JP5329084B2 - シロキサンポリマーを安定化する方法 - Google Patents
シロキサンポリマーを安定化する方法 Download PDFInfo
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- JP5329084B2 JP5329084B2 JP2007520324A JP2007520324A JP5329084B2 JP 5329084 B2 JP5329084 B2 JP 5329084B2 JP 2007520324 A JP2007520324 A JP 2007520324A JP 2007520324 A JP2007520324 A JP 2007520324A JP 5329084 B2 JP5329084 B2 JP 5329084B2
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- 229920000642 polymer Polymers 0.000 title claims abstract description 42
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 20
- 230000000087 stabilizing effect Effects 0.000 title claims description 6
- -1 aminosiloxane Chemical class 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical group CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 claims description 15
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 229920001296 polysiloxane Polymers 0.000 claims description 11
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 5
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001354 dialkyl silanes Chemical class 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 230000003019 stabilising effect Effects 0.000 abstract 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical group 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000002191 fatty alcohols Chemical class 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 125000005372 silanol group Chemical group 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 2
- 210000004209 hair Anatomy 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HXDMXWXYZHDHLS-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]-2-methylpropyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CC(C)CNCCN HXDMXWXYZHDHLS-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000012643 polycondensation polymerization Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- MBMALLQVOCVDBO-UHFFFAOYSA-N 1-[methoxy-methyl-(2-methylpropyl)silyl]oxypropane-1,3-diamine Chemical compound CC(C)C[Si](C)(OC)OC(N)CCN MBMALLQVOCVDBO-UHFFFAOYSA-N 0.000 description 1
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- HXLAEGYMDGUSBD-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propan-1-amine Chemical compound CCO[Si](C)(OCC)CCCN HXLAEGYMDGUSBD-UHFFFAOYSA-N 0.000 description 1
- KTLWFMBUTGVOPU-UHFFFAOYSA-N 3-aminosilyl-1,1,1-trimethoxypropane Chemical compound COC(OC)(OC)CC[SiH2]N KTLWFMBUTGVOPU-UHFFFAOYSA-N 0.000 description 1
- WTUCTMYLCMVYEX-UHFFFAOYSA-N 4,4,4-trifluorobutanoic acid Chemical compound OC(=O)CCC(F)(F)F WTUCTMYLCMVYEX-UHFFFAOYSA-N 0.000 description 1
- GWJIQTJHFJDCPX-UHFFFAOYSA-N 4-[2-aminoethyl(dimethoxy)silyl]butan-2-amine Chemical compound NCC[Si](OC)(OC)CCC(C)N GWJIQTJHFJDCPX-UHFFFAOYSA-N 0.000 description 1
