IL227363A - Anhydride stock copolymers as soluble support material for fdm printer - Google Patents
Anhydride stock copolymers as soluble support material for fdm printerInfo
- Publication number
- IL227363A IL227363A IL227363A IL22736313A IL227363A IL 227363 A IL227363 A IL 227363A IL 227363 A IL227363 A IL 227363A IL 22736313 A IL22736313 A IL 22736313A IL 227363 A IL227363 A IL 227363A
- Authority
- IL
- Israel
- Prior art keywords
- weight
- support material
- maleic anhydride
- styrene
- copolymer
- Prior art date
Links
- 239000000463 material Substances 0.000 title claims description 69
- 229920001577 copolymer Polymers 0.000 title claims description 36
- 230000008021 deposition Effects 0.000 title description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 60
- 238000000034 method Methods 0.000 claims description 39
- 230000008569 process Effects 0.000 claims description 34
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 33
- 239000000178 monomer Substances 0.000 claims description 15
- 230000009477 glass transition Effects 0.000 claims description 13
- 238000010146 3D printing Methods 0.000 claims description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 7
- 239000002202 Polyethylene glycol Substances 0.000 claims description 7
- 229920001223 polyethylene glycol Polymers 0.000 claims description 7
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 19
- 238000007639 printing Methods 0.000 description 17
- 239000004609 Impact Modifier Substances 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- OWHSTLLOZWTNTQ-UHFFFAOYSA-N 2-ethylhexyl 2-sulfanylacetate Chemical compound CCCCC(CC)COC(=O)CS OWHSTLLOZWTNTQ-UHFFFAOYSA-N 0.000 description 10
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- 239000002245 particle Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- -1 poly(2-ethyl-2-oxazoline) Polymers 0.000 description 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- 239000011258 core-shell material Substances 0.000 description 6
- 229920001971 elastomer Polymers 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- 239000004014 plasticizer Substances 0.000 description 6
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 5
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 5
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000005060 rubber Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 238000012662 bulk polymerization Methods 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000011162 core material Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 238000000110 selective laser sintering Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- BWSZXUOMATYHHI-UHFFFAOYSA-N tert-butyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(C)(C)C BWSZXUOMATYHHI-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 239000006254 rheological additive Substances 0.000 description 2
- 229920001897 terpolymer Polymers 0.000 description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- HBJLPFLHWXZXCD-UHFFFAOYSA-N C1(C=C/C(=O)O1)=O.C(C)(C)(C)C1=C(C(=CC(=C1)C)C(C)(C)C)O Chemical compound C1(C=C/C(=O)O1)=O.C(C)(C)(C)C1=C(C(=CC(=C1)C)C(C)(C)C)O HBJLPFLHWXZXCD-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- 102100021202 Desmocollin-1 Human genes 0.000 description 1
- 239000004908 Emulsion polymer Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 101000968043 Homo sapiens Desmocollin-1 Proteins 0.000 description 1
- 101000880960 Homo sapiens Desmocollin-3 Proteins 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229920006187 aquazol Polymers 0.000 description 1
