JP5090623B2 - 制御可能な硬化速度を有するアルコキシシラン末端ポリマーをベースとするポリマー材料 - Google Patents
制御可能な硬化速度を有するアルコキシシラン末端ポリマーをベースとするポリマー材料 Download PDFInfo
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- JP5090623B2 JP5090623B2 JP2004533335A JP2004533335A JP5090623B2 JP 5090623 B2 JP5090623 B2 JP 5090623B2 JP 2004533335 A JP2004533335 A JP 2004533335A JP 2004533335 A JP2004533335 A JP 2004533335A JP 5090623 B2 JP5090623 B2 JP 5090623B2
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- 229920000642 polymer Polymers 0.000 title claims abstract description 67
- 239000000463 material Substances 0.000 title claims description 23
- 239000003054 catalyst Substances 0.000 claims abstract description 41
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 230000003213 activating effect Effects 0.000 claims abstract description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 36
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims description 28
- 239000002861 polymer material Substances 0.000 claims description 25
- -1 aromatic amine hydrochloride Chemical class 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 10
- BUZRAOJSFRKWPD-UHFFFAOYSA-N isocyanatosilane Chemical compound [SiH3]N=C=O BUZRAOJSFRKWPD-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000000565 sealant Substances 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
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- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 4
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- 125000003277 amino group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
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- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
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- QRFPECUQGPJPMV-UHFFFAOYSA-N isocyanatomethyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CN=C=O QRFPECUQGPJPMV-UHFFFAOYSA-N 0.000 description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VNBLTKHUCJLFSB-UHFFFAOYSA-N n-(trimethoxysilylmethyl)aniline Chemical compound CO[Si](OC)(OC)CNC1=CC=CC=C1 VNBLTKHUCJLFSB-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
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- 238000000197 pyrolysis Methods 0.000 description 3
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- 150000003335 secondary amines Chemical class 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
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- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
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- LGBAGUMSAPUZPU-UHFFFAOYSA-N bis(9-methyldecyl) benzene-1,2-dicarboxylate Chemical compound CC(C)CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCC(C)C LGBAGUMSAPUZPU-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
