemical compound CCOCCOCCOCCO WFSMVVDJSNMRAR-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- QHQNYHZHLAAHRW-UHFFFAOYSA-N 2-trimethoxysilylethanamine Chemical compound CO[Si](OC)(OC)CCN QHQNYHZHLAAHRW-UHFFFAOYSA-N 0.000 description 1
- ZYAASQNKCWTPKI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propan-1-amine Chemical compound CO[Si](C)(OC)CCCN ZYAASQNKCWTPKI-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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- KIUCLRQNNKHLDB-UHFFFAOYSA-N [dimethoxy(methyl)silyl]methanamine Chemical compound CO[Si](C)(CN)OC KIUCLRQNNKHLDB-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004649 discoloration prevention Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005183 environmental health Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- TUEYHEWXYWCDHA-UHFFFAOYSA-N ethyl 5-methylthiadiazole-4-carboxylate Chemical compound CCOC(=O)C=1N=NSC=1C TUEYHEWXYWCDHA-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000007774 longterm 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
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- YZPARGTXKUIJLJ-UHFFFAOYSA-N n-[3-[dimethoxy(methyl)silyl]propyl]aniline Chemical compound CO[Si](C)(OC)CCCNC1=CC=CC=C1 YZPARGTXKUIJLJ-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 150000003284 rhodium compounds Chemical class 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- ARKBFSWVHXKMSD-UHFFFAOYSA-N trimethoxysilylmethanamine Chemical compound CO[Si](CN)(OC)OC ARKBFSWVHXKMSD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C25/00—Surface treatment of fibres or filaments made from glass, minerals or slags
- C03C25/10—Coating
- C03C25/24—Coatings containing organic materials
- C03C25/40—Organo-silicon compounds
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Geochemistry & Mineralogy (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Silicon Polymers (AREA)
Description
【０００１】[0001]
【発明の技術分野】本発明は、アミノ基含有有機ケイ素
化合物にアルコール化合物を添加することにより、アミ
ノ基含有有機ケイ素化合物の着色ないしは変色を防止す
る方法に関するものであり、本発明により得られるアミ
ノ基含有有機ケイ素化合物はガラス繊維処理剤あるいは
艶出し用添加剤として好適に用いられる。BACKGROUND OF THE INVENTION The present invention relates to an amino group-containing organosilicon compound, which comprises adding an alcohol compound to the compound.
To prevent coloration or discoloration of organosilicon compounds containing
The method according to the present invention.
The organosilicon compound containing a group is suitably used as a glass fiber treating agent or an additive for polishing.
【０００２】[0002]
【発明の技術的背景とその問題点】アミノ基含有シラン
又はシロキサンは、ガラス繊維処理剤あるいは艶出し用
添加剤等として有用な化合物であるが、これらの化合物
は保存中にアミノ基が酸化され、得ようとする目的物が
着色ないしは変色を起こすという不利がある。そのた
め、着色又は変色を防止するためには、アミノ基含有シ
ラン又はシロキサンの製造を窒素ガス、アルゴンガス等
の不活性ガスの雰囲気中で行うことが考えられるが、特
殊な設備が必要となってしまうことから、一般的には困
難である。特開昭５３−５１２４号公報では、上記のよ
うに該化合物の製造に際して、メルカプト基含有化合物
を添加することにより改善が提案されているが、メルカ
プト基含有化合物が比較的高価であることから、工業的
な解決手段とは言えない。BACKGROUND OF THE INVENTION Amino group-containing silanes or siloxanes are useful compounds as glass fiber treating agents or polishing additives, but these compounds are oxidized during storage. However, there is a disadvantage that the object to be obtained is colored or discolored. Therefore, in order to prevent coloring or discoloration, production of amino group-containing silane or siloxane may be performed in an atmosphere of an inert gas such as nitrogen gas or argon gas, but special equipment is required. This is generally difficult. JP-A-53-5124 proposes an improvement by adding a mercapto group-containing compound during the production of the compound as described above. However, since the mercapto group-containing compound is relatively expensive, It is not an industrial solution.
【０００３】[0003]
【発明の目的】本発明は、より安価に、アミノ基含有有
機ケイ素化合物の着色ないしは変色を防止する方法を提
供することを目的とする。SUMMARY OF THE INVENTION An object of the present invention is to provide a method for preventing coloring or discoloration of an amino group-containing organosilicon compound at a lower cost.
