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WO1992000363A1 - Application et composition adhesive thermofusible dispersible dans l'eau - Google Patents

Application et composition adhesive thermofusible dispersible dans l'eau Download PDF

Info

Publication number
WO1992000363A1
WO1992000363A1 PCT/GB1991/001006 GB9101006W WO9200363A1 WO 1992000363 A1 WO1992000363 A1 WO 1992000363A1 GB 9101006 W GB9101006 W GB 9101006W WO 9200363 A1 WO9200363 A1 WO 9200363A1
Authority
WO
WIPO (PCT)
Prior art keywords
adhesive composition
weight
water dispersible
compatible
molecular weight
Prior art date
Application number
PCT/GB1991/001006
Other languages
English (en)
Inventor
Frank Bozich
Original Assignee
Enbond Limited
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 Enbond Limited filed Critical Enbond Limited
Publication of WO1992000363A1 publication Critical patent/WO1992000363A1/fr

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
    • C09J167/00—Adhesives based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Adhesives based on derivatives of such polymers
    • C09J167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • 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
    • 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
    • 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
    • C08L2666/34—Oxygen-containing compounds, including ammonium and metal salts

Definitions

  • the present invention is directed to a water dispersible hot melt adhesive composition and to "Perfect Bound" books constructed using the adhesive.
  • the adhesive composition of the present invention gives excellent adhesion both to ground wood and newsprint stock, and to high quality coated stock and heavily inked paper.
  • the water dispersible nature of the adhesive of the present invention permits the repulping of books and trimmings made using the adhesive.
  • Telephone directories particularly directories located at outdoor telephones, present a unique variety of problems. These directories occasionally hang in a phone booth with their back (binding side) up and the pages hanging down. When hanging in this fashion, the pages are subject to the constant downward pull of gravity under a variety of weather conditions, including heat and high humidity. The combined conditions of heat and high humidity are particularly adverse for a water dispersible hot melt adhesive composition. It is an object of the present invention to provide a water dispersible hot melt adhesive composition that is capable of functioning reasonably well under conditions of heat and high humidity.
  • the present invention is directed both to a water dispersible hot melt adhesive composition and to a repulpable book bound using the water dispersible adhesive composition.
  • the adhesive composition of the present invention exhibits good tensile strength, page pull, and page flex values, binds well to newsprint and coated stocks, is humidity resistent and is water dispersible. These properties make the adhesive composition of the present invention particularly useful for the perfect binding of repulpable books using both news print paper and high quality coated stocks.
  • the water dispersible adhesive composition of the present invention comprises:
  • the adhesive composition of the present invention may further contain one or more compatible tackifiers in a total amount up to 30% of the weight of the adhesive composition.
  • the present invention also encompasses a repulpable perfect bound book comprising a cover, one or more signatures and the adhesive described above for binding the cover to the one or more signatures in a recyclable manner.
  • the present invention has two aspects. In its first aspect, it is directed to a water dispersible hot melt adhesive composition that is suitable for the preparation of repulpable books.
  • the water dispersible hot melt adhesive composition of the present invention comprises: a) from about 40% to about 95% by weight of a water dispersible ionically substituted polyester resin having a molecular weight from about 10,000 to about 20,000 daltons; b) from about 60% to about 5% by weight of one or more compatible plasticizers; and
  • the adhesive composition may further contain one or more compatible tackifiers comprising up to 30% of the weight of the composition.