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- 238000002329 infrared spectrum Methods 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
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- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 1
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-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
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- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical class CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000012855 volatile organic compound Substances 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/336—Polymers modified by chemical after-treatment with organic compounds containing silicon
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/288—Compounds containing at least one heteroatom other than oxygen or nitrogen
- C08G18/289—Compounds containing at least one heteroatom other than oxygen or nitrogen containing silicon
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/71—Monoisocyanates or monoisothiocyanates
- C08G18/718—Monoisocyanates or monoisothiocyanates containing silicon
Description
−A−CH2−SiR1 a(OR2)3−a (1)
[式中、
Aは、−O−CO−N(R3)−、−N(R3)−CO−O−、−N(R3)−CO−NH−、−NH−CO−N(R3)−、−N(R3)−CO−N(R3)−から選択された二価の結合基を表し、
R1は、場合によりハロゲン置換された、炭素原子1〜10個を有するアルキル基、シクロアルキル基、アルケニル基またはアリール基を表し、
R2は、炭素原子1〜6個を有するアルキル基または全体で炭素原子2〜10個を有するオキサアルキル−アルキル基を表し、
R3は、水素、場合によりハロゲン置換された、環式、線状または分枝のC1〜C18−アルキル基またはアルケニル基またはC6〜C18−アリール基を表し、
aは、0〜2の整数を表す]の末端基(1)を有するアルコキシシラン末端ポリマーを含有するポリマー混合物は明らかに有利である。
NH(R3)−CH2−SiR1 a(OR2)3−a (2)
[式中、
R3は、水素または立体的にあまり大きくない基、例えばシクロヘキシル基またはn−ブチル基を表し、
R1、R2およびaは、前記の意味を表す]のアミノアルキルシランのみが使用されたという事実である。
−A−CH2−SiR1 a(OR2)3−a (1)
[式中、
A、R1、R2およびaは前記のものを表す]の末端基を有するアルコキシシラン末端ポリマー(P)を含有し、その際
a)このポリマー材料(M)が、23℃で相対湿度50%で、表皮形成時間>40分間を有し、かつ
b)3質量%までの濃度で触媒(K)を添加することにより、このポリマー材料(M)の表皮形成時間を<20分間に短縮することができる、ポリマー材料(M)である。
NH(フェニル)−CH2−SiR1 a(OR2)3−a (3)
[式中、
R1、R2およびaは、前記の意味を表す]のアミノシラン(A1)であるのが特に有利である。
Cl−CH2−SiR1 a(OR2)3−a (4)
[式中、R1、R2およびaは前記のものと同じ意味を有する]のクロロシランから製造される一般式(3)のシラン(A1)に関しても同じことが言える。
OCN−CH2−SiR1 a(OR2)3−a (5)
[式中、
R1、R2およびaは、前記の意味を表す]のイソシアナトシラン(B1)を使用する。
Z−R5−[Si(R4)2−O−]n−Si(R4)2−R5−Z (7)
[式中、
R4は、炭素原子1〜12個を有する一価の炭化水素基、有利にメチル基を表し、
R5は、炭素原子1〜12個を有する分枝のまたは非分枝の二価の炭化水素基、有利にトリメチレン基を表し、
nは、1〜3000、有利に10〜1000の数値を表し、
Zは、OH−、SH−またはNHR3−基を表す]の化合物を使用するのが有利である。
R7R8N−R6−SiR1 a(OR2)3−a (8)
[式中、
R6は、分枝または非分枝の、炭素原子1〜10個を有する、二価の炭化水素基を表し、これは場合により酸素またはN(R3)−基により中断されていてよく、
R7およびR8は、水素、炭素原子1〜20個を有する分枝または非分枝のアルキル基を表し、このアルキル基はハロゲン原子、ヒドロキシ基、アミノ基、モノアルキルアミノ基、ジアルキルアミノ基またはアルコキシ基により置換されていてもよく、
R1、R2、R3およびaは前記の意味を有する]の化合物を使用する。
