WO2004037941A2 - Continuous process for producing hot melt adhesive compositions - Google Patents
Continuous process for producing hot melt adhesive compositions Download PDFInfo
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- WO2004037941A2 WO2004037941A2 PCT/US2003/025951 US0325951W WO2004037941A2 WO 2004037941 A2 WO2004037941 A2 WO 2004037941A2 US 0325951 W US0325951 W US 0325951W WO 2004037941 A2 WO2004037941 A2 WO 2004037941A2
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- hot melt
- melt adhesive
- adhesive composition
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- mixture
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
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- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/14—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/28—Non-macromolecular organic substances
- C08L2666/44—Silicon-containing compounds
Definitions
- This invention pertains to a continuous method for producing moisture curable hot melt adhesive compositions.
- the method comprises feeding a mixture of an organopolysiloxane, silicone resin, silane crosslinker and solvent into an extruder and removing the volatiles.
- a continuous process it is possible to control the nonvolatile content and produce a consistent product.
- the hot melt adhesive composition cures resulting in adhesion between at least two substrates.
- Moisture curable organosiloxane compositions find use in various applications, for example as sealant compositions that can be applied to a joint between elements and cured to provide an elastomeric seal between them. These compositions cure at room temperature and are particularly attractive for use as sealant compositions for sealing, for example highway joints, joints in articles such as vehicle headlights and joints in buildings and in glazing applications, because no special heating or other cure conditions are generally required to produce a seal of desired quality.
- moisture curable organosiloxane compositions have been proposed and are generally formed from an at least one substantially linear polyorganosiloxane containing at least two silanol groups, a crosslinker capable of reaction with the polyorganosiloxane to yield a crosslinked network, and catalyst materials. These compositions cure by a condensation reaction promoted by moisture.
- the crosslinker in moisture curable organosiloxane compositions is generally selected from polyfunctional silanes that readily hydrolyze. Commonly employed crosslinkers are triacetoxy silanes, trialkoxy silanes, triamino silanes and trioximo silanes.
- condensation reaction proceeds via a capping of the polyorganosiloxane with, for example, dialkoxyalkylsilyl groups followed by interaction of the alkoxy groups of the end caps and or silanol groups to yield a crosslinked structure.
- Moisture curable compositions based on organosilicon compounds generally contain finely divided fillers. The fillers generally used are those that strengthen the cured material, reduce the cost of the product or otherwise confer a desired combination of properties.
- Typical fillers include but are not limited to high surface area silicas, ground quartz, iron oxide, zinc oxide, carbon black, calcium carbonate and diatomaceous earth.
- Moisture curable organosiloxane compositions can be manufactured using a batch or continuous process during which the filler and polyorganosiloxane are mixed together, the crosslinker and catalyst are added to the mixture and the resultant composition is then packaged in containers such as cartridges, which are then sealed in an airtight manner to prevent ingress of moisture.
- Silicone pressure-sensitive adhesives typically contain at least two primary components, namely a linear siloxane polymer and a tackifier resin consisting essentially of triorganosiloxane units (i.e., R 3 SiOi /2 units, in which R denotes a monovalent organic group) and silicate units (i.e.
- these PSA compositions are typically dispersed in an organic solvent for ease of application. Some of these PSAs contain reactive groups, which allow the compositions to be cured by exposure to moisture. When the proportions of the above described resin and polymer and other parameters are adjusted similar combinations can be formulated into coating compositions. Under certain other conditions, hot melt PSAs can be obtained.
- This invention pertains to continuous process for producing a moisture curable hot melt silicone pressure sensitive adhesive composition.
- the process comprises combining an organopolysiloxane, silicone resin, silane crosslinker and solvent; feeding the combination through an extrusion device to remove volatiles; and recovering a hot melt adhesive composition having a non- volatile content of 95 wt% or more.
- the use of the continuous process allows for more efficient production of the hot melt adhesive composition and the production of a more consistent product. This method of processing is advantageous from the standpoints of cost, convenience and product consistency.
- This invention pertains to a continuous process for producing hot melt adhesive compositions.
- the process comprises combining an organopolysiloxane, silicone resin, silane crosslinker and solvent; feeding the combination through an extrusion device to remove volatiles; and recovering a hot melt adhesive composition having a non- volatile content of 95 wt% or more.
- the silicone resin useful herein contains monofunctional units represented by R 1 3 SiO ⁇ /2 and tetrafunctional units represented by SiO 4/2 .
