TWI725508B - 含有n-苄基-取代之n-(2-胺乙基)-3-胺丙基矽氧烷鹽酸鹽的水性、儲存安定性組成物,其製法及其用途 - Google Patents
含有n-苄基-取代之n-(2-胺乙基)-3-胺丙基矽氧烷鹽酸鹽的水性、儲存安定性組成物,其製法及其用途 Download PDFInfo
- Publication number
- TWI725508B TWI725508B TW108128501A TW108128501A TWI725508B TW I725508 B TWI725508 B TW I725508B TW 108128501 A TW108128501 A TW 108128501A TW 108128501 A TW108128501 A TW 108128501A TW I725508 B TWI725508 B TW I725508B
- Authority
- TW
- Taiwan
- Prior art keywords
- composition
- weight
- aminoethyl
- water
- benzyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 69
- 238000000034 method Methods 0.000 title claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 150000003840 hydrochlorides Chemical class 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 81
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 52
- 238000003860 storage Methods 0.000 claims abstract description 23
- 239000013543 active substance Substances 0.000 claims abstract description 18
- -1 N-benzyl-substituted N-(2-aminoethyl)-3-aminopropylsiloxane hydrochlorides Chemical class 0.000 claims abstract description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 33
- 238000004821 distillation Methods 0.000 claims description 26
- 239000000047 product Substances 0.000 claims description 16
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 11
- HOSQZKZVJBFALN-UHFFFAOYSA-N n'-benzyl-n-(3-trimethoxysilylpropyl)ethane-1,2-diamine;hydron;chloride Chemical compound Cl.CO[Si](OC)(OC)CCCNCCNCC1=CC=CC=C1 HOSQZKZVJBFALN-UHFFFAOYSA-N 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 8
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 6
- 239000000413 hydrolysate Substances 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 239000011149 active material Substances 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 239000002318 adhesion promoter Substances 0.000 claims description 3
- 239000002131 composite material Substances 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- 239000003365 glass fiber Substances 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 2
- 239000000853 adhesive Substances 0.000 claims description 2
- 230000001070 adhesive effect Effects 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000007789 sealing Methods 0.000 claims description 2
- 239000002002 slurry Substances 0.000 claims description 2
- 238000004458 analytical method Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 230000001568 sexual effect Effects 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- ZDZYGYFHTPFREM-UHFFFAOYSA-N 3-[3-aminopropyl(dimethoxy)silyl]oxypropan-1-amine Chemical compound NCCC[Si](OC)(OC)OCCCN ZDZYGYFHTPFREM-UHFFFAOYSA-N 0.000 description 1