- KJUKORMMEYQSEC-UHFFFAOYSA-N 5-(aminomethoxy-methoxy-methylsilyl)-4-methylpentan-1-amine Chemical compound NCO[Si](C)(OC)CC(C)CCCN KJUKORMMEYQSEC-UHFFFAOYSA-N 0.000 description 1
- WOQKRTMEDFPTNU-UHFFFAOYSA-N CN(C)[SiH](CCCN)OC Chemical compound CN(C)[SiH](CCCN)OC WOQKRTMEDFPTNU-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- FZQSLXQPHPOTHG-UHFFFAOYSA-N [K+].[K+].O1B([O-])OB2OB([O-])OB1O2 Chemical compound [K+].[K+].O1B([O-])OB2OB([O-])OB1O2 FZQSLXQPHPOTHG-UHFFFAOYSA-N 0.000 description 1
- 239000003082 abrasive agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 229960001716 benzalkonium Drugs 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
- 239000006227 byproduct Substances 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000006038 hexenyl group Chemical group 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
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 230000037303 wrinkles Effects 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
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
- C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond
-
- 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
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Silicon Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
本発明は、シロキサンポリマーを安定化する方法に関し、特にアミノ官能性シロキサンポリマーの粘度を安定化する方法に関する。
アミン官能性は、シラノール縮合に関して触媒活性である。アミノ官能性シロキサンが多量のシラノールを用いて調製される場合、アミン官能性の影響を受け、シラノール基が縮合してシラン結合を形成するにつれ、ポリマーの粘度が高くなる傾向にある。
本発明は、下記の一般式:
R3−bXb−SiO−(R2SiO)n−(RSiO3/2)m−SiO−Xb−R3-b
(式中、各Rは炭化水素基を表し、但し一分子あたり少なくとも1つのRがアミノアルキルを表し;各Xは基R、水酸基又はアルコキシ基を表し、但し一分子あたり少なくとも1つのXが水酸基を表し;bは1、2又は3であり;n及びmは、25℃でのシロキサンポリマーの粘度が1〜100,000mPa・sの範囲であるような値を有する整数である)のアミノ官能性シロキサンポリマーの粘度を安定化する方法であって、アミノアルキル基と、Siに結合した少なくとも1つのアルコキシ基とを含有するアミノシラン又はアミノシロキサン(A)をシラノール官能性ポリシロキサン(B)と反応させることを含み、前記(A)及び(B)の反応前又は反応中に、前記(A)及び(B)の総重量を基準として、0.1〜10重量%のジアルコキシジアルキルシランを前記(A)及び/又は(B)に添加することにより、粘度安定性が改善されたアミノ官能性シロキサンポリマーが生成することを特徴とする方法である。
アミノ官能性シロキサンポリマーは、典型的に、下記の一般式を有する。
R3-bXb−SiO−(R2SiO)n−(RSiO3/2)m−SiO−Xb−R3-b
式中、各Rは炭化水素基を表し、但し一分子あたり少なくとも1つのRがアミノアルキルを表し;各Xは基R、水酸基又はアルコキシ基を表し、但し一分子あたり少なくとも1つのXが水酸基を表し;bは1、2又は3であり;n及びmは、25℃でのシロキサンポリマーの粘度が1〜100,000mPa・sの範囲であるような値を有する整数である。適切なR基としては、アルキル、アルケニル、アリール、シクロアルキル、又はアミン、アミドエーテル若しくはエポキシ官能基で置換された基であり、但し一分子あたり少なくとも1つのR基が、アミン置換基(例えば、アミノアルキル)を有する、ケイ素に結合した基である。好ましくは、全R基の少なくとも80%が、5個以下の炭素原子を有するアルキル基であり、最も好ましくはメチル基である。好ましくは、nは、25℃でのシロキサンポリマーの粘度が20〜60,000mPa・s、より好ましくは50〜5,000mPa・s、最も好ましくは100〜1,500mPa・sであるような値を有する整数である。
約60mPa・sの粘度を有する24.66kgの直鎖シラノール末端封鎖ポリジメチルシロキサンを反応容器に入れた。撹拌を始め、反応容器の内容物を100℃に加熱した。342.5gの3−(2−アミノエチルアミノ)−2−メチルプロピルメチルジメトキシシラン及び25gのオクタン酸を加え、反応容器の内容物を3時間の還流に維持した。100℃で4時間加熱し続けながら、100ミリバール(1000Pa)の圧力で真空を適用した。この段階で生成したアミノ官能性シランポリマーの粘度は、450mPa・sであった。
3−(2−アミノエチルアミノ)−2−メチルプロピルメチルジメトキシシランを322.5gの3−(2−アミノエチルアミノ)プロピルメチルジメトキシシランと置き換えた以外は、実施例1の方法により、アミノ官能性シロキサンポリマーを製造した。
ジメトキシジメチルシランを添加する段階及び後の反応がないこと以外は、実施例1及び2の方法により、アミノ官能性シロキサンポリマーを製造した。
