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WO1996008538A1 - Polyamides utilises en tant qu'adhesifs rehumectables - Google Patents

Polyamides utilises en tant qu'adhesifs rehumectables Download PDF

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Publication number
WO1996008538A1
WO1996008538A1 PCT/US1995/000124 US9500124W WO9608538A1 WO 1996008538 A1 WO1996008538 A1 WO 1996008538A1 US 9500124 W US9500124 W US 9500124W WO 9608538 A1 WO9608538 A1 WO 9608538A1
Authority
WO
WIPO (PCT)
Prior art keywords
acid
envelope
remoistenable adhesive
sticker
stamp
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/US1995/000124
Other languages
English (en)
Inventor
Sharf U. Ahmed
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.)
HB Fuller Licensing and Financing Inc
Original Assignee
HB Fuller Licensing and Financing Inc
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 HB Fuller Licensing and Financing Inc filed Critical HB Fuller Licensing and Financing Inc
Priority to EP95907982A priority Critical patent/EP0788531A4/fr
Priority to AU15983/95A priority patent/AU691871B2/en
Priority to NZ279381A priority patent/NZ279381A/en
Priority to JP8510150A priority patent/JPH10507783A/ja
Publication of WO1996008538A1 publication Critical patent/WO1996008538A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C09J177/00—Adhesives based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Adhesives based on derivatives of such polymers
    • C09J177/06—Polyamides derived from polyamines and polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/40—Polyamides containing oxygen in the form of ether groups
    • 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
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • C09J7/21—Paper; Textile fabrics
    • 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
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition

Definitions

  • the present invention pertains to remoistenable hot melt adhesives, and their application to envelopes, stamps, packaging tape or stickers and labels.
  • an adhesive composition must be activatable by moistening with water.
  • the adhesive composition is a bonding agent which may be applied to one surface utilizing a hot melt technique and another surface using a water-moistening technique, so that the two surfaces are bonded together by means of composition.
  • a composition may be applied by the hot melt technique as gumming for stickers and labels, stamps, packaging tapes and envelope flaps at a point of manufacture where the intricate equipment required for hot melt application is available, the stickers and labels, stamps, packaging tapes and envelope flaps, ultimately being applied by the consumer to other surfaces using the much simpler water-moistening technique, e.g. by moistening the adhesive coating prior to application to the other surface.
  • the hot melt application is utilized where the required equipment is available because it is a rapid and economical technique, the water-moistening technique is utilized precisely because it doesn't require such elaborate equipment.
  • remoistenable adhesives are valued because of their superior process speed, and their streamlining of process equipment by elimination of driers and other auxiliary equipment or the like.
  • composition has been hot-melt applied to a substrate, it must be able to resist elevated temperature conditions likely to be found in its environment without again becoming tackified or undergoing other undesirable changes, such as discoloration (darkening), over a prolonged period of time. Similarly, it must be able to withstand the various humid conditions likely to be found in its environment without becoming tacky until it is actually moistened immediately prior to use.
  • Remoistenable water soluble polymers other than polyamides appear to be deliquescent, that is they tend to undergo gradual dissolution and liquefaction by the attraction and absorption of moisture from the air, causing them to block at high humidity and temperature. This can cause a serious problem during storage of products utilizing remoistenable adhesives. Blocking can be characterized as any degree of adhesive between touching layers of similar or dissimilar material, such as occurs under moderate pressures during storage or use. To achieve desired properties prior art polymers require wax and tackifiers to prevent blocking and to promote stability. The end result is that remoistenable adhesive products that suffer from blocking are rendered useless when they prematurely seal.
  • Water soluble polymers like poly vinyl alcohol, PeOX, and PVP are known in literature for their compounding ability to form adhesives for remoistening application. These hot melt adhesives provide several advantages for the envelope and packaging industries and other related industries, including a very fast rate of application, the ability to heat seal when remoistening is not required, and the fact that the water solubility of the adhesive will make the products recyclable.
  • these water soluble polymers require water soluble/insoluble tackifiers and waxes to achieve the desired remoistening properties. Because of the nature of the polymers and the use of tackifiers and waxes the adhesives are rendered with low blocking resistance and low thermal stability.
  • Flanagan, U.S. 4,623,688 discloses remoistenable hot melts adhesives which are prepared from poly(alkyloxazoline) (having the general formula C 3 H 4 NO), a diluent and, optionally, a tackifier, plasticizer and non-block additive. Like other known remoistenable adhesives, in order to achieve preferred non- blocking, heat and humidity resistance, and bond strength properties certain materials are added, such as tackifiers, plasticizers, stabilizers and non-block additives.
  • U.S. patents 4,623,688; 5,053,484; 4,133,803; 5,086,162 all teach the synthesis of water soluble polyamides. Poly amides have been produced for many reasons, but not for use as a remoistenable adhesive.
  • Klein, U.S. 4,133,803 discloses polyoxypropylene polyamine polyamide thermoplastic adhesives. It pertains to a novel thermoplastic adhesive comprised of a polyamide product, and can be prepared from relatively inexpensive and readily available synthetic materials. This invention was driven by the need for satisfactory replacements for naturally derived materials. It eliminated the need for employing vegetable or animal-based dimer or trimer fatty acids which are usually in short supply, but did not disclose the use of the polyamides as a remoistenable adhesive.
  • the invention is directed to remoistenable hot melt adhesives which are the product of a dicarboxylic acid selected from the group consisting of adipic acid, pimelitic acid, azelaic acid and suberic acid, and a polyoxyalkylene diamine.
  • This polyamide is characterized by the properties of a remoistenable adhesive and an outstanding balance of non-block characteristics under heat and high humidity conditions combined with excellent bond strength without the aid of wax, tackifiers or antioxidants and is an improvement over the prior art.
  • This invention is an improvement over known remoistenable adhesives used in the envelope and packaging industry and other related industries, and is also a novel use for known polyamide hot melts.
  • These polyamides though having water soluble tendencies, are also remoistenable in nature, and provide superior bonding and are resistant to high temperature and high humidity.
  • the additions of additives such as waxes, tackifiers and antioxidants are not required to prevent blocking and to promote stability in high heat and humidity.
  • the present invention provides an improvement to the stability of the remoistenable adhesive in severe conditions, and at the same time provides a new use for polyamides.
  • the invention is an improvement in the bonding method of an envelope in which an envelope, having a folding closure flap and having a film of remoistenable adhesive applied thereto, is stored for a period of time, after such time the remoistenable adhesive is moistened, and the flap is folded over onto the envelope and pressed against the envelope until bonded, the improvement comprising that the remoistenable adhesive is a hot melt consisting of a thermoplastic polyamide prepared from an acid component selected from the group consisting of adipic acid, pimelic acid, azelaic acid and suberic acid, and an alkyleneoxy diamine component consisting of one or more diamine compounds having the formula:
  • Fig. 1 is a rear view of an open envelope in accordance with the present invention illustrating the application of the remoistenable adhesive
  • Fig. 2 is a rear view of a closed envelope in accordance with the present invention illustrating the utility of the remoistenable adhesive.
  • thermoplastic polyamides as remoistenable adhesives for their application in the packaging and envelope industry and other related industries, such as application to envelopes, stamps, packaging tape or stickers and labels.
  • polyamides such as these do not require the use of waxes, tackifiers and antioxidants to prevent blocking and to promote thermal stability in high heat and humidity.
  • thermoplastic polyamides are generally prepared using a dicarboxylic acid selected from the group consisting of adipic acid, pimelitic acid, azelaic acid and suberic acid, and alkyleneoxy diamines.
  • the typical formula comprises adipic acid and TTD diamine in exact stoichiometric ratio.
  • products made from adipic acid in conjunction with stearic acid, benzoic acid or sebacic acid and the TTD diamine also showed the remoistening property.
  • Low to high viscosity polyamides can be made for remoistening application by changing the ratio of the acid and amine.
  • Waxes and/or tackifiers are not necessary to show the remoistenable property in the present invention as they are in known remoistenable adhesives, but may be used in certain situations to increase the blocking resistance and thermal stability.
  • Polyamides have been produced for many reasons, but not for use as a remoistenable adhesive. Some polyamides were created in response to a need for satisfactory replacements for naturally derived materials, and can be prepared from relatively inexpensive and readily available synthetic materials. Water soluble polyether amides produced by reacting polyalkylene glycol diamine with dicarboxilic acids were created to provide novel polyether amides with terephthalamide units having improved water absorbency, and/or which are soluble in water. It also was a purpose of past polyamide inventions to provide a plurality of easily implemented methods for making these novel materials. Still, this product has not been recognized for its usefulness as a remoistenable adhesive.
  • Figs. 1 & 2 illustrate an application for the improvement in the bonding method for closing an envelope wherein the remoistenable adhesive used is a polyamide.
  • an open envelope generally designated 10, as shown in Fig. 1, having a folding closure flap 2
  • the envelope can be stored for a period of time, after which the remoistenable adhesive 4 is moistened, usually by licking the adhesive, and the flap 2 is folded over along the crease point 3 onto the back face 6 of the envelope and pressed against the envelope until a bond 8 is created.
  • a sealed envelope 20 as shown is Fig. 2.
  • This application is only an example of the use of polyamides as remoistenable adhesives.
  • Other applications include applying the adhesive to either the closure flap 2 or the back face 6 of the envelope or both, and/or using other envelope type products.
  • the adhesive can be used in a similar manner in conjunction with other forms of packaging material, such as packing tape and the like.
  • Polyamides made from adipic acid and TTD (3, 3 (diethylene trioxy) bispropylamine) diamine have been described in U.S. patent 3,883,090 for various applications, and several other U.S. patents (patent numbers 4,623,688; 5,053,484; 4,133,803; 5,086,162) describe the synthesis of water soluble polyamides using oxyethylene or oxypropylene diamines. These patents disclose that polyamides can be used as hot melt adhesives, but they do not describe or infer the remoistenable property of the polyamide.
  • water-dispersable polyamides can be prepared by reacting adipic acid with a diamine, such as polyethylene glycol diamines, like triethylene glycol diamine (Jeffamine ® EDR-148) or tetraethylene glycol diamine (Jeffamine ® ER-192) or a combination of the two diamines.
  • a diamine such as polyethylene glycol diamines, like triethylene glycol diamine (Jeffamine ® EDR-148) or tetraethylene glycol diamine (Jeffamine ® ER-192) or a combination of the two diamines.
  • a combination of these higher diacids with adipic acid can produce water-soluble or water-dispersible polyamides.
  • Increasing the amount of higher carbon diacids in conjunction with adipic acid results in polyamide with decrease in solubility. However, this can be compensated by increasing the EO (ethylene oxide) content of a portion of the polyethylene glycol diamine component.
  • Jeffamine* ED 600, ED 900, ED 2000, D-230, D-400 and D- 2000 are examples of higher EO content polyoxyalkylene diamines which may be employed.
  • Dimer Acid can be used in combination with adipic acid when triethylene glycol diamine or tetraethylene glycol diamine are employed in combination with the polyoxyalkylene diamines Jeffamine* ED 600 or D-400.
  • TTD Triamine
  • stearic acid benzoic acid or sometimes sebacic acid
  • the reaction of TTD and adipic acid should be used in equal stoichiometric ratio, however, for reaction between adipic acid, TTD, and sebacic acid the limit of sebacic can be between 0- 25% .
  • the limit of stearic acid can be 0-15%.
  • the remoistening adhesives have many applications and can be used in the envelope industry as well as in the packaging industry for paper tapes as remoistenable paper tapes.
  • the water solubility of the adhesive provides a completely repulpable tape for packaging application and is thus recyclable.
  • the hot melt adhesives used in the invention are able to maintain adequate bond strength so that in warm temperatures the seal is not jeopardized.
  • the polyamides display excellent humidity resistance, high thermal stability and showed good blocking resistance at high temperature and high humidity without the aid of tackifiers, waxes or formulation. Some of the polyamides tend to have slow set time, but this can be decreased by using some fast setting waxes.
  • the present invention is advantageous over the prior art/background technologies in that they resist blocking at high humidity and temperature.
  • the polyamides employed in the invention do not require these additional materials to achieve these desirable properties.
