WO1993018105A1 - Procede de fabrication d'une colle a base de dispersion aqueuse - Google Patents

Procede de fabrication d'une colle a base de dispersion aqueuse Download PDF

Info

Publication number
WO1993018105A1
WO1993018105A1 PCT/PL1993/000002 PL9300002W WO9318105A1 WO 1993018105 A1 WO1993018105 A1 WO 1993018105A1 PL 9300002 W PL9300002 W PL 9300002W WO 9318105 A1 WO9318105 A1 WO 9318105A1
Authority
WO
WIPO (PCT)
Prior art keywords
weight parts
copolymer
adhesive
epoxide resin
aqueous dispersion
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/PL1993/000002
Other languages
English (en)
Inventor
Piotr Penczek
Henryk Staniak
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Łukasiewicz Research Network - Industrial Chemistry Research Institute
Original Assignee
Łukasiewicz Research Network - Industrial Chemistry Research Institute
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Łukasiewicz Research Network - Industrial Chemistry Research Institute filed Critical Łukasiewicz Research Network - Industrial Chemistry Research Institute
Publication of WO1993018105A1 publication Critical patent/WO1993018105A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • 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
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • 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
    • C09J111/00—Adhesives based on homopolymers or copolymers of chloroprene
    • 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
    • C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
    • C09J123/02—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers not modified by chemical after-treatment
    • C09J123/04—Homopolymers or copolymers of ethene
    • C09J123/08—Copolymers of ethene
    • C09J123/0846—Copolymers of ethene with unsaturated hydrocarbons containing other atoms than carbon or hydrogen atoms
    • C09J123/0853—Vinylacetate
    • 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
    • C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
    • C09J123/02—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers not modified by chemical after-treatment
    • C09J123/04—Homopolymers or copolymers of ethene
    • C09J123/08—Copolymers of ethene
    • C09J123/0846—Copolymers of ethene with unsaturated hydrocarbons containing other atoms than carbon or hydrogen atoms
    • C09J123/0869—Acids or derivatives thereof
    • 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
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/08—Homopolymers or copolymers of acrylic acid esters
    • 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
    • C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
    • C08L2666/14—Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
    • 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
    • C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
    • C08L2666/14—Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
    • C08L2666/22—Macromolecular compounds not provided for in C08L2666/16 - C08L2666/20
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • 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
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
    • C09J2301/302—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C

