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 to the restriction requirement has been received and made of record. The restriction requirement is repeated for completeness and made final.
REQUIREMENT FOR UNITY OF INVENTION
As provided in 37 CFR 1.475(a), a national stage application shall relate to one invention only or to a group of inventions so linked as to form a single general inventive concept (“requirement of unity of invention”). Where a group of inventions is claimed in a national stage application, the requirement of unity of invention shall be fulfilled only when there is a technical relationship among those inventions involving one or more of the same or corresponding special technical features. The expression “special technical features” shall mean those technical features that define a contribution which each of the claimed inventions, considered as a whole, makes over the prior art.
The determination whether a group of inventions is so linked as to form a single general inventive concept shall be made without regard to whether the inventions are claimed in separate claims or as alternatives within a single claim. See 37 CFR 1.475(e).
When Claims Are Directed to Multiple Categories of Inventions:
As provided in 37 CFR 1.475 (b), a national stage application containing claims to different categories of invention will be considered to have unity of invention if the claims are drawn only to one of the following combinations of categories:
(1) A product and a process specially adapted for the manufacture of said product; or
(2) A product and a process of use of said product; or
(3) A product, a process specially adapted for the manufacture of the said product, and a use of the said product; or
(4) A process and an apparatus or means specifically designed for carrying out the said process; or
(5) A product, a process specially adapted for the manufacture of the said product, and an apparatus or means specifically designed for carrying out the said process.
Otherwise, unity of invention might not be present. See 37 CFR 1.475 (c).
Restriction is required under 35 U.S.C. 121 and 372.
This application contains the following inventions or groups of inventions which are not so linked as to form a single general inventive concept under PCT Rule 13.1.
In accordance with 37 CFR 1.499, applicant is required, in reply to this action, to elect a single invention to which the claims must be restricted.
Group I, claims 17-20, drawn to a photosensitive composition including a urethane acrylate, bisphenol A diacrylate and a dye/borate photoinitiator.
Group II, claims 21-25, drawn to a cured composition from a photosensitive composition which included, including a urethane acrylate, bisphenol A diacrylate and a dye/borate photoinitiator
Group III, claims 26-30, drawn to a process of exposing a composition which may include a temperature over 100 degrees C and pressure of more than 2 Bar
The groups of inventions listed above do not relate to a single general inventive concept under PCT Rule 13.1 because, under PCT Rule 13.2, they lack the same or corresponding special technical features for the following reasons:
A composition including a 50 wt% of a bisphenol A diacrylate, 30 wt% of an aliphatic urethane acrylate, 20 wt% of naphthoxyethyl acrylate and irgacure 184 (1-hydroxycyclohenylphenyl ketone) as the photoinitiator is exemplified in WO 2017047547, which was cited in the search report of April 12, 2022.
Sugita JP H10287450 (machine translation attached) in inventive example 1, combines 100 g of pentaerythritol triacrylate, 0.1 g of a near-infrared light-absorbing cationic dye (Table 1, No. 3, n-butyltriphenylboron anion) and a boron-based catalyst ( Tetrabutylammonium / n-butyltriphenylboron) 0.5g of the photocurable composition 1 obtained by dissolving, a glass plate having a size of 30 cm × 30 cm was coated with an applicator to a thickness of 100 μm, and a glass plate of the same size was laminated thereon. By irradiating a halogen lamp with an output of 1500 W having a spectral distribution in a wavelength region of 400 to 1200 nm for 10 minutes, the blue color of the near-infrared light-absorbing dye is erased and the curable composition between the glasses is photo-cured, and colorless. A laminated glass having a transparent resin intermediate layer was obtained [0053].
(Comparative Example 1) 5 g of Irgacure 184 (manufactured by Ciba-Geigy), which is an ultraviolet light initiator, was changed to a combination of a cationic dye and a boron compound as a polymerization initiator. A functional glass was produced in the same manner as in Example 1 except for using. For light irradiation, a high-pressure mercury lamp having a spectral distribution in a wavelength region of 200 to 400 nm was used. By irradiation for 5 minutes, the curable composition between the glasses was photocured, but the red dye used as the colorant was decomposed and faded, and only unclear colored laminated glass was obtained [0061].