- WSZUVZSAASQWLO-UHFFFAOYSA-N Cl.CO[Si](OC)(OC)CCCNCC(NC=C)CC1=CC=CC=C1 Chemical compound Cl.CO[Si](OC)(OC)CCCNCC(NC=C)CC1=CC=CC=C1 WSZUVZSAASQWLO-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009530 blood pressure measurement Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001739 density measurement Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002032 methanolic fraction Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- LRDRGASHPNRJHP-UHFFFAOYSA-N n'-benzyl-n-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCNCC1=CC=CC=C1 LRDRGASHPNRJHP-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002990 reinforced plastic Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/544—Silicon-containing compounds 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
- C07F7/18—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
-
- 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
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- 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
- C07F7/20—Purification, separation
-
- 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
-
- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
- C08K9/06—Ingredients treated with organic substances with silicon-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/45—Anti-settling agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/46—Anti-skinning agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Silicon Polymers (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
本發明係關於含有N-苄基-取代之N-(2-胺乙基)-3-胺丙基矽氧烷鹽酸鹽的水性組成物,其中該組成物於60℃儲存6週之後具有色值為≤ 1迦德納、甲醇含量為≤ 0.5重量%以及於水含量為≥ 40重量%至≤ 60重量%下之活性物質含量為≤ 60重量%,其中該組成物中之組分的總和為100重量%。本發明進一步關於提供此組成物之方法及其用途。
Description
本發明係關於含有N-苄基-取代之N-(2-胺乙基)-3-胺丙基矽氧烷鹽酸鹽(N-benzyl-substituted N-(2-aminoethyl)-3-aminopropylsiloxane hydrochloride)的水性、低VOC、儲存安定性組成物,關於提供此組成物之方法及其用途。
長久以來已知從烷氧基矽烷(特別是基於胺基烷基烷氧基矽烷)製造水性水解產物/縮合物(condensate) (尤其是EP 0 675 128 B1、EP 0 716 127 A2、EP 0 716 128 B1、EP 0 832 911 B1、EP 0 953 591 B1、EP 1 031 593 B1、EP 1 773 917 B1)。
EP 0 590 270 A2及WO 2005/118599 A1揭示用於製造有機矽烷聚縮合物之醇溶液之組成物及方法。根據EP 0 590 270 A2,N-(N-苄基-2-胺乙基)-3-胺丙基三甲氧基矽烷鹽酸鹽之水溶液不安定;添加水造成不均勻的混濁溶液。
已知藉由添加乙酸及去除甲醇餾分而從N-(N-苄基-2-胺乙基)-3-胺基-丙基三甲氧基矽烷製造水溶性水解產物,參考EP 0 716 127 A2之實施例7,以及使用彼作為例如黏著促進劑。
N-(N-乙烯基苄基-2-胺乙基)-3-胺丙基三甲氧基矽烷鹽酸鹽亦已知,尤其從Plueddemann, 39th Annual Conference, Reinforced Plastics/Composites Institute, The Society of the Plastic Industry, Inc. January 16-19, 1984, Session 4-C,第1-4頁;US 4,902,556、US 4,849,294、US 4,382,991、US 4,330,444、DE 28 02 242、JP 2000-230148 A2、EP 0 338 128、EP 0 353 766。
對許多應用而言,具有最高可能活性物質含量之水性、低VOC、理想為無色且儲存安定性產物的需求日益增加。
因此,本發明一目的係提供具有基於N-(N-苄基-2-胺乙基)-3-胺丙基-三甲氧基矽烷鹽酸鹽之最高可能活性物質含量且游離甲醇含量為≤ 0.5重量%的理想為無色且儲存安定,尤其是在高儲存溫度下無沉澱、低VOC、水性組成物。
