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WO2017191455A1 - Promoteurs d'adhésion - Google Patents

Promoteurs d'adhésion Download PDF

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Publication number
WO2017191455A1
WO2017191455A1 PCT/GB2017/051245 GB2017051245W WO2017191455A1 WO 2017191455 A1 WO2017191455 A1 WO 2017191455A1 GB 2017051245 W GB2017051245 W GB 2017051245W WO 2017191455 A1 WO2017191455 A1 WO 2017191455A1
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WO
WIPO (PCT)
Prior art keywords
compound
hydrogen
formula
alkyl
group
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.)
Ceased
Application number
PCT/GB2017/051245
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English (en)
Inventor
Paul Hugh Findlay
David Alan Pears
Lisa Elizabeth SCULLION
Magdalena Agnieszka Warunek
Robert Louis FINCH
Ryan James BANKS
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Itaconix UK Ltd
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Itaconix UK Ltd
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Publication of WO2017191455A1 publication Critical patent/WO2017191455A1/fr
Anticipated expiration legal-status Critical
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Classifications

    • 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
    • C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
    • C09J171/02—Polyalkylene oxides
    • 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
    • C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
    • C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
    • C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
    • 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

Definitions

  • the present invention relates to compounds that function as adhesion promoters.
  • the present invention also relates to processes for their preparation, to compositions and primer solutions comprising them, and to their use in the promotion of adhesion to a surface.
  • Adhesion promoters are used to improve the bonding strength between adhesives, sealants, coatings and inks to substrate surfaces where it is sometimes difficult to form a bond. This difficulty in forming a bond of sufficient strength between an adhesive, sealant, coating and/or ink composition and the surface of a substrate is often attributed to either the low surface energy of the substrate surface relative to that of the adhesive, sealant, coating and/or ink composition, or to the presence of a weak boundary layer or a degraded and/or polluted surface.
  • the substrate surface can of course vary greatly.
  • the substrate surface may be permeable, which may permit moisture and environmental chemicals to permeate to the interface between the adhesive, sealant, coating or ink composition and the substrate, thereby degrading the performance of the adhesive, sealant, coating or ink composition.
  • the porosity of the substrate surface can have an influence on the adhesion between, for example, an adhesive or sealant and the surface of the substrate, because porous surfaces often allow deep penetration of the adhesion promoter, potentially depleting the adhesion promoter at the target surface where bonding is required and thereby causing poor bonding.
  • the surface may be contaminated and/or oxidised, which may also impair the adhesion.
  • Adhesion promoters may be used as additives in adhesive or sealant formulations or, alternatively, as surface primers.
  • Primers and adhesion promoters work in a similar way to improve adhesion between two species. Both primers and adhesion promoters typically work by forming a new, usually organic, bifunctional layer, on the surface of the substrate. This new layer can then form bonds to, or interactions with, both the surface of the substrate and the adhesive/sealant matrix, thereby adhering the adhesive/sealant to the surface of the substrate.
  • the main difference between primers and adhesion promoters is that primers are applied to the substrate prior to the application of the adhesive or sealant, whereas adhesion promoters are added in situ with the adhesive or sealant.
  • adhesion promoters are included in the adhesive or sealant compositions and, once applied to a substrate surface, the adhesion promoter migrates to the substrate surface where it can form chemical bonds between the surface of the substrate and interact with polymer components within the adhesive or sealant.
  • adhesion promoters used in moisture curable hybrid formulations are organosilanes, such as aminosilanes.
  • moisture-curable sealant and adhesive products are made available to the professional and domestic markets. These products have many performance advantages over alternative sealants.
  • One class of such moisture-curable products are often referred to as hybrid sealants or modified silicone (MS) sealants. These products are typically moisture-curable systems containing silane-modified polyethers.
  • Commercial examples include MS polymers from Kaneka, or a silyl-modified polyurethane, such as Momentive's SPUR® 1015LM.
  • such formulations contain a silane terminated polyether in conjunction with an amino silane adhesion promoter.
  • hybrid adhesives and sealants offer inferior adhesion to a number of key substrates such as some plastics, stainless steel and concrete.
  • Ri , R 2 and R 3 are independently selected from hydrogen, (1 -4C)alkyl, hydroxy or (1 -4C)alkoxy;
  • R 4 and R 5 are independently selected from hydrogen or (1 -4C)alkyl; x is an integer selected from 0 to 6;
  • n is an integer selected from 1 or 2; L is a linker;
  • Q is a polyether comprising between 3 and 50 repeat units; and when n is 1 , W is selected from:
  • Wi, W 2 and W 3 are independently selected from NRi b , O or S(0) y i (wherein yi is 0, 1 or 2), and wherein Ri b is selected from hydrogen or (1 -4C)alkyl;
  • Rwi , Rw2, Rw3 and R W 4 are independently selected from hydrogen or (1 -4C)alkyl
  • c and d are independently integers from 1 to 4.
  • e is an integer from 0 to 2;
  • W is selected from N or a group of the formula:
  • W 4 and W 5 are independently selected from NRi c , O or S(0)y2 (wherein y 2 is 0, 1 or 2), and wherein Ri c is selected from hydrogen or (1 -4C)alkyl;
  • Rw5, Rw6, Rw7 and R w s are independently selected from hydrogen or (1 -4C)alkyl
  • f and g are independently integers from 1 to 4; and h is an integer from 0 to 2;
  • Ri, R 2 or R 3 is a (1 -4C)alkoxy or hydroxyl group.
  • composition comprising a compound as defined herein and optionally a moisture scavenger.
  • a sealant, adhesive, coating or ink composition comprising a compound as defined herein.
  • a primer solution comprising a compound as defined herein and a solvent.
  • a use of a compound, a composition or a primer solution as defined herein for promoting adhesion to a surface is provided.
  • W is as defined herein;
  • FGi is a functional group that when reacted with W-H links Q to W via linker group L, as defined herein;
  • Ri , R 2 , R3, R4, R5, x and Q are as defined herein.
  • alkyl includes both straight and branched chain alkyl groups. References to individual alkyl groups such as “propyl” are specific for the straight chain version only and references to individual branched chain alkyl groups such as “isopropyl” are specific for the branched chain version only.
