GB2303370A - Bonding and coating composition - Google Patents
Bonding and coating composition Download PDFInfo
- Publication number
- GB2303370A GB2303370A GB9514781A GB9514781A GB2303370A GB 2303370 A GB2303370 A GB 2303370A GB 9514781 A GB9514781 A GB 9514781A GB 9514781 A GB9514781 A GB 9514781A GB 2303370 A GB2303370 A GB 2303370A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pack according
- aii
- component
- components
- composition
- 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.)
- Granted
Links
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H19/00—Coated paper; Coating material
- D21H19/36—Coatings with pigments
- D21H19/44—Coatings with pigments characterised by the other ingredients, e.g. the binder or dispersing agent
- D21H19/56—Macromolecular organic compounds or oligomers thereof obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D21H19/58—Polymers or oligomers of diolefins, aromatic vinyl monomers or unsaturated acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L29/00—Compositions of 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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical; Compositions of hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Compositions of derivatives of such polymers
- C08L29/02—Homopolymers or copolymers of unsaturated alcohols
- C08L29/04—Polyvinyl alcohol; Partially hydrolysed homopolymers or copolymers of esters of unsaturated alcohols with saturated carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D129/00—Coating compositions 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 an alcohol, ether, aldehydo, ketonic, acetal, or ketal radical; Coating compositions based on hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Coating compositions based on derivatives of such polymers
- C09D129/02—Homopolymers or copolymers of unsaturated alcohols
- C09D129/04—Polyvinyl alcohol; Partially hydrolysed homopolymers or copolymers of esters of unsaturated alcohols with saturated carboxylic acids
-
- 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
- C09J129/00—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 an alcohol, ether, aldehydo, ketonic, acetal, or ketal radical; Adhesives based on hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Adhesives based on derivatives of such polymers
- C09J129/02—Homopolymers or copolymers of unsaturated alcohols
- C09J129/04—Polyvinyl alcohol; Partially hydrolysed homopolymers or copolymers of esters of unsaturated alcohols with saturated carboxylic acids
-
- 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
- C08L2666/04—Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; 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
- C08L2666/28—Non-macromolecular organic substances
Description
COMPOSITION
The present invention relates to compositions which are especially suitable for use in the paper and woodworking and related fields. The present compositions find particular, but not exclusive use, as adhesives, binding, coating and sealing materials.
Many adhesives currently available, particularly for use in woodworking, contain polyvinyl alcohol (PVOH) or a dispersion of another polymer such as polyvinyl acetate in polyvinyl alcohol (PVAc) (PVOH). The adhesives operate by forming a physical bond with the wood substrate. In this respect the -OH groups in the'adhesive composition and the -OH groups from cellulose in the wood substrate together form strong hydrogen bonds. Problems arise with such adhesives in that they exhibit poor water resistance.
This limits the number of potential uses for such adhesives. The inherent moisture content of the wood substrate can also cause difficulties for such adhesives.
Also, many existing products in use in the woodworking field require metal salt catalysts in their crosslinking or curing reaction such as aluminium chloride and chromium nitrate, for example. Use of such metal salts has disadvantages in terms of safety for both manufacturing and handling of the adhesive. Also, many of the formulations presently available have a low pH value (approximately 3) which can give rise to discoloration of wood which contains tanin.
The present invention seeks to alleviate at least some of the aforementioned problems.
With this aim in mind, in one aspect the present invention concerns a two part pack including components A and B, wherein
Component A contains Ai)a solution or dispersion which includes a polymer containing units having hydroxyl groups; and
Aii) a polymer containing units having carboxyl groups; and wherein Component B comprises
Bi)a crosslinker, preferably comprising a polyfunctional aziridine, the crosslinker being capable of crosslinking with at least one carboxyl group and at least one hydroxyl group.
In this aspect of the invention, suitably both components A and B are in liquid form. In preferred embodiments the pack includes a first openable compartment containing both components Ai) and Aii) and a second openable compartment containing component Bi).
