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WO1999055766B1 - Novel polymer additives for forming objects - Google Patents

Novel polymer additives for forming objects

Info

Publication number
WO1999055766B1
WO1999055766B1 PCT/US1999/009327 US9909327W WO9955766B1 WO 1999055766 B1 WO1999055766 B1 WO 1999055766B1 US 9909327 W US9909327 W US 9909327W WO 9955766 B1 WO9955766 B1 WO 9955766B1
Authority
WO
WIPO (PCT)
Prior art keywords
prepolymer composition
polyester resin
polymer
ethylene glycol
prepolymer
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US1999/009327
Other languages
French (fr)
Other versions
WO1999055766A1 (en
Inventor
Mohammad W Katoot
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US09/069,558 external-priority patent/US6146556A/en
Application filed by Individual filed Critical Individual
Priority to EP99917670A priority Critical patent/EP1080128A1/en
Priority to AU35737/99A priority patent/AU3573799A/en
Priority to CA002333228A priority patent/CA2333228A1/en
Publication of WO1999055766A1 publication Critical patent/WO1999055766A1/en
Publication of WO1999055766B1 publication Critical patent/WO1999055766B1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/68—Unsaturated polyesters
    • C08G18/683—Unsaturated polyesters containing cyclic groups
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B26/00—Compositions of mortars, concrete or artificial stone, containing only organic binders, e.g. polymer or resin concrete
    • C04B26/02—Macromolecular compounds
    • C04B26/10—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C04B26/16—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/36—Hydroxylated esters of higher fatty acids
    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/14—Peroxides
    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B2111/00—Mortars, concrete or artificial stone or mixtures to prepare them, characterised by specific function, property or use
    • C04B2111/20—Resistance against chemical, physical or biological attack
    • C04B2111/28—Fire resistance, i.e. materials resistant to accidental fires or high temperatures

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Ceramic Engineering (AREA)
  • Materials Engineering (AREA)
  • Structural Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

The present invention relates to novel methods and compositions related to polymer concrete comprising conventional resins with novel additives to prevent shrinking and cracking of the resin, to accelerate curing and to treat fillers. These compositions and methods can be employed to form large objects and objects of irregular shapes. These compositions and methods provide lightweight materials some of which are hard and inflexible, while others are hard and flexible.