- R 1 represents a substituted or unsubstituted monovalent hydrocarbon radical.
- Silicone resins of this type are well known in the art as one of the ingredients present in organosiloxane compositions used as pressure sensitive adhesives.
- the silicone resin is soluble in liquid hydrocarbons such as benzene, toluene, xylene, heptane and the like or in liquid organosilicon compounds such as a low viscosity cyclic and linear polydiorganosiloxanes.
- R 1 is typically a monovalent hydrocarbon radical containing up to 20 carbon atoms, typically from 1 to 10 carbon atoms.
- suitable hydrocarbon radicals for R 1 include alkyl radicals, such as methyl, ethyl, propyl, pentyl, octyl, undecyl and octadecyl; alkenyl radicals, such as vinyl, allyl and 5-hexenyl; cycloaliphatic radicals, such as cyclohexyl and cyclohexenylethyl; and aryl radicals such as phenyl, tolyl, xylyl, benzyl and 2-phenylethyl.
- Non-reactive substituents that can be present on R 1 include but are not limited to halogen and cyano.
- Typical substituted hydrocarbon radicals that can be represented by R include but are not limited to chloromethyl and 3,3,3-trifluoropropyl.
- At least one-third, alternatively at least two-thirds of the R 1 radicals in the unit are methyl radicals.
- R ⁇ SiO ⁇ units include but are not limited to Me 3 SiO ⁇ . /2 , PhMe 2 SiO 1/2 and Me 2 NiSi ⁇ !/2 where Me, Ph and Vi denote methyl, phenyl and vinyl, respectively.
- the silicone resin may contain two or more of these units.
- the molar ratio of the R 3 SiO ⁇ /2 and SiO 4/2 units in the silicone resin is typically from 0.5/1 to 1.5/1, preferably from 0.6/1 to 0.9/1.
- the R ⁇ SiO ⁇ to SiO 4/2 ratio can be expressed as ⁇ M(resin)+M(rieopentamer) ⁇ / ⁇ Q(resin)+Q(neopentamer) ⁇ and represents the ratio of the total number of triorganosiloxy groups of the resinous and neopentamer portions of the silicone resin to the total number of silicate groups in the resinous and neopentamer portions.
- the silicone resin contains 2.0 wt% or less, alternatively 0.7 wt% or less, alternatively 0.3 wt% or less, of terminal units represented by the formula XSiO 3/2 , where X represents hydroxyl or a hydrolyzable group such as alkoxy such as methoxy and ethoxy; alkenyloxy such as isopropenyloxy; ketoximo such as methyethylketoximo; carboxy such as acetoxy; amidoxy such as acetamidoxy; and aminoxy such as ⁇ , ⁇ -dimethylaminoxy.
- the concentration of silanol groups present in the silicone resin can be determined using Fourier transform infrared spectrophotometry (FTJtR).
- the number average molecular weight, M n required to achieve the desired flow characteristics of the silicone resin will depend at least in part on the molecular weight of the silicone resin and the type(s) of hydrocarbon radicals, represented by R 1 , that are present in this ingredient.
- M n as used herein represents the molecular weight measured using gel permeation chromatography, when the peak representing the neopentamer is excluded form the measurement.
- the M n of the silicone resin is typically greater than 3,000, more typically from 4500 to 7500.
- the thermal hold i.e. the ability of an adhesive to retain its adhesion at elevated temperatures
- the silicone resin can be prepared by any suitable method. Silicone resins of this type have reportedly been prepared by cohydrolysis of the corresponding silanes or by silica hydrosol capping methods known in the art.
- the silicone resin is preferably prepared by the silica hydrosol capping processes of Daudt, et al., U.S. Pat. No. 2,676,182; of Rivers-Farrell et al., U.S. Pat. No. 4,611,042; and of Butler, U.S. Pat. No. 4,774,310.
- the intermediates used to prepare the silicone resin are typically triorganosilanes of the formula R ⁇ SiX', where X' represents a hydrolyzable group, and either a silane with four hydrolyzable groups such as halogen, alkoxy or hydroxyl, or an alkali metal silicate such as sodium silicate.
- X' represents a hydrolyzable group
- a silane with four hydrolyzable groups such as halogen, alkoxy or hydroxyl, or an alkali metal silicate such as sodium silicate.
- the silicon-bonded hydroxyl groups (i.e. HOR ⁇ iO ⁇ or HOSiO 3 2 groups) in the silicone resin be below 0.7% by weight of the total weight of the silicone resin, alternatively below 0.3%.
