JP4944947B2 - β−ケトアミド基及びエナミン結合を介して結合した有機ポリマーを含有する有機ケイ素化合物、及びその製造方法 - Google Patents
β−ケトアミド基及びエナミン結合を介して結合した有機ポリマーを含有する有機ケイ素化合物、及びその製造方法 Download PDFInfo
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- JP4944947B2 JP4944947B2 JP2009508310A JP2009508310A JP4944947B2 JP 4944947 B2 JP4944947 B2 JP 4944947B2 JP 2009508310 A JP2009508310 A JP 2009508310A JP 2009508310 A JP2009508310 A JP 2009508310A JP 4944947 B2 JP4944947 B2 JP 4944947B2
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- 150000003961 organosilicon compounds Chemical class 0.000 title claims description 22
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 150000004798 β-ketoamides Chemical group 0.000 title description 4
- 229920000620 organic polymer Polymers 0.000 title description 2
- -1 aminosilicon compound Chemical class 0.000 claims description 26
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- OBFQBDOLCADBTP-UHFFFAOYSA-N aminosilicon Chemical compound [Si]N OBFQBDOLCADBTP-UHFFFAOYSA-N 0.000 claims description 14
- 229920000570 polyether Polymers 0.000 claims description 14
- 125000003277 amino group Chemical group 0.000 claims description 13
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910018540 Si C Inorganic materials 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- 229920001296 polysiloxane Polymers 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 claims 4
- 150000003377 silicon compounds Chemical class 0.000 claims 1
- 125000000962 organic group Chemical group 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical group CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 4
- 150000003141 primary amines Chemical class 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical group [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002081 enamines Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 150000003335 secondary amines Chemical group 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- LLPNBWNKPILNSX-UHFFFAOYSA-N 4-methylideneoxetan-2-one propan-2-one Chemical compound CC(C)=O.C=C1CC(=O)O1 LLPNBWNKPILNSX-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical group CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ZMTCHYALYZRJRQ-UHFFFAOYSA-N N'-(2-methylpropylsilyl)ethane-1,2-diamine Chemical compound CC(C)C[SiH2]NCCN ZMTCHYALYZRJRQ-UHFFFAOYSA-N 0.000 description 1
- PHIIOKFICBAPOS-UHFFFAOYSA-N NCCNCCC[SiH3] Chemical compound NCCNCCC[SiH3] PHIIOKFICBAPOS-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical compound CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 description 1
- 150000004729 acetoacetic acid derivatives Chemical class 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- BWRFQFVRMJWEQW-UHFFFAOYSA-N but-1-ene-1,3-dione Chemical compound CC(=O)C=C=O BWRFQFVRMJWEQW-UHFFFAOYSA-N 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
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical group CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical group CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920006112 polar polymer Polymers 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 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
