EP1926739A1 - Composition d'organoalcoxysilane stabilisee par des tensioactifs - Google Patents
Composition d'organoalcoxysilane stabilisee par des tensioactifsInfo
- Publication number
- EP1926739A1 EP1926739A1 EP06806742A EP06806742A EP1926739A1 EP 1926739 A1 EP1926739 A1 EP 1926739A1 EP 06806742 A EP06806742 A EP 06806742A EP 06806742 A EP06806742 A EP 06806742A EP 1926739 A1 EP1926739 A1 EP 1926739A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- group
- organoalkoxysilane
- atoms
- weight
- formula
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 46
- 239000004094 surface-active agent Substances 0.000 claims abstract description 36
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 230000001070 adhesive effect Effects 0.000 claims description 14
- 239000007795 chemical reaction product Substances 0.000 claims description 14
- 239000000853 adhesive Substances 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 10
- 229910000077 silane Inorganic materials 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 6
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- 125000000524 functional group Chemical group 0.000 claims description 6
- 239000002736 nonionic surfactant Substances 0.000 claims description 5
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
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- 238000002360 preparation method Methods 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- -1 siloxane compounds Chemical class 0.000 description 17
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- 238000002156 mixing Methods 0.000 description 8
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- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 6
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- 229910052710 silicon Inorganic materials 0.000 description 5
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- ZYAASQNKCWTPKI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propan-1-amine Chemical compound CO[Si](C)(OC)CCCN ZYAASQNKCWTPKI-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- RSCUJJZVNRPPQH-UHFFFAOYSA-N 4-(dimethoxymethylsilyl)-2,2-dimethylbutan-1-amine Chemical compound COC(OC)[SiH2]CCC(C)(C)CN RSCUJJZVNRPPQH-UHFFFAOYSA-N 0.000 description 2
- NHIDUYBCYBGHAX-UHFFFAOYSA-N 4-(dimethoxymethylsilyl)butan-1-amine Chemical compound COC(OC)[SiH2]CCCCN NHIDUYBCYBGHAX-UHFFFAOYSA-N 0.000 description 2
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- XWSNOMORVOQOKF-UHFFFAOYSA-N COC(OC)[SiH2]CN Chemical compound COC(OC)[SiH2]CN XWSNOMORVOQOKF-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 241001503177 Rio Segundo hantavirus Species 0.000 description 2
- 229910008051 Si-OH Inorganic materials 0.000 description 2
- 229910006358 Si—OH Inorganic materials 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 239000002563 ionic surfactant Substances 0.000 description 2
- BUZRAOJSFRKWPD-UHFFFAOYSA-N isocyanatosilane Chemical class [SiH3]N=C=O BUZRAOJSFRKWPD-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- NHBRUUFBSBSTHM-UHFFFAOYSA-N n'-[2-(3-trimethoxysilylpropylamino)ethyl]ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCNCCN NHBRUUFBSBSTHM-UHFFFAOYSA-N 0.000 description 2
- 125000005375 organosiloxane group Chemical group 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 125000005372 silanol group Chemical group 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 2
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 2
- ARKBFSWVHXKMSD-UHFFFAOYSA-N trimethoxysilylmethanamine Chemical compound CO[Si](CN)(OC)OC ARKBFSWVHXKMSD-UHFFFAOYSA-N 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
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- INJVFBCDVXYHGQ-UHFFFAOYSA-N n'-(3-triethoxysilylpropyl)ethane-1,2-diamine Chemical compound CCO[Si](OCC)(OCC)CCCNCCN INJVFBCDVXYHGQ-UHFFFAOYSA-N 0.000 description 1
- SMIDUPHNWFRONB-UHFFFAOYSA-N n,2-dimethyl-3-trimethoxysilylpropan-1-amine Chemical compound CNCC(C)C[Si](OC)(OC)OC SMIDUPHNWFRONB-UHFFFAOYSA-N 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- XCOASYLMDUQBHW-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)butan-1-amine Chemical compound CCCCNCCC[Si](OC)(OC)OC XCOASYLMDUQBHW-UHFFFAOYSA-N 0.000 description 1