加熱マントル、窒素雰囲気生成装置、滴下漏斗、温度計及び撹拌機を備えたフラスコで、約3,500の平均分子量及び70mPa・sの粘度を有する515gのシラノール末端封鎖ポリジメチルシロキサンと、17.2gの3−(アミノエチル)−アミノ−2−メチルプロピルメチルジメトキシシランと、8.9gの市販の脂肪アルコール(エクソンモービルによるアクロポール35(Acropol 35))と、4.8gのジメトキシジメチルシラン(DMDM)と、混合物の総重量を基準として0.14重量%の、Na3PO4・12H2O及びBa(OH)2・8H2Oの25/75混合物とを混合した。反応混合物を、還流させながら3時間、撹拌して85℃に加熱した。次いで、85℃で2時間加熱し続けながら、200ミリバール(2000Pa)の圧力で真空を適用した。生成したアミノ官能シロキサンポリマーの粘度は1216mPa・sであった。
4.8gのDMDMを省略した以外は、実施例3の方法により、アミノ官能シロキサンポリマーを製造した。
比較例3の方法により、アミノ官能性シロキサンポリマーを製造した。アミノ官能性シロキサンポリマー生成物を5つのサンプルに分け、各種量のジメトキシジメチルシラン(DMDM)を添加した。比較のために、1つのサンプルには、DMDMは添加しなかった。サンプルを25℃で保存した後、それらの粘度(mPa・sで)を1及び2週間後に測定した。かかる結果を下記の表3に示す。
Claims (6)
- 下記の一般式:
R3−bXb−SiO−(R2SiO)n−(RSiO3/2)m−SiO−Xb−R3-b
(式中、各Rは炭化水素基を表し、但し一分子あたり少なくとも1つのRがアミノアルキルを表し;各Xは基R、水酸基又はアルコキシ基を表し、但し一分子あたり少なくとも1つのXが水酸基を表し;bは1、2又は3であり;n及びmは、25℃でのシロキサンポリマーの粘度が1〜100,000mPa・sの範囲であるような値を有する整数である)のアミノ官能性シロキサンポリマーの粘度を安定化する方法であって、
アミノアルキル基と、Siに結合した少なくとも1つのアルコキシ基とを含有するアミノシラン又はアミノシロキサン(A)をシラノール官能性ポリシロキサン(B)と反応させることを含み、前記(A)及び(B)の反応前又は反応中に、前記(A)及び(B)の総重量を基準として、0.1〜10重量%のジアルコキシジアルキルシランを前記(A)及び/又は(B)に添加することにより、粘度安定性が改善されたアミノ官能性シロキサンポリマーが生成することを特徴とする方法。 - 前記(A)及び(B)の総重量を基準として、0.2〜6重量%のジアルコキシジアルキルシランを添加することを特徴とする請求項1に記載の方法。
- 前記シラノール官能性ポリシロキサン(B)は、重合度が4〜1000の直鎖ヒドロキシル先端ポリジメチルシロキサンである請求項1〜3のいずれか一項に記載の方法。
- 前記ジアルコキシジアルキルシランが、式Z2Si(OZ’)2(式中、各Zは1又は2個の炭素原子を有するアルキル基を表し、各Z’は1又は2個の炭素原子を有するアルキル基を表す)からなる請求項1〜4のいずれか一項に記載の方法。
- 前記ジアルコキシジアルキルシランが、ジメトキシジメチルシランであることを特徴とする請求項5に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0415001.7 | 2004-07-03 | ||
GBGB0415001.7A GB0415001D0 (en) | 2004-07-03 | 2004-07-03 | Process of stabilising siloxane polymers |
PCT/US2005/021449 WO2006014229A1 (en) | 2004-07-03 | 2005-06-17 | Process of stabilising siloxane polymers |
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JP2008511688A JP2008511688A (ja) | 2008-04-17 |
JP5329084B2 true JP5329084B2 (ja) | 2013-10-30 |
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US (1) | US7781505B2 (ja) |
EP (1) | EP1776413B1 (ja) |
JP (1) | JP5329084B2 (ja) |
CN (1) | CN1980987B (ja) |
AT (1) | ATE544812T1 (ja) |
GB (1) | GB0415001D0 (ja) |
TW (1) | TWI374901B (ja) |
WO (1) | WO2006014229A1 (ja) |
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WO2021002668A1 (ko) * | 2019-07-02 | 2021-01-07 | 주식회사 케이씨씨 | 아미노 실리콘 폴리머, 이를 포함하는 실리콘 에멀젼 및 이의 제조방법 |
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CA2604751A1 (en) * | 2005-04-20 | 2006-12-28 | Laboratoires Mauves Inc. | Organic silicic acids complex for therapeutic and cosmetic applications |
US8074581B2 (en) | 2007-10-12 | 2011-12-13 | Steelcase Inc. | Conference table assembly |
US8268975B2 (en) * | 2009-04-03 | 2012-09-18 | Dow Agrosciences Llc | Demulsification compositions, systems and methods for demulsifying and separating aqueous emulsions |
DE102012207062A1 (de) * | 2012-04-27 | 2013-10-31 | Wacker Chemie Ag | Verfahren zur Herstellung von Aminogruppen aufweisenden Organosiliciumverbindungen |
