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 .
The response of the applicant has been read and given careful consideration. The election of group I, claims 1-6 and 10-17 is noted. Responses to the argument are presented below. The restriction is repeated and made final.
Restriction to one of the following inventions is required under 35 U.S.C. 121:
I. Claims 1-6 and 10-17, drawn to a polymerizable compound and composition containing it, classified in G03H1/02, G07F7/027, C08F20/38.
II. Claim 7, drawn to a hydroxy containing compound, classified in C07D417/14,
III. Claims 8 and 9, drawn to a process of synthesizing the hydroxy compound using a ring opening reaction, classified in C07D303/02.
The inventions are independent or distinct, each from the other because:
Inventions group II and group I are related as mutually exclusive species in an intermediate-final product relationship. Distinctness is proven for claims in this relationship if the intermediate product is useful to make other than the final product, and the species are patentably distinct (MPEP § 806.05(j)). In the instant case, the intermediate product is deemed to be useful as a precursor compound top synthesize non-polymerizable compounds and the inventions are deemed patentably distinct because there is nothing of record to show them to be obvious variants.
Inventions group III and group II are related as process of making and product made. The inventions are distinct if either or both of the following can be shown: (1) that the process as claimed can be used to make another and materially different product or (2) that the product as claimed can be made by another and materially different process (MPEP § 806.05(f)). In the instant case the hydroxy compound can be made using reactions not requiring ring opening step using a different precursor, where the hydroxy oxygen is protected by a leaving group which is not part of a ring.
Inventions group I and group III are unrelated. Inventions are unrelated if it can be shown that they are not disclosed as capable of use together and they have different designs, modes of operation, and effects (MPEP § 802.01 and § 806.06). In the instant case, the different inventions.
The process of group III is sued to make the precursor II, not the polymerizable compound of group I. The examiner also note that the synthesis of the polymerizable compound can be achieved without using the ring opening reaction of group III.
Restriction for examination purposes as indicated is proper because all the inventions listed in this action are independent or distinct for the reasons given above and there would be a serious search and/or examination burden if restriction were not required because one or more of the following reasons apply:
The different inventions have acquired a separate status in the art as shown by their different classification and their recognized divergent subject matter
Applicant is advised that the reply to this requirement to be complete must include (i) an election of an invention to be examined even though the requirement may be traversed (37 CFR 1.143) and (ii) identification of the claims encompassing the elected invention.
The election of an invention may be made with or without traverse. To reserve a right to petition, the election must be made with traverse. If the reply does not distinctly and specifically point out supposed errors in the restriction requirement, the election shall be treated as an election without traverse. Traversal must be presented at the time of election in order to be considered timely. Failure to timely traverse the requirement will result in the loss of right to petition under 37 CFR 1.144. If claims are added after the election, applicant must indicate which of these claims are readable upon the elected invention.
Should applicant traverse on the ground that the inventions are not patentably distinct, applicant should submit evidence or identify such evidence now of record showing the inventions to be obvious variants or clearly admit on the record that this is the case. In either instance, if the examiner finds one of the inventions unpatentable over the prior art, the evidence or admission may be used in a rejection under 35 U.S.C. 103 or pre-AIA 35 U.S.C. 103(a) of the other invention.
A telephone call was made to Yanhong HU (67095) on April 2, 2026 to request an oral election to the above restriction requirement, but did not result in an election being made.
Applicant is reminded that upon the cancelation of claims to a non-elected invention, the inventorship must be corrected in compliance with 37 CFR 1.48(a) if one or more of the currently named inventors is no longer an inventor of at least one claim remaining in the application. A request to correct inventorship under 37 CFR 1.48(a) must be accompanied by an application data sheet in accordance with 37 CFR 1.76 that identifies each inventor by his or her legal name and by the processing fee required under 37 CFR 1.17(i).
The examiner has required restriction between product or apparatus claims and process claims. Where applicant elects claims directed to the product/apparatus, and all product/apparatus claims are subsequently found allowable, withdrawn process claims that include all the limitations of the allowable product/apparatus claims should be considered for rejoinder. All claims directed to a nonelected process invention must include all the limitations of an allowable product/apparatus claim for that process invention to be rejoined.
In the event of rejoinder, the requirement for restriction between the product/apparatus claims and the rejoined process claims will be withdrawn, and the rejoined process claims will be fully examined for patentability in accordance with 37 CFR 1.104. Thus, to be allowable, the rejoined claims must meet all criteria for patentability including the requirements of 35 U.S.C. 101, 102, 103 and 112. Until all claims to the elected product/apparatus are found allowable, an otherwise proper restriction requirement between product/apparatus claims and process claims may be maintained. Withdrawn process claims that are not commensurate in scope with an allowable product/apparatus claim will not be rejoined. See MPEP § 821.04. Additionally, in order for rejoinder to occur, applicant is advised that the process claims should be amended during prosecution to require the limitations of the product/apparatus claims. Failure to do so may result in no rejoinder. Further, note that the prohibition against double patenting rejections of 35 U.S.C. 121 does not apply where the restriction requirement is withdrawn by the examiner before the patent issues. See MPEP § 804.01.
Applicant's election with traverse of group I in the reply filed on 6/3/2026 is acknowledged. The traversal is on the ground(s) that there is no search burden. This is not found persuasive because there is in fact a search burden as classes and subject matter relating to groups II and III would not have to be searched in the search of group I, which includes polymerizable monomers, photosensitive compositions including them, and holographic articles. The hydroxy compounds are not free radically polymerizable, so they do not overlap in scope with the (meth)acrylate monomers of group 1, and are not obvious variants of these as they have entirely different reactive functionality and have a different mode of use and function (one is free radically polymerizable and the hydroxy containing compound is not). The examiner stands by the statements of regarding the differences between groups I and III and II and III articulated in the original restriction. The examiner notes that [0042-0047] of 20060147702 teaches some methods of synthesizing the monomers
The requirement is still deemed proper and is therefore made FINAL.
Claims 7-9 are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention, there being no allowable generic or linking claim. Applicant timely traversed the restriction (election) requirement in the reply filed on 6/3/2026.
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
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.
Claims 1-5 are rejected under 35 U.S.C. 102(a)(1) as being fully anticipated by Shibata et al. JP 2021024842.