Kishi JP H0860044 (machine translation attached) in inventive Example 6 combines
Phenylborane-n-butylammonium/ Cyanine dye salt with a filler (150 parts by weight of crown talc) were added to a binder resin (40 parts by weight of epoxy acrylate, 60 parts by weight of isobornyl acrylate), and they were sufficiently kneaded with a three-roll mill. 7 cm of this putty A 5 cm x 5 cm area with a thickness of 10 mm is built up on a 20 cm iron plate and irradiated with a 300 W halogen lamp, a 1.5 kW xenon lamp, and a 150 W infrared lamp at an irradiation distance of 20 cm for complete curing [0035,0041] Comparative example 2 was similar but used Irgacure 184 as the photoinitiator [0043]. Curing times (minutes) inventive composition 6 are 7,2, and 5 minutes under the different exposure sources), while the composition of example 2 does not cure or is limited to thicknesses of 1mm or less [0050-0051].
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Sugita et al. JP-H07228798 (machine translation attached) in inventive examples 1 combines Pentaerythritol triacrylate-Hexamethylene diisocyanate-urethane prepolymer 70 g, nonaethylene glycol diacrylate After thoroughly mixing 30 g, a near infrared absorbing dye (Table 1 Complex No. 3, anion is n-butyltriphenylboron anion) 0.1 g Boron sensitizer tetrabutylammonium n-butyltriphenylboron 0.1 g, dye for coloring (azo chemical red dye manufactured by Orient Chemical Co., Ltd [0038].
Comparative Example 1 The same as Example 1 except that 3.0 g of an ultraviolet photopolymerization initiator (trade name Irgacure 184 manufactured by Ciba-Geigy) was used in place of the near infrared absorptive dye and the boron compound. Comparative sample 1 was prepared [0047]
(Comparative Example 2) The same as Example 3 except that 3.0 g of an ultraviolet photopolymerization initiator (trade name Irgacure 184 manufactured by Ciba-Geigy Co., Ltd.) was used instead of the near-infrared light absorbing dye and the boron compound. Comparative sample 2 was prepared [0048].
The color in the comparative examples changes the color relative to the dye for coloring in the cured film as evidenced in the DL, Da and Db values.
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Claim 16-30 lack unity of invention because even though the inventions of these groups require the technical feature of the photoinitiator system, this technical feature is not a special technical feature as it does not make a contribution over the prior art in view of WO 2017047547 (a Y reference) in combination with any of Sugita JP H10287450, Kishi JP H0860044 or Sugita et al. JPH07228798 Y reference), which establish the higher sensitivity and the low coloration in the cured product when dye/borate photoinitiators are used.
Therefore any feature which unites these inventions fails to confer patentability.
A telephone call was made to Brian J Jackson in a companion application to request an oral election to the above restriction requirement, but did not result in an election being made. The examiner was informed that this applicant wished to receive written restrictions.
Applicant is advised that the reply to this requirement to be complete must include (i) an election of a species or 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 or species may be made with or without traverse. To preserve 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 on the elected invention or species.
Should applicant traverse on the ground that the inventions have unity of invention (37 CFR 1.475(a)), applicant must provide reasons in support thereof. Applicant may 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. Where such evidence or admission is provided by applicant, 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.
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 of Group I in the reply filed on 6/2/2026 is acknowledged. Because applicant did not distinctly and specifically point out the supposed errors in the restriction requirement, the election has been treated as an election without traverse (MPEP § 818.01(a)).
Claims 21-30 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected inventions, there being no allowable generic or linking claim. Election was made without traverse based upon and incomplete response in the reply filed on 6/2/2026.
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claim 20 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
In claim 20, “urethanediacrylate” should read - - urethane diacrylate - - (both occurrences)
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 16-17 and 19-20 are rejected under 35 U.S.C. 103 as being unpatentable over Hunziker et al. CA 2028541.
