Ex Parte Baidak et alDownload PDFPatent Trial and Appeal BoardJun 15, 201612787719 (P.T.A.B. Jun. 15, 2016) Copy Citation UNITED STA TES p A TENT AND TRADEMARK OFFICE APPLICATION NO. FILING DATE 121787,719 05/26/2010 8015 7590 06/17/2016 CYTEC INDUSTRIES INC 1937 WEST MAIN STREET STAMFORD, CT 06902 FIRST NAMED INVENTOR Alexandre A. BAIDAK UNITED STATES DEPARTMENT OF COMMERCE United States Patent and Trademark Office Address: COMMISSIONER FOR PATENTS P.O. Box 1450 Alexandria, Virginia 22313-1450 www .uspto.gov ATTORNEY DOCKET NO. CONFIRMATION NO. 09001S-US-NP 5178 EXAMINER MCCULLEY, MEGAN CASSANDRA ART UNIT PAPER NUMBER 1767 NOTIFICATION DATE DELIVERY MODE 06/17/2016 ELECTRONIC Please find below and/or attached an Office communication concerning this application or proceeding. The time period for reply, if any, is set in the attached communication. Notice of the Office communication was sent electronically on above-indicated "Notification Date" to the following e-mail address( es): StamfordPatent@solvay.com Cheryle.Telesco@solvay.com Rocio.Ramos@solvay.com PTOL-90A (Rev. 04/07) UNITED STATES PATENT AND TRADEMARK OFFICE BEFORE THE PATENT TRIAL AND APPEAL BOARD Ex parte ALEXANDRE A. BAIDAK and PATRICK TERENCE MCGRAIL Appeal2015-000477 Application 12/787,719 Technology Center 1700 Before CHUNG K. PAK, BEYERL YA. FRANKLIN, and AVEL YN M. ROSS, Administrative Patent Judges. ROSS, Administrative Patent Judge. DECISION ON APPEAL 1 Appellants2 appeal under 35 U.S.C. § 134(a) from a final rejection of claims 1, 2, 7, 11-16, 18-23 and 25-27. We have jurisdiction under 35 U.S.C. § 6(b ). We AFFIRM. 1 In our decision below, we refer to the Final Office Action appealed from, mailed September 6, 2013 (Final Act.), the Appeal Brief filed February 3, 2014 (Appeal Br.), the Examiner's Answer mailed August 4, 2014 (Ans.), and the Reply Brief filed October 2, 2014 (Reply Br.). 2 Appellants identify the real party in interest as Cytec Technology Corp. Appeal Br. 2. Appeal2015-000477 Application 12/787,719 STATEMENT OF CASE The claims are directed to engineered crosslinked thermoplastic particles for interlaminar toughening of composite materials. Spec. 1. Claim 1, reproduced below, is illustrative of the claimed subject matter: 14. An engineered crosslinked thermoplastic particle comprising a crosslinked network formed by reacting (a) a thermoplastic polymer having backbone or end functional groups with (b) a polyfunctional cross linking agent that is reactive with the functional groups of the thermoplastic polymer and has a reactivity of two or greater, and wherein the engineered crosslinked thermoplastic particle is in a particulate form adapted to be combined with an uncured thermosetting resin or dispersed in a fiber preform without matrix resin, and is capable of swelling in an uncured thermosetting resin. Claims Appendix at Appeal Br. 12. REJECTIONS The Examiner made the follo\~1ing rejections: A. Claims 14--16 and 27 stand rejected under 35 U.S.C. § 102(b) as being anticipated by Shibuya. 3 Final Act. 2. B. Claims 1, 2, 7, 11-13, and 26 stand rejected under 35 U.S.C. §103(a) as being unpatentable over Shibuya in view ofBoyd.4 Id. at 4. C. Claim 18 stands rejected under 35U.S.C.§103(a) as being unpatentable over Shibuya in view Carter. 5 Id. at 6. Id. 3 Shibuya et al., US 6,531,568 B 1, issued March 11, 2003 (hereinafter Shibuya") 4 Boyd et al., US 5,189,116, issued February 23, 1993 (hereinafter "Boyd"). 5 Carter et al., US 2007/0196619 Al, published August 23, 2009 (hereinafter "Carter"). 2 Appeal2015-000477 Application 12/787,719 D. Claim 19 stands rejected under 35 U.S.C. U.S.C. §103(a) as being unpatentable over Shibuya in view Udipi. 