Claims

96 AMENDED CLAIMS [received by the International Bureau on 1 November 1999 (01.11.99); original claims 1-51 replaced by new claims 1-78 (10 pages)]
1. A composition comprising: at least one oil; dibutyltin dilaurate; at least one molecular sieve; at least one filler maternal: and at least one surfactant selected from ANTAROX 25-R2 and RHOD AFAC RS-710.
2. The composition of Claim 1, wherein the at least one oil comprises castor oil, linseed oil, or a combination thereof.
3. The composition of Claim 1, wherein the at least one filler material comprises calcium carbonate, sand, or a combination thereof.
4. The composition of Claim 1, further comprising diphenylmethane diisocyanate.
5. The composition of Claim 1, wherein the surfactant compnses ANTAROX 25-R2.
6. The composition of Claim 1, further comprising propylene glycol, fumaric acid, maleic anhydride, and phthalic anhydride.
7. A polyurethane polymer produced from the composition of any one of Claims 1-6.
8. The polyurethane polymer of Claim 7, wherein the composition comprises castor oil, linseed oil, ANTAROX 25-R2, calcium carbonate, sand, and 4,4 '-diphenylmethane diisocyanate.
9. The polyurethane polymer of Claim 8, further compnsing propylene glycol, fumaric acid, maleic anhydride, and phthalic anhydride. 97
10. The polyurethane polymer of Claim 7, wherein the composition comprises castor oil, linseed oil, RHODAFAC RS-710, calcium carbonate, sand, and 4,4'-diphenylmethane diisocyanate.
11. A prepolymer composition comprising a solution that is capable of undergoing polymerization and is substantially non-flammable.
12. The prepolymer composition of Claim 11, wherein the prepolymer composition has a flash point of greater than approximately 150°F.
13. The prepolymer composition of Claim 11, wherein the prepolymer composition has a flash point of greater than approximately 190°F.
14. The prepolymer composition of Claim 11, wherein the prepolymer composition has a flash point of greater than approximately 212°F.
15. The prepolymer composition of Claim 11, wherein the prepolymer solution is polymerized to form a solid object.
16. The prepolymer composition of Claim 11, wherein the composition comprises: polyethylene glycol; and polyester resin.
17. The prepolymer composition of Claim 16, further comprising: ethylene glycol; and maleic anhydride.
18. The prepolymer composition of Claim 17, further comprising: polystyrene; and ethylenediamine.
19. The prepolymer composition of Claim 17, further comprising styrene. 98
20. The prepolymer composition of Claim 19, further comprising ethylenediamine.
21. The prepolymer composition of Claim 16, further comprising ethylene dimethacrylate.
22. The prepolymer composition of Claim 16 or 17, further comprising at least one of ethylene dimethacrylate (EDM), polyvinyl alcohol, an epoxy resin, borax, carboxymethyl cellulose (CMC), ethylene glycol dimethacrylate (EGD), polyethylene glycol dimethacrylate (PEGDAM), ethylene glycol, diethylene glycol (DEG), fumaric acid, pentaerythritol tetraacrylate (PENT A), and a peroxide.
23. The prepolymer composition of Claim 16, further comprising:
N,N-dimethyI aniline; a catalyst; and at least one peroxide.
24. The prepolymer composition of Claim 23, wherein the catalyst comprises cobalt naphthenate.
25. The prepolymer composition of Claim 23, wherein the at least one peroxide comprises methyl ethyl ketone peroxide, hydrogen peroxide, benzoyl peroxide or a combination thereof.
26. The prepolymer composition of any one of Claims 11-25, further comprising at least one filler material.
27. The prepolymer composition of Claim 26, wherein the at least one filler material comprises calcium carbonate, calcium oxide, gypsum, or a combination thereof.
28. A polymer produced from the prepolymer composition of any one of Claims 11 -27. 99
29. The polymer of Claim 28, wherein the prepolymer composition comprises ethylene glycol; maleic anhydride; polyethylene glycol; polyester resin powder; polystyrene; ethylenediamine; calcium carbonate; N,N-dimethyl aniline; cobalt naphthenate; methyl ethyl ketone peroxide; and hydrogen peroxide.
30. The polymer of Claim 28, wherein the prepolymer composition comprises ethylene glycol; maleic anhydride; polyethylene glycol; polyester resin powder; styrene; ethylenediamine; calcium carbonate; N,N-dimethyl aniline; cobalt naphthenate; methyl ethyl ketone peroxide; and hydrogen peroxide.
1. The polymer of Claim 28, wherein the prepolymer composition comprises polyethylene glycol; polyester resin powder; and ethylene dimethacrylate (EDM).
32. The polymer of Claim 31, wherein the prepolymer composition further comprises ethylene glycol and maleic anhydride.
33. The polymer of Claim 31 or 32, wherein the prepolymer composition further comprises calcium carbonate; N,N-dimethyl aniline; cobalt naphthenate; methyl ethyl ketone peroxide; and hydrogen peroxide.
34. The polymer of Claim 31 or 32, wherein the prepolymer composition further comprises calcium carbonate; N,N-dimethyl aniline; benzoyl peroxide; and gypsum.
35. The polymer of Claim 32, wherein the prepolymer composition further comprises poly vinyl alcohol and at least one of N,N-dimethyl aniline and borax.
36. The polymer of Claim 28, wherein the prepolymer composition further comprises ethylene glycol; maleic anhydride; polyethylene glycol; polyester resin powder; polyvinyl alcohol; and carboxymethyl cellulose. 100