根據本發明根據申請專利範圍中之特徵而獲致該目的。
因此,意外發現可有利地提供具有達60重量%之有利的高活性物質比例(即,N-苄基-取代之N-(2-胺乙基)-3-胺丙基矽氧烷鹽酸鹽[下文亦簡稱為活性物質])之水性、低VOC組成物,其實質上無甲醇(即,具有甲醇含量為≤ 0.5重量%),且於室溫下為儲存安定達至少1年。此外,本組成物即使在較高儲存溫度下亦未顯示沉澱,為澄清的且若需要可有利地以幾乎任何比率經水稀釋。又,本組成物實質上為無色,具有色值(colour number)為≤ 1迦德納(Gardner)。再者,本組成物為低VOC組成物,因其幾乎完全水解,即,根據化學理解(chemical understanding),其中存在之活性物質N-苄基-取代之N-(2-胺乙基)-3-胺丙基矽氧烷鹽酸鹽,基本上不再包含任何甲氧基。
本組成物之製造係根據以下方法變化A及B有利地達成:
方法變化A因而可有利地包含
- 於步驟1中,於室溫至60℃之底部物溫度(bottoms temperature)、於以現有輸入材料N-(2-胺乙基)-3-胺丙基三甲氧基矽烷及水為基準計為25重量%至30重量%之甲醇(較佳為27重量%之甲醇)存在下,以每莫耳之Si為1.15至1.25莫耳之水(較佳為每莫耳之Si為1.2莫耳之水)進行N-(2-胺乙基)-3-胺丙基三甲氧基矽烷之受控水解(controlled hydrolysis),
- 其後即於步驟2中,於58℃至60℃之底部物溫度,使步驟1中所獲得之水解產物(hydrolysate)與氯甲苯(benzyl chloride)反應,較佳係每莫耳之N-(2-胺乙基)-3-胺丙基三甲氧基矽烷為1莫耳之氯甲苯,隨後添加濃鹽酸,較佳為每莫耳之Si為0.9至1.0莫耳之HCl,以及
- 隨後於步驟3中,在減壓下及添加定量的水(較佳係每1.0 g之步驟1中所使用之矽烷為1.35 g之水),較佳係在303 mbar至111 mbar之絕對壓力以及43℃至51℃之底部物溫度下,從步驟2中所獲得之產物混合物蒸餾去除甲醇及任何在蒸餾條件下亦為揮發性之餾分,其中,水係同時添加至蒸餾底部物達使揮發性餾分於塔頂排出的量。
方法變化B可有利地包含
- 先裝填含有N-(N-苄基-2-胺乙基)-3-胺丙基三甲氧基矽烷鹽酸鹽之甲醇溶液,於室溫至60℃之溫度下以20至40分鐘在混合下以N-(N-苄基-2-胺乙基)-3-胺丙基三甲氧基矽烷鹽酸鹽對濃鹽酸為4至2:1(較佳為3.8:1)之重量比添加濃鹽酸,接著以1至5分鐘在混合下快速添加每莫耳N-(N-苄基-2-胺乙基)-3-胺丙基三甲氧基矽烷鹽酸鹽為1至2莫耳水之量的水之後於40℃至55℃之底部物溫度及280至120 mbar之減壓下從產物混合物蒸餾去除揮發性餾分,其中,水係同時添加至蒸餾底部物達使揮發性餾分於塔頂排出的量。
根據方法變化A或B所獲得之組成物適當地於蒸餾單元中以底部物產物獲得,且構成水性、低VOC組成物其具有活性物質含量為≤ 60重量%(例如≥ 40重量%至60重量%或45重量%至60重量%,僅舉例說明),在水含量為≥ 40重量%(較佳為≥ 40重量%至≤ 60重量%),且甲醇含量為≤ 0.5重量%,其中,組成物中之組分的總和為100重量%。如此獲得之組成物進一步有利地具有黏度為≥ 50至≤ 300 mPas(於20℃)、pH為≥ 2至≤ 4及色值為≤ 1迦德納,此外為澄清的、室溫下為儲存安定達至少1年,且可以幾乎任何比率與水互混。此外,如此獲得之組成物即使在高儲存溫度下亦幾乎未顯示沉澱。
本發明因此提供含有N-苄基-取代之N-(2-胺乙基)-3-胺丙基矽氧烷鹽酸鹽的水性組成物,其中,該組成物於60℃儲存6週之後具有色值為≤ 1迦德納[ISO 6274]、甲醇含量為< 0.5重量%以及於水含量為≥ 40重量%至≤ 60重量%下之活性物質含量為≤ 60重量%,其中,該組成物中之組分的總和為100重量%。
此外,根據本發明之組成物有利地具有其於室溫下為儲存安定達至少12個月且具色值為≤ 1迦德納、黏度為≥ 50至≤ 300 mPas(於20℃)以及pH為≥ 2至≤ 4之特徵。
根據本發明之組成物有利地含有呈異構N-苄基-取代之N-(2-胺乙基)-3-胺丙基矽氧烷(isomeric N-benzyl-substituted N-(2-aminoethyl)-3-aminopropylsiloxane)之混合物的N-苄基-取代之N-(2-胺乙基)-3-胺丙基矽氧烷鹽酸鹽作為所謂活性物質(active substance),其中,異構N-苄基-取代之N-(2-胺乙基)-3-胺丙基矽氧烷中之至少一者符合式I,
其中,R代表甲基或乙基,x ≥ 1且y=0或1且z=0或1,前提是(y+z) ≤ 1,以及A代表根據式II之胺烷基
其中,a=0或1且b=0及/或1或c=0或1,前提是(b+c)=0或1或2,其中,基團R1
、R2
及R3
代表苄基且d=0或1或2或3。
因此例如(但非僅此),根據本發明之組成物可較佳含有40重量%至60重量%之水且於活性物質分布中之活性物質為37.4莫耳%(mol%)之A型、18.8莫耳%之B型、18.9莫耳%之C型、8.4莫耳%之D型、4.8莫耳%之E型及11.7莫耳%之F型,其中,組成物之全部組分的總和為100重量%。
本發明進一步提供製造根據本發明之組成物之方法
其於方法變化A(process variant A)中包含
- 於步驟1中,於室溫至60℃之底部物溫度、於以現有輸入材料N-(2-胺乙基)-3-胺丙基三甲氧基矽烷及水為基準計為25重量%至30重量%之甲醇(較佳為27重量%之甲醇)存在下,以每莫耳之Si為1.15至1.25莫耳之水(較佳為每莫耳之Si為1.2莫耳之水)進行N-(2-胺乙基)-3-胺丙基三甲氧基矽烷之受控水解,
- 其後即於步驟2中,於58℃至60℃之底部物溫度,使步驟1中所獲得之水解產物與氯甲苯反應,較佳係每莫耳之N-(2-胺乙基)-3-胺丙基三甲氧基矽烷為1莫耳之氯甲苯,隨後添加濃鹽酸,較佳為每莫耳之Si為0.9至1.0莫耳之HCl,以及
- 隨後於步驟3中,在減壓下及添加定量的水(較佳係每1.0 g之步驟1中所使用之矽烷為1.35 g之水),較佳係在303 mbar至111 mbar之絕對壓力以及43℃至51℃之底部物溫度下,從步驟2中所獲得之產物混合物蒸餾去除甲醇及任何在蒸餾條件下亦為揮發性之餾分,其中,水係同時添加至蒸餾底部物達使揮發性餾分於塔頂排出的量