Shibata et al. JP 2021204842 (machine translation attached) exemplifies monomers (pages 10-11)
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in example 5, 20 parts of monomer 1A-1 was combined with 9,9-bis (4-acryloyloxyethoxyphenyl) fluorene (Shin-Nakamura Chemical Industry product name: NK ester A-BPEF) Parts by mass, 2 parts by mass of benzyl methacrylate (Mitsubishi Chemical product name: Acryester BZ), 20 parts by mass of trimethylpropantrimethacrylate, 0.5 parts by mass of IRGANOX 1076 (BASF product name) as an antioxidant, polymerization prohibited Add 0.05 part by mass of BHT (Honshu Kagaku Co., Ltd. product name: H-BHT) as an agent and 2 parts by mass of Irgacure 184 (BASF company product name) as a photopolymerization initiator, and stir at 70 ° C. for 2 hours. As a result, a curable resin raw material composition was obtained. The obtained curable resin raw material composition was sealed with two glass plates using a 1 mm thick silicone sheet as a gasket, and then photocured with a high-pressure mercury lamp (integrated light amount: 3,000 mJ / cm .sup.2 ). Further, after heating at 130 ° C. for 30 minutes, the glass plate was removed to obtain a polymer having a thickness of 1 mm [0127]. These monomers are bounded by the formula (1)
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In formula (1), Q .sup.1 , Q .sup.2 , Q .sup.3 , and Q .sup.4 independently represent alkylene groups having 1 to 6 carbon atoms. It may be linear or branched. The number of carbon atoms is preferably 1 to 4. A methylene group, an ethylene group, a methylmethylene group, and an ethylmethylene group are more preferable, a methylene group or an ethylene group is further preferable, and a methylene group is particularly preferable. .sup.Q 1 , Q .sup.2 , Q .sup.3 , and Q .sup.4 in one molecule may be the same or different from each other. And that the raw material is easily available, product in terms of easily controlling the stereoisomers .sup.of, Q 1, Q 2, Q 3, it is preferable Q .sup.4 are the same as each other. In formula (1), A .sup.1 and A .sup.2 each independently represent a polymerizable group. The polymerizable group is preferably a group containing a polymerizable carbon-carbon double bond or a group containing an alicyclic ether bond. Specific examples of the group containing a polymerizable carbon-carbon double bond include (meth) acryloyl group, vinyl group, vinyl-substituted phenyl group, isopropenyl-substituted phenyl group, vinyl-substituted naphthyl group, isopropenyl-substituted naphthyl group and the like. Be done. Specific examples of the group containing an alicyclic ether bond include an oxylanyl group, a 2-methyloxylanyl group, and an oxetanyl group. A (meth) acryloyl group is preferable because it is easy to obtain high transparency. .sup.A 1 and A .sup.2 in one molecule may be the same or different from each other. In the formula (1), Cy .sup.1 and Cy .sup.2 represent a sulfur-containing aromatic heterocycle which may have a substituent independently of each other. The sulfur-containing aromatic heterocycle contributes to a high refractive index. The sulfur-containing aromatic heterocycle may have a substituent. .sup.Cy 1 and Cy .sup.2 in one molecule may be the same or different from each other .sup.It is preferable that Cy 1 and Cy .sup.2 are the same from each other in terms of facilitating the acquisition and synthesis of raw materials, and .sup.it is preferable that Cy 1 and Cy .sup.2 are different in terms of easy liquefaction. The sulfur-containing aromatic heterocycle has at least a sulfur atom as a heteroatom constituting the aromatic heterocycle. In addition to the sulfur atom, the hetero atom may have an oxygen atom, a nitrogen atom, or an oxygen atom and a nitrogen atom. From the viewpoint of avoiding coloring and ensuring solubility, the number of heteroatoms constituting the sulfur-containing aromatic heterocycle is preferably 1 to 3, more preferably 1 to 2. Specific examples of the sulfur-containing aromatic heterocycle include an aromatic heterocycle containing one sulfur atom such as a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a thiopyran ring, a naphthophene ring, a dinaphthothiophene ring, and a dibenzothiopyran ring. Ring; Aromatic heterocycle containing two or more sulfur atoms such as thiantolen ring; thiazole ring, isothiazole ring, benzothiazole ring, naphthozazole ring, phenothiazine ring, thiazolomidazole ring, thiazolopyridine ring, thiazolopyridazine It contains two or more heteroatoms such as a ring, a thiazolopyrimidine ring, a dioxazolopyrazine ring, a thiazolopyrazine ring, a thiazolooxazole ring, a dibenzobenzothiophene ring, a thienooxazole ring, a thienothiazol ring, and a thiazolothiazol ring. Aromatic heterocycles can be mentioned. The sulfur-containing aromatic heterocycle may be a monocyclic ring or a condensed ring. A fused ring is preferable in terms of increasing the refractive index. The number of rings constituting the fused ring is preferably 2 to 5, more preferably 2 to 4, and particularly preferably 2 to 3 in terms of facilitating the acquisition of raw materials and synthesis. In particular, a benzothiazole ring, a dibenzothiophene ring, and a benzothiophene ring are preferable in terms of high refractive index and low colorability. Cy .sup.1, Cy .sup.2 and bonded to that linking group (-S-) .sup.may be attached to any position on the ring structure of the Cy 1, Cy .sup.2. Cy .sup.1 and Cy .sup.2 may have a substituent. As the substituent, for example, an alkyl group, an alkoxy group, an alkoxyalkyl group, an alkoxycarbonyl group, an alkoxyalkoxy group, and an alkanoyloxy group are preferable from the viewpoint of easily improving the solubility. Aryl groups, alkylthio groups, alkylthioalkyl groups, aryloxy groups, arylalkoxyl groups, and halogen atoms are preferable from the viewpoint of easily increasing the refractive index. Unsubstitution is preferred for achieving economical synthesis [0017-0022]
Claims 1-5 and 10-15 are rejected under 35 U.S.C. 102(a)(1) as being fully anticipated by Kolb et al. 20060147702.
Kolb et al. 20060147702 exemplifies compounds (fig 4)
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These monomers were used in compositions including a photoinitiator of examples 19 and 20 (table 2, [0073]). These high refractive index acrylates are bounded by
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where R1 is H, methyl, , m,n,p,q are 1-6 and Ar is any aromatic group [0014].
The composition including the identified monomer with a photoinitiator is inherently able to record a hologram. The cured polymer film is considered an optical element and is inherently able to be written upon using a two photo or other laser marking process to act as a memory device..
Claims 1-3 are rejected under 35 U.S.C. 102(a)(1) as being fully anticipated by Moon et al. KR 101907410.
Moon et al. KR 101907410 exemplifies
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Example 3 (table 2, page 25) combines monomer M66, hexanediol diacrylate (B1) polymer P-1, 2- (o-benzoyloxime) -1- [4- (phenylthio) phenyl] -1,2-octanedione (photoinitiator) in Propylene glycol methyl ether acetate (PGMEA). This was spin coated onto a substrate, dried, exposed using UV [0202-0210]. These monomers are bounded by formula B.