  • one or more compatible tackifiers comprising up to 30% of the weight of the composition.
  • a hydrophobic plasticizer is preferably employed.
  • the water dispersible ionically substituted polyester resin component of the adhesive composition is composed of a chain of alternating units of an aromatic dicarboxylic acid ("A") and an aliphatic or cyclo-aliphatic glycol ("G") in sufficient numbers to approximate the average molecular weight range of the polyester resin molecule.
  • a sufficient number of the dicarboxylic acid moieties ("A") in the polyester resin are randomly substituted with a water ionizable species ("X”) to render the polyester resin and adhesive composition water dispersible.
  • X water ionizable species
  • an average of at least 5 of the dicarboxylic acid moieties in any resin molecule are ionically substituted, more preferably from 5 to about 8.
  • a segment of the polyester resin component is schematically represented as Formula I :
  • a and G are as described above; wherein -OH is a terminal hydroxyl group; wherein X is a water ionizable moiety such as -SO-Y, and wherein Y is a water soluble cation such as Li + , Na + , K + , NH 4 + and the like or a mixture thereof.
  • the preferred polyester resin of the present invention has a molecular weight ranging from about 14,000 to about
  • polyester resin for the present invention has a molecular weight of approximately 16,000 daltons, and is commercially available as a solid polymer under the tradename Eastman AQ29S from Eastman
  • Eastman AQ295 has a hydroxyl number of less than 10, an acid number of less than 2, a glass transition temperature of 29°C, and a melt viscosity of 2,000 poise at 200°C.
  • Plasticizers are suited for use in the present invention (i.e., are “compatible”) if they are water soluble or dispersible, or they do not adversely affect tne water dispersibility of the adhesive composition of the present invention.
  • Suitable plasticizers include the various low molecular weight polyethylene glycols and/or glycol ethers, glycerin and the like.
  • low molecular weight as used in conjunction with the polyethylene glycols and/or glycol ethers is meant a glycol and/or glycol ether having an average molecular weight falling within the range from about 200 to about 600.
  • Preferred plasticizers are polyethylene glycol 300 (PEG 300) having an average molecular weight of from about 285 to 315 daltons and polyethylene glycol 400 (PEG 400) having an average molecular weight from about 380-420 daltons.
  • a particularly preferred plasticizer is a combination of PEG 300 and PEG 400 most preferably, in a weight ratio of about 1 to about 8 respectively.
  • Polyethylene glycols are commercially available under the trade name Carbowax® from Dow Chemical Co., Midland, Michigan. The above plasticizer combination is suitable for use in most situations, including high humidity, wherein the pages of the perfect bound book are not subject to constant pulling.
  • At least one of the plasticizers be a relatively hydrophobic plasticizer.
  • a particularly preferred hydrophobic plasticizer is butyl benzyl phthalate [i.e., 1,2-benzenedicarboxylic acid butyl phenylmethyl ester]. This plasticizer is commercially available under the tradename Santicizer ® 160 from Monsanto Company, St. Louis, Missouri 63167.
  • the adhesive composition of the present invention also comprises from about 0.1% to about 1.5% of one or more stabilizers.
  • Preferred stabilizers are of the anti-oxidant type.
  • these anti-oxidants are members of the group consisting of high molecular weight sterically hindered phenols or sulfur or phosphorous substituted phenols.
  • sterically hindered phenols is generally meant those phenols with two isopropyl or preferably tertiary butyl groups ortho to the phenolic hydroxyl groups.
  • sterically hindered phenols include but are not limited to 1,3,5-trimethyl-2,4,6- tris(3,5-di-t-butyl-4-hydroxybenzyl)benzene; pentaerythrityl tetra-kis-3(3,5-di-tertbutyl-4- hydroxyphenyl)propionate; n-octadecyl 3-(3,5-di-tertbutyl- 4-hydroxypheny1)-propionate;4,4'-methylenebis(2,6-tertbutylphenol); 4,4'-thiobis(6-tert-butyl-o-cresol); 2,6-ditertbutylphenol;6-(4-hydroxyphenoxy)-2,4-bis(n-octylthio)- 1,3,5-triazine; di-n-octadecyl 3,5-di-tert-butyl-4- hydroxybenzyl-phosphorate; 2-(n-octt