  • (1 -6C)alkyl includes (1 -4C)alkyl, (1 -3C)alkyl, propyl, isopropyl and f-butyl.
  • phenyl(1 -6C)alkyl includes phenyl(1 -4C)alkyl, benzyl, 1 -phenylethyl and 2-phenylethyl.
  • phenyl(1 -6C)alkyl includes phenyl(1 -4C)alkyl, benzyl, 1 -phenylethyl and 2-phenylethyl.
  • (m-nC) or "(m-nC) group” used alone or as a prefix, refers to any group having m to n carbon atoms.
  • alkylene refers to an alky group that is positioned between and serves to connect two other chemical groups.
  • (1 -6C)alkylene means a linear saturated divalent hydrocarbon radical of one to six carbon atoms or a branched saturated divalent hydrocarbon radical of three to six carbon atoms, for example, methylene, ethylene, propylene, 2- methylpropylene, pentylene, and the like.
  • moisture curable used herein will be understood as referring to the process of curing or crosslinking (i.e. the toughening or hardening) of a chemical species, typically a polymer, through contact with water or moisture.
  • references to "polymeric components" of the adhesive and/or sealant compositions, as defined herein, will be understood as referring to any polymeric components present in such compositions (e.g. high molecular weight polyethers).
  • Ri , R 2 and R 3 are independently selected from hydrogen, (1 -4C)alkyl, hydroxy or (1 -4C)alkoxy;
  • R 4 and R 5 are independently selected from hydrogen or (1 -4C)alkyl; x is an integer selected from 0 to 6;
  • n is an integer selected from 1 or 2;
  • L is a linker
  • Q is a polyether comprising between 3 and 50 repeat units; and when n is 1 , W is selected from: (i) NRia, O or S(0) y (wherein y is 0, 1 or 2), wherein Ri a is selected from hydrogen or (1 -4C)alkyl; or
  • Wi, W 2 and W 3 are independently selected from NRi b , O or S(0) y i (wherein yi is 0, 1 or 2), and wherein Ri b is selected from hydrogen or (1 -4C)alkyl;
  • Rwi , Rw2, Rw3 and R W 4 are independently selected from hydrogen or (1 -4C)alkyl
  • c and d are independently selected from integers from 1 to 4.
  • e is an integer from 0 to 2;
  • W is selected from N or a group of the formula:
  • W 4 and W 5 are independently selected from NRi c , O or S(0)y2 (wherein y 2 is 0, 1 or 2), and wherein Ri c is selected from hydrogen or (1 -4C)alkyl;
  • Rw5, Rw6, Rw7 and R w s are independently selected from hydrogen or (1 -4C)alkyl
  • f and g are independently integers from 1 to 4; and h is an integer from 0 to 2;
  • Ri, R 2 or R 3 is a (1 -4C)alkoxy or hydroxyl group.
  • the compounds of the present invention function as adhesion promoters, thereby enhancing adhesion between a sealant, adhesive, coating and/or ink composition and the surface of a given substrate.
  • adhesion promoters due to their chemical composition and relatively low molecular weight, are miscible with, and thus may be readily incorporated into, a number of hybrid sealant, adhesive, coating and/or ink compositions using conventional mixing equipment.
  • This not only serves to make the adhesion promoters compatible with a large number of commercially available sealant, adhesive, coating and/or ink compositions, but it also significantly increases the number of bonding interactions between the adhesion promoter and: (i) the sealant, adhesive, coating and/or ink composition; and (ii) the substrate surface.
  • the compounds of the present invention also demonstrate a remarkable promotion of adhesion to surfaces that are typically considered a challenge to adhere to, such as, for example, PVC and stainless steel.
  • the compounds of the present invention can also be synthesised extremely easily.
  • the compounds can be synthesised by a facile one-step process, which is solvent-free from readily available reactants and does not require any additional purification steps.
  • An additional benefit of the compounds of the present invention is that they are significantly less hazardous to human health when compared to currently available organo silane adhesion promoters such as aminosilanes, epoxy silanes and isocyante-functional silane-based adhesion promoters.
  • the compounds of the present invention have an average molecular weight of between 250 and 3,000 Da.
  • the compounds of the present invention have an average molecular weight of between 300 and 2,200 Da.
  • the compounds of the present invention due to their molecular size and presence of a polyether moiety (Q), may also be referred to as polymers or oligomers depending on their molecular weight.
  • a polymer or an oligomer rarely consists of molecules having exactly the same degree of polymerisation, and hence the same molar mass (or molecular weight). More typically, there will be a distribution of molecular sizes and molecular weights for any given polymer.
  • the compounds of the present invention will have a dispersity (D), formerly known as polydispersity index) of less than 2, and more suitably less than 1 .5.
  • the dispersity will be understood by a person skilled in the art as referring to the ratio of the weight average molecular weight to the number average molecular weight of the compound of the present invention.
  • the compounds of the present invention are typically liquids.
  • the compounds of the present invention may have any suitable viscosity.
  • the compounds of the present invention will have a viscosity that is compatible with either application to a substrate surface (e.g. as a primer) and/or inclusion into a sealant, adhesive, coating and/or ink composition. It will be appreciated that viscosity of the compound of the present invention, or the compositions comprising them, may vary depending upon the surface that they are to be applied to.
  • the compounds or compositions of the present invention have a viscosity of between 10 and 10,000 mPa-S. In another embodiment, the compounds of the present invention have a viscosity of between 10 and 5,000 mPa-S. In another embodiment, the compounds of the present invention have a viscosity of between 10 and 1 ,000 mPa-S. In a further embodiment, the compounds of the present invention have a viscosity of between 50 and 500 mPa-S. In a particular embodiment, the viscosity is between 340 and 370 mPa-S.
  • the silane moiety (-SiRiR 2 R 3 ) and the heteroatoms of groups W, L and Q of the compounds of the present invention contributes to binding and/or interaction of the compound to a substrate surface.
  • at least one of the groups Ri, R 2 and R 3 is either a hydroxyl group or an alkoxy group that is susceptible to hydrolysis to form a hydroxyl group upon contact with moisture. These hydroxyl groups may react and crosslink with functional groups present on the substrate surface to covalently bind the adhesion promoter to the substrate surface.