- KGNDVXPHQJMHLX-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)cyclohexanamine Chemical compound CO[Si](OC)(OC)CCCNC1CCCCC1 KGNDVXPHQJMHLX-UHFFFAOYSA-N 0.000 description 1
- OPNZRGZMQBXPTH-UHFFFAOYSA-N n-(4-trimethoxysilylbutyl)aniline Chemical compound CO[Si](OC)(OC)CCCCNC1=CC=CC=C1 OPNZRGZMQBXPTH-UHFFFAOYSA-N 0.000 description 1
- FRDNYWXDODPUJV-UHFFFAOYSA-N n-ethyl-2-methyl-3-trimethoxysilylpropan-1-amine Chemical compound CCNCC(C)C[Si](OC)(OC)OC FRDNYWXDODPUJV-UHFFFAOYSA-N 0.000 description 1
- FYZBRYMWONGDHC-UHFFFAOYSA-N n-ethyl-3-trimethoxysilylpropan-1-amine Chemical compound CCNCCC[Si](OC)(OC)OC FYZBRYMWONGDHC-UHFFFAOYSA-N 0.000 description 1
- DVYVMJLSUSGYMH-UHFFFAOYSA-N n-methyl-3-trimethoxysilylpropan-1-amine Chemical compound CNCCC[Si](OC)(OC)OC DVYVMJLSUSGYMH-UHFFFAOYSA-N 0.000 description 1
- RPMXALUWKZHYOV-UHFFFAOYSA-N nitroethene Chemical group [O-][N+](=O)C=C RPMXALUWKZHYOV-UHFFFAOYSA-N 0.000 description 1
- SLYCYWCVSGPDFR-UHFFFAOYSA-N octadecyltrimethoxysilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OC)(OC)OC SLYCYWCVSGPDFR-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000001283 organosilanols Chemical class 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- VYHWVLSMXFMGPI-UHFFFAOYSA-N trimethoxy(3-methylbutyl)silane Chemical compound CO[Si](OC)(OC)CCC(C)C VYHWVLSMXFMGPI-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- PIAOLBVUVDXHHL-VOTSOKGWSA-N β-nitrostyrene Chemical compound [O-][N+](=O)\C=C\C1=CC=CC=C1 PIAOLBVUVDXHHL-VOTSOKGWSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- 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
Definitions
- the invention relates to the field of organoalkoxysilanes.
- Organoalkoxysilane are known substances and have long been used for example as adhesion promoters. They are often referred to by the skilled person as silanes. They have alkoxysilane groups which hydrolyze in contact with water in liquid form or as atmospheric moisture to form a silanol group (Si-OH) and then can crosslink to siloxane compounds. This can lead to precipitations or cloudiness appearing after a very short time. This sensitivity is particularly pronounced in polar organoalkoxysilanes, as well as at basic pH, and therefore particularly aminosilanes.
- organoalkoxysilanes care when handling organoalkoxysilanes care must be taken that they are stored and processed in the absence of moisture. This often leads to difficulties in practice, for example, when a package is not tight or was opened and badly closed.
- the object of the present invention is therefore to improve the storage stability of organoalkoxysilanes and in particular to improve the sensitivity of the organoalkoxysilanes to water, in particular to atmospheric moisture. Surprisingly, it was found that the
- Organoalkoxysilane according to claim 1 can achieve this object.
- the present invention relates to organoalkoxysilane compositions containing at least one organoalkoxysilane S and at least one anhydrous surfactant T, wherein the weight fraction of all organoalkoxysilanes S ⁇ 33 wt .-%, based on the weight of the Organoalkoxysilanzusam- composition and wherein the ratio the sum by weight of all organoalkoxysilanes S for the sum by weight of all anhydrous surfactants T (ST) has a value of 5: 1 to 1: 2.
- organoalkoxysilane or “silane” for short in this document refers to compounds in which at least one, usually two or three alkoxy groups are bonded directly to the silicon atom (via a Si-O bond), and the on the other hand at least one directly to the silicon atom (via an Si-C bond) bonded organic radical and have no Si-O-Si bonds.
- silane group denotes the silicon-containing group bonded to the organic radical of the organoalkoxysilane
- organoalkoxysilanes, or their silane groups have the property of hydrolyzing on contact with moisture, forming organosilanols, ie organosilicon compounds containing one or more silanol groups (Si-OH groups) and, by means of subsequent condensation reactions, organosiloxanes, that is to say organosiloxanes containing one or more siloxane groups (Si-O-Si-groups)
- si-OH groups silanol groups
- si-O-Si-groups organosiloxanes containing one or more siloxane groups
- Mercaptosilane refers to silanes which have the corresponding functional group, in this case an aminoalkylalkoxysilane, epoxyalkylalkoxysilane, alkylalkoxysilane and mercaptoalkylalkoxysilane.