Hunziker et al. CA 2028541 teaches liquid mixtures containing a) 5-25 % by weight of a monomeric aliphatic or cycloaliphatic di(meth)acrylate having a molecular weight (MW) of not more than 800, b) 0-15 % by weight of a monomeric poly(meth)acrylate having a functionality of at least 3 and an MW of not more than 600, c) 0-20 % by weight of a mono(meth)acrylate or a mono-N-vinyl compound having an MW of not more than 500, d) 20-60 % by weight of a urethane (meth)acrylate having a functionality of 2 to 4 and an MW of 500 to 10,000, e) 10-50 % by weight of a monomeric or oligomeric di(meth)acrylate based on bisphenol A or bisphenol F, f) 0.1-10 % by weight of a photoinitiator and g) 0-5 % by weight of customary additives, the proportion of the components a) to g) together being 100 % by weight, are photosensitive mixtures which can be polymerized by means of actinic radiation and are preferentially suitable for the production of three-dimensional articles by means of the stereolithographic process (abstract). Example 1 combines 39.75 g of ethoxylated bisphenol A diacrylate (MW = 424, product SR-349 of the SARTOMER Company 39.75 wt%) are mixed at 40°C with 40.02 g of urethane acrylate (MW =1700, product SR 9504 of the SARTOMER Company, 40.02 wt%), 3.25 g of 1,1,1- Trimethylolpropane triacrylate (MW = 408, 3.25 wt%), 12.99 g of 1,4-butanediol diacrylate (MW = 198, 12.99 wt%) and 4 g of 1-hydroxycyclohexyl phenyl ketone (4 wt%). The resulting homogeneous liquid mixture has a viscosity of 1510 mPa.s at 30°C. The curl factor of a three-dimensional shaped article built up from individual layers (layer thickness = 0.305 mm) and prepared with an HeCd laser is 1.05. The so-called green shaped article, cured by means of laser radiation, has an elastic modulus of 20 N/mm2, a tensile strength of 2.4 N/mm2 and an elongation at break of 13 %. After the green shaped article has been cured for 30 minutes under UV/VIS light by means of an Hg lamp, the green strength is 1500 N/mm2, the tensile strength is 40 N/mm2 and the elongation at break is 7 to 19 % (page 10). Examples 2-7: Mixtures are prepared as in Example 1 by mixing the components Indicated in Table 1 below and are processed to give three-dimensional shaped articles under the conditions indicated in Example 1. The properties of the shaped articles obtained are also shown in Table 1 (page 10). The compositions of examples 2-9 and 14-25 are similar.
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Another class of suitable photoinitiators (f) is constituted by the ionic dye-counter ion compounds which are capable of absorbing actinic radiation and producing free radicals which initiate the polymerization of the acrylates (a) to (e) or the mono-N-vinyl compound (c). The mixtures according to the invention containing ionic dye-counter ion compounds can be cured in a fairly variable manner in this way with visible light within the adjustable wavelength range of 400-700 nm. Ionic dye-counter ion compounds and their mode of action are known, for example from EP-A-0,223,587 and US Patents 4,751,102; 4,772,530 and 4,772,541. Examples of suitable ionic dye-counter ion compounds which may be mentioned are the anionic dye-iodonium ion complexes, the anionic dye-pyrylium ion complexes and, especially, the cationic dye-borate anion compounds of the formula VI
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in which X+ is a cationic dye and R5, R6, R7 and R8 independently of one another are each an alkyl, aryl, alkaryl, allyl, aralkyl, alkenyl or alkynyl group, an alicyclic group or a saturated or unsaturated heterocyclic group.
