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 .
Claim Rejections – 35 Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
Claim(s) 1-10 and 12-16 is/are rejected under 35 U.S.C. 103 as obvious over Kakinuma et al (US 2022/0275125).
Kakinuma sets forth urethane allyl compounds, monomer compositions comprising the same, as well as, molded bodies and dental materials comprising said compositions—see title.
Kakinuma sets forth obtaining a urethane allyl (meth)acrylate compound (Y) which is a reaction product of an iso(thio)cyanate compound (A) having two or more iso(thio)cyanate groups, an alcohol compound (B) having an allyloxy group, and an alcohol compound (C) having a (meth)acryloyloxy group in the presence of a urethanization catalyst—see [0010] and [0156]. Said urethanization catalyst organic compounds of metals other than tin such as copper naphthenate, cobalt naphthenate, zinc naphthenate, acetylacetonatozirconium, acetylacetonatoiron, and acetylacetonatogermanium; amine compounds and salts thereof such as triethylamine, 1,4-diazabicyclo[2.2.2]octane, 2,6,7-trimethyl-1-diazabicyclo[2.2.2]octane, 1,8-diazabicyclo[5.4.0]undecene, N,N-dimethylcyclohexylamine, pyridine, N-methylmorpholine, N,N,N′,N′-tetramethylethylenediamine, N,N,N′,N′-tetramethyl-1,3-butanediamine, N,N,N′,N′-pentamethyldiethylenetriamine, N,N,N′,N′-tetra(3-dimethylaminopropyl)-methanediamine, N,N′-dimethylpiperazine, and 1,2-dimethylimidazole; and trialkylphosphine compounds such as tri-n-butylphosphine, tri-n-hexylphosphine, tricyclohexylphosphine, and tri-n-octylphosphine—see [0097] and [0192].
Regarding claims 1-5 and 16: Kakinuma does not expressly set forth obtaining urethane allyl (meth)acrylate compound (Y) in the presence of a tin-free catalyst. However, in the overall teachings of the reference it is set forth urethanization catalyst such as, acetylacetonatozirconium, which is a tin-free catalyst represented by general formula (Y) in claim 3 having a diketone structure (claim 2), when MY is zirconium a group 4 metal compound can be used (claim 4), wherein the obtain compound having formula (Y1) [0015] appears to be free of carboxylic acid amide and sulfonamide groups (claim 1). Therefore, it is deemed it would have been within the skill level of an ordinary artisan, using the overall teachings of the reference, to obtain said urethane allyl (meth)acrylate compound (Y) which is a reaction product of an iso(thio)cyanate compound (A) having two or more iso(thio)cyanate groups, an alcohol compound (B) having an allyloxy group, and an alcohol compound (C) having a (meth)acryloyloxy group in the presence of a tin-free urethanization catalyst, such as acetylacetonatozirconium, with a reasonable expectation of success in absence of evidence to the contrary and/or unexpected results.
Regarding claims 6-7: Kakinuma sets forth said a urethane allyl (meth)acrylate compound (Y) which is a reaction product of an iso(thio)cyanate compound (A) having two or more iso(thio)cyanate groups, an alcohol compound (B) having an allyloxy group, and an alcohol compound (C) having a (meth)acryloyloxy group, wherein the thioisocyanate compounds can be selected from aromatic polythioisocyanate compounds, such as tolylene diisothiocyanate, 4,4-diphenylmethane diisothiocyanate, and diphenyl sulfide-4,4-diisothiocyanate; sulfur-containing heterocyclic polyi sothiocyanate compounds such as 2,5-diisothiocyanate thiophene, 2, 5-bis(i sothiocyanato methyl)thiophene, 2,5-i sothiocyanate tetrahydrothiophene, 2,5-bis(i sothiocyanato methyl)tetrahydrothiophene, 3 ,4-bis(i sothiocyanato methyl)tetrahydrothiophene, 2,5-diisothiocyanate -1,4-dithiane, 2,5-bis(i sothiocyanato methyl)-1,4-dithiane, 4,5-diisothiocyanate-1,3-dithiolane, and 4,5-bis(i sothiocyanato methyl)-1,3-dithiolane—see [0077]. Thus, claim 7 is found in the reference. It would have been within the skill level of an ordinary artisan, using the overall teachings, to obtain a urethane allyl (meth)acrylate having formula (Y1) having aromatic rings in absence of evidence to the contrary and/or unexpected results.
Regarding claim 8: Kakinuma sets forth obtaining a urethane allyl compound (X) is a reaction product of an iso(thio)cyanate compound (A) having two or more iso(thio)cyanate groups and an alcohol compound (B) having an allyloxy group, which is the reaction product of s a reaction product of an iso(thio)cyanate compound (A) having two or more iso(thio)cyanate groups and an alcohol compound (B) having an allyloxy group—see [0011]. It is taught The iso(thio)cyanate compound (A) is a compound having two or more iso(thio)cyanate groups, and is preferably a compound in which A iso(thio)cyanate groups are bonded to an A-valent linking group, such as -xylyl ene diisocyanate, 1,3-tetramethylxylylene diisocyanate, tolylene diisocyanate, phenylene diisocyanate, and 4,4′-diphenylmethane diisocyanate— [see 0076]. Thus, claim 8 is found in the reference. It would have been within the skill level of an ordinary artisan, using the overall teachings, to obtain a urethane allyl (meth)acrylate having formula (X) using polyisocyanate compounds, such as -xylyl ene diisocyanate, 1,3-tetramethylxylylene diisocyanate, tolylene diisocyanate, phenylene diisocyanate, and 4,4′-diphenylmethane diisocyanate, in absence of evidence to the contrary and/or unexpected results.
Regarding 9: Kakinuma sets forth the alcohol compound (C) having a (meth)acryloyloxy group can be chosen from 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, and 1,4-cyclohexanedimethanol mono(meth)acrylate—see [0014] and [0180-0181].
Regarding claim 10: Kakinuma sets forth a polymerization inhibitor (stabilization from unwanted polymerization) an be added to the reactions of the allyl urethane compounds (X1) and (Y1), such as dibutyl hydroxytoluene, hydroquinone, hydroquinone monomethyl ether, and phenothiazine, wherein at least one comprises a phenolic moiety—see [0101]. It would have been within the skill level of an ordinary artisan, using the overall teachings, to obtain a urethane allyl (meth)acrylate having formula (X1) and (Y1) in the presence of a phenolic polymerization inhibitor (stabilizer from uncontrolled/unwanted polymerization) in absence of evidence to the contrary and/or unexpected results.
Regarding claims 12-16: Kakinuma sets forth a monomer composition [claim 16] comprising the above-described allyl urethane of formula (X1) and/or (Y1) and a monomer compound and a polymerization initiator [claim 13]—see [0103-0104] and [0111] and [0113]. Said monomer composition is used to form molded bodies [0108, claim 15] and dental composition [0110, claim 14-15].
Claims 1-2 and 6-16 is/are rejected under 35 U.S.C. 103 as being obvious over Kakinuma et al (Kakinuma 2) (US2021/024623) in view of Kakinuma (cited above, Kakinuma 1).
Kakinuma 2 sets forth a (meth)acrylate composition (meth)acrylate includes a reaction product of a thiol compound containing two or more thiol groups, and a (meth)acrylate compound containing two or more (meth)acryloyloxy group—see abstract, wherein said composition are used for dental materials and/or molded bodies—see abstract.
Said monomer composition for a dental material comprising a reaction product of a thiol compound (1) containing two or more thiol groups, and a (meth)acrylate compound (2) containing two or more (meth)acryloyloxy group and the molded body comprises a cured product of the monomer composition for a dental material— [0009] and [0019]. Said monomer has the general formula:
PNG
media_image1.png
95
289
media_image1.png
Greyscale
--see [0022].
Kakinuma 2 sets forth a monomer composition comprising a (A) the (meth)acrylate as described above, and a (meth)acrylate (B) containing a (meth)acrylate that is the reaction product of the thiol compound (1) containing three or more thiol groups, an iso(thio)cyanate compound (3) containing two or more iso(thio)cyanate groups, and a (meth)acrylate compound (4) containing a (meth)acryloyloxy group and containing a hydroxy group—see [0149] to [0151]. Said methacrylate monomer (B) has the general formula:
PNG
media_image2.png
80
291
media_image2.png
Greyscale
, X can be O, thus free of carboxylic amide and sulfonamide groups--see [0032]. Said isocyanate compounds can be selected from aromatic polyisocyanate compounds such as phenylenediocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 4,4′-diphenylmethane diisocyanate, and diphenyl sulfide-4,4-diisocyanate; and heterocyclic polyisocyanate compounds such as 2,5-diisocyanatothiophene, 2,5-bis(isocyanatomethyl)thiophene, 2,5-diisocyanatotetrahydrothiophene, 2,5-bis(isocyanatomethyl)tetrahydrothiophene, 3,4-bis(isocyanatomethyl)tetrahydrothiophene, 2,5-diisocyanato-1,4-dithiane, 2,5-bis(isocyanatomethyl)-1,4-dithiane, 4,5-diisocyanato-1,3-dithiolane, and 4, 5-bis(isocyanatomethyl)-1,3 dithiolane—see [0151].
Regarding claims 1-2 and 6-11: Said (meth) acrylate (B) is be obtained by reacting the thiol compound (1), the iso(thio)cyanate compound (3), and the (meth)acrylate compound (4), and this reaction can be carried in the presence of alkylphosphine compounds as catalyst, wherein (B) has the general formula described above; and meth)acrylate compound (4) include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and 1, 4-cyclohexanedimethanol mono(meth)acrylate.—see [0032], [0153], [0163] and [0157].
Regarding claim 1-11 and 16: Kakinuma 2 sets forth a manufacturing method for obtaining a thiourethane acrylate comprising adding m-xylylene diisocyanate and a mixture of comprising 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane (thiol); 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane (thiol) and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane (thiol) and hydroxypropyl acrylate in the presence of a urethanization catalyst (DBTDL) and a polymerization inhibitor (BHT, stabilizes the polymerization reaction) to obtain a thiourethane acrylate having a viscosity at 65° C. of 1790 mPa*s and a refractive index at 25° C. of 1.5271, said urethane appears to be free of carboxyl amide and sulfonamide groups.
The primary difference is the method sets forth a tin catalyst; however, it is known that urethane (meth) acrylates can be obtained by catalyst other than tin-containing catalyst, as set forth by Kakinuma 1. Kakinuma 1 sets forth obtaining a urethane allyl (meth)acrylate compound (Y) which is a reaction product of an iso(thio)cyanate compound (A) having two or more iso(thio)cyanate groups, an alcohol compound (B) having an allyloxy group, and an alcohol compound (C) having a (meth)acryloyloxy group in the presence of a urethanization catalyst—see [0010] and [0156]. Said urethanization catalyst can be an organic compound of metals other than tin such as copper naphthenate, cobalt naphthenate, zinc naphthenate, acetylacetonatozirconium, acetylacetonatoiron, and acetylacetonatogermanium; amine compounds and salts thereof such as triethylamine, 1,4-diazabicyclo[2.2.2]octane, 2,6,7-trimethyl-1-diazabicyclo[2.2.2]octane, 1,8-diazabicyclo[5.4.0]undecene, N,N-dimethylcyclohexylamine, pyridine, N-methylmorpholine, N,N,N′,N′-tetramethylethylenediamine, N,N,N′,N′-tetramethyl-1,3-butanediamine, N,N,N′,N′-pentamethyldiethylenetriamine, N,N,N′,N′-tetra(3-dimethylaminopropyl)-methanediamine, N,N′-dimethylpiperazine, and 1,2-dimethylimidazole; and trialkylphosphine compounds such as tri-n-butylphosphine, tri-n-hexylphosphine, tricyclohexylphosphine, and tri-n-octylphosphine—see [0097] and [0192]. Kakinuma 1 and 2 are analogous art since they are from the same field of endeavor, that is the art of urethane (meth) acrylate monomers from iso(thio) cyanates. Therefore, it is deemed it would have been within the skill level of an ordinary artisan, using the overall teachings of the reference Kakinuma 2, to obtain said urethane (meth)acrylate compound that is the reaction product of an iso(thio)cyanate compound (A) having two or more iso(thio)cyanate groups and an alcohol compound (C) having a (meth)acryloyloxy group in the presence of a tin-free urethanization catalyst, such as acetylacetonatozirconium, with a reasonable expectation of success in absence of evidence to the contrary and/or unexpected results.
Regarding claims 10: The reaction product to obtain the hydroxy-modified acrylate in production example 1 is polymerized in the presence of a phenolic polymerization inhibitor (polymerization stabilizer for unwanted polymerization), i.e., BHT (butylhydroxytoluene).
Regarding claims 12-14: Kakinuma sets forth a method of manufacturing a composition for a dental material (claim 12, 14) comprising a step of preparing the (meth)acrylate (A); a step of producing said composition for a dental material (claim 12, 14) by mixing the (meth)acrylate (A), the (meth)acrylate (B), the polymerization initiator (claim 13), and the filler—see [0210].
Regarding claim 15: Kakinuma sets forth molded bodies comprising a cured product of the monomer composition for a dental material as described above, by curing the monomer composition containing the (meth)acrylate (A) and the (meth)acrylate (B), wherein the cured product having excellent heat resistance, solvent resistance and impact resistance—see [0181].
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SANZA L MCCLENDON whose telephone number is (571)272-1074. The examiner can normally be reached 8-5.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Heidi Riviere-Kelley can be reached at 571-270-1831. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/SANZA L. McCLENDON/Primary Examiner, Art Unit 1765
SMc
Prosecution Insights