6 Id. at 6-7. E. Claims 20 and 25 stand rejected under 35 U.S.C. U.S.C. § 103 (a) as being unpatentable over Shibuya m view Lubowtiz.7 Id. at 7-8. Appellants seek our review of Rejections A-E above. OPINION Rejection A-Anticipation (claims 14-16 and 27) The Examiner rejects claims 14--16 and 27 as anticipated by Shibuya. Final Act. 2. The Examiner finds that Shibuya teaches a crosslinked thermoplastic particle (col. 52 lines 15-25) formed by reacting a thermoplastic polymer having backbone functional groups (col. 24 lines 45-56) and a polyfunctional crosslinking agent that is reactive with the functional groups of the polymer and has a reactivity of two or greater/itself, which has two end functional groups (col. 44 lines 20-25). Shibuya et al. teaches the particles can be added, as is, to other resins. Since the particles of Shibuya et al. are made with the same components as the instant particles, the ability of the particles to swell in an uncured thermosetting resin is a latent property. Id. Additionally, the Examiner finds that Shibuya teaches a polyetherimide that has a "carboxylic acid functionality group on the ends." Id. at 2-3. The Examiner also finds that the "molecule itself acts as its own crosslinking agent." Id. at 3. 6 Udipi, US 5,051,469, issued September 24, 1991 (hereinafter "Udipi"). 7 Lubowtiz et al., US 5,756,597, issued May 26, 1998 (hereinafter "Lubowtiz"). 3 Appeal2015-000477 Application 12/787,719 Appellants argue claims 14--16 separately, but make no argument with respect to claim 27. Appeal Br. 4--6. Claim 27 therefore stands or falls with the claim from which it depends, or claim 14. Claim 14: Appellants argue, with respect to claim 14, that "[i]t is clear from Shibuya's disclosure, however, that the end blocking agent (C) is not used to react with the functional groups of a thermoplastic polymer to make a crosslinked particle, instead, the end blocking agent (C) is used to make a crosslinkable polymer; i.e., the polyimide with crosslinkable groups." Id. at 4--5. And, according to Appellants, the "end blocking agent having a crosslinkable group" of Shibuya is not the "polyfunctional crosslinking agent" recited in claim 14. Id. at 5. Appellant also argues that because the thermoplastic particles are not the same-i.e., they are not made from the same components-they are not "capable of swelling in the thermosetting resin" according to the claims. Id. The Examiner further explains that the "thermoplastic polymer having backbone or end functional groups" claimed is the polyetherimide polymer of Shibuya, whereas the end blocking agent described in the reference is a reactant used to form the polyetherimide polymer. The polyetherimide self-crosslinks through its functional groups. Therefore, the polyetherimide of Shibuya is both the (a) thermoplastic polymer having backbone or end functional groups claimed and (b) a polyfunctional crosslinking agent that is reactive with the functional groups of the thermoplastic polymer and has a reactivity of two or greater. Ans. 2. Appellants, in rebuttal, argue that the thermoplastic polymer having end functional groups and the polyfunctional crosslinking agent cannot be the same compound. Reply Br. 2. According to Appellant, the Specification describes them as separate compounds to further the ability to tailor the properties of the composite. Id. at 3. Specifically, Appellant argues that by 4 Appeal2015-000477 Application 12/787,719 controlling the crosslink density by changing the crosslinker concentration, the swell factor of the particles can be modified. Id. And, "[ c ]hanging the crosslinker concentration relative to the concentration of the thermoplastic polymer to control the crosslink density is only possible when these compounds are different entities." Id. We agree with the Examiner for the reasons expressed in the Final Action and Answer. Moreover, we note that Appellants' argument regarding the requirement that thermoplastic polymer having end functional groups and the polyfunctional crosslinking agent must be separate and different compounds to control crosslink density is unconvincing as they are based on unclaimed limitations. The claims are silent regarding crosslink density as well as swell factor. See In re Self, 671 F.2d 1344, 1348 (CCPA 1982) ("[A]ppellant's arguments fail from the outset because ... they are not based on limitations appearing in the claims."). The