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 .
Claims 1-18 are pending as amended on 2/2/2026.
Election/Restrictions
Applicant’s election without traverse of species ii, wherein the polymer is derived from a compound according to instant Formula XXIVb, and wherein R1 is H, Y is N(H) in the first instance and O in the second instance, and Q is linear C1-C6 alkyl, in the reply filed on 2/2/026 is acknowledged. [The elected species encompasses polymers comprising recurring units derived from the compounds synthesized in examples 1 and 2 of the instant specification:
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.]
Claims 10-15 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected species, there being no allowable generic or linking claim.
Claim Rejections - 35 USC § 103
Claims 1-9 and 16-18 is/are rejected under 35 U.S.C. 103 as being unpatentable over Aridomi et al (WO 2013/015121; English language equivalent US 2014/0134540 is cited herein) in view of Tabata et al (US 2005/0287655).
As to claims 1-9 and 16-18 and the elected species:
Aridomi discloses a polyurethane or polyester obtained by reacting a diol of formula (I) (copied below) with a polyisocyanate or polycarboxylic acid [0012]:
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wherein “B” is a monovalent organic group including at least one functional group. Aridomi names several functional groups, including “a hydroxyl group” [0017, 0064]. A polymer formed from reaction of Aridomi’s compound of formula (I) with a polyfunctional comonomer (polyisocyanate or polycarboxylic acid) has recurring units derived from the compound of formula (I) above.
Aridomi discloses that the diol compound of formula (I) is obtained by reacting a compound of formula (1) with a compound of formula (2) [0052-3]:
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Examples of compounds represented by formula (1) taught by Aridomi include mevalonolactone [0061]:
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Aridomi further discloses examples of compounds according to formula (2) in [0087], including several compounds wherein “B-NH2” comprises a linear alkylene group with the NH2 at one terminal of the alkylene, and a functional group taught in [0064] at the other terminal of the alkylene. See, e.g.:
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Aridomi teaches an example of a compound according to formula (I) having the structure (a)-5 [0091]:
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The reactant compounds of formulas (1) and (2) disclosed by Aridomi which result in a diol having a structure according to (a)-5 are (1)-5 in [0061] (mevalonolactone) and (2)-6 in [0087] (copied below):
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The compound of (a)-5 taught by Aridomi differs from the instant elected species of formula XXIVb because the instant species has hydroxyl (OH) as a functional group where Aridomi’s (a)-5 has carboxyl (CO2H) as a functional group. Aridomi fails to exemplify a reactant according to “B-NH2” which comprises hydroxyl (i.e., OH), as named in [0064], as the functional group at the terminal of the alkylene group opposite the NH2 group.
However, given that hydroxyl is named by Aridomi in [0064] along with types of functional groups shown in the compound examples in [0087], one having ordinary skill in the art would have at least envisaged a hydroxy-functional reactant compound according to Aridomi’s B-NH2 which is analogous to those shown in [0087], i.e., comprising a linear alkylene group with the NH2 at one terminal of the alkylene, and a hydroxy (OH) functional group as named in [0064] at the other terminal of the alkylene. When forming a compound according to Aridomi’s formula (I), the person having ordinary skill in the art would have been motivated to utilize a compound according to Aridomi’s formula 2 containing any appropriate kind of functional group named by Aridomi in [0064] in order to impart a desired kind of functionality to the ultimately obtained polyurethane. It would have been obvious to the person having ordinary skill in the art, therefore, to have formed polymer derived from a compound analogous to Aridomi’s compound of formula (a)-5:
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by substituting the carboxyl (CO2H) group (the group shown circled above) for any other type of functional group named by Aridomi, including a hydroxyl (OH) group in order to impart OH functionality to the obtained polymer. A compound analogous to formula (a)-5 wherein the (CO2H) group has been substituted for a hydroxyl (OH) group has a structure according to instant formula XXIVb, wherein R1 is H, R2 is a C1 alkyl, the internal Y is N(H), the terminal Y is O, and Q is an unsubstituted hydrocarbylene (i.e., a linear C2 alkylene).
As to the recitation that the polymer is biobased and derived from a ring-opened biobased mevalonolactone:
Aridomi suggests a compound which is derived from mevalonolactone, as set forth above. However, Aridomi fails to specifically teach utilizing “biobased” mevalonolactone.
Tabata teaches that mevalonic acid can be efficiently biosynthesized from a microorganism utilizing carbon sources such as glucose (abstract), [0108], [0153]. Tabata teaches that previously reported methods of producing naturally occurring mevalonic acid required a long cultivation time and the yield from the sugar was low [0005]. The method disclosed by Tabata is an extremely efficient process for producing mevalonic acid from an inexpensive raw material [0006-7, 0178]. Tabata further teaches that the acid form and lactone form can be converted to each other [0003].
When preparing a polymer from a compound derived from mevalonolactone, as disclosed by Aridomi, the person having ordinary skill in the art would have been motivated to source or prepare bioderived starting materials in order to utilize inexpensive raw materials, to decrease reliance on non-renewable resources (fossil feedstocks) and decrease environmental impact. It would have been obvious to the person having ordinary skill in the art, therefore, to have prepared a polymer from a mevalonolactone-derived compound, as suggested by Aridomi, utilizing biobased mevalonolactone (such as taught by Tabata) as the starting reactant compound (1)-5 (including starting material derived mostly or entirely from biobased sources),
thereby arriving at a biobased polymer according to claims 1-9 and 16-18 (including polymer wherein the starting material has a biobased content within the ranges recited in claims 6-9).
Alternatively, as to embodiments encompassed by claims 1, 3-9, 16 and 17 wherein Y can be -N(R3):
Modified Aridomi suggests a biobased polymer, as set forth above. As discussed above, Aridomi teaches that in the reactant of formula (2), desired functionality is easily imparted to the polyurethane by using an organic group containing a functional group as the monovalent organic group represented by B [0055]. Aridomi teaches several preferred examples of functional groups, including amino [0064], and teaches that examples of preferred amino groups include N-alkylamino and N,N-dialkylamino groups [0078]. Aridomi specifically names the following reactant of formula 2 which contains an N,N-dialkylamino group (i.e., dimethylamino):
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[0087].
Aridomi fails to specifically name a reactant of formula 2 which contains an N-alkylamino group rather than an N,N-dialkylamino group. However, given Aridomi’s teaching in [0078] that preferred amino groups include both N-alkylamino and N,N-dialkylamino groups, and given that Aridomi specifically teaches methylamino and ethylamino as preferred amino groups [0078], the person having ordinary skill in the art would have been motivated to substitute the N,N-dialkylamino group in Aridomi’s reactant of formula (2)-17 for an N-alkylamino group named by Aridomi, including methylamino or ethylamino, in order to provide the corresponding specific functionality to the ultimately obtained polyurethane, depending on the intended application. The resulting methylamino or ethylamino-containing reactant would have one of the following structures, as drawn by the examiner:
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It would have been obvious to the person having ordinary skill in the art, therefore, to have prepared a biobased polyurethane from biosynthesized mevalonolactone of formula (1)-5 and a reactant of formula (2) (i.e., B-NH2), as suggested by modified Aridomi, utilizing a formula (2) reactant having any type of functionality named by Aridomi, including a methylamino or ethylamino-containing reactant as shown above.
The diol resulting from the reaction of (1)-5 with the above methylamino-group-containing reactant as formula (2) has a structure shown below (as drawn by the examiner):
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, which corresponds to instant formula XXIVb, wherein R1 is H, R2 is a C1 alkyl, the internal Y is N(H), the terminal Y is N(R3) where R3 is C1 alkyl, and Q is a linear hydrocarbyl (i.e., a C2 alkylene group).
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to RACHEL KAHN whose telephone number is (571)270-7346. The examiner can normally be reached Monday to Friday, 8-5.
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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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/RACHEL KAHN/Primary Examiner, Art Unit 1766
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