In another aspect the present invention provides a composition obtainable by crosslinking Ai) a polymer containing hydroxyl units and Aii) a polymer containing units having carboxyl groups with Bi) a polyfunctional crosslinker which is capable of crosslinking with hydroxyl groups and with carboxyl groups.
In another aspect the present invention also relates to use of a composition obtainable by crosslinking Ai)a polymer containing hydroxyl units and Aii) a polymer containing units having carboxyl groups, with Bi), a polyfunctional crosslinker as a protective coating, especially for products derived from or containing cellulose, including paper and wood products.
A yet further aspect of the present invention concerns use-of a composition obtainable by crosslinking
Ai) a polymer containing hydroxyl units; and Aii)a polymer containing units having carboxyl groups; with Bi) a polyfunctional crosslinker as an adhesive, especially for wood products and other products derived from or containing cellulose.
Other aspects of the present invention concern methods of providing protective coatings especially =or wood and paper products and methods for adhering surfaces of wood and paper products to other substrates.
Preferably the methods of coating include applying the present compositions in the form of a spray. Suitably the method of adhering substrates involves applying the compositions to one substrate using brushes, rollers etc.
In some preferred embodiments Component Ai) is in the form of an aqueous solution of polyvinyl alcohol. The polyvinyl alcohol may be selected from both low and high molecular weight polymers. Also, polyvinyl alcchols of various degrees of hydrolysis may be employed. The appropriate choice of polyvinyl alcohol will depend upon the desired characteristics of the composition, for example the desired viscosity.
In other preferred embodiments component Ai) is an aqueous dispersion of a polymer which includes polyvinylalcohol as a stabiliser. Preferably any such polymers include units having acetate groups which are popular for use in the woodworking field, but many other types of polymer are suitable. Preferred polymers containing units having acetate groups include polyvinyl acetate homopolymers or copolymers, most preferably as a dispersion with polyvinyl alcohol. Other example polymers as component Ai) include ethylene vinyl acetate copolymers and terpolymer dispersions. Preferably any component Ai) is water miscible. It is also preferred that the polymer has a viscosity of between about 20,000 and 80,000 mPas when measured at 23"C. Preferably any such dispersion has a solids content of from about 35% to about 65%.Any such polymers which include units having acetate groups may be used alone or in combination. Polymers containing ethylene vinyl acetate units may be preferred in some circumstances as they may produce films which are harder than those obtainable with ethylene vinyl acetate.
Preferably the component Aii) comprises a polymer derived from at least one ethylenically unsaturated monomer. It is also preferred that Aii) comprises a polymer derived from styrene units. Most preferably Aii) comprises a carboxylated styrene butadiene rubber latex.
It is also preferred that any component Aii) be water miscible. Preferably the component has a solids content of from about 30t to about 70%.
In addition to Ai) and Aii), component A may optionally additionally include filler materials. Any such filler materials are desirable for improving water resistance. Example fillers include talc, silica, kaolin or calcium carbonate. Preferably, one or more such fillers are provided in fine powder form or as a suspension in water.
The amount of any filler employed may be varied in accordance with the desired end properties of the composition. The fillers may prevent excessive penetration of the composition into the substrate. They may also impart better water resistance and film hardness to the final adhesive/coating. Suitably component A includes no more than about 70 weight g filler(s).
Preferably the component A includes up to about 50 weight % filler, preferably from about 1% to about 50%, most preferably between 30 and 45%. Component A may also additionally include agents to ease its storage and handling, as are common in this field. Component A may also include other agents for modifying the properties of the crosslinked film product. Optional additional agents/ingredients include thickening agents (e.g. a polyacrylic or cellulose thickener such as methyl cellulose or hydroxyl ethyl cellulose, aromatic solvents, and plasticisers (e.g. dibutyl phthalate or butyl benzyl phthalate) to improve flexibility of the final polymer film.