37. The polymer of Claim 28, wherein the prepolymer composition further comprises ethylene glycol; maleic anhydride; polyethylene glycol; polyester resin powder; and polyethylene glycol dimethylmethacrylate (PEGDAM).
38. The polymer of Claim 37, wherein the prepolymer composition further comprises calcium carbonate; N,N-dimethyl aniline; cobalt naphthenate; methyl ethyl ketone peroxide; hydrogen peroxide; and at least one of ethylene glycol dimethacrylate (EGD) and pentaerythritol tetraacrylate (PENTA).
39. The polymer of Claim 28, wherein the prepolymer composition further comprises ethylene glycol; maleic anhydride; polyethylene glycol; polyester resin powder; and diethylene glycol.
40. The polymer of Claim 39, wherein the prepolymer composition further comprises calcium carbonate; N,N-dimethyl aniline; cobalt naphthenate; methyl ethyl ketone peroxide; hydrogen peroxide; and at least one of ethylene glycol dimethacrylate (EGD) and pentaerythritol tetraacrylate (PENTA).
41. The polymer of Claim 28, wherein the prepolymer composition further comprises polyethylene glycol; maleic anhydride; polyethylene glycol; polyester resin powder; and polyethylene glycol dimethylmethacrylate (PEGDAM).
42. The polymer of Claim 41, wherein the prepolymer composition further comprises calcium carbonate; N,N-dimethyl aniline; cobalt naphthenate; methyl ethyl ketone peroxide; hydrogen peroxide; and at least one of ethylene glycol dimethacrylate (EGD) and pentaerythritol tetraacrylate (PENTA).
43. A prepolymer composition comprising: at least one glycol selected from ethylene glycol and propylene glycol; fumaric acid; and an epoxy resin or at least one anhydride selected from maleic anhydride and phthalic anhydride. 101
44. The prepolymer composition of Claim 43, further comprising at least one of styrene and 2-hydroxymethylmethacrylate (HEMA).
45. The prepolymer composition of Claim 43 or 44, further comprising at least one of: polyethylene glycol; polyethylene glycol dimethylmethacrylate (PEGDAM); ethylene glycol dimethacrylate (EGD); pentaerythritol tetraacrylate (PENTA); tetra(ethylene glycol); tetra(ethylene glycol) dimethylacrylace; 4,4'-diaminodiphenyl methane; a polyester resin; carboxymethyl cellulose (CMC); polymethyl methacrylate; methyl methacrylate; ethylene glycol; diethylene glycol; diallyl phthalate; a surfactant; and a filler material.
46. The prepolymer composition of Claim 45, further comprising at least one of cobalt naphthenate, 1-vinyl 2-pyrrolidinone, N',N-dimethyl aniline, aluminum trihydride, and a peroxide.
47. The prepolymer composition of Claim 46, further comprising at least one of (a) acrylic acid, or (b) methacrylic acid.
48. The prepolymer composition of Claim 47, further comprising ethyl acrylate.
49. The prepolymer composition of Claim 48, further comprising: polyaniline; polyvinylalcohol; sulfuric acid; ethylene glycol; and CUCIO .
50. The prepolymer composition of Claim 49, further comprising tetra(ethyleneglycol) dimethylacrylate, tetra(ethy)eneglycol) or pentaerythritol tetraacrylate. 102
51. The prepolymer composition of Claim 47, further comprising: bisphenol A; benzyldimethyltetradecylammonium chloride dihydrate; and monohydroxyhydroquinon.
52. The prepolymer composition of Claim 47, further comprising carboxymethyl cellulose.
53. The prepolymer composition of Claim 47, further comprising at least one of 4,4-diphenylmethane diisocyanate and N, N-dimethylaniline.
54. A high flash point polyester resin produced from the prepolymer composition of any one of Claims 43-53.
55. The high flash point polyester resin of Claim 54, wherein the prepolymer composition comprises ethylene glycol, fumaric acid, maleic anhydride, and polyethylene glycol dimethylmethacrylate (PEGDAM).
56. The polymer of Claim 55, wherein the prepolymer composition further comprises calcium carbonate; N,N-dimethyl aniline; cobalt naphthenate; methyl ethyl ketone peroxide; hydrogen peroxide; and at least one of ethylene glycol dimethacrylate (EGD) and pentaerythritol tetraacrylate (PENTA).
57. The polymer of Claim 55, wherein the prepolymer composition further comprises N,N-dimethyl aniline; cobalt naphthenate; methyl ethyl ketone peroxide; hydrogen peroxide; at least one of ethylene glycol dimethacrylate (EGD) and pentaerythritol tetraacrylate (PENTA); and at least one of calcium oxide and calcium carbonate.
58. The high flash point polyester resin of Claim 54, wherein the prepolymer composition comprises ethylene glycol, fumaric acid, ethylene glycol dimethacrylate (EGD), and pentaerythritol tetraacrylate (PENTA).
59. The polymer of Claim 58, wherein the prepolymer composition further comprises at least one of an epoxy resin; polyethylene glycol; carboxymethyl cellulose; polymethyl methacrylate; methyl methacrylate; calcium carbonate; N,N-dimethyl aniline; cobalt naphthenate; methyl ethyl ketone peroxide; and hydrogen peroxide.
60. The polymer of Claim 58, wherein the prepolymer composition further comprises at least one of polyethylene glycol dimethylmethacrylate (PEGDAM); 4,4'-diaminodiphenyl methane; benzoyl peroxide; polyethylene glycol; and tetraethylene glycol (TEG).
61. The high flash point polyester resin of Claim 54, wherein the prepolymer composition comprises propylene glycol, fumaric acid, maleic anhydride, phthalic anhydride, and at least one of styrene and 2- hydroxyethylmethacrylate (HEMA).