【０００４】[0004]
【発明の構成】本発明者らは、上記目的を達成すべく鋭
意検討した結果、特定のアルコール化合物の添加が極め
て有効であることを見出し、本発明を完成するに至っ
た。即ち本発明は、アミノ基含有有機ケイ素化合物100
重量部に対して、 式 RO(CmH2mO)nH (1) （式中、R は炭素原子数１〜20の一価の炭化水素基、ｍ
は１〜10の数、ｎは０〜20の数）で示されるアルコール
化合物0.001 〜10重量部を添加することを特徴とするア
ミノ基含有有機ケイ素化合物の着色ないし変色防止方法
である。 The present inventors have conducted intensive studies to achieve the above object, and as a result, have found that the addition of a specific alcohol compound is extremely effective, and completed the present invention. That is, the present invention provides an amino group-containing organosilicon compound 100
Parts by weight are represented by the formula RO (C m H 2m O) n H (1) (where R is a monovalent hydrocarbon group having 1 to 20 carbon atoms, m
A to the number of 1 to 10, n is characterized by adding an alcohol compound from 0.001 to 10 parts by weight represented by the number of 0 to 20)
Method for preventing discoloration or discoloration of amino-containing organosilicon compounds
It is.
【０００５】以下、本発明について詳細に説明する。本
発明においてアミノ基含有有機ケイ素化合物としては、
１分子中にアミノ基を少なくとも１個有するものであれ
ば、従来から知られている種々のものが使用でき、この
ようなものとして、例えば、Hereinafter, the present invention will be described in detail. In the present invention, as the amino group-containing organosilicon compound,
As long as it has at least one amino group in one molecule, various conventionally known ones can be used.
【０００６】[0006]
【化１】 Embedded image
【０００７】で示されるシロキシ単位を有するアミノ基
含有シランまたはアミノ基含有シロキサンが例示され
る。該(2) 式中、Ｚは水素原子、フェニル基又は式An amino group-containing silane or amino group-containing siloxane having a siloxy unit represented by the following formula: In the formula (2), Z represents a hydrogen atom, a phenyl group or a formula
【０００８】[0008]
【化２】 Embedded image
【０００９】（ここにｅは１〜10の整数）で示される基
であり、R1は炭素原子数１〜６の二価炭化水素基、R2は
炭素原子数１〜８の一価炭化水素基、Y は水酸基又は炭
素原子数１〜６のアルコキシ基、ｃは０、１または２、
ｄは０、１、２または３、ただし０≦ｃ＋ｄ≦３であ
る。その他のシロキサン単位としては、下記式(3) で示
されるものが例示される。 R3SiO(4-k)/2 (3) ここで、R3は炭素原子数１〜８の一価炭化水素基、ｋは
０、１、２または３である。このようなアミノ基含有シ
ランとしては、具体的には、３−アミノプロピルトリメ
トキシシラン、３−アミノプロピルトリエトキシシラ
ン、Ｎ−アミノエチル−３−アミノプロピルトリメトキ
シシラン、３−アミノプロピルメチルジメトキシシラ
ン、Ｎ−アミノエチル−３−アミノプロピルメチルジメ
トキシシラン、アミノメチルトリメトキシシラン、アミ
ノエチルトリメトキシシラン、アミノメチル・メチルジ
メトキシシラン、Ｎ−フェニル−３−アミノプロピルメ
チルジメトキシシラン等が例示される。またアミノ基含
有シロキサンとしては、下記式で示されるようなものが
例示され、これらの分子構造は環状、鎖状または分枝鎖
状のいずれであってもよい。(Where e is an integer of 1 to 10), R 1 is a divalent hydrocarbon group having 1 to 6 carbon atoms, and R 2 is a monovalent hydrocarbon group having 1 to 8 carbon atoms. A hydrogen group, Y is a hydroxyl group or an alkoxy group having 1 to 6 carbon atoms, c is 0, 1 or 2,
d is 0, 1, 2 or 3, provided that 0 ≦ c + d ≦ 3. Examples of other siloxane units include those represented by the following formula (3). R 3 SiO (4-k) / 2 (3) Here, R 3 is a monovalent hydrocarbon group having 1 to 8 carbon atoms, and k is 0, 1, 2, or 3. Specific examples of such an amino group-containing silane include 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-aminoethyl-3-aminopropyltrimethoxysilane, and 3-aminopropylmethyldimethoxysilane. Examples include silane, N-aminoethyl-3-aminopropylmethyldimethoxysilane, aminomethyltrimethoxysilane, aminoethyltrimethoxysilane, aminomethylmethyldimethoxysilane, N-phenyl-3-aminopropylmethyldimethoxysilane, and the like. . Examples of the amino group-containing siloxane include those represented by the following formulas, and their molecular structures may be any of cyclic, linear, and branched.