claims require only that the thermoplastic particle is capable of swelling in the thermosetting resin. And as the Examiner correctly found, "[ s ]ince the particles of Shibuya et al. are made with the same components as the instant particles, the ability of the particles to swell in an uncured thermosetting resin is a latent property." Final Act. 2. Moreover, Appellants explain in the Specification that Although one may be able to predict in some circumstances whether or not thermoplastic particles are compatible with the resin, one way to test whether thermoplastic particles are thermodynamically compatible with resin is to combine particles with a resin to determine whether the resin swells the particles without dissolving them and to prepare a cured material to determine whether the particles maintain themselves as discrete particles after curing. Examples of thermoplastic particles that 5 Appeal2015-000477 Application 12/787,719 are thermodynamically compatible with epoxy resin include polyetherimide, polysulfone, polyethersulfone. Spec., p. 14, 11. 19-27 (emphasis added). Notably, the Specification describes polyetherimides and polyethersulfones as thermodynamically compatible, and therefore swellable---each thermoplastic particle is taught by Shibuya. Shibuya, col. 53, 11. 53-54. Accordingly, we find no reversible error in the Examiner's rejection of claim 14 as anticipated by Shibuya. See, e.g., In re Spada, 911 F.2d 705, 708 (Fed. Cir. 1990) ("[W]hen the PTO shows sound basis for believing that [the functionally defined properties] of the products of the applicant and the prior art are the same, the applicant has the burden of showing that they are not.") Claim 15: Claim 15 requires that the thermoplastic polymer be selected from "poly ether sulfone (PES), poly ether ether sulfone (PEES), poly etherimide (PEI), poly phenylene oxide (PPO), and a copolymer thereof." Claims Appendix at Appeal Br. 12. The Examiner finds that Shibuya teaches a polyetherimide, or PEI. Final Act. 2. Appellants argue that "[t]he chemical structure being referred represents the cross linkable-group-containing polyimide of Shibuya's invention, but this structure is not reacted with a polyfunctional crosslinking agent to form a swellable, crosslinked particle." Appeal Br. 6. For the reasons discussed above for claim 14, we find no reversible error in the Examiner's findings. Claim 16: Claim 16 additionally requires that the polyfunctional crosslinking agent be selected from "alkylated melamine derivatives, acid chlorides, multi-functional epoxies, carboxylic acids, and alkylated glycoluril resins." Claims Appendix at Appeal Br. 12. The Examiner finds 6 Appeal2015-000477 Application 12/787,719 that Shibuya teaches a polyetherimide having carboxylic acid functional groups which "acts as its own crosslinking agent." Final Act. 3. Appellants argue that the Examiner applies a different construction for claim 14 and claim 16. Id. at 6. Appellants also argue that Shibuya does not teach the crosslinking agents recited by the claims. Specifically, Appellants argue that Shibuya discloses dicarboxylic acid anhydride which is not equivalent to carboxylic acid. Reply Br. 5. We agree with the Examiner. As the Examiner correctly finds, the polyetherimide of Shibuya acts as both the thermoplastic polymer with end functional groups and the polyfunctional crosslinking agent. Ans. 2 and 4. There is no inconsistency in the Examiner's treatment of claims 14 and 16. The Examiner also correctly finds that the "polyetherimide [of Shibuya] has a carboxylic acid functionality on the ends (col. 5 lines 46-52)." Final Act. 3. And, while Shibuya may prefer a carboxylic acid anhydride (col. 44, 11. 20-26), Shibuya teaches that "a dicarboxylic acid or its anhydride" can be used as the end-blocking agent, which the Examiner finds is used to make the polyetherimide-that has both end functional groups and a crosslinking agent. Shibuya col. 43, 11. 