- anhydrous in this document is not to be construed as “absolutely free of water”. There are therefore also compounds and
- compositions referred to as “anhydrous" which contain minor traces of
- Contain water i. which contain a residual water content of at most 1% by weight, in particular of at most 0.5% by weight.
- Organoalkoxysilanes S are, in particular, aminosilanes, epoxysilanes, mercaptosilanes and alkylsilanes.
- Aminosilanes are, in particular, aminosilanes of the formula (I) or
- Reaction products of the formula (I) which has at least one secondary or primary amino group with a compound (ARV) which contains at least one functional group which can react with a primary or secondary amino group.
- R 1 is an alkyl group having 1 to 8 C atoms, preferably a methyl or an ethyl group.
- R 1 is preferably a methyl group.
- R 2 is an alkyl group having 1 to 5 C atoms, preferably a methyl group or an ethyl group or an isopropyl group.
- R 2 is preferably a methyl group or an ethyl group.
- R 3 is a linear or branched alkylene group having 1 to 4 carbon atoms.
- R 3 is preferably a propylene group.
- R 4 is H or a linear or branched alkyl group having 1 to 10 C atoms or a substituent of the formula (II)
- R is H or a linear or branched alkyl group having 1 to 10 C atoms or a linear or branched alkyl group having 1 to 10 C atoms with further hetero atoms or for a substituent of the formula (II)
- a particularly advantageous radical of a linear alkyl group having 1 to 10 C atoms with further heteroatoms R 5 is the radical CH 2 CH 2 NH 2 .
- the subscript a stands for a value 0, 1 or 2, in particular for 0 or 1.
- a stands for 0.
- aminosilanes of the formula (I) are 3-aminopropyltrimethoxysilane, 3-aminopropyldimethoxymethylsilane, 3-amino-2-methylpropyltrimethoxysilane, 4-aminobutyltrimethoxysilane, 4-aminobutyldimethoxymethylsilane, 4-aminobutyldimethoxymethylsilane, 3-methylbutyltrimethoxysilane, 4-amino-3,3-dimethylbutyltrimethoxysilane, 4-amino-3,3-dimethylbutyldimethoxymethylsilane, 2-aminoethylthymethoxysilane, 2-aminoethyldimethoxymethylsilane, aminomethyltrimethoxysilane, Aminomethyldimethoxymethylsilane, aminomethylmethoxymethylsilane, N-methyl-3-aminopropyltrimethoxysilane, aminomethyl
- Preferred aminosilanes of the formula (I) are aminosilanes which are selected from the group comprising aminosilanes of the formula (III), (IV) and (V).
- the most preferred aminosilanes of the formula (I) are the aminosilanes 3-aminopropyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, 3- [2- (2-aminoethylamino) ethylamino] -propyl- trimethoxysilane, bis (trimethoxysilylpropyl) amine and tris (trimethoxysilylpropyl) amine.
- the aminosilane is a reaction product of an aminosilane of formula (I), as described above, having at least one secondary or primary amino group, with a compound (ARV) having at least one functional group which is substituted with a primary or secondary amino group can react.
- This functional group which can react with a primary or secondary amino group, is preferably an epoxy group. But there are also other groups, such as isocyanate groups or activated double bonds, conceivable. Particularly suitable compounds with epoxy groups are epoxysilanes.
- Preferred compounds (ARV) which can react with the aminosilane of the formula (I) with at least one secondary or primary amino group are epoxysilanes of the formula (VI)
- R 1 here stands for an alkyl group having 1 to 8 C atoms, preferably a methyl or an ethyl group.
- R 2 is an alkyl group having 1 to 5 carbon atoms.
- R 3 is a linear or branched Alkylene group having 1 to 4 carbon atoms and a 'for 0, 1 or 2, in particular for 0 or 1.
- R 1 is in particular a methyl group.
- R 2 is preferably a methyl group or an ethyl group or an isopropyl group. As particularly preferred, R 2 is a methyl group or an ethyl group.
- R 3 is preferably propylene.
- the index a ' preferably stands for 0.
- epoxysilanes are 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltriethoxysilane, 3-glycidyloxypropyltriethoxysilane and 3-glycidyloxypropyltrimethoxysilane.
- Preferred epoxysilanes are 3-glycidyloxypropyltriethoxysilane and 3-glycidyloxypropyltrimethoxysilane.