Various weight ratios of components Ai) and Aii) may be employed, depending upon the desired characteristics of the composition. Preferably the ratio of Ai) to Aii) ranges from about 1:10 to about 10:1. Most preferably, component A includes approximately equal weight quantities of Ai) and Aii). If the relative amount of Ai) is increased beyond this level, this results in a decrease in the water and heat resistance of the subsequent composition. On the other hand, if the level of component
Aii) is increased this results in a reduction in the bonding strength of the subsequent composition.
In the various aspects of the present invention the polyfunctional crosslinker is one which is capable of crosslinking with a hydroxyl group from component Ai) and a carboxyl group from component Aii)
Preferably the crosslinker Bi comprises a polyfunctional aziridine crosslinker. It is especially preferred that the aziridine crosslinker is trifunctional and most preferably it has the following formula:
wherein Y is a lower alkyl group of from 1 to about 4 carbon atoms. Preferably Y is a methyl group. R is a polymer chain. A particularly preferred polyfunctional aziridine crosslinker in which Y is methyl is commercially available. The crosslinker is designated CAS number 64265-57-2.
Whereas polyfunctional aziridine crosslinkers are most preferred, other crosslinkers which are capable of crosslinking with at least one carboxyl group and at least one hydroxyl group may be employed. Other example crosslinkers include melamine resin.
Suitably the component B is added at a level of no more than about 10 weight % to component A, preferably at the level of between about 1 to 5 weight % component A.
Most preferably the crosslinker is water miscible.
An aqueous dispersion of the crosslinker may be stabilised with the aid of solvents such as methylglycol acetate and glycol solvents, for example.
Such a trifunctional aziridine crosslinker may crosslink components Ai) and Aii) and the wood substrate as follows:
Reaction with carboxyl group in Aii)
Reaction with hydroxyl group in Ai) and wood substrate
Suitable aziridine crosslinkers are capable of reacting with a carboxyl group at normal room temperature. As a result the present compositions and packs are capable of producing an adhesive effect, or of forming a protective coating, at room temperature.
In preferred embodiments of the invention, appropriate choice of components Ai), Aii) and B may provide an adhesive or coating composition, for example, which is employable at room temperature without the need for additional catalysts as required in prior formulations.
The combination of components A and B in accordance with the present invention gives rise to compositions having improved adhesion and water resistance as compared to products currently available. The prime and preferred application for the present invention is the wood working industries, for example wood bonding, formation of particle board by binding woodchips and wood coating to improve abrasion, chemical and water resistance. However the present invention is also applicable to paper industries, particularly for coating paper to improve water resistance and stiffness. This may be useful in the production of- paper cartons.
In this regard, another aspect of the present invention relates to a particle board obtainable by bonding woodchips with a composition comprising components
Ai), Aii) and Bi) as defined above.
Suitably, an aziridine crosslinker as component Bi) has a pH of between about 10 and 11, especially about 10.5. Typically component Ai) has a pH of about 4 to 5.
Preferably component Aii) is selected so as to have a pH of between about 7.5 to 9.5. In this respect, a composition comprising components Ai), Aii) and Bi) will typically have a pH which is higher than the pH-3 value of prior art compositions. Embodiments of the present invention provide compositions having a pH of between about 6.5 to 8.5, especially approximately 7/8. This has advantages in reducing the possibility of causing discoloration of wood containing tanin.
As discussed above, suitably components Ai), Aii) and
B are selected so as to be water miscible. Thus, the present invention also has advantages in providing a cost effective water borne system, which may be free of undesirable solvents such as formaldehyde and phenol. In this regard the present invention has advantages over prior art compositions.
Embodiments of the present invention will now be described further, by way of example, with reference to the accompanying examples:
Example
A first example formulation was prepared as follows:
Component Parts by
weight
Ai) Homopolymer Polyvinyl Acetate
Dispersion (PVOH)
(Solid content approx. 60%) 30 p.b.w.