或
在方法變化B(process variant B)中包含
- 先裝填含有N-(N-苄基-2-胺乙基)-3-胺丙基三甲氧基矽烷鹽酸鹽之甲醇溶液,於室溫至60℃之溫度下以20至40分鐘在混合下以N-(N-苄基-2-胺乙基)-3-胺丙基三甲氧基矽烷鹽酸鹽對濃鹽酸為4至2:1(較佳為3.8:1)之重量比添加濃鹽酸,接著以1至5分鐘在混合下快速添加每莫耳N-(N-苄基-2-胺乙基)-3-胺丙基三甲氧基矽烷鹽酸鹽為1至2莫耳水之量的水之後於40℃至55℃之底部物溫度及280至120 mbar之減壓下從產物混合物蒸餾去除揮發性餾分,其中,水係同時添加至蒸餾底部物達使揮發性餾分於塔頂排出的量,
以
於方法變化A或B中於蒸餾單元之底部獲得具有在水含量為≥ 40重量%至≤ 60重量%之活性物質含量為≤ 60重量%以及甲醇含量為≤ 0.5重量%的水性、低VOC組成物,其中,該組成物中之組分的總和為100重量%,以及該組成物具有黏度為≥ 50至≤ 300 mPas (於20℃)、pH為≥ 2至≤ 4及色值為≤ 1迦德納,以及於室溫下為儲存安定達至少1年。
因此,本發明亦提供藉由根據本發明之方法可獲得或所獲得之水性組成物。
通常,根據本發明之方法可如下進行:
適用於進行本方法之設備為蒸餾(distillation)或精餾(rectification)單元,其包含例如(但非僅此)裝備有攪拌設備及用於溫度監測/控制之工具的可加熱/可冷卻之儲槽(tank)、附接之分離塔(separating column)(視情況包含填料(packing)、回流分配器(reflux divider)及儲存容器(reservoir vessel))、轉葉油泵(rotary vane oil pump)及用於壓力測量/控制之工具(包括冷阱(cold trap))。前文提及之方法變化A及B可有利地於此反應設備中進行。此外,參考下文之發明例示性實施態樣。
根據本發明之組成物以及根據本發明製造/獲得之產物及溶液有利地適於作為黏著促進劑,用於改質填料、顏料及/或無機表面,特別是用於填料塗層、顏料之塗層、無機表面之塗層;作為聚合物中、黏著劑中、密封組成物中、纖維複合材料中之添加劑,與聚合物(特別是熱塑性塑膠(thermoplastics)、熱固性塑膠(thermosets)、彈性體(elastomer))一起使用,用於功能化(functionalizing)聚合物、用於調整聚合物之親水性、用於功能化玻璃(特別是用於功能化玻璃纖維(glass fibre));以及作為水性漿料(aqueous size)之成分,用於玻璃纖維應用包括不添加水解觸媒。
前文提及之根據本發明之組成物的有利應用/用途可能性亦構成本發明標的之一部分。
分析方法:13
C-NMR-及1
H-NMR-測定係使用「400MHz Bruker NMR」設備進行,所使用溶劑為CDCl3
。
色值[迦德納]之測定係根據ISO 6274進行。
折射率之測定係根據DIN 51423進行,且密度係根據DIN 51757進行。
組成物中之游離甲醇(free methanol)含量的測定係根據SAA 1844進行。
以mPas表示之黏度係於20℃根據DIN 53015測定。
於20℃且以[g/cm³]表示之密度測定係根據DIN 51757進行。
折射率係根據DIN 51423測定。
pH係根據DIN 38409-H-1測定。
儲存安定性(storage stability)之試驗係在60℃之加速條件(accelerated condition)下進行。為此,待試驗之液體係儲存於無光之循環空氣乾燥櫃(circulating air drying cabinet)中的玻璃瓶(氣體空間係經氮惰化(inertize))。各情況之儲存溫度提高10 K模擬儲存時間加倍。於儲存之後,對樣品進行分析可偵測之變化(analytically detectable change)諸如例如色值的評估及研究。
比較例1:(根據EP 0 716 127 A2之實施例7)
設備:1公升四頸燒瓶,配備有蒸餾橋(distillation bridge)、滴液漏斗、KPG攪拌器、底部物溫度計(bottoms thermometer)、具有溫控之油浴(oil bath)、轉葉真空泵(rotary vane vacuum pump)、壓力計(manometer)。
先裝填446.7 g之Dynasylan® 1161 EQ,且於RT下逐滴添加25.0 g之DM水與49.5 g之冰醋酸的混合物。底部物溫度提高至38.5℃。水解產物隨後以375.0 g之DM水稀釋。於301 mbar至250 mbar之絕對壓力下,總共去除370.6 g之餾出物。於蒸餾期間添加DM水。產率:758.1 g之黃色液體,具有活性物質含量為28.8%。
分析結果:
於50℃儲存一天之後,產物展現沉澱及沉降物(sediment)。
根據比較例1製造之產物經水稀釋時,例如於DM水中0.5重量%至2重量%之產物,於僅1小時之後系統變成乳白/混濁。
比較例2:(根據EP 0 590 270 A2之實施例2):
根據EP 0 590 270 A2之實施例2製造的組成物具有甲醇含量為59.9重量%。
比較例3:(根據EP 0 590 270 A2之實施例4)
根據EP 0 590 270 A2之實施例4的教示製造之組成物亦具有甲醇含量為59.9重量%。
實施例1
設備:15公升之雙壁實驗室反應器(double-walled laboratory reactor),配備有計量泵(metering pump)、蒸餾橋、KPG攪拌器、底部物溫度計、轉葉真空泵、壓力計、具有溫控工具之油恆溫器(oil thermostat)。
先裝填7724.7 g之Dynasylan® 1161 EQ (50%活性物質含量,於甲醇中)且1160.4 g之鹽酸(w=34.8%)係以26分鐘在攪拌下添加至Dynasylan® 1161 EQ。溫度提高至51.6℃。然後以2分鐘添加3892.1 g之水。於底部物溫度為41℃至53℃且絕對壓力為272 mbar至141 mbar下,去除總共8759.8 g之餾出物(distillate)。於蒸餾期間添加DM水。產率:6436 g之澄清淡黃色液體,具有活性物質含量為60重量%。