  • Ri, R 2 and R 3 are independently selected from hydrogen, (1 - 4C)alkyl, hydroxy or (1 -4C)alkoxy. In an embodiment, Ri, R 2 and R 3 are independently selected from (1 -4C)alkyl, hydroxy or (1 -4C)alkoxy. In an embodiment, Ri, R 2 and R 3 are independently selected from (1 -4C)alkyl or (1 -4C)alkoxy. In an embodiment, Ri, R 2 and R 3 are independently selected from (1 -2C)alkyl or (1 -2C)alkoxy. In an embodiment, Ri, R 2 and R 3 are independently selected from methoxy or ethoxy. In an embodiment, Ri, R 2 and R 3 are all methoxy.
  • At least one of Ri, R 2 or R 3 is a (1 -4C)alkoxy group (e.g. methoxy). In yet another embodiment, at least two of Ri, R 2 or R 3 are (1 -4C)alkoxy groups (e.g. methoxy). In yet another embodiment, all of Ri, R 2 or R 3 are (1 -2C)alkoxy groups (e.g. methoxy).
  • the siliane (-SiRiR 2 R 3 ) group is attached to the compounds of the present invention via the -[C(R 4 )(R5)]x- group defined hereinabove.
  • R 4 and R 5 are independently selected from hydrogen or (1 -2C)alkyl. In yet another embodiment, R 4 and R 5 are both hydrogen.
  • x is an integer selected from 0 to 4. In yet another embodiment, x is an integer selected from 2 to 4. In yet another embodiment, x is 3.
  • n 1
  • n is 2.
  • W is selected from:
  • Ri a is selected from hydrogen or (1 -4C)alkyl
  • Wi, W 2 and W 3 are NRi b , wherein Ri b is selected from hydrogen or (1 -4C)alkyl; Rwi , w2, Rw3 and R W 4 are independently selected from hydrogen or (1 -4C)alkyl;
  • c and d are independently integers from 1 to 4.
  • e is an integer from 0 to 1 ;
  • W is selected from N or a group of the formula:
  • W 4 and W 5 are NRi c , wherein Ri c is selected from hydrogen or (1 -4C)alkyl;
  • Rw5, Rw6, Rw7 and R w s are independently selected from hydrogen or (1 -4C)alkyl
  • f and g are independently integers from 1 to 4; and h is an integer from 0 to 1 .
  • W is selected from:
  • Ri a is selected from hydrogen or methyl
  • Wi, W 2 and W 3 are NRi b , wherein Ri b is selected from hydrogen or (1 -4C)alkyl;
  • c and d are independently integers from 2 to 4.
  • e is an integer from 0 to 1 ;
  • W is selected from N or a group of the formula:
  • W 4 and W 5 are NRi c , wherein Ri c is selected from hydrogen or (1 -4C)alkyl;
  • f and g are independently integers from 2 to 4; and h is an integer from 0 to 1 .
  • W is selected from: (i) NRia, wherein Ri a is selected from hydrogen or methyl; or
  • Wi, W 2 and W 3 are NRi b , wherein Ri b is selected from hydrogen or (1 -4C)alkyl;
  • e is an integer from 0 to 1 ;
  • W is selected from N or a group of the formula:
  • W 4 and W 5 are NRi c , wherein Ri c is selected from hydrogen or (1 -4C)alkyl;
  • f and g are independently integers from 2 to 4; and h is an integer from 0 to 1.
  • W is N when n is 2, or W is selected from NRi a , O or S when n is 1.
  • W is N when n is 2, or W is NRi a when n is 1.
  • W is N and n is 2.
  • W is NRi a and n is 1.
  • Ri a is selected from hydrogen or (1 -2C)alkyl.
  • Ri a is selected from hydrogen or methyl. In another embodiment, Ri a is hydrogen. In another embodiment, Ri a is methyl.
  • L is a linker group, which may be a bond or any suitable linker capable of connecting Q to W.
  • the backbone moiety of L contains 2-10 atoms.
  • the term backbone moiety will be understood to refer those atoms disposed in the atomic chain linking W to Q, excluding the atoms of any branched groups.
  • the backbone moiety of L contains 2-6 atoms. More suitably, the backbone moiety of L contains 2-4 atoms. Most suitably, the backbone moiety of L contains 3 atoms.
  • the backbone atoms may have any of the definitions discussed herein in respect of L.
  • L is a group of formula A, shown below:
  • Y is:
  • p is an integer selected from 1 to 4.
  • A is selected from NR f , O or S(0) y (wherein y is 0, 1 or 2), wherein Rf is selected from hydrogen or (1 -4C)alkyl;
  • q is an integer selected from 1 to 4.
  • s is an integer selected from 0, 1 or 2;
  • Rb, Rc, Rd and R e are independently selected from hydrogen or (1 -4C)alkyl
  • Z is selected from C(O), C(0)0, C(0)NR g or S(0) y (wherein y is 0, 1 or 2), wherein R g is selected from hydrogen or (1 -4C)alkyl.
  • linkers of the invention include, for example, linkers of the formula A, wherein, unless otherwise stated, L, Y and Z each have any of the meanings defined hereinbefore or in any of paragraphs (1 ) to (9) hereinafter:
  • L is a group of the formula:
  • Y is:
  • p is an integer selected from 1 to 4.
  • q is an integer selected from 1 to 4.
  • s is an integer selected from 0, 1 or 2;
  • Rb, Rc, Rd and R e are independently selected from hydrogen or (1 -4C)alkyl;
  • A is NR f or O, wherein R f is selected from hydrogen or (1 - 4C)alkyl;
  • Z is selected from C(O), C(0)0 or C(0)NR g , wherein R g is selected from hydrogen or (1 -4C)alkyl;
  • L is a group of the formula:
  • Y is:
  • a (1 -6C)alkylene optionally substituted by one or more substituents selected from (1 -2C)alkyl or oxo;
  • p is an integer selected from 1 to 4.
  • q is an integer selected from 1 to 4.