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Ra is hydrogen, deuterium, a substituted or unsubstituted C .sub.1 -C .sub.5 alkyl group, Wherein R1 to R4 are the same or different, independently represent hydrogen, deuterium, substituted or unsubstituted C .sub.1 -C .sub.30 an alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted C .sub.6 -C .sub.50 ring, each ring of C .sub.3 -C .sub.30 cycloalkyl groups, substituted or unsubstituted C .sub.1 -C .sub.30 alkoxy groups, substituted or unsubstituted C .sub.6 -C .sub.30 aryloxy groups, substituted or unsubstituted C .sub.1 -C .sub.30 alkyl A silyl group, a substituted or unsubstituted C .sub.6 -C .sub.30 arylsilyl group, a cyano group, a nitro group, and a halogen group, Y 2 to Y 4 are each the same or different and independently selected from a single bond, CH .sub.2 and O, The connecting group L1 to L4 are the same or different and, independently of each other a single bond, an alkyl ether of a substituted or unsubstituted C .sub.1 -C .sub.30 alkylene group, a substituted or unsubstituted C .sub.1 -C .sub.20 group, each substituted or unsubstituted hwandoen a C .sub.7 -C .sub.20 alkyl aryl group, a substituted or unsubstituted C .sub.7 -C .sub.20 aryl alkyl group, a substituted or unsubstituted cycloalkylene group, substituted or unsubstituted C .sub.3 -C .sub.60 unsubstituted C .sub.6 - and any one selected from an arylene group of C .sub.60, m is an integer of 1 to 3, and when m is 2 or more, the oxygen atom in each parenthesis, the moiety including L 1 and L 3 are the same or different from each other, Said substituents A2 to A4 are the same or different and, independently from each other hydrogen, deuterium, an alkyl group a substituted or unsubstituted C .sub.1 -C .sub.30, a substituted or unsubstituted C .sub.6 -C .sub.30 aryl group, or a substituted or unsubstituted, or an arylalkyl group of C .sub.7 -C .sub.30 [0017-0018,0029-0036]. The aryl group which is a substituent used in the compound of the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen elimination and includes a single or fused ring system containing 5 to 7 atoms, preferably 5 or 6 atoms, When a substituent is present in the aryl group, the adjacent substituent may be fused with each other to form a ring.
Specific examples of the aryl group include a phenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, o-terphenyl group, m- terphenyl group, p- terphenyl group, naphthyl group, anthryl group, An aromatic group such as a pyridyl group, an indenyl group, a fluorenyl group, a tetrahydronaphthyl group, a perylenyle, a crycenyl, a naphthacenyl, a fluoranthene and the like, and at least one hydrogen atom of the aryl group may be substituted with a deuterium atom, atom, a hydroxy group, a nitro group, a cyano group, a silyl group, an amino group (-NH2, -NH (R), -N (R ') (R''),R' and R "are independently from each other C .sub.1 -C .sub.10 an alkyl group, in which case the "alkyl group" hereinafter), an amidino group, a hydrazine group, a hydrazone jongi, a carboxyl group, a sulfonic acid group, phosphoric acid group, an alkyl group, a halogenated alkyl group of C .sub.1 -C .sub.24 in C .sub.1 -C .sub.24, C of .sub.2 -C .sub.24 alkenyl group, a C .sub.2 -C .sub.24 alkynyl group of, C .sub.1 -C .sub.24 heterocyclic group, C .sub.6 -C .sub.24 aryl group, C .sub.7 -C .sub.24 arylalkyl group, C .sub.2 -C .sub.24 of the A heteroaryl group or a C .sub.2 -C .sub.24 heteroarylalkyl group. The heteroaryl group which is a substituent used in the compound of the present invention is a C .sub.2 -C 8 alkyl group having 1, 2 or 3 hetero atoms selected from N, O, P, Si, S, Ge, Se and Te, Refers to a .sub.24 ring aromatic system, which rings can be fused to form a ring. And at least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as the aryl group [0067-0068].
Claims 1-5 and 10-15 are rejected under 35 U.S.C. 102(a)(1) as being fully anticipated by Gorou et al. JP 2016085447.
Gorou et al. JP 2016085447 (machine translation attached) exemplifies compound (22) [0169]
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These were synthesized in example Next, 17.6 parts by weight of the rod-shaped liquid crystal compound (21) and 2 parts by weight of the compound (22) having two or more kinds of mesogenic groups are mixed to obtain a first mixture (polymerizable liquid crystal composition). (A)) was obtained. Next, the polymerizable dichroic dye obtained in Synthesis Example 1 was added at a ratio of 1.0 part by weight with respect to 100 parts by weight of the total amount of the first mixture, and a polymerization initiator (BASF Corporation) was further added. Product name “Irgacure 651”, solid at room temperature (25 ° C.), 1.0 part by weight with respect to 100 parts by weight of the total amount of the polymerizable liquid crystal compound (A) and the polymerizable dichroic dye. Thus, a second mixture (solid) in which the polymerizable liquid crystal composition (A), the polymerizable dichroic dye, and the polymerization initiator were mixed was obtained. Next, the second mixture is dissolved in methyl ethyl ketone (solvent), and the insoluble matter is filtered through a polytetrafluoroethylene filter having a pore size of 0.45 μm. The polymerizable liquid crystal composition (A), polymerizable A mixed solution (third mixture) containing a dichroic dye, a polymerization initiator and a solvent was obtained. In producing the third mixture, the content of the solvent in the third mixture is 80% by weight, and the polymerizable liquid crystal composition (A), the polymerizable dichroic dye, and the polymerization start. The solvent was used so that the total amount with the agent was 20% by weight.
<Production of liquid crystal film>
The alignment substrate was prepared as follows. A 38 μm-thick polyethylene naphthalate film (manufactured by Teijin Limited) was cut into a 15 cm square, and a 5 wt% solution of alkyl-modified polyvinyl alcohol (PVA: Kuraray Co., Ltd., MP-203) (the solvent was water and isopropyl). (A mixed solvent of alcohol in a weight ratio of 1: 1) was applied by spin coating, dried on a hot plate at 50 ° C. for 30 minutes, and then heated in an oven at 120 ° C. for 10 minutes. Subsequently, it was rubbed with a rayon rubbing cloth. The film thickness of the obtained PVA layer was 1.2 μm. The peripheral speed ratio during rubbing (moving speed of rubbing cloth / moving speed of substrate film) was 4. The alignment substrate thus obtained is spin-coated with a mixed solution (third mixture) containing the liquid crystalline composition obtained as described above, a polymerizable dichroic dye, a polymerization initiator and a solvent. Was applied (coated) to form a coating film, and a laminate of the coating film and the alignment substrate was obtained. Next, the laminate of the coating film and the alignment substrate was left to stand for 2 minutes under the conditions of pressure: 1013 hPa and temperature: room temperature (25 ° C.), thereby removing the solvent from the coating film by drying. In addition, the solvent was removed from the entire surface of the coating film after 2 minutes had passed since the coating on the alignment substrate was completed. Next, using a high-pressure mercury lamp with an illuminance of 15 mW / cm .sup.2 , the integrated irradiation amount is set to 200 mJ / cm .sup.2 with respect to the coating film after removing the solvent by drying, and ultraviolet light (however, 365 nm). The liquid crystal compound is polymerized (cured) to fix the alignment state, and the liquid crystal film in which the alignment state is fixed is laminated on the alignment substrate. (Laminated body of liquid crystal film and alignment substrate) was obtained. Since the polyethylene naphthalate film used as the substrate has a large birefringence and is not preferable as an optical film, the optically anisotropic layer on the obtained alignment substrate is subjected to triacetylcellulose (TAC) via an ultraviolet curable adhesive. ) Transferred to film. That is, on the cured liquid crystal film layer on the polyethylene naphthalate film, an adhesive is applied to a thickness of 5 μm, laminated with a TAC film, and irradiated with ultraviolet rays from the TAC film side to cure the adhesive. After that, the alignment substrate was peeled off. When the obtained optical film (liquid crystal film / adhesive layer / TAC film) was observed under a polarizing microscope, it was found that there was no disclination and uniform orientation of the monodomain. Further, the extraordinary ray refractive index ne and ordinary ray refractive index no of the liquid crystal film layer of the obtained optical film were measured by spectroscopic ellipsometry. The wavelength dispersion characteristic of the refractive index of the liquid crystal film layer is shown in FIG. In the measurement wavelength range of 540 to 610 nm, it was confirmed that the extraordinary ray refractive index increases as the measurement wavelength increases.