As is known, the photoinitiators are added in effective amounts, ie. In amounts of about 0.1 to about 10 % by weight, relative to the total amount of the mixture. If the mixtures according to the invention are used for stereolithographic processes in which laser radiation is normally employed, it is essential that the absorption capacity of the mixtures is so adjusted by means of the type and concentration of the photoinitiator that the depth of curing at normal laser speed is approximately 0.1 to 2.5 mm. The mixtures according to the invention can also contain different Photoinitiators which have a different radiation sensitivity in relation to the radiation of emission lines of different wavelengths. This achieves, for example, better utilization of a UV/VIS light source which radiates emission lines of different wavelengths. It is advantageous in this case if the various photoinitiators are so chosen and employed in such a concentration that a uniform optical absorption is produced in the case of the emission lines used (pages 7-8). Other photoinitiators are disclosed on pages 6-7. Useful urethane acrylates are disclosed on pages 5-6. Useful bisphenol diacrylates are disclosed on page 6. C-961: Aliphatic urethane diacrylate made by SARTOMER; MW = 1850, viscosity = 81 Pas at 60°C. SC-964: Aliphatic urethane diacrylate made by SARTOMER MW = 1300, viscosity = 21 Pas at 60°C. SC-965: Aliphatic urethane diacrylate made by SARTOMER; MW = 1500, viscosity =12 Pas at 60°C. SR-9504: Aliphatic urethane diacrylate made by SARTOMER; MW = 1700, viscosity =167 Pas at 21°C (page 17)
Hunziker et al. CA 2028541 does not exemplify a composition meeting the claims which contains a dye borate photoinitiator.
With respect to claims 16,17 and 19-20, it would have been obvious to one skilled in the art to modify the identified compositions of Hunziker et al. CA 2028541 by replacing at least a portion of the 1-hydroxycyclohexyl phenyl ketone with a dye-borate photoinitiator bounded by formula VI on page 7 with a reasonable expectation of forming a useful photosensitive composition based upon the disclosed equivalence at pages 6-7 and the use of mixtures on page 8. Further it would have been obvious to use the urethane monomer, bisphenol A and dye-borate photoinitiator in the amounts disclosed as useful in Hunziker et al. CA 2028541 with a reasonable expectation of forming a useful photosensitive composition.
Claims 16-17 and 19-20 are rejected under 35 U.S.C. 103 as being unpatentable over Hunziker et al. CA 2028541, in view of Adair et al. 4751102.
Adair et al. 4751102 teaches dye-borate photoinitiators where the useful dye cations can be cationic methine, polymethine, triarylmethane, indoline, thiazine, xanthene, oxazine and acridine dyes. More specifically, the dyes may be cationic cyanine, carbocyanine, hemicyanine, rhodamine and azomethine dyes. In addition to being cationic, the dyes should not contain groups which would neutralize or desensitize the complex or render the complex poorly dark stable. Examples of groups which generally should not be present in the dye are acid groups such as free carboxylic or sulphonic acid groups. Specific examples of useful cationic dyes are Methylene Blue, Safranine O, Malachite Green, cyanine dyes of the general formula (II) and rhodamine dyes of the formula (III) (col 3/line 46-col 12/line 9).