  • An especially preferred anti-oxidant is pentaerythritol tetrakis-3-(3,5-di-tertiarybutyl-4- hydroxyphenyl)propionate which is available from Ciba-Geigy under the tradename Irganox 1010. (Hawthorne, New York)
  • any other compatible anti-oxidant or combination of anti-oxidants may be used without departing from the scope of the invention.
  • the adhesive composition of the present invention may optionally include one or more compatible tackifying resins.
  • the decision to employ a tackifying resin is application dependent.
  • the tackifying resin functions either to impart rigidity or as a diluent to lower the adhesives cost.
  • Suitable tackifying resins include wood rosin, gum rosin, tall oil rosin, and the acidic resins such as those produced by the hydrogenation of wood rosin.
  • a preferred tackifying resin is the acidic resin that is produced by hydrogenating wood rosin to an exceptionally high degree and which is commercially available from Hercules, Inc. (Wilmington DE) under the tradename FORAL ® AX. This tackifying resin has a softening point of 74 °C (Hercules drop method), an acid number of
  • a preferred water dispersible adhesive composition of the present invention comprises:
  • the adhesive composition of the present invention further includes up to about 15% by weight of one or more compatible tackifiers.
  • the present invention is also directed to an improved perfect bound book.
  • the conventional perfect bound book comprises one or more signatures, a cover, and an animal glue or hot melt adhesive for binding the cover to the signatures.
  • the improvement comprises employing the water dispersible hot melt adhesive of the present invention for binding a cover to one or more signatures to produce a perfect bound book that cannot only utilize high quality stock with coatings but which is ultimately repulpable.
  • Sample No. 1 which was prepared according to the procedure of Example 1 infra, represents an embodiment of the present invention.
  • Example #1 gave excellent adhesion both to enamel stock signatures and to solid ink and varnished covers. Moreover, it exhibited a viscosity and setting speed very similar to a traditional non-dispersible book binding adhesive. This allows it to be run on binders interchangeably with EVA and rubber-based hot melts.
  • Sample #1 was also compared to a hot melt adhesive of the water insoluble type in terms of tensile strength, elongation and yield point. (Table 1).
  • Table 1 shows that the adhesive of the present invention has tensile strength and elongation values similar to a commercially available hot melt adhesive of the water insoluble type.
  • sample #1 was also compared to a water soluble animal glue for both page pull value and page flex values.
  • Sample #1 was tested on a 1/2 inch thick phone book that had 60 lb. enamel inserts.
  • the cover stock was printed with solid red-ink and had a lacquer coating over the ink.
  • Books were bound at 3500 bph on a Sheridan XP binder.
  • the adhesive temperature was 350°F.
  • the books were evaluated in terms of their page pull values, page flex values, and humidity resistance. The page pulls and flexes were evaluated on a J.E. Plunket page flex tester.
  • the adhesive of the present invention has superior page pull values when compared to animal glues.
  • the adhesive of the present invention has the advantage of giving good page pull and flex values using enamel coated papers to which animal glue does not effectively adhere.
  • Table 3 the 1/2 inch book that had been bound with
  • Sample #1 (1/2" Sample #1) was compared to the 1/2 inch book that had been bound with animal glue ("1/2" Animal
  • Glue for "humidity resistance.”
  • the above books were aged for 72 hrs at 77 °F and 79% relative humidity in a closed container that had a saturated NH 4 H solution in the bottom in order to treat their humidity resistance.
  • the adhesive composition of the present invention is capable of being made resistant to page loss due to page pull when exposed to high humidity at high temperatures.
  • the adhesive composition employs a hydrophobic plasticizer as at least one of the plasticizers in the composition.
  • the hydrophobic plasticizer comprises from about 2% to about 10% by weight of the adhesive composition; more preferably, from about 4% to about 6% by weight of the composition.