  • s is an integer selected from 1 or 2;
  • Rb, Rc, Rd and R e are independently selected from hydrogen or methyl
  • A is NR f , wherein R f is selected from hydrogen or (1 - 2C)alkyl;
  • Z is selected from C(O), C(0)0 or C(0)NR g , wherein R g is selected from hydrogen or (1 -4C)alkyl;
  • L is a group of the formula:
  • Y is:
  • s is an integer selected from 1 or 2;
  • A is NRf, wherein Rf is selected from hydrogen or methyl
  • Z is selected from C(O), C(0)0 or C(0)NR g , wherein R g is selected from hydrogen or (1 -2C)alkyl;
  • L is a group of the formula:
  • Y is (1 -4C)alkylene or a group of the formula:
  • s is an integer selected from 1 or 2;
  • A is NRf, wherein Rf is selected from hydrogen or methyl
  • Z is selected from C(O), C(0)0 or C(0)NR g , wherein R g is selected from hydrogen or (1 -4C)alkyl;
  • L is a group of the formula:
  • Y is (1 -4C)alkylene or a group of the formula:
  • s is an integer selected from 1 or 2;
  • A is NRf, wherein Rf is selected from hydrogen or methyl
  • Z is selected from C(O), C(0)0 or C(0)NR g , wherein R g is selected from hydrogen or methyl;
  • L is a group of the formula:
  • Y is (1 -3C)alkylene or a group of the formula: -(CH 2 CH2)-[NH-(CH 2 CH2)]s- wherein:
  • s is an integer selected from 1 or 2;
  • Z is selected from C(O) , C(0)0 or C(0)NR g , wherein R g is selected from hydrogen or (1 -4C)alkyl;
  • L is selected from -(CH 2 CH2)-[NH-(CH 2 CH2)]s-C(0)- or a group of the formula:
  • s is an integer selected from 1 or 2;
  • R6 is selected from hydrogen or methyl
  • ⁇ denotes the point of attachment
  • L is selected from -(CH 2 CH 2 )-[NH-(CH 2 CH 2 )] s -C(0)- or a group of the formula:
  • s is an integer selected from 1 or 2;
  • L is a group of the formula:
  • L is as defined in any one of paragraphs (1 ) to (9) above. In another embodiment of the compounds of formula (I), L is as defined in any one of paragraphs (4) to (9) above. In an embodiment of the compounds of formula (I), L is as defined in paragraph (9) above.
  • Q is a polyether of between 2 and 50 repeat units.
  • polyether will be understood as referring to groups comprising two or more ether functional groups. Thus the term “polyether” will be understood to comprise diethers, triether, tetraethers, oligoether, polyethers and the like.
  • the term “repeat unit” will also be understood to mean a monomer of the polyether chain that is successively linked to one or more other repeat units so as to form the polyether. Thus, the repeat unit will be understood as referring to individual ether monomers.
  • the polyether component, Q, of the compounds of the present invention contributes towards the bonding (or interaction) of the compounds of the present invention with the sealant, adhesive, coating and/or ink composition.
  • the polarity of the polyether is believed to aid miscibility of this moiety of the compounds of the present invention with polymeric components having similar polarities (e.g. poly(ethylene glycol) and poly(propylene glycol)) present in the sealant, adhesive, coating and/or ink composition, thereby aiding bonding of the compound of the invention to the sealant, adhesive, coating and/or ink composition, and/or reducing the risk of phase separation.
  • hydrophobicity and so compatibility of the polyether may be varied through the specific selection of the ether repeat units that are used to form the polymer.
  • a poly(ethylene oxide) polyether may be used to obtain a compound of the present invention which is more hydrophilic in nature.
  • a poly(propylene oxide) based polyether may be used to obtain a compound of the present invention, which is more hydrophobic in nature.
  • poly(ethylene oxide) (PEO) is also commonly referred to as poly(ethylene glycol) (PEG) and polypropylene oxide) is known as polypropylene glycol) (PPG).
  • Q is a polyether selected from poly(ethylene oxide), polypropylene oxide), poly(butylene oxide), poly(tetramethylene oxide) or a co-polymer thereof.
  • Q is a polyether selected from poly(ethylene oxide), polypropylene oxide), polyputylene oxide) or a co-polymer thereof.
  • Q is a polyether selected from poly(ethylene oxide), polypropylene oxide) or a co-polymer thereof.
  • Q is a polyether selected from poly(ethylene oxide), polypropylene oxide) or a block co-polymer thereof.
  • Q is a polyether selected from poly(ethylene oxide) or polypropylene oxide).
  • co-polymer thereof refers to both random and block co-polymers.
  • poly(ethylene oxide), polypropylene oxide) and copolymers thereof will be understood to include poly(ethylene oxide), polypropylene oxide, random co-polymers comprising ethylene oxide and propylene oxide repeat units, and block copolymers comprising ethylene oxide and propylene oxide repeat units.
  • the polyether, Q has two termini, one of which is bound to L and the other of which is the terminus of the compound of the invention.
  • the terminus of the polyether connected to L comprises either a hydroxyl (OH) or amino (NH 2 ) group, most suitably a hydroxyl group. Accordingly, it will be understood by the person skilled in the art that once connected to L the oxygen or nitrogen atom of the hydroxyl or amino group respectively will form part of the linker L.
  • the other terminus of the polyether may comprise any suitable terminal group.
  • Any suitable terminal group may be present, but typically it will be a hydroxy or (1 -4C)alkoxy (e.g. methoxy) group or an ester or urethane.
  • the terminal group is selected from hydroxy and (1 -4C)alkoxy (e.g. methoxy). Most suitably, the terminal group is hydroxy.
  • polyether refers to a group consisting of the repeating monomeric units discussed herein (of which there may be one or more type), wherein the end-most repeating monomeric unit (i.e. the repeating monomeric unit most distant from L) is terminated in a terminal group discussed herein.
  • the terminal group is selected from hydroxy and (1 -4C)alkoxy (e.g. methoxy). Most suitably, the terminal group is hydroxy.
  • Polyethers that comprise an amino group at the terminal end of the polyether to be connected to the linker, L are commonly referred to as polyetheramines, and are commercially available from Huntsman under the trade name JeffamineTM.
  • polyetheramines are supplied as block co-polymers of ethylene and propylene oxide and thus will be understood as being encompassed by the term "poly(ethylene oxide), poly(propylene oxide) and co-polymers thereof".
  • R p is selected from H or methyl
  • a and b are integers.