メチルカルバメートメチル−トリメトキシシランを石英綿で充填されている石英熱分解管中に、アルゴン気流中でポンプを用いて供給する。熱分解管中の温度は420〜470℃である。粗生成物を加熱した区間の末端で冷却器を用いて凝縮させ、収集する。黄色〜褐色の液体を減圧下に蒸留により精製する。所望の生成物は約88〜90℃(82ミリバール)で塔頂部を介して99%を越える純度で留出し、一方塔底部に未反応のカルバメートが再単離する。これを熱分解中に再び直接返流する。
アニリン537g(5.77mol)を実験室用反応器中に完全に装入し、引き続き窒素で不活性化する。温度を115℃に加熱し、クロロメチル−トリメトキシシラン328g(1.92mol)を1.5時間かけて滴加し、更に125〜130℃で30分間後攪拌する。シラン約150gを添加した後、増加したアニリン塩酸塩が塩として析出するが、この懸濁液は配量終了まで十分に撹拌可能に保持される。
平均分子量8000g/molを有するポリプロピレングリコール400g(50.0mmol)を装入し、真空中、100℃で1時間脱水し、イソホロンジイソシアネート5.5g(25mmol)と100℃で60分間以内に重合する。得られたOH−末端ポリウレタンプレポリマーを、その後60℃に冷却し、イソシアナトメチルトリメトキシシラン9.8g(110mmol)と混合し、IR−スペクトル中にイソシアネートのバンドが存在しなくなるまで60分間撹拌する。20℃で85Pasの粘度を有する澄んで透明なポリマーが得られる。
平均分子量8000g/molを有するポリプロピレングリコール400g(50.0mmol)を装入し、真空中、100℃で1時間脱水し、イソホロンジイソシアネート5.5g(25mmol)と100℃で60分間以内に重合する。得られたOH−末端ポリウレタンプレポリマーを、その後60℃に冷却し、イソシアナトメチル−メチルジメトキシシラン8.9g(55mmol)と混合し、IR−スペクトル中にイソシアネートのバンドが存在しなくなるまで60分間撹拌する。20℃で77Pasの粘度を有する澄んで透明なポリマーが得られる。
平均分子量45000g/molを有するα,ω−(3−アミノプロピル)−ポリジメチルシロキサン500g(11.1mmol)を、真空ポンプを備える加熱可能な実験室用遊星型ミキサー中で80℃に加熱し、真空中で0.5時間加熱する。引き続き、イソシアナトメチル−トリメトキシシラン3.9g(22.2mmol)を80℃で添加し、更に1時間撹拌する。IR−スペクトル法によりNCO−バンドによりシランの完全な変換を追跡する。得られたシラン末端ポリマーを撹拌下に25℃に冷却し、粘度100Pasを有するトリメチルシリル末端ポリジメチルシロキサン230.0g、ビニルトリメトキシシラン20.0g、親水性熱分解珪酸85.0gと混合し、0.5時間以内に流れない高粘性ペーストにする。このようにして得られるペーストは2時間を越える表皮形成時間(23℃、50%rh)を示す。更に、3−(2−アミノエチル)−アミノプロピルトリメトキシシラン8.0gを触媒として添加することにより、空中での表皮形成時間は約5分間未満を示す(23℃、50%rh)。
平均分子量8000g/molを有するポリプロピレングリコール400g(50.0mmol)を装入し、真空中、100℃で1時間脱水し、イソシアナトメチル−トリメトキシシラン19.5g(110mmol)と混合し、IR−スペクトル中にイソシアネートのバンドが存在しなくなるまで60分間撹拌する。8.5Pasの粘度を有する澄んで透明なポリマーが得られる。
例3により製造したポリマーをそれぞれ塩基性化合物(第1表参照)0.5%と混合し、23℃、50%rhでの表皮形成時間を測定する。
撹拌手段、冷却手段および加熱手段を備える250ml反応容器中に、平均分子量425g/molのポリプロピレングリコール30g(70.6mmol)を装入し、100℃に1時間加熱することにより膜ポンプ真空で脱水する。引き続き、約50℃に冷却し、この温度で、窒素雰囲気下にトルエン−2,4−ジイソシアネート(TDI)24.6g(141.2mmol)を、その際この温度が80℃を越えないように添加する。添加の終了後、80℃で15分間撹拌する。
例5と同様に実施するが、2,2−ジモルホリノジエチルエーテルの添加を行わない。
その際、同様に50℃で約18Pasの粘度を有する澄んで透明なプレポリマー混合物が得られる。しかしながら、この表皮形成時間<1分間(23℃、50%rh)を有するプレポリマー混合物は著しく反応性である。保護ガス下にのみ操作性であり、注ぎ移し可能で、かつ/またはその他の成分とコンパウンディング可能である。更に、気密の容器においてのみ貯蔵安定である。この容器の開封後は直ぐに表皮形成に導く。
Claims (9)
- 次の成分1)及び2):
1)一般式(1)
−A−CH2−SiR1 a(OR2)3−a (1)
[式中、
Aは、−O−CO−NH−及び−NH−CO−NH−(イソシアナトシラン(B1)の使用の場合)、又は、−NH−CO−N(R3)−(アミノシラン(A1)の使用の場合)から選択された二価の結合基を表し、
R1は、非置換またはハロゲン置換された、炭素原子1〜10個を有するアルキル基、シクロアルキル基、アルケニル基またはアリール基を表し、
R2は、炭素原子1〜6個を有するアルキル基または全体で炭素原子2〜10個を有するω−オキサアルキル−アルキル基を表し、
R3は、C6〜C18−アリール基を表し、
aは、0〜1の整数を表す]の末端基を有し、
一般式(2)
NH(R3)−CH2−SiR1 a(OR2)3−a (2)
[式中、
R1、R2およびaは、上記の意味を表し、かつ
R3は、C6−〜C18−アリール基を表す]のアミノシラン(A1)又は、
一般式(5)
OCN−CH2−SiR1 a(OR2)3−a (5)
[式中、
R1、R2およびaは、上記の意味を表す]のイソシアナトシラン(B1)を使用することにより得られるアルコキシシラン末端ポリマー(P)を含有するポリマー材料(M)、但し、(A1)を使用する場合には、ポリマー材料(M)は、付加的に、立体障害を有する脂肪族アミンを0.001〜3質量%の量で含有するとの条件付きである、
その際