Definitions

  • This invention relates to a method of making a water resistant, aqueous disperion-based adhesive.
  • the said adhesive is a two-component one and contains high molecular weight copolymers as its main component.
  • the adhesive is recommended mainly for bonding plastic flooring to concrete substrate.
  • aqueous dispersion-based adhesives known in the art have unsatisfactory resistance to long-term exposure to water. Moreover, the known adhesives cannot be used for bonding plastic flooring to wet, freshly prepared concrete.
  • An example of such known adhesive is an aqueous dispersion-based adhesive manufactured by BASF.
  • Main component of BASF adhesive is a product of acrylic esters copolymerization sold under a trade name Acronal V-271. This adhesive contains also: a filler, an emulsifier, large amount of resin (in toluene solution) and other additives. This adhesive has good bond strength when bonding plasticized PVC flooring, but its resistance to long-term exposure to water is limited.
  • Polychloroprene latex-based adhesives are widely used for' bonding a variety of materials. It became possible because many different natural and synthetic resins, other lattexes and aqueous dispersions or emulsions of various polymers as well as starch, proteins and other additives usually applied to modify the processing and application properties of the adhesive have been introduced to the basic adhesive binder—a chloroprene copolymer. Coalescing agents and sometimes solvents have been also used to get a continuous adhesive film.
  • Low glass transition temperature of chloroprene copolymer is of great importance to ensure a good tack of the adhesive.
  • resins of appropriate softening temperature in order to get good coalescence and good properties of the adhesive bonds.
  • One of the few disadvantages of polychloroprene rubber-based adhesives is low initial resistance to water. Water resistance of the adhesive bonds made using aqueous dispersions of ethylene vinyl acetate copolymers is also unsatisfactory.
  • aqueous dispersions of acrylic copolymers containing epoxide, imine or amide groups in the molecule are used in coatings to improve their weathering characteristics and thus also water resistance.
  • First component is epoxide groups containing acrylic copolymer (product of copolymerization of acrylic esters, mainly methyl acrylate and methyl methacrylate, styrene and glicydyl methacrylate)
  • second component is an ether bond containing high molecular weight aliphatic diamine of molecular weight below 5000.
  • the first component is an i ine group containing acrylic copolymer (product of copolymerization of acrylic acid esters, methacrylic acid esters, unsaturated monomers, e.g. styrene, acrylonitrile, and unsaturated hydrocarbons with unsaturated carboxylic acids being then partially or totally reacted with alkyleneimine.
  • the second component is water-dispersed solid epoxide resin of very high molecular weight (40,000 to 60,000).
  • U. S. Patent 4,289,674 teaches about aqueous dispersions obtained by combining an amide group containing aqueous dispersions of acrylic copolymers (obtained by solution copolymerization of N-methoxyacrylamide, or N-methoxymethacrylamide, unsaturated carboxylic acids and a vinyl monomer) with high molecular weight, solid epoxide resin dispersed in water.
  • Room temperature-crosslinkable coatings or adhesive films can be obtained from such known products composed of solid constituents only when they contain organic solvents.
  • the objective of this invention was to develop a process of manufacturing solventless, water-resistant adhesives that can be applied for bonding substrates soaked with water and that would yield adhesive bonds resistant to long-term exposure to water.
  • the additional objective of this invention is to reach this goal by using aqueous dispersions of standard, simple copolymers that would not contain any reactive functional groups, small amount of carboxylic groups that would help in getting stable aqueous dispersion being an exception.
  • Amount of polyaminoamide is 20 to 100 pph (parts by weight per 100 parts by weight) of epoxide resin, preferably 40 to 70 pph of epoxide resin.
  • Amount of epoxide resin is 5 to 50 pph of polymer dispersion, preferably 10 to 30 pph of polymer dispersion. It is preferred to use the epoxide resin being previously modified by addition of either an aliphatic amine or a cycloaliphatic amine bearing primary or secondary amine group or by addition of a monocarboxylic acid, said acid being preferably lactic acid. while less than 5% of epoxide groups participate in said addition reaction.
  • Liquid emulsion of polyaminoamide curing agent in water or in aqueous copolymer dispersion is preferably prepared with an addition of from 1 to 10 parts by wt. of salicylic acid or lactic acid, said acid being preferably used in a form of a salt with aliphatic or cycloaliphatic amine bearing at least one primary or secondary amine group in the molecule.
  • the adhesives thus prepared exhibit a bonding ability at temperatures as low as 1-15°C
  • fillers per 100 parts of the dispersion, such as kaolin and bentonite, as well as 2 to 40 parts of commonly known emulsifiers, natural and synthetic resins such as casein, gum acids esters, coumarone resins, urea-formaldehyde resins and melamine-formaldehyde resins per 100 weight parts (pph) of the copolymer may be used in the process of manufacturing the adhesives according to this invention.
  • fillers such as kaolin and bentonite
  • emulsifiers such as casein, gum acids esters, coumarone resins, urea-formaldehyde resins and melamine-formaldehyde resins per 100 weight parts (pph) of the copolymer
  • aqueous dispersion of acrylic copolymer (Acronal V-271) having a glass transition temperature of -25°C is added stepwise to 100 g of the liquid epoxide resin (Epidian 5) while stirring the mixture continuously.
  • Preparation of component II 50 g of water is added to 50 g of polyaminoamide (Versamid 140) while stirring the mixture continuously.
  • 100 g of the acrylic copolymer (Acronal V-271) and 190 g of water are added stepwise. Both components are liquid.
  • the components I and II are blended using a 3:1 weight ratio (respectively).
  • the adhesive is liquid. When the adhesive is used to bond PVC flooring to fresh, wet concrete substrate, satisfactory bond strength and water resistance of the adhesive bonds is achieved.
  • 100 g of water is added slowly to 100 g of the polyaminoamide (Versamid 125) while stirring the mixture continuously followed by the addition of 200 g of Acronal V-271, 100 g of chalk and 100 g of water.
  • a thixotropic adhesive is obtained.
  • the adhesive is used to bond PVC flooring to green concrete substrate, satisfactory bond strength and water resistance of the adhesive bonds are achieved.
  • Example III Preparation of component I: 1000 g of Acronal V-271 is added stepwise to 180 g of the liquid epoxide resin (Epikote 828) while stirring the mixture continuously. Preparation of component II:
  • the adhesive has 3 days pot-life and 2 hrs. open time (after applying onto wet concrete substrate) at 20°C. At bonding PVC tiles to wet concrete at 20°C, the initial bonding time amounts to 24 hrs. Complete curing time is 7 days. When such bonded specimen is soaked in water, no damage of the bond is observed during 6 weeks.
  • a thixotropic adhesive is obtained.
  • the open time is 3 hours at 5°C.
  • Initial curing time is 24 hours.
  • Full curing time is 7 days.
  • lactic acid 3 g of lactic acid is introduced to 180 g of Epidian 5 and the mixture is heated up to 80°C, cooled and 1000 g of aqueous dispersion of chloroprene copolymer (Neoprene Latex 115 - du Pont de Nemours & Company) having a glass transition temperature of -14°C is added while stirring the mixture continuously.
  • aqueous dispersion of chloroprene copolymer 10 g of the above aqueous chloroprene copolymer dispersion and 250 g of water are introduced to 90 g of Versamid 125, while stirring the mixture continuously.
  • a thixotropic adhesive is obtained.
  • the adhesive open time (after applying to wet concrete) is 1.5 hour at room temperature. Full curing time is 7 days. After that time, the immersion in water for 6 weeks does not damage the adhesive bond.
  • Both components are liquid. After the component I and II are blended using 10:4 weight ratio and the adhesive is applied to wet concrete substrate, the adhesive open time is 1.5 hour. Initial curing time is 12 hours. After 72 hours, the adhesive bond is resistant to long-term water exposure.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