  • Q is a polyether comprising between 3 and 50 repeat units. In another embodiment of the present invention, Q is a polyether comprising between 3 and 40 repeat units. In another embodiment of the present invention, Q is a polyether comprising between 3 and 20 repeat units. In another embodiment of the present invention, Q is a polyether comprising between 4 and 10 repeat units.
  • Q is of the formula shown below:
  • X is a NH or O
  • R p is selected from H or methyl
  • R 8 is selected from hydrogen or (1 -4C)alkyl
  • a and b are integers
  • ⁇ denotes the point of attachment to L.
  • the sum of integers a and b is an integer 3 to 50. More suitably, the sum of integers a and b is an integer 3 to 40. More suitably, the sum of integers a and b is an integer 3 to 20. Most suitably, the sum of integers a and b is an integer 4 to 10.
  • Q is a polyether of the formula shown below:
  • R7 is selected from hydrogen or methyl
  • R 8 is selected from hydrogen or (1 -4C)alkyl
  • n integer between 4 and 10; and denotes the point of attachment to L.
  • Ri, R2 and R 3 are independently selected from (1 -4C)alkyl, hydroxy or 4C)alkoxy;
  • R 4 and R 5 are independently selected from hydrogen or (1 -4C)alkyl; x is an integer selected from 0 to 4;
  • n is an integer selected from 1 or 2;
  • W is selected from:
  • Ri a is selected from hydrogen or (1 -4C)alkyl
  • Wi, W 2 and W 3 are NRi b , wherein Ri b is selected from hydrogen or (1 -4C)alkyl;
  • Rwi , Rw2, Rw3 and R W 4 are independently selected from hydrogen or (1 -4C)alkyl
  • c and d are independently integers from 1 to 4.
  • e is an integer from 0 to 1 ;
  • W is selected from N or a group of the formula:
  • W 4 and W 5 are NRi c , wherein Ri c is selected from hydrogen or (1 -4C)alkyl;
  • W 6 is N;
  • Rw5, w6, Rw7 and R w s are independently selected from hydrogen or (1 -4C)alkyl;
  • f and g are independently integers from 1 to 4; and h is an integer from 0 to 1 .;
  • Y is absent, a (1 -6C)alkylene optionally substituted by one or more substituents selected from (1 -2C)alkyl, or a group of the formula:
  • p is an integer selected from 1 to 3;
  • q is an integer selected from 1 to 3;
  • s is an integer selected from 0, 1 or 2;
  • Rb, Rc, Rd and R e are independently selected from hydrogen or methyl
  • A is NRf, wherein Rf is selected from hydrogen or (1 -2C)alkyl; and Z is selected from C(O), C(0)0 or C(0)NR g , wherein R g is selected from hydrogen or (1 -4C)alkyl; and
  • Q is a polyether comprising between 3 and 50 repeat units; with the proviso that at least one of Ri , R 2 or R 3 is a hydroxyl or (1 -4C)alkoxy;
  • R 2 and R 3 are independently selected from (1 -4C)alkyl, hydroxy or (1 - 4C)alkoxy;
  • R 4 and R 5 are independently selected from hydrogen or methyl
  • x is an integer selected from 0 to 4.
  • n is an integer selected from 1 or 2;
  • W is N when n is 2, or W is NRi a when n is 1 ; wherein Ri a is selected from hydrogen or (1 -4C)alkyl; Y is absent, a (1 -6C)alkylene optionally substituted by one or more substituents selected from (1 -2C)alkyl, or a group of the formula:
  • s is an integer selected from 1 or 2;
  • A is NRf, wherein Rf is selected from hydrogen or (1 -2C)alkyl; and Z is selected from C(O), C(0)0 or C(0)NR g , wherein R g is selected from hydrogen or (1 -4C)alkyl; and
  • Q is a polyether comprising between 3 and 50 repeat units;
  • R 2 and R 3 are independently selected from (1 -4C)alkyl, hydroxy or (1 - 4C)alkoxy;
  • x is an integer selected from 2 to 4.
  • n is an integer selected from 1 or 2;
  • W is N when n is 2, or W is NRi a when n is 1 ; wherein Ri a is selected from hydrogen or methyl;
  • Y is (1 -6C)alkylene or a group of the formula:
  • s is an integer selected from 1 or 2;
  • A is NRf, wherein Rf is selected from hydrogen or (1 -2C)alkyl; and Z is selected from C(O), C(0)0 or C(0)NR g , wherein R g is selected from hydrogen or (1 -4C)alkyl; and
  • Q is a polyether comprising between 3 and 50 repeat units;
  • R 2 and R 3 are independently selected from (1 -4C)alkyl, hydroxy or (1 - 4C)alkoxy;
  • n is an integer selected from 1 or 2;
  • W is N when n is 2, or W is NRi a when n is 1 ; wherein Ri a is selected from hydrogen or methyl;
  • Y is (1 -3C)alkylene or a group of the formula:
  • s is an integer selected from 1 or 2;
  • A is NRf, wherein Rf is selected from hydrogen or (1 -2C)alkyl; and Z is absent or selected from C(O) or C(0)NR g , wherein R g is selected from hydrogen or methyl; and
  • Q is a polyether comprising between 3 and 50 repeat units;
  • R 2 and R 3 are independently selected from (1 -4C)alkyl, hydroxy or (1 - 4C)alkoxy;
  • R 4 and R 5 are independently selected from hydrogen or (1 -4C)alkyl; x is an integer selected from 0 to 4;
  • n is an integer selected from 1 or 2;
  • W is N when n is 2, or W is NH when n is 1 ;
  • R 6 is selected from hydrogen or methyl; and Q is a polyether comprising between 3 and 50 repeat units, selected from poly(ethylene oxide), polypropylene oxide), poly(butylene oxide), poly(tetramethylene oxide) or a co-polymer thereof;
  • R 2 and R 3 are independently selected from (1 -4C)alkyl, hydroxy or (1 - 4C)alkoxy;
  • x is an integer selected from 2 to 4.
  • n is an integer selected from 1 or 2;
  • W is N when n is 2, or W is NH when n is 1 ;
  • R 6 is selected from hydrogen or methyl
  • Q is a polyether comprising between 4 and 10 repeat units, selected from poly(ethylene oxide), polypropylene oxide) or a co-polymer thereof;
  • R 2 and R 3 are independently selected from (1 -4C)alkyl, hydroxy or (1 -4C)alkoxy; R7 is selected from hydrogen or methyl;
  • W is N when n is 2, or W is NH when n is 1 ;
  • n is an integer selected from 1 or 2;
  • y is an integer selected from 4 to 10;
  • Particular compounds of the invention include any one of the following:
  • y is selected from 2 to 50, 3 to 50, 3 to 40, 3 to 20, or 4 to 10.