43--48. Rejection B - Obviousness (claims 1, 2, 7, 11-13, and 26) The Examiner rejects claims 1, 2, 7, 11-13, and 26 as unpatentable under 35 U.S.C. §103 over Shibuya and Boyd. Final Act. 4. In addition to the findings above for claim 14 which also are relevant for claim 1, the Examiner finds that "[ s ]ince the particles of Shibuya et al. are made with the same components as the instant particles, the ability of the particles to swell in an uncured thermosetting resin forming a gradient interface with the thermosetting resin when the resin system exceeds a specific onset 7 Appeal2015-000477 Application 12/787,719 temperature is a latent property." Id. at 4. The Examiner acknowledges that Shibuya "does not teach an uncured thermosetting resin" but finds that Boyd teaches "engineered thermoplastic particles and a thermosetting resin (col. 1 lines 10-19). Id. According to the Examiner, Shibuya and Boyd both relate to thermoplastic particles and one skilled in the art would be motivated to make the recited combination "to achieve high compression after impact strengths in the composition, as evidenced by Boyd." Id. 4--5. In response to Rejection B, Appellants argue claim 1 alone. Appeal Br. 7. Appellants do not present separate argument with respect to 2, 7, 11- 13, and 26 and therefore, these claims stand or fall with claim 1. Id. Appellants argue that Boyd, while teaching "the incorporation of swellable or soluble thermoplastic particles (preferably, polyimides) into a bismaleimide resin, wherein the particles swell or dissolve during cure (Boyd: col. 7, 11. 9-10)," does not teach crosslinked particles. Id. Therefore, says Appellants, "the combined teachings would not have resulted in the claimed resin system with swellable, crosslinked thermoplastic particles." Id. For the reasons expressed by the Examiner, Appellants do not convince us of reversible error. The test for obviousness is not whether the claimed invention is expressly suggested in any one or all of the references, but whether the claimed subject matter would have been obvious to those of ordinary skill in the art in light of the combined teachings of those references. See In re Keller, 642 F.2d 413, 425 (CCPA 1981). Boyd expressly teaches adding thermoplastic polyimides to an uncured bismaleimide resin. Boyd, col. 4, 11. 12-17. And, while Boyd may not use crosslinked thermoplastics in practicing its invention (as Appellants suggest), Boyd discusses the use of crosslinked structures which are known 8 Appeal2015-000477 Application 12/787,719 to be brittle. Id. at col. 1, 11. 35-39. As a result, those skilled in the art recognize the importance of increasing the toughness in crosslinked polymer systems. Id. Boyd explains that the "subject invention pertains to bismaleimide resin systems contain both a particulate thermoplastic toughener and a minor quantity of a low viscosity epoxy resin." Id. at col. 1, 13-16 (emphasis added). Therefore, we agree with the Examiner that the skilled artisan would have reason to combine the references-in particular, incorporating the uncured resin of Boyd into the crosslinked thermoplastic system of Brooks-to achieve a resin system that possesses improved compression strengths. Boyd col. 1, 11. 12-19 and col. 3, 11. 65-68. Rejection C - Obviousness (claim 18) Claim 18 is rejected by the Examiner as obvious over Shibuya and Carter. Final Act. 6. Claim 18 additionally requires that "the thermoplastic polymer is amine-ended PES/PEES copolymer." Claims Appendix at Appeal Br. 12. The Examiner finds that Shibuya teaches the claimed thermoplastic, as discussed above, but fails to teach that the thermoplastic is an amine-ended PES/PEES copolymer as required by claim 18. Final Act. 6. But, the Examiner finds that Carter "teaches a similar particle having an amine ended PES/PEES copolymer (para. 191 ). " Id. The Examiner also finds that Shibuya and Carter both relate to thermoplastic polymers and a person having ordinary skill in the art would have been motivated to combine these references "to have a flexible polymer element that can be stored at ambient or elevated temperature for extended