- the most preferred epoxy silane is 3-glycidyloxypropyltrimethoxysilane.
- the aminosilane of the formula (I) which is used for the reaction product are, in addition to N- (2-aminoethyl) -3-aminopropyltrimethoxysilane and N- (2-aminoethyl) -3-aminopropyltriethoxysilane, preferably N- (2 Aminopropyl) -3-aminopropyltrimethoxysilane, in particular aminosilanes of the formula (III) or (IV), in particular 3-aminopropyltrimethoxysilane, bis (trimethoxysilylpropyl) amine, 3-aminopropyltriethoxysilane and bis (triethoxysilylpropyl) amine. Preference is given to 3-aminopropyltrimethoxysilane and bis (thmethoxysilylpropyl) amine.
- reaction product may or may not have primary or secondary amino groups.
- reaction products are compounds of the formula (VII), (VIII), (IX), (X), (XI) and (XII).
- the compounds of formulas (VII), (VIII) and (IX) are obtained from the reaction of N- (2-aminoethyl) -3-aminopropyltrimethoxysilane and 3-glycidyloxypropyltrimethoxysilane.
- the compounds of formulas (X) and (XI) are obtained from the reaction of 3-aminopropyltrimethoxysilane and 3-glycidyloxypropyltrimethoxysilane.
- the compound of formulas (XII) is obtained from the reaction of bis (tri-methoxysilylpropyl) amine and 3-glycidyloxypropyltrimethoxysilane.
- amine-reactive compounds (ARV) with activated double bonds are, for example, ⁇ , ⁇ -unsaturated compounds, in particular maleic diesters, fumaric diesters, citraconic diesters, acrylic esters, methacrylic acid esters, cinnamic acid esters, itaconic diesters, vinylphosphonic diesters, vinylsulfonyl esters, vinylsulfones,
- reaction products are Michael adducts of 3-aminopropyltrimethoxysilane, 3-aminopropyldimethoxymethylsilane, 4-amino-3,3-dimethylbutyltrimethoxysilane, 4-amino-3,3-dimethylbutyldimethoxymethylsilane, aminomethyl- trimethoxysilane or aminomethyldimethoxymethylsilane with dimethyl, diethyl or dibutyl maleate, acrylate tetrahydrofurfuryl, isobornyl, hexyl, lauryl, stearyl, 2-hydroxyethyl or 3-hydroxypropyl ester, phosphonic acid dimethyl, diethyl or dibutyl ester, acrylonitrile, 2-pentenenitrile, fumaronitrile or ⁇ -nitrostyrene, as well as the analogues of said aminosilanes with ethoxy instead of the methoxy groups on the silicon.
- amine-reactive compounds (ARV) with isocyanate groups are isocyanatosilanes or polyisocyanates.
- Particular examples of isocyanatosilane are 3-isocyanatopropyltrimethoxysilane and 3-isocyanatopropyltriethoxysilane.
- polyisocyanates for example, 2,4- and 2,6-toluene diisocyanate (TDI) and any mixtures of these isomers, 4,4'-, 2,4'- and 2,2'-diphenylmethane diisocyanate (MDI) and any mixtures of these and others Isomers, 1, 3 and 1, 4-phenylene diisocyanate, 2,3,5,6-tetramethyl-1,4-diisocyanatobenzene, 1,6-hexamethylene diisocyanate (HDI), 2-methylpentamethylene-1,5-diisocyanate, 2,2,4- and 2,4,4-trimethyl-1,6-hexamethylene diisocyanate (TMDI), 1, 12-dodecamethylene diisocyanate, cyclohexane-1, 3- and - 1, 4-diisocyanate and any mixtures of these isomers , 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane
- organoalkoxysilane S is an epoxysilane
- the epoxysilanes as described above as amine reactive compounds (ARV) are to be preferred.
- mercaptosilane as organoalkoxysilane S are 3-mercaptopropyltrimethoxysilane and 3-mercaptopropyltriethoxysilane.
- organoalkoxysilane S is an alkylsilane
- silanes with C ⁇ alkyl may be mentioned such as methyltri- trimethoxysilane, ethyltrimethoxysilane and butyl trimethoxysilane.
- Aminosilanes are compared to epoxysilanes, mercaptosilanes and
- Alkyl silanes as Organoalkoxysilan S preferred.
- the organoalkoxysilanes S have in particular no chemical groups which can react with the surfactant T.
- surfactants T natural or synthetic substances can be used, which in solutions reduce the surface tension of the water or other liquids.