Procédé de fabrication d'une colle résistante à l'eau à base d'une dispersion aqueuse. Elle est destinée notamment à coller un revêtement de sol en matière plastique à un substrat en béton. Selon le procédé, on introduit dans une dispersion aqueuse de copolymère éthylène-acétate de vinyle, de copolymère d'ester acrylique, ou de copolymère de chloroprène, de 5 à 50 parties en poids de résine époxyde éventuellement modifiée. Cette quantité est déterminée par rapport à 100 parties en poids desdits copolymères présentant une température de transition vitreuse inférieure à -5 °C. Séparément, on émulsionne dans l'eau, ou dans une dispersion aqueuse dudit copolymère, un agent de durcissement liquide à polyaminoamide. On utilise de 20 à 100 parties en poids de polyaminoamide par 100 parties en poids de résine époxyde, et on mélange les deux constituants de la colle avant d'appliquer celle-ci sur les substrats à coller.
PCT/PL1993/000002 1992-03-10 1993-03-05 Procede de fabrication d'une colle a base de dispersion aqueuse Ceased WO1993018105A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
PL92293774A PL167435B1 (pl) 1992-03-10 1992-03-10 Sposób wytwarzania wodoodpornego kleju wodno-dyspersyjnego PL
PLP-293774 1992-03-10

Publications (1)