The wavelength dispersion characteristic of retardation (Δnd) in the in-plane direction of the laminate of the TAC film and the liquid crystal film and the TAC film alone was measured using a trade name “Axoscan” manufactured by Axometrix, and the liquid crystal film layer was subtracted from both. The wavelength dispersion characteristics of birefringence were measured. FIG. 15 summarizes the birefringence wavelength dispersion characteristics of the liquid crystal film layer, and Table 1 summarizes the optical characteristics results. Δn .Math. d at 550 nm is 138 nm, Δn .Math. d (500) / Δn .Math. d (550) = 0.942, and Δn .Math. d (580) / Δn .Math. d (550) = 1.062. It was. In addition, Δn .Math. d (450) / Δn .Math. d (550) = 0.857, Δn .Math. d (650) / Δn .Math. d (550) = 1.113. In particular, it was confirmed that dispersion characteristics closer to ideal than Comparative Example 1 were exhibited on the longer wavelength side than the measurement wavelength of 550 nm.
Moreover, when the laminated body of a TAC film and a liquid crystal film was bonded to a glass with a thickness of 1.1 mm using an acrylic adhesive, and the dichroic ratio before and after a 120-hour heat test at a temperature of 85 ° C. was compared, The dichroic ratio was 4.8 before the test and 3.8 after the test, and the dichroic ratio maintenance rate was 80%, which was good dichroic ratio retention [0169-0180]
Claims 1-5 and 10-15 are rejected under 35 U.S.C. 103 as being unpatentable over Shibata et al. JP 2021024842.
Shibata et al. JP 2021024842 does not exemplify a photopolymerizable composition using a monomer bounded by the claims or a cured polymer.
It would have been obvious to one skilled in the art to modify example 5 by replacing at least a portion of monomer 1A-1 with one of monomers 1A-2, 1A-3, 1A-11 or 1A-12 and exposing it to form a cured film with a reasonable expectation of forming a useful photopolymerizable composition and cured polymer film.
The resulting compositions including the identified monomers with a photoinitiator is inherently able to record a hologram. The resulting cured polymer film is considered an optical element and is inherently able to be written upon using a two photo or other laser marking process to act as a memory device.
Claims 1-3,5,6 and 10-15 are rejected under 35 U.S.C. 103 as being unpatentable over Moon et al. KR 101907410.
Moon et al. KR 101907410 (machine translation attached) does not exemplify a photopolymerizable composition using a monomer bounded by the claims or a cured polymer.
With respect to claims 1-3 and 10-15, it would have been obvious to modify example 3 of Moon et al. KR 101907410 by replacing at least a portion of monomer M66 with one of monomers M72 or M73 and exposing it to form a cured film with a reasonable expectation of forming a useful photopolymerizable composition and cured polymer film.
Alternatively with respect to claims 1-3,5 and 10-15, it would have been obvious to modify example 3 of Moon et al. KR 101907410 by replacing at least a portion of monomer M66 with another monomers bounded by formula B where L1 to L4 are CH2, Y1 and Y2 are a single bond, Y3 is oxygen and A2,A3 or A4 are a C6-30 aryl such as phenyl, napthyle, biphenyl as taught at [0017-0018,0029-0036,0067-0068] and exposing it to form a cured film with a reasonable expectation of forming a useful photopolymerizable composition and cured polymer film.
Alternatively with respect to claims 1-3,6 and 10-15, it would have been obvious to modify example 3 of Moon et al. KR 101907410 by replacing at least a portion of monomer M66 with another monomers bounded by formula B where L1 to L4 are CH2, Y1 and Y2 are a single bond, Y3 is oxygen and A2,A3 or A4 are a heteroaryl group as taught at [0017-0018,0029-0036,0067-0068] and exposing it to form a cured film with a reasonable expectation of forming a useful photopolymerizable composition and cured polymer film.
The resulting compositions including the identified monomers with a photoinitiator is inherently able to record a hologram. The resulting cured polymer film is considered an optical element and is inherently able to be written upon using a two photo or other laser marking process to act as a memory device..
Claims 1-6 and 10-16 are rejected under 35 U.S.C. 103 as being unpatentable over Hioki et al. JP 2017014213, in view of Chisholm et al. 20050049376 and Okutsu et al. JP 2010215693
Hioki et al. JP 2017014213 exemplifies compounds
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which are bounded by formula
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Wherein, R .sup.1 represents a hydrogen atom or a methyl group, R .sup.2 represents an aromatic ring which may have a substituent, and X .sup.1 and X .sup.2 are each independently oxygen, sulfur, or substituted. Represents a nitrogen atom which may have a group, A .sup.1 and A .sup.2 each independently represent a divalent group, and m and n each independently represent an integer of 0 or 1. R .sup.2 in may have a condensed ring as also aromatic ring having a substituent R .sup.2, large aromatic hydrocarbon ring, aromatic heterocyclic ring, the aralkyl group Can be separated. Aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, tetracene, pyrene, benzpyrene, chrysene, biphenylene, triphenylene, acenaphthene, fluoranthene, fluorene, etc. The group of is mentioned. As aromatic heterocycles, furan ring, benzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, naphthothiophene ring, dinaphthothiophene ring, pyrrole ring, indole ring, carbazole ring, pyridine ring, quinoline ring , Aromatic heterocycles containing one heteroatom such as isoquinoline ring; heteroatoms such as imidazole ring, triazole ring, tetrazole ring, oxazole ring, thiazole ring, pyridazine ring, pyrimidine ring, pyrazine ring, triazine ring, thiadiazole ring Aromatic heterocycles containing two or more of: benzoxazole ring, thienoxazole ring, thiazolooxazole ring, oxazolooxazole ring, oxazoloimidazole ring, oxazolopyridine ring, oxazolopyridazine ring, oxazolopyrimidine ring, ox Zolopyrazine ring, naphthoxazole ring, quinolinoxazole ring, dioxazolopyrazine ring, phenoxazine ring, benzothiazole ring, furothiazole ring, thienothiazole ring, thiazolothiazole ring, thiazoloimidazole ring, thienothiadiazole ring, thiazolo Aromatic heterocycles containing two or more heteroatoms such as thiadiazole, thiazolopyridine, thiazolopyridazine, thiazolopyrimidine, thiazolopyrazine, naphthothiazole, quinolinothiazole, and phenothiazine And a ring in which two or three rings are fused. These ring structures may be connected to a sulfur atom at an arbitrary position, and may have an arbitrary substituent. Examples of the aralkyl group include a benzyl group, a 2-phenylethyl group, a naphthylmethyl group, a furylmethyl group, a thienylmethyl group, a benzothienylmethyl group, and the like, and may have an arbitrary substituent. Among these aromatic rings that may have a substituent, an aromatic hydrocarbon ring is preferable, and a naphthalene ring, anthracene ring, and fluorene ring are more preferable from the viewpoint of achieving both a low water absorption and a high refractive index [0014-0017].
