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US4016115A Expired / Lapsed US ⏱️ 0.0 years remaining

Unsaturated polyester resin composition containing titanium dioxide

Assignee: Toyobo Co Ltd
•
Filing: 1975-09-26
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Granted: 1977-04-05
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Expires: 1995-09-26
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Abstract

Abstract An unsaturated polyester resin composition containing titanium dioxide excellent in the stability of dispersion of the titanium dioxide and suitable for the manufacture of opaque, molded products comprising (1) an unsaturated polyester resin containing titanium dioxide consisting of an unsaturated polyester obtained from a high molecular weight saturated polyester containing titanium dioxide as the raw material and a copolymerizable monomer and (2) at least one compound selected from the group consisting of a hydroxyalkylamine (A) having at least one amino group and at least one hydroxyl group attached to different carbon atoms thereof, a polyoxyalkyleneamine (B), a mono- or dicarboxylate (C) derived from the compound (A) and a mono- or dicarboxylate (D) derived from the compound (B).

Inventors

  • 👤 Hideo Miyake
  • 👤 Toshio Tsuchida

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-25 09:35
CPC Classifications
C; C08; C08K; C08K3/00; C08K3/18; C08K3/20; C08K3/22; C08K5/00; C08K5/16; C08K5/17; C08L; C08L67/00; C08L67/06

