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. Rejections of the previous action not repeated blow are withdrawn based upon the arguments and amendments advanced by the applicant. Responses to the arguments of the applicant are presented after the first rejection they are directed to .
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 1,2,5-9,14,16,18-21 are rejected under 35 U.S.C. 103 as being unpatentable over Sasaki et al. JP 2008268520, in view of Kosaka 20030194487, Weiser et al. 20140295328 and Hamaide et al. JP 2014-044242.
Sasaki et al. JP 2008268520 (machine translation attached) in example 1 reacts 100 parts of modified glycerin propylene oxyto (G-400, manufactured by Asahi Denka G-400, molecular weight of about 400), 10 parts of trimethylolpropane monoallyl ether (TAE), hexamethylene diisocyanate (HDI) Asahi Kasei Duranate HDI) 58 parts, Dibutyltin dilaurate (DBTL, Asahi Denka) 0.06 part, 2,4-dibromophenyl acrylate (DBPA) 19 parts, Irgacure 784 (Irg784, manufactured by Ciba Specialty Chemicals) 2.8 parts and 0.9 part of diisopropylethylamine (DiPEA) were mixed well at 25 ° C. for 30 minutes to prepare a composition A for a uniform recording medium. Attach a tape made of polytetrafluoroethylene with a thickness of 500 μm as a spacer to the three ends of the glass substrate (50 × 50 × 0.5 mm), and then attach the glass substrate (50 × 50 × 0.5 mm). A sample cell was obtained. The composition prepared above was injected into the cell from one end of this sample cell, and heated at 80 ° C. for 2 hours to cure the matrix to produce a recording medium A1 (for transmission hologram measurement).In addition, the reflective recording medium A2 was prepared by using the same method as described above as a glass substrate (50 × 50 × 0.5 mm) with an aluminum vapor deposition layer (reflective layer). Data recording with a two-beam interference type transmission hologram As shown in FIG. 1, the sample is irradiated with a recording laser beam (information beam and reference beam) to record the hologram, while reading with a wavelength different from that of the recording laser beam. The intensity of the light diffracted from the recorded hologram was observed using a laser beam for use [0061-0065]. In the composition of the present invention, component 6 is preferably blended as necessary for the purpose of adjusting the degree of polymerization of the polymer matrix. Any component 6 can be used as long as the degree of polymerization of the produced polymer can be adjusted (chain transfer agent) . Specific examples of component 6 include tertiary amines, alkylthiols having about 1 to 20 carbon atoms, disubstituted allyls, tertiary butyl sulfides, disulfide compounds, cumyl dithiobenzoates, carbon tetrachloride and four odors. Alkyl halides such as carbon fluoride, triethylaluminum, metal ion-containing redox catalysts, AIBNs, azo compounds, N-arylmaleimides, cobalt complexes of hemapolyphyllin tetramethyl ether, addition represented by the following formula (1)
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In the formula (1), Y represents COOR .sub.1 and a cyano group, R .sub.1 represents an alkyl group having 1 to 6 carbon atoms, X represents a bromine atom, SR .sub.2 , SnR .sub.3 , SO .sub.2 Ar, and R .sub.2 represents an alkyl group having 1 to 6 carbon atoms, R .sub.3 represents an alkyl group having 1 to 6 carbon atoms, Ar represents an aryl group.
.sub.CH 2 = C (-Y) -CH 2 X (1),
In the formula (1), Y represents COOR .sub.1 and a cyano group, R .sub.1 represents an alkyl group having 1 to 6 carbon atoms, X represents a bromine atom, SR .sub.2 , SnR .sub.3 , SO .sub.2 Ar, and R .sub.2 represents an alkyl group having 1 to 6 carbon atoms, R .sub.3 represents an alkyl group having 1 to 6 carbon atoms, Ar represents an aryl group . Examples include cleavage type chain transfer agents, quinones, nitro / nitroso compounds, and styrene derivatives. The tertiary amines include triethylamine, tributylamine, N, N-diethylbutylamine, N, N-diethyl-t-octylamine, N, N-diisopropylethylamine, N, N-diisopropylisobutylamine, N, N- Trialkylamines such as diisopropyl-1-ethylpropylamine, N, N-diisopropyl-2-ethylbutylamine, N-methyldicyclohexylamine, N-ethyldicyclohexylamine, and N, N-diethyl-t-octylamine; N Hydroxyl group-containing trialkylamines such as N, N-dimethylethanolamine, N-methyldiethanolamine, and triethanolamine; and N, N-dimethylbenzylamine, N, N-diethylbenzylamine, methyl dimethylaminobenzoate, Aryl amines such as tribenzylamine, etc. and the like. Examples of the styrene derivative include α-methylstyrene dimer (2,4-diphenyl-4-methyl-1-pentene). Examples of the thiols include 1-butanethiol and n-dodecyl mercaptan.