  • Suitable salt forms of the present invention include, but are not limited to, acid addition salts or base salts.
  • the compounds of the present invention can be prepared by any suitable technique known in the art. Particular processes for the preparation of these compounds are described further in the accompanying examples. [0072] In the description of the synthetic methods described herein and in any referenced synthetic methods that are used to prepare the starting materials, it is to be understood that all proposed reaction conditions, including choice of solvent, reaction atmosphere, reaction temperature, duration of the experiment and workup procedures, can be selected by a person skilled in the art.
  • the compounds of formula (I) may be synthesised by a process comprising reacting a compound of formula (III) with a compound with formula (IV):
  • W is as defined herein;
  • FGi is a functional group that when reacted with W-H links Q to W via linker group L, as defined herein;
  • the compounds of formula (I) may be synthesised by a process comprising reacting an aminosilane with a polyether acrylate or polyether methacrylate.
  • the silane-terminated polyethers can be prepared by reacting an acrylate- or methacrylate-functional polyether with an amine-functional silane.
  • the (meth)acrylate functionality of the functional polyether readily reacts with the primary amine functionality of the aminosilane via a Michael addition process. When the reaction is between a primary amine and an acrylate, this process takes place at ambient temperatures, does not form any byproducts and does not require any additional catalyst.
  • the polyether (meth)acrylate may be selected from poly(propylene oxide) acrylate, polypropylene oxide) methacrylate, poly(ethylene oxide) acrylate, poly(ethylene oxide) methacrylate, poly(tetrahydrofuran) acrylate and poly(tetrahydrofan) methacrylate. Block or random copolymers of these units can also be used. Due to the increased reactivity, it is preferred that acrylate-functional polyethers are utilised. It is also preferable if the mono- functional polyether is used in the reaction.
  • Suitable polyether methacrylate are polyether methacrylates of the formula:
  • a+b is between 3 and 50, most preferably between 4 and 20.
  • This polymer (above) is commercially available from Clariant under the trade names Polyglykol MA 350 and Polyglykol MA 750.
  • a particular polyether acrylate is polypropylene oxide) acrylate
  • y is between 3 and 50, most preferably between 4 and 10.
  • poly(ethylene oxide) acrylate is poly(ethylene oxide) acrylate:
  • y is between 3 and 50, most preferably between 4 and 10.
  • the aminosilane is selected from to 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropylmethyldiethoxysilane, N-(2-aminoethyl)-3- aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, N-(2-aminoethyl)- 3-aminopropylmethyldimethoxysilane N-(3-Trimethoxysilylpropyl)diethylenetriamine or N-(3- Triethoxysilylpropyl)diethylenetriamine and N-(3-methyldimethoxysilylpropyl)diethylenetriamine.
  • the process for the preparation of a compound of formula (I) is solvent free.
  • the process for the preparation of a compound of formula (I) is catalyst free.
  • the process for the preparation of a compound of formula (I) is conducted at a temperature of between 0 and l OCO.
  • the process for the preparation of a compound of formula (I) is conducted at a temperature of between 0 and 75 °C. More suitably, the process for the preparation of a compound of formula (I) is conducted at a temperature of between 10 and 60 °C.
  • reaction between the compounds of formula (III) and (IV) is a Michael addition reaction.
  • FGi is an acrylate or a methacrylate.
  • compositions of the invention are provided.
  • the compound is mixed with a moisture scavenger and could be stored and/or supplied to consumers in this form.
  • the present invention provides a composition comprising, or consisting essentially of, or consisting of, a compound, as defined herein, and a moisture scavenger.
  • the moisture scavenger is an alkoxysilane or oxazolidine-based moisture scavengers (e.g. Incozol 2 supplied by Incorez).
  • the moisture scavenger is selected from vinyltrimethoxysilane, vinyltriethoxysilane or Incozol 2.
  • the moisture scavenger is vinyltrimethoxysilane or vinyltriethoxysilane.
  • the compound and moisture scavenger composition of the present invention may also comprise any suitable amount of moisture scavenger.
  • the compositions of the present invention comprises between 0.1 and 10% w/w of moisture scavenger. More suitably, the compositions of the present invention comprises between 0.1 and 5% w/w of moisture scavenger. Yet more suitably, the compositions of the present invention comprises between 0.1 and 3% w/w of moisture scavenger. Most suitably, the compositions of the present invention comprises between 0.1 and 1 % w/w of moisture scavenger.
  • the compound and moisture scavenger composition comprises between 0.1 and 99% w/w of a compound, as defined herein.
  • the compound and moisture scavenger composition comprises between 0.1 and 95% w/w of a compound, as defined herein. More suitably, the compound and moisture scavenger composition comprises between 0.1 and 90% w/w of a compound, as defined herein. Yet more suitably, the compound and moisture scavenger composition comprises between 0.1 and 75% w/w of a compound, as defined herein. Most suitably, the compound and moisture scavenger composition comprises between 0.1 and 50% w/w of a compound, as defined herein.
  • a sealant, adhesive, coating or ink composition comprising a compound, as defined herein, and a moisture scavenger.
  • a sealant or adhesive composition comprising a compound, as defined herein, and a moisture scavenger.
  • a sealant composition comprising a compound, as defined herein, and a moisture scavenger.
  • a moisture-curable sealant composition comprising a compound, as defined herein, and a moisture scavenger.
  • the moisture scavenger is an alkoxysilane or oxazolidine-based moisture scavengers (e.g. Incozol 2 supplied by Incorez).
  • the moisture scavenger is selected from vinyltrimethoxysilane, vinyltriethoxysilane or Incozol 2.
  • the moisture scavenger is vinyltrimethoxysilane or vinyltriethoxysilane.
  • the compositions of the present invention may comprise any suitable amount of compound of formula (I).
  • the compositions of the present invention comprises between 0.1 and 75% w/w of a compound of formula (I).