Publication Number Publication Date
WO1993018105A1 true WO1993018105A1 (fr) 1993-09-16

Family

ID=20057039

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/PL1993/000002 Ceased WO1993018105A1 (fr) 1992-03-10 1993-03-05 Procede de fabrication d'une colle a base de dispersion aqueuse

Country Status (2)

Country Link
PL (1) PL167435B1 (fr)
WO (1) WO1993018105A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112277392A (zh) * 2020-10-26 2021-01-29 无锡市辰华包装有限公司 一种抗菌防静电瓦楞纸板的制备方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0056452A2 (fr) * 1981-01-19 1982-07-28 National Starch and Chemical Corporation Laminés flexibles et adhésifs pour leur production
EP0338205A1 (fr) * 1987-08-19 1989-10-25 Kawasaki Steel Corporation Composition de revêtement du type adhésif thermodurcissable

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0056452A2 (fr) * 1981-01-19 1982-07-28 National Starch and Chemical Corporation Laminés flexibles et adhésifs pour leur production
EP0338205A1 (fr) * 1987-08-19 1989-10-25 Kawasaki Steel Corporation Composition de revêtement du type adhésif thermodurcissable

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112277392A (zh) * 2020-10-26 2021-01-29 无锡市辰华包装有限公司 一种抗菌防静电瓦楞纸板的制备方法
CN112277392B (zh) * 2020-10-26 2022-05-10 无锡市辰华包装有限公司 一种抗菌防静电瓦楞纸板的制备方法

Also Published As

Publication number Publication date
PL167435B1 (pl) 1995-09-30
PL293774A1 (en) 1993-09-20

Similar Documents

Publication Publication Date Title
EP0035332B2 (fr) Adhésifs pour carreaux en céramique
AU609540B2 (en) Poly(vinylacetate) emulsion adhesives containing an alkoxysilane
JPH03279247A (ja) 重合体変性セメント質組成物
US4880931A (en) Acryloxy-containing compounds
WO1994009068A1 (fr) Nouveaux polymeres en emulsion ionique, et leur preparation
JPH06510559A (ja) ビニルポリマーラテックス系
CA1296120C (fr) Adhesif pour revetement de sol, a base de dispersions polymeriques aqueuses
FI96215C (fi) Vinyylikopolymeeri ja menetelmä sen valmistamiseksi
JP3155480B2 (ja) 一液常温架橋型エマルジョン組成物およびその製法
JPH023461A (ja) 非粘着性の汚れにくい柔軟な塗料のための結合剤
US4268548A (en) Polyvinyl chloride-plastisol having improved adhesion
JPH08231616A (ja) 硬化性水性樹脂組成物
JPS6131124B2 (fr)
PL167435B1 (pl) Sposób wytwarzania wodoodpornego kleju wodno-dyspersyjnego PL
PL170012B1 (pl) Sposób wytwarzania dwuskładnikowego wodoodpornego kleju wodno-dyspersyjnego
JPS6134745B2 (fr)
JPH03217478A (ja) 静電植毛用接着剤
GB2136003A (en) Contact adhesives
JP2939324B2 (ja) 速硬化水性接着剤及び接着方法
JP3034597B2 (ja) 速硬化水性接着剤と接着方法
US3282881A (en) Hot-melt adhesive compositions consisting essentially of ethylene-vinyl acetate and chlorinated terphenyls
JP4282150B2 (ja) 水性樹脂組成物
JPH0662914B2 (ja) エマルシヨン塗料組成物
JPH0673308A (ja) 一成分系水性プライマー組成物
PL170834B1 (pl) Sposób wytwarzania wodoodpornego przylepcowego kleju wodno-dyspersyjnego

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): CZ RU UA

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE DE ES FR GB IT NL SE

WWW Wipo information: withdrawn in national office

Ref document number: 1993905669

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 1993905669

Country of ref document: EP

122 Ep: pct application non-entry in european phase