Preferable specific examples of component 6 include tertiary amines, thiols, and styrene derivatives, more preferably tertiary amines and styrene derivatives, and particularly preferably styrene derivatives. The tertiary amine is a low molecular weight molecule having a molecular weight of 50 to 250, and preferably does not have a reactive group such as OH, NH .sub.2 or SH. In the volume phase hologram recording material composition of the present invention, the amount of component 6 is preferably 5 parts or less, more preferably 0.01 to 5 parts, particularly preferably 100 parts of component 1. Is 0.1 to 3 parts. When the blending amount of component 6 is within this range, hologram recording and reproduction can be performed with low noise and high sensitivity in the recording material [0047-0049]. Component 4 is preferably an addition photopolymerizable monomer, such as a radical photopolymerizable monomer or a cationic photopolymerizable monomer, and preferably a radical photopolymerizable monomer. Component 4 is preferably a monofunctional or polyfunctional photopolymerizable monomer, more preferably a monofunctional photopolymerizable monomer. Component 4 includes (meth) acrylates, (meth) acrylamides, styrenes, substituted styrenes, vinyl monomers, vinyl naphthalenes, and substituted vinyl naphthalenes having radically polymerizable ethylenic double bonds. Is preferable. Among these, (meth) acrylates are more preferable for the present invention because of their high polymerization rate. In addition, (meth) acrylate shows acrylic acid ester and / or methacrylic acid ester, and (meth) acrylamide etc. are the same. In the present invention, the difference in refractive index between the polymer matrix and the component 4 is preferably 0.0001 or more, more preferably 0.0003 or more, and further preferably 0.0005 or more. Further, the difference is preferably 0.2 or less, more preferably 0.18 or less, and still more preferably 0.15 or less. When the difference exceeds 0.2, the balance between the polymer matrix and the component 4 in the recording material may be lost, which is not preferable. Also, if the difference is less than 0.0001, the refractive index modulation is poor and the bit error rate may be increased, which is not preferable. The refractive index is measured at 25 ° C., preferably measured at the same wavelength as the reference light [0027-0032]. Component 1 includes low molecular weight polyols, polyether polyols, polyester polyols, polycaprolactones, polycarbonate diols, and the like [0041].
Weiser et al. 20140295328 in example 11 (see table on page 14), combines polyol 1, isocyanate 1, two writing monomers, experimental additive 1, New Methylene Blue 0.10% with CGI 909 (product from BASF SE, Basle, Switzerland) 1.0%, as solution in N-ethylpyrrolidone (photoinitiator), and urethane catalyst dimethylbis[(1-oxoneodecl)oxy]stannane and Chain transfer agent 12 (3,6-dioxa-1,8-octadithiol, obtained from Sigma-Aldrich Chemie GmbH, Steinheim, Germany [0158]. To produce holographic media, the writing monomers B), the stabilizers, which might already have been predissolved in component B), and also optionally the auxiliary and admixture agents were dissolved in the employed polyol (isocyanate-reactive component b)) optionally at 60.degree. C. and thoroughly mixed. Thereafter, in the dark or under suitable illumination, the photoinitiator(s) C) and also the chain transfer agent(s) E) was/were weighed in and again mixed in for one minute to obtain a clear solution. Then, the isocyanate component a) was added