(Example 5)
Using the above-mentioned compound M-1, a hologram recording medium was produced by the following procedure.
<Preparation of photoreactive composition for hologram recording medium>
Compound M-1 (polymerizable monomer) and diphenyl (2,4,6-trimethylbenzoyl) phosphine oxide (photopolymerization initiator) were dissolved in hexamethylene diisocyanate (isocyanate) to obtain liquid A.
Next, an octylic acid solution of tris (2-ethylhexanoate) bismuth (urethane polymerization catalyst) was dissolved in polyoxypropylene glycol (polyol) having a molecular weight of about 1000 to prepare a B solution.
Each of liquid A and liquid B was degassed under reduced pressure at 45 ° C. for 2 hours, and then liquid A and liquid B were stirred and mixed, and further degassed under reduced pressure for several minutes.
<Production of hologram recording medium>
Subsequently, a spacer sheet having a thickness of 1.5 mm and a width of 10 mm is placed on the ends of two opposite sides of 75 mm of a rectangular slide glass of 25 mm × 75 mm, and the above mixed liquid is vacuum degassed between the spacer sheets on the slide glass. Then, another glass slide was placed thereon, the periphery was fixed with a clip and heated at 80 ° C. for 24 hours to produce a hologram recording medium. In this hologram recording medium, a recording layer having a thickness of 1.5 mm is formed between slide glasses as a support. In addition, a plurality of the above-mentioned hologram recording media were produced for evaluation of recording performance described later.
(Comparative Example 2)
As compound M-5, 1,4-bis (2-naphthylthio) -2-butyl acrylate was synthesized according to the following procedure.
To a mixture containing 2.69 g of potassium t-butoxide stirred in 40 ml of acetone at room temperature, 3.21 g of 2-naphthalenethiol was added. The red colored solid dissolved and the mixture was stirred for an additional 15 minutes. 2.54 g of 1,4-dibromo-2-butanol was added over 15 minutes and a precipitate formed. After 1 hour, it was confirmed that 2-naphthalenethiol completely disappeared by thin layer chromatography (using 40% dichloromethane / hexane as a developing solvent). The mixture was filtered and washed with 20 ml of acetone and the filtrate was concentrated on a rotary evaporator. The resulting brown solid was crystallized from cyclohexane to yield the intermediate butanol compound as a yellow powdery solid (3.0 g, 76% yield). Recrystallization with isopropyl alcohol produced a pure intermediate butanol compound that could be obtained. To a solution of 1.96 g of intermediate butanol compound and 0.51 g of triethylamine, which was stirred at 0 ° C. in 40 ml of dichloromethane, 0.46 g of acryloyl chloride was added and stirred for 1 hour. It is washed with 10 ml of 5% aqueous sodium bicarbonate solution and 10 ml of deionized water, dried over anhydrous sodium sulfate, the solvent is removed on a rotary evaporator and 2.10 g of compound M-5 as a yellow viscous oil. (94% yield) was obtained.
Compound M-5 is a compound having a high refractive index contrast and useful as a polymerizable monomer for a hologram recording medium in Japanese Patent Application Publication No. 2005-527867 and International Publication No. 2003/102693 pamphlet.
In Example 5, M-5 was used in place of Compound M-1 as the polymerizable monomer, and B
A holographic recording medium of Comparative Example 2 was prepared in the same manner except that dibutyltin dilaurate (urethane polymerization catalyst) was dissolved in polyoxypropylene glycol (polyol) having a molecular weight of about 1000 as the liquid. Table 1 shows the content of each material in the photoreactive compositions used in Example 5 and Comparative Example 2.
<Hologram recording and evaluation method>
Using the hologram recording media of Example 5 and Comparative Example 2 described above, the hologram recording performance was evaluated by the procedure described below.
The incident angle to the hologram recording medium was 61 multiple recordings at the same location from -30 ° to 30 ° every other 1 °, and the sum of the square roots of diffraction efficiency at that time was M / # (M number). Hereinafter, the measurement method will be described in detail with reference to FIG.
(Measurement of M / #)
FIG. 1 is a configuration diagram showing an outline of an apparatus used for hologram recording.
In FIG. 1, S indicates a hologram recording medium, M1 and M2 both indicate mirrors, PBS indicates a polarization beam splitter, and L1 indicates a semiconductor laser light source for recording light that emits light having a wavelength of 405 nm (a single mode manufactured by TOPPICA Photonics). Laser), PD1
And PD2 indicate a photodetector (S2281 manufactured by Hamamatsu Photonics). Reference numeral 1 denotes a post-exposure LED unit.
The light having a wavelength of 405 nm generated from L1 was divided by PBS, and crossed on the recording surface so that the angle formed by the two beams was 37.3 °. At this time, the bisector of the angle formed by the two beams is perpendicular to the recording surface, and the vibration planes of the electric field vectors of the two beams obtained by the division are two intersecting lines. Irradiation was performed so as to be perpendicular to the plane including the beam.
The above case was set to 0 °, and the angle of moving the hologram recording medium with respect to the optical axis was changed from -30 ° to 30 ° in increments of 1 degree, and 61-multiplex recording was performed.
After 61 multiple recording, the LED unit 1 (wavelength 405 nm) was turned on for a certain period of time to perform post-exposure, and the polymerizable monomer remaining without being polymerized was completely polymerized.
Subsequently, only the light (wavelength 405 nm) from the mirror M1 in FIG. 1 is irradiated as the reference light, the reproduction light is detected by PD1 and PD2, and a photo sensor amplifier (C9329 manufactured by Hamamatsu Photonics, not shown) is used. The diffraction efficiency from an angle of −30 ° to 30 ° was measured. The sum of the square roots of the obtained diffraction efficiencies over the entire multiple recording area was defined as M / #.
Using a plurality of hologram recording media prepared for each example and comparative example, the evaluation was performed a plurality of times by changing the increase and decrease of the irradiation energy at the initial stage of recording and the increase and decrease of the total irradiation energy. The irradiation energy was changed in the range of 10 to 3000 mJ / cm .sup.2 by changing the irradiation time with the power density of L1 being 15 mW / cm .sup.2 . Specifically, several percent for each recording While maintaining the above diffraction efficiency, a condition for allowing the contained monomer to polymerize almost completely by 61 multiplex recording (M / # almost reaches equilibrium by 61 multiplex recording) was sought, and the maximum value was obtained as M / #. I was able to. The maximum value obtained was defined as M / # of the medium.
<Evaluation results of M / #>
M / # of the hologram recording medium of Example 5 was 18.4, and M / # of the hologram recording medium of Comparative Example 2 was 11.6. It was found that a hologram recording medium having good recording characteristics can be obtained by using the polymerizable monomer having a high refractive index of the present invention [0204-0218)
Chisholm et al. 20050049376 teaches exemplifies monomers.