- 239000012861 aquazol Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 229920003247 engineering thermoplastic Polymers 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical class CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/04—Anhydrides, e.g. cyclic anhydrides
- C08F222/06—Maleic anhydride
- C08F222/08—Maleic anhydride with vinyl aromatic monomers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C41/00—Shaping by coating a mould, core or other substrate, i.e. by depositing material and stripping-off the shaped article; Apparatus therefor
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C67/00—Shaping techniques not covered by groups B29C39/00 - B29C65/00, B29C70/00 or B29C73/00
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/04—Anhydrides, e.g. cyclic anhydrides
- C08F222/06—Maleic anhydride
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L35/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C64/00—Additive manufacturing, i.e. manufacturing of three-dimensional [3D] objects by additive deposition, additive agglomeration or additive layering, e.g. by 3D printing, stereolithography or selective laser sintering
- B29C64/40—Structures for supporting 3D objects during manufacture and intended to be sacrificed after completion thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11163199A EP2514775A1 (en) | 2011-04-20 | 2011-04-20 | Maleic anhydride copolymers as soluble support material for fused deposition modelling (FDM) printer |
| PCT/EP2012/054306 WO2012143182A1 (en) | 2011-04-20 | 2012-03-13 | Maleic anhydride copolymers as soluble support material for fused deposition modelling (fdm) printer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL227363A0 IL227363A0 (en) | 2013-09-30 |
| IL227363A true IL227363A (en) | 2016-09-29 |
Family
ID=44560045
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL227363A IL227363A (en) | 2011-04-20 | 2013-07-07 | Anhydride stock copolymers as soluble support material for fdm printer |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8822590B2 (enExample) |
| EP (2) | EP2514775A1 (enExample) |
| JP (1) | JP5893128B2 (enExample) |
| KR (1) | KR20140009442A (enExample) |
| CN (1) | CN103380156B (enExample) |
| AU (1) | AU2012244499B2 (enExample) |
| BR (1) | BR112013023429B8 (enExample) |
| CA (1) | CA2833752C (enExample) |
| IL (1) | IL227363A (enExample) |
| RU (1) | RU2013151313A (enExample) |
| WO (1) | WO2012143182A1 (enExample) |
Families Citing this family (55)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9498593B2 (en) | 2013-06-17 | 2016-11-22 | MetaMason, Inc. | Customized medical devices and apparel |
| US9029058B2 (en) * | 2013-07-17 | 2015-05-12 | Stratasys, Inc. | Soluble support material for electrophotography-based additive manufacturing |
| US9745458B2 (en) | 2013-07-26 | 2017-08-29 | Hewlett-Packard Development Company, L.P. | Composite support material for three-dimensional printing |
| US10843401B2 (en) * | 2013-11-01 | 2020-11-24 | Kraton Polymers U.S. Llc | Fuse molded three dimensional article and a method for making the same |
| KR20160101998A (ko) * | 2013-12-18 | 2016-08-26 | 이네오스 스티롤루션 그룹 게엠베하 | 3-d 프린팅용의 비닐방향족/디엔 블록 공중합체에 기초한 몰딩 재료들의 용도 |
| US20160319120A1 (en) * | 2013-12-18 | 2016-11-03 | Ineos Styrolution Group Gmbh | Molding materials based on vinyl aromatic polymers for 3-d-printing |
| KR102215420B1 (ko) * | 2013-12-18 | 2021-02-15 | 이네오스 스티롤루션 그룹 게엠베하 | 3d 프린팅용의 비닐방향족 기반 몰딩 조성물 |
| CN105899591A (zh) | 2014-01-16 | 2016-08-24 | 陶氏环球技术有限责任公司 | 增材制造负载材料的回收 |