- 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
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- 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
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Silicon Polymers (AREA)
Description
その際、−(Si≡)はケイ素原子に対する結合を意味し、
R1は、場合により互いに離れた窒素原子を有していてもよい1〜6個の炭素原子を有する二価の有機基、有利に場合により1つ以上の互いに離れた窒素原子を有していてもよい1〜6個の炭素原子を有する二価の炭化水素基を表し、
R2は、水素原子又は1〜30個のC原子を有する有機基を意味し、有利に水素原子又は1〜30個のC原子を有する炭化水素基を意味し、
R3は、1〜6個の炭素原子、有利に2〜6個の炭素原子を有する二価の有機基、有利に2〜6個の炭素原子を有する二価の炭化水素基を意味し、
R4は、水素原子又は1〜18個のC原子を有する炭化水素基を表し、
Yは、酸素又は−NR2−、有利に酸素を表し、
Zは、モノマー、オリゴマー又はポリマーの構造を有する二価〜六価の有機基を表し、これは、C原子を介して結合している、質量基準で少なくとも10%のヘテロ原子の含有率を有し、
E1は、単官能性末端基又は一般式
aは、1〜5の整数、有利に1又は2を表し及び
xは0又は1〜5の整数、有利に0又は1、特に1を表す。
その際、第1段階で、一般式
第2段階で、第1段階で得られた有機ケイ素化合物(1′)を、一般式
Rは、1〜18個のC原子を有する一価の炭素原子を表し、
gは、0又は1、
kは、0又は1〜30の整数、及び
lは、0又は1〜1000の整数であり
但し、1分子当たり少なくとも1つの基Aが含まれてる]のオルガノポリシロキサンである。
アセトアセチルポリエーテル(式C4H9O(C2H4O)18.0(C3H6O)17.4Hの単官能性ポリエーテルとジケテンとから製造)411gを、0.51mequiv./gのアセトアセチル濃度で、アミノエチルアミノプロピル−メチルシロキサン単位及びジメチルシロキサン単位からなる粘度830mm2/s(25℃)及び1.597のアミン価のコポリマー250gと混合し、撹拌しながら70℃に加熱する。それによりH2N/アセトアセチルの化学量論を0.95に調節する。著しく濁った混合物が約20分後に透明になる。同じ温度で2時間の後反応により著しい粘度上昇が生じ、この粘度上昇をイソプロパノール70gの添加によりかなり軽減する。ジケテン16.8gの供給により、即座にさらに粘度上昇を伴う明らかな発熱反応が生じる。さらにイソプロパノール156gを添加し、ゆっくりと撹拌する。エナミンを介してグラフトされたポリエーテル鎖を有しかつ同時にβ−ケトアミド基を有するシリコーンポリマーの75%の溶液が得られる。この溶液は1g当たり前記基0.22mequ.含有する。このポリマー溶液は明らかに水と混合可能である。
1106gの平均分子量を有するPEG−1000−ビス(アセトアセタート)116gを70℃で溶融させる。同じ温度で、α,ω−ビス(アミノエチルアミノプロピル)−ジメチルポリシロキサン263gを供給する。この混合物の粘度は明らかに上昇し、透明になる。さらに70℃で3時間後にジケテン8.4gを供給し、その後で発熱反応でさらに粘度上昇が起こる。冷却後に、0.26mequ./gのアセトアセトアミド含有量を有しかつ使用したポリエーテル過剰からのアセトアセタート基の同じ濃度を有する高粘性の油が得られる。ブチルグリコール中のこのポリマーの80%の溶液は、著しく剪断せずに同量の水に分散することができる。
Claims (4)
- 一般式
第1段階で、一般式
第2段階で、第1段階で得られた有機ケイ素化合物(1′)を、一般式
- 化合物(2)中のアミノ基Aはアミノエチルアミノプロピル基であることを特徴とする、請求項2記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102006020816A DE102006020816A1 (de) | 2006-05-04 | 2006-05-04 | Organosiliciumverbindungen, die beta-Ketoamidgruppen und über Enamin-Bindungen gebundene organische Polymere enthalten, und Verfahren zu ihrer Herstellung |
DE102006020816.1 | 2006-05-04 | ||
PCT/EP2007/053958 WO2007128680A1 (de) | 2006-05-04 | 2007-04-23 | ORGANOSILICIUMVERBINDUNGEN, DIE ß-KETOAMIDGRUPPEN UND ÜBER ENAMIN-BINDUNGEN GEBUNDENE ORGANISCHE POLYMERE ENTHALTEN, UND VERFAHREN ZU IHRER HERSTELLUNG |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2009535472A JP2009535472A (ja) | 2009-10-01 |
JP4944947B2 true JP4944947B2 (ja) | 2012-06-06 |
Family
ID=38277213
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009508310A Expired - Fee Related JP4944947B2 (ja) | 2006-05-04 | 2007-04-23 | β−ケトアミド基及びエナミン結合を介して結合した有機ポリマーを含有する有機ケイ素化合物、及びその製造方法 |
Country Status (7)
Country | Link |
---|---|
US (1) | US7939619B2 (ja) |
EP (1) | EP2013265B1 (ja) |
JP (1) | JP4944947B2 (ja) |
KR (1) | KR101027182B1 (ja) |
CN (1) | CN101421334B (ja) |
DE (2) | DE102006020816A1 (ja) |