which was again followed by mixing for 1 minute. The liquid mass obtained was then applied to substrate foil 1 and dried at 80.degree. C. for 4.5 minutes. Dry layer thickness was determined [0211]. To measure the holographic performance of the holographic film, the protective foil is peeled off and the holographic film is laminated with the photopolymer side onto a 1 mm thick glass plate of suitable length and width by applying a rubber roll under light pressure. This sandwich of glass and photopolymer foil can then be used to determine the holograph performance parameters DE and .DELTA.n. The beam of an He--Ne laser (emission wavelength 633 nm) was transformed via the spatial filter (SF) and together with the collimation lens (CL) into a parallel homogeneous beam. The final cross sections of the signal and reference beams are fixed via the iris diaphragms (I). The diameter of the iris diaphragm opening is 0.4 cm. The polarization-dependent beam splitters (PBS) split the laser beam into two coherent identically polarized beams. Via the .lamda./2 plates, the power of the reference beam was adjusted to 0.5 mW and the power of the signal beam to 0.65 mW. The powers were determined using the semiconductor detectors (D) with sample removed. The angle of incidence (.alpha..sub.0) of the reference beam is -21.8.degree. and the angle of incidence (.beta..sub.0) of the signal beam is 41.8.degree.. The angles are measured from the sample normal to the beam direction. According to FIG. 1, therefore, .alpha..sub.0 has a negative sign and .beta..sub.0 has a positive sign. At the location of the sample (medium), the interference field of the two overlapping beams produced a grating of light and dark strips which are perpendicular to the angle bisector of the two beams incident on the samples (reflection hologram). The strip spacing .LAMBDA., also referred to as grating period, in the medium is .about.225 nm (the refractive index of the medium is assumed to be .about.1.504) [0176-0177]. It is very particularly preferable for the chain transfer agents used to be thiols, especially primary or multifunctional secondary thiols, esters and peroxides. Examples of particularly preferred compounds of the classes recited herein are n-octylthiol, n-hexylthiol, n-decylthiol, n-dodecylthiol, 11,11-dimethyldodecane-1-thiol, 2-phenylethyl mercaptan, 1,8-dithionaphthalene, octane-1,8-dithiol, 3,6-dioxa-1,8-octanedithiol, cyclooctane-1,4-dithiol, 3-methoxybutyl 3-mercaptopropionate, butyl 3-mercaptopropionate, 2-ethylhexyl thioglycolate, 2-hydroxyethyl 3-mercaptopropionate, iso-octyl 3-mercaptopropionate, n-octyl 3-mercaptopropionate, n-propyl 3-mercaptopropionate, dodecyl 3-mercaptopropionate, 2-ethylhexyl 3-mercaptopropionate, isooctyl thioglycolate, isotridecyl thioglycolate, glycol di(3-mercaptopropionate), ethyl 2-mercaptopropionate, ethyl 3-mercaptopropionate, glycol dimercaptoacetate, pentaerythritol tetrakis(mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), pentaerythritol tetrakis(2-mercaptopropionate), trimethylolpropane tris(2-mercaptoacetate), trimethylolpropane tris(3-mercaptopropionate), trimethylolpropane tris(2-mercaptopropionate), methyl furfurylmercaptopropionate, 1,4-bis(3-mercaptobutylyloxy)butane, 1,3,5-tris(3-mercaptobutyloxyethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-triones, pentaerythritol tetrakis(3-mercaptobutylate), 2,2'-[ethane-1,2-diylbis(oxy)]diethanethiol, 2,2'-oxydiethanethiol, 2-thionaphthol, mercaptobenzothiazole, 2-mercaptobenzoxazole, mercaptobenzimidazole, 4-methylbenzyl mercaptan, 