  • remoistenable adhesives of the invention may be made solely from mixtures of diamines and mixtures of diacids which also showed remoistenable properties, in some cases in order to achieve a particular property for certain applications or to reduce the cost of the adhesive the polyamides may be optionally formulated with waxes, tackifiers, antioxidants, melt viscosity modifiers, and the like, provided that the additives do not themselves adversely affect the water dispersability of the adhesive formulation.
  • tackifiers are (1) natural and modified rosins such, for example, as gum rosin, wood rosin, tall-oil resin, distilled rosin, hydrogenated rosin, dimerized rosm, and polymerized rosin, (2) polyterpene resins having a softening point, as determined by ASTM method E28 58T, of from about 60° to 140° C, the latter polyterpene resins generally resulting from the polymerization of terpene hydrocarbons, such as bicyclic mono-terpene known as pinene in the presence of Friedel-Crafts catalysts at moderately low temperature, (3) phenolic-modified terpene resins such, for example, as the resin product resulting from the condensation in an acidic medium, of a bicyclic ter
  • Antioxidants or stabilizers which may be employed in remoistenable hot melt compositions include phenolics, amines, and quinones or the like. Especially useful are the high molecular weight hindered phenols and multifunctional phenols such as sulfur and phosphorous-containing phenols.
  • Hindered phenols are well known to those skilled in the art and may be characterized as phenolic compounds which also contain bulky radicals in close proximity to the phenolic hydroxyl group thereof.
  • tertiary butyl groups generally are submitted onto the benzene ring in at least one of the other positions relative to the phenolic hydroxy group. The presence of these substituted radicals in the vicinity of the hydroxyl group serves to retard its stretching frequency and correspondingly, its reactivity. This steric hindrance thus provides the phenolic compound with its stabilizing properties.
  • the polyamides of the present invention show the ability of absorbing moisture without becoming deliquescent. Deliquescent is the tendency to undergo gradual dissolution and liquidefaction by the attraction of moisture from air. Although the polyamides absorbed 30% moisture they were not deliquescent, in fact they desorbed after sitting in ambient conditions. Polymers normally used as remoistenable adhesives like PeOX are deliquescent (tending to undergo gradual dissolution and liquefaction by the attraction of moisture from air) and stays in that form even when they are removed from high humidity. This characteristic causes them to block at high humidity and temperature. To determine if the polyamides are deliquescent a moisture absorption test was administered and is explained below.
  • Adipic acid + Jeffamine EDR 148 polyamide
  • Adipic acid + Jeffamine EDR 148 -I- D-230 polyamide
  • Adipic acid + Jeffamine EDR 148 + D-230 + sebacic acid polyamide
  • Adipic acid (hexane dioic acid) - HOOC-(CH 2 ) 4 -COOH
  • polyamides employed in the invention may be prepared as described in Example 1 of U.S. 3,882,090. Modifications of the recipe given below for illustrative purposes only, it being understood that those skilled in the art can readily modify the recipes without departing from the invention hereof:
  • Polyamide melt viscosity can be controlled by adding small amounts, typically less than 5%, preferably 0.5-2.5% based on total acid weight of monoacids such as stearic or benzoic acid.
  • An example recipe is given below:
  • Elements such as adipic acid, diamine, stearic acid, benzoic acid, and sebacic acid enhance the water solubility of the adhesive.
  • Non-essential elements such as wax, tackifiers and antioxidants contribute properties that are lacking in particular situations. Wax increases setting/lowering the set time/filler, tackifiers help tackiness and antioxidants allows use at high temperature without degradation.
  • NP-2068 parts by weight: adipic acid 145.4; stearic acid 2.7; and TTD Diamine 220.3
  • the batch of NP-2068 was drawn to film for the test.
  • Four strips of paper were cut and weighed and placed in a desiccator at 55-60% humidity and room temperature of 70-75°F.
  • a second set were placed at room temperature in a desiccator with water at the bottom at 70-75 °F with a relative humidity at 95-98%.
  • the samples were weighed and left out in ambient conditions. There was an initial tackiness, but after 24 hours, they were weighed and displayed a lower weight, thus evidencing desorbing of moisture. This desorbing quality helps the sample to resist blocking.
  • Table #1 The results of the absorbency testing are shown below in Table #1 :
  • RT Room Temperature
  • RH Relative Humidity
  • NP-2068 parts by weight: adipic acid 145.4; stearic acid 2.7; and TTD Diamine 220.3 (samples A & B are separate samples of NP- 2068).
  • the test to determine the remoistenability of hot melt adhesives is used to determine whether a remoistenable hot melt adhesive, after initial application, gives adequate bonding when remoistened and mated to a particular substrate.
  • the sample is heated to 300°F.
  • a sheet of paper is taped down on which the adhesive is drawn down with a metal draw down bar.
  • the adhesive is allowed to cool.
  • After which the paper is cut into 1/2" strips with a thickness of between .6 mil. and 1 mil. These strips are allowed to sit at low humidity (50%) for two hours.
  • the strips are moistened with room temperature water and immediately pressed onto a second piece of bond paper with medium finger pressure as if you were sealing an envelope.
  • the test to determine the blocking potential of hot melt adhesives is used to determine whether remoistenable hot melt adhesive, after initial application, will have undesirable blocking characteristics under pressure and heat.
  • the procedure for this test is the same as the remoistenability test up to the point where the strips of paper are allowed to stand in low humidity for two hours.
  • the strips of the control and the strips of the test adhesive are placed on a tray, adhesive side up.
  • a strip of dried bond paper is placed on top of each adhesive strip.
  • a 100 gram weight is placed on top of each strip, and the tray is placed in a 120° oven for 24 hours. Another tray of specimens is placed in room temperature for 24 hours also.
  • n 4577-76 36.31% Adipic acid, 58.04% TTD Diamine, 4.16% Stearic acid & 1.49% Irganox 1098 (antioxidant).

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  • 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)
  • Polyamides (AREA)
  • Adhesive Tapes (AREA)

Abstract

Nouvel adhésif réhumectable et amélioration du procédé de collage d'une enveloppe, d'un timbre, d'un autocollant, d'une bande d'emballage ou d'une étiquette grâce à un adhésif réhumectable. Ledit adhésif réhumectable est un adhésif thermofusible constitué de polyamide thermoplastique préparé à partir d'un constituant acide sélectionné dans le groupe comprenant acide adipique, acide pimélique, acide azélaïque, acide subérique et acide sébacique et d'un constituant alkylèneoxy diamine comprenant un ou plusieurs composés diamine de formule H2N-CyH2y-(OC2H4)x-O-CyH2y-NH2, dans laquelle y vaut 2 ou 3 et x vaut de 1 à 50.
PCT/US1995/000124 1994-09-16 1995-01-05 Polyamides utilises en tant qu'adhesifs rehumectables Ceased WO1996008538A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP95907982A EP0788531A4 (fr) 1994-09-16 1995-01-05 Polyamides utilises en tant qu'adhesifs rehumectables
AU15983/95A AU691871B2 (en) 1994-09-16 1995-01-05 Polyamides as remoistenable adhesives
NZ279381A NZ279381A (en) 1994-09-16 1995-01-05 Use of remoistenable adhesive comprising a hot melt thermoplastic prepared from a (poly)etheramine
JP8510150A JPH10507783A (ja) 1994-09-16 1995-01-05 再湿型接着剤としてのポリアミド

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US30731194A 1994-09-16 1994-09-16
US08/307,311 1994-09-16

Publications (1)

Publication Number Publication Date
WO1996008538A1 true WO1996008538A1 (fr) 1996-03-21

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Family Applications (1)

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PCT/US1995/000124 Ceased WO1996008538A1 (fr) 1994-09-16 1995-01-05 Polyamides utilises en tant qu'adhesifs rehumectables

Country Status (6)

Country Link
EP (1) EP0788531A4 (fr)
JP (1) JPH10507783A (fr)
AU (1) AU691871B2 (fr)
CA (1) CA2199813A1 (fr)
NZ (1) NZ279381A (fr)
WO (1) WO1996008538A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5837802A (en) * 1997-08-29 1998-11-17 H. B. Fuller Licensing & Financing, Inc. Fast setting water sensitive polyamides having a high Tg
US5866675A (en) * 1995-11-09 1999-02-02 H. B. Fuller Licensing & Financing, Inc. Nonwoven web comprising water soluble polyamides and articles constructed therefrom
US5869596A (en) * 1995-11-09 1999-02-09 H. B. Fuller Licensing & Financing, Inc. Fibers comprising water soluble polyamides and articles constructed therefrom
WO1999035203A1 (fr) * 1998-01-08 1999-07-15 Linear Products Inc. Ficelles de renforcement ou rubans adhesifs a ouverture detachable, a activation a l'eau, pour conteneurs en carton ondule ou plat
US6103809A (en) * 1995-11-09 2000-08-15 H.B. Fuller Licensing & Financing, Inc. Thermoplastic compositions comprising crystalline water soluble polymers and amorphous water sensitive polymers
EP3434714A1 (fr) * 2017-07-25 2019-01-30 Henkel AG & Co. KGaA Polymère de polyamide soluble dans l'eau et son utilisation en tant qu'additif fonctionnel
CN114106716A (zh) * 2021-12-22 2022-03-01 浙江金三发粘合衬有限公司 一种适用针织羊绒面料的粘合衬及其制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2804395A (en) * 1953-09-04 1957-08-27 Setrak K Boyajian Envelopes and the like with remoistenable adhesive comprising polyvinyl alcohol
US3462342A (en) * 1965-01-18 1969-08-19 Battelle Development Corp Adhesive bonding
US5324812A (en) * 1993-04-01 1994-06-28 Texaco Chemical Company Water soluble polyamide from polyalkylene glycol diamines and polycarboxylic acids

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2804395A (en) * 1953-09-04 1957-08-27 Setrak K Boyajian Envelopes and the like with remoistenable adhesive comprising polyvinyl alcohol
US3462342A (en) * 1965-01-18 1969-08-19 Battelle Development Corp Adhesive bonding
US5324812A (en) * 1993-04-01 1994-06-28 Texaco Chemical Company Water soluble polyamide from polyalkylene glycol diamines and polycarboxylic acids

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP0788531A4 *

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5866675A (en) * 1995-11-09 1999-02-02 H. B. Fuller Licensing & Financing, Inc. Nonwoven web comprising water soluble polyamides and articles constructed therefrom
US5869596A (en) * 1995-11-09 1999-02-09 H. B. Fuller Licensing & Financing, Inc. Fibers comprising water soluble polyamides and articles constructed therefrom
US6103809A (en) * 1995-11-09 2000-08-15 H.B. Fuller Licensing & Financing, Inc. Thermoplastic compositions comprising crystalline water soluble polymers and amorphous water sensitive polymers
US5837802A (en) * 1997-08-29 1998-11-17 H. B. Fuller Licensing & Financing, Inc. Fast setting water sensitive polyamides having a high Tg
WO1999010599A1 (fr) * 1997-08-29 1999-03-04 H.B. Fuller Licensing & Financing, Inc. POLYAMIDES SENSIBLES A L'EAU, A FIXATION RAPIDE ET A Tg ELEVEE
WO1999035203A1 (fr) * 1998-01-08 1999-07-15 Linear Products Inc. Ficelles de renforcement ou rubans adhesifs a ouverture detachable, a activation a l'eau, pour conteneurs en carton ondule ou plat
US7041194B1 (en) 1998-01-08 2006-05-09 Adalis Corporation Moisture activated reinforcement string and tear opening tapes for corrugated and cartonstock containers
EP3434714A1 (fr) * 2017-07-25 2019-01-30 Henkel AG & Co. KGaA Polymère de polyamide soluble dans l'eau et son utilisation en tant qu'additif fonctionnel
WO2019020585A1 (fr) * 2017-07-25 2019-01-31 Henkel Ag & Co. Kgaa Polymère polyamide hydrosoluble et son utilisation en tant qu'additif fonctionnel
US11384202B2 (en) 2017-07-25 2022-07-12 Henkel Ag & Co. Kgaa Water-soluble polyamide polymer and use thereof as functional additive
CN114106716A (zh) * 2021-12-22 2022-03-01 浙江金三发粘合衬有限公司 一种适用针织羊绒面料的粘合衬及其制备方法
CN114106716B (zh) * 2021-12-22 2023-11-10 浙江金三发粘合衬有限公司 一种适用针织羊绒面料的粘合衬及其制备方法

Also Published As

Publication number Publication date
EP0788531A1 (fr) 1997-08-13
AU1598395A (en) 1996-03-29
AU691871B2 (en) 1998-05-28
CA2199813A1 (fr) 1996-03-21
EP0788531A4 (fr) 1998-01-07
JPH10507783A (ja) 1998-07-28
NZ279381A (en) 1998-06-26

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