- Silicon-bonded hydroxyl groups formed during preparation of the silicone resin are converted to trihydrocarbylsiloxy groups or a hydrolyzable group by reacting the silicone resin with a silane, disiloxane or disilazane containing the appropriate terminal group.
- Silanes containing hydrolyzable groups are typically added in excess of the quantity required to react with the silicon-bonded hydroxyl groups of the silicone resin.
- the organopolysiloxane useful herein is comprised of difunctional units of the formula R R SiO and terminal units of the formula R a X' 3 - a SiG- wherein R is an alkoxy group or a monovalent unsubstituted or substituted hydrocarbon radical; R is a unsubstituted or substituted monovalent hydrocarbon radical; R 4 is aminoalkyl or R 1 group X' is a hydrolyzable group; G is a divalent group linking the silicon atom of the terminal unit with another silicon atom and a is 0 or 1.
- the organopolysiloxane can optionally contain up to about 20 percent, based on total of trifunctional units of the formula R 3 SiO 3/2 where R 3 is as described previously. At least 50 percent, typically at least 80 percent, of the radicals represented by R 2 and R 3 in the R 2 R 3 SiO units are lower alkyl such as methyl.
- the terminal units present on the organopolysiloxane are represented by the formula R 4 a X' 3 . a SiG-, where X' is a hydrolyzable group, R 4 is aminoalkyl or R 1 , G is a divalent group linking the silicon atom of the terminal unit with another silicon atom and a is 0 or 1.
- the organopolysiloxane contains an average of two or more hydrolyzable(X') groups per molecule in order to form a crosslinked product.
- Typical hydrolyzable groups represented by X' include but are not limited to hydroxy, alkoxy such as methoxy and ethoxy, alkenyloxy such as isopropenyloxy, ketoximo such as methyethylketoximo, carboxy such as acetoxy, amidoxy such as acetamidoxy and aminoxy such as N,N-dimethylaminoxy.
- the groups represented by X' can be alkoxy, ketoximo, alkenyloxy, carboxy, aminoxy or amidoxy.
- X' is typically alkoxy and R 5 is alkyl such as methyl or ethyl, or aminoalkyl such as aminopropyl or 3-(2- aminoethylamino)propyl.
- the amino portion of the aminoalkyl radical can be primary, secondary or tertiary.
- the terminal unit G is a divalent group or atom that is hydrolytically stable.
- hydrolytically stable it is meant that it is not hydrolyzable and links the silicon atom(s) of the terminal unit to another silicon atom in the organopolysiloxane such that the terminal unit is not removed during curing of the composition and the curing reaction is not adversely affected.
- Hydrolytically stable linkages represented by G include but are not limited to oxygen, hydrocarbylene such as alkylene and phenylene, hydrocarbylene containing one or more hetero atoms selected from oxygen, nitrogen and sulfur, and combinations of these linking groups.
- G can represent a silalkylene linkage such as -(OSiMe 2 )CH 2 CH 2 -, -(CH 2 CH 2 SiMe 2 )(OSiMe 2 )CH 2 CH 2 -, -(CH 2 CH 2 SiMe 2 )O-, (CH 2 CH 2 SiMe 2 )OSiMe 2 )O-, -(CH 2 CH 2 SiMe 2 )CH 2 CH 2 - and -CH 2 CH 2 -, a siloxane linkage such as -(OSiMe 2 )O- or, more preferably, an oxygen atom.
- Me in these formulae represents methyl and Et represents ethyl.
- X' contains an alkoxy group
- R 4 a X' 3 _ a SiG- would be (MeO) SiCH 2 CH 2 Si(Me 2 )O-.
- Methods for converting alkoxy groups to trialkoxysilylalkyl groups are described in the prior art. For example, moisture reactive groups having the formulae (MeO) 3 SiO- and Me(MeO) 2 SiO- can be introduced into a silanol- terminated polyorganosiloxane by compounds having the formulae (MeO) Si and Me(MeO) 3 Si, respectively.
- the organopolysiloxane used in the hot melt adhesive is preferably a polydimethylsiloxane containing three alkoxy or ketoximo groups, two ketoximo groups or two alkoxy groups together with either an alkyl or aminoalkyl radical.
- the viscosity of the organopolysiloxane should be in the range of 0.02 Pa-s to 100 Pa-s at 25 °C, typically 0.35 to about 60 Pa-s.