2-mercaptoethyl sulphide, bis(phenylacetyl) disulphide, dibenzyl disulphide, di-tert-butyl disulphide, phenothiazine, N-phenylglycine ethyl ester, N-phenylglycine, di-tert-butyl peroxide, dicumyl peroxide, dibenzoyl pero1xide, tert-butyl peroxy-2-ethylhexanoate, lauryl peroxide, bis(tertbutylcyclohexyl) peroxydicarbonate, tert-butyl-3,5,5-trimethyl peroxyhexanoate, triphenylmethanethiol, triphenylmethanol, 1,1-dimethyl-3,5-diketocyclohexane, 1-bromo-2-(1,1-dimethoxyethyl)benzene, acetone di-n-butyl acetal, 1,3,3-trimethoxybutane, methyl 4,4-dimethoxypentanoate, acetophenone dimethyl ketal, chlorotriphenylmethane, bromotriphenylmethane, triphenylmethane, isopropylbenzene, carbon tetrachloride, carbon tetrabromide, chloroform and other aliphatic chlorohydrocarbons. In a further preferred embodiment of the photopolymer formulation of the invention, it comprises less than 2.5 wt %, preferably 0.05-1.01 wt %, and more preferably 0.09-0.55 wt % of the chain transfer agent E), based on the photopolymer formulation [0011-0012]. Preferred components for the inner block Y are polymers of tetrahydrofuran and aliphatic polycarbonatepolyols and polyesterpolyols and polymers of .epsilon.-caprolactone having number average molar masses of less than 3100 g/mol [0070]
Kosaka 20030194487 teaches the reaction of polyols and polythiols in the presence of a catalyst to form thiourethanes [0008,0015]. The high refractive index compositions are used in the production of optical articles such as eyeglass lenses [0003-0006]. Non-limiting examples of the polythiol compound include compounds having sulfur other than that in a mercapto group, such as methanedithiol, ethanedithiol, propanedithiol, 1,6-hexanedithiol, 1,2,3-propanetrithiol, tetrakis(mercaptomethyl) methane, cyclohexanedithiol, 2,2-dimethylpropane-1,3-dithiol, 3,4-dimethoxybutane-1,2-dithiol, 2-methylcyclohexane-2,3-dithiol, bis(mercaptomethyl)cyclohexane, 2,3-dimercapto-1-propanol(2-mercaptoaceta- te), 2,3-dimercapto-1-propanol (3-mercaptoacetate), diethylene glycol bis(2-mercaptoacetate), diethylene glycol bis(3-mercaptopropionate), 1,2-dimercaptopropyl methyl ether, 2,3-dimercaptopropyl methyl ether, 2,2-bis(mercaptomethyl)-1,3-propanedithiol, bis(2-mercaptoethyl) ether, ethylene glycol bis(2-mercaptoacetate), ethylene glycol bis(3-mercaptopropionate), trimethyloylpropane tris(2-mercaptoacetate), trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), 1,2-bis(2-mercaptoethylthio)-3-mercaptopropane, bis(mercaptomethyl) sulfide, bis(mercaptoethyl) sulfide, bis(mercaptopropyl) sulfide, bis(mercaptomethylthio)methane, bis(2-mercaptoethylthio)methane, bis(3-mercaptopropyl) methane, 1,2-bis(mercaptomethylthio)ethane, 1,2-(2-mercaptoethylthio)ethane, 1,2-(3-mercaptopropyl)ethane, 1,3-bis(mercaptomethylthio) propane, 1,3-bis(2-mercaptoethylthio)propane, 1,3-bis(3-mercaptopropylthio)propane, 1,2-bis(2-mercaptoethylthio)-3-mercaptopropane, 2-mercaptoethylthio-1,3-propanedithiol, 1,2,3-tris(mercaptomethylthio)propane, 1,2,3-tris(2-mercaptoethylthio)pro-pane, 1,2,3-tris(3-mercaptopropylthio)propane, tetrakis(mercaptomethylthio- methyl)methane, tetrakis(2-mercaptoethylthiomethyl)methane, tetrakis(3-mercaptopropylthio methyl)methane, bis(mercaptomethyl) disulfide, bis(mercaptoethyl) disulfide, bis(mercaptomethyl)-3,6,9-trithi- a-1,11 -undecanedithiol, bis(1,3-dimercapto-2-propyl) sulfide, 3,4-thiophenedithiol, tetrahydrothiophene-2,5-dimercaptomethyl, 2,5-dimercapto-1,3,4-thiadiazole, 2,5-dimercapto-1,4-dithiane, 2,5-bis(mercaptomethyl)-1,4-dithiane, and 2,5-bis(mercaptoethyl)-1,4-dithiane [0018].
