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Curable Composition Härtbare Zusammensetzung Composition Durcissable

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Curable Composition Härtbare Zusammensetzung Composition Durcissable (19) TZZ_Z¥Z_T (11) EP 1 036 807 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C08G 65/32 (2006.01) C08L 83/04 (2006.01) 12.12.2007 Bulletin 2007/50 C08G 65/336 (2006.01) C08L 71/02 (2006.01) (21) Application number: 00400747.2 (22) Date of filing: 17.03.2000 (54) Curable composition Härtbare Zusammensetzung Composition durcissable (84) Designated Contracting States: • Kawakubo, Fumio BE CH DE FR GB LI NL Hyogo 654-0151 (JP) (30) Priority: 18.03.1999 JP 7322499 (74) Representative: Hubert, Philippe et al Cabinet Beau de Loménie (43) Date of publication of application: 158, rue de l’Université 20.09.2000 Bulletin 2000/38 75340 Paris Cédex 07 (FR) (73) Proprietor: KANEKA CORPORATION (56) References cited: Osaka-shi, Osaka 530-8288 (JP) EP-A- 0 397 036 EP-A- 0 532 049 EP-A- 0 584 978 EP-A- 0 829 504 (72) Inventors: EP-A- 0 844 266 WO-A-00/40654 • Odaka, Hidetoshi Hyogo 676-0026 (JP) • PATENT ABSTRACTS OF JAPAN vol. 1998, no. • Kanamori, Yuka 03, 27 February 1998 (1998-02-27) & JP 09 296046 Hyogo 673-0018 (JP) A (SANYO CHEM IND LTD), 18 November 1997 • Ito, Hiroshi (1997-11-18) Hyogo 676-0026 (JP) • Jyono, Hideharu Remarks: Hyogo 655-0872 (JP) Thefilecontainstechnicalinformationsubmittedafter • Iwakiri, Hiroshi the application was filed and not included in this Hyogo 651-2277 (JP) specification Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 1 036 807 B1 Printed by Jouve, 75001 PARIS (FR) EP 1 036 807 B1 Description FIELD OF THE INVENTION 5 [0001] The present invention relates to a curable composition comprising a reactive silicon group-containing polyether, a plasticizer and a silane coupling agent. BACKGROUND OF THE INVENTION 10 [0002] Room temperature curing compositions based on a polyether having at least one reactive silicon group per molecule can be utilized, for example, as sealants for architectural and other applications. They are inexpensive and have good performance characteristics. It is desired that they show a proper rate of cure on the occasion of curing. It is also desired that the resulting rubber-like cured products have nonstick surfaces and, as regards tensile characteristics, high elongation and rubber elasticity with good flexibility. 15 [0003] Plasticizers are generally added to room temperature curing compositions not only for the purpose of improving the tensile characteristics which are required of them but also in view of advantages in terms of cost and workability, among others. Some compositions of this type fail to give fully cured products due to formulations thereof and/or curing conditions, so that the product appearance is deteriorated by adhesion of dust and the like due to the residual tack (stickiness) of the cured product surface. Improvements have thus been required. 20 [0004] The present applicant has already proposed, in Japanese Kokai Publication Sho-61-34066 and Japanese Kokai Publication Sho-61-34067, a simple method of producing improvements in the modulus, elongation characteristics and residual tack (stickiness) of a reactive silicon group-containing rubber type organic polymer, which comprises adding a monovalent silanol compound or a derivative thereof. [0005] EP-A-844 266, EP-A-532 049 and EP-A-918 062 discloses curable compositions containing a polyether having 25 an allyl group-derived terminal structure. WO 00/40654 discloses a curable composition containing a silicon group- containing polyether and plasticizer. [0006] While the tensile characteristics of such cured products can be improved by the above method, there is still room for improvement with respect to the residual tack (stickiness). 30 SUMMARY OF THE INVENTION [0007] Accordingly, it is an object of the present invention to provide a curable composition giving cured products improved in residual tack (reduced in stickiness), with the physical properties insuring those tensile characteristics and rubber elasticity required of sealing compositions for general architectural use being retained. 35 [0008] Thus, the present invention provides a curable composition which comprises (I) 100 parts by weight of a reactive silicon group-containing polyether with the percentage of the number of reactive silicon groups to the number of molecular chain terminals as determined by 1H-NMR analysis being not less than 85% and (II) 1 to 500 parts by weight of a plasticizer and (III) a silane coupling agent as defined in present claim 1. 