- the silicone resin and organopolysiloxane are present in amounts to provide 55 to 75% resin solids based on the amount of silicone resin and organopolysiloxane. Higher amounts of resin can be used however, higher application temperatures will be needed to apply the moisture curable hot melt adhesive composition to a substrate.
- the silane crosslinker is represented by the formula R ⁇ SiZ ⁇ - n ), where R 1 is as described previously and Z is a hydrolyzable group that reacts with the terminal groups of at least the organopolysiloxane under ambient conditions to form a cured material and n is 0, 1 or 2.
- R 1 is an alkyl and/or a phenyl group.
- Suitable hydrolyzable groups represented by Z include but are not limited to alkoxy containing from 1 to 4 carbon atoms, carboxy such as acetoxy, ketoximo such as methylethylketoximo and aminoxy.
- Suitable silane crosslinkers include but are not limited to methyltrimethoxysilane, isobutyltrimethoxysilane, methyltris(methylethylketoximo)silane, methyltriethoxysilane, isobutyltriethoxysilane, methyltriacetoxysilane and alkyl orthosilicates such as ethyl orthosilicate.
- the amount of silane crosslinker used is in the range of 0.5 to 15 parts per hundred based on the amount of silicone resin and polymer, typicallyl to 8 pph. If too much silane crosslinker is present, the green strength and/or cure rate of the hot melt adhesive will decrease. If the silane crosslinker is volatile it may be necessary to use an excess amount to achieve the 1.5 to 15 pph in the final hot melt adhesive composition. One skilled in the art will be able to determine the amount need to produce a composition with 1.5 to 15 pph.
- a titanate catalyst is typically used in the hot melt adhesive formulation except when the organopolysiloxane and/or the silane crosslinker contains ketoxime functional groups.
- the titanate catalyst is an organotitanium compound such as tetrabutyl titanate and partially chelated derivatives of these salts with chelating agents such as acetoacetic acid esters and beta-diketones.
- the amount of titanate catalyst used is in the range of 0.01-2 pph based on the amount of resin and polymer, typically in the range of 0.05-1. If too much titanate catalyst is added then the cure of composition will be impaired. Additionally, as the amount of catalyst is increased the viscosity of the hot melt adhesive increases resulting in higher melt temperature required to apply the material.
- the hot melt adhesive composition may contain 0.05-2 pph based on resin and polymer of an adhesion promoter.
- Adhesion promoters are known in the art and are typically silanes having the formula R C R d$i(OR)4-( c +d) where R is independently a substituted or unsubstituted, monovalent hydrocarbon group having at least 3 carbon atoms and R contains at least one SiC bonded group having an adhesion-promoting group, such as amino, epoxy, mercapto or acrylate groups, c has the value of 0 to 2 and d is either 1 or 2 and the sum of c+d is not greater than 3.
- the adhesion promoter can also be a partial condensate of the above silane.
- the hot melt adhesive composition may contain 0.1 to 40 wt% based on total adhesive of a treated and/or untreated filler.
- suitable fillers include calcium carbonates, fumed silica, silicate, metal oxides, metal hydroxides, carbon blacks, sulfates or zirconates.
- Solvent is typically used in producing the hot melt adhesive. Solvent aids with the flow and introduction of the silicone resin and organopolysiloxane polymers. However, essentially all of the solvent is removed in the continuous process for producing the hot melt adhesive. By essentially it is meant that the hot melt adhesive composition should contain no more than 0.05 to 5 wt.%, preferably less than 0.5 % solvent based on the weight of the hot melt adhesive. If too much solvent is present the viscosity of the hot melt adhesive will be too low and the product performance will be hindered. [0039] Solvents used herein are those that help fluidize the components used in producing the hot melt adhesive but essentially do not react with any of the components in the hot melt adhesive.
- Suitable solvents are organic solvents such as toluene, xylene, methylene chloride, naptha mineral spirit and low molecular weight siloxanes.
- the silicone resin, organopolysiloxane, silane crosslinker, solvent and any optional ingredients are fed into a continuous mixing device.
- the order of addition into the continuous mixing device is not critical to produce the hot melt adhesive composition. If the resin has typically more than 0.7 wt% silanol it is desirable to add the silane crosslinker and/or catalyst and resin together to allow for any reaction to take place and the reaction product (i.e. volatiles) to be removed.
- the continuous mixing device should be capable of mixing the ingredients and should include means for removing the solvent. Typically an extrusion device is used and more typically a twin-screw extrusion device is used.
