DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claims 1-3, 5, and 11-20, are pending and being examined.
Response to Amendment
The previous objection of Claim(s) 1 for informalities is/are withdrawn in light of the Applicant’s amendments.
The previous rejection of Claims 1-3, 5, 11-16, are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-10 of U.S. Patent No. 11,633,517 B2 is/are withdrawn in light of the Applicant’s amendments.
The previous rejection of Claim(s) 19, under 35 U.S.C. 102(a)(1) as anticipated by US 2009/0099600 A1 to Moore et al. (hereinafter Moore) is/are withdrawn in light of the Applicant’s amendments and arguments.
The previous rejection of Claim(s) 20, under 35 U.S.C. 102(a)(1) as anticipated by Liao et al., “Synthesis and Characterization of Biodegradable Poly(ε-caprolactone)-b-Poly(L-lactide) and Study on Their Electrospun Scaffolds,” Journal of Macromolecular Science, Part A: Pure and Applied Chemistry, vol. 47, pp. 1116-1122. (2010). (hereinafter Liao) is/are withdrawn in light of the Applicant’s amendments and arguments.
The previous rejection of Claim(s) 1-3, 5, 11-13, 15-18, under 35 U.S.C. 102(a)(1) as anticipated by CN 104788695 A to Hou et al. (hereinafter Hou) is/are withdrawn in light of the Applicant’s amendments and arguments.
The previous rejection of Claim(s) 1-3, 5, 11-13, 15-19, under 35 U.S.C. 102(a)(1) as anticipated by Gu et al., “Bio-based polyurethanes with shape memory behavior at body temperature: effect of different chain extenders, RCA Advances, vol. 6, pp. 17888-17895, (2016) (hereinafter Gu) is/are withdrawn in light of the Applicant’s amendments and arguments.
Claim Rejections - 35 USC § 102
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claim(s) 1-3, 5, 11, 12, 17, is/are rejected under 35 U.S.C. 102(a)(1) as anticipated by EP 2,770,004 A1 to Shinozawa et al. (hereinafter Shinozawa). MAINTAIN
Regarding claims 1-3, 5, 11, 12, 17, Shinozawa teaches a biodegradable adhesive comprising a polyurethane resin (See abstract), which is applied upon a surface to form a film. (para 52). Specifically, Shinozawa teaches first obtaining a poly(hydroxycarboxylic acid) polyol A by reacting a mixture (i.e. random) of a sulfonic acid sodium salt group-containing diol, 357 parts (2.48 mols) of L-lactide, and 143 parts (1.25 mols) of caprolactone (para 56), which meets the claimed random copolyester A of 66 mol% lactide, and 34 mol% of caprolactone. The above polyol A is reacted with hexamethylene diisocyanate (HDI) and further reacted with dimethyl propionic acid (DMPA), which is also known as 2,2-bis(hydroxymethyl)propanoic acid, to obtain a reacted mixture (para 57), that is further reacted with an end-blocked PEG (para 57). The above intermediate of the reacted mixture meets the claimed polyurethane wherein the polyol A meets the claimed A segment, the HDI meets the claimed B segment, and the DMPA meets the claimed C segment.
Claim(s) 1-3, 5, 11-13, 15-18, and 20, is/are rejected under 35 U.S.C. 102(a)(1) as anticipated by CN 105273153 A to Sun et al. (hereinafter Sun).
Regarding claims 1-3, 5, 11-13, 15-18, and 20, Sun teaches a biodegradable aqueous emulsion used in the field of coatings and adhesives (See abstract). The emulsion is obtained by first reacting a mixture (random) of 75 g of L-lactide, 25 g of ε-caprolactone, and 1.5 g of ethylene glycol, (See example 3), which meets the claimed polyester A of mol% ε-caprolactone and mol% lactide. The above mixture is then reacted with isophorone diisocyanate (IPDI) until there is an NCO content of 10%, and then further reacted with N-methyldiethanolamine (N-MDEA), (Example 3), to form a prepolymer before being emulsified (page 3), which meets the claimed B-C-B segment of claims 1 and 20. The prepolymer is then mixed with isotridecyl alcohol polyoxyethylene ether and water to form an emulsion. (Example 3).
