DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Any new grounds of rejection set forth below are necessitated by Applicant’s amendment. For this reason, the present action is properly made final.
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office Action.
Claims 1-7, 9-11 and 13-22 are pending.
Claim Rejections - 35 USC § 103
Claims 1-3, 9-11, 17-19, 21 are rejected under 35 U.S.C. 103 as being unpatentable over Tetsuya et al. (JP 2008/280382) in view of Hayes et al. (US 6,077,886).
Regarding claim 1: Tetsuya is directed to a process of controlling rheology of a liquid preparation, the process comprising:
Adding a silicate to the preparation, and
Adding a reaction product (B) to the preparation, the reaction product (B) obtained by reacting a polyethylenimine, with at least one compound having with at least one compound having at least one epoxide group (abstract).
While the structure is not recited, Denatured imine 1 comprises the reaction product of polyethyleneimine and AED-9, which is an alkyl C12-C13 glycidyl ether, which is the same reaction of the present invention, and therefore there is a reasonable basis to conclude the resulting reaction product has the structure (I) of the present invention, wherein R1 is H, and one of R2 of R3 is H and one of R2 or R3 is an organic group.
Epomin SP-200 is utilized in the working examples, having a molecular weight of 10,000.
Hayes is directed to an epoxy composition comprising an epoxy resin, a thixotropic agent of a silicate, and a polyethyleneimine having a Mw of 700 – 1,000,000, preferably 25,000-750,000 (col. 3 ll. 3-10 Hayes). One skilled in the art would have selected the Mw of Hayes as the polyethyleneimine of choice in Tetsuya for improved non-slump performance under normal storage conditions, and improved slump resistance over 1-2 days under elevated storage temperatures (100 ˚C) vs other epoxy hardeners (col. 11 ll. 35-43 and Table III) Hayes). Therefore, it would have been obvious to one skilled in the art at the time the invention was filed to have selected a polyethyleneimine having a Mw within the scope of claim 1.
Regarding claim 3: R2 and R3 can include hydrocarbyl groups. For instance, Denatured imine 1 comprises the reaction product of polyethyleneimine and AED-9, which is an alkyl C12-C13 glycidyl ether, which is equivalent to R3 of an organic groups comprising an ether group.
Regarding claim 9: The composition does not comprise water, and is therefore non-aqueous.
Regarding claim 10: Tetsuya doesn’t mention an amount of product (B).
Hayes teaches preferably, the amount of polyethyleneimine is such that the epoxy resin composition does not flow for at least 60 minutes after formation thereof (col. 3 ll. 10-16 Hayes). Therefore, the amount of reaction product (B) is a result-effective variable (MPEP 2144.05) since the amount used results in a particular flow after 60 minutes. In other words, the amount is a matter of routine experimentation and would have been well within the skill level of, and thus obvious to, one of ordinary skill in the art. Therefore, it would have been obvious to one skilled in the art at the time the invention was filed to have selected an amount of reaction product (B) within the scope of claim 10.
Regarding claim 11: An epoxy resin is disclosed.
Regarding claim 17: Tetsuya doesn’t mention when the silicate is added relative to the reaction product (B).
Hayes teaches the liquid epoxy resin is added to fumed silica and later a polyethyleneimine is added as a hardener. One skilled in the art would have been motivated to have added the silicate (A) to the epoxy resin before adding the reaction product (B) in … since the reaction product (B) is a hardener. Therefore, it would have been obvious to one skilled in the art at the time the invention was filed to have added the silicate (A) to the epoxy resin before adding the reaction product (B).
Regarding claim 18: The combination of Tetsuya and Hayes doesn’t mention adding the reaction product (B) to the preparation before adding the silicate (A) to the preparation. However, case law holds that selection of any order of mixing ingredients is prima facia obvious. In re Gibson, 39 F.2d 975, 5 USPQ 230 (CCPA 1930) (Selection of any order of mixing ingredients is prima facie obvious.). MPEP 2144.04 (IV)(C).
Regarding claim 19: The process comprises adding the composition to the preparation. Specifically, the silicate and reaction product (B) used to cure epoxy resins.
Regarding claim 21: The working examples comprise a molar ratio of total amine groups of the polyethylenimine and epoxide groups of the compound having at least one epoxide group between 100.0:10.0 and 100.0:4.0. Specifically, Imine 1 comprises 100 part by weight Epomin SP-200 having an amine value of 18 mmol/g and 50 part by weight AEP having an epoxy group content of 3.0–3.7 mmol/g. It follows the molar ratio of total amine groups to epoxy groups is about 12:1.