Aii) Carboxylated Styrene Butadiene
Latex Dispersion
(S.C. approx 46-52t) 30 p.b.w.
Aiii)Filler - Paste form
(Calcium carbonate powder 60-70% in water) 40 p.b.w.
In can preservative 0.5
A pack contains two compartments, one accommodating Part A and the other accommodating Part B.
Part A is a blend of the above preferred components Ai) to Aiii). Part B (crosslinker) is preferably in an amount of added 3 p.b.w to the compounded dispersion (Part A) before use. In this example B is of Formula I wherein Y is methyl.
The properties of the first example formulation were determined and compared with those of an existing adhesive which is commercially available. The test results are shown below.
Test Results
Example 1 Commercially
available
adhesive
Crosslinker Polyfunctional aziridine Metal salt
catalyst
Bonding Chemical Bond Physical bond effect
Water Reasonable Reasonable resistance
Solvent Reasonable Poor resistancy
Abrasion Reasonable Poor resistance pH Approx. 7-8 Approx. 3
-low discoloration effect high
discoloration
effect
Setting speed Fast - readily adjustable Moderate
difficult to
adjust.
Ageing time* Fast - less than 3 hours Slow - at
least 6 hours *Ageing relates to the time for which the substrates are left to stand at room temperature after pressing to enable them to be suitable for processing such as by sawing or sanding.
All the proportions in this Example I formulation can be varied subject to the desired end application and cost.
However, the above formulation stated has been developed to provide a desirable balance in the end properties such as adhesion, cohesion and film hardness.
It will be appreciated that the Example 1 formulation included equal amounts of components Ai) and Aii). The following Examples 2 and 3 illustrate the effect of varying the weight ratios of the two components on the final properties of the crosslinked product. The components Ai), Aii) and Bi) are the same as those employed above; only the weight ratios have been varied.
Example 2 Component Parts by weight
Ai) PVAc Homopolymer (PVOH) dispersion 54
Aii) XSBR 6
Aiii) Filler paste 40
B: as Example 1
Example 3
Ai) PVAc Homopolymer (PVOH)dispersion 6
Aii) XSBR 54
Aiii)Filler paste 40
B: as Example 1
Packs were prepared containing a first vessel of components Ai) to Aiii) and a second vessel containing solely component B.
In comparison to the formulation of Example I, the
Example 2 formulation exhibited a lower bonding strength and lower water and heat resistance. Also, in comparison to the Example 1 formulation, the product of Example 3 was very low in viscosity and thus was more difficult to apply to the wood substrate. It also gave rise to various levels of bonding strengths depending upon the nature of the wood substrate. It did, however, exhibit good water and heat resistance.
The above examples illustrate the effects of varying the levels of the respective components in the present packs and compositions. Various modifications may be made to the above Examples.
Claims (27)
1. A pack containing components A and B, wherein:
component A contains Ai) a solution or dispersion comprising a polymer containing units having hydroxyl groups, and
Aii) a polymer containing units having carboxyl groups;
component B comprises Bi) a polyfunctional crosslinker capable of crosslinking with at least one carboxyl group and at least one hydroxyl group.
2. A pack according to claim 1 wherein Ai) is a solution of polyvinyl alcohol.
3. A pack according to claim 1 wherein Ai) is a dispersion which contains polyvinyl alcohol.
4. A pack according to claim 3 wherein Ai) is a dispersion which includes a polyvinyl acetate homopolymer or copolymer.
5. A pack according to claim 3 or claim 4 wherein Ai) includes an ethylenevinylacetate copolymer or terpolymer.
6. A pack according to any preceding claim wherein Aii) comprises a polymer derived from at least one ethylenically unsaturated monomer.