periods, as evidenced by Carter et al. (para. 192)." Id. Appellants argue that the portion of Carter cited by the Examiner "has nothing to do with forming crosslinked thermoplastic particles" and that 9 Appeal2015-000477 Application 12/787,719 "[a]mine-ended PES/PES is chemically different from the crosslinkable- group-containing polyimide of Shibuya." Appeal Br. 7-8. Appellants also contend that "having a flexible polymer that is soluble in a curable composition is not relevant to the solution being provided by Shibuya." Id. at 8. Therefore, Appellants argue the "Examiner fails to provide evidence showing that amine-ended PES/PEES polymer is similar to the crosslinkable-group-containing polyimides disclosed by Shibuya such that crosslinked particles could be formed using Shibuya's method." Reply Br. 5. For the reasons expressed by the Examiner, we agree with the Examiner. Moreover, we note that Carter teaches that thermoplastics include polyetherimides and polyethersulphones. Carter i-f 50. The thermoplastics are preferably polyaromatic, have substituents that provide cross-linking activity, and comprise a polyaromatic sulphone with ether- linked repeating units. Id. at i-fi-154--56. In addition, the "polyaromatic preferably contain pendant or chain terminating groups" which preferably include amine and hydroxyl end groups. Id. at i-fi-f 67. Rejection D-Obviousness (claim 19) Claim 19 is rejected by the Examiner as unpatentable under 35 U.S.C. § 103 over Shibuya and U di pi. Final Act. 6-7. Claim 19 requires that the "crosslinked thermoplastic particle contains two or more layers." Claims Appendix at Appeal Br. 12. According to the Examiner, Udipi teaches thermoplastic particles "having a core-shell/two layer structure (abstract)" and that one skilled in the art would have been motivated to make the recited combination "to prevent sintering at high temperatures as well as preserve 10 Appeal2015-000477 Application 12/787,719 the particulate form, as evidenced by Udipi (col. 3 lines 4--15)." Final Act. 7. Appellants argue that the core-shell particles of Udipi are "structurally and chemically different from the crosslinked polyimide particles disclosed by Shibuya." Appeal Br. 8. Thus, Appellants contend that "it is not understood how one skilled in the art could modify crosslinked polyimide particles of Shibuya to convert them into core-shell particles based on Udipi's teachings." Id. We find no reversible error in the Examiner's findings and reasoning. The Examiner finds that based on U di pi' s core-shell structure the skilled artisan would have reason to modify the Shibuya crosslinked thermoplastic polymer into two or more layers. Appellants do not dispute the Examiner's finding that the Udipi core-shell structure teaches a layered structure. Final Act. 7. We therefore accept this finding as fact. Appellants' argument that the Examiner's combination lacks rational underpinnings is unpersuasive. In addition to the reasons stated by the Examiner, Udipi recognizes that thermoplastics often crack and become brittle. Udipi, col. 1, 11. 17-23. Udipi teaches that the "core-shell morphology" results in "toughened polymers with superior flexural modulus." Id. at col. 1, 11. 53-59. This is consistent with one of the stated purposes of Shibuya-i.e., improved mechanical properties including flexural modulus. Shibuya col. 1, 11. 12-26 and col. 5, 11. 9-14. 8 8 We also note that this is consistent with the teachings of Boyd that recognizes toughening of the thermoplastic is desirable. Boyd col. 1, 11. 12- 19 and col. 3, 11. 65---68. 