Claims Analysis

Total Claims: 30
Claim 1
Independent Claim 94 words
An unsaturated polyester resin composition containing titanium dioxide comprising: 1. an unsaturated polyester resin containing titanium dioxide consisting of i. an unsaturated polyester containing titanium dioxide obtained from a. a depolycondensation product produced by depolycondensing a high molecular weight saturated polyester containing titanium dioxide by using one or more compounds selected from the group consisting of glycols, saturated dibasic acids or anhydrides thereof, unsaturated dibasic acids or anhydrides thereof, and esters or oligoesters thereof, and b. other raw materials required for the formation of an unsaturated polyester and ii. a copolymerizable monomer and 2.
Claim 2
Dependent Claim 94 words
An unsaturated polyester resin composition containing titanium dioxide comprising: 1. an unsaturated polyester resin containing titanium dioxide consisting of i. an unsaturated polyester containing titanium dioxide obtained from a. a depolycondensation product produced by depolycondensing a high molecular weight saturated polyester containing titanium dioxide by using one or more compounds selected from the group consisting of glycols, saturated dibasic acids or anhydrides thereof, unsaturated dibasic acids or anhydrides thereof, and esters or oligoesters thereof, and b. other raw materials required for the formation of an unsaturated polyester and ii. a copolymerizable monomer and 2.
Claim 3
Dependent Claim 86 words
at least one compound selected from the group consisting of A. a hydroxyalkylamine having at least one amino group and at least one hydroxyl group attached to different carbon atoms thereof, B. a polyoxyalkyleneamine, C. a mono- or dicarboxylate derived from the said compound (A) and D. a mono- or dicarboxylate derived from the said compound (B), wherein the amount of addition of the said compound (2) is in the range of from 0.01 to 1% by weight on the basis of the said unsaturated polyester
Claim 4
Dependent Claim 86 words
at least one compound selected from the group consisting of A. a hydroxyalkylamine having at least one amino group and at least one hydroxyl group attached to different carbon atoms thereof, B. a polyoxyalkyleneamine, C. a mono- or dicarboxylate derived from the said compound (A) and D. a mono- or dicarboxylate derived from the said compound (B), wherein the amount of addition of the said compound (2) is in the range of from 0.01 to 1% by weight on the basis of the said unsaturated polyester
Claim 5
Dependent Claim 62 words
resin. 2. The unsaturated polyester resin composition containing titanium dioxide according to claim 1, wherein the high molecular weight saturated polyester is at least one high molecular weight saturated polyester selected from the group consisting of polyethylene terephthalate, polyethylene terephthalate-isophthalate, polybutylene terephthalate, polyethylene-butylene terephthalate, polyethylene naphthalate and polyethylene terephthalate-naphthalate containing titanium dioxide in an amount of from 0.1 to 2% by weight.
Claim 6
Dependent Claim 59 words
The unsaturated polyester resin composition containing titanium dioxide according to claim 1, wherein the copolymerizable monomer is at least one compound selected from the group consisting of styrene, vinyl toluene, divinyl benzene, monochlorostyrene, tert-butyl styrene, α-methyl styrene, methyl acrylate, methyl methacrylate, diallyl phthalate, diallyl isophthalate, diallyl terephthalate, diallyl adipate, diallyl fumarate, dibutyl fumarate, triallylisocyanurate, vinyl acetate and mixtures thereof.
Claim 7
Dependent Claim 70 words
The unsaturated polyester resin composition containing titanium dioxide according to claim 1, wherein the hydroxyalkylamine (A) having at least one amino group and at least one hydroxyl group attached to different carbon atoms thereof is at least one compound selected from the group consisting of a monohydroxyalkyl monoamine (i), a polyhydroxyalkyl monoamine (ii), a monohydroxyalkyl polyamine (iii) and a polyhydroxyalkyl polyamine (iv), which are expressed by the following general formulas:
Claim 8
Dependent Claim 6 words
monohydroxyalkyl monoamine (i) R.sup.1 R.sup.2 N--A--OH,
Claim 9
Dependent Claim 6 words
monohydroxyalkyl monoamine (i) R.sup.1 R.sup.2 N--A--OH,
Claim 10
Dependent Claim 6 words
polyhydroxyalkyl monoamine (ii) R.sup.1 N(--A--OH).sub.2, n(--a--oh).sub.3,
Claim 11
Dependent Claim 6 words
polyhydroxyalkyl monoamine (ii) R.sup.1 N(--A--OH).sub.2, n(--a--oh).sub.3,
Claim 12
Dependent Claim 12 words
monohydroxyalkyl polyamine (iii) R.sup.1 R.sup.2 N--B--NR.sup.3 --A--OH, r.sup.1 r.sup.2 n--b--nr.sup.3 --b--nr.sup.4 --a--oh,
Claim 13
Dependent Claim 12 words
monohydroxyalkyl polyamine (iii) R.sup.1 R.sup.2 N--B--NR.sup.3 --A--OH, r.sup.1 r.sup.2 n--b--nr.sup.3 --b--nr.sup.4 --a--oh,
Claim 14
Dependent Claim 89 words