- the components are fed into the extruder and heated to a temperature in the range of 50 to 250 C, alternatively 80 to 150 °C. By heating the composition in the extruder the viscosity is lowered to allow for adequate mixing the ingredients.
- the silicone resin and organopolysiloxane and solvent are fed into the device.
- the silane crosslinker and optional catalyst may also be added at this point or they may be added further downstream in the device after some mixing has taken place.
- T The continuous process of hot melt adhesives on a co-rotating twin-screw extruder is described in T.
- the solvent is removed during the continuous mixing process.
- vacuum is applied on the continuous mixing device to facilitate removal of the solvent and any other volatile components that may be in the hot melt adhesive composition. Vacuum may be applied in a single or multiple stages on the continuous mixing device. It has been found that the use of multiple vacuum stages provides improved removal to the solvent.
- the silane crosslinker may be volatile, it is preferable to add the silane crosslinker after most of the solvent has been removed to prevent removal of the crosslinker with the solvent.
- the hot melt adhesive composition can be used adhere at least two substrates together.
- the hot melt adhesive composition is used as a layer between the two substrates to produce a laminate of the first substrate, the cured hot melt adhesive and the second substrate.
- the laminate structure produced herein is not limited to these three layers. Additional layers of cured adhesive and substrate may be applied.
- the layer of hot melt adhesive composition in the laminate may be continuous or discontinuous.
- a continuous layer may be used to form a laminate a such as the window 100 shown below in Figure 1.
- a discontinuous layer may be used to form a laminate such as the housing 200 with a lid seal shown below in Figure 2.
- Suitable substrates to which the hot melt adhesive composition, or cured product thereof, may be applied include, but are not limited to, glass; metals, such as aluminum, copper, gold, nickel, silicon, silver, stainless steel alloys, and titanium; ceramic materials; plastics including engineered plastics such as epoxies, polycarbonates, poly(butylene terephthalate) resins, polyamide resins and blends thereof, such as blends of polyamide resins with syndiotactic polystyrene such as those commercially available from The Dow Chemical
- One method for producing the laminate structure is to apply a film of the hot melt adhesive composition on the surface of the first substrate. A surface of the second substrate is then contacted with the hot melt adhesive composition and the first and second surfaces are pressed together.
- Conventional application methods suitable for use with molten materials include, but are not limited to, dipping, spraying, coextrusion, and spreading using heated doctor blades, draw-down bars and calendar rolls.
- the hot melt adhesive composition is applied by heating at a temperature of 80 to 150 °C and applied by pressure through a hose. Equipment of this type is known in the art and commercially available. Upon exposure to moisture the hot melt adhesive composition cures.
- the hot melt adhesive composition may be exposed to moisture by contacting moisture in the air or by direct introduction of moisture such as from contacting the laminate with steam or placing the laminate in a humidity chamber.
- It is also possible to form a laminate by forming a film of the hot melt adhesive composition and then curing the film of the hot melt adhesive composition. A first surface of the cured film is contacted with a surface of the first substrate. A surface of the second substrate is then contacted with the other surface of the cured film and the first and second surfaces are pressed together to form the laminate.
- Another alternative to producing the laminate is to apply a film of the hot melt adhesive composition on the surface of the first substrate. The hot melt adhesive composition is then cured by exposure to moisture to produce the cured film. The second substrate is then contacted with the cured film on the first substrate and the first and second surfaces are pressed together to form the laminate.
- the cured films prepared by curing the hot melt adhesive compositions according to this invention find utility in various industries such as automotive, electronic, construction, space, and medical.
- the cured films may provided bonds that are resistant to hostile environments such as heat and moisture.
- the cured films may be used as conformal coatings for substrates such as printed circuit boards and other substrates containing electrical or electronic components.
- Various laminates may be prepared according to this invention using the hot melt adhesive compositions.
- the laminate may be a portion of an air bag, a car interior, a window, or a lid seal.
- Figure 1 shows a portion of a window prepared according to this invention.
- the window includes a sash 100 on which a film of the hot melt adhesive composition 101 is applied.
- An insulating glass unit 102 comprised of two panes of glass 103, 104 separated by a spacer 105 is applied to the film of the hot melt adhesive composition 101.
- the film of hot melt adhesive composition 101 may be cured before application to the sash 100, after application to the sash 100, before application to the insulating glass unit 102, or after application to the insulating glass unit 102.
- the two panes of glass 103, 104 may be attached to the spacer 105 by films of the hot melt adhesive composition 106.