US10441527B2 (en) | 2015-04-08 | 2019-10-15 | Dow Silicones Corporation | Fluid compositions and personal care |
CN111183178B (zh) * | 2018-05-31 | 2022-12-09 | 美国陶氏有机硅公司 | 使用可移除酸催化剂制备氨基官能聚二有机硅氧烷的方法 |
US11028233B2 (en) | 2018-05-31 | 2021-06-08 | Dow Silicones Corporation | Method for making an amino-functional polydiorganosiloxane using a removable solid catalyst |
US11603435B2 (en) * | 2019-02-18 | 2023-03-14 | Dow Silicones Corporation | Hydrophilic polysiloxane elastomer |
WO2023192727A1 (en) | 2022-03-29 | 2023-10-05 | Dow Silicones Corporation | Preparation of an amino-functional polyorganosiloxane emulsion |
Family Cites Families (9)
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US3575917A (en) | 1969-03-28 | 1971-04-20 | Dow Corning | Method of stabilizing catalyzed organopolysiloxanes |
GB1306680A (en) | 1969-11-28 | 1973-02-14 | Dow Corning Ltd | Organopolysiloxane compositions |
JPS62232459A (ja) * | 1986-04-02 | 1987-10-12 | Shin Etsu Chem Co Ltd | 室温硬化性オルガノポリシロキサン組成物 |
GB9515616D0 (en) | 1995-07-29 | 1995-09-27 | Dow Corning | Process of stabilising siloxane polymers |
GB9702234D0 (en) * | 1997-02-04 | 1997-03-26 | Dow Corning | Process for stabilising siloxane polymers |
DE19752659A1 (de) * | 1997-11-27 | 1999-06-24 | Wacker Chemie Gmbh | Organosiliciumverbindungenhaltige hydrophobierende Pulver enthaltende Baustoffmassen |
JP3959580B2 (ja) * | 1999-06-25 | 2007-08-15 | 信越化学工業株式会社 | 窒素原子含有ポリシロキサン、その製造方法及び繊維処理剤組成物 |
GB0120058D0 (en) | 2001-08-17 | 2001-10-10 | Dow Corning | Polysiloxanes and their preparation |
DE10259613A1 (de) * | 2002-12-19 | 2004-07-08 | Wacker-Chemie Gmbh | Organopolysiloxanzusammensetzungen und deren Einsatz in bei Raumtemperatur vernetzbaren niedermoduligen Massen |
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- 2005-06-17 JP JP2007520324A patent/JP5329084B2/ja active Active
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WO2021002668A1 (ko) * | 2019-07-02 | 2021-01-07 | 주식회사 케이씨씨 | 아미노 실리콘 폴리머, 이를 포함하는 실리콘 에멀젼 및 이의 제조방법 |
KR20210003597A (ko) * | 2019-07-02 | 2021-01-12 | 주식회사 케이씨씨 | 아미노 실리콘 폴리머, 이를 포함하는 실리콘 에멀젼 및 이의 제조방법 |
KR102273810B1 (ko) * | 2019-07-02 | 2021-07-06 | 주식회사 케이씨씨실리콘 | 아미노 실리콘 폴리머, 이를 포함하는 실리콘 에멀젼 및 이의 제조방법 |
Also Published As
Publication number | Publication date |
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WO2006014229A1 (en) | 2006-02-09 |
EP1776413B1 (en) | 2012-02-08 |
TW200619275A (en) | 2006-06-16 |
ATE544812T1 (de) | 2012-02-15 |
EP1776413A1 (en) | 2007-04-25 |
TWI374901B (en) | 2012-10-21 |
US7781505B2 (en) | 2010-08-24 |
CN1980987A (zh) | 2007-06-13 |
JP2008511688A (ja) | 2008-04-17 |
CN1980987B (zh) | 2012-01-04 |
GB0415001D0 (en) | 2004-08-04 |
US20070299178A1 (en) | 2007-12-27 |
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