| JP6546179B2 (ja) * | 2014-01-16 | 2019-07-17 | ダウ グローバル テクノロジーズ エルエルシー | ３ｄ印刷用支持材料 |
| US9102099B1 (en) | 2014-02-05 | 2015-08-11 | MetaMason, Inc. | Methods for additive manufacturing processes incorporating active deposition |
| EP3107943B1 (en) * | 2014-02-19 | 2018-04-18 | Basf Se | Polymers as support material for use in fused filament fabrication |
| US9676159B2 (en) | 2014-05-09 | 2017-06-13 | Nike, Inc. | Method for forming three-dimensional structures with different material portions |
| WO2015195213A1 (en) * | 2014-06-16 | 2015-12-23 | Sabic Global Technologies B.V. | Process for additive manufacturing |
| CN104263150B (zh) * | 2014-09-10 | 2018-03-06 | 珠海天威飞马打印耗材有限公司 | 一种3d打印机及其工作台膜层的制备方法、涂覆在3d打印机工作台的涂料及其制备方法 |
| WO2016059987A1 (ja) * | 2014-10-14 | 2016-04-21 | 花王株式会社 | 三次元造形用可溶性材料 |
| JP6491467B2 (ja) * | 2014-10-14 | 2019-03-27 | 花王株式会社 | 三次元造形用可溶性材料 |
| JP5972335B2 (ja) | 2014-10-14 | 2016-08-17 | 花王株式会社 | 三次元造形用可溶性材料 |
| JP6568218B2 (ja) | 2014-12-23 | 2019-08-28 | ブリヂストン アメリカズ タイヤ オペレーションズ、 エルエルシー | 化学線硬化型高分子混合物、硬化高分子混合物、及び関連するプロセス |
| FR3030529B1 (fr) | 2014-12-23 | 2017-01-27 | Arkema France | Copolymere a blocs hydrosoluble et son utilisation comme materiau support pour impression 3d |
| WO2016205690A1 (en) | 2015-06-19 | 2016-12-22 | Stratasys, Inc. | Water dispersible polymer for use in additive manufacturing |
| EP3328930B1 (en) | 2015-07-27 | 2019-05-29 | Dow Global Technologies LLC | Method to additive manufacture biocompatible material and articles made by the method |
| WO2017020020A1 (en) * | 2015-07-30 | 2017-02-02 | Wildcat Dp Llc | Material and method for 3-d fabrication |
| WO2017048710A1 (en) | 2015-09-14 | 2017-03-23 | Carbon, Inc. | Light-curable article of manufacture with portions of differing solubility |
| US10647873B2 (en) | 2015-10-30 | 2020-05-12 | Carbon, Inc. | Dual cure article of manufacture with portions of differing solubility |
| KR102053481B1 (ko) * | 2015-11-03 | 2019-12-06 | 주식회사 엘지화학 | 3차원 조형물의 형성 방법 |
| US11049415B2 (en) | 2015-12-03 | 2021-06-29 | Dental Education Laboratories, Inc. | Anatomic apparatus and training system for remote and interactive hands-on surgical training |
| US11097531B2 (en) | 2015-12-17 | 2021-08-24 | Bridgestone Americas Tire Operations, Llc | Additive manufacturing cartridges and processes for producing cured polymeric products by additive manufacturing |
| CN108602048B (zh) | 2015-12-18 | 2022-02-18 | 坎特伯雷大学 | 分离介质 |
| US11045997B2 (en) * | 2015-12-24 | 2021-06-29 | Stratasys, Inc. | Water soluble support materials for high temperature additive manufacturing applications |
| US10953595B2 (en) | 2015-12-24 | 2021-03-23 | Stratasys, Inc. | Water soluble support materials for high temperature additive manufacturing applications |
| WO2017119218A1 (ja) * | 2016-01-05 | 2017-07-13 | コニカミノルタ株式会社 | 粉末材料、立体造形物の製造方法および立体造形装置 |
| US10449713B2 (en) | 2016-01-25 | 2019-10-22 | Te Connectivity Corporation | Article and method of forming an article |
| US20190143582A1 (en) | 2016-05-04 | 2019-05-16 | Covestro Deutschland Ag | Copolycarbonate as a supporting material in 3-d printing |
| CN109789632A (zh) | 2016-09-12 | 2019-05-21 | 沙特基础工业全球技术公司 | 用于增材制造工艺的牺牲高热支架材料 |
| EP3532267B1 (en) | 2016-10-27 | 2023-03-01 | Bridgestone Americas Tire Operations, LLC | Processes for producing cured polymeric products by additive manufacturing |
| JP6990594B2 (ja) * | 2017-02-07 | 2022-01-12 | 株式会社日本触媒 | 水性樹脂組成物 |
| CN110730800B (zh) | 2017-05-26 | 2022-08-19 | 无限材料解决方案有限公司 | 水性聚合物组合物 |