Claim(s) 1, 2, 5, 11-13, 15-18, and 20, is/are rejected under is/are rejected under 35 U.S.C. 102(a)(1) as anticipated by US 2014/0194533 A1 to Hsu et al. (hereinafter Hsu).
Regarding claims 1, 2, 5, 11-13, 15-18, and 20, Hsu teaches a elastomer with a hard segment and soft segment, wherein the hard segment is formed by reacting a diisocyanate and a chain extender and the soft segment is a biodegradable oligomer diol (See abstract). Specifically, Hsu teaches mixing polycaprolactone diol (PCL) with polyethylene butylene adipate diol (PEBA), poly-L-lactic acid diol (PLLA) and poly-DL-lactic acid diol (PDLLA) and reacting in a prepolymerization reaction to form a macrodiols (para 49-51), which meets the claimed random copolyesters of A. The macrodiols are then further reacted with isophorone diisocyanate (IPDI) and further reacted with the chain extender of 2,2-bis(hydroxymethyl)propionic acid (DMPA) (para 49-51), as shown by Scheme 1,
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, para (51-52). The above prepolymer intermediate after the reaction with DMPA, (para 51), meets the claimed (A-B-C-B)n wherein A is the random macrodiols, B is the IPDI (4 carbons), and C is 2,2-bis(hydroxymethyl)propionic acid (DMPA) (3 carbons), with a B-C-B length of 11. Hsu further teaches the soft segment may contain PLA diol and PCL diol in a molar ratio of 20:80 (See Table 3, para 48), which meets the claim random copolyester of lactide and caprolactone. The above is also reacted in a molar ratio of IPDI:macrodiols:DMPA of 3.76:1:1 (Table 3) or 3.52:1:1 (para 51), which meets claim 13. The above is biocompatible/biodegradable and used as scaffold for vascular grafts. (para 15-16).
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claim 14 is/are rejected under 35 U.S.C. 103 as being unpatentable over Sun and/or Hsu, as applied to claim 13 above, and further in view of US 6,087,465 A to Seppala et al. (hereinafter Seppala).
Regarding 14, as cited above and incorporated herein, Sun teaches claim 13.
Sun and/or Hsu, does not explicitly teach monitoring the isocyanate groups by FT-IR.
However, Seppela teaches a poly(esterurethane) and preparation thereof, used in the field of biodegradable polymers (See abstract) and coatings for medicines (claim 30), wherein the polyurethane is obtained from polymerizing a poly(lactic) acid prepolymer with a diisocyanate for a time wherein all the free end groups have reacted with the diisocyanate (col 1, ln 57 to col 2, ln 5). This is in the same field of use of biodegradable polyurethanes using similar and compatible components as the Applicant’s invention. Seppela further teaches IR spectrometry is well suited to monitor the amount of isocyanate and reaction progress because NCO-groups have a characteristic peak at 2270 cm-1, (col 8, ln 10-16), and that monitoring the reaction progress will enable control and determination of the molar mass distribution and average molecular weight. (col 7, ln 47 to col 8, ln 9).
It would have been obvious to one ordinarily skilled in the art before the effective filing date to monitor the isocyanate groups using IR spectrometry cited in Seppala to monitor the reaction of Sun because Seppala teaches the same field of use of biodegradable polyurethanes using similar and compatible components as the Applicant’s invention, and Seppela further teaches IR spectrometry is well suited to monitor the amount of isocyanate and reaction progress because NCO-groups have a characteristic peak at 2270 cm-1, (col 8, ln 10-16), and that monitoring the reaction progress will enable control and determination of the molar mass distribution and average molecular weight. (col 7, ln 47 to col 8, ln 9).
Claim 15 is/are rejected under 35 U.S.C. 103 as being unpatentable over Sun and/or Hsu, as applied to claim 13 above, and further in view of US 2009/0099600 A1 to Moore et al. (hereinafter Moore).
Regarding claim 15, as cited above and incorporated herein, Sun teaches claim 13.