  • An especially preferred hydrophobic plasticizer is Santicizer 160.
  • a preferred water dispersible adhesive composition that exhibits increased resistance to page loss at high humidity comprises:
  • the adhesive composition further contain from about 6% to about 14% by weight of a second polyester having a molecular weight of less than 10,000 daltons, particularly where greater humidity resistance is required.
  • a particularly preferred polyester is available from Hiils Aktiengesellschaft as Dynacoll® 7340, a partially crystalline copolyester having a molecular weight of approximately 3500, a hydroxyl number of from about 27 -34, and an acid number of ⁇ 2.
  • a particularly preferred water dispersible adhesive composition that has increased humidity resistance was prepared as in Example 2 and has the overall composition noted in Sample #4.
  • the adhesive compositions of Examples 1 and 2 were compared to determine their resistance to humidity when used in telephone directories that were subject to hanging by their bindings.
  • a first set consisting of two identical telephone directories was "perfect bound” with the water dispersible adhesive composition of Example 1.
  • a second set consisting of two identical telephone directories was perfect bound with water dispersible adhesive composition of Example 2, which had hydrophobic plasticizer.
  • the four directories were then subjected to extreme heat and humidity conditions. Specifically, all four directories were supported in a hanging position by a rod running lengthwise through the middle of each book. The support simulated how telephone directories are sometimes held in public phone booths, wherein the constant downward pull on the pages by gravity tests the overall strength of the adhesive used in the binding.
  • the four directories on the rods were enclosed in a chamber in which both the temperature and the humidity were controlled.
  • the four supported books were first subjected to a temperature of 120 °F at 30% relative humidity. After twenty-four hours, one of the books (book #1) that was perfect bound with the adhesive composition of Example 1 lost approximately 50% of its pages. Thereafter, the relative humidity in the chamber was increased to 40% while the temperature was maintained at 120°F. After 4.5 hours at 40% relative humidity, book #1 lost 100% of its pages; a second book (book #2) of the first set lost approximately 50% of its pages. After twenty-three hours at 40% relative humidity and 120°F, book #2 lost 100% of its pages. Only the two books of the second set that were prepared with the adhesive composition of Example 2 remained intact.
  • Example 2 It is not possible for a water dispersible hot melt adhesive composition to be completely unaffected by extremes of humidity and temperature, otherwise it would not be water dispersible. However, the water dispersible adhesive composition of Example 2 exhibits significant resistance to loss of adhesion even in heat and humidity extremes such as might be found for short duration in the environment (e.g., 120°F at 40% relative humidity), and even when subject to constant stress for days such as the downward pull of gravity.
  • the water dispersible adhesive composition of the present invention encompasses embodiments, such as Example 1, which is suitable for use in most situations wherein constant stress and high humidity are not factors to embodiments such as Example 2, which is suitable for use in most situations including those wherein constant stress and high humidity are indeed significant factors.
  • 300°-350°F. was added 1.08 parts per 100 by weight (hereinafter "parts") of polyethylene glycol 300 (PEG 300), 7.62 parts of polyethylene glycol 400 (PEG 400), and 0.45 parts of Irganox 1010. While maintaining the temperature at from about 300°-350°F., 25 parts of Eastman AQ29S was added with mixing until the mixture became smooth. When smooth, another 25 parts of Eastman AQ29S was added with mixing until smooth. The step was repeated again. Finally, 3.25 parts of Eastman AQ29S was added to the heated (300°-350°F.) reaction mixture with stirring until smooth.
  • the resultant water dispersible hot melt adhesive was prepared for application by reheating to between 300°375°F. To preclude degradation, the adhesive should not be maintained at this temperature for longer than 24 hours.