產物於60℃下為儲存安定達> 8週。
分析結果:
色值:於製造後為< 1迦德納
於60℃儲存8週之後為< 1迦德納
此外,關於可能的水性應用,例如用於特殊底漆(primer)應用,根據實施例1所獲得之組成物有利地實質上可自由以水稀釋而無任何混濁。
實施例2
設備:4公升四頸燒瓶,配備有蒸餾橋、滴液漏斗、KPG攪拌器、底部物溫度計、具有溫控之油浴、轉葉真空泵、壓力計。
先於室溫下裝填889.6 g之Dynasylan® DAMO,並將368.0 g之甲醇拌入。底部物溫度從21℃提高至37℃。然後以5分鐘添加86.4 g之DM水,且混合物係於50℃再攪拌30分鐘。於底部物溫度為58℃至60℃下,以2.7小時逐滴添加506.4 g之氯甲苯,且混合物係於58℃至60℃再攪拌5小時。底部物樣品之分析顯示游離氯甲苯(free benzyl chloride)含量為< 0.1重量%。以30分鐘逐滴添加228.7 g之濃鹽酸(w=37%)。然後以1200 g之DM水稀釋反應混合物。於底部物溫度為43℃至51℃且絕對壓力為300 mbar至111 mbar下,去除總共2075 g之餾出物。於蒸餾期間添加DM水。產率:2321 g之澄清淡黃色液體,具有活性物質含量為60重量%。產物於60℃下為儲存安定達> 14.5週。
分析結果:
實施例3
設備:4公升四頸燒瓶,配備有蒸餾橋、滴液漏斗、KPG攪拌器、底部物溫度計、具有溫控之油浴、轉葉真空泵、壓力計。
先於室溫下裝填1112 g之Dynasylan® DAMO,並將460 g之甲醇拌入。底部物溫度從21℃提高至38℃。隨後於底部物溫度為58℃至60℃下,以1.25小時逐滴添加633 g之氯甲苯,且混合物係於58℃至60℃再攪拌3小時。底部物樣品之分析顯示游離氯甲苯含量為< 0.1重量%。於底部物溫度為39℃下,以21分鐘逐滴添加456.3 g之濃鹽酸(w=37%)。於底部物溫度為40℃至57℃且絕對壓力為250 mbar至180 mbar下,去除總共1570.1 g之餾出物。於蒸餾期間添加DM水。產率:2891.4 g之澄清淡黃色液體,具有活性物質含量為60重量%。產物於60℃下為儲存安定達> 10週。
分析結果:
實施例4
設備:15公升之雙壁實驗室反應器,配備有計量泵、蒸餾橋、KPG攪拌器、底部物溫度計、轉葉真空泵、壓力計、具有溫控工具之油恆溫器。
先裝填5782.4 g之Dynasylan® DAMO,並將2392 g之甲醇拌入。底部物溫度從21℃提高至38℃。隨後於底部物溫度為58℃至60℃下,以約6小時逐滴添加3291.6 g之氯甲苯,且混合物係於58℃至60℃再攪拌3小時。底部物樣品之分析顯示游離氯甲苯含量為< 0.1重量%。於底部物溫度為25℃下,以3小時逐滴添加2382.1 g之濃鹽酸(w=37%)。於底部物溫度為30℃至56℃且絕對壓力為250 mbar至152 mbar下,去除總共8149 g之餾出物。於蒸餾期間添加DM水。產率:14 670 g之澄清淡黃色液體,具有活性物質含量為60重量%。
色值:於製造後為< 1迦德納
於60℃儲存3週之後為< 1迦德納
於60℃儲存6週之後為< 1迦德納
Claims (9)
- 如請求項1之組成物,其中,該活性物質含有呈異構N-苄基-取代之N-(2-胺乙基)-3-胺丙基矽氧烷之混合物的N-苄基-取代之N-(2-胺乙基)-3-胺丙基矽氧烷鹽酸鹽,其中,異構N-苄基-取代之N-(2-胺乙基)-3-胺丙基矽氧烷中之至少一者符合式I[亦簡稱為活性物質]HO(1-y)(RO)y[(A)SiO(OH)(1-z)(OR)z]x-R (I),其中,R代表甲基或乙基,x1且y=0或1且z=0或1,前提是(y+z)1,以及A代表根據式II之胺烷基[-(CH2)3N(H(1-a)R1 a)(CH2)2(NH[2-(b+c)][R2 bR3 c)].(HCl)d (II)其中,a=0或1且b=0或1或c=0或1,前提是(b+c)=0或1或2,其中,基團R1、R2及R3代表苄基且d=0或1或2或3。
- 如請求項1或2之組成物,其中,該組成物於室溫下為儲存安定達至少12個月。
- 一種用於製造如請求項1至4中任一項之組成物之方法,其於方法變化A中包含- 於步驟1中,於室溫至60℃之底部物溫度(bottoms temperature)、於以現有輸入材料N-(2-胺乙基)-3-胺丙基三甲氧基矽烷及水為基準計為25重量%至30重量%之甲醇存在下,以每莫耳之Si為1.15至1.25莫耳之水進行N-(2-胺乙基)-3-胺丙基三甲氧基矽烷之受控水解,- 其後即於步驟2中,於58℃至60℃之底部物溫度,使步驟1中所獲得之水解產物與氯甲苯反應;隨後添加濃鹽酸,以及- 隨後於步驟3中,在減壓下及添加定量的水,從步驟2中所獲得之產物混合物蒸餾去除甲醇及任何在蒸餾條件下亦為揮發性之餾分,其中,水係同時添加至蒸餾底部物達使揮發性餾分於塔頂排出的量,或在方法變化B中包含- 先裝填含有N-(N-苄基-2-胺乙基)-3-胺丙基三甲氧基矽烷鹽酸鹽之甲醇溶液,於室溫至60℃之溫度下以20至40分鐘在混合下以N-(N-苄基-2-胺乙基)-3-胺丙基三甲氧基矽烷鹽酸鹽對濃鹽酸為4至2:1之重量比添加濃鹽酸,接著以1至5分鐘在混合下快速添加每莫耳N-(N-苄基-2-胺乙基)-3-胺丙基三甲氧基矽烷鹽酸鹽為1至2莫耳水之量的 水之後於40℃至55℃之底部物溫度及280至120mbar之減壓下從產物混合物蒸餾去除揮發性餾分,其中,水係同時添加至蒸餾底部物達使揮發性餾分於塔頂排出的量,以於方法變化A或B中於蒸餾單元之底部獲得具有在水含量為40重量%至60重量%之活性物質含量為60重量%以及甲醇含量為0.5重量%的水性、低VOC組成物,其中,該組成物中之組分的總和為100重量%,以及該組成物具有黏度為50至300mPas(於20℃)、pH為2至4及色值為1迦德納,以及於室溫下為儲存安定達至少1年。
- 如請求項5之方法,其中,於方法變化A中,其包含於步驟2中添加/使用每莫耳Si為0.9至1.0莫耳HCl之量的濃鹽酸。
- 如請求項5之方法,其中,於方法變化A中,其包含於步驟3中在303mbar至111mbar之絕對壓力以及43℃至51℃之底部物溫度下從該產物混合物蒸餾去除甲醇及任何在蒸餾條件下亦為揮發性之餾分,同時添加水至該蒸餾底部物達使揮發性餾分於塔頂排出的量。