【００１０】[0010]
【化３】 Embedded image
【００１１】次に、本発明において使用されるアルコー
ル化合物は、上記した式(1) で示されるもので、式中、
R は、メチル基、エチル基、プロピル基、ブチル基、ヘ
キシル基、フェニル基等の炭素原子数１〜20の一価の炭
化水素基であり、ｍは１〜10の数、ｎは０〜20の数であ
る。良好な特性が得られることから、R は炭素原子数１
〜８の一価の炭化水素基、特にメチル基、エチル基が好
ましい。また、ｎは１〜８、特に２〜４の数であること
が好ましい。このようなアルコール化合物としては、メ
タノール、エタノール、プロパノール、ブタノール等の
アルコール、エチレングリコールモノメチルエーテル、
エチレングリコールモノエチルエーテル、プロピレング
リコールモノメチルエーテル、プロピレングリコールモ
ノエチルエーテル、ジエチレングリコールモノメチルエ
ーテル、ジエチレングリコールモノエチルエーテル、ト
リエチレングリコールモノメチルエーテル、トリエチレ
ングリコールモノエチルエーテル、テトラエチレングリ
コールモノメチルエーテル、テトラエチレングリコール
モノエチルエーテル等の（ポリ）アルキレングリコール
モノアルキルエーテルなどが例示され、中でも効果が良
好に維持されることから（ポリ）アルキレングリコール
モノアルキルエーテルが好ましく、特にジアルキレング
リコールモノアルキルエーテルが好ましい。Next, the alcohol compound used in the present invention is represented by the above formula (1).
R is a monovalent hydrocarbon group having 1 to 20 carbon atoms such as a methyl group, an ethyl group, a propyl group, a butyl group, a hexyl group, and a phenyl group; m is a number of 1 to 10; The number is twenty. Since good characteristics can be obtained, R has 1 carbon atom.
~ 8 monovalent hydrocarbon groups, particularly methyl and ethyl groups are preferred. Further, n is preferably a number of 1 to 8, particularly preferably 2 to 4. Examples of such alcohol compounds include alcohols such as methanol, ethanol, propanol and butanol, ethylene glycol monomethyl ether,
Ethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, tetraethylene glycol monomethyl ether, tetraethylene glycol monoethyl Examples thereof include (poly) alkylene glycol monoalkyl ethers such as ethers. Among them, (poly) alkylene glycol monoalkyl ethers are preferable, and dialkylene glycol monoalkyl ethers are particularly preferable, since the effect is favorably maintained.
【００１２】本発明のアミノ基含有有機ケイ素化合物の
着色ないし変色防止方法は、例えば、アミノ基含有有機
ケイ素化合物と、上記した式(1) で示されるアルコール
化合物とを、常温下で、均一に混合することにより実施
されるが、両者の配合割合については、アミノ基含有有
機ケイ素化合物100 重量部に対して、アルコール化合物
0.001 〜10重量部の範囲が必要である。アルコール化合
物の添加量が0.001 重量部未満では、本発明の目的であ
るアミノ基含有有機ケイ素化合物の変色又は着色を十分
に防止することができず、また10重量部を越えると、ア
ルコール化合物特有の臭気が発生してしまい、環境衛生
上不都合をきたしてしまうこととなる。The amino group-containing organosilicon compound of the present invention
Coloring or discoloration prevention method is carried out, for example, an amino group-containing organic silicon compound, an alcohol compound represented by the formula (1) described above, at ambient temperature, by homogeneously mixing
However , the mixing ratio of the two is based on 100 parts by weight of the amino group-containing organosilicon compound and the alcohol compound.
A range of 0.001 to 10 parts by weight is required . When the addition amount of the alcohol compound is less than 0.001 part by weight, the discoloration or coloring of the amino group-containing organosilicon compound, which is the object of the present invention, cannot be sufficiently prevented. An odor is generated, which causes environmental health problems.
【００１３】また、アルコール化合物は、アミノ基含有
有機ケイ素化合物を合成する段階で配合してもよく、例
えばアリルアミンとポリオルガノハイドロジェンシロキ
サンのロジウム化合物などを触媒とする付加反応による
合成や、アミノ基含有アルコキシシランとジオルガノシ
ロキサンとの平衡化反応による合成などにおいて配合し
てもよい。上記のようにしてアミノ基含有有機ケイ素化
合物に、アルコール化合物を添加配合してなる組成物
は、長期間の保存においても、全く着色若しくは変色す
るおそれのない有機ケイ素化合物系組成物となる。[0013] Also, an alcohol compound may be blended at the stage of synthesizing the amino group-containing organic silicon compound, for example, synthetic or rhodium compound allylamine polyorganohydrogensiloxane and by addition reaction of the catalyst, the amino You may mix | blend in synthesis | combination by the equilibrium reaction of group-containing alkoxysilane and diorganosiloxane. The composition obtained by adding the alcohol compound to the amino group-containing organosilicon compound as described above is an organosilicon compound-based composition that does not have any risk of coloring or discoloration even during long-term storage.
