EP1366129A1 - Adhesif sensible a la pression hydro-desintegrable et procede pour sa fabrication - Google Patents
Adhesif sensible a la pression hydro-desintegrable et procede pour sa fabricationInfo
- Publication number
- EP1366129A1 EP1366129A1 EP02711988A EP02711988A EP1366129A1 EP 1366129 A1 EP1366129 A1 EP 1366129A1 EP 02711988 A EP02711988 A EP 02711988A EP 02711988 A EP02711988 A EP 02711988A EP 1366129 A1 EP1366129 A1 EP 1366129A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- water
- composition according
- weight
- soluble
- monomer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F271/00—Macromolecular compounds obtained by polymerising monomers on to polymers of nitrogen-containing monomers as defined in group C08F26/00
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
-
- 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
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- 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
- C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J151/003—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
Definitions
- the present invention relates to the field of water-disintegrable pressure-sensitive adhesives.
- water-soluble adhesives were manufactured exclusively on the basis of polymers of natural origin, whether chemically modified or not. These polymers such as starch and casein have, however, drawbacks such as their high cost, the variability of the properties linked to products of animal or vegetable origin, their poor aging, etc.
- These drawbacks have justified the development of synthetic substitutes performing similar functions at lower cost.
- These substitutes are generally polymers obtained from acrylic monomers or copolymers comprising acrylic monomers.
- Patent application WO 99/19415 describes pressure-sensitive adhesives (called “pressure sensitive adhesives” or PSA) disintegrable based on latex particles of size less than 200 microns.
- PSA pressure sensitive adhesives
- These adhesives therefore comprise an acrylic copolymer latex, preferably obtained by emulsion polymerization of at least one alkyl acrylate, at least one vinyl ester or styrenic monomer, at least one C 3 carboxylic acid. to C5 polymerizable, and at least one alkyl methacrylate.
- the process for obtaining these adhesives can be carried out by sequential polymerization. It involves the use of at least one, and preferably several, surfactants.
- US Patent 5,536,800 describes pressure-sensitive adhesives dispersible in water obtained by polymerization of alkyl acrylates and of a mixture of acrylic acid and oleophilic unsaturated carboxylic acid. These adhesives are also obtained by emulsion polymerization in the presence of surfactants.
- Pressure-sensitive adhesives are generally obtained by processes of the radical emulsion polymerization type, which lead to aqueous colloidal dispersions called latex.
- surfactants is a generally necessary condition. These surfactants can provide a function, for example, improving the disintegration capacity in an aqueous medium. They are however detrimental to the final properties of the adhesives.
- Emulsion polymerization processes can involve one or more steps with initial loading of all the monomers or continuous addition during the polymerization.
- a first object of the invention relates to pressure-sensitive and hydro-disintegrable adhesive compositions.
- a first embodiment of the invention is a composition of single-phase, translucent or transparent polymer adhesive.
- a second embodiment of the invention is a most often opaque two-phase polymer adhesive composition.
- R 1 is C 1 to C 6 , preferably C 2 to C alkyl
- R 2, equal or different are alkyl to C 6
- X is a monovalent anion, preferably a halide.
- R 2 identical or different, are C 1 to C 6 alkyls.
- it is N, N dimethyl (meth) acryloethylamine.
- non-water-soluble monomer means any monomer whose solubility is better in a non-polar medium than in water.
- one or more non-water-soluble unsaturated monomers are chosen from C 4 -C 20 alkyl acrylates and methacrylates, and styrene and its derivatives, vinyl acetate and their mixtures.
- the (co) polymer of the composition can be crosslinked using a crosslinker.
- the crosslinker makes it possible to improve the cohesion of the adhesive, in particular in the form of a film.
- At least one crosslinker is then added during the polymerization relative to the weight of monomers.
- non-water-soluble unsaturated monomers of Tg greater than 30 ° C. small proportions (0.1 to 10% by weight relative to the total of the water-soluble monomers of this second step), monomers unsaturated non-water-soluble functionalized, in particular carrying a hydroxyl or silane function. Indeed, these are likely to improve the adhesion between the two phases.
- monomers are for example glycidyl methacrylate, gamma-methacryloxy propyltrimethoxysilane or vinyl tri-isopropoxysilane.
- the adhesives can be obtained by a simple manufacturing process. Both types of adhesives (one or two phases) can be obtained by a radical polymerization process in one or two stages. Preferably, the methods are carried out in the absence of surfactants.
- the method of manufacturing adhesive compositions according to the invention, in a polymerization step, comprises the following operations: i) dissolving or dispersing in demineralized water the monomers a, b and c; optionally in the presence of an appropriate crosslinker; ii) polymerization of said solution or dispersion; and iii) adjustment of the water content.
- the solution or dispersion comprises 10 to 80% by weight of monomer.