11 Appeal2015-000477 Application 12/787,719 Rejection E - Obviousness (claims 20 and 25) The Examiner rejects claims 20 and 25 as unpatentable under 35 U.S.C. § 103 over Shibuya and Lubowtiz. Claims 20 and 25 additionally require that "the molecular weight the thermoplastic polymer is about 3,000- 50,000 g/mol." and "a fiber preform comprising fibers without matrix resin," respectively. Claims Appendix at Appeal Br. 12. According to the Examiner, Lubowtiz teaches crosslinked thermoplastics where the molecular weight of the thermoplastics is in the claimed range. Final Act. 7. The Examiner explains that one skilled in the art would have been motivated to combine the references to achieve thermoplastics that are easy to process to form composites that are tough, have impact resistance, possess superior thermomechanical properties and have superior thermo-oxidative stability, as evidenced by Lubowtiz et al. (col. 8 lines 20-35)." Id. Appellants argue that Lubowtiz "fails to cure the deficiencies of Shibuya with regard to the subject matter of claim 14, on which claim 20 depends." Appeal Br. 8. For the same reasons discussed above with respect to claim 14, Appellants argument fails. With respect to claim 25, the Examiner finds that Lubowtiz "teaches a preform having fiber/layers of fabric and the thermoplast dispersed/flowed into the fibers (col. 10, lines 21-27)." Final Act. 8. Appellants argue that the portions of Lubowtiz relied upon by the Examiner do not teach a preform but rather describe the preparation of prepregs. Appeal Br. 9. And, Shibuya teaches molding the polyimide by sinter molding or melt/molding (Appeal Br. 9) and "a device for shaping thermoplastic material" (Reply Br. 6). As a result, Appellants argue that "[i]t is not understood how Shibuya and Lubowtiz could be combined to arrive at a fiber preform with crosslinked thermoplastic particles dispersed therein." Id. 12 Appeal2015-000477 Application 12/787,719 For the reasons stated by the Examiner, we again find no reversible error. Appellants broadly define preform as "an assembly of fibers, such as unidirectional fibers and woven fabrics, that are ready for receiving a resin." Spec., p. 11, 11. 24--28. Similarly, Appellants claims state that the "fiber preform compris[es] fibers without matrix resin." See Claims Appendix at Appeal Br. 12. Lubowtiz describes methods of preparing prepregs using a layer "fabric or other reinforcement" that is combined with a mixture of oligomers and solvents or interleaved layers of resin film (which comprises an oligomer and solvent). Lubowtiz, col. 10, 11. 15-27. It is the layer of fabric without the oligomer and solvent (i.e., the resin) that comprises the preform. And, as the Examiner finds, a person skilled in the art would have reason to add or disperse the engineered crosslinked thermoplastic particles of Shibuya (col. 51, 11. 14--20) as is (without a resin) to the fiber preform of Lubowtiz, in order to improve mechanical properties among others. Lubowtiz, col. 1, 11. 60-61 ("improved toughness and thermomechanical stability) and col. 8, 11. 28-29 ("composites that are tough, have impact resistance, possess superior thermomechanical properties," etc.); Shibuya, col. 1, 11. 12-26 ("excellent mechanical properties"), col. 4, 1. 65 (improved "mechanical properties at high temperatures"), and col. 5, 11. 9-14 (mechanical properties such as "compression test ... flexural modulus, Izod impact value, and the like."). CONCLUSION The Examiner did not reversibly err in rejecting claims 14--16 and 27 under 35 U.S.C. §102(b) as being anticipated by Shibuya. 13 Appeal2015-000477 Application 12/787,719 The Examiner did not reversibly err in rejecting claims 1, 2, 7, 11-13, and 26 under 35 U.S.C. §103(a) as being unpatentable over Shibuya in view of Boyd. The Examiner did not reversibly err in rejecting claim 18 under 35 U.S.C. §103(a) as being unpatentable over Shibuya in view Carter. The Examiner did not reversibly err in rejecting claim 19 under 35 U.S.C. § 103(a) as being unpatentable over Shibuya in view Udipi. The Examiner did not reversibly err in rejecting claims 20 and 25 under 35 U.S.C. §103(a) as being unpatentable over Shibuya in view Lubowtiz. DECISION For the above reasons, the Examiner's rejection of claims 1, 2, 7, 11- 16, 18-23 and 25-27 is affirmed. No time period for taking any subsequent action in connection with this appeal may be extended under 37 C.F.R. § 1.136(a)(l )(iv) (2009). AFFIRMED 14 Copy with citationCopy as parenthetical citation