【００１４】[0014]
【実施例】以下、実施例及び比較例を用いて本発明を更
に詳しく説明する。ただし、本発明はこれらに限定され
るものではない。 実施例１The present invention will be described below in more detail with reference to Examples and Comparative Examples. However, the present invention is not limited to these. Example 1
【００１５】[0015]
【化４】 Embedded image
【００１６】で表されるアミノ基含有オルガノポリシロ
キサン（シロキサンＡ）100 重量部に対し式C2H5OHで表
されるアルコール化合物Ｂを２重量部添加混合し、その
後、室温で２週間放置し、外観の着色度を観察したが、
淡黄色透明のまま変化はなかった。 実施例２ 実施例１で用いたシロキサンＡ 100 重量部に対し式C2
H5(OCH2CH2)OH で表されるアルコール化合物Ｃを２重量
部添加混合し、その後、室温で２週間放置し、外観の着
色度を観察したが、淡黄色透明のまま変化はなかった。 比較例１ 実施例１で用いたシロキサンＡに何も添加せずに、室温
で２週間放置し、外観の着色度を観察したところ、白濁
した。 比較例２ 実施例１で用いたシロキサンＡ 100 重量部に対し式HO
C2H4OHで表される化合物Ｄを２重量部添加混合し、その
後、室温で２週間放置し、外観の着色度を観察したとこ
ろ、白濁した。 実施例３ 実施例１で用いたシロキサンＡ 100 重量部に対し式C2
H5(OCH2CH2)2OHで表されるアルコール化合物Ｅを２重量
部添加混合し、その後、室温で２週間放置し、外観の着
色度を観察したが、淡黄色透明のまま変化はなかった。 実施例４ 実施例１で用いたシロキサンＡ 100 重量部に対し式2 parts by weight of the alcohol compound B represented by the formula C 2 H 5 OH is added to 100 parts by weight of the amino group-containing organopolysiloxane (siloxane A) represented by the formula (1), and then left at room temperature for 2 weeks. And observed the degree of coloring of the appearance,
There was no change in light yellow and transparent. Example 2 The formula C 2 was added to 100 parts by weight of the siloxane A used in Example 1.
2 parts by weight of an alcohol compound C represented by H 5 (OCH 2 CH 2 ) OH was added and mixed, and then allowed to stand at room temperature for 2 weeks to observe the degree of coloring of the appearance. Was. Comparative Example 1 The siloxane A used in Example 1 was left at room temperature for 2 weeks without adding anything, and the degree of coloration of the appearance was observed. Comparative Example 2 The formula HO was used with respect to 100 parts by weight of the siloxane A used in Example 1.
2 parts by weight of a compound D represented by C 2 H 4 OH was added and mixed, and the mixture was allowed to stand at room temperature for 2 weeks. Example 3 The formula C 2 was added to 100 parts by weight of the siloxane A used in Example 1.
2 parts by weight of an alcohol compound E represented by H 5 (OCH 2 CH 2 ) 2 OH was added and mixed, and then allowed to stand at room temperature for 2 weeks to observe the coloring degree of the appearance. Did not. Example 4 The formula was applied to 100 parts by weight of the siloxane A used in Example 1.