| WO2018227094A1 (en) | 2017-06-08 | 2018-12-13 | Buchanan Stephen L | Tooth or tooth replica holding sleeve for use with an paex locator |
| JP2019064258A (ja) * | 2017-09-28 | 2019-04-25 | 花王株式会社 | 三次元造形用可溶性材料 |
| WO2019065824A1 (ja) * | 2017-09-28 | 2019-04-04 | 花王株式会社 | 三次元造形用可溶性材料 |
| EP3694939A1 (en) | 2017-10-10 | 2020-08-19 | Stratasys, Inc. | Water-dispersible thermoplastic material comprising sulfonated copolymer for use in additive manufacturing |
| FR3074181B1 (fr) | 2017-11-28 | 2020-11-06 | Arkema France | Composition copolymerique hydrosoluble a ph neutre |
| CN111670105B (zh) * | 2018-02-02 | 2022-06-07 | 三菱化学株式会社 | 三维造型用材料、三维造型用细丝、该细丝的卷绕体和三维打印机用盒 |
| EP3755785A1 (en) | 2018-02-22 | 2020-12-30 | The Procter & Gamble Company | Methods for making unit dose articles |
| WO2020077127A1 (en) * | 2018-10-10 | 2020-04-16 | Stratasys, Inc. | Water dispersible sulfonated thermoplastic copolymer for use in additive manufacturing |
| FR3088327B1 (fr) | 2018-11-08 | 2021-11-05 | Arkema France | Composition copolymerique hydrosoluble |
| US20210178661A1 (en) * | 2019-12-17 | 2021-06-17 | Ticona Llc | Three-Dimensional Printing System Employing A Toughened Polyarylene Sulfide Composition |
| EP3865302B1 (en) * | 2020-02-14 | 2024-08-14 | iSQUARED AG | Copolymer for use in a digital manufacturing process |
| US12371581B2 (en) | 2020-03-25 | 2025-07-29 | Infinite Material Solutions, Llc | High performance water soluble polymer compositions |
| US20230271379A1 (en) * | 2020-08-06 | 2023-08-31 | Signify Holding B.V. | Continuous hollow tube printing using fdm |
| US12157800B2 (en) | 2021-04-12 | 2024-12-03 | Stratasys, Inc. | Method for underwater processing of water-dispersible materials |
| KR20240123438A (ko) | 2021-04-19 | 2024-08-13 | 자빌 인코퍼레이티드 | 개선된 적층 제조 분리 지지 재료 |
| FR3124420B1 (fr) * | 2021-06-23 | 2024-09-27 | Arkema France | Utilisation de copolymères multi blocs en tant que matériau sacrificiel dans un procédé d’impression 3D |
| WO2024076464A1 (en) | 2022-10-03 | 2024-04-11 | Jabil Inc. | Additive manufactured article comprising a grafted aliphatic polyketone, filament and powder |
| NL2036419B1 (en) | 2023-12-04 | 2025-06-13 | Tectonic 3D Swip B V | Fused deposition modeling method and method to dissolve a high temperature polycarbonate support used in this method |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU463914B2 (en) | 1971-09-22 | 1975-08-07 | Dow Chemical Company, The | Impact resistant polymers ofa resinous copolymer ofan alkenyl aromatic. monomer and unsaturated dicarboxylic anhydride |
| DE3034171A1 (de) * | 1980-09-11 | 1982-05-06 | Basf Ag, 6700 Ludwigshafen | Alkaliloesliche harze auf basis von copolymerisaten aus monoolefinisch ungesaettigten carbonsaeuren und durch aromaten substituierten (alpha) -olefinen und ihre verwendung als harzkomponente in polymerdispersionen |
| JPH0260909A (ja) * | 1988-08-26 | 1990-03-01 | Nippon Oil & Fats Co Ltd | 熱硬化型水溶性樹脂及びその硬化物 |
| US5121329A (en) | 1989-10-30 | 1992-06-09 | Stratasys, Inc. | Apparatus and method for creating three-dimensional objects |
| JPH075302A (ja) * | 1993-06-15 | 1995-01-10 | Tosoh Corp | マイクロ集光レンズ形成用感光性組成物 |
| US5503785A (en) | 1994-06-02 | 1996-04-02 | Stratasys, Inc. | Process of support removal for fused deposition modeling |
| US6228923B1 (en) * | 1997-04-02 | 2001-05-08 | Stratasys, Inc. | Water soluble rapid prototyping support and mold material |
| US6070107A (en) * | 1997-04-02 | 2000-05-30 | Stratasys, Inc. | Water soluble rapid prototyping support and mold material |
| US7754807B2 (en) | 1999-04-20 | 2010-07-13 | Stratasys, Inc. | Soluble material and process for three-dimensional modeling |