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These are bounded by formula (I)
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wherein Z is an ethylenically unsaturated group; X is O, S, or NH; L.sup.1 and L.sup.2 are each independently C.sub.1-C.sub.3 alkylene, --(C.sub.1-C.sub.3 alkylene)-S--(C.sub.1-C.sub.3 alkylene)-, or --(C.sub.1-C.sub.3 alkylene)-O--(C.sub.1-C.sub.3 alkylene)-; R is hydrogen or C.sub.1-C.sub.6 alkyl; R.sup.1 and R.sup.2 are each independently aryl, including phenyl or naphthyl, aryl(C.sub.1-C.sub.6 alkylene)-, heteroaryl, or heteroaryl(C.sub.1-C.sub.6 alkylene)-, each of which group is substituted with 0 to 5 substituents independently chosen from halogen, C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy, (C.sub.1-C.sub.4alkyl)S--, C.sub.1-C.sub.4haloalkyl, and C.sub.1-C.sub.4haloalkoxy; and Y.sup.1 and Y.sup.2 are each independently O, S, NH or N, with the proviso that when Y.sup.1 and Y.sup.2 are both S, i) X is S, ii) at least one of R.sup.1 and R.sup.2 is heteroaryl or heteroaryl(C.sub.1-C.sub.6 alkylene) substituted as previously described, or iii) one or both of L.sup.1 and L.sup.2 are--(C.sub.1-C.sub.3 alkylene)-S--(C.sub.1-C.sub.3 alkylene)-, or --(C.sub.1-C.sub.3 alkylene)-O--(C.sub.1-C.sub.3 alkylene)-; and with the proviso that when Y.sup.1 or Y.sup.2 is N, then each corresponding combination R.sup.1--Y.sup.1 or R.sup.1--Y.sup.2 is independently an N-containing heteroaryl excluding carbazole [0016-0017].
Okutsu et al. JP 2010215693 (machine translation attached) teaches monomers bounded by
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In general formula (1), R .sup.1 and R .sup.2 each represent the same or different heteroaryl group. Specific examples of heteroaryl groups that R .sup.1 and R .sup.2 can take include groups having a benzothiazole skeleton, a benzoxazole skeleton, a furan skeleton, a pyrroline skeleton, a thiazoline skeleton, an oxazoline skeleton, an indoline skeleton, a thiobenzene skeleton, and a pyridine skeleton. Among them, a group having a benzothiazole skeleton or a benzoxazole skeleton is preferable, and a group having a benzothiazole skeleton is more preferable. The bond toward the phenylene group to which R .sup.1 and R .sup.2 are bonded preferably extends from the heterocycle constituting the heteroaryl group, and more preferably extends from the carbon atom constituting the heterocycle. R .sup.1 and R .sup.2 are preferably groups having the same skeleton, and R .sup.1 and R .sup.2 are more preferably the same. In general formula (1), R .sup.3 represents a hydrogen atom, an alkyl group or an aryl group. Number of carbon atoms of the alkyl group R .sup.3 can be taken preferably 1-4, more preferably 1-2, 1 is more preferred. Examples of the alkyl group include a methyl group and an ethyl group. The alkyl group may be substituted, but is preferably unsubstituted. R .sup.3 is the number of carbon atoms of the aryl group can take is preferably 6-10, more preferably 6-7, 6 is more preferable. A phenyl group can be mentioned as an aryl group. The aryl group may be substituted, but is preferably unsubstituted. R .sup.3 is particularly preferably a hydrogen atom or a methyl group. In general formula (1), R .sup.4 and R .sup.5 each represent the same or different divalent linking group or single bond. Examples of the divalent linking group that R .sup.4 and R .sup.5 can take include an alkylene group, an arylene group, —O—, —S—, —CO—, —NH—, and a linking group obtained by combining these. R .sup.4, carbon atoms in the alkylene group R .sup.5 can take preferably 1 to 5, more preferably 1 to 3, 1 is more preferred. Specific examples include a methylene group, an ethylene group, and a propylene group. R .sup.4, carbon atoms of the arylene group R .sup.5 can be taken is preferably 6-10, more preferably 6-7, 6 is more preferable. Specific examples include 1,4-phenylene group, 1,3-phenylene group, 1,2-phenylene group, 1,5-naphthylene group, 1,8-naphthylene group, 2,6-naphthylene group, 2,7- A naphthylene group can be mentioned. The alkylene group and the arylene group may each be substituted, and the description of the substituent of the heteroaryl group can be referred to for examples and preferred ranges of the substituent. The divalent linking group that R .sup.4 and R .sup.5 can be preferably an alkylene group having 1 to 6 carbon atoms, an arylene group having 6 to 10 carbon atoms, —O—, or a linking group obtained by combining these, It is more preferably an alkylene group having 1 to 4 carbon atoms, an arylene group having 6 carbon atoms, -O-, or a linking group in combination of these, an alkylene group having 1 to 2 carbon atoms, an arylene group having 6 carbon atoms,- O- or a linking group combining these is more preferable, a methylene group, an ethylene group or a phenylene group is still more preferable, and a methylene group is most preferable. In the general formula (1), X .sup.1 , X .sup.2 and X .sup.3 each independently represent an oxygen atom, a sulfur atom or N—R .sup.6 . R .sup.6 represents a hydrogen atom or an alkyl group. Number of carbon atoms of the alkyl group R .sup.6 can take preferably 1-4, more preferably 1-2, 1 is more preferred. Examples of the alkyl group include a methyl group and an ethyl group. The alkyl group may be substituted, but is preferably unsubstituted. R .sup.6 is preferably a hydrogen atom, a methyl group or an ethyl group, more preferably a hydrogen atom or a methyl group, and even more preferably a hydrogen atom. X .sup.1 , X .sup.2 , and X .sup.3 are each independently preferably an oxygen atom or a sulfur atom, and more preferably an oxygen atom. X .sup.1 and X .sup.2 are preferably the same, and X .sup.1 , X .sup.2 and X .sup.3 are more preferably all the same [0012-0022].
Hioki et al. JP 2017014213 does not exemplify compounds bounded by formula (I) where the (X2-A2)n-S-R2 are different moieties.
With respect to claims 1-5, it would have been have been obvious to one skilled in the art to modify any of the compounds
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by replacing only one of the sulfur linkages with an oxygen or NH or NR based upon the equivalence of O, S, NH or NR at [0016-0017 of Chisholm et al. 20050049376 and [0012-0022] of Okutsu et al. JP 2010215693 with a reasonable expectation of forming a useful monomer, noting the monomer
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disclosed in Chisholm et al. 20050049376.
With respect to claims 1-5 and 10-16, it would have been have been obvious to one skilled in the art to modify any of the compounds
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by replacing only one of the sulfur linkages with an oxygen or NH or NR based upon the equivalence of O, S, NH or NR at [0016-0017 of Chisholm et al. 20050049376 and [0012-0022] of Okutsu et al. JP 2010215693 with a reasonable expectation of forming a useful monomer, noting the monomer
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disclosed in Chisholm et al. 20050049376 and to use the resulting monomer in a holographic recording composition and processes disclosed in Hioki et al. JP 2017014213with a reasonable expectation of forming a useful photopolymer and hologram.