polyhydroxyalkyl polyamine (iv) R.sup.1 R.sup.2 N--B--N(--A--OH).sub.2, ho--a--r.sup.1 n--b--nr.sup.2 --a--oh, ho--A--R.sup.1 N--B--N(--A--OH).sub.2, (HO--A--).sub.2 N--B--N(--A--OH).sub.2, r.sup.1 r.sup.2 n--b--nr.sup.3 --b--n(--a--oh).sub.2, ho--a--r.sup.1 n--b--nr.sup.2 --b--nr.sup.3 --a--oh, ho--a--r.sup.1 n--b--nr.sup.2 --b--n(--a--oh).sub.2, (ho--a--).sub.2 n--b--nr.sup. --b--n(--a--oh).sub.2, and (HO--A--).sub.2 N--B--N(--A--OH)--B--N(--A--OH).sub.2, wherein R 1 , R 2 , R 3 and R 4 are hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, secbutyl, n-hexyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, lauryl, myristyl, palmityl, stearyl, oleyl, cyclohexyl, benzyl or phenyl, which may be the same or different, A is ethylene, propylene, thimethylene or tetramethylene, and B is ethylene, propylene, trimethylene, tetramethylene, cyclohexylene or phenylene.
Claim 15
Dependent Claim 89 words
polyhydroxyalkyl polyamine (iv) R.sup.1 R.sup.2 N--B--N(--A--OH).sub.2, ho--a--r.sup.1 n--b--nr.sup.2 --a--oh, ho--A--R.sup.1 N--B--N(--A--OH).sub.2, (HO--A--).sub.2 N--B--N(--A--OH).sub.2, r.sup.1 r.sup.2 n--b--nr.sup.3 --b--n(--a--oh).sub.2, ho--a--r.sup.1 n--b--nr.sup.2 --b--nr.sup.3 --a--oh, ho--a--r.sup.1 n--b--nr.sup.2 --b--n(--a--oh).sub.2, (ho--a--).sub.2 n--b--nr.sup. --b--n(--a--oh).sub.2, and (HO--A--).sub.2 N--B--N(--A--OH)--B--N(--A--OH).sub.2, wherein R 1 , R 2 , R 3 and R 4 are hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, secbutyl, n-hexyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, lauryl, myristyl, palmityl, stearyl, oleyl, cyclohexyl, benzyl or phenyl, which may be the same or different, A is ethylene, propylene, thimethylene or tetramethylene, and B is ethylene, propylene, trimethylene, tetramethylene, cyclohexylene or phenylene.
Claim 16
Dependent Claim 92 words
The unsaturated polyester resin composition containing titanium dioxide according to claim 1, wherein the hydroxyalkylamine (A) having at least one amino group and at least one hydroxyl group attached to different carbon atoms therof is at least one compound selected from the group consisting of ethanolamine, diethanolamine, triethanolamine, tris(2-hydroxypropyl)amine, tris(3-hydroxypropyl)amine, N-methylethanolamine, N-ethylethanolamine, N-n-propylethanolamine, N-isopropylethanolamine, N-n-butylethanolamine, N-sec-butylethanolamine, N-laurylethanolamine, N-stearylethanolamine, N-benzylethanolamine, N,N-dimethylethanolamine, N,N-diethylethanolamine, N,N-di-n-prophyethanolamine, N,N-diisopropylethanolamine, N,N-di-n-butylethanolamine, N,N-di-sec-butylethanolamine, N,N-dilaurylethanolamine, N,N-distearylethanolamine, N,N-dibenzylethanolamine, N,N-dimethyl-2-hydroxypropylamine, N,N-dimethyl-3-hydroxypropylamine, N,N-di-n-propyl-2-hydroxypropylamine, N,N-di-n-butyl-2-hydroxypropylamine, N-methyldiethanolamine, N-ethyldiethanolamine, N-n-propyldiethanolamine, N-isopropyldiethanolamine, N-n-butyldiethanolamine, N-lauryldiethanolamine, N-myristyldiethanolamine, N-oleyldiethanolamine, N-stearyldiethanolamine, N-benzyldiethanolamine, N-lauryl-bis(2-hydroxypropyl)amine, N-stearyl-bis(2-hydroxypropyl) amine, N,N-di-n-butyl-N'-(2-hydroxyethyl)ethylenediamine, N,N-di-n-butyl-N',N'-bis-(2-hydroxypropyl)propylenediamine, N,N,N', N'-tetrakis(2-hydroxyethyl)propylenediamine, and N,N,N'N',N" -pentakis(2-hydroxypropyl)diethylenetriamine.
Claim 17
Dependent Claim 44 words
The unsaturated polyester resin composition containing titanium dioxide according to claim 1, wherein the polyoxyalkyleneamine (B) is at least one compound selected from the group consisting of a polyoxyalkylene monoamine (v) and a polyoxyalkylene polyamine (vi) which are expressed by the following general formulas:
Claim 18
Dependent Claim 4 words
polyoxyalkylene monoamine (v) ##STR13##
Claim 19
Dependent Claim 4 words
polyoxyalkylene monoamine (v) ##STR13##
Claim 20
Dependent Claim 86 words
polyoxyalkylene polyamine (vi) ##STR14## wherein R 1 , R 2 , R 3 and R 4 are hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, secbutyl, n-hexyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, lauryl, myristyl, palmityl, stearyl, oleyl, cyclohexyl, benzyl or phenyl, which may be the same or different, A is ethylene, propylene, trimethylene or tetramethylene, B is ethylene, propylene, trimethylene, tetramethylene, cyclohexylene or phenylene, and x is a number of from 2 to 20 and y, z, w and v are numbers of from 1 to 20, respectively.
Claim 21
Dependent Claim 86 words
polyoxyalkylene polyamine (vi) ##STR14## wherein R 1 , R 2 , R 3 and R 4 are hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, secbutyl, n-hexyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, lauryl, myristyl, palmityl, stearyl, oleyl, cyclohexyl, benzyl or phenyl, which may be the same or different, A is ethylene, propylene, trimethylene or tetramethylene, B is ethylene, propylene, trimethylene, tetramethylene, cyclohexylene or phenylene, and x is a number of from 2 to 20 and y, z, w and v are numbers of from 1 to 20, respectively.
Claim 22
Dependent Claim 89 words