Hamaide et al. JP 2014-044242 (machine translation attached) in example 1 combines Polyacrylic acid ester; Dianal BR-605 (thermoplastic resin, manufactured by Mitsubishi Rayon Co., Ltd., weight average molecular weight; 50000): 70 parts by mass Epoxy group-containing acrylic resin; Dianal VB-7201 (thermosetting Resin, manufactured by Mitsubishi Rayon Co., Ltd., weight average molecular weight: 43000, epoxy equivalent: 1238 g / eq) 30 parts by mass • diphenoxyethanol fluorene acrylate; BPEFA (photo radical polymerizable monomer, manufactured by Osaka Gas Chemical Co., Ltd.) 100 parts by mass-1,6-hexanediol diglycidyl ether; 71.4 parts by mass of Denacol EX-212 (photocation polymerizable monomer, manufactured by Nagase ChemteX Corp.)-Diaryl iodonium salt; PI 2074 (photopolymerization initiator) 11.4 parts by mass, 2,5- (4-diethylaminobenzylidene) cyclopentanone; (sensitizing dye) 2.9 parts by mass Pentaerythritol tetrakis (3-mercaptopropionate); trade name PETP (tetrafunctional primary thiol compound, Sakai Chemical Co., Ltd.) Manufactured) 1.5 parts by mass-methyl isobutyl ketone (solvent) 285.7 parts by mass-1-butanol (solvent) 285.7 parts by mass. Production of photosensitive substrate for volume hologram recording The photosensitive composition 1 for volume hologram recording obtained in (1) is placed on a 50 μm polyethylene terephthalate (PET) film (Toray Lumirror T-60). Using an applicator, coating and drying were carried out so that the film thickness after drying was 10 μm to obtain a hologram recording layer, whereby a volume type hologram recording photosensitive substrate 1 of Example 1 was obtained. (3) Manufacture of volume hologram recording body The hologram recording layer side of the volume hologram recording photosensitive substrate of Example 1 obtained in (2) is laminated on a mirror, and PET of the volume hologram recording photosensitive substrate is obtained. A 532 nm laser beam was incident from 10 to 100 mJ / cm .sup.2 from the side, interference exposure was performed, and a volume hologram was recorded. At that time, the incident angle of the laser beam to the hologram recording layer was an angle of 0 degrees of the hologram. After recording, the photosensitive substrate for volume hologram recording was peeled off from the mirror, and a 38 μm polyethylene terephthalate (PET) film (A4300; manufactured by Toyobo Co., Ltd.) was laminated on the hologram recording layer side. Next, heating at 80 ° C. for 30 minutes, irradiating the entire surface with ultraviolet rays, fixing the hologram recording layer, further irradiating green light near 530 nm for 100 minutes, decolorizing the sensitizing dye, and hologram having interference fringes recorded A volume hologram recording body 1 of Example 1 having a layer was obtained [0097-0099]. Specific examples of the polyfunctional primary thiol compound include hexanedithiol, decanedithiol, ethylene glycol bisthioglycolate, 1,4-butanediol bisthioglycolate, trimethylolpropane tristhioglycolate, pentaerythritol. Tetrakisthioglycolate, ethylene glycol bis (3-mercaptopropionate), 1,2-propylene glycol bis (3-mercaptopropionate), 1,3-propylene glycol bis (3-mercaptopropionate), 1 , 4-butanediol bis (3-mercaptopropionate), glycerin tris (3-mercaptopropionate), trimethylolpropane tris (3-mercaptopropionate), trimethylolethane tris (3-mer) Hept propionate), pentaerythritol tetrakis (3-mercaptopropionate), dipentaerythritol hexakis (3-mercaptopropionate) and the like. In the present invention, the thiol group-containing compound used as an essential component is a polyfunctional primary thiol compound having two or more primary thiol groups in at least one molecule, and is used as a chain transfer agent for a photoradically polymerizable monomer. It is done. In the photosensitive composition for volume hologram recording of the present invention, the content of the thiol group-containing compound is 1.5 to 30 masses of the thiol group-containing compound with respect to 100 mass parts of the photoradical polymerizable monomer described later. Part. In such a range, the reaction rate of the photo-radically polymerizable monomer can be increased to such an extent that the movement of the monomer is not inhibited, so that the sensitivity during hologram recording and the refractive index modulation amount (Δn) at a low exposure amount are high. A photosensitive composition for volume hologram recording can be obtained. Moreover, since it is the optimal addition amount which does not inhibit the decolorization of a sensitizing dye, the photosensitive composition for volume type hologram recording with the favorable decoloring property of a sensitizing dye can be obtained [0023-0034]. As the radical photopolymerizable monomer used in the present invention, when a hologram recording layer is formed using the photosensitive composition for volume hologram recording of the present invention, a radical photopolymerization initiator described later, for example, by laser irradiation or the like. Although it will not specifically limit if it is a compound polymerized by the action of the active radical generated from, it is preferable to use a compound having at least one ethylenically unsaturated double bond in the molecule. For example, unsaturated carboxylic acid, unsaturated carboxylate, ester of unsaturated carboxylic acid and aliphatic polyhydric alcohol compound, amide bond of unsaturated carboxylic acid and aliphatic polyhydric amine compound, etc. can be mentioned [0036].