62. The high flash point polyester resin of Claim 61, wherein the prepolymer composition further comprises 4,4'-diaminodiρhenyl methane; benzoyl peroxide; polyethylene glycol; and at least one of ethylene glycol dimethacrylate (EGD); diallyl phthalate; and diethylene glycol.
63. The high flash point polyester resin of Claim 62, wherein the prepolymer composition further comprises at least one of ethylene glycol; polyethylene glycol dimethylmethacrylate (PEGDAM); pentaerythritol tetraacrylate (PENTA); and dodecylbenzenesulfonic acid.
64. The high flash point polyester resin of Claim 61, wherein the prepolymer composition further comprises diallyl phthalate and polyethylene glycol
65. The high flash point polyester resin of Claim 61, wherein the prepolymer composition further comprises polyethylene glycol dimethylmethacrylate (PEGDAM); tetra(ethylene glycol) dimethyl aery late; 4,4'- diaminodiphenyl methane; and benzoyl peroxide. 104
66. The high flash point polyester resin of Claim 61, wherein the prepolymer composition further comprises 1-vinyl 2-pyrrolidinone; ethyl acrylate; and at least one of acrylic acid and methacrylic acid.
67. The high flash point polyester resin of Claim 66, wherein the prepolymer composition further comprises tetra(efhylene glycol) dimethylacrylate or teιra(ethylene glycol) diacrylate; N,N-dimethyl aniline; cobalt naphthenate; methyl ethyl ketone peroxide; and hydrogen peroxide.
68. The high flash point polyester resin of Claim 66, wherein the prepolymer composition further comprises pentaerythritol tetraacrylate (PENTA); N,N-dimethyl aniline; cobalt naphthenate; methyl ethyl ketone peroxide; and hydrogen peroxide.
69. The high flash point polyester resin of Claim 68, wherein the prepolymer composition further comprises polyaniline; N-methyl-pyrrolidinone; polyviπylalcohol; sulfuric acid; ethylene glycol; and CuC104.
70. The high flash point polyester resin of Claim 61, wherein the prepolymer composition further comprises bisphenol A; benzyldimemyltetradecylarnmonium chloride dihydrate; monohydroxyhydroquinon; N,N-dimethyl aniline; cobalt naphthenate; methyl ethyl ketone peroxide; and hydrogen peroxide.
71. The high flash point polyester resin of Claim 66, wherein the prepolymer composition further comprises carboxymethyl cellulose; N,N- dimethyl aniline; cobalt naphthenate; methyl ethyl ketone peroxide; and hydrogen peroxide.
72. The high flash point polyester resin of Claim 66, wherein the prepolymer composition further comprises 4,4'-diphenylmethane diisocyanate; N,N-dimethyl aniline; cobalt naphthenate; methyl ethyl ketone peroxide; and hydrogen peroxide. 105
73. A fast cure polyester/concrete mixture comprising a polyester resin; Sakrete concrete mix; styrene; N,N-dimethyl aniline; and cobalt naphthenate.
74. The polyester/concrete mixture of Claim 73, further comprising methyl methacrylate; and at least one of methyl ethyl ketone peroxide, hydrogen peroxide, and benzoyl peroxide.
75. The polyester/concrete mixture of Claim 74, further comprising propylene glycol, fumaric acid, maleic anhydride, phthalic anhydride, chopped fiberglass fibers; and 2-hydroxyethylmethacrylate (HEMA).
76. The polyester/concrete mixture of Claim 73, further comprising methyl ethyl ketone peroxide, hydrogen peroxide, and benzoyl peroxide.
77. The polyester/concrete mixture of Claim 76, further comprising propylene glycol, fumaric acid, maleic anhydride, phthalic anhydride, chopped fiberglass fibers; and 2-hydroxyethylmethacrylate (HEMA).
78. The polyester/concrete mixture of Claim 73, wherein the polyester resin comprises the polymer of Claim 28 or 54.
106
STATEMENT UNDER ARTICLE 19
The amendments to claims 1, 4-6, 8-10, 12, 18, 21-25 and 32, and new claims 7-10, 26-42, and 54-78 more particularly set forth the inventive aspect of the prepolymer compositions, polymers formed the prepolymer compositions, and polymer/concrete mixtures. More specifically, the above amendments (1) specify components of the prepolymer compositions, (2) specify components of the polymers formed from the prepolymer compositions, (3) specify components of the polymer/concrete mixtures, (4) correct misspelled words in the claims, and (5) correct errors in the original claims. The most obvious error, which has now been corrected, is the change of "°C" to "T" for the flash point temperature of the prepolymer composition of claims 12-14.
The amendments to claims 1, 4-6, 8-10, 12, 18, 21-25 and 32 are supported throughout the specification and the original claims. In particular, the amendments to claims 1 , 4-6, 8-10, 12, 18, 21-25 and 32 are supported in Examples 33-124 and original claims 1-51.
New claims 7-10, 26-42, and 54-78 are supported throughout the specification. In particular, the new claims 7-10, 26-42, and 54-78 are supported in Examples 33-133.
PCT/US1999/009327 1998-04-29 1999-04-29 Novel polymer additives for forming objects Ceased WO1999055766A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP99917670A EP1080128A1 (en) 1998-04-29 1999-04-29 Novel polymer additives for forming objects
AU35737/99A AU3573799A (en) 1998-04-29 1999-04-29 Novel polymer additives for forming objects
CA002333228A CA2333228A1 (en) 1998-04-29 1999-04-29 Novel polymer additives for forming objects