WO (1) | WO2007128680A1 (ja) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102006020815A1 (de) * | 2006-05-04 | 2007-11-08 | Wacker Chemie Ag | Verfahren zur Herstellung von beta-Ketocarbonyl-funktionellen Organosiliciumverbindungen |
DE102006039940A1 (de) * | 2006-08-25 | 2008-03-06 | Wacker Chemie Ag | ß-Ketocarbonyl-funktionelle Siloxanpolymere enthaltende Zusammensetzungen |
EP3541882B1 (de) * | 2016-11-16 | 2020-04-22 | Wacker Chemie AG | Dispersionen von béta-ketocarbonyl-funktionellen organosiliciumverbindungen |
US11597840B2 (en) * | 2017-12-06 | 2023-03-07 | Wacker Chemie Ag | Emulsions of beta-ketocarbonyl-functional organosilicon compounds |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1154726A (en) | 1965-09-16 | 1969-06-11 | Ici Ltd | Esters of Polyethers |
GB1218509A (en) | 1969-02-03 | 1971-01-06 | Wacker Chemie Gmbh | Process for the production of acetoacetic acid esters |
FR2602776B1 (fr) * | 1986-08-12 | 1988-11-10 | Rhone Poulenc Chimie | Diorganopolysiloxane a fonction beta-cetoester utile comme stabilisant des polymeres a base de polychlorure de vinyle |
GB9101205D0 (en) * | 1990-02-14 | 1991-02-27 | Ici Plc | Incorporation of desired groups into polymers,the polymers so produced and composition containing them |
DE4034279A1 (de) * | 1990-10-27 | 1992-04-30 | Bayer Ag | Verwendung von alkoxysilylaminen als haerter fuer acetoacetat- oder acetoacetamidgruppen aufweisende kunststoffvorlaeufer |
JP3966913B2 (ja) * | 1995-02-08 | 2007-08-29 | ローム アンド ハース カンパニー | シランで変性された床仕上げ剤ビヒクル |
US5952443A (en) * | 1997-08-01 | 1999-09-14 | Ppg Industries Ohio, Inc. | Acetoacetate functional polysiloxanes |
US6121404A (en) | 1998-07-06 | 2000-09-19 | Dow Corning Corporation | β-diketo functional organosilicon compounds |
JP4357037B2 (ja) * | 1999-08-13 | 2009-11-04 | 株式会社Adeka | 硬化性組成物 |
US7459515B2 (en) * | 2004-09-15 | 2008-12-02 | Ppg Industries Ohio, Inc. | Fast-curing modified siloxane compositions |
DE102005056050A1 (de) | 2005-11-24 | 2007-05-31 | Wacker Chemie Ag | Alpha-(beta-Ketocarbonyl)-funktionelle Organosiliciumverbindungen und deren Herstellung |
-
2006
- 2006-05-04 DE DE102006020816A patent/DE102006020816A1/de not_active Withdrawn
-
2007
- 2007-04-23 CN CN2007800126811A patent/CN101421334B/zh not_active Expired - Fee Related
- 2007-04-23 US US12/299,545 patent/US7939619B2/en not_active Expired - Fee Related
- 2007-04-23 EP EP07728414A patent/EP2013265B1/de not_active Expired - Fee Related
- 2007-04-23 KR KR1020087027402A patent/KR101027182B1/ko not_active IP Right Cessation
- 2007-04-23 WO PCT/EP2007/053958 patent/WO2007128680A1/de active Application Filing
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EP2013265B1 (de) | 2009-08-05 |
DE102006020816A1 (de) | 2007-11-08 |
US20090176959A1 (en) | 2009-07-09 |
KR101027182B1 (ko) | 2011-04-05 |
EP2013265A1 (de) | 2009-01-14 |
CN101421334A (zh) | 2009-04-29 |
CN101421334B (zh) | 2011-09-28 |
DE502007001257D1 (de) | 2009-09-17 |
JP2009535472A (ja) | 2009-10-01 |
KR20080108609A (ko) | 2008-12-15 |
US7939619B2 (en) | 2011-05-10 |
WO2007128680A1 (de) | 2007-11-15 |
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