It would have been obvious to one skilled in the art to modify example 1 of Sasaki et al. JP 2008268520 adding bis(mercaptoethyl) sulfide or 1,2-bis(2-mercaptoethylthio)-3-mercaptopropane taught by Kosaka 20030194487 either to be incorporated into the backbone of the (thio)urethane matrix polymer as taught by Hamaide et al. JP 2014-044242 and/or as a chain transfer agent to control the polymerization of the monomer [2,4-bis(2-naphthylthio)-2-butylacrylate] as taught by Weiser et al. 20140295328 with a reasonable expectation of forming a useful holographic recording composition.
In the arguments of 11/11/2025, the applicant argues without any support that it is not known to substitute dithiols for thiol in the polymer art. The examiner points out that the compositions of Sasaki et al. JP 2008268520 are originally two separate solutions of the matrix precursors, monomers, chain transfer agents and photoinitiators which are mixed and result in the formation of the urethane polymer matrix in the presence of the monomers, chain transfer agents and photoinitiators. It is clearly appreciated in the references that the thiol moieties react with isocyanate moieties to form thiourethanes and this would inherently occur in the composition in the presence of polyols during the formation of increasing amounts of the matrix polymer (the allyl containing polyurethane, until the composition recited amounts of the allyl containing polyurethane, the intermediate composition (before the matrix polymer formation is finished) as well as the composition when the matrix polymerization is complete is held to meet the claims). The Also the use of dithiols and monothiols as chain transfer agents to control free radical polymerization is clearly taught in Weiser et al. 20140295328. The rejection stands.
Claims 1,2,5-9,13,14,16,18-21 are rejected under 35 U.S.C. 103 as being unpatentable over Sasaki et al. JP 2008268520, in view of Kosaka 20030194487, Weiser et al. 20140295328 and Hamaide et al. JP 2014-044242, further in view of Alim et al. WO 2019237117.
Alim et al. WO 2019237117 teaches the use of monomers bounded by formula (I) in holographic compositions
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, wherein, each instance of Y is independently O, S, or NH; each instance of R.sup.1 and R.sup.2 is independently selected from the group consisting of optionally substituted C.sub.6-C.sub.18 aryl, optionally substituted C.sub.5-C.sub.18 heteroaryl, and C.sub.1-C.sub.3 alkyl optionally substituted with 1-6 independently selected C.sub.6-C.sub.10 aryl groups; R.sup.3 is selected from the group consisting of optionally substituted C.sub.2-C.sub.15 alkenyl, optionally substituted C.sub.2-C.sub.15 heteroalkenyl, optionally substituted C.sub.2-C.sub.15 alkynyl, optionally substituted C.sub.2-C.sub.15 heteroalkynyl, optionally substituted —C(═O)—C.sub.2-C.sub.15 alkenyl, optionally substituted —C(═O)—C.sub.2-C.sub.15 alkynyl, optionally substituted —C(═O)—C.sub.3-C.sub.10 cycloalkenyl, optionally substituted C.sub.3-C.sub.10 cycloalkenyl, and optionally substituted C.sub.3-C.sub.10 heterocycloalkenyl; and [0072] x is an integer ranging from 1 to 4 [0068-0072]. Exemplified monomers include
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It would have been obvious to one skilled in the art to modify example 1 of Sasaki et al. JP 2008268520 by replacing at least a portion of the 2,4-dibromophenyl acrylate with the monomer
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taught as useful in holographic recording by Alim et al. 20210246266 WO 2019237117 and adding bis(mercaptoethyl) sulfide or 1,2-bis(2-mercaptoethylthio)-3-mercaptopropane taught by Kosaka 20030194487 either to be incorporated into the backbone of the (thio)urethane matrix polymer as taught by Hamaide et al. JP 2014-044242 and/or as a chain transfer agent to control the polymerization of the monomer [2,4-bis(2-naphthylthio)-2-butylacrylate] as taught by Weiser et al. 20140295328 with a reasonable expectation of forming a useful holographic recording composition.