- a bubbling of nitrogen is established in the reactor for 10 to 30 minutes before the polymerization.
- the polymerization temperature is advantageously between 5 and 90 ° C, preferably between 40 and 80 ° C.
- water-soluble radical initiators are used for the single-phase systems. Any initiation system by thermal decomposition, redox, photonic or other can be used as long as its decomposition kinetics is compatible with the polymerization temperature. 0.005 to 2%, and preferably 0.01 to 0.75% by weight of initiator relative to the weight of monomer is added.
- the water-soluble initiator is added in the form of an aqueous solution (at 0.5 to 2% by weight concentration in demineralized water). It can be added once the reactor is brought to or before reaction temperature.
- Suitable water-soluble radical initiators are, for example, sodium, potassium and ammonium persulfates, hydrogen peroxide, terbutyl hydroperoxide, salts of 4,4'-azo-bis (4-cyanopentanoic acid), 2,2'-azo-bis (2-amidinopropane) di-hydrochloride or redox persulfate / sodium methabisulfite, hydrogen peroxide / vitamin C, terbutyl hydroperoxide / erythorbic acid.
- the end of the polymerization reaction can be detected by returning to the target temperature after an exothermic peak or, under isothermal conditions, by extinguishing the cooling requirements.
- This usually lasts between 1 and 8 hours.
- "cooking” does not cause significant evaporation of water, it therefore takes place at T ⁇ 100 ° C. if the pressure is atmospheric.
- This solution or dispersion leads, after evaporation of the water, to a transparent or translucent single-phase film.
- this film In the dry state, this film is rigid and brittle, but it becomes flexible and adhesive after taking up a small amount of water from the ambient air.
- the adjustment of the water content is carried out by evaporation to complete dryness and recovery of water to the desired water content.
- the first step is the synthesis of a water-soluble or water-disintegrable polymer phase.
- the second phase is polymerized in the presence of this phase.
- this composition it is also possible to obtain this composition by mixing the polymers prepared separately.
- the manufacturing process therefore also comprises, between steps ii) and iii), the steps of: iv) dissolving or dispersing in the product from step ii) from 1 to 75% by weight relative to the total weight of monomers of at least one non-water-soluble unsaturated monomer; and v) polymerization.
- a bubbling with nitrogen is established in the reactor before the reaction for a period ranging from 10 to 30 minutes.
- the polymerization temperature is advantageously between 5 and 90 ° C, preferably between 40 and 80 ° C.
- the polymerization initiator is preferably added in the form of a dilute solution, preferably at 0.5 to 2% by weight concentration.
- Water-soluble or liposoluble radical initiators can be used.
- part of the hydrophobic monomer can serve as a solvent.
- Any initiation system by thermal decomposition, redox, photonic or other can be used as long as its decomposition kinetics is compatible with the polymerization temperature.
- 0.005 to 2% and preferably 0.01 to 0.75% by weight of initiator are added relative to the weight of monomer. The initiator can be added once or before the reaction temperature.
- Liposoluble radical initiators can also be used, alone or in combination with one or more water-soluble initiators.
- organic peroxides such as benzoyl peroxide, azo compounds such as 2,2'-azo-bis-2-methylbutyronitrile and redox couples such as cumene hydroperoxide / thionyl chloride or mixed redox couples (water-soluble-fat-soluble) such as cumene hydroperoxide / sodium methabisulfite.
- the product is cooled and removed from the reactor for storage and property control. It then takes the form of a colloidal dispersion diffusing light ("latex"), analogous to what can be obtained by emulsion polymerization techniques, with a dry extract rate (polymer concentration) between 10 and 60%.
- latex colloidal dispersion diffusing light
- the manufacturing process according to the invention makes it possible to obtain aqueous dispersions of adhesive comprising little or no stabilizing surfactant.
- this film In the dry state, this film is rigid and brittle, but becomes flexible and adhesive after taking up less than 15% by weight, and more particularly, less than 10% by weight of water from the ambient air.
- the assemblies or bondings made with these adhesives exhibit very good aging behavior. They do not deteriorate over time and can be used to stick labels or other objects in conditions where existing pressure sensitive adhesives age poorly; this is particularly the case for bonding on slightly heated surfaces such as computer screens, televisions and other electrical or electronic devices or which may be exposed to alternating humidity.
- the adhesives according to the invention can be used for temporary or removable bonding on interior surfaces in fields as varied as decoration, labeling of electrical appliances or display, among others.
- the adhesive properties of the films are particularly resistant to aging and the assemblies made with these films can withstand humid atmospheres and heat. The assembly can be separated and any traces left on the support can be removed with a damp sponge, the sponge then rinsed with water.
- the adhesive composition according to the invention can be in the form of films. These films can advantageously be on a non-sticky transfer support. This makes it easier to apply the adhesive to the object to be bonded.