- 一種水性組成物,其可根據請求項5至7中任一項獲得。
- 一種如請求項1至4及8中任一項之組成物的用途,係作為黏著促進劑,用於改質填料、顏料及/或無機表面;作為聚合物中、黏著劑中、密封組成物中、纖 維複合材料中之添加劑,與聚合物一起使用,用於功能化(functionalizing)聚合物、用於調整聚合物之親水性、用於功能化玻璃;以及作為水性漿料之成分,用於玻璃纖維應用包括不添加水解觸媒。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP18189502.0 | 2018-08-17 | ||
EP18189502.0A EP3611236B1 (de) | 2018-08-17 | 2018-08-17 | Eine wässrige, lagerstabile zusammensetzung, die n-benzyl-substituierte n-(2-aminoethyl)-3-aminopropylsiloxan-hydrochloride enthält, verfahren zu deren herstellung und deren verwendung |
Publications (2)
Publication Number | Publication Date |
---|---|
TW202022025A TW202022025A (zh) | 2020-06-16 |
TWI725508B true TWI725508B (zh) | 2021-04-21 |
Family
ID=63363889
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
TW108128501A TWI725508B (zh) | 2018-08-17 | 2019-08-12 | 含有n-苄基-取代之n-(2-胺乙基)-3-胺丙基矽氧烷鹽酸鹽的水性、儲存安定性組成物,其製法及其用途 |
Country Status (7)
Country | Link |
---|---|
US (1) | US11292911B2 (zh) |
EP (1) | EP3611236B1 (zh) |
JP (1) | JP7268134B2 (zh) |
KR (1) | KR102538371B1 (zh) |
CN (1) | CN112534011B (zh) |
TW (1) | TWI725508B (zh) |
WO (1) | WO2020035432A1 (zh) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0590270A2 (de) * | 1992-10-01 | 1994-04-06 | Hüls Aktiengesellschaft | Organosilanpolykondensate |
CN101353480A (zh) * | 2007-07-27 | 2009-01-28 | 德古萨有限责任公司 | 氨基官能团的聚硅氧烷以及基于此的组合物 |
Family Cites Families (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU1664876A (en) | 1975-08-11 | 1978-02-09 | Du Pont | Caustic-resistant polymer coatings for glass |
FR2377982A1 (fr) | 1977-01-19 | 1978-08-18 | Saint Gobain | Compositions pour le revetement de fibres de verre et fibres ainsi obtenues |
US4330444A (en) | 1979-09-04 | 1982-05-18 | Ppg Industries, Inc. | Sizing composition and sized fibers with increased hardness |
US4382991A (en) | 1979-09-04 | 1983-05-10 | Ppg Industries, Inc. | Sizing composition and sized strand useful as reinforcement |
US4499152A (en) | 1982-08-09 | 1985-02-12 | General Electric Company | Metal-clad laminate construction |
EP0176062A3 (en) | 1984-09-27 | 1987-07-15 | Dow Corning Corporation | Silane bonding agents for high temperature applications and method therefor |
JPH0632530B2 (ja) * | 1985-07-03 | 1994-04-27 | 日本電気株式会社 | 光フアイバハイドロホン |
US4749614A (en) | 1986-04-10 | 1988-06-07 | International Business Machines Corporation | Process for coating fibers, use thereof, and product |
US4849294A (en) | 1986-05-09 | 1989-07-18 | Dow Corning Corporation | Coupling agent composition |
EP0276291A4 (en) | 1986-07-24 | 1988-11-16 | Schwebel Fiberglass | METHOD FOR TREATING GLASS SURFACES WITH CONNECTING AGENTS AND RESINS FOR PRODUCING AN IMPROVED SURFACE FOR BINDING A FINAL RESIN. |