- the films of hot melt adhesive composition 106 may be cured before application to the pane of glass 103 or 104, after application to the pane of glass 103 or 104, before application to the spacer 105 or after application to the spacer 105.
- FIG. 2 shows a schematic representation of a housing 200 for an electronic component 204 with a lid seal prepared according to this invention.
- the housing 200 may be prepared by, for example, (1) applying the hot melt adhesive composition 201 described above onto the rim of a first substrate shown here as a container 202, (2) placing a second substrate shown here as a lid 203 over the container 202 such that the edges of the lid 203 are in contact with the hot melt adhesive composition 201, and (3) curing the hot melt adhesive composition 201 to form a lid seal between the container
- the hot melt adhesive composition may be applied to the edges of the lid 203 first and thereafter the lid 203 placed onto the container 202.
- curing the hot melt adhesive composition 201 may be performed before, during, or after application to one or both of the substrates (lid 203 and container 202).
- the hot melt adhesive composition or hot melt adhesive formed by curing the hot melt adhesive composition may be applied at the edges of the lid after the lid has been placed onto the container.
- Resin A a xylene soluble resinous copolymer containing triorganosiloxy units and SiO 2 units in the molar ratio of 0.8 mol of triorganosiloxy units per mol of SiO 2 units, where the triorganosiloxy units are trimethylsiloxy and dimethylvinylsiloxy and the copolymer contains 1.9 weight percent of vinyl radicals and 1.5 wt% Si bonded hydroxy groups.
- the resin is dissolved in xylene to produce a solution of 70 wt% solids
- Resin B a xylene soluble resinous copolymer containing triorganosiloxy units and SiO 2 units in the molar ratio of 0.8 .
- the resin is capped with trimethylsiloxy groups to produce a resin with 0.7 % by weight of Si bonded hydroxyl groups.
- the resin is dissolved in xylene to produce a solution of 60 wt% solids.
- Polymer A a primarily linear polydimethylsiloxane polymer of approximate viscosity 70,000 cs, terminated by -CH 2 CH 2 Si(OMe) 3 end groups.
- Polymer B a primarily linear polydimethylsiloxane polymer of approximate viscosity 70,000 cs, approximately 80 % of the ends terminated by
- Polymer C a primarily linear hydroxyl endblocked polydimethylsiloxane fluid having a viscosity of 50 Pa-s and 25 °C.
- Crosslinkers a primarily linear hydroxyl endblocked polydimethylsiloxane fluid having a viscosity of 50 Pa-s and 25 °C.
- Alkoxy silane A i-Bu Si(OMe)3, isobutyltrimethoxysilane
- Alkoxy silane B MeSi(OMe)3, methyltrimethoxysilane
- Oxime silane C Methyltri(ethylmethylketoxime) silane
- Oxime silane D Vinyltri(methylethylketoxime)silane
- Alkoxy silane C NH2CH 2 CH2NHCH2CH 2 CH2Si(OMe)3
- Alkoxy silane D reaction mixture of 74 parts by weight (pbw) of glycidoxypropyltrimethoxy silane and 26 pbw of aminopropyltrimethoxysilane prepared by mixing the silanes and allowing to stand for 16 hrs at room temperature.
- CaCO3 - a ground calcium carbonate of average 2 micron particle size, treated with stearate.
- Titanate catalyst A Ti(OtBu)4 , tetra - tertiary butyl titanium
- Titanate catalyst B Ti(OBu)4, tetra - n butyl titanium
- Titanate catalyst C Ti(iOPr)2(EAA)2 - diisopropoxy bis-ethylacetoacetato titanium
- Tin catalyst D Dibutyl tin dilaurate
- NVC non- volatile content
- Example 1 shows the impact of vacuum and rpm on nvc and viscosity.
- Example 2 show the impact of varying catalyst levels on viscosity at two different resin contents.
- Examples 3 shows the impact of crosslinker volatility on nvc and viscosity.
- Example 4 shows that a partially capped polymer can be used to make the hot melt adhesive.
- Example 5 shows primarily the impact of vacuum on nvc. In these cases the Me3 capped resin is used. The last 3 samples are replicates of each other.
- Example 7 shows that other titanate catalysts can be used to make the hot melt adhesives.
- Example 8 shows that fillers and adhesion promoters may be used.
- Example 9 shows that useful hot melt materials may be prepared with oxime cure.