- the adhesive can be used for bonding any type of support, and more particularly metal, paper, glass, wood and plastic.
- the implementation of the adhesive can be done according to any of the known bonding methods for pressure-sensitive adhesives.
- they comprise the application of the composition according to the invention to one or both surfaces to be bonded, and the application of pressure to the assembly.
- composition according to the invention can also be envisaged to apply the composition according to the invention to one or both surfaces to be bonded, to adjust the water content to the desired water content, then to apply pressure on the assembly.
- the adhesives according to the invention can be used alone or as existing adhesive additives (whether or not they are pressure sensitive). Thus, they can be useful in all the applications in which hydro-disintegrating adhesives are recommended, such as wallpaper adhesives, adhesives for temporary coatings, adhesives for paper and packaging, adhesives for DIY and repairs, etc. The invention is described in more detail below.
- Synthesis of the hydro-disintegrable polymer for a single-phase adhesive 442 g of demineralized water are loaded into a polymerization reactor equipped with a double jacket allowing the circulation of a heat-transfer fluid to heat / cool the system, a tapping allowing the introduction of nitrogen gas to expel oxygen which inhibits the polymerization reaction, an agitator in the form of an anchor linked to a motor making it possible to rotate at variable speed, an inlet allowing the addition of additives a vapor outlet linked to a condensation / reflux system.
- 160 g of acryloethyltrimethylammonium chloride (ADAMQUAT MC80 from ATOFINA at 80% active material, 200 g of commercial product) are introduced into the reactor.
- the double jacket temperature of the reactor is brought to 30 ° C.
- the stirring speed is fixed at 400 revolutions per minute.
- a nitrogen sweep is applied for 15 minutes.
- the priming solution is injected into the reaction medium (0.325 g of potassium persulfate + 24.465 g of demineralized water).
- the jacket temperature is then brought to 75 ° C (tO).
- the temperature double jacket is brought to 80 ° C.
- the temperature of the reaction medium is brought to 85 ° C. for 3 hours.
- the temperature of the final aqueous solution is brought to 30 ° C.
- the reactor is then drained.
- the final dry extract, measured by gravimetry, of the solution (called solution 1) is 26.34% by weight.
- ADAMQUAT MC80 from ATOFINA at 80% of active material, 125
- NMBA N, N'-methylene-bis-acrylamide
- the double jacket temperature of the reactor is brought to 30 ° C.
- the stirring speed is fixed at 400 revolutions per minute.
- a nitrogen sweep is applied for 15 minutes.
- the priming solution is injected into the reaction medium (0.195 g of potassium persulfate + 20 g of demineralized water).
- the jacket temperature is then brought to 75 ° C (tO).
- the jacket temperature is brought to 80 ° C.
- the temperature of the reaction medium is brought to 85 ° C for 3 hours.
- the temperature of the final aqueous solution is brought to 30 ° C.
- the reactor is then drained.
- the final experimental dry extract, measured by gravimetry, of the solution (called solution 2) is 25% by weight.
- 351 g of demineralized water, 232 g of solution 2 (58 g of polymer) and 70 g of styrene are loaded into a polymerization reactor equipped as described in Example 1. The jacket temperature is brought to 30 ° C.
- Synthesis of a multiphase adhesive with a phase weight ratio of 35/65 and a weight rate of crosslinking of the continuous phase of 1000 ppm 401 g of demineralized water are loaded into a polymerization reactor equipped as described in Example 1. Then, 216 g of acryloethyltrimethylammonium chloride (ADAMQUAT MC80 from ATOFI A with 80% active material, 270 g of commercial product), 0.216 g of N, N'-methylene-bis-acrylamide (NMBA) are introduced into the reactor. , 1000 ppm compared to pure ADAMQUAT). The double jacket temperature of the reactor is brought to 30 ° C. The stirring speed is fixed at 400 revolutions per minute. A nitrogen sweep is applied for 15 minutes. After these 15 minutes of degassing, the priming solution is injected into the reaction medium (0.44 g of potassium persulfate + 50 g of demineralized water). The jacket temperature is then brought to 75 ° C (tO).
- the jacket temperature is brought to 80 ° C.
- the temperature of the reaction medium is brought to 85 ° C. for 3 hours.
- the temperature of the final aqueous solution is brought to 30 ° C.
- the reactor is then drained.
- the final experimental dry extract, measured by gravimetry, of the solution (called solution 4) is 30% by weight. 423.1 g of demineralized water are loaded, 188.3 g of solution 4 (56.5 g of polymer) and
- Example 1 105 g of styrene in a polymerization reactor equipped as described in Example 1.
- the jacket temperature is brought to 30 ° C, the stirring speed is fixed at 400 revolutions per minute.
- a nitrogen sweep is applied for 15 minutes.