JPH01259369A (ja) | 1988-04-11 | 1989-10-17 | Canon Inc | マイクロカプセルトナー |
JPH0757810B2 (ja) | 1988-04-15 | 1995-06-21 | 日本ゼオン株式会社 | ガラス繊維強化ノルボルネン系ポリマーおよびその製造法 |
US4910077A (en) | 1988-08-04 | 1990-03-20 | B.F. Goodrich Company | Polynorbornene laminates and method of making the same |
US4902556A (en) | 1989-01-27 | 1990-02-20 | The B. F. Goodrich Company | Multi-layer polynorbornene and epoxy laminates and process for making the same |
JPH07258415A (ja) * | 1994-03-22 | 1995-10-09 | Asahi Shiyueebell Kk | シラン組成物 |
DE69429335T2 (de) | 1994-03-31 | 2002-08-22 | Sivento Inc | Verfahren zur Herstellung stabiler wässriger Silan-Zusammensetzungen |
DE4443825A1 (de) | 1994-12-09 | 1996-06-13 | Huels Chemische Werke Ag | Wasserbasierende Organopolysiloxan-haltige Zusammensetzungen, Verfahren zu deren Herstellung und deren Verwendung |
DE4443824A1 (de) | 1994-12-09 | 1996-06-13 | Huels Chemische Werke Ag | Organopolysiloxan-haltige Zusammensetzungen auf Wasserbasis, Verfahren zu deren Herstellung sowie deren Verwendung |
DE19639782A1 (de) | 1996-09-27 | 1998-04-02 | Huels Chemische Werke Ag | Glycidether-, Acryl- und/oder Methacryl-funktionelle Organopolysiloxan-haltige Zusammensetzungen auf Wasser-Basis, Verfahren zu deren Herstellung sowie deren Verwendung |
DE19818923A1 (de) | 1998-04-28 | 1999-11-04 | Degussa | Stabile Zusammensetzungen wasserlöslicher, Amino- und Alkenyl-funktioneller Organosiloxane, Verfahren zu ihrer Herstellung und ihre Verwendung |
JP4229509B2 (ja) | 1999-02-15 | 2009-02-25 | 旭化成エレクトロニクス株式会社 | ガラス繊維用表面処理剤 |
DE19908636A1 (de) | 1999-02-27 | 2000-08-31 | Degussa | Wasserbasierende Zusammensetzung aminofunktioneller Siliciumverbindungen |
DE102004001368A1 (de) * | 2004-01-08 | 2005-08-04 | Vincent Chuang | Arylalkylaminofunktionelle Silane für Epoxidlaminate |
DE102004025767A1 (de) | 2004-05-26 | 2005-12-22 | Degussa Ag | Stabile Lösungen von N-substituierten Aminopolysiloxanen, deren Herstellung und Verwendung |
DE102004037043A1 (de) | 2004-07-29 | 2006-03-23 | Degussa Ag | Blockkondensate organofunktioneller Siloxane, deren Herstellung, Verwendung sowie deren Eigenschaften |
EP3473633B8 (de) | 2017-10-18 | 2019-12-18 | Evonik Operations GmbH | Eine farblose, 3-(n-vinylbenzyl-2-aminoethyl)aminopropyltrimethoxysilanhydrochlorid und methanol enthaltenden zusammensetzung, ein verfahren zu deren herstellung und deren verwendung |
-
2018
- 2018-08-17 EP EP18189502.0A patent/EP3611236B1/de active Active
-
2019
- 2019-08-12 WO PCT/EP2019/071537 patent/WO2020035432A1/en active Application Filing
- 2019-08-12 US US17/268,874 patent/US11292911B2/en active Active