The applicant did not advance and further arguments and the examiner relies upon the response above without further comment.
Claims 1,2,5-9,13,14,16,18-21 are rejected under 35 U.S.C. 103 as being unpatentable over Sasaki et al. JP 2008268520, in view of Kosaka 20030194487, Weiser et al. 20140295328 and Hamaide et al. JP 2014-044242, further in view of Settachayanon et al. 20030224250 and Wendland et al. 20070297944.
Settachayanon et al. 20030224250 exemplifies in example 1, isocyanate baytech WE-180, 2,4-bis(2-naphthylthio)-2-butylacrylate, iracure 784 (photoinitiator), butyrated hydroxytoluene (thermal stabilizer) and in a second container Polypropylene Oxide Triol, t-Butylperoxide 310 and Dibutyltindilaurate. The monomers can be those bounded by
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where R can be phenyl, mono or multi-substituted phenyls, bromophenyl, or naphthalene group; R.sub.1 and R.sub.3 can be methylene, ethylene, propylene, or butylene group; R.sub.2 can be H, or alkyl group; R.sub.3 can be -COCH=CH2, -COCCH=CH2, or -CH=CH2 [0049-0050].
Wendland et al. 20070297944 teaches free radically polymerizable groups which are ethyleneically unsaturated including vinyl, vinyloxy, (meth)acrylic, (meth)acryloyl, (meth)acryloxy, propargyl, (meth)acrylamido groups, and acetylenic functional groups) [0070]
It would have been obvious to one skilled in the art to modify example 1 of Sasaki et al. JP 2008268520 by replacing at least a portion of the 2,4-dibromophenyl acrylate with the monomer
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which is the propargyl analogue of the monomers of Settachayanon et al. 20030224250 noting that Wendland et al. 20070297944 establishes the equivalence of acrylate and propargyl as polymerizable moieties and adding bis(mercaptoethyl) sulfide or 1,2-bis(2-mercaptoethylthio)-3-mercaptopropane taught by Kosaka 20030194487 either to be incorporated into the backbone of the (thio)urethane matrix polymer as taught by Hamaide et al. JP 2014-044242 and/or as a chain transfer agent to control the polymerization of the monomer [2,4-bis(2-naphthylthio)-2-butylacrylate] as taught by Weiser et al. 20140295328 with a reasonable expectation of forming a useful holographic recording composition. With respect to claim 28, i, ii and iii are met.
The applicant did not advance and further arguments and the examiner relies upon the response above without further comment.
Claims 1,2,5-9,13,14,16,18-21 are rejected under 35 U.S.C. 103 as being unpatentable over Sasaki et al. JP 2008268520, in view of Kosaka 20030194487, Weiser et al. 20140295328 Hamaide et al. JP 2014-044242, Settachayanon et al. 20030224250 and Wendland et al. 20070297944 and further in view of Stockel et al. 20090062419.
Stockel et al. 20090062419 exemplifies poly (.epsilon.-caprolactone)-block-poly(tetrahydrofuran)-block-poly(.epsilon.-caprolactone)polyols in block copolymers B and C [0083-0084]. These are used in holographic polyurethane formation C and D [0088-0089].