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US09/069,558 US6146556A (en) 1998-04-29 1998-04-29 Polymer additives for forming objects
US09/069,558 1998-04-29
US20961598A 1998-12-11 1998-12-11
US09/209,615 1998-12-11
US12253699P 1999-03-02 1999-03-02
US60/122,536 1999-03-02

Publications (2)

Publication Number Publication Date
WO1999055766A1 WO1999055766A1 (en) 1999-11-04
WO1999055766B1 true WO1999055766B1 (en) 1999-12-09

Family

ID=27371565

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1999/009327 Ceased WO1999055766A1 (en) 1998-04-29 1999-04-29 Novel polymer additives for forming objects

Country Status (4)

Country Link
EP (1) EP1080128A1 (en)
AU (1) AU3573799A (en)
CA (1) CA2333228A1 (en)
WO (1) WO1999055766A1 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8814861B2 (en) 2005-05-12 2014-08-26 Innovatech, Llc Electrosurgical electrode and method of manufacturing same
CN107075193B (en) 2014-09-24 2020-10-02 科慕埃弗西有限公司 Materials with enhanced protection of photosensitive entities
CN109851746A (en) * 2018-12-24 2019-06-07 山东一诺威聚氨酯股份有限公司 Cellulose modified TPU film material and preparation method thereof
CN110433742B (en) * 2019-09-11 2022-03-01 成都工业学院 Preparation method of microcapsule with double-layer coating structure and microcapsule prepared by preparation method

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3884980A (en) * 1970-04-06 1975-05-20 Cincinnati Milacron Chem Aldol condensation using cobalt II halide hydrazine complexes
US3895149A (en) * 1973-07-05 1975-07-15 Atlantic Richfield Co Carpet backed with thixotropic polyurethane adhesive
CA1029494A (en) * 1973-07-27 1978-04-11 Fritz Ehrhard Shaped polyurethane articles and a method for making them
US4013614A (en) * 1975-01-29 1977-03-22 H. H. Robertson Company Method of preparing shaped articles from polymerizable compositions
JPS6138662A (en) * 1984-07-30 1986-02-24 Toyoda Gosei Co Ltd Process for curing urethane coating film
US4691045A (en) * 1984-12-06 1987-09-01 Nippon Shokubai Kagaku Co., Ltd. Hydroxyl group-containing (meth)acrylate oligomer, prepolymer therefrom, and method for use thereof
US4822849A (en) * 1987-08-03 1989-04-18 Reichhold Chemicals, Inc. Low shrink hybrid resins
US5284705A (en) * 1990-09-06 1994-02-08 Garland Floor Co. Antistatic coating comprising tin-oxide-rich pigments and process and coated substrate

Also Published As

Publication number Publication date
AU3573799A (en) 1999-11-16
WO1999055766A1 (en) 1999-11-04
EP1080128A1 (en) 2001-03-07
CA2333228A1 (en) 1999-11-04

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