- Surfactants also called wetting agents, anionic, cationic, nonionic or ampholytic surfactants or mixtures thereof can be used.
- anionic surfactants are surfactants having carboxylate, sulfate, phosphate or sulfonate groups, such as, for example, amino acid derivatives, fatty alcohol ether sulfates, fatty alcohol sulfates, soaps, Alkylphenol ethoxylates, fatty alcohol ethoxylates, but also alkanesulfonates,
- Olefinsulfonates or alkyl phosphates Olefinsulfonates or alkyl phosphates.
- nonionic surfactants examples include ethoxylates, such as ethoxylated addition products of alcohols, for example polyoxyalkylene polyols,
- Amines fatty acids, fatty acid amides, alkylphenols, ethanolamides, fatty amines,
- Polysiloxanes or fatty acid esters but also alkyl or alkylphenyl polyglycol ethers, such as fatty alcohol polyglycol ethers, or
- Alkly groups can be completed.
- cationic surfactants are quaternary ammonium or
- Phosphonium compounds such as, for example, tetraalkylammonium salts, N-, N-dialkylimidazoline compounds, dimethyldistearylammonium compounds, or N-alkylpyridine compounds, in particular ammonium chlorides.
- ampholytic or amphoteric surfactants include amphoteric electrolytes, so-called ampholytes, such as
- Aminocarboxylic acids and betaines. Such surfactants are widely available commercially.
- nonionic surfactants especially alkoxylated alcohols.
- Alkoxylated nonionic fluorinated surfactants in particular Zonyl® FSO-100, which have been shown to be particularly suitable, have been found to be suitable
- Antarox FM 33 which is commercially available commercially from Rhodia.
- the surfactant must be anhydrous, as the introduction of significant amounts of water by the surfactant can lead to premature hydrolysis of the silanes and thus storage problems. To understand the term "anhydrous”, reference is made to the above definition.
- the ratio of organoalkoxysilane S to surfactant T in a certain ratio is observed. If the ratio S: T is greater than 5: 1, the sensitivity to water is not significantly improved. If this ratio is less than 1: 2, in particular less than 2: 3, the adhesion is increasingly adversely affected if the silane composition is used as an adhesion promoter.
- the optimum ratio of organoalkoxysilane S to surfactant T is, in particular for aminosilanes as organoalkoxysilane S, a value of 3: 1 to 2: 3.
- the organoalkoxysilane composition may contain other ingredients.
- additives are solvents, inorganic fillers, catalysts and stabilizers, dyes or pigments.
- the composition has not more than 1% by weight, in particular not more than 0.5% by weight, of water.
- the organoalkoxysilane composition is required to have not less than 33% by weight, more preferably not less than 40% by weight of organoalkoxysilane S.
- Substantially is understood here that the total weight of organoalkoxysilane S and surfactant T more than 90 wt .-%, in particular more than 95%, preferably more than 99 wt .-%, based on the weight of
- Alkylalkoxysilanes such as dodecyltrimethoxysilane or octadecyltrimethoxysilane, are not preferred as organoalkoxysilanes S.
- Organoalkoxysilanes S Organoalkoxysilanes S.
- the Organoalkoxysilanzusammen stuen especially if they contain aminosilanes as Organoalkoxysilane S, are significantly less sensitive to the influence of water during storage. This is particularly evident when water, especially in the form of atmospheric moisture, can come into contact with the Organoalkoxysilanzusammen appen.
- Reasons for such a contact for example, be leaky packaging. So it may well happen in practice that, for example, original packaging is not tight, or that a storage container after opening the first time bad or leaking is closed again or that it is exposed to the environment completely unsealed for a certain time.
- Sensitivity to water during storage is particularly evident in the absence or at least significant delay in the formation of precipitates or cloudiness.
- organoalkoxysilane compositions are described in particular as
- Adhesive used. These adhesion promoters may be part of compositions which must have good adhesion.
- organoalkoxysilane compositions as a component of adhesive or Sealants possible. Likewise, they can be used in coatings such as paints or floor coverings.
- the organoalkoxysilanes S can react covalently with reactive groups.
- aminosilanes of the formula (I) can be used to react with isocyanate group-containing prepolymers and to produce so-called silane-terminated polyurethanes (SPUR).
- Organoalkoxysilanzusammen stuen can be used as a pretreatment agent or part of a pretreatment agent to improve the adhesion of an applied adhesive or sealant.
- Such pretreatment agents are also often called
- Called primer Such a primer can be one or two-component.
- organoalkoxysilane compositions or a
- adhesives, sealants or coatings are in particular reactive, i. crosslinking adhesives, sealants or coatings, in particular based on isocyanate group-containing polyurethanes.
- aqueous two-component primers consisting of a component K1 and a component K2 are preferred as two-component primers.
- the first component K1 contains an organoalkoxysilane composition and the second component K2 contains water and an acid. It is preferred that after the mixing of component K1 and K2 a pH of 2-5, in particular 3.5-4.5, results.
- a primer composition can be mixed well by simple shaking and hydrolyzed rapidly while slowing the condensation and thus the formation of undesirable siloxanes. As a result, a very good adhesion is built up, without forming unwanted precipitation or turbidity between the mixing and the application of the aqueous primer. Examples
- reaction product RP1 was prepared from 3-glycidyloxypropyl-trimethoxysilane and N- (2-aminoethyl) -3-aminopropyltrimethoxysilane by mixing 1 mole of A1120 with 3 moles of A187. Immediately after mixing, the conversion could be checked with IR. The characteristic of the epoxy group band at about 910 cm "1 is still detectable immediately after mixing, but disappears quickly.
- the vessels filled in this way were closed with a lid and stored in a furnace (Ehret, TK / L 4061) with circulating air at 50 ° C.
- a furnace Ehret, TK / L 4061
- Table 3 shows the stability by specifying the number of days it took for the sample to gel. If, after the 30th day, the sample was still flawless, the value> 30 was given.
- reaction product RP1 already described was used. Furthermore, a reaction product RP2 was prepared from 3-glycidyloxypropyltrimethoxysilane and 3- [2- (2-aminoethylamino) ethylamino] propyltrimethoxysilane by mixing 1 mol of A1130 with 6.6 mol of A187.
- RP1 and RP2 were mixed with different surfactants in a mixing ratio ST of 2,125: 1, corresponding to a content of the organoalkoxysilane S of 68% by weight of the total weight of the entire composition, as previously described.
- the comparative test series Ref.S5 was carried out without the addition of surfactants, ie as pure organoalkoxysilanes.
- Organoalkoxysilane compositions of A1110 and various surfactants were prepared in the proportions shown in Table 6 and used as a first component K1 of an aqueous primer.
- the second component K2 consisted of water and 1 wt .-% acetic acid. 1.05 g of component K1 was added to 49 g of component K2 and shaken.
- the adhesion of the adhesive was tested by means of a 'bead test'. This is cut at the end just above the adhesive surface. The cut end of the caterpillar is held with a round tongs and pulled from the ground. This is done by carefully rolling up the bead on the pliers tip, as well as placing a cut perpendicular to the track pulling direction down to the bare ground. The caterpillar pull-off speed should be selected so that a cut must be made approx. Every 3 seconds. The test track must be at least 8 cm. The adhesive that remains after the removal of the caterpillar from the substrate (cohesive failure) is assessed. The assessment of the adhesive properties is carried out by estimating the cohesive part of the adhesive surface:
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- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Silicon Polymers (AREA)
- Sealing Material Composition (AREA)
Abstract