Claims 1-6 and 10-17 are rejected under 35 U.S.C. 103 as being unpatentable over Shimizu et al. JP 2019215538, in view of Chisholm et al. 20050049376 and Okutsu et al. JP 2010215693
Shimizu et al. JP 2019215538 (machine translation attached) exemplifies monomers
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These are embraced by the formula (1) at [0070],
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Where Q is a thiophene-containing sulfide group which may have a substituent. G is an acryloyl or methacryloyl group. L is a group of Q and G which may have a substituent. It is an r + s-valent linking group or a direct bond to be connected. R represents an integer of 1 to 5. s represents an integer of 1 to 5.)[0070-0071]. Liquid A was prepared by dissolving 0.325 g of polymerizable monomer BDTPA and 0.0198 g of photopolymerization initiator HLI02 in 4.14 g of duranate (TM) TSS-100.
Separately, 3.06 g of SH6 and 1.65 g of Praxel PCL-305 (polycaprolactone triol (molecular weight: 550)) were mixed (SH6: Praxel PCL-305 = 65: 35 (weight ratio)), and tris (2-ethyl Octanoic acid solution of (hexanoate) bismuth: 0.0013 g was dissolved to obtain solution B.
Liquid A and Liquid B were each degassed under reduced pressure at 45 ° C. for 2 hours, and then liquid A, liquid B and TEMPOL masterbatch were stirred and mixed, and further degassed in vacuo for several minutes
Subsequently, the above-mentioned mixed solution, which has been vacuum degassed, is poured onto a slide glass on which two 0.5 mm-thick spacer sheets are placed opposite to each other, and the slide glass is placed thereon, and the periphery is fixed with clips. And it heated at 80 degrees C for 24 hours, and produced the sample for a composition for hologram recording media evaluation. In this evaluation sample, a recording layer having a thickness of 0.5 mm is formed between slide glasses as a cover.
In the composition for a hologram recording medium, (PG + TMG) / ((a-1) + (b-1)) was 23.9% by weight, and (CL) / ((a-1) + (b-1)). Is 32.3% by weight, the content of the polymerizable monomer of the component (c-1) is 3% by weight, and the photopolymerization initiator of the component (d-1) is added to the polymerizable monomer of the component (c-1). 6.1% by weight, the molar ratio of TEMPOL of the component (e-1) to the photopolymerization initiator of the component (d-1) was 0.72, and the component based on the isocyanate group of the component (a-1) The hydroxyl group ratio (OH / NCO) of (b-1) was 1.0 [0267-0271].
<AR glass light guide plate application>
A volume hologram is recorded on the hologram recording medium of the present invention in the same manner as in the above-described large-capacity memory application [0242]
Shimizu et al. JP 2019215538 does not exemplify where r is 3 and one Q is different form the others
With respect to claims 1-5, it would have been obvious to one skilled in the art to modify
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by replacing only one of the sulfur linkages with an oxygen or NH or NR based upon the equivalence of O, S, NH or NR at [0016-0017 of Chisholm et al. 20050049376 and [0012-0022] of Okutsu et al. JP 2010215693 with a reasonable expectation of forming a useful monomer, noting the monomer
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disclosed in Chisholm et al. 20050049376.
Alternatively with respect to claims 1-5, it would have been obvious to one skilled in the art to modify
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by replacing one of the dibenzothiophene moieties with a benzothiophene moiety
based upon the disclosure of the monomer
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in Chisholm et al. 20050049376 and the different R1 and R2 groups on the phenyl ring in formula (I) of Okutsu et al. JP 2010215693 with a reasonable expectation of forming a useful monomer.
Alternatively with respect to claims 1-6, it would have been obvious to one skilled in the art to modify
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by replacing one of the dibenzothiophene moieties with a nitrogen containing heterocyclic moiety disclosed by Okutsu et al. JP 2010215693
based upon the disclosure of the monomer
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in Chisholm et al. 20050049376 and the equivalence of these R groups on the phenyl ring in formula (I) of Okutsu et al. JP 2010215693 with a reasonable expectation of forming a useful monomer.
With respect to claims 1-5 and 10-17, it would have been obvious to one skilled in the art to modify
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by replacing only one of the sulfur linkages with an oxygen or NH or NR based upon the equivalence of O, S, NH or NR at [0016-0017 of Chisholm et al. 20050049376 and [0012-0022] of Okutsu et al. JP 2010215693 with a reasonable expectation of forming a useful monomer, noting the monomer
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disclosed in Chisholm et al. 20050049376 and to use the resulting monomer in a holographic recording composition and holographic recording processes disclosed in Shimizu et al. JP 2019215538 with a reasonable expectation of forming a useful photopolymer and AR hologram.
With respect to claims 1-5 and 10-17, it would have been obvious to one skilled in the art to modify
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by replacing one of the dibenzothiophene moieties with a benzothiophene moiety
based upon the disclosure of the monomer
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in Chisholm et al. 20050049376 and the different R1 and R2 groups on the phenyl ring in formula (I) of Okutsu et al. JP 2010215693 and to use the resulting monomer in a holographic recording composition and holographic recording processes disclosed in Shimizu et al. JP 2019215538 with a reasonable expectation of forming a useful photopolymer and AR hologram.
Alternatively with respect to claims 1-6 and 10-17, it would have been obvious to one skilled in the art to modify
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by replacing one of the dibenzothiophene moieties with a nitrogen containing heterocyclic moiety disclosed by Okutsu et al. JP 2010215693
based upon the disclosure of the monomer
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in Chisholm et al. 20050049376 and the equivalence of these R groups on the phenyl ring in formula (I) of Okutsu et al. JP 2010215693 and to use the resulting monomer in a holographic recording composition and holographic recording processes disclosed in Shimizu et al. JP 2019215538 with a reasonable expectation of forming a useful photopolymer and AR hologram.
Claims 1-6 and 10-16 are rejected under 35 U.S.C. 103 as being unpatentable Ishikawa et al. WO 2021100654, in view of Chisholm et al. 20050049376 and Okutsu et al. JP 2010215693
Ishikawa et al. WO 2021100654 (machine translation attached) exemplifies compounds including (pages 16-20)
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These are bounded by formula (I)
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In the formula, R .sup.1 represents a hydrogen atom or a methyl group. R .sup.2 represents an aromatic ring group which may have a substituent or an alkyl group substituted with an aromatic ring group which may have a substituent. X .sup.1 has a (thio) ester bond, a (thio) carbonate bond, a (thio) amide bond, a (thio) urethane bond, a (thio) urea bond, or a (thio) ether bond, or an oxygen, sulfur, or substituent. Represents a nitrogen atom that may have. X .sup.2 represents an oxygen, sulfur, or nitrogen atom that may have a substituent. A represents a divalent group which may have a substituent. L represents a (m + 1) valent linking group that may have a substituent. m represents an integer of 1 to 3. n represents 0 or 1. [0012-0013].