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Representative examples of alkyl groups represented by R.sup.1 -R.sup.4 are methyl, ethyl, propyl, butyl, pentyl, hexyl, octyl, stearyl, etc. The alkyl groups may be substituted, for example, by one or more halogen, cyano, acyloxy, acyl, alkoxy, or hydroxy groups Representative examples of aryl groups represented by R.sup.1 -R.sup.4 include phenyl, naphthyl, and substituted aryl groups such as anisyl. Alkaryl groups include methylphenyl, dimethylphenyl, etc. Representative examples of aralkyl groups represented by R.sup.1 -R.sup.4 groups include benzyl. Representative alicyclic groups include cyclobutyl, cyclopentyl, and cyclohexyl groups. Examples of an alkynyl group are propynyl and ethynyl, and examples of alkenyl groups include a vinyl group (col 5/lines 1-14)
It should be understood that the ionic dye-reactive counter ion compound selected will depend upon the colorant used. In other words, an ionic dye-reactive counter ion compound is selected which absorbs within a certain visible light wavelength region in which the particular colorant chosen preferably absorbs little, if any, visible light. Since the ionic dye compound absorbs at greater than 400 nm, it is colored, but the compound tends to be present in small amounts and it usually does not detract from the color of the colorant. There are applications, however, where the color of the ionic dye-reactive counter ion may be undesirable, for example, where the coating composition is white. In this case, it is desirable to select a photobleachable ionic dye compound. These ionic dye compounds are initially colored but are bleached upon exposure to radiation. (col. 14/lines 7-23)
With respect to claims 16-17 and 19-20, it would have been obvious to one skilled in the art to modify the identified compositions of Hunziker et al. CA 2028541 by replacing at least a portion of the 1-hydroxycyclohexyl phenyl ketone with a dye-borate photoinitiator bounded by formula VI on page 7 where R5 to R8 are alkyl groups such as butyl or hexyl based upon the disclosed equivalence at pages 6-7 and the specific disclosure of butyl and hexyl groups at col 5/lines 1-3 of Adair et al. 4751102, which is identified on page 7 of Hunziker et al. CA 2028541 where proper choice of the dye will allow the borate to bleach the dye and render the composition transparent/white/colorless as taught at (col. 14/lines 7-23) of Adair et al. 4751102. Further it would have been obvious to use the urethane monomer, bisphenol A and dye-borate photoinitiator in the amounts disclosed as useful in Hunziker et al. CA 2028541 with a reasonable expectation of forming a useful photosensitive composition.
Claims 16-20 are rejected under 35 U.S.C. 103 as being unpatentable over Konishi et al. WO 2017047547, in view of Sugita JP H10287450 or Sugita et al. JPH07228798
Konishi et al. WO 2017047547 in example 8 teaches a composition including a 50 wt% of a bisphenol A diacrylate, 30 wt% of an aliphatic urethane acrylate, 20 wt% of maphthoxyethyl acrylate and 3 parts of irgacure 184 (1-hydroxycyclohenylphenyl ketone) as the photoinitiator is exemplified in WO 2017047547 of example 8.
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[0149,0160-0164]. The desirability of high transparency is disclosed at [0049,0155].
Sugita JP H10287450 (machine translation attached) in inventive example 1, combines 100 g of pentaerythritol triacrylate, 0.1 g of a near-infrared light-absorbing cationic dye (Table 1, No. 3, n-butyltriphenylboron anion) and a boron-based catalyst ( Tetrabutylammonium / n-butyltriphenylboron) 0.5g of the photocurable composition 1 obtained by dissolving, a glass plate having a size of 30 cm × 30 cm was coated with an applicator to a thickness of 100 μm, and a glass plate of the same size was laminated thereon. By irradiating a halogen lamp with an output of 1500 W having a spectral distribution in a wavelength region of 400 to 1200 nm for 10 minutes, the blue color of the near-infrared light-absorbing dye is erased and the curable composition between the glasses is photo-cured, and colorless. A laminated glass having a transparent resin intermediate layer was obtained [0053].
(Comparative Example 1) 5 g of Irgacure 184 (manufactured by Ciba-Geigy), which is an ultraviolet light initiator, was changed to a combination of a cationic dye and a boron compound as a polymerization initiator. A functional glass was produced in the same manner as in Example 1 except for using. For light irradiation, a high-pressure mercury lamp having a spectral distribution in a wavelength region of 200 to 400 nm was used. By irradiation for 5 minutes, the curable composition between the glasses was photocured, but the red dye used as the colorant was decomposed and faded, and only unclear colored laminated glass was obtained [0061]. The composition can be a dye-borate and in formula 1
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[0014] or borate salt bounded by formula (2)
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where Wherein R .sub.1 , R .sub.2 , R .sub.3 and R .sub.4 are each independently an alkyl group, an aryl group, an allyl group, an aralkyl group, an alkenyl group, an alkynyl group, a silyl group, a heterocyclic group, a halogen atom, a substituted alkyl Group, substituted aryl group, substituted allyl group, substituted aralkyl group, substituted alkenyl group, substituted alkynyl group or substituted silyl group, and Z .sup.+ represents a cation [0014].