40 DETAILED DESCRIPTION OF THE INVENTION [0009] Hereinafter, the present invention is described in detail. [0010] The reactive silicon group-containing polyether (I) to be used in the curable composition of the present invention has a percentage of the number of reactive silicon groups to the number of molecular chain terminals as determined 45 by 1H-NMR analysis which is not less than 85%. [0011] The reactive silicon group as so referred to herein has at least one hydroxyl group and/or hydrolyzable group bound to a silicon atom and capable of being crosslinked by a mutual condensation reaction to form a siloxane bond. While the above group is not particularly restricted, those groups which are represented by the general formula (1) shown below, for instance, may be mentioned as particularly preferred ones: 50 1 2 - (Si (R 2-b) (Xb)O)mSi (R 3-a) Xa (1) wherein, R1 and R2 are the same or different and each represents an alkyl group containing 1 to 20 carbon atoms, an aryl group containing 6 to 20 carbon atoms, an aralkyl group containing 7 to 20 carbon atoms or a triorganosiloxy group 55 of the formula (R’)3SiO-, in which the three R’ groups are the same or different and each is a monovalent hydrocarbon group containing 1 to 20 carbon atoms, and when there are two or more R1 or R2 groups, they may be the same or different; X represents a hydroxyl group or a hydrolyzable group and, when there are two or more X groups, they may be the same or different; a represents 0, 1, 2 or 3, b represents 0, 1 or 2 and the value of b in two or more recurring 2 EP 1 036 807 B1 units may be the same or different; m represents an integer of 0 to 19; with the condition that the relation a +Σb ≥ 1is satisfied. [0012] As specific examples of R1 and R2 in the above general formula (1), there may be mentioned, among others, alkyl groups such as methyl and ethyl, cycloalkyl groups such as cyclohexyl, aryl groups such as phenyl, aralkyl groups 5 such as benzyl, and triorganosiloxy groups represented by (R’)3SiO- in which R’ is, for example, methyl or phenyl. Among them, methyl is particularly preferred as R1, R2 and R’. [0013] Among the groups represented by X, the hydrolyzable group is not particularly restricted but may be any known hydrolyzable group. Specifically, there may be mentioned a hydrogen atom, halogen atoms, alkoxy groups, acyloxy groups, ketoximate groups, amino groups, amido groups, acid amide groups, aminooxy groups, mercapto groups, 10 alkenyloxy groups and the like. Among these, alkoxy groups such as methoxy, ethoxy, propoxy and isopropoxy are preferred because of their mild hydrolyzability and ease of handling. [0014] One to three hydroxyl groups and/or hydrolyzable groups may be bound to one silicon atom and the sum (a + Σb) is preferably 1 to 5. When two or more hydroxyl and/or hydrolyzable groups occur in the reactive silicon group, they may be the same or different. 15 [0015] The number of silicon atoms in the reactive silicon group may be one or two or more. In cases where the reactive silicon group involves silicon atoms joined together via siloxane bonding or the like, the number of silicon atoms may be up to about 20. [0016] Preferred because of their ready availability are those reactive silicon groups represented by the general formula (8): 20 2 -Si(R 3-a) Xa (8) wherein R2, X and a are as defined above in relation to the general formula (1). [0017] The above reactive silicon group may occur as a side chain internally within the polyether molecule chain or 25 at a terminal thereof. For use as sealants or the like for buildings and the like, it is particularly preferred that said group occur at a terminal of said chain. When the reactive silicon group occurs as an internal side chain, the effective size of network bonding of the polyether component contained in the cured product finally formed becomes small, hence the product tends to become a rubber-like one showing high elasticity modulus and low elongation. On the contrary, when the reactive silicon group occurs in the vicinity of a molecular chain terminal, the effective size of network bonding of 30 the polyether component contained in the cured product finally formed becomes large, hence the product tends to become a rubber-like one showing high strength, high elongation and low elasticity modulus. Particularly when the reactive silicon group occurs at a terminal of the molecular chain, the effective size of network bonding of the polyether component contained in the cured product finally formed becomes maximum, and this is particularly favorable for sealant or like use for buildings where rubber elasticity with high elongation characteristics as tensile characteristics and with 35 rich flexibility is desired.
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