【００１７】[0017]
【化５】 Embedded image
【００１８】で表されるアルコール化合物Ｆを２重量部
添加混合し、その後、室温で２週間放置し、外観の着色
度を観察したが、淡黄色透明のまま変化はなかった。2 parts by weight of the alcohol compound F represented by the formula was added and mixed, and the mixture was allowed to stand at room temperature for 2 weeks, and the degree of coloration of the appearance was observed.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 ＦＩ Ｃ０９Ｄ 183/08 Ｃ０９Ｄ 183/08 (58)調査した分野(Int.Cl.6，ＤＢ名) C07F 7/08 - 7/21 C08G 77/00 - 77/398 C08L 83/04 - 83/08 D06M 15/643 - 15/657 ──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 6 identification code FI C09D 183/08 C09D 183/08 (58) Field surveyed (Int.Cl. 6 , DB name) C07F 7/08-7/21 C08G 77/00-77/398 C08L 83/04-83/08 D06M 15/643-15/657
Claims (1)
部に対して、 式 RO(CmH2mO)nH (1) （式中、R は炭素原子数１〜20の一価の炭化水素基、ｍ
は１〜10の数、ｎは０〜20の数）で示されるアルコール
化合物0.001 〜10重量部を添加することを特徴とするア
ミノ基含有有機ケイ素化合物の着色ないし変色防止方
法。 1. An amino group-containing organosilicon compound ( 100% by weight)
Part, the formula RO (C m H 2m O) n H (1) (where R is a monovalent hydrocarbon group having 1 to 20 carbon atoms, m
A to the number of 1 to 10, n is characterized by adding an alcohol compound from 0.001 to 10 parts by weight represented by the number of 0 to 20)
How to prevent coloring or discoloration of amino-containing organosilicon compounds
Law.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7210615A JP2938789B2 (en) | 1995-08-18 | 1995-08-18 | Method for preventing coloration or discoloration of amino group-containing organosilicon compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7210615A JP2938789B2 (en) | 1995-08-18 | 1995-08-18 | Method for preventing coloration or discoloration of amino group-containing organosilicon compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0959285A JPH0959285A (en) | 1997-03-04 |
| JP2938789B2 true JP2938789B2 (en) | 1999-08-25 |
Family
ID=16592265
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7210615A Expired - Lifetime JP2938789B2 (en) | 1995-08-18 | 1995-08-18 | Method for preventing coloration or discoloration of amino group-containing organosilicon compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2938789B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7073319B2 (en) * | 2019-09-13 | 2022-05-23 | 旭化成ワッカーシリコーン株式会社 | An amino-modified silicone-containing oil-in-water emulsion composition that can suppress changes in color tone, a method for producing the same, a method for designing the same, and a cosmetic containing the composition. |
-
1995
- 1995-08-18 JP JP7210615A patent/JP2938789B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0959285A (en) | 1997-03-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6197989B1 (en) | Fluorinated organosilicon compounds and process for the preparation thereof | |
| US3161614A (en) | Polyfunctional alkoxy endblocked polysiloxanes and their cured compositions | |
| US6121404A (en) | β-diketo functional organosilicon compounds | |
| US5367001A (en) | Impression composition | |
| US5625024A (en) | Branched polysiloxane-polyether-based copolymers, their preparation and use | |
| US5057476A (en) | Platinum catalyst composition, method for its preparation and curable organopolysiloxane compositions containing same | |
| CA2364378A1 (en) | Cosmetic compositions containing silicone gel | |
| US5681914A (en) | Curable silicone composition | |
| US5118777A (en) | Polydimethylsiloxane terminated at one end by a branched aminoalkyl group and preparation thereof | |
| JPH0639570B2 (en) | Putty-like curable organopolysiloxane composition | |
| JPH05271547A (en) | Curable composition | |
| JP2550749B2 (en) | Curable silicone composition and cured product | |
| EP0278854A2 (en) | A curable and foamable organopolysiloxane composition | |
| FR2800086A1 (en) | One-component silicone composition for production of non-yellowing adhesive elastomer contains moisture-crosslinkable polysiloxane, filler, catalyst, sterically-hindered amine and adhesion promoter | |
| US5384382A (en) | Crosslinkable polysilane compositions and cured products thereof | |
| JP2938789B2 (en) | Method for preventing coloration or discoloration of amino group-containing organosilicon compound | |
| HUP0004654A2 (en) | An organic polysiloxane mass that can be cross-linked into an elastomer during the cleavage of alcohol | |
| KR920021626A (en) | (Meth) acryloxy group containing organosiloxane compound, its manufacturing method, and its use | |
| US4892895A (en) | Ultraviolet-curable organopolysiloxane composition | |
| JPH0512325B2 (en) | ||
| JP7636130B2 (en) | Organopolysiloxane having perfluoropolyether blocks and (meth)acryloyl groups, and method for producing same | |
| JPS603427B2 (en) | Oxygen-curable mercaptoorganosiloxane compositions containing both redox compounds and iron carbonyl compounds and methods for producing high molecular weight products therefrom | |
| US5449734A (en) | Curable composition | |
| JP2638396B2 (en) | Curable silicone composition and cured product thereof | |
| Ladilina et al. | Fluorine-containing dialkoxysilanes. The formation of complexes with aminopropyltriethoxysilane and production of transparent films |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 19990511 |