Esters of acrylic acid or methacrylic acid are generally referred to as acrylates or methacrylates. Examples of acrylates and methacrylates which may be used are methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, ethoxyethyl acrylate, ethoxyethyl methacrylate, n-butyl acrylate, n-butyl methacrylate, tert-butyl acrylate, tert-butyl methacrylate, hexyl acrylate, hexyl methacrylate, 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, butoxyethyl acrylate, butoxyethyl methacrylate, lauryl acrylate, lauryl methacrylate, isobornyl acrylate, isobornyl methacrylate, phenyl acrylate, phenyl methacrylate, p-chlorophenyl acrylate, p-chlorophenyl methacrylate, p-bromophenyl acrylate, p-bromophenyl methacrylate, trichlorophenyl acrylate, trichlorophenyl methacrylate, tribromophenyl acrylate, tribromophenyl methacrylate, pentachlorophenyl acrylate, pentachlorophenyl methacrylate, pentabromophenyl acrylate, pentabromophenyl methacrylate, pentabromobenzyl acrylate, pentabromobenzyl methacrylate, phenoxyethyl acrylate, phenoxyethyl methacrylate, phenoxyethoxyethyl acrylate, phenoxyethoxyethyl methacrylate, 2-naphthyl acrylate, 2-naphthyl methacrylate, 1,4-bis-(2-thionaphthyl)-2-butyl acrylate, 1,4-bis-(2-thionaphthyl)-2-butyl methacrylate, bisphenol A diacrylate, bisphenol A dimethacrylate, tetrabromobisphenol A diacrylate, tetrabromobisphenol A dimethacrylate, 2,2,2-trifluoroethyl acrylate, 2,2,2-trifluoroethyl methacrylate, 1,1,1,3,3,3-hexafluoroisopropyl acrylate, 1,1,1,3,3,3-hexafluoroisopropyl methacrylate, 2,2,3,3,3-pentafluoropropyl acrylate and/or 2,2,3,3,3-pentafluoropropyl methacrylate. Epoxy acrylates also suitable as component C) can be obtained as reaction products of bisphenol A diglycidyl ether with hydroxyalkyl (meth)acrylates and carboxylic acids, the bisphenol A diglycidyl ether first being reacted with hydroxyalkyl (meth)acrylate with catalysis by Lewis acid and this hydroxyl-functional reaction product then being esterified with a carboxylic acid by a method known to the person skilled in the alt. Bisphenol A diglycidyl ether itself and brominated variants, such as, for example, tetrabromobisphenol A diglycidyl ether (from Dow Chemical, D.E.R. 542), can advantageously be used as the diepoxide. All hydroxyl-functional acrylates described above can be used as hydroxyalkyl (meth)acrylates, in particular 2-hydroxyethyl acrylate, hydroxypropyl acrylate, 4-hydroxybutyl acrylate, poly(.epsilon.-caprolactone) mono (meth)acrylates and poly(ethylene glycol) mono(meth)acrylates. All monofunctional carboxylic acids are in principle suitable as the carboxylic acid, in particular those having aromatic substituents. Propane-2,2-diylbis[(2,6-dibromo-4,1-phenylene)oxy(2-{[3,3,3-tris(4-chlor- ophenyl)propanoyl]oxy}propane-3,1-diyl)oxyethane-2,1-diyl]diacrylate has proved to be a preferred compound of this class of epoxy acrylates. Vinylaromatics suitable for component C) are styrene, halogenated derivatives of styrene, such as, for example, 2-chlorostyrene, 3-chlorostyrene, 4-chlorostyrene, 2-bromostyrene, 3-bromostyrene, 4-bromostyrene, p-(chloromethyl)styrene, p-(bromomethyl)styrene or 1-vinylnaphthalene, 2-vinylnaphthalene, 2-vinylanthracene, N-vinylpyrrolidone, 9-vinylanthracene, 9-vinylcarbazole or difunctional compounds, such as divinylbenzene. Vinyl ethers, such as, for example, butyl vinyl ether, are also suitable [0048-0049]
It would have been obvious to one skilled in the art to modify the compositions rendered obvious by the combination of Sasaki et al. JP 2008268520, Kosaka 20030194487, Weiser et al. 20140295328 Hamaide et al. JP 2014-044242, Settachayanon et al. 20030224250 and Wendland et al. 20070297944 by adding another matrix/binder such as the poly (.epsilon.-caprolactone)-block-poly(tetrahydrofuran)-block-poly(.epsilon.-caprolactone)polyols in block copolymers B and C of Stockel et al. 20090062419 with a reasonable expectation of forming a useful holographic composition based upon their prior use in them.
The applicant did not advance and further arguments and the examiner relies upon the response above without further comment.
THIS ACTION IS MADE FINAL. Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to 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 November 20, 2025
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