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

Abstract

La présente invention se rapporte à la fois à une composition adhésive thermofusible dispersible dans l'eau et à des livres recyclables dont la reliure utilise la colle dispersible dans l'eau de cette invention. La composition adhésive comprend: (a) d'environ 40 % à 95 % en poids d'une résine de polyester à substitution ionique et dispersible dans l'eau, présentant un poids moléculaire d'environ 10 000 à 20 000 daltons; (b) d'environ 60 % à environ 5 % en poids d'un ou plusieurs plastifiant(s) compatible(s); et (c) d'environ 0,1 % à environ 1,5 % d'un ou plusieurs stabilisateur(s) compatible(s), du type anti-oxydant. Eventuellement, la composition adhésive peut en outre comprendre un ou plusieurs agent(s) d'adhérence compatible(s) en une proportion totale atteignant jusqu'à 30 % en poids de la composition adhésive.
PCT/GB1991/001006 1990-06-25 1991-06-21 Application et composition adhesive thermofusible dispersible dans l'eau WO1992000363A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US54258090A 1990-06-25 1990-06-25
US542,580 1990-06-25

Publications (1)

Publication Number Publication Date
WO1992000363A1 true WO1992000363A1 (fr) 1992-01-09

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PCT/GB1991/001006 WO1992000363A1 (fr) 1990-06-25 1991-06-21 Application et composition adhesive thermofusible dispersible dans l'eau

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AU (1) AU8064891A (fr)
WO (1) WO1992000363A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995018191A1 (fr) * 1993-12-29 1995-07-06 Eastman Chemical Company Composition d'adhesif dispersible dans l'eau et son procede de fabrication
EP0761795A3 (fr) * 1995-08-31 1997-10-22 Nat Starch Chem Invest Adhésifs thermofusibles à base de polyesters sulfonés
EP0781538A3 (fr) * 1995-11-22 1997-11-05 H.B. Fuller Licensing & Financing, Inc. Application de copolyester dispersable dans l'eau sur un matériau non-tissé

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3779993A (en) * 1970-02-27 1973-12-18 Eastman Kodak Co Polyesters and polyesteramides containing ether groups and sulfonate groups in the form of a metallic salt
US3891584A (en) * 1974-02-22 1975-06-24 Nat Starch Chem Corp Water-dispersible hot melt adhesives and products using same
US4052368A (en) * 1976-06-21 1977-10-04 Minnesota Mining And Manufacturing Company Water-dispellable hot melt polyester adhesives
US4540749A (en) * 1984-08-09 1985-09-10 Eastman Kodak Company Adhesive blends
US4598142A (en) * 1985-04-29 1986-07-01 Eastman Kodak Company Copolyester adhesives

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3779993A (en) * 1970-02-27 1973-12-18 Eastman Kodak Co Polyesters and polyesteramides containing ether groups and sulfonate groups in the form of a metallic salt
US3891584A (en) * 1974-02-22 1975-06-24 Nat Starch Chem Corp Water-dispersible hot melt adhesives and products using same
US4052368A (en) * 1976-06-21 1977-10-04 Minnesota Mining And Manufacturing Company Water-dispellable hot melt polyester adhesives
US4540749A (en) * 1984-08-09 1985-09-10 Eastman Kodak Company Adhesive blends
US4598142A (en) * 1985-04-29 1986-07-01 Eastman Kodak Company Copolyester adhesives

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Japan Plastics Age , vol. 11, no. 10, October 1973, H. Kuroki:"Hot melts and their applications. Part II hot-melt adhesives - their manufacturing processes and physical properties", pages 53-60, see page 54, chapter 1-1-2; pages 55-56, chapter 1-1-5,1-1-6,1-2-1 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995018191A1 (fr) * 1993-12-29 1995-07-06 Eastman Chemical Company Composition d'adhesif dispersible dans l'eau et son procede de fabrication
AU680094B2 (en) * 1993-12-29 1997-07-17 Eastman Chemical Company Water-dispersible adhesive composition and process
EP0761795A3 (fr) * 1995-08-31 1997-10-22 Nat Starch Chem Invest Adhésifs thermofusibles à base de polyesters sulfonés
AU702877B2 (en) * 1995-08-31 1999-03-11 National Starch And Chemical Investment Holding Corporation Hot melt adhesives based on sulfonated polyesters
US6087550A (en) * 1995-11-09 2000-07-11 H. B. Fuller Licensing & Financing, Inc. Non-woven application for water dispersable copolyester
EP0781538A3 (fr) * 1995-11-22 1997-11-05 H.B. Fuller Licensing & Financing, Inc. Application de copolyester dispersable dans l'eau sur un matériau non-tissé
EP1857518A3 (fr) * 1995-11-22 2007-12-26 H.B. FULLER LICENSING & FINANCING, INC. Adhésif thermofusible dispersable dans l'eau

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Publication number Publication date
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