L'invention concerne des compositions d'organoalcoxysilane comprenant au moins un organoalcoxysilane (S), et au moins un tensioactif (T) anhydre. Selon l'invention, le pourcentage en poids de tous les organoalcoxysilanes (S) est = à 33 % en poids par rapport au poids de la composition d'organoalcoxysilane. En outre, le rapport entre la somme des pourcentages en poids de tous les organoalcoxysilanes (S) par rapport à la somme des pourcentages en poids de tous les tensioactifs anhydres (T) (S:T) correspond à une valeur comprise entre 5:1 et 1:2.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06806742A EP1926739A1 (fr) | 2005-09-02 | 2006-09-01 | Composition d'organoalcoxysilane stabilisee par des tensioactifs |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP05108070A EP1760084A1 (fr) | 2005-09-02 | 2005-09-02 | Composition contenant un organo-alkoxysilane stabilisé par un agent tensioactif |
EP06806742A EP1926739A1 (fr) | 2005-09-02 | 2006-09-01 | Composition d'organoalcoxysilane stabilisee par des tensioactifs |
PCT/EP2006/065915 WO2007026015A1 (fr) | 2005-09-02 | 2006-09-01 | Composition d'organoalcoxysilane stabilisee par des tensioactifs |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1926739A1 true EP1926739A1 (fr) | 2008-06-04 |
Family
ID=35542042
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP05108070A Withdrawn EP1760084A1 (fr) | 2005-09-02 | 2005-09-02 | Composition contenant un organo-alkoxysilane stabilisé par un agent tensioactif |
EP06806742A Withdrawn EP1926739A1 (fr) | 2005-09-02 | 2006-09-01 | Composition d'organoalcoxysilane stabilisee par des tensioactifs |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP05108070A Withdrawn EP1760084A1 (fr) | 2005-09-02 | 2005-09-02 | Composition contenant un organo-alkoxysilane stabilisé par un agent tensioactif |
Country Status (11)
Country | Link |
---|---|
US (1) | US8377191B2 (fr) |
EP (2) | EP1760084A1 (fr) |
JP (1) | JP5254791B2 (fr) |
KR (1) | KR20080042920A (fr) |
CN (1) | CN101305013A (fr) |
AU (1) | AU2006286513A1 (fr) |
BR (1) | BRPI0616124A2 (fr) |
CA (1) | CA2621020A1 (fr) |
RU (1) | RU2387660C2 (fr) |
WO (1) | WO2007026015A1 (fr) |
ZA (1) | ZA200801622B (fr) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101300382B1 (ko) * | 2008-03-21 | 2013-08-26 | 미쓰이 가가쿠 가부시키가이샤 | 친수막 |
DE102009019899A1 (de) | 2009-05-04 | 2010-11-11 | Fischerwerke Gmbh & Co. Kg | Klebstoffe auf Basis silanterminierter Isocyanate |
DE102010060443A1 (de) | 2010-11-09 | 2012-05-10 | Fischerwerke Gmbh & Co. Kg | Harz für Kleb- und Beschichtungsstoffe auf Basis silanterminierter Harze mit mindestens zwei Edukten |
DE102011084183A1 (de) * | 2011-03-25 | 2012-09-27 | Evonik Degussa Gmbh | Wässrige Korrosionsschutzformulierung auf Silanebasis |
CN105121584B (zh) | 2012-12-04 | 2017-09-26 | 汉高股份有限及两合公司 | 用于制备木质纤维素复合材料的粘合剂体系 |
US9649826B2 (en) | 2013-08-15 | 2017-05-16 | Henkel Ag & Co. Kgaa | Adhesive system for preparing lignocellulosic composites |
WO2015193208A2 (fr) * | 2014-06-16 | 2015-12-23 | Sika Technology Ag | Catalyseur de réticulation à motifs constitutifs siloxane |
JP6265160B2 (ja) * | 2015-03-30 | 2018-01-24 | セメダイン株式会社 | 1液型水性接着剤組成物 |
CN109021909B (zh) * | 2018-06-25 | 2021-04-20 | 福建华夏蓝新材料科技有限公司 | 一种低表面张力水性聚氨酯胶粘剂及其制备方法 |
US20230070559A1 (en) * | 2020-01-30 | 2023-03-09 | Panasonic Intellectual Property Management Co., Ltd. | Additive for nonaqueous electrolyte solutions, nonaqueous electrolyte solution containing same, and nonaqueous electrolyte secondary battery |
CN113136575B (zh) * | 2021-03-11 | 2022-08-05 | 首钢集团有限公司 | 一种用于改善锌铝镁镀钢胶接性能的钝化液及其制备方法 |
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US4306035A (en) * | 1980-05-30 | 1981-12-15 | Union Carbide Corporation | Use of alkoxysilicon compositions as foam stabilizers in high resilience polyurethane foams |
WO2001018128A2 (fr) * | 1999-08-20 | 2001-03-15 | The Walman Optical Company | Composition de revetement servant a produire des revetements anti-abrasifs pouvant etre teintes |