Claims 4, 20, 22 are rejected under 35 U.S.C. 103 as being unpatentable over Tetsuya and Hayes as applied to claim 1 above, and further in view of Piaster et al. (US 2017/0226313).
Regarding claim 2: Tetsuya doesn’t mention the silicate comprises clay.
Piestert discloses the inorganic thickener comprises a mixture of organically modified clay and silicate ([0048]-[0049] Piestert). One skilled in the art would have been motivated to have selected a mixture of organically modified clay and silica as the silica powder of choice in Tetsuya since they are preferred ([0049]), and enhance the mechanical properties of the cured system ([0022] Piestert). Therefore, it would have been obvious to one skilled in the art at the time the invention was filed to have selected a mixture of organically modified clay and silica as the silica powder of choice in Tetsuya to arrive at claim 2 of the present invention.
Regarding claim 4: Tetsuya doesn’t mention the reaction product (B) comprises a salt.
Piestert is directed to an epoxy resin composition comprising an epoxy resin, a silicate inorganic thickener ([0046]) and a dispersing agent (a2) comprising the reaction product of a polyamine of the formula H2-(C2H4NH)n-C2H4-NH2 n>5 (polyethylenimine, PEI) and the salification thereof with an phosphoric ester or sulfonic acid , or carboxylic acid ([0062]-[0063] Piestert). One skilled in the art would have been motivated to have included a carboxylic, phosphoric acid, or sulfonic acid salt salification reaction product (B) in Tetsuya since it displays particularly good effects in the dispersions [0063] Piestert). Therefore, it would have been obvious to one skilled in the art to have included a carboxylic, phosphoric acid, or sulfonic acid salt in the reaction product (B) of Tetsuya.
Regarding claim 20: Tetsuya doesn’t mention the silicate comprises clay.
Piestert discloses the inorganic thickener comprises a mixture of clay and silicate ([0049] Piestert). One skilled in the art would have been motivated to have selected a mixture of clay and silica as the silica powder of choice in Tetsuya since they are preferred ([0049]), and enhance the mechanical properties of the cured system ([0022] Piestert). Therefore, it would have been obvious to one skilled in the art at the time the invention was filed to have selected the silica powder of choice in Tetsuya since they are preferred ([0049]), and enhance the mechanical properties of the cured system ([0022] Piestert).
Regarding claim 22: Tetsuya doesn’t mention a binder of claim 22.
Piestert teaches the composition can comprise polymers of polyurethane resins and polyacrylates ([0059] Piestert). While Piestert characterizes these resins as wetting and dispersing agents, the of polyurethane resins and polyacrylates are the same as those recited in present claim 22, and would therefore one skilled in the art would expect to perform the function of a binder. One skilled in the art would have been motivated to have included a polyurethane resins and polyacrylates in the composition of Tetsuya for wetting and dispersing properties. Therefore, it would have been obvious to one skilled in the art at the time the invention was filed to have included a resin of claim 22 in the composition of Tetsuya.
Claims 5-7 are rejected under 35 U.S.C. 103 as being unpatentable over Tetsuya and Hayes as applied to claim 1 above, and further in view of Gobalt et al. (US 2017/0190840).
Regarding claim 5: Tetsuya doesn’t mention any solvents beyond benzyl alcohol utilized in the working examples.
Goblet is directed to polyamine addition products including PEI and epoxide groups. The solvent utilized includes those defined by the present invention as a high boiling solvent of at least 250 C at 100 kPa including dipropylene glycol dimethyl ether. One skilled in the art would have been motivated to have selected a high boiling solvent including dipropylene glycol dimethyl ether since the reaction products are soluble and the solvent is unreactive ([0141] Gobelt). Therefore, it would have been obvious to one skilled in the art at the time the invention was filed to have selected a solvent a high boiling solvent of at least 250 C at 100 kPa including dipropylene glycol dimethyl ether.
Regarding claim 6: The reaction is at room temperature and is a liquid at 23 C and at 100 kPa (approximately room temperature).
Regarding claim 7: Suitable solvents include dipropylene glycol dimethyl ether.
Response to Arguments
Applicant's arguments filed 1/8/2026 (herein “Remarks”) have been fully considered but they are not persuasive.