- the resin and polymer were pre-mixed in tank, then transferred to another tank which was used to feed the compounder (both tanks can be heated, the resin and polymer mixture feed temperature is noted below ); three vacuum stages were used to remove solvent from the process, the three vacuum stages were at 13.93D, 20.86D, and 30.87D; a mixture of crosslinker and catalyst was loaded at 35.87D; a final vacuum was applied at 45.86D.
- Example 10 shows that a hot melt adhesive can be made by feeding the resin and polymer separately from the crosslinker and catalyst. Also shows that the resin and polymer stream can be heated before introducing to the compounder.
- Resin B 65 pbw
- Polymer A 35 pbw
- a pre- mixed slurry of Alkoxy silane A (8 pbw) and Titanate catalyst A 0.1 pbw
- the hot melt sealant was used to prepare a cured film by preparing a film having a 0.254 centimeter (cm) thickness and curing at room temperature for 21 days. The cured film was cut into 2.54 x 2.54 cm pieces.
- Each piece was applied on a first substrate and a second substrate was pressed on top of the cured film piece to prepare a cured film laminate.
- the hot melt sealant was heated to 121 °C and applied on a first substrate.
- a second substrate was pressed on top of the hot melt to produce a 0.254 cm thickness between the first and second substrates to form a wet film laminate. All laminates were cured for at least 21 days at room temperature.
- Table 11 shows the laminate number, substrates used in each laminate, and the shear force measured by Sintech shear testing instrument on each of the laminates after curing.
- G represents glass
- A represents aluminum
- PC represents polycarbonate
- W wood
- Example 11 shows that a hot melt adhesive composition made by the method of this invention effectively laminates a variety of substrates. Comparative Example 1 A sample is prepared by mixing the components in Table 11 A. Table 11 A - Components in Comparative Example 1
- Laminates are prepared using the compositions in Comparative Example 1 and Example 11. Lap shear is measured on the laminates at 0.0847 cm/sec with 6.45 square cm overlap and thickness of 0.254 cm. Lap shear is measured several times as the compositions cure over 14 days. The results are in Table 12.
- the hot melt adhesive compositions and hot melt adhesives prepared by curing the hot melt adhesive compositions find use in the construction and electronics industries.
- the hot melt adhesive compositions and hot melt adhesives may be used in the construction industry, for example, in window applications.
- the hot melt adhesive compositions and hot melt adhesives may be used in the electronics industry, for example, in lid seal applications.
- Figure 1 is a portion of a window prepared according to this invention.
- Figure 2 is a schematic representation of a housing with a lid seal prepared according to this invention.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Laminated Bodies (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004546706A JP2006503958A (en) | 2002-10-22 | 2003-08-19 | Continuous process for producing hot melt adhesive compositions |
EP03809507A EP1554356A2 (en) | 2002-10-22 | 2003-08-19 | Continuous process for producing hot melt adhesive compositions |
CA002503137A CA2503137A1 (en) | 2002-10-22 | 2003-08-19 | Continuous process for producing hot melt adhesive compositions |
AU2003258290A AU2003258290A1 (en) | 2002-10-22 | 2003-08-19 | Continuous process for producing hot melt adhesive compositions |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US42057502P | 2002-10-22 | 2002-10-22 | |
US60/420,575 | 2002-10-22 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2004037941A2 true WO2004037941A2 (en) | 2004-05-06 |
WO2004037941A3 WO2004037941A3 (en) | 2004-07-01 |
Family
ID=32176592
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2003/025951 WO2004037941A2 (en) | 2002-10-22 | 2003-08-19 | Continuous process for producing hot melt adhesive compositions |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP1554356A2 (en) |
JP (1) | JP2006503958A (en) |
KR (1) | KR20050061554A (en) |
AU (1) | AU2003258290A1 (en) |
CA (1) | CA2503137A1 (en) |
WO (1) | WO2004037941A2 (en) |
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WO2007067332A3 (en) * | 2005-12-08 | 2008-04-17 | Dow Corning | Continuous process for production of silicone pressure sensitive adhesives |
US7476416B2 (en) | 2003-11-24 | 2009-01-13 | Intertape Polymer Corp. | Process for preparing adhesive using planetary extruder |