Sugita et al. JP-H07228798 (machine translation attached) in inventive examples 1 combines Pentaerythritol triacrylate-Hexamethylene diisocyanate-urethane prepolymer 70 g, nonaethylene glycol diacrylate After thoroughly mixing 30 g, a near infrared absorbing dye (Table 1 Complex No. 3, anion is n-butyltriphenylboron anion) 0.1 g Boron sensitizer tetrabutylammonium n-butyltriphenylboron 0.1 g, dye for coloring (azo chemical red dye manufactured by Orient Chemical Co., Ltd [0038].
Comparative Example 1 The same as Example 1 except that 3.0 g of an ultraviolet photopolymerization initiator (trade name Irgacure 184 manufactured by Ciba-Geigy) was used in place of the near infrared absorptive dye and the boron compound. Comparative sample 1 was prepared [0047]
(Comparative Example 2) The same as Example 3 except that 3.0 g of an ultraviolet photopolymerization initiator (trade name Irgacure 184 manufactured by Ciba-Geigy Co., Ltd.) was used instead of the near-infrared light absorbing dye and the boron compound. Comparative sample 2 was prepared [0048].
The color in the comparative examples changes the color relative to the dye for coloring in the cured film as evidenced in the DL, Da and Db values.
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Wherein Z .sup.+ is a quaternary ammonium cation, a quaternary pyridinium cation, a quaternary quinolinium cation, a phosphonium cation or a metal cation, and R .sub.1 , R .sub.2 , R .sub.3 and R .sub.4 are Independently alkyl group, aryl group, allyl group, aralkyl group, alkenyl group, alkynyl group, silyl group, heterocyclic group, halogen atom, substituted alkyl group, substituted aryl group, substituted allyl group, substituted aralkyl group, substituted alkenyl Group, substituted alkynyl group or substituted silyl group [0007-0008]
Konishi et al. WO 2017047547 does not exemplify a composition meeting the claims which contains a dye borate photoinitiator.
With respect to claims 16-20, it would have been obvious to one skilled in the art to modify example 8 of Konishi et al. WO 2017047547 by replacing at least a portion of the 1-hydroxycyclohexyl phenyl ketone with a dye and tetrabutylammonium borate photoinitiator taught by Sugita JP H10287450 or Sugita et al. JPH07228798 to increase the sensitivity and reduce the coloration in the cured product.
Claims 16-20 are rejected under 35 U.S.C. 103 as being unpatentable over Hunziker et al. CA 2028541, in view of Adair et al. 4751102, further in view of Sugita JP H10287450, Kishi JP H0860044 or Sugita et al. JPH07228798
The combination of Hunziker et al. CA 2028541 and Adair et al. 4751102 does not teach the borate recited in claims 18.
With respect to claims 16-20, it would have been obvious to one skilled in the art to modify the cited examples of Hunziker et al. CA 2028541 by replacing at least a portion of the 1-hydroxycyclohexyl phenyl ketone with a photoinitiators which are combination of a dye and a tetrabutylammonium borate taught by Sugita JP H10287450 or Sugita et al. JPH07228798 to increase the sensitivity and reduce the coloration in the cured product, noting the direction to dye borate combinations in Hunziker et al. CA 2028541 and Adair et al. 4751102, including the bleaching effect disclosed by Adair et al. 4751102. Further it would have been obvious to use the urethane monomer, bisphenol A and dye-borate photoinitiator in the amounts disclosed as useful in Hunziker et al. CA 2028541 with a reasonable expectation of forming a useful photosensitive composition.
Claims 16-20 are rejected under 35 U.S.C. 103 as being unpatentable over Hunziker et al. CA 2028541, in view of Adair et al. 4751102, further in view of Hagen et al. 20150353485.