Sun and/or Hsu does not explicitly teach wherein C comprises two or more different diol compounds at different lengths cited in claim 15.
However, Moore teaches a polyurethane used in the field of biomedical and biodegradable devices (See abstract and para 2-3), wherein the polyurethane is obtained from diisocyanates, polyols, and one or more chain extenders (para 23), wherein the diisocyanate can be hexamethylene diisocyanate (para 42), the polyol can contain segments of caprolactone and lactic acid (para 51), and the chain extenders include convention chain extenders such as butanediol (para 55). The above is in the same field of use of biomedical polyurethanes using similar and compatible components as the Applicant’s invention. Moore further teaches the chain extenders further include ester diols used in combination with conventional extenders (para 58), wherein the ester diols have the formula
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, wherein R1 and R2 are independently C1-C20 alkylene (para 59), such as
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, (para 60), which qualify as diols with different chain lengths cited in claim 15. Moore further teaches the above ester diols can be used in combination with conventional extenders to produce polyurethanes that degrade at faster rates. (para 58).
It would have been obvious to one ordinarily skilled in the art before the effective filing date to further include the
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chain extender of Moore in combination with the chain extender of Sun and/or Hsu because Moore teaches the same field of use of biomedical polyurethanes using similar and compatible components as the Applicant’s invention, and Moore further teaches the above ester diols can be used in combination with conventional extenders to produce polyurethanes that degrade at faster rates. (para 58).
Allowable Subject Matter
Claim 19 is allowed.
The following is an examiner’s statement of reasons for allowance:
The above prior art do not teach the claimed combination of B-C-B of claim 19.
Any comments considered necessary by applicant must be submitted no later than the payment of the issue fee and, to avoid processing delays, should preferably accompany the issue fee. Such submissions should be clearly labeled “Comments on Statement of Reasons for Allowance.”
Response to Arguments
Applicant's arguments filed 03/09/2026 have been fully considered but they are not persuasive in part.
On page 9-12, the Applicant argues that Shinozawa, and Sun, do not teach wherein (A-B-C-B) is NOT wherein B is HDI and C is BDO, B is IPDI and C is glycol, HDO, or DDO, or B is BDI and C is ODO.
In regard to Shinozawa, on page 10, the Applicant argues that Shinozawa teaches only a 1:1 molar ratio reaction of polyol A to HDI and a 1:2 ratio is needed t form the B-A-B portion of the polyurethane. This is found not persuasive because in Table 2 of Shinozawa, Example 7 shows an A:B molar ratio of about 0.023:0.048 (83.9/3600):(8.2/168.2), i.e. about 1:2, and is then further chain extended with DMPA, which would result in the claimed (A-B-C-B) with polyol A for A, HDI for B and DMPA for C.
In regard to Sun, on page 11, the Applicant argues that Sun teaches that the IPDI is reacted with the polymer until the NCO content meets a theoretical content of 10%, and states that this means 90% of the NCO groups have reacted and thus, would not result in a B-A-B segment since at least 50% of NCO groups must remain unreacted. This is not persuasive because the term “NCO content,” also known as %NCO, is the mass percentage of reactive NCO groups present in a material. In this case, Sun is teaching the reaction to be performed until the prepolymer reaches a NCO content of 10%. Sun further teaches that the polyol has a Mw range of 1000 to 10000 (page 1-2). If there is 100 g of polyol (MW 1000), i.e. 0.1 mol, reacted with 2 mols of IPDI (MW of 222 g/mol and 111 g/NCO eq), which correlates to 44.4 g of IPDI, wherein 22.2 g of it is NCO groups. This correlates to a NCO content of about 7%, and if there is a 10% NCO content, this leads to the conclusion that an excess molar ratio of IPDI is reacted with the polyol and would thus lead to both end groups of A being reacted with and a formula of B-A-B.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to HA S NGUYEN whose telephone number is (571)270-7395. The examiner can normally be reached Mon-Fri, Flex schedule 7:30am-4:00pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Randy Gulakowski can be reached at (571)272-1302. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/HA S NGUYEN/Primary Examiner, Art Unit 1766
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