- 2019-08-12 KR KR1020217007379A patent/KR102538371B1/ko active IP Right Grant
- 2019-08-12 TW TW108128501A patent/TWI725508B/zh active
- 2019-08-12 JP JP2021507891A patent/JP7268134B2/ja active Active
- 2019-08-12 CN CN201980053613.2A patent/CN112534011B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0590270A2 (de) * | 1992-10-01 | 1994-04-06 | Hüls Aktiengesellschaft | Organosilanpolykondensate |
CN101353480A (zh) * | 2007-07-27 | 2009-01-28 | 德古萨有限责任公司 | 氨基官能团的聚硅氧烷以及基于此的组合物 |
Also Published As
Publication number | Publication date |
---|---|
WO2020035432A1 (en) | 2020-02-20 |
TW202022025A (zh) | 2020-06-16 |
JP2021533243A (ja) | 2021-12-02 |
CN112534011A (zh) | 2021-03-19 |
US11292911B2 (en) | 2022-04-05 |
US20210246313A1 (en) | 2021-08-12 |
EP3611236A1 (de) | 2020-02-19 |
KR20210047890A (ko) | 2021-04-30 |
EP3611236B1 (de) | 2020-09-30 |
CN112534011B (zh) | 2022-04-26 |
JP7268134B2 (ja) | 2023-05-02 |
KR102538371B1 (ko) | 2023-06-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US6534667B1 (en) | Water-based composition of amino-functional silicon compounds | |
US5629400A (en) | Water-based organopolysiloxane-containing compositions, processes for their preparation and their use | |
KR101183178B1 (ko) | 실리콘 고무 재료용 경화제 | |
US6288256B1 (en) | Fluoroalkyl-functional organopolysiloxane-containing compositions based on water, a process for their preparation and their use | |
US6491838B1 (en) | Triamino- and fluoroalkyl-functional organosiloxanes | |
KR100898442B1 (ko) | 폴리에테르-작용성 실록산, 폴리에테르 실록산-함유조성물, 그의 제조 방법 및 그의 용도 | |
US5068277A (en) | Hydrolyzable silicone polymers | |
JP6337693B2 (ja) | シランカップリング剤水溶液、その製造方法及び表面処理剤 | |
JP3849872B2 (ja) | アミノ基含有シラノール化合物水溶液、その用途、およびその製造方法 | |
WO2014099497A2 (en) | Alkoxy polysiloxanes and methods of making alkoxy silanes and siloxanes | |
TWI725508B (zh) | 含有n-苄基-取代之n-(2-胺乙基)-3-胺丙基矽氧烷鹽酸鹽的水性、儲存安定性組成物,其製法及其用途 | |
TWI810349B (zh) | 含有3-環氧丙基氧基丙基烷氧基矽烷寡聚物之組成物,其製法和其用途 | |
JP6732804B2 (ja) | アミノアルキルトリアルコキシシランの水性加水分解物を製造する方法 | |
CN104220449A (zh) | 新型、易合成、自发水溶性、基本不含voc的环保(甲基)丙烯酰氨基-官能的硅氧烷醇体系、其制备方法和用途 | |
EP1925627B1 (en) | Water-soluble silicon-containing polymer, making method, coating composition, and coated article | |
KR101922256B1 (ko) | 플루오로알킬기를 갖는 알콕시실란 화합물 및 그의 제조 방법 | |
US10266655B2 (en) | Aqueous composition comprising [3-(2,3-dihydroxyprop-1-oxy)propyl] silanol oligomers, process for preparation thereof and use thereof | |
TWI795636B (zh) | 不含voc的水性及儲存穩定之n-乙烯基苄基胺基烷基官能性矽氧烷醇及其製造方法 | |
JP2002120332A (ja) | 塗膜の構造 | |
CN114940753A (zh) | 抗指纹树脂、其制备方法及抗指纹液 | |
JP2004359556A (ja) | シラノール基含有化合物、その製造方法、シラノール基含有化合物の水溶液、表面処理剤およびガラス繊維 | |
SK482006A3 (sk) | Organokremičité substituované bis(2-hydroxypropyl)amíny |