Hagen et al. 20150353485 teaches that photoinitiators used are typically initiators which are activatable by actinic radiation and which trigger a polymerization of the corresponding polymerizable groups. Photoinitiators are commercially available compounds known per se, which are classed as unimolecular (type I) and bimolecular (type II). Type II photoinitiators may comprise in particular a cationic dye and a co-initiator. Useful co-initiators include ammonium arylborates as described for example in EP-A 0223587. Useful ammonium arylborates include, for example, tetrabutylammonium triphenylhexylborate, tetrabutylammonium triphenylbutylborate, tetrabutylammoniurn trinaphthylhexylborate, tetrabutylammonium tris(4-tert-butyl)phenylbutylborate, tetrabutylammonium tris(3-fluorophenyl)hexylborate, tetramethylammonium triphenylbenzylborate, tetra(n-hexyl)ammonium (sec-butyl)triphenylborate, 1-methyl-3-octylimidazolium dipentyldiphenylborate and tetrabutylammonium tris(3-chloro-4-methylphenyl)hexylborate (Cunningham et al., RadTech'98 North America UV/EB Conference Proceedings, Chicago, Apr. 19-22, 1998). Preferred photoinitiators are mixtures of tetrabutylammonium tetrahexylborate, tetrabutylammonium triphenylhexylborate, tetrabutylammonium tris(3-fluorophenyl)hexylborate ([191726-69-9], CGI 7460, product from BASF SE, Basle) and tetrabutylammonium tris(3-chloro-4-methylphenyl)hexylborate ([1147315-11-4], CGI 909, product from BASF SE, Basle) with the F+An- dyes of the present invention [0123-0125]. In one preferred embodiment of the method according to the present invert ion, the colored component of the liquid ink is a salt-type dye, more particularly selected from cationic dyes which preferably belong to the following classes: acridine dyes, xanthene dyes, thioxanthene dyes, phenazine dyes, phenoxazine dyes, phenothiazine dyes, coumarin dyes, tri(het)arylmethane dyes, in particular diamino-and triamino (het)arylmethane dyes, mono-, di-, tri-, tetra- and pentamethinecyanine dyes, hemicyanine dyes, diazahemicyanine dyes, zeromethine dyes, in particular naphthola.ctam dyes, streptocyanine dyes, externally cationic merocyanine dyes, externally cationic neutrocyanine dyes, externally cationic phthalocyanine dyes, externally cationic anthraquinone dyes, externally cationic azo dyes, or anionic dyes which preferably belong to the following classes: oxonols, di- and trihydroxytriarylmethane dyes, the group of merocyanine, neutrocyanine, coumarin, anthraquinone, anthrapyridone, dioxazine, mono-,dis- and trisazo dyes having at least one sulfo group, the group of acridine, xanthene, thioxanthene, phenazine, phenoxazine, phenothiazine, tri(het)arylinethane dyes, in particular diamino- and triamino(het)aryltriethane dyes, having at least two sulfo groups, phthalocyanines and azo metal complexes bearing at least one sulfo group, and also mixtures thereof [0071].
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With respect to claims 16-20, it would have been obvious to one skilled in the art to modify the cited examples of Hunziker et al. CA 2028541 by replacing at least a portion of the 1-hydroxycyclohexyl phenyl ketone with a photoinitiators which are combination of a dye and a tetrabutylammonium borate taught by Hagen et al. 20150353485noting the direction to dye borate combinations in Hunziker et al. CA 2028541 and Adair et al. 4751102, including the bleaching effect disclosed by Adair et al. 4751102. Further it would have been obvious to use the urethane monomer, bisphenol A and dye-borate photoinitiator in the amounts disclosed as useful in Hunziker et al. CA 2028541 with a reasonable expectation of forming a useful photosensitive composition.
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
20240150569, 20240142873, 20240317904 are related to the instant application, but have the same inventor.
20100112458 and 20070187947 teaches liquid holographic recording composition.
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MARTIN J. ANGEBRANNDT
Primary Examiner
Art Unit 1737
/MARTIN J ANGEBRANNDT/Primary Examiner, Art Unit 1737 June 29, 2026
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