a)このポリマー材料(M)が、23℃で相対空中湿度50%で、表皮形成時間>40分間を有し、かつ
b)触媒(K)を3質量%までの濃度で添加することにより、このポリマー材料(M)の表皮形成時間を<20分間に短縮することができる、及び
2)触媒(K)
その際、触媒(K)が有機アミノ化合物である、
を含有するコンパウンド。 - ポリマー材料(M)が、立体障害を有さない塩基、立体障害を有さない酸および芳香族アミン塩酸塩から選択される活性化化合物(AV)を、ポリマー材料(M)の全質量に対して多くても100ppm含有する、請求項1記載のコンパウンド。
- ポリマー材料(M)が、立体障害を有さない塩基、立体障害を有さない酸および芳香族アミン塩酸塩から選択される活性化化合物(AV)を含有しない、請求項1記載のコンパウンド。
- 使用したアミノシラン(A1)がクロリド含量<20ppmである、請求項1記載のコンパウンド。
- 使用したアミノシラン(A1)がアニリン塩酸塩誘導体を含有しない、請求項1記載のコンパウンド。
- 立体障害を有する脂肪族アミンがN−アルキル化モルホリン誘導体である、請求項1記載のコンパウンド。
- 触媒(K)が一般式(8)
R7R8N−R6−SiR1 a(OR2)3−a (8)
[式中、
R6は、分枝または非分枝の、炭素原子1〜10個を有する、二価の炭化水素基を表し、これは中断されていないか、または酸素またはN(R3)−基により中断されていてよく、
R7およびR8は、水素または炭素原子1〜20個を有する分枝または非分枝のアルキル基を表し、このアルキル基は置換されていないか、またはハロゲン原子、ヒドロキシ基、アミノ基、モノアルキルアミノ基、ジアルキルアミノ基またはアルコキシ基により置換されており、
R1、R2、R3およびaは前記の意味を有する]の化合物である、請求項1から6までのいずれか1項記載のコンパウンド。 - 触媒(K)をポリマー材料(M)に添加し、前記触媒(K)が有機アミノ化合物である、請求項1から7までのいずれか1項記載のポリマー材料(M)の表皮形成法。
- 接着剤、シーリング剤、および目地シーリング材、取付フォーム、表面コーティングの分野並びに成形部材の製造のための、請求項1から7までのいずれか1項記載のコンパウンドの使用。
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JP2007204502A (ja) * | 2006-01-05 | 2007-08-16 | Konishi Co Ltd | 硬化性シリコーン系樹脂組成物 |
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DE102006059473A1 (de) * | 2006-12-14 | 2008-06-19 | Henkel Kgaa | Silylgruppen enthaltende Mischung von Prepolymeren und deren Verwendung |
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-
2002
- 2002-08-14 DE DE10237271A patent/DE10237271A1/de not_active Withdrawn
-
2003
- 2003-08-07 AU AU2003255396A patent/AU2003255396A1/en not_active Abandoned
- 2003-08-07 EP EP03793700A patent/EP1529071B1/de not_active Expired - Lifetime
- 2003-08-07 JP JP2004533335A patent/JP5090623B2/ja not_active Expired - Lifetime
- 2003-08-07 WO PCT/EP2003/008782 patent/WO2004022618A1/de active IP Right Grant
- 2003-08-07 US US10/524,473 patent/US7332541B2/en not_active Expired - Lifetime
- 2003-08-07 AT AT03793700T patent/ATE330979T1/de not_active IP Right Cessation
- 2003-08-07 CN CNB038195038A patent/CN100349944C/zh not_active Expired - Lifetime
- 2003-08-07 ES ES03793700T patent/ES2268476T3/es not_active Expired - Lifetime
- 2003-08-07 DE DE50303977T patent/DE50303977D1/de not_active Expired - Lifetime
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US7332541B2 (en) | 2008-02-19 |
EP1529071A1 (de) | 2005-05-11 |
EP1529071B1 (de) | 2006-06-21 |
JP2005535779A (ja) | 2005-11-24 |
DE50303977D1 (de) | 2006-08-03 |
CN100349944C (zh) | 2007-11-21 |
DE10237271A1 (de) | 2004-03-04 |
ATE330979T1 (de) | 2006-07-15 |
CN1675275A (zh) | 2005-09-28 |
ES2268476T3 (es) | 2007-03-16 |
US20060111505A1 (en) | 2006-05-25 |
AU2003255396A1 (en) | 2004-03-29 |
WO2004022618A1 (de) | 2004-03-18 |
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