  • compositions of the present invention comprises between 0.1 and 50% w/w of a compound of formula (I). Yet more suitably, the compositions of the present invention comprises between 0.1 and 20% w/w of a compound of formula (I). Most suitably, the compositions of the present invention comprises between 0.1 and 10% w/w of a compound of formula (I).
  • the sealant, adhesive, coating and/or ink composition compositions of the present invention may also comprise any suitable amount of moisture scavenger.
  • the compositions of the present invention comprises between 0.1 and 10% w/w of moisture scavenger. More suitably, the compositions of the present invention comprises between 0.1 and 5% w/w of moisture scavenger. Yet more suitably, the compositions of the present invention comprises between 0.1 and 3% w/w of moisture scavenger. Most suitably, the compositions of the present invention comprises between 0.1 and 1 % w/w of moisture scavenger.
  • compositions of the present invention comprises a solvent.
  • the composition comprises an organic solvent.
  • compositions of the present invention may comprise additional formulation components.
  • Additional formulation components may be included to improve various properties of the formulation, such as, for example, viscosity, open time, modulus, mechanical resistance, UV resistance, formulation stability and ease of application.
  • a person skilled in the art will be able to select suitable formulation components to include based on conventional knowledge in the formulation field.
  • a non-limiting list of possible additional formulation components that may be added to the compositions of the present invention include: pH modifiers, surfactants and solubility enhancers such as dispersants and emulsifiers, viscosity modifiers, wetting agents, preservatives, lubricants, fillers, film formers and resins, extenders, sizing agents, antifouling agents, barriers to moisture and gas, catalysts, curing and drying agents, antifoam and defoaming agents, plasticisers, UV-stabilisers, and colorants including pigments and dyes
  • compositions may also comprise one or more additional adhesion promoters.
  • sealant and/or adhesive composition defined hereinabove may comprise any suitable sealant and/or adhesive formulation commercially available or known in the art, or may comprise a model sealant and/or adhesive composition comprising the ingredients listed in the table below: Component % w/w
  • Thixotropic Agent e.g. S1O2
  • S1O2 Thixotropic Agent
  • Catalyst e.g. dibutyltin dilaurate 0.01 -1
  • a primer solution comprising a compound, as defined herein, and a solvent.
  • the primer solution may comprise any suitable amount of compound, which may vary according to the intended use and storage of the primer solution.
  • the primer solution comprises between 0.5 and 90% w/w of a compound of formula (I).
  • the primer solution comprises between 0.5 and 75% w/w of a compound of formula (I).
  • the primer solution comprises between 0.5 and 50% w/w of a compound of formula (I).
  • the primer solution comprises between 0.5 and 25% w/w of a compound of formula (I).
  • the primer solution comprises a moisture scavenger.
  • the moisture scavenger is an alkoxysilane or oxazolidine-based moisture scavengers (e.g. Incozol 2 supplied by Incorez). More suitably, the moisture scavenger is selected from vinyltrimethoxysilane, vinyltriethoxysilane or Incozol 2. Most suitably, the moisture scavenger is vinyltrimethoxysilane or vinyltriethoxysilane.
  • the primer solution comprises between 0.1 and 10% w/w of moisture scavenger.
  • the compositions of the present invention comprises between 0.1 and 5% w/w of moisture scavenger. More suitably, the compositions of the present invention comprises between 0.1 and 3% w/w of moisture scavenger. Most suitably, the compositions of the present invention comprises between 0.1 and 1 % w/w of moisture scavenger.
  • the solvent is an organic solvent.
  • the solvent is a non-reactive organic solvent. More suitably, the solvent is a non- reactive organic solvent the selected from n-butyl acetate, methylethyl ketone, acetone, toluene, xylene, ethyl benzene, naptha, mineral spirits, oxides such as propylene oxide, tetrahydrofuran and turpentine.
  • the primer solutions of the present invention may comprise additional adjuncts. Additional adjuncts may be included to improve various properties of the formulation, such as, for example, formulation stability and administrability. A person skilled in the art will be able to select suitable adjuncts to include based on conventional knowledge in the formulation field.
  • a non-limiting list of possible additional adjuncts that may be added to the primer solutions of the present invention include: pH modifiers, surfactants, viscosity modifiers, preservatives, lubricants and solubility enhancers.
  • the primer solutions may also comprise one or more additional adhesion promoters.
  • the present invention provides compounds, compositions and primer solutions that function as adhesion promoters.
  • the present invention therefore provides a method for promoting adhesion to a surface, said method comprising contacting a surface with a compound, a composition or a primer solution, as defined herein.
  • the present invention further provides a method for promoting adhesion of a sealant, adhesive, coating or ink to a surface, said method comprising contacting a surface with a compound, a composition or a primer solution, as defined herein.
  • the present invention provides a method for promoting adhesion of a sealant or adhesive to a surface, said method comprising contacting a surface with a compound, a composition or a primer solution, as defined herein.
  • the present invention provides a method for promoting adhesion of a sealant, adhesive, coating or ink to a surface, wherein the surface is selected from glass, plastic [e.g.
  • poly(ethylene terephthalate) PET
  • PVC polypropylene or polystyrene
  • rubber e.g. natural rubber, styrene-butadiene-styrene (SBS) rubber, polyisoprene, polybutadiene, polycarbonates, melamine-formaldehyde resins, polyurea or polyurethane resins
  • concrete leather, paper, card, plaster, plasterboard, wood, chipboard, fabric (e.g. cotton, canvas, nylon, polyesters or high performance fabrics such as Kevlar®) or a metal (e.g. as steel, stainless steel, copper, aluminium or copper alloys such as brass or bronze).
  • the surface is selected from plastic, rubber, concrete or a metal. More suitably, the surface is selected from stainless steel, concrete, plastic or rubber. Most suitably, the surface is selected from stainless steel, concrete, polyvinyl chloride) (PVC) or ethylene propylene diene monomer (EPDM) rubber.
  • PVC polyvinyl chloride
  • EPDM ethylene propylene diene monomer
  • the present invention also provides a compound, a composition or a primer solution, as defined herein, for use in promoting adhesion to a surface.
  • the present invention further provides a compound, a composition or a primer solution, as defined herein, for use in promoting adhesion of a sealant, adhesive, coating or ink to a surface.