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FR2382792A1 (fr) * | 1977-03-04 | 1978-09-29 | Guimbal Jean | Moteur lineaire prismatique a grande vitesse et a tres grande puissance massique |
JPS6017230B2 (ja) | 1977-07-06 | 1985-05-01 | 三井フロロケミカル株式会社 | 含フツ素樹脂被膜の剥離強度増強用下塗り剤 |
US4174229A (en) * | 1978-03-28 | 1979-11-13 | Ppg Industries, Inc. | Magnesium oxide cementitious compositions containing hydrolyzable organo-silicon compounds |
US4374879A (en) | 1981-02-02 | 1983-02-22 | Celanese Corporation | Glass bottle coating composition made from a salt of a polyamine terminated polyepoxide adduct, an epoxy crosslinker, a reactive silane, a surfactant and a natural or synthetic wax |
US4874229A (en) * | 1987-03-31 | 1989-10-17 | Toyoda Gosei Co., Ltd. | Planar dimmer |
JPH0439345A (ja) | 1990-06-06 | 1992-02-10 | Kobayashi Kk | 塩化ビニル系プラスチゾル組成物 |
DE4122263C1 (fr) * | 1991-07-05 | 1993-02-25 | Degussa Ag, 6000 Frankfurt, De | |
US5354881A (en) * | 1991-10-15 | 1994-10-11 | Ppg Industries, Inc. | Silanes carrying water-solubilizing and hydrophobic moieties |
JPH05156164A (ja) * | 1991-12-04 | 1993-06-22 | Sumitomo Seika Chem Co Ltd | 吸水防止剤組成物およびそれを用いる吸水防止方法 |
US5363994A (en) * | 1992-06-26 | 1994-11-15 | Tremco, Inc. | Aqueous silane coupling agent solution for use as a sealant primer |
JP3245575B2 (ja) | 1999-05-12 | 2002-01-15 | エスケー化研株式会社 | 透湿性塗膜の形成方法 |
US6511752B1 (en) * | 2000-06-01 | 2003-01-28 | Sika Corporation | Water-based primer for promoting adhesion of polyurethane-based sealants and adhesives |
JP2002143765A (ja) * | 2000-11-14 | 2002-05-21 | Toray Ind Inc | 金属基材への塗装方法および塗装物品 |
JP2002220224A (ja) | 2001-01-23 | 2002-08-09 | Mitsui Chemicals Inc | 保存安定性に優れた多孔質シリカ形成用の前駆体溶液、および多孔質シリカの製造方法 |
-
2005
- 2005-09-02 EP EP05108070A patent/EP1760084A1/fr not_active Withdrawn
-
2006
- 2006-09-01 EP EP06806742A patent/EP1926739A1/fr not_active Withdrawn
- 2006-09-01 AU AU2006286513A patent/AU2006286513A1/en not_active Abandoned
- 2006-09-01 US US11/991,358 patent/US8377191B2/en not_active Expired - Fee Related
- 2006-09-01 CA CA002621020A patent/CA2621020A1/fr not_active Abandoned
- 2006-09-01 JP JP2008528531A patent/JP5254791B2/ja not_active Expired - Fee Related
- 2006-09-01 RU RU2008112665/04A patent/RU2387660C2/ru not_active IP Right Cessation
- 2006-09-01 KR KR1020087007973A patent/KR20080042920A/ko not_active Application Discontinuation
- 2006-09-01 WO PCT/EP2006/065915 patent/WO2007026015A1/fr active Application Filing
- 2006-09-01 CN CNA2006800316949A patent/CN101305013A/zh active Pending
- 2006-09-01 BR BRPI0616124-3A patent/BRPI0616124A2/pt not_active IP Right Cessation
- 2006-09-01 ZA ZA200801622A patent/ZA200801622B/xx unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4306035A (en) * | 1980-05-30 | 1981-12-15 | Union Carbide Corporation | Use of alkoxysilicon compositions as foam stabilizers in high resilience polyurethane foams |
WO2001018128A2 (fr) * | 1999-08-20 | 2001-03-15 | The Walman Optical Company | Composition de revetement servant a produire des revetements anti-abrasifs pouvant etre teintes |
Non-Patent Citations (1)
Title |
---|
See also references of WO2007026015A1 * |
Also Published As
Publication number | Publication date |
---|---|
WO2007026015A1 (fr) | 2007-03-08 |
RU2387660C2 (ru) | 2010-04-27 |
BRPI0616124A2 (pt) | 2011-06-07 |
RU2008112665A (ru) | 2009-10-10 |
US8377191B2 (en) | 2013-02-19 |
ZA200801622B (en) | 2009-06-24 |
CA2621020A1 (fr) | 2007-03-08 |
US20090053411A1 (en) | 2009-02-26 |
KR20080042920A (ko) | 2008-05-15 |
JP2009507100A (ja) | 2009-02-19 |
CN101305013A (zh) | 2008-11-12 |
JP5254791B2 (ja) | 2013-08-07 |
AU2006286513A1 (en) | 2007-03-08 |
EP1760084A1 (fr) | 2007-03-07 |
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