The unsaturated polyester resin composition containing titanium dioxide according to claim 6, wherein the polyoxyalkylene amine (B) is at least one compound selected from the group consisting of N-n-butyl-N-polyoxyethylene (x=2-20) amine, N-lauryl-N-polyoxyethylene (x=2-20) amine, N-myristyl-N-polyoxyethylene (x=2-20) amine, N-stearyl-N-polyoxyethylene (x=2-20) amine, N-N-di-n-butyl-N-polyoxyethylene (x=2-20)amine, N,N-dilauryl-N-polyoxyethylene (x=2-20) amine, N,N-distearyl-N-polyoxyethylene (x=2-20) amine, N-n-butyl-N,N-bis(polyoxyethylene) (x+y=3-20) amine, N-lauryl-N,N-bis(polyoxyethylene) (x+y=3-20) amine, N-myristyl-N,N-bis(polyoxyethylene) (x+y=3-20) amine, N-palmityl-N,N-bis(polyoxyethylene) x+y=3-20) amine, N-stearyl-N,N-bis (polyoxyethylene) (x+y=3-20) amine, N-stearyl-N-polyoxyethylene-N',N'-bis(polyoxyethylene) (x+y+z=4-20) trimethylenediamine, N,N,N',N'-tetrakis(polyoxyethylene) (x+y+z+w=5-20) propylenediamine, N,N,N',N',N"-pentakis(polyoxyethylene) (x+y+z+w+v=6-20) diethylenetriamine, N-lauryl-N-polyoxypropylene(x=2-20) amine, N-lauryl-N,N-bis(polyoxypropylene) (x+y=3-20) amine, N-stearyl-N,N-bis (polyoxypropylene) (x+y=3-20) amine, N-lauryl-N-polyoxypropylene-N',N'-bis(polyoxypropylene) (x+y+z=4-20) trimethylenediamine, and N,N,N',N',N"-pentakis(polyoxypropylene) (x+y+z+w+v=6-20) diethylenetriamine.
Claim 23
Dependent Claim 118 words
The unsaturated polyester resin composition containing titanium dioxide according to claim 1, wherein the mono- or dicarboxylate (C) derived from the hydroxyalkylamine (A) having at least one amino group and at least one hydroxy group attached to different carbon atoms thereof and the mono- or dicarboxylate (D) derived from the polyoxyalkyleneamine (B) are compounds in which at least one free hydroxyl group of the said compounds (A) and (B) is esterified with at least one organic acid selected from the group consisting of acetic acid, propionic acid, butyric acid, caproic acid, 2-ethylcaproic acid, caprylic acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, acrylic acid, methacrylic acid, succinic acid, adipic acid and sebacic acid.
Claim 24
Dependent Claim 89 words
The unsaturated polyester resin composition containing titanium dioxide according to claim 1, wherein the mono- or dicarboxylate (C) derived from the hydroxyalkylamine (A) having at least one amino group and at least one hydroxyl group attached to different carbon atoms thereof is at least one compound selected from the group consisting of diethanolamine monoacetate, diethanolamine dilaurate, triethanolamine monoacetate, triethanolamine monolaurate, triethanolamine monooleate, N,N-dimethylethanolamine acrylate, N,N-dimethylethanolamine methacrylate, N,N-diethylethanolamine diacetate, N,N-diethylethanolamine acrylate, N,N-diethylethanolamine methacrylate, N,N-diethyl-3-hydroxyproplamine acrylate, N,N-diethyl-3-hydroxypropylamine methacrylate, N,N-di-n-butylethanolamine acetate, N,N-di-n-butylethanolamine laurate, N,N-di-n-butylethanolamine adipate, N-n-butyldiethanolamine diacetate, N-n-butyldiethanolamine monolaurate, and N-lauryldiethanolamine diacetate.
Claim 25
Dependent Claim 52 words
The unsaturated polyester resin composition containing titanium dioxide according to claim 1, wherein the mono- or dicarboxylate (D) derived from the polyoxyalkyleneamine (B) is at least one compound selected from the group consisting of N-lauryl-N-polyoxyethylene (x=2-20) amine acetate, N-lauryl-N-polyoxypropylene (x=2-20) amine acetate, N-lauryl-N,N-bis(polyoxyethylene) (x+y32 3-20) amine diacetate and N-stearyl-N,N-bis(polyoxyethylene) (x+y=3-20) amine diacetate.
Claim 26
Dependent Claim 18 words
A molded product manufactured from the unsaturated polyester resin composition containing titanium dioxide as defined in claim 1.
Claim 27
Dependent Claim 63 words
The unsaturated polyester resin composition containing titanium dioxide according to claim 1, wherein the unsaturated polyester is obtained from (a) a depolycondensation product produced by depolycondensing a high molecular weight saturated polyester containing titanium dioxide in an amount of from 0.1 to 2% by weight by the use of one or more glycols and (b) an unsaturated dibasic acid or an anhydride thereof.
Claim 28
Dependent Claim 64 words
The unsaturated polyester resin composition containing titanium dioxide according to claim 12, wherein the glycol is at least one compound selected from the group consisting of ethylene glycol, propylene glycol, 1,3-propane diol, diethylene glycol, dipropylene glycol, 1,3-butylene glycol, 1,4-butane diol, 1,6-hexane diol, neopentyl glycol, cyclohexane dimethanol, 2,2,4-trimethyl-1,3-pentane diol, hydrogenated bisphenols, alkylene oxide addition products of bisphenols and alkylene oxide addition products of hydrogenated bisphenols.
Claim 29
Dependent Claim 39 words
The unsaturated polyester resin composition containing titanium dioxide according to claim 12, wherein the unsaturated dibasic acid is at least one compound selected from the group consisting of maleic acid, maleic anhydride, fumaric acid, itaconic acid and citraconic acid.
Claim 30
Dependent Claim 30 words
The unsaturated polyester resin composition containing titanium dioxide according to claim 6, wherein the sum of x, y, z, w, and v is a number of from 2 to 20.

References Cited (Backward Citations)

US2935489A Cited
US3446758A Cited
US3928253A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-04-04 1980-10-04 1981-04-05 $2000.00 Window Closed / Lapsed
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