7. A pack according to claim 6 wherein Aii) comprises a polymer derived from an optionally substituted styrene monomer.
8. A pack according to claim 6 or claim 7 wherein Aii) comprises a carboxylated styrene butadiene rubber latex.
9. A pack according to any preceding claim wherein component A contains Ai) and Aii) in a weight ratio of between 1-.10 and 10:1.
10. A pack according to claim 9 wherein component A contains Ai) and Aii) in a weight ratio of between 1:5 and 5:1.
11. A pack according to claim 10 wherein component A contains Ai) and Aii) in a weight ratio of approximately 1:1.
12. A pack according to any preceding claim wherein component A additionally contains Aiii) one or more fillers, and/or
Aiv) one or more preservatives.
13. A pack according to any preceding claim wherein component B comprises Bi) a polyfunctional aziridine crosslinker.
14. A pack according to claim 13 wherein component B comprises Bi) a trifunctional aziridine crosslinker of formula I
wherein R is a polymer chain and Y is a lower alkyl group of from 1 to 4 carbon atoms.
15. A pack according to claim 14 wherein Bi) is a trifunctional aziridine crosslinker in which Y is methyl.
16. A pack according to any preceding claim wherein Bi) is water miscible.
17. A pack according to any preceding claim wherein Ai) and Aii) are water miscible.
18. A pack according to any preceding claim wherein components A and B are provided in a weight ratio of from 100 to 10 to 100 to 0.1.
19. A pack according to claim 18 wherein components A and
B are provided in a weight ratio of from 100 to 5 and 100 to 0.1.
20. A pack substantially as hereinbefore described with reference to the accompanying Examples.
21. A composition obtainable by crosslinking components
Ai) and Aii) as defined in any one of claims 1 to 11 with a component Bi) as defined in any one of claims 13 to 16.
22. Use of a composition according to claim 21 as a protective coating for substrates derived from or containing cellulose.
23. Use of a composition according to claim 22 as an adhesive for substrates derived from or containing cellulose.
24. A method of adhering a first cellulosic substrate to a second substrate which method comprises combining components A and B as defined in any one of claims 1 to 17 to provide an adhesive combination, applying the combination to the first substrate, and bringing the first and second substrates together in the region of applied adhesive combination.
25. A method of protecting a cellulosic substrate, which method comprises combining components A and B as defined in any one of claims 1 to 17 and applying the combination to the substrate to provide a protective coating.
26. A particleboard obtainable by adhering woodchips together with a composition comprising a mixture of components A and B as defined in any one of claims 1 to 17.
27. A wood product obtainable by adhering wood substrates together with a composition comprising a mixture of components A and B as defined in any one of claims 1 to 17.
Priority Applications (16)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/SG1996/000002 WO1996037551A1 (en) | 1995-05-26 | 1996-04-09 | Two-component polymer composition |
EP96914538A EP0828790A1 (en) | 1995-05-26 | 1996-04-09 | Two-component polymer composition |
US08/952,906 US5880183A (en) | 1995-05-26 | 1996-04-09 | Two-component polymer composition |
CN96194201A CN1097612C (en) | 1995-05-26 | 1996-04-09 | Two-component polymer composition |
NZ308278A NZ308278A (en) | 1995-05-26 | 1996-04-09 | Two-component polymer composition |
KR1019970708470A KR19990021995A (en) | 1995-07-19 | 1996-04-09 | Two-Component Polymer Composition |