  • the present invention provides a compound, a composition or a primer solution, as defined herein, for use in promoting adhesion of a sealant, adhesive, coating or ink to a surface, wherein the surface is selected from glass, plastic, rubber, concrete, leather, paper, card, wood or a metal.
  • the surface is selected from plastic, rubber, concrete or a metal. More suitably, the surface is selected from stainless steel, concrete, plastic or rubber. Most suitably, the surface is selected from stainless steel, concrete, polyvinyl chloride) (PVC) or ethylene propylene diene monomer (EPDM) rubber.
  • Onichem A31 1 3-aminopropymethyldimethoxysilane - Onichem Polypropylene oxide) acrylate, Mn -475 Da Sigma Aldrich Silquest A-171 - vinyltrimethoxysilane Momentive
  • Bisomer PPA6 polypropylene oxide) acrylate is also known as polypropyleneglycol (6) acrylate.
  • Bisomer PEA6 poly(ethylene oxide) acrylate is also known as polyethyleneglycol (6) acrylate.
  • dimethoxysilane (21 0.0 g, 0.5 aminopropymethyl 25 °C, 2 moles) dimethoxysilane (5.83 g, ) hours
  • Model formulations were typically prepared by making a premix in two steps. In the first step, the prepolymer and the plasticizer ware mixed together. In the second step the premix was mixed with a moisture scavenger, the silica and the catalyst. The premix was then put into a Plastigraph Brabender mixer (Nr 174510, model 824300, head 60/30cc with roller blades) where calcium carbonate and titanium oxide were added. The sealant was then mixed for 10-15 minutes at room temperature at 40 rpm then the adhesion promoter was added under nitrogen and mixed for further 5 minutes under inert conditions.
  • Dry concrete blocks with dimensions 100mm x 100mm x 50mm.
  • the surface was brushed with a metal brush to expose the grains.
  • the sealant composition was then applied on top of the surface to create a strip that was at least 3 mm thick, 10 mm wide and 150 mm long.
  • the samples were then cured for 7 days at 25 °C and 60 % relative humidity and a hand peel adhesion test (see below) is performed. Following this, the samples were cured for further 7 days - to make a 2 week curing cycle and the hand peel adhesion test was repeated.
  • the blocks were cleaned and immersed in water for 48 hours prior to use, the blocks were then removed from the water and padded dry with tissue paper. The sealant was then applied and assessed as for the dry concrete blocks.
  • the Arbo EPDM membrane is cut into 200 x 20mm with the thickness of the EPDM already being set at 0.75mm, for ease of application the strips are attached to a hard surface. The surface was wiped clean with methylated spirits and tissue, and then the sealant composition was then applied and assessed as for the dry concrete blocks.
  • the peel adhesion test is the most effective test to verify sealant adhesion to a substrate surface.
  • the procedure for the peel adhesion test was undertaken in the following steps:
  • the substrate was wiped cleaned with methylated spirits and tissue.
  • PE300/PE-HWST high density poly(ethylene) HDPE 2 mm sheet.
  • the sealant composition was then placed inside the internal cavity of the PTFE cast and scraped to be level with the upper rim of the cast and left to cure in a humidity cabinet at 25 °C for 60% RH and tested after 7 and 14 days.
  • testometric micro 350 settings were as follows:

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
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  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polyethers (AREA)

Abstract

La présente invention concerne des composés de formule (I) qui fonctionnent en tant que promoteurs d'adhésion : dans laquelle R1, R2, R3, R4, R5, W, L, Q, x et n sont chacun tels que définis dans la description. La présente invention concerne également des procédés de préparation de ces composés, des compositions et des solutions d'amorce les contenant, et leur utilisation dans la promotion de l'adhésion à une surface.
PCT/GB2017/051245 2016-05-05 2017-05-04 Promoteurs d'adhésion Ceased WO2017191455A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB1607902.2 2016-05-05
GBGB1607902.2A GB201607902D0 (en) 2016-05-05 2016-05-05 Adhesion promoters

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114249886A (zh) * 2021-12-31 2022-03-29 三棵树(上海)新材料研究有限公司 耐老化改性硅烷封端聚醚树脂、ms免钉胶及其制备方法
CN116178704A (zh) * 2023-04-04 2023-05-30 山东宇龙高分子科技有限公司 一种新型异氰酸酯基硅烷改性聚醚聚合物的制备方法

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Publication number Priority date Publication date Assignee Title
WO1998031720A1 (fr) * 1997-01-17 1998-07-23 Dow Corning Corporation Revetements d'isolement a base de silicone/acrylate polyvalent
WO2000047588A1 (fr) * 1999-02-09 2000-08-17 Cognis Deutschland Gmbh Esters d'aminosilane
WO2007061846A2 (fr) * 2005-11-22 2007-05-31 Henkel Corporation Polymeres silyles durcissant a l'humidite pour compositions de durcissement rapide a l'humidite
WO2009129649A1 (fr) * 2008-04-22 2009-10-29 Industrial Technology Research Institute Polymere biocompatible et nanoparticule magnetique a biocompatibilite

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998031720A1 (fr) * 1997-01-17 1998-07-23 Dow Corning Corporation Revetements d'isolement a base de silicone/acrylate polyvalent
WO2000047588A1 (fr) * 1999-02-09 2000-08-17 Cognis Deutschland Gmbh Esters d'aminosilane
WO2007061846A2 (fr) * 2005-11-22 2007-05-31 Henkel Corporation Polymeres silyles durcissant a l'humidite pour compositions de durcissement rapide a l'humidite
WO2009129649A1 (fr) * 2008-04-22 2009-10-29 Industrial Technology Research Institute Polymere biocompatible et nanoparticule magnetique a biocompatibilite

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114249886A (zh) * 2021-12-31 2022-03-29 三棵树(上海)新材料研究有限公司 耐老化改性硅烷封端聚醚树脂、ms免钉胶及其制备方法
CN114249886B (zh) * 2021-12-31 2023-10-31 三棵树(上海)新材料研究有限公司 耐老化改性硅烷封端聚醚树脂、ms免钉胶及其制备方法
CN116178704A (zh) * 2023-04-04 2023-05-30 山东宇龙高分子科技有限公司 一种新型异氰酸酯基硅烷改性聚醚聚合物的制备方法

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