| HK1043087B (zh) | 1999-04-20 | 2007-12-28 | 斯特拉塔西斯公司 | 可溶材料和三维模型的加工方法 |
| JP4148733B2 (ja) * | 2002-09-02 | 2008-09-10 | リコープリンティングシステムズ株式会社 | 三次元積層造形法とその装置 |
| EP1648945A4 (en) | 2003-07-24 | 2008-06-25 | Nova Chem Inc | STYRENE RESIN COMPOSITION AND ARTICLES PRODUCED THEREFROM |
| JP2006111710A (ja) * | 2004-10-14 | 2006-04-27 | Nof Corp | 無水マレイン酸（共）重合体の製造方法、無水マレイン酸（共）重合体、及びその加水分解物 |
| CN100387419C (zh) * | 2006-01-16 | 2008-05-14 | 南京师范大学 | 采用逐层喷涂方式制作三维物体的方法 |
| CN100340388C (zh) * | 2006-03-03 | 2007-10-03 | 南京师范大学 | 制作三维物体和支撑的打印成型方法 |
| US8246888B2 (en) | 2008-10-17 | 2012-08-21 | Stratasys, Inc. | Support material for digital manufacturing systems |
-
2011
- 2011-04-20 EP EP11163199A patent/EP2514775A1/en not_active Withdrawn
-
2012
- 2012-03-13 EP EP12708835.9A patent/EP2699611B1/en active Active
- 2012-03-13 RU RU2013151313/04A patent/RU2013151313A/ru not_active Application Discontinuation
- 2012-03-13 US US13/982,431 patent/US8822590B2/en active Active
- 2012-03-13 CA CA2833752A patent/CA2833752C/en active Active
- 2012-03-13 WO PCT/EP2012/054306 patent/WO2012143182A1/en not_active Ceased
- 2012-03-13 BR BR112013023429A patent/BR112013023429B8/pt not_active IP Right Cessation
- 2012-03-13 AU AU2012244499A patent/AU2012244499B2/en not_active Ceased
- 2012-03-13 CN CN201280009711.4A patent/CN103380156B/zh not_active Expired - Fee Related
- 2012-03-13 JP JP2014505552A patent/JP5893128B2/ja not_active Expired - Fee Related
- 2012-03-13 KR KR1020137026041A patent/KR20140009442A/ko not_active Withdrawn
-
2013
- 2013-07-07 IL IL227363A patent/IL227363A/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| US20130317164A1 (en) | 2013-11-28 |
| AU2012244499B2 (en) | 2015-05-21 |
| US8822590B2 (en) | 2014-09-02 |
| EP2699611A1 (en) | 2014-02-26 |
| CA2833752A1 (en) | 2012-10-26 |
| EP2514775A1 (en) | 2012-10-24 |
| RU2013151313A (ru) | 2015-05-27 |
| BR112013023429A2 (pt) | 2016-12-13 |
| CA2833752C (en) | 2019-05-14 |
| AU2012244499A1 (en) | 2013-07-25 |
| WO2012143182A1 (en) | 2012-10-26 |
| BR112013023429B8 (pt) | 2022-07-05 |
| KR20140009442A (ko) | 2014-01-22 |
| JP2014511933A (ja) | 2014-05-19 |
| BR112013023429B1 (pt) | 2020-11-17 |
| CN103380156B (zh) | 2016-01-20 |
| CN103380156A (zh) | 2013-10-30 |
| JP5893128B2 (ja) | 2016-03-23 |
| EP2699611B1 (en) | 2015-05-06 |
| IL227363A0 (en) | 2013-09-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2012244499B2 (en) | Maleic anhydride copolymers as soluble support material for fused deposition modelling (fdm) printer | |
| JP6016913B2 (ja) | 立体物体を製造するためのポリマー粉末 | |
| JP6657106B2 (ja) | 熱溶解フィラメント製法において使用するための支持体材料としてのポリマー | |
| TW201229066A (en) | Water-soluble or water-disintegrable copolymer | |
| WO2008090906A1 (ja) | （メタ）アクリル系重合体粒子、その製造方法、（メタ）アクリル系重合体粒子を用いたプラスチゾル組成物及びこれを用いた物品 | |
| WO2014098141A1 (ja) | ポリマー及びその製造方法、成形材料並びに成形体 | |
| CN109689710A (zh) | 通过使用甲基丙烯酰胺改进pmma泡沫的性能 | |
| JP7553545B2 (ja) | 機械的特性が改善されたｐｍｍａ系のキャストポリマー | |
| WO2001088021A1 (fr) | Procede de production de polymere acrylique | |
| JP2007504289A (ja) | ポリメタクリルイミドを製造するためのコポリマーの合成方法 | |
| CN106459314B (zh) | 聚合物粉末组合物和其制备方法 | |
| US12134213B2 (en) | Process for forming a rotational molded article | |
| US8022135B2 (en) | Embedment casting composition | |
| JP4665343B2 (ja) | 樹脂組成物、成形体及び成形体の製造方法 | |
| JP4857728B2 (ja) | 無機物粒子含有メタクリル樹脂の製法 | |
| CN108473610A (zh) | 树脂组合物、成型体和成型体的制造方法 | |
| JP2013056956A (ja) | 熱可塑性樹脂組成物 | |
| JP2008063369A (ja) | アクリル系重合体微粒子、その製法及びプラスチゾル組成物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed |