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Use of a Crosslinking Agent, Crosslinked Polymer, and Uses Thereof

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Use of a Crosslinking Agent, Crosslinked Polymer, and Uses Thereof (19) TZZ Z_T (11) EP 2 452 970 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C08K 5/09 (2006.01) B32B 27/30 (2006.01) 21.01.2015 Bulletin 2015/04 C08L 29/04 (2006.01) C08L 101/00 (2006.01) G02B 5/30 (2006.01) C08K 5/098 (2006.01) (2006.01) (21) Application number: 12154871.3 C08K 5/10 (22) Date of filing: 29.08.2008 (54) Use of a crosslinking agent, crosslinked polymer, and uses thereof Verwendung eines Vernetzungsmittels, vernetztes Polymer und Verwendungen davon Utilisation d’un agent de réticulation, polymère réticulé et utilisations associées (84) Designated Contracting States: (72) Inventors: AT BE BG CH CY CZ DE DK EE ES FI FR GB GR • Kageyama, Hideki HR HU IE IS IT LI LT LU LV MC MT NL NO PL PT Osaka-shi, Osaka 530-0018 (JP) RO SE SI SK TR • Tanaka, Shinichi Osaka-shi, Osaka 530-0018 (JP) (30) Priority: 31.08.2007 JP 2007225012 • Ono, Hiroyuki 18.03.2008 JP 2008069645 Osaka-shi, Osaka 530-0018 (JP) 04.04.2008 JP 2008098282 • Kuruma, Akiko 11.04.2008 JP 2008103494 Osaka-shi, Osaka 530-0018 (JP) 24.04.2008 JP 2008114149 24.04.2008 JP 2008114150 (74) Representative: Kuhnen & Wacker Patent- und Rechtsanwaltsbüro (43) Date of publication of application: Prinz-Ludwig-Straße 40A 16.05.2012 Bulletin 2012/20 85354 Freising (DE) (62) Document number(s) of the earlier application(s) in (56) References cited: accordance with Art. 76 EPC: WO-A1-2005/087711 JP-B2- 3 612 124 08828502.8 / 2 189 496 US-A1- 2004 102 586 (73) Proprietor: The Nippon Synthetic Chemical • DATABASE WPI Week 198020 Thomson Industry Co., Ltd. Scientific, London, GB; AN 1980-35516C Osaka 530-0018 (JP) XP002607951, & JP 55 047149 A (MITSUBISHI CHEM IND LTD) 3 April 1980 (1980-04-03) Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 2 452 970 B1 Printed by Jouve, 75001 PARIS (FR) EP 2 452 970 B1 Description Technical Field 5 [0001] The present invention relates to a crosslinking agent, a crosslinked polymer crosslinked with such a crosslinking agent, and uses thereof. Background Art 10 [0002] In crosslinked polymers, since movement of the molecular chains is restrained in three-dimensional directions, the polymers are usually more excellent in strength, heat resistance, solvent resistance, and the like than linear polymers of the same type. Such crosslinked polymers are roughly classified into (i) those each obtained by converting a monomer into a high molecular compound with a crosslinking agent through three-dimensional crosslinking and (ii) those each obtained by 15 intermolecular crosslinking of a linear polymer with a crosslinking agent. [0003] With regard to the crosslinked polymers of (i), most of them are obtained by fabricating a crosslinkable monomer through a reaction of a monomer with a crosslinking agent beforehand and crosslinking the crosslinkable monomer by heating or by means of a catalyst, and representative examples thereof include thermosetting resins such as urea resins, melamine resins, and phenol resins. In all these resins, a crosslinked structure is fabricated by adding an aldehyde 20 compound such as formaldehyde as a crosslinking agent to ureas, melamines, or phenols as a monomer to form a methylol group and subjecting the methylol groups to a condensation reaction. [0004] Moreover, with regard to (ii), crosslinking methods of various liner polymers have been investigated and put into practical use. Of these, a polyvinyl alcohol-based resin (hereinafter polyvinyl alcohol is abbreviated as PVA), which is a water-soluble resin, is a resin to which water resistance can be imparted by crosslinking and thus is one kind of 25 resins where crosslinked structure fabrication is practically extremely important. In the case of the PVA-based resin, examples wherein a hydroxyl group bonded to the main chain is used for crosslinking are widely known. However, in order to enhance crosslinking efficiency and fabricate a strong crosslinked structure, it is preferable to use a PVA-based resin wherein a highly reactive functional group is introduced into the side chain. For example, a PVA-based resin having an acetoacetyl group in the side chain has been employed in uses where a high 30 water resistance is required. [0005] As crosslinking agents for the acetoacetyl group-containing PVA-based resin (hereinafter, the acetoacetyl group-containing resin is abbreviated as AA-PVA-based resin), various compounds are known. Of these, aldehyde compounds have been widely used in various uses since they are excellent in reactivity with the acetoacetyl group and a crosslinking reaction proceeds at relatively low temperature. 35 For example, a crosslinked polymer obtained by crosslinking the AA-PVA-based resin with glyoxal which is a dialdehyde compound is suitably used in a surface protecting layer of heat-sensitive recording media (see e.g., Patent Document 1), an adhesive layer between a polarizing film and a protecting film in polarizers (see e.g., Patent Document 2), and the like. Moreover, in an aqueous emulsion obtained using a polymer containing a repeating structural unit derived from an 40 ethylenically unsaturated monomer as a dispersoid and the AA-PVA-based resin as a dispersant, an example wherein water resistance is imparted to a dry film of the emulsion by the use of glyoxal as a crosslinking agent (see e.g., Patent Document 3). [0006] Furthermore, in recent years, for the purpose of extending a pot life of a mixed aqueous solution of the AA- PVA-based resin and an aldehyde compound, it is investigated to use a compound whose aldehyde group is protected. 45 For example, there has been proposed a heat-sensitive recording medium wherein an acetal compound obtained by protecting an aldehyde group with a polyhydric alcohol such as glucose is used as a crosslinking agent for the AA-PVA- based resin (see e.g., Patent Document 4). The disclosure of document JP 55-047149 A aims to obtain an ion exhange resin having a great heat-regenerative exchange capacity by manufacturing a heat-regenerative ion exchange resin with a specific type of weakly acid cation exchange groups. This resin has weakly acid cation exchange groups and 50 weakly basic anion exchange groups in a same resin particle, wherein the weakly acid cation exchange resin can be manufactured by the procedure in which polyvinyl alcohol and sodium glyoxylate are reacted, bridged with a cross- linking agent, and then treated with an acid. [0007] The disclosure of document JP 3 612 124 B2 aims to obtain a resin composition having water resistance when prepares into film, despite the excellence of its aqueous solution in stability of viscosity, by adding a crosslinking agent 55 to an acetoacetic ester group-containing polyvinyl alcohol-based resin that contains respectively specific quantities of an alkali metal acetate and acetic acid. This resin composition is obtained by adding (B) a crosslinking agent (e.g. aldehyde, amine compound, isocyanate compound or the like) in a quantity of 1-10 wt.% or so based on a component A to (A) an acetoacetic ester group-containing polyvinyl alcohol-based resin which contains an alkali metal acetate in a 2 EP 2 452 970 B1 quantity of 2 wt.% or less and acetic acid in a quantity of 5 wt.% or less (the weight ratio of the acetate to acetic acid is 0.01-100). [0008] 5 Patent Document 1: JP-A-09-164763 Patent Document 2: JP-A-07-198945 Patent Document 3: JP-A-11-279509 Patent Document 4: JP-A-2004-291519 10 Disclosure of This Invention Problems that the Invention is to Solve [0009] As above, aldehyde compounds have been widely used as crosslinking agents for thermosetting resins such 15 as phenol resins and crosslinking agents for linear polymers, especially AA-PVA-based resins. However, formaldehyde, which is a representative compound thereof, has an extremely strong irritating odor and thus it may make working environment worse and may remain in products to cause a bad odor in some cases. [0010] Moreover, in the case where an aldehyde compound is used as a crosslinking agent for the AA-PVA-based resin, the both substances are usually applied to various uses after they are made into an aqueous solution containing 20 them. In that case, since an aldehyde group is highly reactive with an acetoacetyl group, a crosslinking reaction may proceed at room temperature to thicken the aqueous solution during use or during storage and thus workability may decrease or finally the solution may become a gel and impossible to use in some cases. [0011] Furthermore, a crosslinked polymer obtained by crosslinking the AA-PVA-based resin with an aldehyde com- pound frequently used at present, such as formaldehyde or glyoxal, has a problem that it may be colored with time 25 depending on its storage environment. [0012] In this regard, in Patent Document 4, a compound wherein the aldehyde group of formaldehyde is acetalized with a polyol compound such as glucose is proposed as a crosslinking agent for the AA-PVA-based resin. However, in the case where such a compound is used as a crosslinking agent, stability of a mixed aqueous solution with the AA- PVA-based resin and coloring resistance with time of the resulting crosslinked polymer are slightly enhanced but there 30 is yet a room for improvement.
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