- 309.8 g of demineralized water, 399 g of solution 1 (105 g of polymer) and 35 g of styrene are loaded into a polymerization reactor equipped as described in example 1.
- the jacket temperature is brought to 30 ° C, the stirring speed is fixed at 400 revolutions per minute. A nitrogen sweep is applied for 15 minutes. After this degassing phase, half of the following initiator solution is added to the mixture: 0.14 g of potassium persulfate + 20 g of demineralized water.
- the jacket temperature is brought to 75 ° C (tO).
- the jacket temperature is brought to 80 ° C and the other half of the initiator solution is injected into the reaction medium.
- the temperature of the reaction medium is brought to 85 ° C. for 3 hours.
- the temperature of the final product is brought to 30 ° C., the reactor is then drained.
- the final experimental dry extract, measured by gravimetry, is 18% by weight.
- the product is in the form of a colloidal dispersion with a milky appearance (called "latex 5").
- a film about 0.5 mm thick is prepared by slow evaporation of water (50 ° C) from a sample of solution or latex in a ventilated oven.
- the dry film taken out of the oven is rigid, brittle and has no surface tack. After a few hours in the ambient air.
- the film absorbs water from the ambient air and becomes soft, very sticky and no longer brittle.
- the water content of the films is determined by gravimetry. For this, the film is weighed and then dried in an oven at 105 ° C for two hours. The film is weighed after drying, and the difference in weight to determine the humidity.
- 10x10 mm samples are subjected to a shear creep test by applying a force of 0.3N using a DMA 2980 device from TA Instruments. After 30 minutes, the deformation achieved by the samples and the practically constant rate of deformation of the samples are measured.
- the adhesives of the examples can be used as a solid adhesive (the water which they then contain is only the residual moisture making it possible to activate the adhesive, ie ⁇ 15% and preferably less than 10% by weight) for sticking sheets of paper on wall posters, for the posters themselves, for frames and calendars, for objects in alternating humid atmospheres, such as bathrooms, for repair by sticking wallpaper , for example.
- the bondings made with the adhesive show very good aging. In fact, we do not observe take-off over time of labels and sticky notes, even on slightly heated media such as computer screens.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0100594A FR2819521B1 (fr) | 2001-01-17 | 2001-01-17 | Adhesif sensible a la pression hydro-desintegrable et procede pour sa fabrication |
FR0100594 | 2001-01-17 | ||
PCT/FR2002/000183 WO2002057385A1 (fr) | 2001-01-17 | 2002-01-17 | Adhesif sensible a la pression hydro-desintegrable et procede pour sa fabrication |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1366129A1 true EP1366129A1 (fr) | 2003-12-03 |
Family
ID=8858917
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP02711988A Withdrawn EP1366129A1 (fr) | 2001-01-17 | 2002-01-17 | Adhesif sensible a la pression hydro-desintegrable et procede pour sa fabrication |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP1366129A1 (fr) |
FR (1) | FR2819521B1 (fr) |
WO (1) | WO2002057385A1 (fr) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20050161152A1 (en) * | 2004-01-23 | 2005-07-28 | Hoffmann Dennis Sr. | Pressure sensitive adhesive repair product |
FR3068706A1 (fr) | 2017-07-04 | 2019-01-11 | Arkema France | Materiau absorbant pour la protection des dispositifs electroniques |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE859625A (fr) * | 1977-10-12 | 1978-04-12 | Northern Illinois Res Inc | Composition a base de matiere plastique |
EP0077618B1 (fr) * | 1981-10-15 | 1986-12-17 | Ciba Specialty Chemicals Water Treatments Limited | Adhésifs pour papiers de tenture préencollés |
DE3924393A1 (de) * | 1989-07-24 | 1991-01-31 | Roehm Gmbh | Wasserloeslicher druckempfindlicher hauthaftkleber, dessen verwendung und damit ausgeruestete mittel |
US5614586A (en) * | 1994-04-06 | 1997-03-25 | Graphic Controls Corporation | Polyacrylate and Polymethacrylate ester based hydrogel adhesives |
JPH10504596A (ja) * | 1994-08-19 | 1998-05-06 | ミネソタ マイニング アンド マニュファクチャリング カンパニー | 水性接着剤 |
-
2001
- 2001-01-17 FR FR0100594A patent/FR2819521B1/fr not_active Expired - Fee Related
-
2002
- 2002-01-17 EP EP02711988A patent/EP1366129A1/fr not_active Withdrawn
- 2002-01-17 WO PCT/FR2002/000183 patent/WO2002057385A1/fr not_active Application Discontinuation
Non-Patent Citations (1)
Title |
---|
See references of WO02057385A1 * |
Also Published As
Publication number | Publication date |
---|---|
FR2819521A1 (fr) | 2002-07-19 |
WO2002057385A1 (fr) | 2002-07-25 |
FR2819521B1 (fr) | 2006-11-17 |
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