CA002222295A CA2222295A1 (en) | 1995-05-26 | 1996-04-09 | Two-component polymer composition |
AU57867/96A AU695833B2 (en) | 1995-05-26 | 1996-04-09 | Two-component polymer composition |
RO97-02171A RO114899B1 (en) | 1995-05-26 | 1996-04-09 | Polymer composition |
CZ973644A CZ364497A3 (en) | 1995-05-26 | 1996-04-09 | Two-component polymer composition |
AT0903396A ATA903396A (en) | 1995-05-26 | 1996-04-09 | TWO COMPONENT POLYMER COMPOSITION |
HU9801994A HUP9801994A3 (en) | 1995-05-26 | 1996-04-09 | Two-component polymer composition |
BR9609191A BR9609191A (en) | 1995-05-26 | 1996-04-09 | Package composition processes for adhering a first cellulosic substrate to a second substrate to protect a cellulosic substrate and wood product |
MYPI96001595A MY118277A (en) | 1995-05-26 | 1996-04-26 | Two-component polymer composition |
NO975422A NO975422L (en) | 1995-05-26 | 1997-11-25 | Two-component polymer blend |
MXPA/A/1997/009137A MXPA97009137A (en) | 1995-05-26 | 1997-11-26 | Polymeric composition of two components |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SG1995000525A SG45099A1 (en) | 1995-05-26 | 1995-05-26 | Composition |
Publications (3)
Publication Number | Publication Date |
---|---|
GB9514781D0 GB9514781D0 (en) | 1995-09-20 |
GB2303370A true GB2303370A (en) | 1997-02-19 |
GB2303370B GB2303370B (en) | 2000-01-19 |
Family
ID=20429070
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB9514781A Expired - Fee Related GB2303370B (en) | 1995-05-26 | 1995-07-19 | Bonding and coating composition |
Country Status (4)
Country | Link |
---|---|
GB (1) | GB2303370B (en) |
MY (1) | MY118277A (en) |
SG (1) | SG45099A1 (en) |
ZA (1) | ZA963191B (en) |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1423558A (en) * | 1972-08-05 | 1976-02-04 | Kuraray Co Ltd Asahi Co Ltd | Adhesive composition |
GB1424041A (en) * | 1972-07-07 | 1976-02-04 | Bayer Ag | Rubber compositions |
US4588772A (en) * | 1983-11-04 | 1986-05-13 | Wolff Walsrode Ag | Water-soluble, polymer-modified hydroxyalkyl methyl cellulose and its use as an additive for asbestos-free tile adhesive formulations |
JPS6426689A (en) * | 1987-07-23 | 1989-01-27 | Showa Highpolymer | Aqueous adhesive composition with good adhesivity and heat resistance |
EP0413136A2 (en) * | 1989-07-14 | 1991-02-20 | Kuraray Co., Ltd. | Polymer composition, adhesive and labelled glass material |
-
1995
- 1995-05-26 SG SG1995000525A patent/SG45099A1/en unknown
- 1995-07-19 GB GB9514781A patent/GB2303370B/en not_active Expired - Fee Related
-
1996
- 1996-04-22 ZA ZA963191A patent/ZA963191B/en unknown
- 1996-04-26 MY MYPI96001595A patent/MY118277A/en unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1424041A (en) * | 1972-07-07 | 1976-02-04 | Bayer Ag | Rubber compositions |
GB1423558A (en) * | 1972-08-05 | 1976-02-04 | Kuraray Co Ltd Asahi Co Ltd | Adhesive composition |
US4588772A (en) * | 1983-11-04 | 1986-05-13 | Wolff Walsrode Ag | Water-soluble, polymer-modified hydroxyalkyl methyl cellulose and its use as an additive for asbestos-free tile adhesive formulations |
JPS6426689A (en) * | 1987-07-23 | 1989-01-27 | Showa Highpolymer | Aqueous adhesive composition with good adhesivity and heat resistance |
EP0413136A2 (en) * | 1989-07-14 | 1991-02-20 | Kuraray Co., Ltd. | Polymer composition, adhesive and labelled glass material |
Non-Patent Citations (1)
Title |
---|
WPI Abstract Accession No 89-073472/10 & JP 01 026 689 A * |
Also Published As
Publication number | Publication date |
---|---|
MY118277A (en) | 2004-09-30 |
ZA963191B (en) | 1996-10-25 |
GB2303370B (en) | 2000-01-19 |
GB9514781D0 (en) | 1995-09-20 |
SG45099A1 (en) | 1998-01-16 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 20000419 |