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(page 78),
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Compound M-1: 0.269 g as a polymerizable monomer, photopolymerization initiator HLI02: 0.0097 g, and radical scavenger TEMPOL: 3.33 mg are dissolved in Duranate® TSS-100: 2.53 g to A. It was made into a liquid. Separately, 1.73 g of Praxel PCL-205U and 0.74 g of Praxel PCL-305: 0.74 g were mixed (Plaxel PCL-205U: Praxel PCL-305 = 70: 30 (mass ratio)), and Tris (2-ethylhexanoate) was added. ) Bismuth octyl acid solution: 0.3 mg was dissolved to prepare solution B. Liquids A and B were degassed at 45 ° C. for 2 hours under reduced pressure, and then 2.39 g of solution A and 2.11 g of solution B were stirred and mixed, and degassed in vacuum for a few more minutes.Subsequently, the vacuum-degassed mixed solution is poured onto the slide glass on which a spacer sheet having a thickness of 0.5 mm is placed on the two opposite ends, the slide glass is placed over the slide glass, and the periphery is fixed with a clip. Then, it was heated at 80 ° C. for 24 hours to prepare a hologram recording medium 1 as an evaluation sample. In this evaluation sample, a recording layer having a thickness of 0.5 mm is formed between slide glasses as a cover. The hologram recording medium 1 is blended with a ratio of the number of isocyanate radicals in solution A to the number of isocyanate-reactive groups in solution B of 1.0, a polymerizable monomer of 58.3 μmol / g, and a photopolymerization initiator of 3. The amount was .63 μmol / g and the radical scavenger was 3.63 μmol / g. Using the hologram recording media 1 and 2 produced as the evaluation samples, the hologram recording and the hologram recording performance of the hologram recording medium were evaluated by the procedure described below. Hologram recording was performed using a semiconductor laser having a wavelength of 405 nm and an exposure power density of 7.5 mW / cm .sup.2 per beam using the exposure apparatus shown in FIG. The medium was rotated from -18 ° to 18 ° and angle multiple recording was performed at the same location. Diffraction efficiency at each multiplex recording was measured. Δn was calculated from the obtained diffraction efficiency, and the total sum of the entire multiple recordings was taken as totalΔn [0333-0351]. As described above, in the optical element application of the AR glass light guide plate, the higher the totalΔn, the brighter the projected image and the wider the viewing angle. For example, Δn = 1.7 times (0.0123 .fwdarw. 0.0213) corresponds to 2.1 times the diffraction efficiency, which means that the brightness of the projected image is improved 2.1 times. This means that for the same projected image brightness, the power consumption is increased by 0.5 times or the battery usage time is increased by 2.1 times. Further, in memory applications, the recording capacity can be improved by improving totalΔn [0408]
Ishikawa et al. WO 2021100654 does not exemplify compounds bounded by formula (I) where the (X2-A)n-S-R2 are different moieties.
With respect to claims 1-5, it would have been have been obvious to one skilled in the art to modify any of the compounds
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by replacing only one of the sulfur linkages with an oxygen or NH or NR based upon the equivalence of O, S, NH or NR at [0016-0017 of Chisholm et al. 20050049376 and [0012-0022] of Okutsu et al. JP 2010215693 with a reasonable expectation of forming a useful monomer, noting the monomer
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disclosed in Chisholm et al. 20050049376.
Altrernatively with respect to claims 1-5, it would have been have been obvious to one skilled in the art to modify any of the compounds
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by replacing only one of the moieties attached to the phenyl ring with a different moiety based upon the disclosure of the monomer
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in Chisholm et al. 20050049376 and the different R1 and R2 groups on the phenyl ring in formula (I) of Okutsu et al. JP 2010215693 with a reasonable expectation of forming a useful monomer.
With respect to claims 1-5 and 10-17, it would have been have been obvious to one skilled in the art to modify any of the compounds
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by replacing only one of the sulfur linkages with an oxygen or NH or NR based upon the equivalence of O, S, NH or NR at [0016-0017 of Chisholm et al. 20050049376 and [0012-0022] of Okutsu et al. JP 2010215693 with a reasonable expectation of forming a useful monomer, noting the monomer
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disclosed in Chisholm et al. 20050049376 and to use the resulting monomer in a holographic recording composition and holographic recording processes disclosed in Ishikawa et al. WO 2021100654 with a reasonable expectation of forming a useful photopolymer and hologram.
With respect to claims 1-5 and 10-17, it would have been have been obvious to one skilled in the art to modify any of the compounds
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by replacing only one of the moieties attached to the phenyl ring with a different moiety based upon the disclosure of the monomer
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in Chisholm et al. 20050049376 and the different R1 and R2 groups on the phenyl ring in formula (I) of Okutsu et al. JP 2010215693 and to use the resulting monomer in a holographic recording composition and holographic recording processes disclosed in Ishikawa et al. WO 2021100654 with a reasonable expectation of forming a useful photopolymer and AR hologram.
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Shimada 20050191581 exemplifies monomer
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(page 84)
This is bounded by formula (I) on page 4 [0046-0058].
Alim et al. WO 2019237117 teaches monomers useful in holograms bounded by
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Wanders et al. 20090054978 teaches monomers bounded by formula (I)
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R.sup.1 is H or CH.sub.3; R.sup.2 is a C.sub.1-C.sub.3 alkylene or -C.sub.1-C.sub.3 alkylene)-Y-(C.sub.1-C.sub.3 alkylene)-; Y is O or S; R.sup.3 is C.sub.6-C.sub.18 aryl or heteroaryl; R.sup.4 is H or linear or branched C.sub.1-C.sub.6 alkyl; m+n=3; n=0, 1 or 2; and m=1,2 or 3; is polymerized by employing an initiator that is activated by light having a wavelength of 390 nm or more [0020-0021]. he HRI monomer 1,3-bis(phenylthio)propan-2-yl methacrylate (M2) was formulated in the following composition under subdued light conditions to avoid premature decomposition of the photoinitiator: 92.85 EGDMA* 6.0 UV-blocker** 1.0 Irg 819*** 0.15 *Ethylene Glycol Di Methacrylate **A methacrylate modified benzotriazole based material from Sigma-Aldrich ***A phosphineoxide based photoinitiator from Ciba Specialty Chemicals. The photocurable HRI monomer containing composition as prepared previously was added to a polymeric castmould consisting of a lower and a upper half enclosing a space in the form of an IOL molding. The mound was irradiated with blue light under suitable conditions for the appropriate amount of time. After opening of the mound the IOL molding was removed and inspected for quality. It was found that the molding consisted of an optically transparent material with the desired properties for a suitable IOL material. The molding did not tear on folding, and returned to the original dimensions when the folding force was released. Folding marks were not visible after folding, while elongation was about 100%. [0056-0058].
Schlueter 20080266519 exemplifies (meth)acrylate compounds
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20250130507, 20250122329 are related but do not claim the same compounds.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Martin J Angebranndt whose telephone number is (571)272-1378. The examiner can normally be reached 7-3:30 pm EST.
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MARTIN J. ANGEBRANNDT
Primary Examiner
Art Unit 1737
/MARTIN J ANGEBRANNDT/Primary Examiner, Art Unit 1737 June 19, 2026
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