Applicant argues (p. 7-8 Remarks) Tetsuya teaches thixotropic expression increases as molecular weight increases, and is maintained when the polyalkyleneimine is modified with a compound having an epoxy group. Based on Tetsuya, one skilled in the art would expect epoxy compositions including the modified polyethyleneimine would have the same sag resistance (thixotropic effect). However, Examples 9.1-9.10 demonstrate unexpected results. Example 9.8 has an unmodified polyethyleneimine having a molecular weight of 196,844. Example 9.4 contains the same polyethyleneimine although reacted with an epoxy compound and has double the sag resistance compared to 9.8. Examples 9.9, 9.10, and 9.4 demonstrate the claimed molecular weight of polyethyleneimines is critical to sag resistance. Examples 9.3-9.7 demonstrate sag resistance is again dependent on the claimed range of molecular weight. The combination of Tetsuya and Hayes does not suggest the modification can result in sag resistance that is double that of the corresponding unmodified polyethyleneimine, nor that it is useful in other compositions.
The burden of showing unexpected results rests on the person who asserts them by establishing that the difference between the claimed invention and the closest prior art was an unexpected difference. See In re Klosak, 455 F.2d 1077, 1080 (CCPA 1972). Further, the showing of unexpected results must be commensurate in scope with the claims. See In re Peterson, 315 F.3d 1325, 1330-31 (Fed. Cir. 2003).
In the present case, IS1 is the reaction product of a linear C13-C15 alkyl Glycidylether and the polyamine, and therefore R2 or R3 is a specific organic group of a C13-C15 alkyl group. In contrast, the present claims include R2 or R3 include any organic group, which is much broader in scope. Likewise, the Examples utilize a silicate of an organically modified clay, while the claims include any silicate. Further, specific amounts of silicate and reaction product B are utilized in the Examples 9.1-9.10. In contrast, no amounts are recited in claim 1. While an amount is recited in claim 10, this is much broader in scope than Examples 9.1-9.10. Therefore, Examples 9.1-9.10 are not commensurate in scope with the present claims.
Applicant argues (p. 8-9 Remarks) Tetsuya discloses polyalkyleneimine (denatured imines 1-3) has a molecular weight of 20000. The weight taught by Tetsuya is not within the weight average molecular weight of 40000 to 300000 g/mol before reaction with the compound having an epoxy group. Hayes has been cited for teaching a polyethylenimine having a weight average molecular weight of 700 to 1,000,000. The improved performance in Hayes is of an unmodified polyethyleneimine of 750,000 compared to 25,000. Tetsuya teaches away from unmodified polyalkyleneimine having a high molecular weight stating “The thixotropic expression increases as the molecular weight of the polyalkyleneimine resin increase, but the compatibility with the resin is lost.” Because the teaching of Hayes relates to molecular weight of an unmodified polyethylenimine and Tetsuya teaches away from a high molecular weight unmodified polyethylenimine, Applicant believes Hayes fails to give adequate motivation to combine with Tetsuya.
This argument is not found persuasive since Epomin SP-200 is utilized in the working examples, having a molecular weight of 20,000, although a weight average molecular weight Mw is not otherwise mentioned. In other words, the specific molecular weight, number average or weight average, is not elucidated in Tetsuya, and therefore it is possible a weight average molecular weight of Tetsuya is within the claimed range. Further, while a “high molecular weight” is not preferred in Tetsuya, the value for a high molecular weight is not given or defined. Therefore, the rejection is maintained.
Applicant argues (p. 10 Remarks) new claim 21 requires a molar ratio of total amine groups of the polyethylenimine and epoxide groups is between 100.0 : 10.0 and 100.0 : 4.0.
This argument is not found persuasive for the following. The working examples comprise a molar ratio of total amine groups of the polyethylenimine and epoxide groups of the compound having at least one epoxide group between 100.0:10.0 and 100.0:4.0. Specifically, Imine 2 comprises 100 part by weight Epomin SP-200 having an amine value of 18 mmol/g and 50 part by weight Cardura E having an epoxy group content of 4100 mol/kg. It follows the molar ratio of total amine groups to epoxy groups is about 8.8.
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.
Contact Information
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ROBERT T BUTCHER whose telephone number is (571)270-3514. The examiner can normally be reached Telework M-F 9-5 Pacific Time Zone.
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/ROBERT T BUTCHER/Primary Examiner, Art Unit 1764