US20100015407A1 (en) * | 2006-12-06 | 2010-01-21 | Anh Be | Airbag and Process for its Assembly |
WO2010008749A1 (en) | 2008-06-24 | 2010-01-21 | Dow Corning Corporation | Hot melt adhesive compositions and methods for their preparation and use |
US7906581B2 (en) * | 2007-09-05 | 2011-03-15 | Xerox Corporation | Method, apparatus and system for preparing adhesive-promoter-treated hot melt adhesives in continuous mode |
CN103087649A (en) * | 2013-02-01 | 2013-05-08 | 上海晶华粘胶制品发展有限公司 | No-solvent hot-melt pressure-sensitive masking tape and manufacturing process thereof |
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WO2014124389A1 (en) * | 2013-02-11 | 2014-08-14 | Dow Corning Corporation | Moisture-curable hot melt silicone adhesive compositions including an alkoxy-functional siloxane reactive resin |
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EP2921527A4 (en) * | 2012-11-13 | 2016-07-06 | Momentive Performance Mat Jp | Room-temperature-curable polyorganosiloxane composition |
DE102015001167A1 (en) | 2015-02-02 | 2016-08-04 | Entex Rust & Mitschke Gmbh | Degassing during the extrusion of plastics |
US9593209B2 (en) | 2009-10-22 | 2017-03-14 | Dow Corning Corporation | Process for preparing clustered functional polyorganosiloxanes, and methods for their use |
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US9862867B2 (en) | 2013-02-11 | 2018-01-09 | Dow Corning Corporation | Alkoxy-functional organopolysiloxane resin and polymer and related methods for forming same |
US9944758B2 (en) | 2013-02-11 | 2018-04-17 | Dow Corning Corporation | Clustered functional polyorganosiloxanes, processes for forming same and methods for their use |
DE102017003681A1 (en) | 2017-04-17 | 2018-10-18 | Entex Rust & Mitschke Gmbh | Cooling when extruding melt |
WO2018188716A1 (en) | 2017-03-05 | 2018-10-18 | Entex Rust & Mitschke Gmbh | Degassing during extrusion of substances, preferably of plastics |
DE102017005999A1 (en) | 2017-05-28 | 2018-11-29 | Entex Rust & Mitschke Gmbh | Production of edible sausage pelts from collagen or similar substances by extrusion |
DE102017005998A1 (en) | 2017-06-23 | 2018-12-27 | Entex Rust & Mitschke Gmbh | Chemical process control for flowable feedstock in a planetary roller extruder |
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US10370574B2 (en) | 2013-02-11 | 2019-08-06 | Dow Silicones Corporation | Method for forming thermally conductive thermal radical cure silicone compositions |
WO2019165251A1 (en) * | 2018-02-22 | 2019-08-29 | Henkel IP & Holding GmbH | Moisture curable silicone polymer and uses thereof |
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WO2019182718A1 (en) * | 2018-03-19 | 2019-09-26 | Dow Silicones Corporation | Hot melt adhesive composition containing a polyolefin - polydiorganosiloxane copolymer and methods for the preparation and use thereof |
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US10493723B2 (en) | 2015-11-05 | 2019-12-03 | Dow Silicones Corporation | Branched polyorganosiloxanes and related curable compositions, methods, uses, and devices |
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DE102020007239A1 (en) | 2020-04-07 | 2021-10-07 | E N T E X Rust & Mitschke GmbH | Cooling when extruding melts |
EP3892441A1 (en) | 2020-04-07 | 2021-10-13 | Entex Rust & Mitschke GmbH | Retrofitting of an extruder system |
TWI809058B (en) * | 2018-03-19 | 2023-07-21 | 美商陶氏全球科技公司 | Polyolefin-polydiorganosiloxane block copolymer and hydrosilylation reaction method for the synthesis thereof |
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-
2003
- 2003-08-19 AU AU2003258290A patent/AU2003258290A1/en not_active Abandoned
- 2003-08-19 EP EP03809507A patent/EP1554356A2/en not_active Withdrawn
- 2003-08-19 KR KR1020057006940A patent/KR20050061554A/en not_active Application Discontinuation
- 2003-08-19 WO PCT/US2003/025951 patent/WO2004037941A2/en active Application Filing
- 2003-08-19 CA CA002503137A patent/CA2503137A1/en not_active Abandoned
- 2003-08-19 JP JP2004546706A patent/JP2006503958A/en active Pending
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Also Published As
Publication number | Publication date |
---|---|
JP2006503958A (en) | 2006-02-02 |
CA2503137A1 (en) | 2004-05-06 |
KR20050061554A (en) | 2005-06-22 |
AU2003258290A1 (en) | 2004-05-13 |
EP1554356A2 (en) | 2005-07-20 |
WO2004037941A3 (en) | 2004-07-01 |
AU2003258290A8 (en) | 2004-05-13 |
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